Molecules

Research

Jump to: Review

17 pages, 1986 KiB

Open AccessArticle

Determination of Some Isoquinoline Alkaloids in Extracts Obtained from Selected Plants of the Ranunculaceae, Papaveraceae and Fumarioideae Families by Liquid Chromatography and In Vitro and In Vivo Investigations of Their Cytotoxic Activity

by Justyna Misiurek, Tomasz Plech, Barbara Kaproń, Anna Makuch-Kocka, Małgorzata Szultka-Młyńska, Bogusław Buszewski and Anna Petruczynik

Molecules 2023, 28(8), 3503; https://doi.org/10.3390/molecules28083503 - 16 Apr 2023

Cited by 6 | Viewed by 2333

Abstract

Alkaloids are heterocyclic bases with widespread occurrence in nature. Plants are rich and easily accessible sources of them. Most isoquinoline alkaloids have cytotoxic activity for different types of cancer, including malignant melanoma, the most aggressive type of skin cancer. The morbidity of melanoma [...] Read more.

Alkaloids are heterocyclic bases with widespread occurrence in nature. Plants are rich and easily accessible sources of them. Most isoquinoline alkaloids have cytotoxic activity for different types of cancer, including malignant melanoma, the most aggressive type of skin cancer. The morbidity of melanoma has increased worldwide every year. For that reason, developing new candidates for anti–melanoma drugs is highly needed. The aim of this study was to investigate the alkaloid compositions of plant extracts obtained from Macleaya cordata root, stem and leaves, Pseudofumaria lutea root and herb, Lamprocapnos spectabilis root and herb, Fumaria officinalis whole plant, Thalictrum foetidum root and herb, and Meconopsis cambrica root and herb by HPLC-DAD and LC-MS/MS. For determination of cytotoxic properties, human malignant melanoma cell line A375, human Caucasian malignant melanoma cell line G-361, and human malignant melanoma cell line SK-MEL-3 were exposed in vitro to the tested plant extracts. Based on the in vitro experiments, Lamprocapnos spectabilis herb extract was selected for further, in vivo research. The toxicity of the extract obtained from Lamprocapnos spectabilis herb was tested using an animal zebrafish model in the fish embryo toxicity test (FET) for determination of the LC₅₀ value and non-toxic doses. Determination of the influence of the investigated extract on the number of cancer cells in a living organism was performed using a zebrafish xenograft model. Determination of the contents of selected alkaloids in different plant extracts was performed using high performance liquid chromatography (HPLC) in a reverse-phase system (RP) on a Polar RP column with a mobile phase containing acetonitrile, water and ionic liquid. The presence of these alkaloids in plant extracts was confirmed by LC-MS/MS. Preliminary cytotoxic activity of all prepared plant extracts and selected alkaloid standards was examined using human skin cancer cell lines A375, G-361, and SK-MEL-3. The cytotoxicity of the investigated extract was determined in vitro by cell viability assays (MTT). For in vivo determination of investigated extract cytotoxicity, a Danio rerio larvae xenograft model was used. All investigated plant extracts in in vitro experiments exhibited high cytotoxic activity against the tested cancer cell lines. The results obtained using the Danio rerio larvae xenograft model confirmed the anticancer activity of the extract obtained from Lamprocapnos spectabilis herb. The conducted research provides a basis for future investigations of these plant extracts for potential use in the treatment of malignant melanoma. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

15 pages, 3267 KiB

Open AccessArticle

Antimicrobial Activity of Dihydroisocoumarin Isolated from Wadi Lajab Sediment-Derived Fungus Penicillium chrysogenum: In Vitro and In Silico Study

by Raha Orfali, Shagufta Perveen, Mohamed Fahad AlAjmI, Safina Ghaffar, Md Tabish Rehman, Abdullah R. AlanzI, Saja Bane Gamea and Mona Essa Khwayri

Molecules 2022, 27(11), 3630; https://doi.org/10.3390/molecules27113630 - 6 Jun 2022

Cited by 10 | Viewed by 2785

Abstract

Antibiotic resistance is considered a major health concern globally. It is a fact that the clinical need for new antibiotics was not achieved until now. One of the most commonly prescribed classes of antibiotics is β-Lactam antibiotics. However, most bacteria have developed resistance [...] Read more.

Antibiotic resistance is considered a major health concern globally. It is a fact that the clinical need for new antibiotics was not achieved until now. One of the most commonly prescribed classes of antibiotics is β-Lactam antibiotics. However, most bacteria have developed resistance against β-Lactams by producing enzymes β-Lactamase or penicillinase. The discovery of new β-Lactamase inhibitors as new antibiotics or antibiotic adjuvants is essential to avoid future catastrophic pandemics. In this study, five dihydroisocoumarin: 6-methoxy mellein (1); 5,6-dihydroxymellein (2); 6-hydroxymellein (3); 4-chloro-6-hydroxymellein (4) and 4-chloro-5,6-di-hydroxymellein (5) were isolated from Wadi Lajab sediment-derived fungus Penicillium chrysogenum, located 15 km northwest of Jazan, KSA. The elucidation of the chemical structures of the isolated compounds was performed by analysis of their NMR, MS. Compounds 1–5 were tested for antibacterial activities against Gram-positive and Gram-negative bacteria. All of the compounds exhibited selective antibacterial activity against Gram-positive bacteria Staphylococcus aureus and Bacillus licheniformis except compound 3. The chloro-dihydroisocoumarin derivative, compound 4, showed potential antimicrobial activities against all of the tested strains with the MIC value between 0.8–5.3 μg/mL followed by compound 5, which exhibited a moderate inhibitory effect. Molecular docking data showed good affinity with the isolated compounds to β-Lactamase enzymes of bacteria; NDM-1, CTX-M, OXA-48. This work provides an effective strategy for compounds to inhibit bacterial growth or overcome bacterial resistance. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

