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Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons

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

Deadline for manuscript submissions: closed (31 March 2022) | Viewed by 38926

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Dr. Agnieszka Ludwiczuk

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Department of Pharmacognosy with the Medicinal Plant Garden, Medical University of Lublin, Lublin, Poland
Interests: terpenoids, essential oils and volatile extracts; chromatographic techniques; isolation; bryophytes natural product chemistry; bioactivity-guided isolation of compounds from medicinal; aromatic, and spore-forming plants; chemosystematics of liverworts based on their terpenoid, aromatic, and phenolic constituents
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Prof. Dr. Yoshinori Asakawa

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Guest Editor

Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan
Interests: natural product chemistry; isolation and structure elucidation of bioactive secondary metabolites of bryophytes, pteridophytes, inedible mushrooms, medicinal and aromatic plants and insects and their bioassay; biotransformation of secondary metabolites by fungi and mammals; total synthesis of natural products; chemical reaction of organic per-acids; chemical phylogeny of spore-forming plants

Special Issue Information

Dear Colleagues,

We welcome the submission of original research papers and review articles for the Special Issue of Molecules that will honor Prof. Simon Gibbons for his contribution in the field of Medicinal Phytochemistry.

He and his group have carried out excellent research in the chemistry and antibacterial activity of natural products from plants and his expertise is in the isolation, structure elucidation and biological evaluation of these compounds. He is also interested in compounds that modify bacterial resistance. A further focus of his research is into the characterization of natural and synthetic New Psychoactive Substances that can be crude plant or fungal materials or single natural or synthetic chemical entities.

Simon Gibbons is Head of the UEA School of Pharmacy and Professor of Natural Product Chemistry. He received BSc and PhD degrees in Chemistry and Phytochemistry respectively and worked in the Biotechnology sector in Natural Product Chemistry from 1993-1997. In October 1997 he was appointed as Assistant Professor of Pharmaceutical Chemistry at the Faculty of Pharmacy at Kuwait University and in 1999 moved to the University of London to become Lecturer in Pharmacognosy. In 2007 he was appointed as Professor of Phytochemistry. Currently, he is a co-opted member of the UK Government Home Office’s Cannabis-Based Medicinal Products Work Group and was a Council Member of the UK Home Office Advisory Council for the Misuse of Drugs (ACMD) and Chairman of the Novel Psychoactive Substances Committee (NPSC). From 2010-2012 he was a member of the Medicines and Healthcare Regulatory products Agency (MHRA) Herbal Medicines Advisory Committee (HMAC). In 2009 he was elected as a Fellow of the Prince of Wales Foundation for Integrated Health. He is also a Fellow of the Linnean Society of London and the Royal Society of Chemistry and in 2009 was invited to be an Associate Researcher of the University Kebangsaan Malaysia.

He was President and Vice-President of the Phytochemical Society of Europe from 2010-2016 and has been honoured for his work as recipient of the Pharmanex Prize for Phytochemistry (2012), the first Tshwane University of Technology Vice Chancellor’s Seminar Award (2009) and the 2005 Phytochemical Society of Europe - Pierre Fabre Award for Phytochemistry.

Simon Gibbons is founding Editor-in-Chief of Phytochemistry Letters and Co-editor of Progress in the Chemistry of Organic Natural Products (“Zechmeister”) and a member of the Editorial Boards of Journal of Natural Products, Phytochemical Analysis, Phytochemistry Reviews, Fitoterapia, Phytotherapy Research, Chinese Journal of Natural Medicines (CJNM), Scientia Pharmaceutica, Natural Products and Bioprospecting and Phytopharmacotherapy.

