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17 pages, 1016 KiB

Open AccessArticle

Zonal Chemical Signal Pathways Mediating Floral Induction in Apple

by Priyanka Reddy, Tim Plozza, Alessio Scalisi, Vilnis Ezernieks, Ian Goodwin and Simone Rochfort

Metabolites 2024, 14(5), 251; https://doi.org/10.3390/metabo14050251 - 25 Apr 2024

Viewed by 1160

Abstract

Phytohormones that trigger or repress flower meristem development in apple buds are thought to be locally emitted from adjacent plant tissues, including leaves and fruitlets. The presence of fruitlets is known to inhibit adjacent buds from forming flowers and thus fruits. The resulting [...] Read more.

Phytohormones that trigger or repress flower meristem development in apple buds are thought to be locally emitted from adjacent plant tissues, including leaves and fruitlets. The presence of fruitlets is known to inhibit adjacent buds from forming flowers and thus fruits. The resulting absence of fruitlets the following season restores flower-promoting signalling to the new buds. The cycle can lead to a biennial bearing behaviour of alternating crop loads in a branch or tree. The hormonal stimuli that elicit flowering is typically referred to as the floral induction (FI) phase in bud meristem development. To determine the metabolic pathways activated in FI, young trees of the cultivar ‘Ruby Matilda’ were subjected to zonal crop load treatments imposed to two leaders of bi-axis trees in the 2020/2021 season. Buds were collected over the expected FI phase, which is within 60 DAFB. Metabolomics profiling was undertaken to determine the differentially expressed pathways and key signalling molecules associated with FI in the leader and at tree level. Pronounced metabolic differences were observed in trees and leaders with high return bloom with significant increases in compounds belonging to the cytokinin, abscisic acid (ABA), phenylpropanoid and flavanol chemical classes. The presence of cytokinins, namely adenosine, inosine and related derivatives, as well as ABA phytohormones, provides further insight into the chemical intervention opportunities for future crop load management strategies via plant growth regulators. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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18 pages, 53335 KiB

Open AccessArticle

Citrus clementine Peel Essential Oil Ameliorates Potassium Dichromate-Induced Lung Injury: Insights into the PI3K/AKT Pathway

by Hany G. Attia, Suzan M. El-Morshedy, Ahmed M. Nagy, Ammar M. Ibrahim, Mohamed Aleraky, Sahar S. Abdelrahman, Samir M. Osman, Saeed M. Alasmari, Mohamed A. El Raey and Mohamed F. Abdelhameed

Metabolites 2024, 14(1), 68; https://doi.org/10.3390/metabo14010068 - 19 Jan 2024

Cited by 5 | Viewed by 2002

Abstract

Acute Lung Injury (ALI) is a life-threatening syndrome that has been identified as a potential complication of COVID-19. There is a critical need to shed light on the underlying mechanistic pathways and explore novel therapeutic strategies. This study aimed to examine the potential [...] Read more.

Acute Lung Injury (ALI) is a life-threatening syndrome that has been identified as a potential complication of COVID-19. There is a critical need to shed light on the underlying mechanistic pathways and explore novel therapeutic strategies. This study aimed to examine the potential therapeutic effects of Citrus clementine essential oil (CCEO) in treating potassium dichromate (PDC)-induced ALI. The chemical profile of CCEO was created through GC–MS analysis. An in vivo study in rats was conducted to evaluate the effect of CCEO administrated via two different delivery systems (oral/inhalation) in mitigating acute lung injury (ALI) induced by intranasal instillation of PDC. Eight volatile compounds were identified, with monoterpene hydrocarbons accounting for 97.03% of the identified constituents, including 88.84% of D-limonene. CCEO at doses of 100 and 200 mg/kg bw exhibited antioxidant and anti-inflammatory properties. These significant antioxidant properties were revealed through the reduction of malondialdehyde (MDA) and the restoration of reduced glutathione (GSH). In addition, inflammation reduction was observed by decreasing levels of cytokines tumor necrosis factor-α and tumor growth factor-β (TNF-α and TGF-β), along with an increase in phosphatidylinositide-3-kinase (PI3K) and Akt overexpression in lung tissue homogenate, in both oral and inhalation routes, compared to the PDC-induced group. These results were supported by histopathological studies and immunohistochemical assessment of TGF-β levels in lung tissues. These findings revealed that CCEO plays an integral role in relieving ALI induced by intranasal PDC and suggests it as a promising remedy. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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18 pages, 4800 KiB

Open AccessArticle

Analysis of Marrubiin in Marrubium alysson L. Extract Using Advanced HPTLC: Chemical Profiling, Acetylcholinesterase Inhibitory Activity, and Molecular Docking

by Nermeen A. Eltahawy, Asmaa I. Ali, Salma A. Ibrahim, Mohamed S. Nafie, Amal M. Sindi, Hanaa Alkharobi, Ahmad J. Almalki, Jihan M. Badr, Sameh S. Elhady and Reda F. A. Abdelhameed

Metabolites 2024, 14(1), 27; https://doi.org/10.3390/metabo14010027 - 30 Dec 2023

Cited by 2 | Viewed by 1781

Abstract

The main purpose of this work is to investigate the phytochemical composition of Marrubium alysson L. non-polar fraction. GC/MS analysis was used to evaluate the plant extract’s saponifiable and unsaponifiable matter. Although M. alysson L. lipoidal matter saponification produced 30.3% of fatty acid [...] Read more.

The main purpose of this work is to investigate the phytochemical composition of Marrubium alysson L. non-polar fraction. GC/MS analysis was used to evaluate the plant extract’s saponifiable and unsaponifiable matter. Although M. alysson L. lipoidal matter saponification produced 30.3% of fatty acid methyl esters and 69.7% of unsaponifiable matter. Phytol was the most dominant substance in the unsaponifiable materials. Notably, marrubiin which is one of the most prominent metabolites of Marrubium alysson L. was not detected through our adopted GC/MS technique. Thus, further characterization was proceeded through simple and rapid HPTLC analysis which successfully managed to identify marrubiin. Based on the regression equation, the concentration of marrubiin in M. alysson L. extract was 14.09 mg/g of dry extract. Concerning acetylcholinesterase inhibitory activity, both the crude M. alysson L. total methanolic extract and the non-polar fraction displayed reasonable inhibitory activity against acetylcholinesterase (AChE), whereas the pure compound marrubiin was considered to be the most effective and potent AChE inhibitor, with an IC₅₀ value of 52.66 (µM). According to the molecular docking studies, potential sites of interaction between the pure chemical marrubiin and AChE were examined. The results show that Tyr124 on AChE residue was critical to the activity of the aforementioned drug. Based on the depicted marrubin AChE inhibition activity and reported safety profile, this chemical metabolite is considered as a promising lead compound for further pre-clinical investigation as well as drug development and optimization. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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17 pages, 36002 KiB

Open AccessArticle

Tetraenone A: A New β-Ionone Derivative from Tetraena aegyptia

by Ahmed Ashour, Asmaa E. Sherif, Selwan M. El-Sayed, Ji-Young Kim, Dae Sik Jang, Abtin Anvari, Abdelbasset A. Farahat, Sabrin R. M. Ibrahim, Gamal A. Mohamed, Bayan E. Ainousah, Raghad F. Aljohani, Razan R. Al-Hejaili, Rahaf H. Khoja, Ahmed H. E. Hassan and Ahmed A. Zaki

Metabolites 2023, 13(12), 1202; https://doi.org/10.3390/metabo13121202 - 18 Dec 2023

Viewed by 1928

Abstract

In this study, the chemical investigation of Tetraena aegyptia (Zygophyllaceae) led to the identification of a new megastigmene derivative, tetraenone A ((2S, 5R, 6R, 7E)-2-hydroxy-5,6-dihydro-β-ionone) (1), along with (3S, 5R [...] Read more.

In this study, the chemical investigation of Tetraena aegyptia (Zygophyllaceae) led to the identification of a new megastigmene derivative, tetraenone A ((2S, 5R, 6R, 7E)-2-hydroxy-5,6-dihydro-β-ionone) (1), along with (3S, 5R, 6S, 7E)-3-hydroxy-5,6-epoxy-5,6-dihydro-β-ionone- (2), 3,4-dihydroxy-cinnamyl alcohol-4-glucoside (3), 3β,19α-dihydroxy-ursan-28-oic acid (4), quinovic acid (5), p-coumaric acid (6), and ferulic acid (7), for the first time. The chemical structures of 1–7 were confirmed by analysis of their 1D and 2D NMR and HRESIMS spectra and by their comparison with the relevant literature. The absolute configurations of 1 and 2 were assigned based on NOESY interactions and ECD spectra. Conformational analysis showed that 1 existed exclusively in one of the two theoretically possible chair conformers with a predominant s-trans configuration for the 3-oxobut-1-en-1-yl group with the ring, while the half-chair conformer had a pseudo-axial hydroxy group that was predominant over the other half-chair conformation. Boat conformations were not among the most stable conformations, and the s-trans isomerism was in favor of s-cis configuration. In silico investigation revealed that 1 and 2 had more favorable binding interactions with M^pro rather than with TMPRSS2. Accordingly, molecular dynamic simulations were performed on the complexes of compounds 1 and 2 with M^pro to explore the stability of their interaction with the target protein structure. Compounds 1 and 2 might offer a possible starting point for developing covalent inhibitors of M^pro of SARS-CoV-2. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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17 pages, 6957 KiB

Open AccessArticle

Curcumin Mitigates Malathion-Induced Renal Injury: Suppression of Apoptosis and Modulation of NF-κβ/TNF-α and Nrf2, and HO-1 Signaling

by Mamdouh Eldesoqui, Magda E. Ahmed, Mona A. Abdel-Kareem, Mohamed Moharram Badawy, Amal Fahmy Dawood, Abdelaty Shawky Mohamed, Ateya Megahed Ibrahim, Ahmed A. El-Mansi, Mohamad El-Sherbiny and Mahmoud Hendawy

Metabolites 2023, 13(11), 1117; https://doi.org/10.3390/metabo13111117 - 30 Oct 2023

Cited by 2 | Viewed by 1846

Abstract

Malathion is one of the most used organophosphorus pesticides that is used for many reasons such as agriculture and industry. Human exposure to malathion may occur through various means, such as eating food that has been treated with it. Malathion not only increases [...] Read more.

Malathion is one of the most used organophosphorus pesticides that is used for many reasons such as agriculture and industry. Human exposure to malathion may occur through various means, such as eating food that has been treated with it. Malathion not only increases oxidative stress but also decreases the antioxidant capacity. Curcumin is a powerful antioxidant with many pharmacological actions. Curcumin can act as a free radical scavenger and inhibit the activation and nuclear translocation of NF-κB. Curcumin could combat the lipid peroxidation and antioxidant depletion that trigger the apoptotic pathways. This study aims to examine the antioxidant, anti-inflammatory, and antiapoptotic effects of curcumin. Twenty-four Sprague Dawley rats were divided into four groups (six rats each): control, curcumin, malathion, and malathion + curcumin groups. At the assigned time, blood samples were used for the assessment of serum creatinine, and the kidneys were excised and washed; parts of them were used for the assessment of total oxidant status (TOS), oxidative stress index (OSI), the oxidative stress marker malondialdehyde (MDA), total antioxidant capacity (TAC), and glutathione (GSH) activity, other parts were fixed in formalin for further staining. Histopathological evaluation was performed for the fixed specimens after staining with H&E, sirus red, and the immunohistochemical staining for NF-κβ, TNF-α, Caspase-3, Nrf2, and HO-1. Curcumin significantly decreases the serum creatinine after malathion exposure and significantly restores the oxidant/antioxidant balance by increasing TAC and GSH and decreasing TOS, OSI, and MDA. Curcumin exerts its reno-protective effect and restores the histological architecture of the kidney by downregulating the immune expression of NF-κβ, TNF-α, and Caspase-3 and upregulating the expression of Nrf2 and HO-1. This study concluded that curcumin protects against nephrotoxicity caused by malathion by exerting its antioxidant, anti-inflammatory, and anti-apoptotic capabilities. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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17 pages, 4996 KiB

Open AccessArticle

Marine-Derived Compounds for CDK5 Inhibition in Cancer: Integrating Multi-Stage Virtual Screening, MM/GBSA Analysis and Molecular Dynamics Investigations

by Tagyedeen H. Shoaib, Mohammed A. Almogaddam, Yusra Saleh Andijani, Samaher Ahmad Saib, Najwa Mahmoud Almaghrabi, Abdulaziz Fahad Elyas, Rahmah Yasin Azzouni, Ehda Ahmad Awad, Shaimaa G. A. Mohamed, Gamal A. Mohamed, Sabrin R. M. Ibrahim, Hazem G. A. Hussein, Wadah Osman, Ahmed Ashour, Asmaa E. Sherif and Abdulrahim A. Alzain

Metabolites 2023, 13(10), 1090; https://doi.org/10.3390/metabo13101090 - 18 Oct 2023

Cited by 3 | Viewed by 2229

Abstract

Cyclin-dependent kinase 5 (CDK5) plays a crucial role in various biological processes, including immune response, insulin secretion regulation, apoptosis, DNA (deoxyribonucleic acid) damage response, epithelial−mesenchymal transition (EMT), cell migration and invasion, angiogenesis, and myogenesis. Overactivation of CDK5 is associated with the initiation and [...] Read more.