11 pages, 2067 KiB

Open AccessArticle

In Vitro and In Silico Anti-Acetylcholinesterase Activity from Macaranga tanarius and Syzygium jambos

by Mira Syahfriena Amir Rawa, Nurul Amira Nurul Azman, Suriani Mohamad, Toshihiko Nogawa and Habibah A. Wahab

Molecules 2022, 27(9), 2648; https://doi.org/10.3390/molecules27092648 - 20 Apr 2022

Cited by 9 | Viewed by 2875

Abstract

Macaranga tanarius (MT) and Syzygium jambos (SJ) are pharmacologically reported to have anti-oxidant, anti-inflammatory, and anti-diabetic effects, and can be neuroprotective agents. Our previous work revealed that MT and SJ exhibited 76.32% and 93.81% inhibition against acetylcholinesterase (AChE) at 50 μg/mL final concentration [...] Read more.

Macaranga tanarius (MT) and Syzygium jambos (SJ) are pharmacologically reported to have anti-oxidant, anti-inflammatory, and anti-diabetic effects, and can be neuroprotective agents. Our previous work revealed that MT and SJ exhibited 76.32% and 93.81% inhibition against acetylcholinesterase (AChE) at 50 μg/mL final concentration in their ethyl acetate and hexane fractions, respectively. This study was aimed to investigate the bioactive constituents of MT and SJ and their molecular mechanism toward AChE inhibition. Bioassay-guided isolation afforded prenylflavonoids 1–3 from MT and anacardic acid derivatives 4 and 5 from SJ that were confirmed by NMR and MS data. Compound 5 exerted the strongest anti-AChE potential (IC₅₀: 0.54 μM), followed by 1, 4, 3, and 2 (IC₅₀: 1.0, 2.4, 6.8, and 33 μM, respectively). In silico molecular docking revealed 5 formed stronger molecular interactions including three H-bonds than its derivative 4 based on the saturation of their alkyl chains. The addition of a five carbon-prenyl chain in 1 increased the number of binding interactions, justifying its greater activity than derivatives 2 and 3. This research reflects the first report of AChE inhibitors from these species, thereby adding pharmacological values to MT and SJ as potential remedies in neuroprotection. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Graphical abstract

11 pages, 3272 KiB

Open AccessArticle

In Vitro Evaluation of the Photoreactivity and Phototoxicity of Natural Polyphenol Antioxidants

by Brandon Aguiar, Helena Carmo, Jorge Garrido, José M. Sousa Lobo and Isabel F. Almeida

Molecules 2022, 27(1), 189; https://doi.org/10.3390/molecules27010189 - 29 Dec 2021

Cited by 7 | Viewed by 2803

Abstract

Polyphenols are a large family of natural compounds widely used in cosmetic products due to their antioxidant and anti-inflammatory beneficial properties and their ability to prevent UV radiation-induced oxidative stress. Since these compounds present chromophores and are applied directly to the skin, they [...] Read more.

Polyphenols are a large family of natural compounds widely used in cosmetic products due to their antioxidant and anti-inflammatory beneficial properties and their ability to prevent UV radiation-induced oxidative stress. Since these compounds present chromophores and are applied directly to the skin, they can react with sunlight and exert phototoxic effects. The available scientific information on the phototoxic potential of these natural compounds is scarce, and thus the aim of this study was to evaluate the photoreactivity and phototoxicity of five phenolic antioxidants with documented use in cosmetic products. A standard ROS assay was validated and applied to screen the photoreactivity of the natural phenolic antioxidants caffeic acid, ferulic acid, p-coumaric acid, 3,4-dihydroxyphenylacetic acid (DOPAC), and rutin. The phototoxicity potential was determined by using a human keratinocyte cell line (HaCaT), based on the 3T3 Neutral Red Uptake phototoxicity test. Although all studied phenolic antioxidants absorbed UV/Vis radiation in the range of 290 to 700 nm, only DOPAC was able to generate singlet oxygen. The generation of reactive oxygen species is an early-stage chemical reaction as part of the phototoxicity mechanism. Yet, none of the studied compounds decreased the viability of keratinocytes after irradiation, leading to the conclusion that they do not have phototoxic potential. The data obtained with this work suggests that these compounds are safe when incorporated in cosmetic products. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

14 pages, 1250 KiB

Open AccessArticle

Hepatoprotective Constituents of Total Dibenzocyclooctadiene Lignans from Schisandra chinensis Based on the Spectrum-Effect Relationship

by Lu-Lu Deng, Xu-Dong Xie, Jiang Li, Dao-Ping Wang, Xiao-Jiang Hao, Gang Chen and Shu-Zhen Mu

Molecules 2021, 26(21), 6554; https://doi.org/10.3390/molecules26216554 - 29 Oct 2021

Cited by 4 | Viewed by 2416

Abstract

To scientifically clarify the hepatoprotective constituents of Fructus Schizandrae chinensis, eleven batches samples of total dibenzocyclooctadiene lignans (TDL) from Schisandra chinensis were prepared by using the optimum extraction technique. Characteristic high-performance liquid chromatography (HPLC) chromatograms were obtained through HPLC analysis technology, and the [...] Read more.