In the Special Issue, we aim to collect original research articles and review articles in the following topics:

Plant-derived antibacterials
Natural product bacterial resistance modifying agents
The chemistry and pharmacology of novel psychoactive substances and drugs of abuse
Phytochemistry of Herbal drugs
Bioactivity-guided isolation and structure characterization of compounds from medicinal plants
Bioactive potential of metabolites derived from plant endophytes
Synthetic transformations of biologically interesting compounds

Dr. Agnieszka Ludwiczuk
Prof. Dr. Yoshinori Asakawa
Guest Editors

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Keywords

natural products
medicinal plants
bioactive compounds
antibiotics
psychoactive drugs
isolation and structure elucidation
drug discovery

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Published Papers (10 papers)

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Research

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13 pages, 1662 KiB

Open AccessArticle

New C₁₅ Acetogenins from Two Species of Laurencia from the Aegean Sea

by Maria Harizani, Dafni-Ioanna Diakaki, Stamatios Perdikaris, Vassilios Roussis and Efstathia Ioannou

Molecules 2022, 27(6), 1866; https://doi.org/10.3390/molecules27061866 - 13 Mar 2022

Cited by 2 | Viewed by 2442

Abstract

The chemical diversity of the approximately 1,200 natural products isolated from red algae of the genus Laurencia, in combination with the wide range of their biological activities, have placed species of Laurencia in the spotlight of marine chemists’ attention for over 60 years. The chemical investigation of the organic (CH₂Cl₂/MeOH) extracts of Laurencia microcladia and Laurencia obtusa, both collected off the coasts of Tinos island in the Aegean Sea, resulted in the isolation of 32 secondary metabolites, including 23 C₁₅ acetogenins (1–23), 7 sesquiterpenes (24–30) and 2 diterpenes (31 and 32). Among them, six new C₁₅ acetogenins, namely 10-acetyl-sagonenyne (2), cis-sagonenyne (3), trans-thuwalenyne C (4), tinosallene A (11), tinosallene B (12) and obtusallene XI (17), were identified and their structures were elucidated by extensive analysis of their spectroscopic data. Compounds 1–3, 5–11, 13 and 15–32 were evaluated for their antibacterial activity against Staphylococcus aureus and Escherichia coli. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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11 pages, 1705 KiB

Open AccessArticle

Phytochemical Profile and Anticancer Potential of Endophytic Microorganisms from Liverwort Species, Marchantia polymorpha L.

by Mateusz Stelmasiewicz, Łukasz Świątek and Agnieszka Ludwiczuk

Molecules 2022, 27(1), 153; https://doi.org/10.3390/molecules27010153 - 28 Dec 2021

Cited by 13 | Viewed by 3287

Abstract

Liverwort endophytes could be a source of new biologically active substances, especially when these spore-forming plants are known to produce compounds that are not found in other living organisms. Despite the significant development of plant endophytes research, there are only a few studies describing liverwort endophytic microorganisms and their metabolites. In the presented study, the analysis of the volatile compounds obtained from thallose liverwort species, Marchantia polymorpha L., and its endophytes was carried out. For this purpose, non-polar extracts of plant material and symbiotic microorganisms were obtained. The extracts were analyzed using gas chromatography coupled to mass spectrometry. Compounds with the structure of diketopiperazine in the endophyte extract were identified. Liverwort volatile extract was a rich source of cuparane-, chamigrane-, acorane-, and thujopsane-type sesquiterpenoids. The cytotoxicity of ethyl acetate extracts from endophytic microorganisms was evaluated on a panel of cancer (FaDu, HeLa, and SCC-25) cell lines and normal (VERO), and revealed significant anticancer potential towards hypopharyngeal squamous cell carcinoma and cervical adenocarcinoma. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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8 pages, 647 KiB

Open AccessCommunication

Semisynthesis of Selenoauraptene

by Serena Fiorito, Francesco Epifano, Lorenzo Marchetti and Salvatore Genovese

Molecules 2021, 26(9), 2798; https://doi.org/10.3390/molecules26092798 - 10 May 2021

