Molecules

Research

21 pages, 3012 KiB

Open AccessArticle

Light-Emitting Diodes and Liquid System Affect the Caffeoylquinic Acid Derivative and Flavonoid Production and Shoot Growth of Rhaponticum carthamoides (Willd.) Iljin

by Ewa Skała, Monika A. Olszewska, Przemysław Tabaka and Agnieszka Kicel

Molecules 2024, 29(9), 2145; https://doi.org/10.3390/molecules29092145 - 5 May 2024

Cited by 1 | Viewed by 986

Abstract

Plant in vitro cultures can be an effective tool in obtaining desired specialized metabolites. The purpose of this study was to evaluate the effect of light-emitting diodes (LEDs) on phenolic compounds in Rhaponticum carthamoides shoots cultured in vitro. R. carthamoides is an endemic [...] Read more.

Plant in vitro cultures can be an effective tool in obtaining desired specialized metabolites. The purpose of this study was to evaluate the effect of light-emitting diodes (LEDs) on phenolic compounds in Rhaponticum carthamoides shoots cultured in vitro. R. carthamoides is an endemic and medicinal plant at risk of extinction due to the massive harvesting of its roots and rhizomes from the natural environment. The shoots were cultured on an agar-solidified and liquid-agitated Murashige and Skoog’s medium supplemented with 0.1 mg/L of indole-3-acetic acid (IAA) and 0.5 mg/L of 6-benzyladenine (BA). The effect of the medium and different treatments of LED lights (blue (BL), red (RL), white (WL), and a combination of red and blue (R:BL; 7:3)) on R. carthamoides shoot growth and its biosynthetic potential was observed. Medium type and the duration of LED light exposure did not affect the proliferation rate of shoots, but they altered the shoot morphology and specialized metabolite accumulation. The liquid medium and BL light were the most beneficial for the caffeoylquinic acid derivatives (CQAs) production, shoot growth, and biomass increment. The liquid medium and BL light enhanced the content of the sum of all identified CQAs (6 mg/g DW) about three-fold compared to WL light and control, fluorescent lamps. HPLC-UV analysis confirmed that chlorogenic acid (5-CQA) was the primary compound in shoot extracts regardless of the type of culture and the light conditions (1.19–3.25 mg/g DW), with the highest level under R:BL light. BL and RL lights were equally effective. The abundant component was also 3,5-di-O-caffeoylquinic acid, accompanied by 4,5-di-O-caffeoylquinic acid, a tentatively identified dicaffeoylquinic acid derivative, and a tricaffeoylquinic acid derivative 2, the contents of which depended on the LED light conditions. Full article

(This article belongs to the Special Issue New Insights into Bioactive Compounds from Natural Sources)

► Show Figures

Figure 1

20 pages, 315 KiB

Open AccessArticle

Green Approach to Enhance the Recovery of Polyphenols from Blackcurrant and Bilberry Leaves: Evaluation of Microwave-Assisted and Pressurized Liquid Extraction

by Ivona Elez Garofulić, Maja Repajić, Ena Cegledi, Erika Dobroslavić, Ana Dobrinčić, Zoran Zorić, Sandra Pedisić, Tatjana Franković, Martina Breški and Verica Dragović-Uzelac

Molecules 2024, 29(6), 1351; https://doi.org/10.3390/molecules29061351 - 18 Mar 2024

Cited by 1 | Viewed by 1072

Abstract

The aim of the present study was to evaluate microwave-assisted (MAE) and pressurized liquid extraction (PLE) for the recovery of polyphenols from blackcurrant and bilberry leaves and the preservation of their antioxidant activity. The extractions were carried out varying the solvent/solid (SS) ratio, [...] Read more.

The aim of the present study was to evaluate microwave-assisted (MAE) and pressurized liquid extraction (PLE) for the recovery of polyphenols from blackcurrant and bilberry leaves and the preservation of their antioxidant activity. The extractions were carried out varying the solvent/solid (SS) ratio, temperature and time. During MAE, increasing the SS ratio increased the polyphenol concentration in the extracts from blackcurrant and bilberry leaves, while increasing the temperature had a positive effect only on bilberry polyphenols. During PLE, only a temperature increase was a determining factor for the isolation of blackcurrant leave polyphenols. Based on polyphenol recovery, optimal extraction parameters were established resulting in a yield of 62.10 and 56.06 mg/g dw in the blackcurrant and bilberry MAE extracts and 78.90 and 70.55 mg/g dw in the PLE extracts. The optimized extracts were profiled by UPLC ESI MS², and their antioxidant capacity was evaluated through FRAP, DPPH, ABTS and ORAC assays. The characterization of the extracts by UPLC ESI MS² confirmed flavonols as the predominant compounds in both blackcurrant and bilberry leaves, while flavan-3-ols and procyanidins were the main compounds responsible for high antioxidant capacity as confirmed by the ABTS and ORAC assays. Due to the extract composition and antioxidant capacity, PLE proved to be a technique of choice for the production of blackcurrant and bilberry leave extracts with high potential for use as value-added ingredients in the food and nutraceutical industry. Full article