To scientifically clarify the hepatoprotective constituents of Fructus Schizandrae chinensis, eleven batches samples of total dibenzocyclooctadiene lignans (TDL) from Schisandra chinensis were prepared by using the optimum extraction technique. Characteristic high-performance liquid chromatography (HPLC) chromatograms were obtained through HPLC analysis technology, and the hepatoprotective effects of the eleven batches of TDL were evaluated by MTT assay. Based on the chemical and biological activity results, the spectrum-effect relationship between the characteristic HPLC fingerprints and the hepatoprotective effect of TDL was established using Minitab 16.0 data analysis software. On the basis of the spectrum-effect relationship, thirteen compounds (1–13) were obtained from the TDL by chemical natural product chemical separation and purification technology, and their structures were identified on the basis of the spectral data and the literature. Based on these compounds, thirteen common peaks among the thirty-three chromatographic peaks in the above HPLC fingerprints were identified. Our findings showed that some components, including, schisandrin B (2), schisandrin A (3), and schisandrol B (7) had significant roles in promoting hepatoprotective activity. Preliminary verification of the spectrum-effect relationship of TDL from S. chinensis was carried out, and the results confirmed that the activity of a composite of these three key components in optimal ratios was better than that of any individual compound, which potentially confirmed the reliability of the spectrum-effect relationship and the synergistic effects of traditional Chinese medicine. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

15 pages, 3642 KiB

Open AccessArticle

Evaluation of Antioxidative Mechanisms In Vitro and Triterpenes Composition of Extracts from Silver Birch (Betula pendula Roth) and Black Birch (Betula obscura Kotula) Barks by FT-IR and HPLC-PDA

by Aleksandra Ostapiuk, Łukasz Kurach, Maciej Strzemski, Jacek Kurzepa and Anna Hordyjewska

Molecules 2021, 26(15), 4633; https://doi.org/10.3390/molecules26154633 - 30 Jul 2021

Cited by 12 | Viewed by 3077

Abstract

Silver birch, Betula pendula Roth, is one of the most common trees in Europe. Due to its content of many biologically active substances, it has long been used in medicine and cosmetics, unlike the rare black birch, Betula obscura Kotula. The aim of [...] Read more.

Silver birch, Betula pendula Roth, is one of the most common trees in Europe. Due to its content of many biologically active substances, it has long been used in medicine and cosmetics, unlike the rare black birch, Betula obscura Kotula. The aim of the study was therefore to compare the antioxidant properties of extracts from the inner and outer bark layers of both birch trees towards the L929 line treated with acetaldehyde. Based on the lactate dehydrogenase test and the MTT test, 10 and 25% concentrations of extracts were selected for the antioxidant evaluation. All extracts at tested concentrations reduced the production of hydrogen peroxide, superoxide anion radical, and 25% extract decreased malonic aldehyde formation in acetaldehyde-treated cells. The chemical composition of bark extracts was accessed by IR and HPLC-PDA methods and surprisingly, revealed a high content of betulin and lupeol in the inner bark extract of B. obscura. Furthermore, IR analysis revealed differences in the chemical composition of the outer bark between black and silver birch extracts, indicating that black birch may be a valuable source of numerous biologically active substances. Further experiments are required to evaluate their potential against neuroinflammation, cancer, viral infections, as well as their usefulness in cosmetology. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

22 pages, 6852 KiB

Open AccessArticle

Corneal Healing and Recovery of Ocular Crystallinity with a Dichloromethane Extract of Sedum dendroideum D.C. in a Novel Murine Model of Ocular Pterygium

by Luiselva Torrescano-De Labra, Enrique Jiménez-Ferrer, Brenda Hildeliza Camacho-Díaz, Gabriela Vargas-Villa, Manases González-Cortazar, Maribel Herrera-Ruiz, Sandra Victoria Ávila Reyes, Javier Solorza-Feria and Antonio Ruperto Jiménez-Aparicio

Molecules 2021, 26(15), 4502; https://doi.org/10.3390/molecules26154502 - 26 Jul 2021

Cited by 2 | Viewed by 2336

Abstract

Pterygium is a corneal alteration that can cause visual impairment, which has been traditionally treated with the sap of Sedum dendroideum D.C. The pharmacological effect of a dichloromethane extract of S. dendroideum was demonstrated and implemented in a pterygium model on the healing [...] Read more.

Pterygium is a corneal alteration that can cause visual impairment, which has been traditionally treated with the sap of Sedum dendroideum D.C. The pharmacological effect of a dichloromethane extract of S. dendroideum was demonstrated and implemented in a pterygium model on the healing process of corneal damage caused by phorbol esters. In mice of the ICR strain, a corneal lesion was caused by intravitreal injection of tetradecanoylphorbol acetate (TPA). The evolution of the corneal scarring process was monitored with vehicle, dexamethasone, and dichloromethane extract of S. dendroideum treatments by daily ophthalmic administration for fifteen days. The lesions were evaluated in situ with highlighted images of fluorescence of the lesions. Following treatment levels in eyeballs of IL-1α, TNF-α, and IL-10 cytokines were measured. The effective dose of TPA to produce a pterygium-like lesion was determined. The follow-up of the evolution of the scarring process allowed us to define that the treatment with S. dendroideum improved the experimental pterygium and had an immunomodulatory effect by decreasing TNF-α, IL-1α, and maintaining the level of IL-10 expression, without difference with respect to the healthy control. Traditional medical use of S. dendroideum sap to treat pterygium is fully justified by its compound composition. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

16 pages, 5546 KiB

Open AccessArticle

Assessment of Antidiabetic Activity of the Shikonin by Allosteric Inhibition of Protein-Tyrosine Phosphatase 1B (PTP1B) Using State of Art: An In Silico and In Vitro Tactics

by Mohd Saeed, Ambreen Shoaib, Munazzah Tasleem, Nadiyah M. Alabdallah, Md Jahoor Alam, Zeina El Asmar, Qazi Mohammad Sajid Jamal, Fevzi Bardakci, Saad S. Alqahtani, Irfan Ahmad Ansari and Riadh Badraoui

Molecules 2021, 26(13), 3996; https://doi.org/10.3390/molecules26133996 - 30 Jun 2021

Cited by 36 | Viewed by 4427

Abstract

Diabetes mellitus is a multifactorial disease that affects both developing and developed countries and is a major public health concern. Many synthetic drugs are available in the market, which counteracts the associated pathologies. However, due to the propensity of side effects, there is [...] Read more.