Cyclin-dependent kinase 5 (CDK5) plays a crucial role in various biological processes, including immune response, insulin secretion regulation, apoptosis, DNA (deoxyribonucleic acid) damage response, epithelial−mesenchymal transition (EMT), cell migration and invasion, angiogenesis, and myogenesis. Overactivation of CDK5 is associated with the initiation and progression of cancer. Inhibiting CDK5 has shown potential in suppressing cancer development. Despite advancements in CDK5-targeted inhibitor research, the range of compounds available for clinical and preclinical trials remains limited. The marine environment has emerged as a prolific source of diverse natural products with noteworthy biological activities, including anti-cancer properties. In this study, we screened a library of 47,450 marine natural compounds from the comprehensive marine natural product database (CMNPD) to assess their binding affinity with CDK5. Marine compounds demonstrating superior binding affinity compared to a reference compound were identified through high-throughput virtual screening, standard precision and extra-precision Glide docking modes. Refinement of the selected molecules involved evaluating molecular mechanics–generalized born surface area (MM/GBSA) free binding energy. The three most promising compounds, (excoecariphenol B, excoecariphenol A, and zyzzyanone B), along with the reference, exhibiting favorable binding characteristics were chosen for molecular dynamics (MD) simulations for 200 nanoseconds. These compounds demonstrated interaction stability with the target during MD simulations. The marine compounds identified in this study hold potential as effective CDK5 inhibitors and warrant subsequent experimental validation. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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16 pages, 10338 KiB

Open AccessArticle

Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of Ammi majus Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin

by Noha Fathallah, Mona El Deeb, Amany A. Rabea, Alshaimaa M. Almehmady, Hanaa Alkharobi, Sameh S. Elhady and Noha Khalil

Metabolites 2023, 13(10), 1044; https://doi.org/10.3390/metabo13101044 - 29 Sep 2023

Cited by 2 | Viewed by 1498

Abstract

Ammi majus, a well-established member of the Umbelliferae (Apiaceae) family, is endogenous to Egypt. The main parts of this plant that are used are the fruits, which contain coumarins and flavonoids as major active constituents. The roots are usually considered by-products that [...] Read more.

Ammi majus, a well-established member of the Umbelliferae (Apiaceae) family, is endogenous to Egypt. The main parts of this plant that are used are the fruits, which contain coumarins and flavonoids as major active constituents. The roots are usually considered by-products that are discarded and not fed to cattle because of coumarins’ potential toxicity. The goal of this study was to ensure the sustainability of the plant, investigate the active metabolites present in the roots using UPLC/MS-MS, isolate and elucidate the major coumarin Xanthotoxin, and predict its oral bioavailability and its potential biological impact on tongue papillae. The results revealed coumarins as the dominant chemical class in a positive acquisition mode, with bergaptol-O-hexoside 5%, Xanthotoxin 5.5%, and isoarnoittinin 6% being the major compounds. However, phenolics ruled in the negative mode, with p-coumaroyl tartaric acid 7%, 3,7-dimethyl quercetin 6%, and hesperidin 5% being the most prominent metabolites. Fractionation and purification of the chloroform fraction yielded Xanthotoxin as one of the main compounds, which appeared as white needle crystals (20 mg). ADME studies for oral bioavailability were performed to predict the potential properties of the compound if used orally. It was noted that it followed Lipinski’s rule of five, had just one parameter outside of the pink area in the radar plot, and was detected inside the threshold area using the boiled egg approach. In vivo, histopathological studies performed on rats showed a notable decrease in the tongue’s keratin thickness from an average of 51.1 µm to 9.1 µm and an average of 51.8 µm to 9.8 µm in fungiform and filiform cells, respectively. The results indicated that although Xanthotoxin is a well-known medical agent with several potential therapeutic activities in oral therapy, it may cause a destructive effect on the structure of the specialized mucosa of the tongue. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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23 pages, 3194 KiB

Open AccessArticle

Nutritional, Antioxidant, Antimicrobial, and Anticholinesterase Properties of Phyllanthus emblica: A Study Supported by Spectroscopic and Computational Investigations

by Mohamed A. A. Orabi, Aso Hameed Hasan, Sameh F. AbouZid, Dalia El Amir, Mona H. Hetta, Ahmed Abdullah Al Awadh, Omaish Salman Alqahtani, Tsutomu Hatano and Mohamed A. El-Shanawany

Metabolites 2023, 13(9), 1013; https://doi.org/10.3390/metabo13091013 - 14 Sep 2023

Cited by 7 | Viewed by 2307

Abstract

Dietary fruits and vegetables play a vital role as food and drugs and are the main sources of antioxidant defences against degenerative diseases, such as brain dysfunctions, cardiovascular diseases, immune system deteriorations, and cancers, brought on by oxidative damage. Phyllanthus emblica is a [...] Read more.

Dietary fruits and vegetables play a vital role as food and drugs and are the main sources of antioxidant defences against degenerative diseases, such as brain dysfunctions, cardiovascular diseases, immune system deteriorations, and cancers, brought on by oxidative damage. Phyllanthus emblica is a significant herbal remedy used in conventional medicine to recover lost strength and power. In this research, the potential value of Phyllanthus emblica as a food and drug is researched. The total phenolic, total flavonoid, and total tannin contents as well as the nutritional value, vitamin C, vitamin E, and mineral contents of different organs of P. emblica were evaluated. The antioxidant and antimicrobial activities of extracts and fractions of different organs of P. emblica were determined. A total of eleven flavonoids, simple phenolic, tannin-related phenolic, and tannin molecules were isolated from a hydroalcoholic extract of the leaves and fruits. The structures were identified by spectroscopic data and comparison with the literature values as gallic acid (1), naringenin 7-O-(6″-O-galloyl)-β-D-glucopyranoside (2), 3,3′-di-O-methyl ellagic acid-4′-O-β-d-glucopyranoside (3), 1-O-galloyl glycerol (4), 1,6-di-O-galloyl-β-d-glucopyranoside (5), flavogallonic acid bislactone (6), corilagin (7), ethyl gallate (8), urolithin M5 (9), (E)-p-coumaroyl-1-O-β-d-glucopyranoside (10), and 1,2,4,6-tetra-O-galloyl-β-d-glucopyranoside (11). Among them, compounds 3 and 10 are first isolated from the plant. Molecular docking was performed to investigate the comparative interactions between positive controls (galantamine and donepezil) and selected compounds utilizing acetylcholinesterase (4EY7) as a target receptor. Results exhibited the potency of these compounds against the target receptor. In summary, P. emblica has a wealth of minerals, vitamins C and E, and polyphenolic phytochemicals that may work together to treat infectious disease, prevent and/or treat oxidative-damage-related illnesses including Alzheimer’s disease. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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26 pages, 7207 KiB

Open AccessArticle

Deciphering Molecular Aspects of Potential α-Glucosidase Inhibitors within Aspergillus terreus: A Computational Odyssey of Molecular Docking-Coupled Dynamics Simulations and Pharmacokinetic Profiling

by Sameh S. Elhady, Noha M. Alshobaki, Mahmoud A. Elfaky, Abdulrahman E. Koshak, Majed Alharbi, Reda F. A. Abdelhameed and Khaled M. Darwish

Metabolites 2023, 13(8), 942; https://doi.org/10.3390/metabo13080942 - 12 Aug 2023

Cited by 3 | Viewed by 1989

Abstract

Hyperglycemia, as a hallmark of the metabolic malady diabetes mellitus, has been an overwhelming healthcare burden owing to its high rates of comorbidity and mortality, as well as prospective complications affecting different body organs. Available therapeutic agents, with α-glucosidase inhibitors as one [...] Read more.

Hyperglycemia, as a hallmark of the metabolic malady diabetes mellitus, has been an overwhelming healthcare burden owing to its high rates of comorbidity and mortality, as well as prospective complications affecting different body organs. Available therapeutic agents, with α-glucosidase inhibitors as one of their cornerstone arsenal, control stages of broad glycemia while showing definitive characteristics related to their low clinical efficiency and off-target complications. This has propelled the academia and industrial section into discovering novel and safer candidates. Herein, we provided a thorough computational exploration of identifying candidates from the marine-derived Aspergillus terreus isolates. Combined structural- and ligand-based approaches using a chemical library of 275 metabolites were adopted for pinpointing promising α-glucosidase inhibitors, as well as providing guiding insights for further lead optimization and development. Structure-based virtual screening through escalating precision molecular docking protocol at the α-glucosidase canonical pocket identified 11 promising top-docked hits, with several being superior to the market drug reference, acarbose. Comprehensive ligand-based investigations of these hits’ pharmacokinetics ADME profiles, physiochemical characterizations, and obedience to the gold standard Lipinski’s rule of five, as well as toxicity and mutagenicity profiling, proceeded. Under explicit conditions, a molecular dynamics simulation identified the top-stable metabolites: butyrolactone VI (SK-44), aspulvinone E (SK-55), butyrolactone I 4′’’’-sulfate (SK-72), and terrelumamide B (SK-173). They depicted the highest free binding energies and steadiest thermodynamic behavior. Moreover, great structural insights have been revealed, including the advent of an aromatic scaffold-based interaction for ligand–target complex stability. The significance of introducing balanced hydrophobic/polar moieties, like triazole and other bioisosteres of carboxylic acid, has been highlighted across docking, ADME/Tox profiling, and molecular dynamics studies for maximizing binding interactions while assuring safety and optimal pharmacokinetics for targeting the intestinal-localized α-glucosidase enzyme. Overall, this study provided valuable starting points for developing new α-glucosidase inhibitors based on nature-derived unique scaffolds, as well as guidance for prospective lead optimization and development within future pre-clinical and clinical investigations. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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20 pages, 3235 KiB

Open AccessArticle

Metabolome Mining of Curcuma longa L. Using HPLC-MS/MS and Molecular Networking

by Rabin Budhathoki, Arjun Prasad Timilsina, Bishnu P. Regmi, Khaga Raj Sharma, Niraj Aryal and Niranjan Parajuli

Metabolites 2023, 13(8), 898; https://doi.org/10.3390/metabo13080898 - 29 Jul 2023

Cited by 3 | Viewed by 2570

Abstract

Turmeric, Curcuma longa L., is a type of medicinal plant characterized by its perennial nature and rhizomatous growth. It is a member of the Zingiberaceae family and is distributed across the world’s tropical and subtropical climates, especially in South Asia. Its rhizomes have [...] Read more.

Turmeric, Curcuma longa L., is a type of medicinal plant characterized by its perennial nature and rhizomatous growth. It is a member of the Zingiberaceae family and is distributed across the world’s tropical and subtropical climates, especially in South Asia. Its rhizomes have been highly valued for food supplements, spices, flavoring agents, and yellow dye in South Asia since ancient times. It exhibits a diverse array of therapeutic qualities that encompass its ability to combat diabetes, reduce inflammation, act as an antioxidant, exhibit anticancer properties, and promote anti-aging effects. In this study, organic extracts of C. longa rhizomes were subjected to HPLC separation followed by ESI-MS and low-energy tandem mass spectrometry analyses. The Global Natural Product Social Molecular Networking (GNPS) approach was utilized for the first time in this ethnobotanically important species to conduct an in-depth analysis of its metabolomes based on their fragments. To sum it up, a total of 30 metabolites including 16 diarylheptanoids, 1 diarylpentanoid, 3 bisabolocurcumin ethers, 4 sesquiterpenoids, 4 cinnamic acid derivatives, and 2 fatty acid derivatives were identified. Among the 16 diarylheptanoids identified in this study, 5 of them are reported for the first time in this species. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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16 pages, 5451 KiB

Open AccessArticle

Non-Targeted Metabolomics Combined with Chemometrics by UHPLC–Orbitrap–HRMS and Antioxidant Activity of Atractylodes chinensis (DC.) Koidez. from Eight Origins

by Xueyan Gao, Danyang Ma, Kaiyuan Li, Tianjiao Xing, Xiwu Liu, Lingfeng Peng, Dawei Chen and Zhihui Hao

Metabolites 2023, 13(8), 888; https://doi.org/10.3390/metabo13080888 - 27 Jul 2023

Cited by 3 | Viewed by 1388

Abstract

Atractylodes chinensis (DC.) Koidez. (AC) is a type of Atractylodis Rhizoma that is widely used in China to treat diarrhea and arthritis, as well as a nutritional supplement. The objective of this study was to investigate and identify the phytochemicals in the aqueous [...] Read more.