(This article belongs to the Special Issue New Insights into Bioactive Compounds from Natural Sources)

12 pages, 1131 KiB

Open AccessArticle

Isolation and Structure Elucidation of New Metabolites from the Mariana-Trench-Associated Fungus Aspergillus sp. SY2601

by Cangzhu Sun, Yura Ha, Xin Liu, Nan Wang, Xiao-Yuan Lian and Zhizhen Zhang

Molecules 2024, 29(2), 459; https://doi.org/10.3390/molecules29020459 - 17 Jan 2024

Cited by 5 | Viewed by 1410

Abstract

Fungi are important resource for the discovery of novel bioactive natural products. This study investigated the metabolites produced by Mariana-Trench-associated fungus Aspergillus sp. SY2601 in EY liquid and rice solid media, resulting in the isolation and structure determination of 28 metabolites, including five [...] Read more.

Fungi are important resource for the discovery of novel bioactive natural products. This study investigated the metabolites produced by Mariana-Trench-associated fungus Aspergillus sp. SY2601 in EY liquid and rice solid media, resulting in the isolation and structure determination of 28 metabolites, including five new compounds, asperindopiperazines A–C (1–3), 5-methoxy-8,9-dihydroxy-8,9-deoxyaspyrone (21), and 12S-aspertetranone D (26). Structures of the new compounds were elucidated based on extensive NMR spectral analyses, HRESIMS data, optical rotation, ECD, and ¹³C NMR calculations. The new compound 12S-aspertetranone D (26) exhibited antibacterial activity against both methicillin-resistant Staphylococcus aureus and Escherichia coli with MIC values of 3.75 and 5 μg/mL, respectively. Full article

(This article belongs to the Special Issue New Insights into Bioactive Compounds from Natural Sources)

► Show Figures

Figure 1

20 pages, 3499 KiB

Open AccessArticle

Salazinic Acid and Norlobaridone from the Lichen Hypotrachyna cirrhata: Antioxidant Activity, α-Glucosidase Inhibitory and Molecular Docking Studies

by Tatapudi Kiran Kumar, Bandi Siva, Basani Kiranmai, Vidya Jyothi Alli, Surender Singh Jadav, Araveeti Madhusudana Reddy, Joël Boustie, Françoise Le Devehat, Ashok Kumar Tiwari and Katragadda Suresh Babu

Molecules 2023, 28(23), 7840; https://doi.org/10.3390/molecules28237840 - 29 Nov 2023

Cited by 1 | Viewed by 1539

Abstract

The present study was intended for the identification of secondary metabolites in acetone extract of the lichen Hypotrachyna cirrhata using UPLC-ESI-QToF-MS/MS and the detection of bioactive compounds. This study led to the identification of 22 metabolites based on their MS/MS spectra, accurate molecular [...] Read more.

The present study was intended for the identification of secondary metabolites in acetone extract of the lichen Hypotrachyna cirrhata using UPLC-ESI-QToF-MS/MS and the detection of bioactive compounds. This study led to the identification of 22 metabolites based on their MS/MS spectra, accurate molecular masses, molecular formula from a comparison of the literature database (DNP), and fragmentation patterns. In addition, potent antioxidant and α-glucosidase inhibitory potentials of acetone extract of H. cirrhata motivated us to isolate 10 metabolites, which were characterized as salazinic acid (11), norlobaridone (12), atranorin (13), lecanoric acid (14), lichesterinic acid (15), protolichesterinic acid (16), methyl hematommate (17), iso-rhizonic acid (18), atranol (19), and methylatratate (20) based on their spectral data. All these isolates were assessed for their free radicals scavenging, radical-induced DNA damage, and intestinal α-glucosidase inhibitory activities. The results indicated that norlobaridone (12), lecanoric acid (14), methyl hematommate (17), and atranol (19) showed potent antioxidant activity, while depsidones (salazinic acid (11), norlobaridone (12)) and a monophenolic compound (iso-rhizonic acid, (18)) displayed significant intestinal α-glucosidase inhibitory activities (p < 0.001), which is comparable to standard acarbose. These results were further correlated with molecular docking studies, which indicated that the alkyl chain of norlobaridione (12) is hooked into the finger-like cavity of the allosteric pocket; moreover, it also established Van der Waals interactions with hydrophobic residues of the allosteric pocket. Thus, the potency of norlobaridone to inhibit α-glucosidase enzyme might be associated with its allosteric binding. Also, MM-GBSA (Molecular Mechanics-Generalized Born Surface Area) binding free energies of salazinic acid (11) and norlobaridone (12) were superior to acarbose and may have contributed to their high activity compared to acarbose. Full article