Diabetes mellitus is a multifactorial disease that affects both developing and developed countries and is a major public health concern. Many synthetic drugs are available in the market, which counteracts the associated pathologies. However, due to the propensity of side effects, there is an unmet need for the investigation of safe and effective drugs. This research aims to find a novel phytoconstituent having diminished action on blood glucose levels with the least side effects. Shikonin is a naturally occurring naphthoquinone dying pigment obtained by the roots of the Boraginaceae family. Besides its use as pigments, it can be used as an antimicrobial, anti-inflammatory, and anti-tumor agent. This research aimed to hypothesize the physicochemical and phytochemical properties of Shikonin’s in silico interaction with protein tyrosine phosphate 1B, as well as it’s in vitro studies, in order to determine its potential anti-diabetic impact. To do so, molecular docking experiments with target proteins were conducted to assess their anti-diabetic ability. Analyzing associations with corresponding amino acids revealed the significant molecular interactions between Shikonin and diabetes-related target proteins. In silico pharmacokinetics and toxicity profile of Shikonin using ADMET Descriptor, Toxicity Prediction, and Calculate Molecular Properties tools from Biovia Discovery Studio v4.5. Filter by Lipinski and Veber Rule’s module from Biovia Discovery Studio v4.5 was applied to assess the drug-likeness of Shikonin. The in vitro studies exposed that Shikonin shows an inhibitory potential against the PTP1B with an IC50 value of 15.51 µM. The kinetics studies revealed that it has a competitive inhibitory effect (Ki = 7.5 M) on the enzyme system, which could be useful in the production of preventive and therapeutic agents. The findings of this research suggested that the Shikonin could be used as an anti-diabetic agent and can be used as a novel source for drug delivery. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

19 pages, 2402 KiB

Open AccessArticle

Chemical Constitution and Antimicrobial Activity of Kefir Fermented Beverage

by Abdul-Raouf Al-Mohammadi, Rehab A. Ibrahim, Ahmed H. Moustafa, Ahmed A. Ismaiel, Azza Abou Zeid and Gamal Enan

Molecules 2021, 26(9), 2635; https://doi.org/10.3390/molecules26092635 - 30 Apr 2021

Cited by 31 | Viewed by 4022

Abstract

Kefir beverage (KB) is a fermented milk initiated by kefir grains rich with starter probiotics. The KB produced in this study seemed to contain many chemical compounds elucidated by gas chromatography–mass spectrometry (GC-MS) and IR spectra. These compounds could be classified into different [...] Read more.

Kefir beverage (KB) is a fermented milk initiated by kefir grains rich with starter probiotics. The KB produced in this study seemed to contain many chemical compounds elucidated by gas chromatography–mass spectrometry (GC-MS) and IR spectra. These compounds could be classified into different chemical groups such as alcohols, phenols, esters, fatty esters, unsaturated fatty esters, steroids, polyalkenes, heterocyclic compounds and aromatic aldehydes. Both KB and neutralized kefir beverage (NKB) inhibited some pathogenic bacteria including Escherichia coli ATCC11229 (E. coli), Listeria monocytogenes ATCC 4957 (L. monocytogenes), Bacillus cereus ATCC 14579 (B. cereus), Salmonella typhimurium ATCC 14028 (Sal. typhimurium) as well as some tested fungal strains such as Aspergillus flavus ATCC 16872 (A. flavus) and Aspergillus niger ATCC 20611 (A. niger), but the inhibitory activity of KB was more powerful than that obtained by NKB. It also appeared to contain four lactic acid bacteria species, one acetic acid bacterium and two yeast species. Finally, the KB inhibited distinctively both S. aureus and Sal. typhimurium bacteria in a brain heart infusion broth and in some Egyptian fruit juices, including those made with apples, guava, strawberries and tomatoes. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

22 pages, 14278 KiB

Open AccessArticle

Antioxidant and Antidiabetic Activity of Proanthocyanidins from Fagopyrum dibotrys

by Xin Li, Jingling Liu, Qinxiang Chang, Ziyun Zhou, Ruilian Han and Zongsuo Liang

Molecules 2021, 26(9), 2417; https://doi.org/10.3390/molecules26092417 - 21 Apr 2021

Cited by 39 | Viewed by 3806

Abstract

Proanthocyanidins are natural glycosidase inhibitors with excellent antioxidant activity. This study aims to search for a new source of proanthocyanidins for the prevention and treatment of type 2 diabetes with higher content and better activity and get their structure elucidated. First, the total [...] Read more.

Proanthocyanidins are natural glycosidase inhibitors with excellent antioxidant activity. This study aims to search for a new source of proanthocyanidins for the prevention and treatment of type 2 diabetes with higher content and better activity and get their structure elucidated. First, the total proanthocyanidins contents (TOPCs), antioxidant activity, antidiabetic activity of seven common Polygonaceae plants were analyzed and compared. Then proanthocyanidins from the rhizome of Fagopyrum dibotrys were purified, and the detailed structure was comprehensively analyzed by ultraviolet visible spectroscopy (UV-Vis), Fourier transform infrared spectroscopy (FT-IR), ¹³C nuclear magnetic resonance spectroscopy (¹³C NMR), reversed-phase high-performance liquid chromatography-electrospray mass spectrometry (RP-HPLC-ESI-MS), and matrix-assisted laser desorption/ionization-time of flight mass spectrometry (MALDI-TOF MS). The rhizome of F. dibotrys showed the highest TOPCs, the strongest antioxidant, and antidiabetic activities; the TOPCs, antioxidant and antidiabetic activities were all very significantly positively correlated. Proanthocyanidins purified from the rhizome of F. dibotrys showed better antidiabetic activity than grape seed proanthocyanidins (GsPs). Seventy-two proanthocyanidins from trimer to undecamer with a mean degree of polymerization (mDP) of about 5.02 ± 0.21 were identified with catechin and epicatechin as the dominant monomers. Conclusion: Proanthocyanidins are the main antioxidant and antidiabetic active substances of F. dibotrys and are expected to be developed into potential antioxidant and hypoglycemic products. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