Atractylodes chinensis (DC.) Koidez. (AC) is a type of Atractylodis Rhizoma that is widely used in China to treat diarrhea and arthritis, as well as a nutritional supplement. The objective of this study was to investigate and identify the phytochemicals in the aqueous extract of AC using an ultra-high-performance liquid chromatography (UHPLC)–Orbitrap–HRMS platform based on a non-targeted metabolomic approach. There were 76 compounds in the AC, the majority of which were phenylpropanoids (16) and terpenoids (15). The hierarchical clustering analysis (HCA) and principal component analysis (PCA) results revealed variations across eight AC samples and classified them into four groups. Using Pareto modeling, the orthogonal partial least squares-discriminant analysis (OPLS-DA) identified 11 distinct AC compounds. Furthermore, the antioxidant activity of eight AC samples was assessed using ABTS, DPPH, and OH· methods. The AC samples with concentrations ranging from 0 to 25 mg/mL had no toxic effects on A549 cells. They have a strong therapeutic potential against oxidation-related diseases, and further research on AC is warranted. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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23 pages, 6766 KiB

Open AccessArticle

Anti-Obesity Effect of a Tea Mixture Nano-Formulation on Rats Occurs via the Upregulation of AMP-Activated Protein Kinase/Sirtuin-1/Glucose Transporter Type 4 and Peroxisome Proliferator-Activated Receptor Gamma Pathways

by Mohamed A. Salem, Nora M. Aborehab, Mai M. Abdelhafez, Sameh H. Ismail, Nadine W. Maurice, May A. Azzam, Saleh Alseekh, Alisdair R. Fernie, Maha M. Salama and Shahira M. Ezzat

Metabolites 2023, 13(7), 871; https://doi.org/10.3390/metabo13070871 - 21 Jul 2023

Cited by 6 | Viewed by 2315

Abstract

White, green, and oolong teas are produced from the tea plant (Camellia sinensis (L.) Kuntze) and are reported to have anti-obesity and hypolipidemic effects. The current study aims to investigate the anti-obesity effects of a tea mixture nano-formulation by targeting the AMPK/Sirt-1/GLUT-4 [...] Read more.

White, green, and oolong teas are produced from the tea plant (Camellia sinensis (L.) Kuntze) and are reported to have anti-obesity and hypolipidemic effects. The current study aims to investigate the anti-obesity effects of a tea mixture nano-formulation by targeting the AMPK/Sirt-1/GLUT-4 axis in rats. In vitro lipase and α-amylase inhibition assays were used to determine the active sample, which was then incorporated into a nanoparticle formulation subjected to in vivo anti-obesity testing in rats by measuring the expression level of different genes implicated in adipogenesis and inflammation using qRT-PCR. Moreover, metabolomic analysis was performed for each tea extract using LC/ESI MS/MS coupled to chemometrics in an attempt to find a correlation between the constituents of the extracts and their biological activity. The in vitro pancreatic lipase and α-amylase inhibition assays demonstrated more effective activity in the tea mixture than the standards, orlistat and acarbose, respectively, and each tea alone. Thus, the herbal tea mixture and its nanoparticle formulation were evaluated for their in vivo anti-obesity activity. Intriguingly, the tea mixture significantly decreased the serum levels of glucose and triglycerides and increased the mRNA expression of GLUT-4, P-AMPK, Sirt-1, and PPAR-γ, which induce lipolysis while also decreasing the mRNA expression of TNF-α and ADD1/SREBP-1c, thereby inhibiting the inflammation associated with obesity. Our study suggests that the tea mixture nano-formulation is a promising therapeutic agent in the treatment of obesity and may also be beneficial in other metabolic disorders by targeting the AMPK/Sirt-1/Glut-4 pathway. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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13 pages, 3102 KiB

Open AccessArticle

Variation in Terpenoid and Flavonoid Content in Different Samples of Salvia semiatrata Collected from Oaxaca, Mexico, and Its Effects on Antinociceptive Activity

by Nancy Ortiz-Mendoza, Rubén San Miguel-Chávez, Martha Juana Martínez-Gordillo, Francisco Alberto Basurto-Peña, Mariana Palma-Tenango and Eva Aguirre-Hernández

Metabolites 2023, 13(7), 866; https://doi.org/10.3390/metabo13070866 - 20 Jul 2023

Viewed by 2002

Abstract

Salvia semiatrata Zucc. (Lamiaceae) is endemic to Oaxaca, Mexico, and is known for its analgesic properties. Terpenoids and phenolic compounds with antinociceptive potential have been characterised from this species. The aim of this research was to determine the variation in terpenoids and flavonoids [...] Read more.

Salvia semiatrata Zucc. (Lamiaceae) is endemic to Oaxaca, Mexico, and is known for its analgesic properties. Terpenoids and phenolic compounds with antinociceptive potential have been characterised from this species. The aim of this research was to determine the variation in terpenoids and flavonoids in ethyl acetate extracts of S. semiatrata collected from ten different localities, as well as to evaluate the antinociceptive effect between plants with higher and lower contents of these secondary metabolites. Quantification of S. semiatrata compounds was performed via HPLC-DAD, whereas in vivo evaluation of the antinociceptive effect was performed via formalin test. The results showed that the most abundant groups of metabolites are oleanolic acid (89.60–59.20 µg/mg), quercetin (34.81–16.28 µg/mg), catechin (11.30–9.30 µg/mg), and 7-keto-neoclerodan-3,13-dien-18,19:15,16-diolide (7-keto) (8.01–4.76 µg/mg). Principal component and canonical correspondence analysis showed that the most contrasting localities in terms of compound content and climatic variables are Miahuatlán and Santiago Huauclilla. The differences in metabolite content between the two locations did not affect the antinociceptive effects evaluated at a dose of 300 mg/kg, p.o. In conclusion, the results indicate that S. semiatrata is effective in relieving pain, regardless of the site of collection, reinforcing its traditional use as analgesic. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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17 pages, 4326 KiB

Open AccessFeature PaperArticle

The Effects of a High Concentration of Dissolved Oxygen on Actinobacteria from Lake Baikal

by Maria E. Dmitrieva, Ekaterina V. Malygina, Alexander Y. Belyshenko, Victoria N. Shelkovnikova, Natalia A. Imidoeva, Maria M. Morgunova, Tamara Y. Telnova, Anfisa A. Vlasova and Denis V. Axenov-Gribanov

Metabolites 2023, 13(7), 830; https://doi.org/10.3390/metabo13070830 - 7 Jul 2023

Cited by 1 | Viewed by 1561

Abstract

Among the diversity of microorganisms, the rarest and least explored are microorganisms that live in conditions of high oxygen in the environment and can experience the effects of natural oxidative stress. Here we suggest that the actinobacteria of Lake Baikal, sampled in the [...] Read more.

Among the diversity of microorganisms, the rarest and least explored are microorganisms that live in conditions of high oxygen in the environment and can experience the effects of natural oxidative stress. Here we suggest that the actinobacteria of Lake Baikal, sampled in the littoral zone, may produce natural products with antioxidant activity. The current study aimed to assess the effects of experimentally increased amounts of oxygen and ozone on the morphology of actinobacteria, DNA mutations, and antioxidant potential. In this experiment, we cultivated actinobacteria in liquid culture under conditions of natural aeration and increased concentrations of dissolved oxygen and ozone. Over a period of three months, bacterial samples were collected every week for further analysis. Morphological changes were assessed using the Gram method. A search for DNA mutations was conducted for the highly conserved 16S rRNA gene. The evaluation of antioxidant activity was performed using the DPPH test. The biotechnological potential was evaluated using high-resolution liquid chromatography-mass spectrometry approaches supplemented with the dereplication of natural products. We demonstrated the synthesis of at least five natural products by the Streptomyces sp. strain only under conditions of increased oxygen and ozone levels. Additionally, we showed morphological changes in Streptomyces sp. and nucleotide mutations in Rhodococcus sp. exposed to increased concentrations of dissolved oxygen and oxidative stress. Consequently, we demonstrated that an increased concentration of oxygen can influence Lake Baikal actinobacteria. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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18 pages, 2870 KiB

Open AccessArticle

Antioxidant and Anticancer Assessment and Phytochemical Investigation of Three Varieties of Date Fruits

by Ahmed S. Abdelbaky, Mohamed A. Tammam, Mohamed Yassin Ali, Marwa Sharaky, Khaled Selim, Wael M. Semida, Taia A. Abd El-Mageed, Mohamed Fawzy Ramadan, Hesham F. Oraby and Yasser M. Diab

Metabolites 2023, 13(7), 816; https://doi.org/10.3390/metabo13070816 - 3 Jul 2023

Cited by 4 | Viewed by 2711

Abstract

Date palm (Phoenix dactylifera L.) fruits contain high concentrations of phenolic compounds, particularly flavonoids and other micronutrients, which impact human health due to their potent antioxidant, anti-inflammatory, and anticancer characteristics. In the present study, the effect of ethyl acetate, hydroethanol, hydromethanol, and [...] Read more.

Date palm (Phoenix dactylifera L.) fruits contain high concentrations of phenolic compounds, particularly flavonoids and other micronutrients, which impact human health due to their potent antioxidant, anti-inflammatory, and anticancer characteristics. In the present study, the effect of ethyl acetate, hydroethanol, hydromethanol, and aqueous extract from three date palm varieties (i.e., Ajwa, Siwi, and Sukkari) on phytochemical profiles and antioxidant and anticancer activities was investigated. Fruit extracts were screened for their antioxidant activity using the DPPH· method. Phenolic constituents were quantified and identified using HPLC-DAD. Extracts (ethyl acetate, hydroethanol, and hydromethanol) were assessed for cytotoxicity on nine human cancer cell lines, i.e., MG-63, HCT116, MCF7, MDA-MB-231, HEPG2, HUH7, A549, H460, and HFB4, using the sulphorhodamine-B (SRB) assay. Results showed that the ethyl acetate extract of the Sukkari fruits has the greatest antioxidant potential with an IC₅₀ value of 132.4 ± 0.3 μg·mL⁻¹, while the aqueous extract of Ajwa date fruits exhibited the lowest antioxidant effect with an IC₅₀ value of 867.1 ± 0.3 μg·mL⁻¹. The extracts exhibited potent to moderate anticancer activities against the investigated cancer cell line in a source-dependent manner. Methanol extract of Siwi fruits exhibited the most potent anticancer activity (IC₅₀ = 99 ± 1.6 µg·mL⁻¹), followed by the same extract of Sukkari fruits with an IC₅₀ value of 119 ± 3.5 µg·mL⁻¹ against the cell line of human breast cancer (MDA-MB-231). Additionally, principal component analysis (PCA) was investigated to determine the relationship among the investigated traits and treatments. Our findings reveal that date palm fruit-derived extracts are excellent sources of biologically active constituents and substantiate their potential use in new anticancer strategies from natural resources. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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20 pages, 3867 KiB

Open AccessArticle

Evaluation and Comparison of Dermo-Cosmetic Activities of Three Oak Species by Targeting Antioxidant Metabolites and Skin Enzyme Inhibitors

by Gaëlle Buche, Malorie Laffon, Laëtitia Fougère and Emilie Destandau

Metabolites 2023, 13(7), 804; https://doi.org/10.3390/metabo13070804 - 28 Jun 2023

Cited by 1 | Viewed by 1301

Abstract

The two main species, sessile oak (Quercus petraea Liebl.) and pedunculate oak (Quercus robur L.), predominant in French forests, are mainly used for aging wines and spirits; however, the potential of oak wood extract as a source of natural antioxidants, due [...] Read more.

The two main species, sessile oak (Quercus petraea Liebl.) and pedunculate oak (Quercus robur L.), predominant in French forests, are mainly used for aging wines and spirits; however, the potential of oak wood extract as a source of natural antioxidants, due to its high polyphenol content, could be more widely exploited. This study focuses on three oak species, the two that are well-known, namely, sessile and pedunculate oak, and a third that has seldom been described and valorized, namely, pubescent oak (Quercus pubescens). Water extracts of these three species were fractionated by semi-preparative HPLC. The antioxidant activities of crude extracts and fractions were measured by colorimetric and enzymatic tests. The anti-elastase and anti-collagenase activities of the extracts and their fractions were also evaluated. In parallel, samples were analyzed by UHPLC-HRMS to correlate the activity with the molecular composition using molecular networks. The results obtained for the total extract of the three species were compared to determine if the activity depended on the species. The results within the same species were also compared to highlight which fraction and, therefore, which molecular family was involved in the activity of the total extract. The various antioxidant tests showed good activity of the total extract for the three species of oak and a very good anti-collagenase activity. The antioxidant activity of oak extract has already been proven in the literature and this is correlated with its richness in polyphenols. This study shows that each molecular family of the extract contributes to the activities of the total extract. Oak extract can be used to neutralize the ROS produced during oxidative stress and to prevent the degradation of collagen and elastase during skin aging. Its complementary properties make oak extract a valuable ingredient to act against skin aging. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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50 pages, 6181 KiB

Open AccessArticle

Conocarpus lancifolius (Combretaceae): Pharmacological Effects, LC-ESI-MS/MS Profiling and In Silico Attributes

by Muhammad Khurm, Yuting Guo, Qingqing Wu, Xinxin Zhang, Muhammad Umer Ghori, Muhammad Fawad Rasool, Imran Imran, Fatima Saqib, Muqeet Wahid and Zengjun Guo

Metabolites 2023, 13(7), 794; https://doi.org/10.3390/metabo13070794 - 27 Jun 2023

Cited by 1 | Viewed by 2560

Abstract

In folklore medicine, Conocarpus lancifolius is used to treat various illnesses. The main objective of this study was a comprehensive investigation of Conocarpus lancifolius leaf aqueous extract (CLAE) for its antioxidant, cardioprotective, anxiolytic, antidepressant and memory-enhancing capabilities by using different in vitro, in [...] Read more.

