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Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (15 June 2023) | Viewed by 35246

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Prof. Dr. Chia Ming Chang

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Department of Soil and Environmental Sciences, National Chung Hsing University, Taichung 40227, Taiwan
Interests: plant bioactive compounds; plant toxins; alkaloids; biological activity; spectroscopy;density functional theory; machine learning; virtual screening
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Phytochemicals are increasingly used due to their various useful properties and health benefits. They can not only be used as a source of biopesticides, but are also suitable for food industry and pharmaceutical applications. To explore the modification, synthesis, transformation and structure–activity relationship of phytochemicals, it is necessary to identify the structure of phytochemicals. The process of purifying the components of plant extracts through isolation methods and obtaining microscopic structural information through various spectroscopic measurements provides the necessary foundation for this.

Some alkaloids in phytochemicals are classified as plant toxins. Exposure to toxic alkaloids can lead to specific mechanisms involving enzymes, receptors, transporters and genetic materials in specific cells and tissues, which can cause biological toxicity. Many phytochemicals have specific biological and pharmacological activities, including antioxidant, anti-inflammatory, antibacterial and anticancer effects. In-depth research is needed to understand the potential functions of phytochemicals, and clinical trials are needed to verify the health benefits of phytochemicals.

Phytochemistry research is increasingly combined with computer-aided drug-design technology. Computational methods include molecular modeling, computational biology, chemoinformatics, machine learning, deep learning, and virtual screening to systematically identify biologically active compounds in phytochemical databases. In addition, for phytochemical components that are not clearly bound to the target, the in silico method is a useful tool to identify the target and clarify the mechanism of action. Therefore, this Special Issue will collect meticulous research on the extraction, isolation, identification, toxicology and pharmacology of phytochemicals, and the application of the experimental and computational achievements of phytochemicals to make original research contributions in the field of environment, food and health, among others.

Dr. Chia Ming Chang
Guest Editor

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Keywords

phytochemical
isolation
mass spectrometry
nuclear magnetic resonance
biological activity
molecular modeling
machine learning
virtual screening

Published Papers (13 papers)

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11 pages, 1530 KiB

Open AccessArticle

Chemical and Biological Aspects of Different Species of the Genus Clinanthus Herb. (Amaryllidaceae) from South America

by María Lenny Rodríguez-Escobar, Luciana R. Tallini, Julia Lisa-Molina, Strahil Berkov, Francesc Viladomat, Alan Meerow, Jaume Bastida and Laura Torras-Claveria

Molecules 2023, 28(14), 5408; https://doi.org/10.3390/molecules28145408 - 14 Jul 2023

Cited by 1 | Viewed by 878

Abstract

The genus Clinanthus Herb. is found in the Andes Region (South America), mainly in Peru, Ecuador, and Bolivia. These plants belong to the Amaryllidaceae family, specifically the Amaryllidoideae subfamily, which presents an exclusive group of alkaloids known as Amaryllidaceae alkaloids that show important structural diversity and pharmacological properties. It is possible to find some publications in the literature regarding the botanical aspects of Clinanthus species, although there is little information available about their chemical and biological activities. The aim of this work was to obtain the alkaloid profile and the anti-cholinesterase activity of four different samples of Clinanthus collected in South America: Clinanthus sp., Clinanthus incarnatus, and Clinanthus variegatus. The alkaloid extract of each sample was analyzed by gas chromatography coupled with mass spectrometry (GC-MS), and their potential against the enzymes acetyl- and butyrylcholinesterase were evaluated. Thirteen alkaloids have been identified among these species, while six unidentified structures have also been detected in these plants. The alkaloid extract of the C. variegatus samples showed the highest structural diversity as well as the best activity against AChE, which was likely due to the presence of the alkaloid sanguinine. The results suggest this genus as a possible interesting new source of Amaryllidaceae alkaloids, which could contribute to the development of new medicines. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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27 pages, 4241 KiB

Open AccessFeature PaperArticle

Annotation and Identification of Phytochemicals from Eleusine indica Using High-Performance Liquid Chromatography Tandem Mass Spectrometry: Databases-Driven Approach

by Nur Syahirah Mad Sukor, Zikry Hamizan Md Zakri, Nurulfazlina Edayah Rasol and Fatimah Salim