19 pages, 348 KiB

Open AccessArticle

A Comparison of the Nutritional and Biochemical Quality of Date Palm Fruits Obtained Using Different Planting Techniques

by Jeerawan Hinkaew, Amornrat Aursalung, Yuraporn Sahasakul, Nattapol Tangsuphoom and Uthaiwan Suttisansanee

Molecules 2021, 26(8), 2245; https://doi.org/10.3390/molecules26082245 - 13 Apr 2021

Cited by 26 | Viewed by 3310

Abstract

Date palm fruit (Phoenix dactylifera L.) is commonly consumed around the world and has recently become an economical crop in Eastern Thailand, especially the Barhi cultivar that can be consumed as fresh fruit. To maintain genetic qualities, date palm is populated through [...] Read more.

Date palm fruit (Phoenix dactylifera L.) is commonly consumed around the world and has recently become an economical crop in Eastern Thailand, especially the Barhi cultivar that can be consumed as fresh fruit. To maintain genetic qualities, date palm is populated through cell culture. This leads to high production costs, while access to this technique is limited. Increasing date palm population by simple seed planting is currently of interest as an alternative for local farmers. Nevertheless, information on nutritive values, bioactive compounds, and health-promoting bioactivities of seed originating from date palm fruit is unavailable. Effects of different planting origins (cell culture origin (CO) and seed origin (SO)) of date palm fruits at the Khalal stage of Barhi cultivar were investigated for nutritive values, bioactive compounds, and in vitro health-promoting properties via key enzyme inhibitions against obesity (lipase), diabetes (α-amylase, α-glucosidase, and dipeptidyl peptidase-IV), Alzheimer’s disease (cholinesterases and β-secretase), and hypertension (angiotensin-converting enzyme). Waste seeds as a by-product from date palm production were also examined regarding these properties to increase seed marketing opportunities for future food applications and other health-related products. CO and SO exhibited insignificant differences in energy, fat, and carbohydrate contents. SO had higher protein, dietary fiber, vitamin A, vitamin E, and calcium contents than CO, while CO contained higher contents of fructose, glucose and maltose. Higher phenolic contents in SO led to greater enzyme inhibitory activities than CO. Interestingly, seeds of date palm fruits mostly contained higher nutritive values than the flesh. No carotenoids were detected in seeds but higher phenolic contents resulted in greater enzyme inhibitory activities than recorded for fruit flesh. Results suggest that appropriate planting of date palm can support the development of novel date palm fruit products, leading to expansion of economic opportunities and investment in date palm fruit agriculture. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

12 pages, 857 KiB

Open AccessArticle

Six New Phenylpropanoid Derivatives from Chemically Converted Extract of Alpinia galanga (L.) and Their Antiparasitic Activities

by Melanny Ika Sulistyowaty, Nguyen Hoang Uyen, Keisuke Suganuma, Ben-Yeddy Abel Chitama, Kazuhide Yahata, Osamu Kaneko, Sachiko Sugimoto, Yoshi Yamano, Susumu Kawakami, Hideaki Otsuka and Katsuyoshi Matsunami

Molecules 2021, 26(6), 1756; https://doi.org/10.3390/molecules26061756 - 21 Mar 2021

Cited by 15 | Viewed by 3774

Abstract

Chemical conversion of the extract of natural resources is a very attractive way to expand the chemical space to discover bioactive compounds. In order to search for new medicines to treat parasitic diseases that cause high morbidity and mortality in affected countries in [...] Read more.

Chemical conversion of the extract of natural resources is a very attractive way to expand the chemical space to discover bioactive compounds. In order to search for new medicines to treat parasitic diseases that cause high morbidity and mortality in affected countries in the world, the ethyl acetate extract from the rhizome of Alpinia galanga (L.) has been chemically converted by epoxidation using dioxirane generated in situ. The biological activity of chemically converted extract (CCE) of A. galanga (L.) significantly increased the activity against Leishmania major up to 82.6 ± 6.2 % at 25 μg/mL (whereas 2.7 ± 0.8% for the original extract). By bioassay-guided fractionation, new phenylpropanoids (1–6) and four known compounds, hydroquinone (7), 4-hydroxy(4-hydroxyphenyl)methoxy)benzaldehyde (8), isocoumarin cis 4-hydroxymelein (9), and (2S,3S,6R,7R,9S,10S)-humulene triepoxide (10) were isolated from CCE. The structures of isolated compounds were determined by spectroscopic analyses of 1D and 2D NMR, IR, and MS spectra. The most active compound was hydroquinone (7) with IC₅₀ = 0.37 ± 1.37 μg/mL as a substantial active principle of CCE. In addition, the new phenylpropanoid 2 (IC₅₀ = 27.8 ± 0.34 μg/mL) also showed significant activity against L. major compared to the positive control miltefosine (IC₅₀ = 7.47 ± 0.3 μg/mL). The activities of the isolated compounds were also evaluated against Plasmodium falciparum, Trypanosoma brucei gambisense and Trypanosoma brucei rhodeisense. Interestingly, compound 2 was selectively active against trypanosomes with potent activity. To the best of our knowledge, this is the first report on the bioactive “unnatural” natural products from the crude extract of A. galanga (L.) by chemical conversion and on its activities against causal pathogens of leishmaniasis, trypanosomiasis, and malaria. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Graphical abstract

14 pages, 4874 KiB

Open AccessArticle

Preparation and Optimization of PEGylated Nano Graphene Oxide-Based Delivery System for Drugs with Different Molecular Structures Using Design of Experiment (DoE)

by Mohammad Hossain Shariare, Abdullah-Al Masum, Sultan Alshehri, Fars K. Alanazi, Jamal Uddin and Mohsin Kazi

Molecules 2021, 26(5), 1457; https://doi.org/10.3390/molecules26051457 - 7 Mar 2021

Cited by 12 | Viewed by 3635

Abstract

Graphene oxide (GO), due to its 2D planar structure and favorable physical and chemical properties, has been used in different fields including drug delivery. This study aimed to investigate the impact of different process parameters on the average size of drug-loaded PEGylated nano [...] Read more.