Cited by 2 | Viewed by 2171

Abstract

Selenium-containing compounds are gaining more and more interest due to their valuable and promising pharmacological properties, mainly as anticancer and antioxidant agents. Ebselen, the up to now only approved drugs, is well known to possess very good glutathione peroxidase mimicking effects. To date, the most of efforts have been directed to build pure synthetic Se containing molecules, while less attention have been devoted to Se-based semisynthetic products resembling natural compounds like terpenes, polyphenols, and alkaloids. The aim of this short communication is to report the synthesis of the first example of a Se-phenylpropanoids, namely selenoauraptene, containing a selenogeranyl side chain in position 7 of the umbelliferone core. The key step was the Newman-Kwart rearrangement to obtain a selenocarbamate in which the Se atom was directly attached to umbelliferone (replacing its 7-OH function) followed by hydrolysis to get diumbelliferyl diselenide, which was finally easily converted to the desired Se-geranyl derivative in quite a good overall yield (28.5%). The synthesized adduct displayed a greater antioxidant and a radical scavenger in vitro activity than parent auraptene. The procedure we describe herein, to the best of our knowledge for the first time in the literature, represents an easy-to-handle method for the synthesis of a wide array of seleno analogues of naturally occurring biologically active oxyprenylated secondary metabolites. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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17 pages, 4336 KiB

Open AccessFeature PaperArticle

Anti-MRSA Constituents from Ruta chalepensis (Rutaceae) Grown in Iraq, and In Silico Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl ether

by Shaymaa Al-Majmaie, Lutfun Nahar, M. Mukhlesur Rahman, Sushmita Nath, Priyanka Saha, Anupam Das Talukdar, George P. Sharples and Satyajit D. Sarker

Molecules 2021, 26(4), 1114; https://doi.org/10.3390/molecules26041114 - 19 Feb 2021

Cited by 19 | Viewed by 3945

Abstract

Ruta chalepensis L. (Rutaceae), a perennial herb with wild and cultivated habitats, is well known for its traditional uses as an anti-inflammatory, analgesic, antipyretic agent, and in the treatment of rheumatism, nerve diseases, neuralgia, dropsy, convulsions and mental disorders. The antimicrobial activities of the crude extracts from the fruits, leaves, stem and roots of R. chalepensis were initially evaluated against two Gram-positive and two Gram-negative bacterial strains and a strain of the fungus Candida albicans. Phytochemical investigation afforded 19 compounds, including alkaloids, coumarins, flavonoid glycosides, a cinnamic acid derivative and a long-chain alkane. These compounds were tested against a panel of methicillin-resistant Staphylococcus aureus (MRSA) strains, i.e., ATCC 25923, SA-1199B, XU212, MRSA-274819 and EMRSA-15. The MIC values of the active compounds, chalepin (9), chalepensin (10), rutamarin (11), rutin 3′-methyl ether (14), rutin 7,4′-dimethyl ether (15), 6-hydroxy-rutin 3′,7-dimethyl ether (16) and arborinine (18) were in the range of 32–128 µg/mL against the tested MRSA strains. Compounds 10 and 16 were the most active compounds from R. chalepensis, and were active against four out of six tested MRSA strains, and in silico studies were performed on these compounds. The anti-MRSA activity of compound 16 was comparable to that of the positive control norfloxacin (MICs 32 vs 16 μg/mL, respectively) against the MRSA strain XU212, which is a Kuwaiti hospital isolate that possesses the TetK tetracycline efflux pump. This is the first report on the anti-MRSA property of compounds isolated from R. chalepensis and relevant in silico studies on the most active compounds. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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Review

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48 pages, 1712 KiB

Open AccessReview

The Phytochemistry and Pharmacology of Tulbaghia, Allium, Crinum and Cyrtanthus: ‘Talented’ Taxa from the Amaryllidaceae

by Cynthia Amaning Danquah, Prince Amankwah Baffour Minkah, Theresa A. Agana, Phanankosi Moyo, Michael Ofori, Peace Doe, Sibusiso Rali, Isaiah Osei Duah Junior, Kofi Bonsu Amankwah, Samuel Owusu Somuah, Isaac Newton Nugbemado, Vinesh J. Maharaj, Sanjib Bhakta and Simon Gibbons

Molecules 2022, 27(14), 4475; https://doi.org/10.3390/molecules27144475 - 13 Jul 2022