(This article belongs to the Special Issue New Insights into Bioactive Compounds from Natural Sources)

► Show Figures

Graphical abstract

12 pages, 1226 KiB

Open AccessArticle

Red Kale (Brassica oleracea L. ssp. acephala L. var. sabellica) Induces Apoptosis in Human Colorectal Cancer Cells In Vitro

by Kamila Rachwał, Iwona Niedźwiedź, Adam Waśko, Tomasz Laskowski, Paweł Szczeblewski, Wirginia Kukula-Koch and Magdalena Polak-Berecka

Molecules 2023, 28(19), 6938; https://doi.org/10.3390/molecules28196938 - 5 Oct 2023

Viewed by 1792

Abstract

This article presents the results of studies investigating the effect of red kale (Brassica oleracea L. ssp. acephala L. var. sabellica) extract on cancer cells (HT-29). The cytotoxicity of the red kale extract was assessed using MTT and LDH assays, while [...] Read more.

This article presents the results of studies investigating the effect of red kale (Brassica oleracea L. ssp. acephala L. var. sabellica) extract on cancer cells (HT-29). The cytotoxicity of the red kale extract was assessed using MTT and LDH assays, while qRT-PCR was employed to analyze the expression of genes associated with the p53 signaling pathway to elucidate the effect of the extract on cancer cells. Furthermore, HPLC-ESI-QTOF-MS/MS was applied to identify bioactive compounds present in red kale. The obtained results indicated that red kale extract reduced the viability and suppressed the proliferation of HT-29 cells (the IC₅₀ value of 60.8 µg/mL). Additionally, mRNA expression analysis revealed significant upregulation of several genes, i.e., casp9, mapk10, mapk11, fas, kat2 b, and ubd, suggesting the induction of cell apoptosis through the caspase-dependent pathway. Interestingly, the study revealed a decrease in the expression of genes including cdk2 and cdk4 encoding cell cycle-related proteins, which may lead to cell cycle arrest. Furthermore, the study identified certain bioactive compounds, such as sinigrin, spirostanol, hesperetin and usambarensine, which could potentially contribute to the apoptotic effect of red kale extracts. However, further investigations are necessary to elucidate the specific role of these individual compounds in the anti-cancer process. Full article

(This article belongs to the Special Issue New Insights into Bioactive Compounds from Natural Sources)

► Show Figures

Graphical abstract

18 pages, 1448 KiB

Open AccessArticle

Effects of In Vitro Digestion of Polyphenols from Coffee on Binding Parameters to Human Topoisomerase II α

by Joanna Grzelczyk, Horacio Pérez-Sánchez, Miguel Carmena-Bargueño, Joanna Oracz and Grażyna Budryn

Molecules 2023, 28(16), 5996; https://doi.org/10.3390/molecules28165996 - 10 Aug 2023

Cited by 2 | Viewed by 1398

Abstract

Type II topoisomerase (TOPII) is an enzyme that influences the topology of DNA. DNA breaks generated by TOPII may result in mutagenic or cytotoxic changes in cancer cells. In this study, we characterized interactions of TOPIIα with coffee extracts and individual chlorogenic acids [...] Read more.

Type II topoisomerase (TOPII) is an enzyme that influences the topology of DNA. DNA breaks generated by TOPII may result in mutagenic or cytotoxic changes in cancer cells. In this study, we characterized interactions of TOPIIα with coffee extracts and individual chlorogenic acids (CHAs) from the extracts by performing isothermal titration calorimetry (ITC) and molecular docking (MD) simulations. The study showed that the highest affinity to TOPIIα was found in green coffee (ΔG = −38.23 kJ/mol) and monochlorogenic acids fraction of coffee extracts (ΔG = −35.80 kJ/mol), resulting from the high content of polyphenols, such as CHAs, which can bind to the enzyme in the active site. Coffee extracts and their fractions maintained a high affinity for TOPIIα after simulated digestion in the presence of probiotic bacteria. It can be concluded that coffee may be a potential TOPIIα inhibitor considered as a functional food for cancer prevention. Full article

(This article belongs to the Special Issue New Insights into Bioactive Compounds from Natural Sources)