Graphene oxide (GO), due to its 2D planar structure and favorable physical and chemical properties, has been used in different fields including drug delivery. This study aimed to investigate the impact of different process parameters on the average size of drug-loaded PEGylated nano graphene oxide (NGO-PEG) particles using design of experiment (DoE) and the loading of drugs with different molecular structures on an NGO-PEG-based delivery system. GO was prepared from graphite, processed using a sonication method, and functionalized using PEG 6000. Acetaminophen (AMP), diclofenac (DIC), and methotrexate (MTX) were loaded onto NGO-PEG particles. Drug-loaded NGO-PEG was then characterized using dynamic light scattering (DLS), Fourier transform infrared (FTIR), scanning electron microscopy (SEM), differential scanning calorimetry (DSC), XRD. The DLS data showed that the drug-loaded NGO-PEG suspensions were in the size range of 200 nm–1.3 µm. The sonication time and the stirring rate were found to be the major process parameters which affected the average size of the drug-loaded NGO-PEG. FTIR, DSC, XRD, and SEM demonstrated that the functionalization or coating of the NGO occurred through physical interaction using PEG 6000. Methotrexate (MTX), with the highest number of aromatic rings, showed the highest loading efficiency of 95.6% compared to drugs with fewer aromatic rings (diclofenac (DIC) 70.5% and acetaminophen (AMP) 65.5%). This study suggests that GO-based nano delivery systems can be used to deliver drugs with multiple aromatic rings with a low water solubility and targeted delivery (e.g., cancer). Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Graphical abstract

18 pages, 7294 KiB

Open AccessArticle

Ameliorating the Adverse Effects of Tomato mosaic tobamovirus Infecting Tomato Plants in Egypt by Boosting Immunity in Tomato Plants Using Zinc Oxide Nanoparticles

by Ahmed R. Sofy, Mahmoud R. Sofy, Ahmed A. Hmed, Rehab A. Dawoud, Abd El-Aleem M. Alnaggar, Ahmed M. Soliman and Noha K. El-Dougdoug

Molecules 2021, 26(5), 1337; https://doi.org/10.3390/molecules26051337 - 2 Mar 2021

Cited by 67 | Viewed by 4929

Abstract

Tomato mosaic virus (ToMV) is one of the economically damageable Tobamovirus infecting the tomato in Egypt that has caused significant losses. It is therefore of great interest to trigger systemic resistance to ToMV. In this endeavor, we aimed to explore the capacity of [...] Read more.

Tomato mosaic virus (ToMV) is one of the economically damageable Tobamovirus infecting the tomato in Egypt that has caused significant losses. It is therefore of great interest to trigger systemic resistance to ToMV. In this endeavor, we aimed to explore the capacity of ZnO-NPs (zinc oxide nanoparticles) to trigger tomato plant resistance against ToMV. Effects of ZnO-NPs on tomato (Solanum lycopersicum L.) growth indices and antioxidant defense system activity under ToMV stress were investigated. Noticeably that treatment with ZnO-NPs showed remarkably increased growth indices, photosynthetic attributes, and enzymatic and non-enzymatic antioxidants compared to the challenge control. Interestingly, oxidative damage caused by ToMV was reduced by reducing malondialdehyde, H₂O₂, and O₂ levels. Overall, ZnO-NPs offer a safe and economic antiviral agent against ToMV. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

14 pages, 2538 KiB

Open AccessArticle

Pentacyclic Triterpene Profile and Its Biosynthetic Pathway in Cecropia telenitida as a Prospective Dietary Supplement

by Gustavo Gutiérrez, Laura Marcela Valencia, Deisy Giraldo-Dávila, Marianny Y. Combariza, Elkin Galeano, Norman Balcazar, Aram J. Panay, Alejandra Maria Jerez and Guillermo Montoya

Molecules 2021, 26(4), 1064; https://doi.org/10.3390/molecules26041064 - 18 Feb 2021

Cited by 4 | Viewed by 3684

Abstract

Promising research over the past decades has shown that some types of pentacyclic triterpenes (PTs) are associated with the prevention of type 2 diabetes (T2D), especially those found in foods. The most abundant edible sources of PTs are those belonging to the ursane [...] Read more.