Molecules 2023, 28(7), 3111; https://doi.org/10.3390/molecules28073111 - 30 Mar 2023

Cited by 5 | Viewed by 2972

Abstract

Eleusine indica (L.) Gaertn is a perennial herb belonging to the Poaceae family. As the only species of Eleusine found abundantly in Malaysia, it is locally known as “rumput sambau” and has been traditionally used to treat various ailments including pain relief from vaginal bleeding, hastening the placenta delivery after childbirth, asthma, hemorrhoids, urinary infection, fever, and as a tonic for flu-related symptoms. A diverse array of biological activities have been reported for the plant, such as antimicrobial, cytotoxic, anticonvulsant, anti-inflammatory, analgesic, antipyretic, and hepatoprotective action. Despite many reports on its traditional uses and biological activities, limited chemical databases are available for the plant. Thus, the aims of this study were to annotate and identify the phytochemical constituents in the methanolic extract of E. indica through tandem LCMS-based analysis techniques using MZmine, GNPS, Compound Discoverer, and SIRIUS platforms. This technique managed to identify a total of 65 phytochemicals in the extract, comprising primary and secondary metabolites, and was verified by the isolation of one of the identified phytochemicals. The structural elucidation mainly using 1D and 2D NMR as well as comparison with values in the literature confirms the isolated phytochemical to be a 3-OH anomer of loliolide, a benzofuran-type of compound, which consequently increases the level of confidence in the applied technique. The research describes a useful method for the fast and simultaneous identification of phytochemicals in E. indica, contributing to the study of the chemical properties of the genus and family. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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25 pages, 5096 KiB

Open AccessArticle

Molecular Modeling and In Vitro Evaluation of Piplartine Analogs against Oral Squamous Cell Carcinoma

by Rayanne H. N. Silva, Thaíssa Q. Machado, Anna Carolina C. da Fonseca, Eduardo Tejera, Yunierkis Perez-Castillo, Bruno K. Robbs and Damião P. de Sousa

Molecules 2023, 28(4), 1675; https://doi.org/10.3390/molecules28041675 - 09 Feb 2023

Cited by 2 | Viewed by 2142

Abstract

Cancer is a principal cause of death in the world, and providing a better quality of life and reducing mortality through effective pharmacological treatment remains a challenge. Among malignant tumor types, squamous cell carcinoma-esophageal cancer (EC) is usually located in the mouth, with approximately 90% located mainly on the tongue and floor of the mouth. Piplartine is an alkamide found in certain species of the genus Piper and presents many pharmacological properties including antitumor activity. In the present study, the cytotoxic potential of a collection of piplartine analogs against human oral SCC9 carcinoma cells was evaluated. The analogs were prepared via Fischer esterification reactions, alkyl and aryl halide esterification, and a coupling reaction with PyBOP using the natural compound 3,4,5-trimethoxybenzoic acid as a starting material. The products were structurally characterized using ¹H and ¹³C nuclear magnetic resonance, infrared spectroscopy, and high-resolution mass spectrometry for the unpublished compounds. The compound 4-methoxy-benzyl 3,4,5-trimethoxybenzoate (9) presented an IC₅₀ of 46.21 µM, high selectively (SI > 16), and caused apoptosis in SCC9 cancer cells. The molecular modeling study suggested a multi-target mechanism of action for the antitumor activity of compound 9 with CRM1 as the main target receptor. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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13 pages, 1654 KiB

Open AccessArticle

Virtual Extensive Read-Across: A New Open-Access Software for Chemical Read-Across and Its Application to the Carcinogenicity Assessment of Botanicals

by Edoardo Luca Viganò, Erika Colombo, Giuseppa Raitano, Alberto Manganaro, Alessio Sommovigo, Jean Lou CM Dorne and Emilio Benfenati

Molecules 2022, 27(19), 6605; https://doi.org/10.3390/molecules27196605 - 05 Oct 2022