In folklore medicine, Conocarpus lancifolius is used to treat various illnesses. The main objective of this study was a comprehensive investigation of Conocarpus lancifolius leaf aqueous extract (CLAE) for its antioxidant, cardioprotective, anxiolytic, antidepressant and memory-enhancing capabilities by using different in vitro, in vivo and in silico models. The in vitro experimentation revealed that CLAE consumed an ample amount of total phenolics (67.70 ± 0.15 µg GAE/mg) and flavonoids (47.54 ± 0.45 µg QE/mg) with stronger antiradical effects through DPPH (IC₅₀ = 16.66 ± 0.42 µg/mL), TAC (77.33 ± 0.41 µg AAE/mg) and TRP (79.11 ± 0.67 µg GAE/mg) assays. The extract also displayed suitable acetylcholinesterase (AChE) inhibitory (IC₅₀ = 110.13 ± 1.71 µg/mL) activity through a modified Ellman’s method. The toxicology examination presented no mortality or any signs of clinical toxicity in both single-dose and repeated-dose tests. In line with the cardioprotective study, the pretreatment of CLAE was found to be effective in relieving the isoproterenol (ISO)-induced myocardial injury in rats by normalizing the heart weight index, serum cardiac biomarkers, lipid profile and various histopathological variations. In the noise-stress-induced model for behavior attributes, the results demonstrated that CLAE has the tendency to increase the time spent in the central zone and elevated open arms in the open field and elevated plus maze tests (examined for anxiety assessment), reduced periods of immobility in the forced swimming test (for depression) and improved recognition and working memory in the novel object recognition and Morris water maze tests, respectively. Moreover, the LC-ESI-MS/MS profiling predicted 53 phytocompounds in CLAE. The drug-likeness and ADMET analysis exhibited that the majority of the identified compounds have reasonable physicochemical and pharmacokinetic profiles. The co-expression of molecular docking and network analysis indicated that top-ranked CLAE phytoconstituents act efficiently against the key proteins and target multiple signaling pathways to exert its cardiovascular-protectant, anxiolytic, antidepressant and memory-enhancing activity. Hence, this artifact illustrates that the observed biological properties of CLAE elucidate its significance as a sustainable source of bioactive phytochemicals, which appears to be advantageous for pursuing further studies for the development of new therapeutic agents of desired interest. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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21 pages, 2701 KiB

Open AccessArticle

Açaí (Euterpe oleracea Mart.) Seed Oil Exerts a Cytotoxic Role over Colorectal Cancer Cells: Insights of Annexin A2 Regulation and Molecular Modeling

by Marcos Antonio Custódio Neto da Silva, Josiane Weber Tessmann, Kátia Regina Assunção Borges, Laís Araújo Souza Wolff, Fernanda Diniz Botelho, Leandro Alegria Vieira, Jose Andres Morgado-Diaz, Tanos Celmar Costa Franca, Maria do Carmo Lacerda Barbosa, Maria do Desterro Soares Brandão Nascimento, Murilo Ramos Rocha and João Ernesto de Carvalho

Metabolites 2023, 13(7), 789; https://doi.org/10.3390/metabo13070789 - 25 Jun 2023

Cited by 5 | Viewed by 1908

Abstract

Açaí, Euterpe oleracea Mart., is a native plant from the Amazonian and is rich in several phytochemicals with anti-tumor activities. The aim was to analyze the effects of açaí seed oil on colorectal adenocarcinoma (ADC) cells. In vitro analyses were performed on CACO-2, [...] Read more.

Açaí, Euterpe oleracea Mart., is a native plant from the Amazonian and is rich in several phytochemicals with anti-tumor activities. The aim was to analyze the effects of açaí seed oil on colorectal adenocarcinoma (ADC) cells. In vitro analyses were performed on CACO-2, HCT-116, and HT-29 cell lines. The strains were treated with açaí seed oil for 24, 48, and 72 h, and cell viability, death, and morphology were analyzed. Molecular docking was performed to evaluate the interaction between the major compounds in açaí seed oil and Annexin A2. The viability assay showed the cytotoxic effect of the oil in colorectal adenocarcinoma cells. Acai seed oil induced increased apoptosis in CACO-2 and HCT-116 cells and interfered with the cell cycle. Western blotting showed an increased expression of LC3-B, suggestive of autophagy, and Annexin A2, an apoptosis regulatory protein. Molecular docking confirmed the interaction of major fatty acids with Annexin A2, suggesting a role of açaí seed oil in modulating Annexin A2 expression in these cancer cell lines. Our results suggest the anti-tumor potential of açaí seed oil in colorectal adenocarcinoma cells and contribute to the development of an active drug from a known natural product. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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15 pages, 1125 KiB

Open AccessArticle

In Vitro and In Silico Anti-Picornavirus Triterpene Alkanoic Acid Ester from Saudi Collection of Rhazya stricta Decne

by Maged S. Abdel-Kader, Fahad S. Almutib, Abdullah F. Aldosari, Gamal A. Soliman, Hisham Y. Elzorba, Mohammed H. Alqarni, Reham S. Ibrahim and Hala H. Zaatout

Metabolites 2023, 13(6), 750; https://doi.org/10.3390/metabo13060750 - 13 Jun 2023

Viewed by 1964

Abstract

The total alcohol extract obtained from the aerial parts of R. stricta and fractions of the liquid–liquid fractionation process were tested against picornavirus-causing foot-and-mouth disease (FMD) based on the traditional use of the plant in Saudi Arabia. The most active petroleum ether soluble [...] Read more.

The total alcohol extract obtained from the aerial parts of R. stricta and fractions of the liquid–liquid fractionation process were tested against picornavirus-causing foot-and-mouth disease (FMD) based on the traditional use of the plant in Saudi Arabia. The most active petroleum ether soluble fraction was subjected to chromatographic purification, and nine compounds were isolated, identified using various chemical and spectroscopic methods, and tested for their anti-viral potential. The new ester identified as α-Amyrin 3-(3′R-hydroxy)-hexadecanoate (1) was the most active compound with 51% inhibition of the viral growth and was given the name Rhazyin A. Compounds with ursane skeleton were more active than those with lupane skeleton except in the case of the acid derivatives where betulenic acid showed 26.1% inhibition against the viral growth, while ursolic acid showed only 16.6% inhibition. Moreover, molecular docking analysis using a glide extra-precision module was utilized for investigating the possible molecular interactions accounting for anti-viral activity against picornavirus of the nine isolated compounds. Molecular docking studies revealed a strong binding of the discovered hits within the active site of FMDV 3C^pro. Compound 1 showed the lowest docking score within the nine isolated compounds comparable to the two known anti-viral drugs; glycyrrhizic acid and ribavirin. The results of this research will provide lead candidates from natural origin with potential safety and efficacy compared to the synthetic ones with lower production costs for managing FMVD. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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19 pages, 1423 KiB

Open AccessArticle

Elaboration and Characterization of Pereskia aculeate Miller Extracts Obtained from Multiple Ultrasound-Assisted Extraction Conditions

by Maria Clara Coutinho Macedo, Viviane Dias Medeiros Silva, Mateus Sá Magalhães Serafim, Vinícius Tadeu da Veiga Correia, Débora Tamires Vitor Pereira, Patrícia Regina Amante, Antônio Soares Júnior da Silva, Henrique de Oliveira Prata Mendonça, Rodinei Augusti, Ana Cardoso Clemente Filha Ferreira de Paula, Júlio Onésio Ferreira Melo, Christiano Vieira Pires and Camila Argenta Fante

Metabolites 2023, 13(6), 691; https://doi.org/10.3390/metabo13060691 - 26 May 2023

Cited by 3 | Viewed by 2284

Abstract

Pereskia aculeata Miller, is an unconventional food plant native to South America. This study aimed to investigate the influence of different ultrasonic extraction times (10, 20, 30, and 40 min) on the phytochemical profile, antioxidant and antibacterial activities of ethanolic extracts obtained from [...] Read more.

Pereskia aculeata Miller, is an unconventional food plant native to South America. This study aimed to investigate the influence of different ultrasonic extraction times (10, 20, 30, and 40 min) on the phytochemical profile, antioxidant and antibacterial activities of ethanolic extracts obtained from lyophilized Pereskia aculeate Miller (ora-pro-nobis) leaves, an under-researched plant. Morphological structure and chemical group evaluations were also conducted for the lyophilized P. aculeate leaves. The different extraction times resulted in distinct phenolic content and Antioxidant Activity (ATT) values. Different extraction time conditions resulted in phenolic compound contents ranging from 2.07 to 2.60 mg EAG.g⁻¹ of extract and different ATT values. The ATT evaluated by DPPH was significantly higher (from 61.20 to 70.20 μM of TE.g⁻¹ of extract) in extraction times of 30 and 40 min, respectively. For ABTS, it varied between 6.38 and 10.24 μM of TE.g⁻¹ of extract and 24.34 and 32.12 μM ferrous sulp.g⁻¹ of extract. All of the obtained extracts inhibited the growth of Staphylococcus aureus, particularly the treatment employing 20 min of extraction at the highest dilution (1.56 mg.mL⁻¹). Although liquid chromatography analyses showed that chlorogenic acid was the primary compound detected for all extracts, Paper Spray Mass Spectrometry (PS-MS) suggested the extracts contained 53 substances, such as organic, fatty, and phenolic acids, sugars, flavonoids, terpenes, phytosterols, and other components. The PS-MS proved to be a valuable technique to obtain the P. aculeate leaves extract chemical profile. It was observed that the freeze-drying process enhanced the conservation of morphological structures of P. aculeate leaves, as evidenced by scanning electron microscopy (SEM). Fourier transform infrared spectroscopy (FTIR) identified carboxyl functional groups and proteins between the 1000 and 1500 cm⁻¹ bands in the P. aculeate leaves, thus favoring water interaction and contributing to gel formation. To the best of our knowledge, this is the first study to evaluate different times (10, 20, 30 and 40 min) for ultrasound extraction of P. aculeate leaves. The polyphenols improved extraction, and high antioxidant activity demonstrates the potential for applying P. aculeate leaves and their extract as functional ingredients or additives in the food and pharmaceutical industries. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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17 pages, 1377 KiB

Open AccessArticle

Development and Characterization of Yellow Passion Fruit Peel Flour (Passiflora edulis f. flavicarpa)

by Maria Clara Coutinho Macedo, Vinícius Tadeu da Veiga Correia, Viviane Dias Medeiros Silva, Débora Tamires Vitor Pereira, Rodinei Augusti, Júlio Onésio Ferreira Melo, Christiano Vieira Pires, Ana Cardoso Clemente Filha Ferreira de Paula and Camila Argenta Fante

Metabolites 2023, 13(6), 684; https://doi.org/10.3390/metabo13060684 - 25 May 2023

Cited by 11 | Viewed by 2853

Abstract

In this study, the peels of the yellow passion fruit (Passiflora edulis f. flavicarpa) were used to develop a flour that was evaluated in terms of its physicochemical, microscopic, colorimetric, and granulometric characteristics, its total phenolic compound and carotenoid contents, and its [...] Read more.