Promising research over the past decades has shown that some types of pentacyclic triterpenes (PTs) are associated with the prevention of type 2 diabetes (T2D), especially those found in foods. The most abundant edible sources of PTs are those belonging to the ursane and oleanane scaffold. The principal finding is that Cecropia telenitida contains abundant oleanane and ursane PT types with similar oxygenation patterns to those found in food matrices. We studied the compositional profile of a rich PT fraction (DE16-R) and carried out a viability test over different cell lines. The biosynthetic pathway connected to the isolated PTs in C. telenitida offers a specific medicinal benefit related to the modulation of T2D. This current study suggests that this plant can assemble isobaric, positional isomers or epimeric PT. Ursane or oleanane scaffolds with the same oxygenation pattern are always shared by the PTs in C. telenitida, as demonstrated by its biosynthetic pathway. Local communities have long used this plant in traditional medicine, and humans have consumed ursane and oleanane PTs in fruits since ancient times, two key points we believe useful in considering the medicinal benefits of C. telenitida and explaining how a group of molecules sharing a closely related scaffold can express effectiveness. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Graphical abstract

19 pages, 2567 KiB

Open AccessArticle

Identification of Mushroom and Murine Tyrosinase Inhibitors from Achillea biebersteinii Afan. Extract

by Marcelina Strzępek-Gomółka, Katarzyna Gaweł-Bęben, Apostolis Angelis, Beata Antosiewicz, Zuriyadda Sakipova, Kaldanay Kozhanova, Kazimierz Głowniak and Wirginia Kukula-Koch

Molecules 2021, 26(4), 964; https://doi.org/10.3390/molecules26040964 - 11 Feb 2021

Cited by 32 | Viewed by 4217

Abstract

Growing scientific evidence indicates that Achillea biebersteinii is a valuable source of active ingredients with potential cosmetic applications. However, the data on its composition and pharmacological properties are still insufficient. This study aims to optimize the extraction procedure of the plant material, evaluate [...] Read more.

Growing scientific evidence indicates that Achillea biebersteinii is a valuable source of active ingredients with potential cosmetic applications. However, the data on its composition and pharmacological properties are still insufficient. This study aims to optimize the extraction procedure of the plant material, evaluate its phytochemical composition, and compare anti-tyrosinase potential of A. biebersteinii extracts obtained by various methods. In order to identify compounds responsible for the tyrosinase inhibitory activity of A. biebersteinii, the most active anti-tyrosinase extract was fractionated by column chromatography. The fractions were examined for their skin lightening potential by mushroom and murine tyrosinase inhibitory assays and melanin release assay. HPLC-ESI-Q-TOF-MS/MS analysis of the total extract revealed the presence of several phenolic acids, flavonoids, flavonoid glucosides, and carboxylic acid. Among them, fraxetin-8-O-glucoside, quercetin-O-glucopyranose, schaftoside/isoschaftoside, gmelinin B, 1,3-dicaffeoylquinic acid (1,3-DCQA), and ferulic acid were found in the fractions with the highest skin lightening potential. Based on obtained qualitative and quantitative analysis of the fractions, it was assumed that the caffeoylquinic acid derivatives and dicaffeoylquinic acid derivatives are more likely responsible for mushroom tyrosinase inhibitory activity of A. biebersteinii extracts and fractions. Ferulic acid was proposed as the most active murine tyrosinase inhibitor, responsible also for the reduced melanin release from B16F10 murine melanoma cells. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

16 pages, 2061 KiB

Open AccessArticle

Mechanistic Studies of the Antiallergic Activity of Phyllanthus amarus Schum. & Thonn. and Its Compounds

by Nur Zahirah Abd Rani, Kok Wai Lam, Juriyati Jalil, Hazni Falina Mohamad, Mohd Shukri Mat Ali and Khairana Husain

Molecules 2021, 26(3), 695; https://doi.org/10.3390/molecules26030695 - 28 Jan 2021

Cited by 14 | Viewed by 3703

Abstract

Phyllanthus amarus Schum. & Thonn. (Phyllanthaceae) is a medicinal plant that is commonly used to treat diseases such as asthma, diabetes, and anemia. This study aimed to examine the antiallergic activity of P. amarus extract and its compounds. The antiallergic activity was determined [...] Read more.

Phyllanthus amarus Schum. & Thonn. (Phyllanthaceae) is a medicinal plant that is commonly used to treat diseases such as asthma, diabetes, and anemia. This study aimed to examine the antiallergic activity of P. amarus extract and its compounds. The antiallergic activity was determined by measuring the concentration of allergy markers release from rat basophilic leukemia (RBL-2H3) cells with ketotifen fumarate as the positive control. As a result, P. amarus did not stabilize mast cell degranulation but exhibited antihistamine activity. The antihistamine activity was evaluated by conducting a competition radioligand binding assay on the histamine 1 receptor (H1R). Four compounds were identified from the high performance liquid chromatography (HPLC) analysis which were phyllanthin (1), hypophyllanthin (2), niranthin (3), and corilagin (4). To gain insights into the binding interactions of the most active compound hypophyllanthin (2), molecular docking was conducted and found that hypophyllanthin (2) exhibited favorable binding in the H1R binding site. In conclusion, P. amarus and hypophyllanthin (2) could potentially exhibit antiallergic activity by preventing the activation of the H1 receptor. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

11 pages, 4195 KiB

Open AccessArticle

Modulation of Lipid Metabolism by Trans-Anethole in Hepatocytes

by Ahran Song, Yoonjin Park, Boyong Kim and Seung Gwan Lee

Molecules 2020, 25(21), 4946; https://doi.org/10.3390/molecules25214946 - 26 Oct 2020

Cited by 11 | Viewed by 3600

Abstract

Non-alcoholic fatty liver disease is caused by excessive lipid accumulation in hepatocytes. Although trans-anethole (TAO) affects hypoglycemia and has anti-immune activity and anti-obesity effects, its role in non-alcoholic fatty liver disease remains unknown. This study aimed to evaluate the effects of TAO on [...] Read more.