Cited by 5 | Viewed by 2009

Abstract

Read-across applies the principle of similarity to identify the most similar substances to represent a given target substance in data-poor situations. However, differences between the target and the source substances exist. The present study aims to screen and assess the effect of the key components in a molecule which may escape the evaluation for read-across based only on the most similar substance(s) using a new open-access software: Virtual Extensive Read-Across (VERA). VERA provides a means to assess similarity between chemicals using structural alerts specific to the property, pre-defined molecular groups and structural similarity. The software finds the most similar compounds with a certain feature, e.g., structural alerts and molecular groups, and provides clusters of similar substances while comparing these similar substances within different clusters. Carcinogenicity is a complex endpoint with several mechanisms, requiring resource intensive experimental bioassays and a large number of animals; as such, the use of read-across as part of new approach methodologies would support carcinogenicity assessment. To test the VERA software, carcinogenicity was selected as the endpoint of interest for a range of botanicals. VERA correctly labelled 70% of the botanicals, indicating the most similar substances and the main features associated with carcinogenicity. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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13 pages, 2132 KiB

Open AccessArticle

Isolation of Mirificin and Other Bioactive Isoflavone Glycosides from the Kudzu Root Lyophilisate Using Centrifugal Partition and Flash Chromatographic Techniques

by Magdalena Maciejewska-Turska, Łukasz Pecio and Grażyna Zgórka

Molecules 2022, 27(19), 6227; https://doi.org/10.3390/molecules27196227 - 22 Sep 2022

Cited by 5 | Viewed by 1584

Abstract

Pueraria lobata (Willd.) Ohwi is a legume taxon native to Southeast Asia and widely used in traditional medicine systems of that region. The therapeutic applications of the underground parts of this species (known as kudzu root) are related to its high content of isoflavones, mainly the characteristic C-glycoside derivatives. Within this group, the most explored compound both phytochemically and pharmacologically is puerarin. However, current scientific findings document important anti-biodegenerative effects for some of the minor isoflavones from kudzu roots. Therefore, the main objective of the study was to develop an original preparative method that allowed the efficient isolation of closely related hydrophilic daidzein C-glycosides, including mirificin, from vacuum-dried aqueous-ethanolic extracts of kudzu roots. For this purpose, the combined centrifugal partition (CPC) and flash chromatographic (FC) techniques were elaborated and used. The optimized biphasic solvent system in CPC, with ethyl acetate, ethanol, water, and 0.5% (V/V) acetic acid as a mobile phase modifier, enabled the purification and separation of the polar fraction containing bioactive isoflavones and ultimately the isolation of mirificin, 3′-hydroxy- and 3′-methoxypuerarin, puerarin, and daidzin using FC. The identity of isoflavones was confirmed using spectroscopic (UV absorption and nuclear magnetic resonance) and mass spectrometric methods. The determined purity of isolated mirificin was 63%. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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16 pages, 2623 KiB

Open AccessArticle

Molecular Modeling Study of Novel Lancifolamide Bioactive Molecule as an Inhibitor of Acetylcholinesterase (AChE), Herpes Simplex Virus (HSV-1), and Anti-proliferative Proteins

by Malik Saadullah, Arshad Farid, Asad Ali, Muhammad Rashad, Faiza Naseem, Sheikh Abdur Rashid, Shakira Ghazanfar, Muhammad Yasin, Nosheen Akhtar, Mohammed S. Almuhayawi, Mohammed H. Alruhaili and Samy Selim

Molecules 2022, 27(17), 5480; https://doi.org/10.3390/molecules27175480 - 26 Aug 2022