Cited by 5 | Viewed by 4012

Abstract

Amaryllidaceae is a significant source of bioactive phytochemicals with a strong propensity to develop new drugs. The genera Allium, Tulbaghia, Cyrtanthus and Crinum biosynthesize novel alkaloids and other phytochemicals with traditional and pharmacological uses. Amaryllidaceae biomolecules exhibit multiple pharmacological activities such as antioxidant, antimicrobial, and immunomodulatory effects. Traditionally, natural products from Amaryllidaceae are utilized to treat non-communicable and infectious human diseases. Galanthamine, a drug from this family, is clinically relevant in treating the neurocognitive disorder, Alzheimer’s disease, which underscores the importance of the Amaryllidaceae alkaloids. Although Amaryllidaceae provide a plethora of biologically active compounds, there is tardiness in their development into clinically pliable medicines. Other genera, including Cyrtanthus and Tulbaghia, have received little attention as potential sources of promising drug candidates. Given the reciprocal relationship of the increasing burden of human diseases and limited availability of medicinal therapies, more rapid drug discovery and development are desirable. To expedite clinically relevant drug development, we present here evidence on bioactive compounds from the genera Allium, Tulgbaghia, Cyrtanthus and Crinum and describe their traditional and pharmacological applications. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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19 pages, 4060 KiB

Open AccessReview

Aquilaria Species (Thymelaeaceae) Distribution, Volatile and Non-Volatile Phytochemicals, Pharmacological Uses, Agarwood Grading System, and Induction Methods

by Yichen Wang, Mubasher Hussain, Zhenbin Jiang, Zhaohong Wang, Jing Gao, Fengxian Ye, Runqian Mao and He Li

Molecules 2021, 26(24), 7708; https://doi.org/10.3390/molecules26247708 - 20 Dec 2021

Cited by 22 | Viewed by 5737

Abstract

Agarwood is a highly valuable fragrant wood of Aquilaria spp. (Thymelaeaceae) which has been widely utilized in traditional medicine, religious rites, and cultural activities. This study summarizes a review on the identification of Aquilaria cultivars, volatile and non-volatile phytochemicals, pharmacological uses, and agarwood grading system to determine its quality, and different agarwood induction methods. Due to the highly demanding and depleted natural resources, the research on agarwood is still insufficient, and it has broad research and development prospects in many industries. However, due to the significant scientific nature of agarwood application, developing high-quality products and drugs from agarwood have become highly important, while no one has discussed in detail the phytochemicals uses and provided a summary until now. The main phytochemicals of agarwood include terpenoids, dominated by sesquiterpenes. For centuries, terpenoids have been used in traditional Chinese medicine and have been shown to possess various pharmacological properties, including bacteriostatic, antibacterial, sedation, analgesia, anti-inflammation, anti-asthmatic, hypoglycemic, antidepressant, and many others. Alongside biological activity screening, phytochemical advances and pharmacological research have also made certain progress. Therefore, this review discusses the research progress of agarwood in recent years and provides a reference basis for further study of Aquilaria plants and agarwood. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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18 pages, 1617 KiB

Open AccessReview

Flavonoids as Inhibitors of Bacterial Efflux Pumps

by Martin Waditzer and Franz Bucar

Molecules 2021, 26(22), 6904; https://doi.org/10.3390/molecules26226904 - 16 Nov 2021

Cited by 29 | Viewed by 3435

Abstract

Flavonoids are widely occurring secondary plant constituents, and are abundant in vegetable and fruit diets as well as herbal medicines. Therapeutic treatment options for bacterial infections are limited due to the spread of antimicrobial resistances. Hence, in a number of studies during the last few years, different classes of plant secondary metabolites as resistance-modifying agents have been carried out. In this review, we present the role of flavonoids as inhibitors of bacterial efflux pumps. Active compounds could be identified in the subclasses of chalcones, flavan-3-ols, flavanones, flavones, flavonols, flavonolignans and isoflavones; by far the majority of compounds were aglycones, although some glycosides like kaempferol glycosides with p-coumaroyl acylation showed remarkable results. Staphylococcus aureus NorA pump was the focus of many studies, followed by mycobacteria, whereas Gram-negative bacteria are still under-investigated. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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26 pages, 2931 KiB