Non-alcoholic fatty liver disease is caused by excessive lipid accumulation in hepatocytes. Although trans-anethole (TAO) affects hypoglycemia and has anti-immune activity and anti-obesity effects, its role in non-alcoholic fatty liver disease remains unknown. This study aimed to evaluate the effects of TAO on cellular senescence, lipid metabolism, and reinforcement of microenvironments in HepG2 cells. To analyze the lipid metabolic activity of TAO, PCR analysis, flow-cytometry, and Oil Red O staining were performed, and mitochondrial membrane potential (MMP) and cellular senescence kits were used for assessing the suppression of cellular senescence. At 2000 μg/mL TAO, the cellular viability was approximately 99%, and cell senescence decreased dose-dependently. In the results for MMP, activity increased with concentration. The levels of lipolytic genes, CPT2, ACADS, and HSL, strongly increased over 3 days and the levels of lipogenic genes, ACC1 and GPAT, were downregulated on the first day at 1000 μg/mL TAO. Consequently, it was found that TAO affects the suppression of cellular senescence, activation of lipid metabolism, and reinforcement of the microenvironment in HepG2 cells, and can be added as a useful component to functional foods to prevent fatty liver disease and cellular senescence, as well as increase the immunoactivity of the liver. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

Review

Jump to: Research

27 pages, 8865 KiB

Open AccessReview

Antioxidant Properties and Structure-Antioxidant Activity Relationship of Allium Species Leaves

by Dikdik Kurnia, Dwipa Ajiati, Leny Heliawati and Dadan Sumiarsa

Molecules 2021, 26(23), 7175; https://doi.org/10.3390/molecules26237175 - 26 Nov 2021

Cited by 33 | Viewed by 5030

Abstract

Allium is a genus that is widely consumed and used as traditional medicine in several countries. This genus has two major species, namely cultivated species and wild species. Cultivated species consist of A. cepa L., A. sativum L., A. fistulosum L. and A. [...] Read more.

Allium is a genus that is widely consumed and used as traditional medicine in several countries. This genus has two major species, namely cultivated species and wild species. Cultivated species consist of A. cepa L., A. sativum L., A. fistulosum L. and A. schoenoprasum L. and wild species consist of A. ursinum L., A. flavum L., A. scorodoprasum L., A. vineale L. and A. atroviolaceum Boiss. Several studies report that the Allium species contain secondary metabolites such as polyphenols, flavonoids and tannins and have bioactivity such as antioxidants, antibacterial, antifungal, anti-inflammatory, pancreatic α-amylase, glucoamylase enzyme inhibitors and antiplatelets. This review summarizes some information regarding the types of Allium species (ethnobotany and ethnopharmacology), the content of compounds of Allium species leaves with various isolation methods, bioactivities, antioxidant properties and the structure-antioxidant activity relationship (SAR) of Allium compounds. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

11 pages, 2251 KiB

Open AccessReview

Applications and Restrictions of Integrated Genomic and Metabolomic Screening: An Accelerator for Drug Discovery from Actinomycetes?

by Janina Krause

Molecules 2021, 26(18), 5450; https://doi.org/10.3390/molecules26185450 - 7 Sep 2021

Cited by 7 | Viewed by 2660

Abstract

Since the golden age of antibiotics in the 1950s and 1960s actinomycetes have been the most prolific source for bioactive natural products. However, the number of discoveries of new bioactive compounds decreases since decades. New procedures (e.g., activating strategies or innovative fermentation techniques) [...] Read more.

Since the golden age of antibiotics in the 1950s and 1960s actinomycetes have been the most prolific source for bioactive natural products. However, the number of discoveries of new bioactive compounds decreases since decades. New procedures (e.g., activating strategies or innovative fermentation techniques) were developed to enhance the productivity of actinomycetes. Nevertheless, compound identification remains challenging among others due to high rediscovery rates. Rapid and cheap genome sequencing as well as the advent of bioinformatical analysis tools for biosynthetic gene cluster identification in combination with mass spectrometry-based molecular networking facilitated the tedious process of dereplication. In recent years several studies have been dedicated to accessing the biosynthetic potential of Actinomyces species, especially streptomycetes, by using integrated genomic and metabolomic screening in order to boost the discovery rate of new antibiotics. This review aims to present the various possible applications of this approach as well as the newly discovered molecules, covering studies between 2014 and 2021. Finally, the effectiveness of this approach with regard to find new bioactive agents from actinomycetes will be evaluated. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

22 pages, 2643 KiB

Open AccessFeature PaperReview

Chemical Diversity and Biological Activity of Secondary Metabolites Isolated from Indonesian Marine Invertebrates

by Fauzia Izzati, Mega Ferdina Warsito, Asep Bayu, Anggia Prasetyoputri, Akhirta Atikana, Linda Sukmarini, Siti Irma Rahmawati and Masteria Yunovilsa Putra

Molecules 2021, 26(7), 1898; https://doi.org/10.3390/molecules26071898 - 27 Mar 2021

Cited by 23 | Viewed by 5478

Abstract

Marine invertebrates have been reported to be an excellent resource of many novel bioactive compounds. Studies reported that Indonesia has remarkable yet underexplored marine natural products, with a high chemical diversity and a broad spectrum of biological activities. This review discusses recent updates [...] Read more.

Marine invertebrates have been reported to be an excellent resource of many novel bioactive compounds. Studies reported that Indonesia has remarkable yet underexplored marine natural products, with a high chemical diversity and a broad spectrum of biological activities. This review discusses recent updates on the exploration of marine natural products from Indonesian marine invertebrates (i.e., sponges, tunicates, and soft corals) throughout 2007–2020. This paper summarizes the structural diversity and biological function of the bioactive compounds isolated from Indonesian marine invertebrates as antimicrobial, antifungal, anticancer, and antiviral, while also presenting the opportunity for further investigation of novel compounds derived from Indonesian marine invertebrates. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Identification and Biological Activity)

► Show Figures

Figure 1

Journal Menu

Journal Browser

Natural Products: Isolation, Identification and Biological Activity

Share This Special Issue

Special Issue Editor

Special Issue Information

Keywords

Benefits of Publishing in a Special Issue

Related Special Issue

Published Papers (21 papers)

Research

Review

Further Information

Guidelines

MDPI Initiatives

Follow MDPI