Cited by 1 | Viewed by 2103

Abstract

Combretaceae, an immense family involving species (500) or genera (20), originates in tropical and subtropical regions. This family has evinced medicinal values such as anti-leishmanial, cytotoxic, antibacterial, antidiabetic, antiprotozoal, and antifungal properties. Conocarpus lancifolius (C. lancifolius) methanol extract (CLM) was prepared, then compound isolation performed by open column chromatography, and compound structure was determined by spectroscopic techniques (¹³C NMR, IR spectroscopy, ¹H-NMR, mass spectrometry UV-visible, and 2D correlation techniques). Molecular docking studies of ligand were performed on transcriptional regulators 4EY7 and 2GV9 to observe possible interactions. Phytochemical screening revealed the presence of secondary metabolites including steroids, cardiac glycosides, saponins, anthraquinones, and flavonoids. The isolated compound was distinguished as lancifolamide (LFD). It showed cytotoxic activity against human breast cancer, murine lymphocytic leukemia, and normal cells, human embryonic kidney cells, and rat glioma cells with IC₅₀ values of 0.72 µg/mL, 2.01 µg/mL, 1.55 µg/mL, and 2.40 µg/mL, respectively. Although no cytotoxic activity was noticed against human colon cancer and human lung cancer, LFD showed 24.04% inhibition against BChE and 60.30% inhibition against AChE and is therefore beneficial for Alzheimer’s disease (AD). AChE and LFD interact mechanistically in a way that is optimum for neurodegenerative disorders, according to molecular docking studies. Methanol and dichloromethane extract of C. lancifolius and LFD shows antibacterial and antifungal activity against antibiotic resistance Bacillus subtilis, Streptococcus mutans, Brevibacillus laterosporus, Salmonella Typhi, Candida albicans, and Cryptococcus neoformans, respectively. LFD shows antiviral activity against HSV-1 with 26% inhibition IP. The outcomes of this study support the use of LFD for cognitive disorders and highlight its underlying mechanism, targeting AChE, DNA-POL, NF-KB, and TNF-α, etc., for the first time. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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17 pages, 2827 KiB

Open AccessArticle

In Silico Target Identification of Galangin, as an Herbal Flavonoid against Cholangiocarcinoma

by Brinda Balasubramanian, Simran Venkatraman, Kyaw Zwar Myint, Sucheewin Krobthong, Patompon Wongtrakoongate, Jittiyawadee Sripa, Panthip Rattanasinganchan, Pornphimon Metheenukul and Rutaiwan Tohtong

Molecules 2022, 27(14), 4664; https://doi.org/10.3390/molecules27144664 - 21 Jul 2022

Cited by 1 | Viewed by 2615

Abstract

Cholangiocarcinoma (CCA) is a heterogenous group of malignancies in the bile duct, which proliferates aggressively. CCA is highly prevalent in Northeastern Thailand wherein it is associated with liver fluke infection, or Opisthorchis viverrini (OV). Most patients are diagnosed in advanced stages, when the cancer has metastasized or severely progressed, thereby limiting treatment options. Several studies investigate the effect of traditional Thai medicinal plants that may be potential therapeutic options in combating CCA. Galangin is one such herbal flavonoid that has medicinal properties and exhibits anti-tumor properties in various cancers. In this study, we investigate the role of Galangin in inhibiting cell proliferation, invasion, and migration in OV-infected CCA cell lines. We discovered that Galangin reduced cell viability and colony formation by inducing apoptosis in CCA cell lines in a dose-dependent manner. Further, Galangin also effectively inhibited invasion and migration in OV-infected CCA cells by reduction of MMP2 and MMP9 enzymatic activity. Additionally, using proteomics, we identified proteins affected post-treatment with Galangin. Enrichment analysis revealed that several kinase pathways were affected by Galangin, and the signature corroborated with that of small molecule kinase inhibitors. Hence, we identified putative targets of Galangin using an in silico approach which highlighted c-Met as candidate target. Galangin effectively inhibited c-Met phosphorylation and subsequent signaling in in vitro CCA cells. In addition, Galangin was able to inhibit HGF, a mediator of c-Met signaling, by suppressing HGF-stimulated invasion, as well as migration and MMP9 activity. This shows that Galangin can be a useful anti-metastatic therapeutic strategy in a subtype of CCA patients. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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18 pages, 4266 KiB

Open AccessArticle

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

by Rochelly da Silva Mesquita, Andrii Kyrylchuk, Anton Cherednichenko, Ingrity Suelen Costa Sá, Lílian Macedo Bastos, Felipe Moura Araújo da Silva, Rita de Cássia Saraiva Nunomura and Andriy Grafov

Molecules 2022, 27(10), 3138; https://doi.org/10.3390/molecules27103138 - 13 May 2022