In this study, the peels of the yellow passion fruit (Passiflora edulis f. flavicarpa) were used to develop a flour that was evaluated in terms of its physicochemical, microscopic, colorimetric, and granulometric characteristics, its total phenolic compound and carotenoid contents, and its antioxidant capacity. Fourier Transform Infrared (FTIR) spectroscopy measurements were employed to investigate the constituent functional groups, compounds’ chemical profiles were assessed by Paper Spray Mass Spectrometry (PS-MS), and the compound’s chemical profiles were evaluated by Ultra-Performance Liquid Chromatography (UPLC). This flour presented a light color, heterogeneous granulometry, high carbohydrate, carotenoid, and total phenolic compound contents with high antioxidant capacity. Scanning Electron Microscopy (SEM) showed a particulate flour, which is supposed to contribute to its compactness. FTIR demonstrated the presence of functional groups corresponding to cellulose, hemicellulose, and lignin, constituents of insoluble dietary fiber. The PS-MS analysis suggested the presence of 22 substances, covering diverse component classes such as organic, fatty, and phenolic acids, flavonoids, sugars, quinones, phenylpropanoid glycerides terpenes, and amino acids. This research demonstrated the potential of using Passion Fruit Peel Flour (PFPF) as an ingredient for food products. The advantages of using PFPF comprise the reduction of agro-industrial waste, contribution to the development of a sustainable food system, and increment of food products’ functional profile. Moreover, its high content of several bioactive compounds can benefit consumers’ health. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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16 pages, 9232 KiB

Open AccessArticle

Computational Insights into Natural Antischistosomal Metabolites as SmHDAC8 Inhibitors: Molecular Docking, ADMET Profiling, and Molecular Dynamics Simulation

by Abdulrahim A. Alzain, Rua M. Mukhtar, Nihal Abdelmoniem, Fatima A. Elbadwi, Amira Hussien, Elrashied A. E. Garelnabi, Wadah Osman, Asmaa E. Sherif, Amgad I. M. Khedr, Kholoud F. Ghazawi, Waad A. Samman, Sabrin R. M. Ibrahim, Gamal A. Mohamed and Ahmed Ashour

Metabolites 2023, 13(5), 658; https://doi.org/10.3390/metabo13050658 - 15 May 2023

Cited by 7 | Viewed by 2111

Abstract

Schistosomiasis is a neglected tropical disease with a significant socioeconomic impact. It is caused by several species of blood trematodes from the genus Schistosoma, with S. mansoni being the most prevalent. Praziquantel (PZQ) is the only drug available for treatment, but it [...] Read more.

Schistosomiasis is a neglected tropical disease with a significant socioeconomic impact. It is caused by several species of blood trematodes from the genus Schistosoma, with S. mansoni being the most prevalent. Praziquantel (PZQ) is the only drug available for treatment, but it is vulnerable to drug resistance and ineffective in the juvenile stage. Therefore, identifying new treatments is crucial. SmHDAC8 is a promising therapeutic target, and a new allosteric site was discovered, providing the opportunity for the identification of a new class of inhibitors. In this study, molecular docking was used to screen 13,257 phytochemicals from 80 Saudi medicinal plants for inhibitory activity on the SmHDAC8 allosteric site. Nine compounds with better docking scores than the reference were identified, and four of them (LTS0233470, LTS0020703, LTS0033093, and LTS0028823) exhibited promising results in ADMET analysis and molecular dynamics simulation. These compounds should be further explored experimentally as potential allosteric inhibitors of SmHDAC8. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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14 pages, 2096 KiB

Open AccessArticle

Secondary Metabolites Profiling, Antimicrobial and Cytotoxic Properties of Commiphora gileadensis L. Leaves, Seeds, Callus, and Cell Suspension Extracts

by Ayed M. Al-Abdallat, Batool K. Adayileh, Jamal S. Sawwan, Rida Shibli, Tamara S. Al-Qudah, Bashaer Abu-Irmaileh, Randa N. Albdaiwi, Jehad Almaliti and Yasser Bustanji

Metabolites 2023, 13(4), 537; https://doi.org/10.3390/metabo13040537 - 10 Apr 2023

Cited by 8 | Viewed by 2718

Abstract

Commiphora gileadensis L. is an important endangered medicinal plant that belongs to the family Burseraceae. In this study, C. gileadensis callus culture was established successfully using mature leaves as explants cultured on Murashige and Skoog (MS) media supplemented with 24.50 μM of indole butyric acid [...] Read more.

Commiphora gileadensis L. is an important endangered medicinal plant that belongs to the family Burseraceae. In this study, C. gileadensis callus culture was established successfully using mature leaves as explants cultured on Murashige and Skoog (MS) media supplemented with 24.50 μM of indole butyric acid (IBA) and 2.22 μM 6-Benzylaminopurine (BAP) (callus induction media). The obtained callus was maintained on MS medium supplemented with 16.11 μM naphthalene acetic acid (NAA) in combination with 6.66 μM BAP, which resulted in a substantial increase in callus fresh and dry weights. The cell suspension culture was established successfully using liquid callus induction media supplemented with 3.0 mg·L⁻¹ proline. Thereafter, the chemical constituents of different C. gileadensis methanolic extracts (callus, cell suspension, leaves, and seeds) were profiled, and their cytotoxic and antimicrobial properties were investigated. The LC-MS GNPS analyses were applied for chemical profiling of the methanolic plant extracts, and several natural products were identified, including flavonols, flavanones, and flavonoids glycosides, with two unusual families that included puromycin, 10-hydroxycamptothecin, and justicidin B. The methanolic extracts have shown selective antimicrobial and cytotoxic properties against different microbes and cancer cell lines. For instance, leaf extract showed the highest zone of inhibition for Staphylococcus aureus, while cell suspension culture was effective against Staphylococcus epidermidis and Staphylococcus aureus. All extracts showed selective activity against A549 cell lines for the cytotoxicity assay, while the leaf extract had a broad cytotoxic effect against all tested cell lines. This study revealed that C. gileadensis callus and cell suspension cultures can be employed to increase the in vitro formation of biologically active compounds that may have cytotoxicity and antibacterial action against different cancer cell lines and bacterial species. Further studies are required to isolate and identify such constituents that corroborate the observed activities. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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15 pages, 2715 KiB

Open AccessArticle

Optimization of Phenolic Compounds Extraction and Antioxidant Activity from Inonotus hispidus Using Ultrasound-Assisted Extraction Technology

by Liliana Machado-Carvalho, Tânia Martins, Alfredo Aires and Guilhermina Marques

Metabolites 2023, 13(4), 524; https://doi.org/10.3390/metabo13040524 - 5 Apr 2023

Cited by 17 | Viewed by 2916

Abstract

The use of ultrasound-assisted extraction (UAE) of bioactive compounds has been increasing because it is a good alternative to the conventional extraction methods. UAE was used to maximize total polyphenol content (TPC), 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging capacity, and ferric reducing antioxidant power (FRAP) of [...] Read more.

The use of ultrasound-assisted extraction (UAE) of bioactive compounds has been increasing because it is a good alternative to the conventional extraction methods. UAE was used to maximize total polyphenol content (TPC), 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging capacity, and ferric reducing antioxidant power (FRAP) of the mushroom Inonotus hispidus using response surface methodology (RSM). Firstly, the effect of 40% (v/v) ethanol and 80% (v/v) methanol on the TPC, DPPH scavenging capacity, and FRAP was evaluated. The ethanolic extracts showed a significantly higher (p < 0.0001) TPC, DPPH scavenging capacity, and FRAP than the methanolic extracts. The best condition to produce an extract with the higher TPC and antioxidant activity was achieved when using 40% (v/v) ethanol, a ratio of 75 mL/g, and an extraction time of 20 min. The chromatographic profile of the extract obtained in the optimized condition revealed that hispidin is the main polyphenol present in the extracts of I. hispidus, representing, together with hispidin-like compounds, the majority of the phenolic compounds (159.56 µg/g DW out of 219.01 µg/g DW). The model allowed us to optimize the conditions to maximize the extraction of phenolic compounds with antioxidant activity from I. hispidus, demonstrating its potential as a source of antioxidant compounds, with possible industrial, pharmaceutical, and food applications. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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16 pages, 3317 KiB

Open AccessArticle

Phytochemicals Identification and Bioactive Compounds Estimation of Artemisia Species Grown in Saudia Arabia

by Abdalrhaman M. Salih, Ahmed A. Qahtan and Fahad Al-Qurainy

Metabolites 2023, 13(3), 443; https://doi.org/10.3390/metabo13030443 - 17 Mar 2023

Cited by 8 | Viewed by 2715

Abstract

Artemisia species are very important medicinal plants, particularly in the Middle East and in developing countries. Their products have been used in traditional and medicine contemporary for the treating of infectious ulcers, gangrenous ulcers, inflammations, and malaria. Artemisinin derived from Artemisia species has [...] Read more.

Artemisia species are very important medicinal plants, particularly in the Middle East and in developing countries. Their products have been used in traditional and medicine contemporary for the treating of infectious ulcers, gangrenous ulcers, inflammations, and malaria. Artemisinin derived from Artemisia species has been used as a drug in many countries for malaria disease treatment. Hence, this study aimed to identify and evaluate the bioactive compounds of three species of Artemisia (Artemisia judaica, Artemisia monosperma, and Artemisia sieberi) growing in Saudi Arabia. Therefore, several analytical techniques, such as gas chromatography–mass spectrometry (GC-MS), UV-Visible spectrophotometry (UV-Vis), and high-performance liquid chromatography (HPLC), with reference standards, were used. The GC-MS analysis of the artemisia species revealed many bioactive constituents associated with plant secondary metabolites; some of these identified phytochemical components have biological activity. A. Judaica showed the highest number of bioactive compounds, followed by A. sieberi and A. monosperma. Further, the total phenol, total flavonoid, total tannin, terpenoids, and TCA were estimated. Furthermore, biomolecules such gallic acid, tannin acid, quercetin, and artemisinin in different artemisia species were quantified using HPLC with the reference standard. The amount of artemisinin in the leaf extract of these species (A. sieberi, A. Judaica, and A. monosperma) was found to be about 3.01, 2.5, and 1.9 mg/g DW, respectively. Moreover, the antioxidant activity of the samples was estimated. The obtained results have shown that these species possessed high antioxidant activity, and the scavenging of the DPPH radical and hydrogen peroxide were found to be raised with the increase in the plant extract concentration. This reflects the number of bioactive compounds in these species. The findings of this research support and justify the utilization of Artemisia species in folk medicine in the Middle East. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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13 pages, 1137 KiB

Open AccessArticle

The Invasive Anemone Condylactis sp. of the Coral Reef as a Source of Sulfur- and Nitrogen-Containing Metabolites and Cytotoxic 5,8-Epidioxy Steroids

by Atallah F. Ahmed, Chang-Feng Dai, Yao-Haur Kuo and Jyh-Horng Sheu

Metabolites 2023, 13(3), 392; https://doi.org/10.3390/metabo13030392 - 7 Mar 2023

Cited by 1 | Viewed by 1856

Abstract

The Condylactis-genus anemones were examined for their proteinaceous poisons over 50 years ago. On the other hand, the current research focuses on isolating and describing the non-proteinaceous secondary metabolites from the invasive Condylactis anemones, which help take advantage of their population outbreak [...] Read more.

The Condylactis-genus anemones were examined for their proteinaceous poisons over 50 years ago. On the other hand, the current research focuses on isolating and describing the non-proteinaceous secondary metabolites from the invasive Condylactis anemones, which help take advantage of their population outbreak as a new source of chemical candidates and potential drug leads. From an organic extract of Condylactis sp., a 1,2,4-thiadiazole-based alkaloid, identified as 3,5-bis(3-pyridinyl)-1,2,4-thiadiazole (1), was found to be a new natural alkaloid despite being previously synthesized. The full assignment of NMR data of compound 1, based on the analysis of 2D NMR correlations, is reported herein for the first time. The proposed biosynthetic precursor thionicotinamide (2) was also isolated for the first time from nature along with nicotinamide (3), uridine (5), hypoxanthine (6), and four 5,8-epidioxysteroids (7–10). A major secondary metabolite (−)-betonicine (4) was isolated from Condylactis sp. and found for the first time in marine invertebrates. The four 5,8-epidioxysteroids, among other metabolites, exhibited cytotoxicity (IC₅₀ 3.5–9.0 μg/mL) toward five cancer cell lines. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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12 pages, 1141 KiB

Open AccessArticle

Natural Corynanthe-Type Cholinesterase Inhibitors from Malaysian Uncaria attenuata Korth.: Isolation, Characterization, In Vitro and In Silico Studies

by Nelson Jeng-Yeou Chear, Tan Ai Fein Ching-Ga, Kooi-Yeong Khaw, Francisco León, Wen-Nee Tan, Siti R. Yusof, Christopher R. McCurdy, Vikneswaran Murugaiyah and Surash Ramanathan

Metabolites 2023, 13(3), 390; https://doi.org/10.3390/metabo13030390 - 7 Mar 2023

Cited by 1 | Viewed by 2428

Abstract

The Uncaria genus is notable for its therapeutic potential in treating age-related dementia, such as Alzheimer’s disease. A phytochemical study of the leaves of Malaysian Uncaria attenuata Korth., afforded an undescribed natural corynanthe-type oxindole alkaloid, isovillocarine D (1) together with two [...] Read more.