► Show Figures

Figure 1

19 pages, 4985 KiB

Open AccessArticle

Unveiling the Structural Characteristics and Bioactivities of the Polysaccharides Extracted from Endophytic Penicillium sp.

by Kumar Vishven Naveen, Anbazhagan Sathiyaseelan, Sumana Mandal, Kiseok Han and Myeong-Hyeon Wang

Molecules 2023, 28(15), 5788; https://doi.org/10.3390/molecules28155788 - 31 Jul 2023

Cited by 1 | Viewed by 1248

Abstract

Polysaccharides are abundantly present in fungi and are gaining recognition for their exceptional bioactivities. Hence, the present study aimed to extract intracellular polysaccharides (IPS-1 and IPS-2) from the endophytic Penicillium radiatolobatum and compare their physicochemical and bioactive attributes. The monosaccharide composition analysis revealed [...] Read more.

Polysaccharides are abundantly present in fungi and are gaining recognition for their exceptional bioactivities. Hence, the present study aimed to extract intracellular polysaccharides (IPS-1 and IPS-2) from the endophytic Penicillium radiatolobatum and compare their physicochemical and bioactive attributes. The monosaccharide composition analysis revealed the existence of galactose, glucose, and mannose in both the IPS, while a trace amount of xylose was found in IPS-1. Further, FT-IR, ¹H NMR, and ¹³C NMR analysis suggested that the IPS-2 was mainly composed of the β-(1→4)-D-Galactose and β-(1→4)-D-Glucose as the main chain, with the β-(1→6)-D-mannose as branched chains. Compared to IPS-1, the IPS-2 showed higher antioxidant activities with an IC₅₀ value of 108 ± 2.5 μg/mL, 272 ± 4.0 μg/mL, and 760 ± 5.0 μg/mL for ABTS⁺ scavenging, DPPH radical scavenging, and ferric reducing power, respectively. In addition, the IPS-2 inhibited the viability of prostate cancer (PC-3) cells (IC₅₀; 435 ± 3.0 μg/mL) via apoptosis associated with mitochondrial membrane potential collapse and altered morphological features, which was revealed by cellular staining and flow cytometric analysis. Moreover, no apparent cytotoxic effects were seen in IPS-2-treated (1000 μg/mL) non-cancerous cells (HEK-293 and NIH3T3). Overall, the findings of this study suggest that P. radiatolobatum could be a potent source of polysaccharides with promising antioxidant and anticancer activity. Full article

(This article belongs to the Special Issue New Insights into Bioactive Compounds from Natural Sources)

► Show Figures

Figure 1

16 pages, 1181 KiB

Open AccessArticle

Potentiality Assessment of the Acetylcholinesterase-Inhibitory Activity of Olive Oil with an Additive Edible Insect Powder

by Joanna Grzelczyk, Ilona Gałązka-Czarnecka and Joanna Oracz

Molecules 2023, 28(14), 5535; https://doi.org/10.3390/molecules28145535 - 20 Jul 2023

Cited by 2 | Viewed by 1538

Abstract

Edible insects (Alphitobius diaperinus Panzer, Gryllus campestris, Tenebrio molitor, Chorthippus biguttulus) are rich in nutrients that potentially inhibit acetylcholinesterase (AChE), but also improve cognition. The aim of this study was to evaluate four varied species of freeze-dried edible insects [...] Read more.

Edible insects (Alphitobius diaperinus Panzer, Gryllus campestris, Tenebrio molitor, Chorthippus biguttulus) are rich in nutrients that potentially inhibit acetylcholinesterase (AChE), but also improve cognition. The aim of this study was to evaluate four varied species of freeze-dried edible insects (purchased from a store); their nutrient composition, including fat, total phenolic compounds, vitamins, and antioxidant properties; and the potential inhibitory effect of AChE. An additional goal was to obtain olive oil with the addition of edible insects. Such oil was characterized by high oxidizing properties and showed high affinity to AChE. The results showed that mealworms and grasshoppers had the highest content of fats (PUFA/SFA) and phenolic compounds. These insects also showed a high content of vitamins, which correlated with the highest affinity for AChE. Therefore, they were added as a functional additive to olive oil. Olive oil with the addition of edible insects showed a higher affinity for AChE and enriched the olive oil with vitamin C and B vitamins. Full article

(This article belongs to the Special Issue New Insights into Bioactive Compounds from Natural Sources)

► Show Figures

Figure 1

Journal Menu

Journal Browser

New Insights into Bioactive Compounds from Natural Sources

Share This Special Issue

Special Issue Editors

Special Issue Information

Keywords

Benefits of Publishing in a Special Issue

Related Special Issue

Published Papers (8 papers)

Research

Further Information

Guidelines

MDPI Initiatives

Follow MDPI