Cited by 4 | Viewed by 2173

Abstract

Alkaloids are natural products known as ethnobotanicals that have attracted increasing attention due to a wide range of their pharmacological properties. In this study, cholinesterase inhibitors were obtained from branches of Abuta panurensis Eichler (Menispermaceae), an endemic species from the Amazonian rainforest. Five alkaloids were isolated, and their structure was elucidated by a combination of 1D and 2D ¹H and ¹³C NMR spectroscopy, HPLC-MS, and high-resolution MS: Lindoldhamine isomer m/z 569.2674 (1), stepharine m/z 298.1461 (2), palmatine m/z 352.1616 (3), 5-N-methylmaytenine m/z 420.2669 (4) and the N-trans-feruloyltyramine m/z 314.1404 (5). The compounds 1, 3, and 5 were isolated from A. panurensis for the first time. Interaction of the above-mentioned alkaloids with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes was investigated in silico by molecular docking and molecular dynamics. The molecules under investigation were able to bind effectively with the active sites of the AChE and BChE enzymes. The compounds 1–4 demonstrated in vitro an inhibitory effect on acetylcholinesterase with IC₅₀ values in the range of 19.55 µM to 61.24 µM. The data obtained in silico corroborate the results of AChE enzyme inhibition. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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13 pages, 2454 KiB

Open AccessArticle

Dioscin-Mediated Autophagy Alleviates MPP⁺-Induced Neuronal Degeneration: An In Vitro Parkinson’s Disease Model

by Shofiul Azam, Md. Ezazul Haque, Duk-Yeon Cho, Joon-Soo Kim, Md. Jakaria, In-Su Kim and Dong-Kug Choi

Molecules 2022, 27(9), 2827; https://doi.org/10.3390/molecules27092827 - 29 Apr 2022

Cited by 5 | Viewed by 2332

Abstract

Autophagy is a cellular homeostatic process by which cells degrade and recycle their malfunctioned contents, and impairment in this process could lead to Parkinson’s disease (PD) pathogenesis. Dioscin, a steroidal saponin, has induced autophagy in several cell lines and animal models. The role of dioscin-mediated autophagy in PD remains to be investigated. Therefore, this study aims to investigate the hypothesis that dioscin-regulated autophagy and autophagy-related (ATG) proteins could protect neuronal cells in PD via reducing apoptosis and enhancing neurogenesis. In this study, the 1-methyl-4-phenylpyridinium ion (MPP⁺) was used to induce neurotoxicity and impair autophagic flux in a human neuroblastoma cell line (SH-SY5Y). The result showed that dioscin pre-treatment counters MPP⁺-mediated autophagic flux impairment and alleviates MPP⁺-induced apoptosis by downregulating activated caspase-3 and BCL2 associated X, apoptosis regulator (Bax) expression while increasing B-cell lymphoma 2 (Bcl-2) expression. In addition, dioscin pre-treatment was found to increase neurotrophic factors and tyrosine hydroxylase expression, suggesting that dioscin could ameliorate MPP⁺-induced degeneration in dopaminergic neurons and benefit the PD model. To conclude, we showed dioscin’s neuroprotective activity in neuronal SH-SY5Y cells might be partly related to its autophagy induction and suppression of the mitochondrial apoptosis pathway. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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24 pages, 14258 KiB

Open AccessArticle

Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from Artemisia glauca

by Yerlan M. Suleimen, Rani A. Jose, Raigul N. Suleimen, Margarita Y. Ishmuratova, Suzanne Toppet, Wim Dehaen, Aisha A. Alsfouk, Eslam B. Elkaeed, Ibrahim H. Eissa and Ahmed M. Metwaly

Molecules 2022, 27(7), 2281; https://doi.org/10.3390/molecules27072281 - 31 Mar 2022

Cited by 18 | Viewed by 4905

Abstract

A new dicoumarin, jusan coumarin, (1), has been isolated from Artemisia glauca aerial parts. The chemical structure of jusan coumarin was estimated, by 1D, 2D NMR as well as HR-Ms spectroscopic methods, to be 7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-6-yl)oxy]-2H-chromen-2-one. As the first time to be introduced in nature, its potential against SARS-CoV-2 has been estimated using various in silico methods. Molecular similarity and fingerprints experiments have been utilized for 1 against nine co-crystallized ligands of COVID-19 vital proteins. The results declared a great similarity between Jusan Coumarin and X77, the ligand of COVID-19 main protease (PDB ID: 6W63), M^pro. To authenticate the obtained outputs, a DFT experiment was achieved to confirm the similarity of X77 and 1. Consequently, 1 was docked against M^pro. The results clarified that 1 bonded in a correct way inside M^pro active site, with a binding energy of −18.45 kcal/mol. Furthermore, the ADMET and toxicity profiles of 1 were evaluated and showed the safety of 1 and its likeness to be a drug. Finally, to confirm the binding and understand the thermodynamic characters between 1 and M^pro, several molecular dynamics (MD) simulations studies have been administered. Additionally, the known coumarin derivative, 7-isopentenyloxycoumarin (2), has been isolated as well as β-sitosterol (3). Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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18 pages, 8589 KiB