The Uncaria genus is notable for its therapeutic potential in treating age-related dementia, such as Alzheimer’s disease. A phytochemical study of the leaves of Malaysian Uncaria attenuata Korth., afforded an undescribed natural corynanthe-type oxindole alkaloid, isovillocarine D (1) together with two known indole alkaloids, villocarine A (2) and geissoschizine methyl ether (3), and their structural identification was performed with extensive mono- and bidimensional NMR and MS spectroscopic methods. The isolated alkaloids were evaluated for their acetylcholinesterase (AChE)- and butyrylcholinesterase (BChE)-inhibitory activity. The results indicated that compound (2) was the most potent inhibitor against both AChE and BChE, with IC₅₀ values of 14.45 and 13.95 µM, respectively, whereas compounds (1) and (3) were selective BChE inhibitors with IC₅₀ values of 35.28 and 17.65 µM, respectively. In addition, molecular docking studies revealed that compound (2) interacts with the five main regions of AChE via both hydrogen and hydrophobic bonding. In contrast to AChE, the interactions of (2) with the enzymatic site of BChE are established only through hydrophobic bonding. The current finding suggests that U. attenuata could be a good source of bioactive alkaloids for treating age-related dementia. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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20 pages, 4942 KiB

Open AccessArticle

Biopreservative Effect of the Tunisian Halophyte Lobularia maritima Flavonoid Fraction, Used Alone and in Combination with Linalool in Stored Minced Beef Meat

by Boutheina Ben Akacha, Stefania Garzoli, Rania Ben Saad, Faical Brini, Wissem Mnif, Miroslava Kačániová and Anis Ben Hsouna

Metabolites 2023, 13(3), 371; https://doi.org/10.3390/metabo13030371 - 2 Mar 2023

Cited by 11 | Viewed by 1790

Abstract

In the present study, Lobularia maritima (Lm) flavonoid extract (LmFV) was characterized by HPLC analyses and five compounds were detected. Further, to describe the chemical content of the matrix, GC-MS analyses after silylation were performed; the obtained results showed [...] Read more.

In the present study, Lobularia maritima (Lm) flavonoid extract (LmFV) was characterized by HPLC analyses and five compounds were detected. Further, to describe the chemical content of the matrix, GC-MS analyses after silylation were performed; the obtained results showed the presence of a large number of components belonging to several chemical classes, mostly sugar alcohols, sugars, fatty acids, and terpenes. Firstly, the antibacterial activities of this fraction and linalool (Lin) were evaluated against eight foodborne pathogenic strains with MIC values between 2.3 and 5.8 mg/mL and 0.23 and 0.7 mg/mL, respectively. Then, the antioxidant activity of both was evaluated by the DPPH antiradical test and the phosphomolybdenum test. Furthermore, the biopreservative effect of LmFV alone and in combination with Lin on minced beef stored at 4 °C for 14 days was evaluated using microbiological and physiochemical tests. LmFV at 4.6% alone significantly reduced microbial spoilage in ground meat (p < 0.05). The combination of LmFV (4.6%) and Lin (0.46%) was more effective than LmFV alone in inhibiting bacterial contamination, reducing TBARS values and the risk of bacterial contamination, and reducing the accumulation of Met myoglobin (MetMb). This combination, therefore, extends the shelf life of the product by about 10 days. Based on these microbiological results and physicochemical parameters, it can be stated that the addition of Lin potentiates the flavonoid fraction of L. maritima more strongly against the deterioration of meat quality by significantly improving its biopreservative effect as a natural conservative. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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28 pages, 3451 KiB

Open AccessArticle

Breynia cernua: Chemical Profiling of Volatile Compounds in the Stem Extract and Its Antioxidant, Antibacterial, Antiplasmodial and Anticancer Activity In Vitro and In Silico

by Hesti Lina Wiraswati, Nisa Fauziah, Gita Widya Pradini, Dikdik Kurnia, Reza Abdul Kodir, Afiat Berbudi, Annisa Retno Arimdayu, Amila Laelalugina, Supandi and Ilma Fauziah Ma'ruf

Metabolites 2023, 13(2), 281; https://doi.org/10.3390/metabo13020281 - 15 Feb 2023

Cited by 6 | Viewed by 3676

Abstract

Breynia cernua has been used as an alternative medicine for wounds, smallpox, cervical cancer, and breast cancer. This plant is a potential source of new plant-derived drugs to cure numerous diseases for its multiple therapeutic functions. An in vitro study revealed that the [...] Read more.

Breynia cernua has been used as an alternative medicine for wounds, smallpox, cervical cancer, and breast cancer. This plant is a potential source of new plant-derived drugs to cure numerous diseases for its multiple therapeutic functions. An in vitro study revealed that the methanol extract of B. cernua (stem) exhibits antioxidant activity according to DPPH and SOD methods, with IC₅₀ values of 33 and 8.13 ppm, respectively. The extract also exerts antibacterial activity against Staphylococcus aureus with minimum bactericidal concentration of 1875 ppm. Further analysis revealed that the extract with a concentration of 1–2 ppm protects erythrocytes from the ring formation stage of Plasmodium falciparum, while the extract with a concentration of 1600 ppm induced apoptosis in the MCF-7 breast cancer cell line. GC–MS analysis showed 45 bioactive compounds consisting of cyclic, alkyl halide, organosulfur, and organoarsenic compounds. Virtual screening via a blind docking approach was conducted to analyze the binding affinity of each metabolite against various target proteins. The results unveiled that two compounds, namely, N-[β-hydroxy-β-[4-[1-adamantyl-6,8-dichloro]quinolyl]ethyl]piperidine and 1,3-phenylene, bis(3-phenylpropenoate), demonstrated the best binding score toward four tested proteins with a binding affinity varying from −8.3 to −10.8 kcal/mol. Site-specific docking analysis showed that the two compounds showed similar binding energy with native ligands. This finding indicated that the two phenolic compounds could be novel antioxidant, antibacterial, antiplasmodial, and anticancer drugs. A thorough analysis by monitoring drug likeness and pharmacokinetics revealed that almost all the identified compounds can be considered as drugs, and they have good solubility, oral bioavailability, and synthetic accessibility. Altogether, the in vitro and in silico analysis suggested that the extract of B. cernua (stem) contains various compounds that might be correlated with its bioactivities. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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14 pages, 2421 KiB

Open AccessArticle

Anti-Inflammatory Activity of Compounds Derived from Vitex rotundifolia

by DucDat Le, Sanghee Han, Kyung Hyun Min and Mina Lee

Metabolites 2023, 13(2), 249; https://doi.org/10.3390/metabo13020249 - 9 Feb 2023

Cited by 3 | Viewed by 1837

Abstract

The objective of this study is to describe the separation and identification of one new phenolic and 19 known compounds from Vitex rotundifolia. Their structures were determined based on spectroscopic (NMR, CD, and MS) data analysis or Mosher’s method, and were compared [...] Read more.

The objective of this study is to describe the separation and identification of one new phenolic and 19 known compounds from Vitex rotundifolia. Their structures were determined based on spectroscopic (NMR, CD, and MS) data analysis or Mosher’s method, and were compared with those reported in the literature. These isolates were then evaluated for their anti-inflammatory and antioxidant activities based on the inhibition of nitric oxide (NO) and interleukin (IL)-8 production in lipopolysaccharide (LPS)-stimulated cells (RAW264.7 and HT-29) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, respectively. In the NO assay, compounds 12–14 showed strong inhibition with compounds 10 and 15 displaying significant inhibition. In the IL-8 assay, compounds 8, 9, 13, 14, 19, and 20 exhibited potential to inhibit IL-8 production and other compounds displayed moderate inhibition. An in silico docking approach also revealed strong binding affinities for protein–ligand complexes of these active compounds against IL-8 production. The docking results were correlated with the experimental data of the IL-8 assay. Thus, these active compounds should be considered as candidates for further in vivo studies. This study implies the potential of new and active chemicals isolated from V. rotundifolia and provides evidence to support the development of active fractions and constituents into functional products targeting inflammatory diseases the future. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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18 pages, 1078 KiB

Open AccessArticle

In the Beginning Was the Bud: Phytochemicals from Olive (Olea europaea L.) Vegetative Buds and Their Biological Properties

by Marijana Popović, Franko Burčul, Maja Veršić Bratinčević, Nikolina Režić Mužinić, Danijela Skroza, Roberta Frleta Matas, Marija Nazlić, Tonka Ninčević Runjić, Maja Jukić Špika, Ana Bego, Valerija Dunkić and Elda Vitanović

Metabolites 2023, 13(2), 237; https://doi.org/10.3390/metabo13020237 - 5 Feb 2023

Cited by 4 | Viewed by 2075

Abstract

Even though Olea europaea L. is one of the most important and well-studied crops in the world, embryonic parts of the plants remain largely understudied. In this study, comprehensive phytochemical profiling of olive vegetative buds of two Croatian cultivars, Lastovka and Oblica, [...] Read more.

Even though Olea europaea L. is one of the most important and well-studied crops in the world, embryonic parts of the plants remain largely understudied. In this study, comprehensive phytochemical profiling of olive vegetative buds of two Croatian cultivars, Lastovka and Oblica, was performed with an analysis of essential oils and methanol extracts as well as biological activities (antioxidant, antimicrobial, and cytotoxic activities). A total of 113 different volatiles were identified in essential oils with hydrocarbons accounting for up to 60.30% and (Z)-3-heptadecene being the most abundant compound. Oleacein, oleuropein, and 3-hydroxytyrosol had the highest concentrations of all phenolics in the bud extracts. Other major compounds belong to the chemical classes of sugars, fatty acids, and triterpenoid acids. Antioxidant, antimicrobial, and cytotoxic activities were determined for both cultivars. Apart from antioxidant activity, essential oils had a weak overall biological effect. The extract from cultivar Lastovka showed much better antioxidant activity than both isolates with both methods (with an oxygen radical absorbance capacity value of 1835.42 μM TE/g and DPPH IC₅₀ of 0.274 mg/mL), as well as antimicrobial activity with the best results against Listeria monocytogenes. The human breast adenocarcinoma MDA-MB-231 cell line showed the best response for cultivar Lastovka bud extract (IC₅₀ = 150 μg/mL) among three human cancer cell lines tested. These results demonstrate great chemical and biological potential that is hidden in olive buds and the need to increase research in the area of embryonic parts of plants. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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17 pages, 3532 KiB

Open AccessArticle

Characterization of Peptaibols Produced by a Marine Strain of the Fungus Trichoderma endophyticum via Mass Spectrometry, Genome Mining and Phylogeny-Based Prediction

by Gleucinei S. Castro, Thiago F. Sousa, Gilvan F. da Silva, Rita C. N. Pedroso, Kelly S. Menezes, Marcos A. Soares, Gustavo M. Dias, Aline O. Santos, Michel E. B. Yamagishi, Jéssica V. Faria, Ana H. Januário and Hector H. F. Koolen

Metabolites 2023, 13(2), 221; https://doi.org/10.3390/metabo13020221 - 3 Feb 2023

Cited by 8 | Viewed by 2985

Abstract

Trichoderma is recognized as a prolific producer of nonribosomal peptides (NRPs) known as peptaibols, which have remarkable biological properties, such as antimicrobial and anticancer activities, as well as the ability to promote systemic resistance in plants against pathogens. In this study, the sequencing [...] Read more.

Trichoderma is recognized as a prolific producer of nonribosomal peptides (NRPs) known as peptaibols, which have remarkable biological properties, such as antimicrobial and anticancer activities, as well as the ability to promote systemic resistance in plants against pathogens. In this study, the sequencing of 11-, 14- and 15-res peptaibols produced by a marine strain of Trichoderma isolated from the ascidian Botrylloides giganteus was performed via liquid chromatography coupled to high-resolution tandem mass spectrometry (LC-MS/MS). Identification, based on multilocus phylogeny, revealed that our isolate belongs to the species T. endophyticum, which has never been reported in marine environments. Through genome sequencing and genome mining, 53 biosynthetic gene clusters (BGCs) were identified as being related to bioactive natural products, including two NRP-synthetases: one responsible for the biosynthesis of 11- and 14-res peptaibols, and another for the biosynthesis of 15-res. Substrate prediction, based on phylogeny of the adenylation domains in combination with molecular networking, permitted extensive annotation of the mass spectra related to two new series of 15-res peptaibols, which are referred to herein as “endophytins”. The analyses of synteny revealed that the origin of the 15-module peptaibol synthetase is related to 18, 19 and 20-module peptaibol synthetases, and suggests that the loss of modules may be a mechanism used by Trichoderma species for peptaibol diversification. This study demonstrates the importance of combining genome mining techniques, mass spectrometry analysis and molecular networks for the discovery of new natural products. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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19 pages, 2524 KiB

Open AccessArticle

Metabolite Profiling of Premium Civet Luwak Bio-Transformed Coffee Compared with Conventional Coffee Types, as Analyzed Using Chemometric Tools

by Mohamed A. Farag, Tarik A. Mohamed, Enas A. El-Hawary and Amr Abdelwareth

Metabolites 2023, 13(2), 173; https://doi.org/10.3390/metabo13020173 - 24 Jan 2023

Cited by 7 | Viewed by 3315

Abstract

Luwak (civet) coffee is one of the most precious and exotic coffee commodities in the world. It has garnered an increasing reputation as the rarest and most expensive coffee, with an annual production. Many targeted analytical techniques have been reported for the discrimination [...] Read more.