Open AccessReview

Pharmacological Activities of Aminophenoxazinones

by Jesús G. Zorrilla, Carlos Rial, Daniel Cabrera, José M. G. Molinillo, Rosa M. Varela and Francisco A. Macías

Molecules 2021, 26(11), 3453; https://doi.org/10.3390/molecules26113453 - 7 Jun 2021

Cited by 10 | Viewed by 4127

Abstract

Aminophenoxazinones are degradation products resulting from the metabolism of different plant species, which comprise a family of natural products well known for their pharmacological activities. This review provides an overview of the pharmacological properties and applications proved by these compounds and their structural derivatives during 2000–2021. The bibliography was selected according to our purpose from the references obtained in a SciFinder database search for the Phx-3 structure (the base molecule of the aminophenoxazinones). Compounds Phx-1 and Phx-3 are among the most studied, especially as anticancer drugs for the treatment of gastric and colon cancer, glioblastoma and melanoma, among others types of relevant cancers. The main information available in the literature about their mechanisms is also described. Similarly, antibacterial, antifungal, antiviral and antiparasitic activities are presented, including species related directly or indirectly to significant diseases. Therefore, we present diverse compounds based on aminophenoxazinones with high potential as drugs, considering their levels of activity and few adverse effects. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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19 pages, 1289 KiB

Open AccessReview

An Overview of the Chemical Characteristics, Bioactivity and Achievements Regarding the Therapeutic Usage of Acetogenins from Annona cherimola Mill.

by Alexandra G. Durán, M. Teresa Gutiérrez, Francisco J. R. Mejías, José M. G. Molinillo and Francisco A. Macías

Molecules 2021, 26(10), 2926; https://doi.org/10.3390/molecules26102926 - 14 May 2021

Cited by 14 | Viewed by 4984

Abstract

Annona cherimola Mill., or the custard apple, is one of the species belonging to the Annonaceae family, is widely used in traditional medicine, and has been reported to be a valuable source of bioactive compounds. A unique class of secondary metabolites derived from this family are Annonaceous acetogenins, lipophilic polyketides considered to be amongst the most potent antitumor compounds. This review provides an overview of the chemical diversity, isolation procedures, bioactivity, modes of application and synthetic derivatives of acetogenins from A. cherimola Mill. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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10 pages, 2460 KiB

Open AccessReview

7-Isopentenyloxycoumarin: What Is New across the Last Decade

by Francesca Preziuso, Salvatore Genovese, Lorenzo Marchetti, Majid Sharifi-Rad, Lucia Palumbo, Francesco Epifano and Serena Fiorito

Molecules 2020, 25(24), 5923; https://doi.org/10.3390/molecules25245923 - 14 Dec 2020

Cited by 10 | Viewed by 2842

Abstract

7-Isopentenyloxycoumarin is among the most widespread naturally occurring prenyloxy umbelliferone derivatives. This secondary metabolite of mixed biosynthetic origin has been typically isolated from plants belonging to several genera of the Rutaceae and Apiaceae families, comprising widely used medicinal plants and in general plants with beneficial effects on human welfare, as well as edible fruits and vegetables. Although known for quite a long time (more than 50 years), only in the last two decades has this natural compound been revealed to exert powerful and promising pharmacological properties, such as active cancer chemopreventive, antibacterial, antiprotozoal, antifungal, anti-inflammatory, neuroprotective, and antioxidant properties, among the activities best outlined in the recent literature. The aim of this comprehensive miniature review article is to detail the novel natural sources and the effects described during the last decade for 7-isopentenyloxycoumarin and what has been reported on the mechanisms of action underlying the observed biological activities of this oxyprenylated secondary metabolite. In view of the herein described data, suggestions on how to address future research on the abovementioned natural product and structurally related derivatives in the best ways according to the authors will be also provided. Full article

(This article belongs to the Special Issue Current Advances in Medicinal Phytochemistry—A Themed Issue in Honour of Professor Simon Gibbons)

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