Open AccessArticle

Isolation and In Silico Anti-SARS-CoV-2 Papain-Like Protease Potentialities of Two Rare 2-Phenoxychromone Derivatives from Artemisia spp.

by Yerlan M. Suleimen, Rani A. Jose, Raigul N. Suleimen, Christoph Arenz, Margarita Ishmuratova, Suzanne Toppet, Wim Dehaen, Aisha A. Alsfouk, Eslam B. Elkaeed, Ibrahim H. Eissa and Ahmed M. Metwaly

Molecules 2022, 27(4), 1216; https://doi.org/10.3390/molecules27041216 - 11 Feb 2022

Cited by 27 | Viewed by 4346

Abstract

Two rare 2-phenoxychromone derivatives, 6-demethoxy-4`-O-capillarsine (1) and tenuflorin C (2), were isolated from the areal parts of Artemisia commutata and A. glauca, respectively, for the first time. Being rare in nature, the inhibition potentialities of 1 and 2 against SARS-CoV-2 was investigated using multistage in silico techniques. At first, molecular similarity and fingerprint studies were conducted for 1 and 2 against co-crystallized ligands of eight different COVID-19 enzymes. The carried-out studies indicated the similarity of 1 and 2 with TTT, the co-crystallized ligand of COVID-19 Papain-Like Protease (PLP), (PDB ID: 3E9S). Therefore, molecular docking studies of 1 and 2 against the PLP were carried out and revealed correct binding inside the active site exhibiting binding energies of −18.86 and −18.37 Kcal/mol, respectively. Further, in silico ADMET in addition to toxicity evaluation of 1 and 2 against seven models indicated the general safety and the likeness of 1 and 2 to be drugs. Lastly, to authenticate the binding and to investigate the thermodynamic characters, molecular dynamics (MD) simulation studies were conducted on 1 and PLP. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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24 pages, 3594 KiB

Open AccessReview

Ergothioneine, Ovothiol A, and Selenoneine—Histidine-Derived, Biologically Significant, Trace Global Alkaloids

by Geoffrey A. Cordell and Sujeewa N. S. Lamahewage

Molecules 2022, 27(9), 2673; https://doi.org/10.3390/molecules27092673 - 21 Apr 2022

Cited by 8 | Viewed by 3931

Abstract

The history, chemistry, biology, and biosynthesis of the globally occurring histidine-derived alkaloids ergothioneine (10), ovothiol A (11), and selenoneine (12) are reviewed comparatively and their significance to human well-being is discussed. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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Other

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6 pages, 585 KiB

Open AccessBrief Report

Isolation of Various Flavonoids with TRAIL Resistance-Overcoming Activity from Blumea lacera

by Teruhisa Manome, Yasumasa Hara and Masami Ishibashi

Molecules 2023, 28(1), 264; https://doi.org/10.3390/molecules28010264 - 28 Dec 2022

Viewed by 1250

Abstract

Eighteen compounds, including fourteen flavonoids (1–14), one steroid (15), two fatty acids (16,17), and one nitrogen-containing compound (18), were isolated from the methanol extract of the whole Blumea lacera plant collected in Thailand. Compounds 1–11 and 15–17 exhibited tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) resistance-overcoming activity. Among them, bonanzin (2) and cirsilineol (7) had particularly strong TRAIL resistance-overcoming activity, where the IC₅₀ values against the human gastric adenocarcinoma cell line AGS in the presence of TRAIL (100 ng/mL) were 10.7 μM and 5.9 μM, respectively. Full article

(This article belongs to the Special Issue Phytochemicals: Isolation, Identification, Biological Activity and Computational Studies)

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