Luwak (civet) coffee is one of the most precious and exotic coffee commodities in the world. It has garnered an increasing reputation as the rarest and most expensive coffee, with an annual production. Many targeted analytical techniques have been reported for the discrimination of specialty coffee commodities, such as Luwak coffee, from other ordinary coffee. This study presents the first comparative metabolomics approach for Luwak coffee analysis compared to other coffee products, targeting secondary and aroma metabolites using nuclear magnetic resonance (NMR), gas chromatography (GC), or liquid chromatography (LC) coupled with mass spectrometry (MS). Chemometric modeling of these datasets showed significant classification among all samples and aided in identifying potential novel markers for Luwak coffee from other coffee samples. Markers have indicated that C. arabica was the source of Luwak coffee, with several new markers being identified, including kahweol, chlorogenic acid lactones, and elaidic acid. Aroma profiling using solid-phase micro-extraction (SPME) coupled with GC/MS revealed higher levels of guaiacol derivatives, pyrazines, and furans in roasted Luwak coffee compared with roasted C. arabica. Quantification of the major metabolites was attempted using NMR for Luwak coffee to enable future standardization. Lower levels of alkaloids (caffeine 2.85 µg/mg, trigonelline 0.14 µg/mg, and xanthine 0.03 µg/mg) were detected, compared with C. arabica. Other metabolites that were quantified in civet coffee included kahweol and difurfuryl ether at 1.37 and 0.15 µg/mg, respectively. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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21 pages, 3321 KiB

Open AccessArticle

Chemical Composition, Biomolecular Analysis, and Nuclear Magnetic Resonance Spectroscopic Fingerprinting of Posidonia oceanica and Ascophyllum nodosum Extracts

by Angelica Bruno, Aldrik H. Velders, Alessandro Biasone, Mario Li Vigni, Donato Mondelli and Teodoro Miano

Metabolites 2023, 13(2), 170; https://doi.org/10.3390/metabo13020170 - 24 Jan 2023

Cited by 6 | Viewed by 3340

Abstract

A detailed analysis of the elemental and molecular composition of Posidonia oceanica (PO) and Ascophyllum nodosum (AN) is presented. In particular, an in-depth study of the molecular identification via NMR spectroscopy of aqueous and organic extracts of PO and AN was carried out, [...] Read more.

A detailed analysis of the elemental and molecular composition of Posidonia oceanica (PO) and Ascophyllum nodosum (AN) is presented. In particular, an in-depth study of the molecular identification via NMR spectroscopy of aqueous and organic extracts of PO and AN was carried out, exploiting 2D COSY and pseudo-2D DOSY data to aid in the assignment of peaks in complex 1D proton NMR spectra. Many metabolites were identified, such as carbohydrates, amino acids, organic acids, fatty acids, and polyphenols, with NMR complementing the characterization of the two species by standard elemental analysis, HPLC analysis, and colorimetric testing. For PO, different parts of the live plant (roots, rhizomes, and leaves) were analysed, as well as the residues of the dead plant which typically deposit along the coasts. The combination of the various studies made it possible to recognize bioactive compounds naturally present in the two plant species and, in particular, in the PO residues, opening the door for their possible recycling and use in, for example, fertilizer. Furthermore, NMR is proven to be a powerful tool for the metabolomic study of plant species as it allows for the direct identification of specific biomarkers as well as providing a molecular fingerprint of the plant variety. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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45 pages, 20132 KiB

Open AccessArticle

Molecular and Biological Investigation of Isolated Marine Fungal Metabolites as Anticancer Agents: A Multi-Target Approach

by Hanin A. Bogari, Sameh S. Elhady, Khaled M. Darwish, Mohamed S. Refaey, Radi A. Mohamed, Reda F. A. Abdelhameed, Ahmad J. Almalki, Mohammed M. Aldurdunji, Manar O. Lashkar, Samah O. Alshehri, Rania T. Malatani, Koji Yamada and Amgad I. M. Khedr

Metabolites 2023, 13(2), 162; https://doi.org/10.3390/metabo13020162 - 21 Jan 2023

Cited by 4 | Viewed by 2359

Abstract

Cancer is the leading cause of death globally, with an increasing number of cases being annually reported. Nature-derived metabolites have been widely studied for their potential programmed necrosis, cytotoxicity, and anti-proliferation leading to enrichment for the modern medicine, particularly within the last couple [...] Read more.

Cancer is the leading cause of death globally, with an increasing number of cases being annually reported. Nature-derived metabolites have been widely studied for their potential programmed necrosis, cytotoxicity, and anti-proliferation leading to enrichment for the modern medicine, particularly within the last couple of decades. At a more rapid pace, the concept of multi-target agents has evolved from being an innovative approach into a regular drug development procedure for hampering the multi-fashioned pathophysiology and high-resistance nature of cancer cells. With the advent of the Red Sea Penicillium chrysogenum strain S003-isolated indole-based alkaloids, we thoroughly investigated the molecular aspects for three major metabolites: meleagrin (MEL), roquefortine C (ROC), and isoroquefortine C (ISO) against three cancer-associated biological targets Cdc-25A, PTP-1B, and c-Met kinase. The study presented, for the first time, the detailed molecular insights and near-physiological affinity for these marine indole alkaloids against the assign targets through molecular docking-coupled all-atom dynamic simulation analysis. Findings highlighted the superiority of MEL’s binding affinity/stability being quite in concordance with the in vitro anticancer activity profile conducted via sulforhodamine B bioassay on different cancerous cell lines reaching down to low micromolar or even nanomolar potencies. The advent of lengthy structural topologies via the metabolites’ extended tetracyclic cores and aromatic imidazole arm permitted multi-pocket accommodation addressing the selectivity concerns. Additionally, the presence decorating polar functionalities on the core hydrophobic tetracyclic ring contributed compound’s pharmacodynamic preferentiality. Introducing ionizable functionality with more lipophilic characters was highlighted to improve binding affinities which was also in concordance with the conducted drug-likeness/pharmacokinetic profiling for obtaining a balanced pharmacokinetic/dynamic profile. Our study adds to the knowledge regarding drug development and optimization of marine-isolated indole-based alkaloids for future iterative synthesis and pre-clinical investigations as multi-target anticancer agents. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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19 pages, 2207 KiB

Open AccessArticle

Anti-Heliobacter pylori and Anti-Inflammatory Potential of Salvia officinalis Metabolites: In Vitro and In Silico Studies

by Hatun A. Alomar, Wafaa M. Elkady, Marwa M. Abdel-Aziz, Taghreed A. Ibrahim and Noha Fathallah

Metabolites 2023, 13(1), 136; https://doi.org/10.3390/metabo13010136 - 16 Jan 2023

Cited by 3 | Viewed by 2979

Abstract

Due to its rising antibiotic resistance and associated inflammations, Helicobacter pylori poses a challenge in modern medicine. Salvia officinalis, a member of the Lamiaceae family, is a promising medicinal herb. In this regard, a phytochemical screening followed by GC-MS and LC-MS was [...] Read more.

Due to its rising antibiotic resistance and associated inflammations, Helicobacter pylori poses a challenge in modern medicine. Salvia officinalis, a member of the Lamiaceae family, is a promising medicinal herb. In this regard, a phytochemical screening followed by GC-MS and LC-MS was done to evaluate the chemical profile of the total ethanolic extract (TES) and the essential oil, respectively. The anti-H. pylori and the anti-inflammatory activities were evaluated by a micro-well dilution technique and COX-2 inhibition assay. Potential anti-H. pylori inhibitors were determined by an in silico study. The results revealed that the main metabolites were flavonoids, sterols, volatile oil, saponins, and carbohydrates. The LC-MS negative ionization mode demonstrated 12 compounds, while GC-MS showed 21 compounds. Carnosic acid (37.66%), epirosmanol (20.65%), carnosol1 (3.3%), and 12-O-methyl carnosol (6.15%) were predominated, while eucalyptol (50.04%) and camphor (17.75%) were dominant in LC-MS and GC-MS, respectively. TES exhibited the strongest anti-H. pylori activity (3.9 µg/mL) asymptotic to clarithromycin (0.43 µg/mL), followed by the oil (15.63 µg/mL). Carnosic acid has the best-fitting energy to inhibit H. pylori (−46.6769 Kcal/mol). TES showed the highest reduction in Cox-2 expression approaching celecoxib with IC₅₀ = 1.7 ± 0.27 µg/mL, followed by the oil with IC₅₀ = 5.3 ± 0.62 µg/mL. Our findings suggest that S. officinalis metabolites with anti-inflammatory capabilities could be useful in H. pylori management. Further in vivo studies are required to evaluate and assess its promising activity. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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20 pages, 2979 KiB

Open AccessArticle

Investigation of Chemical Composition and Biological Activities of Ajuga pyramidalis—Isolation of Iridoids and Phenylethanoid Glycosides

by Anthonin Gori, Benjamin Boucherle, Aurélien Rey, Maxime Rome, Caroline Barette, Emmanuelle Soleilhac, Christian Philouze, Marie-Odile Fauvarque, Nicola Fuzzati and Marine Peuchmaur

Metabolites 2023, 13(1), 128; https://doi.org/10.3390/metabo13010128 - 14 Jan 2023

Cited by 3 | Viewed by 1984

Abstract

Despite several studies on the Ajuga L. genus, the chemical composition of Ajuga pyramidalis, an alpine endemic species, is still largely unknown. The purpose of this study was to therefore deeper describe it, particularly from the phytochemistry and bioactivity perspectives. In that [...] Read more.

Despite several studies on the Ajuga L. genus, the chemical composition of Ajuga pyramidalis, an alpine endemic species, is still largely unknown. The purpose of this study was to therefore deeper describe it, particularly from the phytochemistry and bioactivity perspectives. In that respect, A. pyramidalis was investigated and 95% of the extracted mass of the plant was characterized by chromatography and mass spectrometry. Apart from the already determined chemical compounds, namely, harpagide and 8-O-acetylharpagide, two iridoids, and neoajugapyrin A, a neo-clerodane diterpene, and three polyphenols (echinacoside, verbascoside and teupoloside) were identified for the first time in A. pyramidalis. Incidentally, the first RX structure of a harpagoside derivative is also described in this paper. The extracts and isolated compounds were then evaluated for various biochemical or biological activities; notably a targeted action on the renewal of the epidermis was highlighted with potential applications in the cosmetic field for anti-aging. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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19 pages, 5459 KiB

Open AccessArticle

A Study of the Interaction between Xanthine Oxidase and Its Inhibitors from Chrysanthemum morifolium Using Computational Simulation and Multispectroscopic Methods

by Sze Ping Wee, Khye Er Loh, Kok Wai Lam and Intan Safinar Ismail

Metabolites 2023, 13(1), 113; https://doi.org/10.3390/metabo13010113 - 9 Jan 2023

Cited by 9 | Viewed by 1867

Abstract

The current therapeutic approach for gout is through the inhibition of the xanthine oxidase (XO) enzyme. Allopurinol, a clinically used XO inhibitor, causes many side effects. This study aimed to investigate the interaction between XO and inhibitors identified from Chrysanthemum morifolium by using [...] Read more.

The current therapeutic approach for gout is through the inhibition of the xanthine oxidase (XO) enzyme. Allopurinol, a clinically used XO inhibitor, causes many side effects. This study aimed to investigate the interaction between XO and inhibitors identified from Chrysanthemum morifolium by using computational simulation and multispectroscopic methods. The crude extract, petroleum ether, ethyl acetate (EtOAc), and residual fractions were subjected to an XO inhibitory assay and ¹H NMR analysis. The EtOAc fraction was shown to be strongly correlated to the XO inhibitory activity by using PLS biplot regression analysis. Kaempferol, apigenin, homovanillic acid, and trans-cinnamic acid were suggested to contribute to the XO inhibitory activity. Molecular docking showed that kaempferol and apigenin bound to the active site of XO with their benzopyran moiety sandwiched between Phe914 and Phe1009, interacting with Thr1010 and Arg880 by hydrogen bonding. Kaempferol showed the lowest binding energy in molecular dynamic simulation. The residues that contributed to the binding energy were Glu802, Arg880, Phe 914, and Phe 1009. A fluorescence quenching study showed a combination of static and dynamic quenching for all four inhibitors binding to XO. Circular dichroism spectroscopy revealed that there was no major change in XO conformation after binding with each inhibitor. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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14 pages, 2680 KiB

Open AccessFeature PaperArticle

The Combined Effect of Licorice Extract and Bone Marrow Mesenchymal Stem Cells on Cisplatin-Induced Hepatocellular Damage in Rats

by Maysa A. Mobasher, Eman Ibrahim Ahmed, Nora Y. Hakami, Mousa O. Germoush, Nabil S Awad and Dina M. Khodeer

Metabolites 2023, 13(1), 94; https://doi.org/10.3390/metabo13010094 - 6 Jan 2023

Cited by 4 | Viewed by 2316

Abstract

Drug-induced liver damage is a life-threatening disorder, and one major form of it is the hepatotoxicity induced by the drug cisplatin. In folk medicine, Licorice (Glycyrrhiza glabra (is used for detoxification and is believed to be a potent antioxidant. Currently, the magically [...] Read more.

Drug-induced liver damage is a life-threatening disorder, and one major form of it is the hepatotoxicity induced by the drug cisplatin. In folk medicine, Licorice (Glycyrrhiza glabra (is used for detoxification and is believed to be a potent antioxidant. Currently, the magically self-renewable potential of bone marrow mesenchymal stem cells (BM-MSCs) has prompted us to explore their hepatoregenerative capability. The impact of G. glabra extract (GGE) and BM-MSCs alone and, in combination, on protecting against hepatotoxicity was tested on cisplatin-induced liver injury in rats. Hepatic damage, as revealed by liver histopathology and increased levels of serum aspartate aminotransferase (AST), alanine aminotransferase (ALT), alkaline phosphatase (ALP), and malondialdehyde (MDA), was elevated in rats by received 7 mg/kg of cisplatin intraperitoneally. The combination of GGE and BM-MSCs returned the enzyme levels to near the normal range. It also improved levels of liver superoxide dismutase (SOD) and glutathione (GSH) and reduced MDA levels. Additionally, it was found that when GGE and BM-MSCs were used together, they significantly downregulated caspase9 (Casp9), nuclear factor kappa-light-chain-enhancer of activated B cells (NF-kB), and interleukin-1β (IL-1β), which are involved in severe proinflammatory and apoptotic signaling cascades in the liver. Moreover, combining GGE and BM-MSCs led to the normal result of hepatocytes in several examined liver histological sections. Therefore, our findings suggest that GGE may have protective effects against oxidative liver damage and the promising regenerative potential of BM-MSCs. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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25 pages, 6124 KiB

Open AccessArticle

Identification of Potential Leishmania N-Myristoyltransferase Inhibitors from Withania somnifera (L.) Dunal: A Molecular Docking and Molecular Dynamics Investigation

by Mohamed A. A. Orabi, Mohammed Merae Alshahrani, Ahmed M. Sayed, Mohamed E. Abouelela, Khaled A. Shaaban and El-Shaymaa Abdel-Sattar

Metabolites 2023, 13(1), 93; https://doi.org/10.3390/metabo13010093 - 6 Jan 2023

Cited by 4 | Viewed by 3336

Abstract

Leishmaniasis is a group of infectious diseases caused by Leishmania protozoa. The ineffectiveness, high toxicity, and/or parasite resistance of the currently available antileishmanial drugs has created an urgent need for safe and effective leishmaniasis treatment. Currently, the molecular-docking technique is used to predict [...] Read more.

Leishmaniasis is a group of infectious diseases caused by Leishmania protozoa. The ineffectiveness, high toxicity, and/or parasite resistance of the currently available antileishmanial drugs has created an urgent need for safe and effective leishmaniasis treatment. Currently, the molecular-docking technique is used to predict the proper conformations of small-molecule ligands and the strength of the contact between a protein and a ligand, and the majority of research for the development of new drugs is centered on this type of prediction. Leishmania N-myristoyltransferase (NMT) has been shown to be a reliable therapeutic target for investigating new anti-leishmanial molecules through this kind of virtual screening. Natural products provide an incredible source of affordable chemical scaffolds that serve in the development of effective drugs. Withania somnifera leaves, roots, and fruits have been shown to contain withanolide and other phytomolecules that are efficient anti-protozoal agents against Malaria, Trypanosoma, and Leishmania spp. Through a review of previously reported compounds from W. somnifera-afforded 35 alkaloid, phenolic, and steroid compounds and 132 withanolides/derivatives, typical of the Withania genus. These compounds were subjected to molecular docking screening and molecular dynamics against L. major NMT. Calycopteretin-3-rutinoside and withanoside IX showed the highest affinity and binding stability to L. major NMT, implying that these compounds could be used as antileishmanial drugs and/or as a scaffold for the design of related parasite NMT inhibitors with markedly enhanced binding affinity. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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19 pages, 2166 KiB

Open AccessArticle

How Does Allium Leafy Parts Metabolome Differ in Context to Edible or Inedible Taxa? Case Study in Seven Allium Species as Analyzed Using MS-Based Metabolomics

by Mostafa H. Baky, Samir N. Shamma, Mohamed R. Khalifa and Mohamed A. Farag

Metabolites 2023, 13(1), 18; https://doi.org/10.3390/metabo13010018 - 22 Dec 2022

Cited by 11 | Viewed by 2482

Abstract

Genus Allium (F. Amaryllidaceae) includes a wide variety of edible foods widely consumed for their nutritive as well as health benefits. Seven Allium species, viz., chives, Egyptian leek, French leek, red garlic, white garlic, red onion, and white onion aerial parts were assessed [...] Read more.

Genus Allium (F. Amaryllidaceae) includes a wide variety of edible foods widely consumed for their nutritive as well as health benefits. Seven Allium species, viz., chives, Egyptian leek, French leek, red garlic, white garlic, red onion, and white onion aerial parts were assessed for metabolome heterogeneity targeting both aroma and nutrients phytochemicals. A headspace solid-phase microextraction (HS-SPME) and gas chromatography–mass spectrometry (GC–MS) were employed. Results revealed extensive variation in volatiles and nutrients profile among the seven Allium species represented by a total of 77 nutrients and 148 volatiles. Among edible Allium species, French leek encompassed high levels of nutrients, viz., sugars, fatty acids/esters, organic acids, and amino acids, compared to Egyptian leek. Sulfur aroma compounds appeared as the most discriminatory among Allium, taxa accounting for its distinct flavor. Furthermore, chemometric analysis of both datasets showed clear discrimination of the seven Allium species according to several key novel markers. This study provides the first comparative approach between edible and inedible aerial leafy parts of Allium species providing novel insight into their use as functional foods based on such holistic profiling. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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19 pages, 5158 KiB

Open AccessArticle

Mangosteen Metabolites as Promising Alpha-Amylase Inhibitor Candidates: In Silico and In Vitro Evaluations

by Abdelsattar M. Omar, Dana F. AlKharboush, Khadijah A. Mohammad, Gamal A. Mohamed, Hossam M. Abdallah and Sabrin R. M. Ibrahim

Metabolites 2022, 12(12), 1229; https://doi.org/10.3390/metabo12121229 - 7 Dec 2022

Cited by 8 | Viewed by 2494

Abstract

Diabetes is a chronic metabolic disorder characterized by raised glucose levels in the blood, resulting in grave damage over time to various body organs, including the nerves, heart, kidneys, eyes, and blood vessels. One of its therapeutic treatment approaches involves the inhibition of [...] Read more.

Diabetes is a chronic metabolic disorder characterized by raised glucose levels in the blood, resulting in grave damage over time to various body organs, including the nerves, heart, kidneys, eyes, and blood vessels. One of its therapeutic treatment approaches involves the inhibition of enzymes accountable for carbohydrate digestion and absorption. The present work is aimed at evaluating the potential of some reported metabolites from Garcinia mangostana (mangosteen, Guttiferae) as alpha-amylase inhibitors. Forty compounds were assessed for their capacity to inhibit alpha-amylase using in silico studies as well as in vitro assays. Molecular docking was carried out to analyze their binding capacities in the 3D structure of alpha-amylase (PDB ID: 4GQR). Among the tested compounds, 6-O-β-D-glucopyranosyl-2,4,6,3′,4′,6′-hexahydroxybenzophenone (8), aromadendrin-8-C-glucoside (5), epicatechin (6), rhodanthenone (4), and garcixanthone D (40) had a high XP G.score and a Glide G.score of −12.425, −11.855, −11.135, and −11.048 Kcal/mol, respectively. Compound 8 possessed the XP and Glide docking score of −12.425 Kcal/mol compared to the reference compounds myricetin and acarbose which had an XP and Glide docking score of −12.319 and 11.201 Kcal/mol, respectively. It interacted through hydrogen bond formations between its hydroxyl groups and the residues His 101, Asp 197, Glu 233, Asp 300, and His 305, in addition to water bridges and hydrophobic interactions. Molecular mechanics-generalized born surface area (MM-GBSA) was used to calculate the binding free energy and molecular dynamic studies that indicated the stability of the alpha-amylase-compound 8 complex during the 100 ns simulation in comparison with myricetin- and acarbose-alpha-amylase complexes. Additionally, the in vitro alpha-amylase inhibition assay findings validated the in silico study’s findings. This could further validate the potential of G. mangostana as a candidate for diabetes management. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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Review

Jump to: Research

16 pages, 1101 KiB

Open AccessReview

Centella asiatica and Its Metabolite Asiatic Acid: Wound Healing Effects and Therapeutic Potential

by Lúcio Ricardo Leite Diniz, Leonardo Luiz Calado, Allana Brunna Sucupira Duarte and Damião Pergentino de Sousa

Metabolites 2023, 13(2), 276; https://doi.org/10.3390/metabo13020276 - 14 Feb 2023

Cited by 46 | Viewed by 11419

Abstract

An intense effort has been focused on new therapeutic approaches and the development of technologies for more efficient and rapid wound healing. The research for plants used for long time in traditional medicine in the treatment of wound has become a promising strategy [...] Read more.

An intense effort has been focused on new therapeutic approaches and the development of technologies for more efficient and rapid wound healing. The research for plants used for long time in traditional medicine in the treatment of wound has become a promising strategy to obtain drugs therapeutically useful in the acute and chronic wound management. In this context, Centella asiatica (Apiaceae) has been used to treat a variety of skin diseases, such as leprosy, lupus, varicose ulcers, eczema and psoriasis, in Asiatic traditional medicine for thousands of years. Studies have shown that Centella asiatica extracts (CAE) display activity in tissue regeneration, cell migration and wound repair process by promoting fibroblast proliferation and collagen synthesis. Preliminary findings have shown that the asiatic acid is one of the main active constituents of C. asiatica, directly associated with its healing activity. Thus, this study discusses aspects of the effects of Centella asiatica and its active component, asiatic acid, in different stages of the healing process of cutaneous wounds, including phytochemical and antimicrobial aspects that contribute to its therapeutic potential. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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29 pages, 6719 KiB

Open AccessReview

Callyspongia spp.: Secondary Metabolites, Pharmacological Activities, and Mechanisms

by Yuni Elsa Hadisaputri, Annida Adha Nurhaniefah, Sendi Sukmara, Ade Zuhrotun, Rini Hendriani and Iyan Sopyan

Metabolites 2023, 13(2), 217; https://doi.org/10.3390/metabo13020217 - 1 Feb 2023

Cited by 3 | Viewed by 2438

Abstract

One of the most widespread biotas in the sea is the sponge. Callyspongia is a sponge genus found in the seas, making it easily available. In this review, the pharmacological activity and mechanism of action of the secondary metabolites of Callyspongia spp. are [...] Read more.

One of the most widespread biotas in the sea is the sponge. Callyspongia is a sponge genus found in the seas, making it easily available. In this review, the pharmacological activity and mechanism of action of the secondary metabolites of Callyspongia spp. are addressed, which may lead to the development of new drugs and targeted therapeutic approaches. Several scientific databases, such as Google Scholar, PubMed, ResearchGate, Science Direct, Springer Link, and Wiley Online Library, were mined to obtain relevant information. In the 41 articles reviewed, Callyspongia spp. was reported to possess pharmacological activities such as cytotoxicity against cancer cell lines (36%), antifungal (10%), anti-inflammatory (10%), immunomodulatory (10%), antidiabetic and antiobesity (6%), antimicrobial (8%), antioxidant (4%), antineurodegenerative (4%), antihypercholesterolemic (2%), antihypertensive (2%), antiparasitic (2%), antiallergic (2%), antiviral (2%), antiosteoporotic (2%), and antituberculosis (2%) activities. Of these, the antioxidant, antituberculosis, and anti-inflammatory activities of Callyspongia extract were weaker compared with that of the control drugs; however, other activities, particularly cytotoxicity, show promise, and the compounds responsible may be developed into new drugs. Full article

(This article belongs to the Special Issue Extraction, Characterization, Chemical Composition and Biological Activity of Natural Metabolites)

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