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Molecules
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Terpenoid Natural Products: Discovery, Biological Evaluation, and Structural Modification
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Terpenoid Natural Products: Discovery, Biological Evaluation, and Structural Modification

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

Deadline for manuscript submissions: closed (31 October 2023) | Viewed by 3148

Special Issue Editors

Dr. Zheng-Hong Pan

E-Mail Website
Guest Editor
Guangxi Key Laboratory of Plant Functional Phytochemicals and Sustainable Utilization, Guangxi Institute of Botany, Chinese Academy of Sciences, Guilin 541006, China
Interests: structural identification; phytochemistry; natural products
Dr. Xing-De Wu

E-Mail Website
Guest Editor
Key Laboratory of Ethnic Medicine Resource Chemistry, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming 650500, China
Interests: bioactive natural products; phytochemistry; medicinal natural products; structural modification

Special Issue Information

Dear Colleagues,

Terpenoids represent the largest and most diverse class of natural products produced by plants, higher fungi, insects, microbes, and marine organisms. They have a variety of biological activities, such as antitumor, anti-inflammatory, antimalarial, antidiabetes, and antifungal properties. Additionally, some terpenoids and their derivatives have been developed into drugs for clinical use.

This Special Issue welcomes both original articles and reviews focusing on chemical and biological research on terpenoids from natural resources. The articles may cover the isolation, structure identification, and biological evaluation of newly identified compounds from natural resources, as well as structural modification, pharmacology, and mechanism of action of known bioactive terpenoids. We hope that this Special Issue will increase our understanding of bioactive terpenoid natural products, and we would like to thank the authors in advance for their valuable contributions.

Dr. Zheng-Hong Pan
Dr. Xing-De Wu
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • terpenoids
  • biological activities
  • natural products
  • synthetic derivatives
  • structural modification
  • mechanism of action
  • natural resources

Published Papers (3 papers)

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Research

17 pages, 1649 KiB  
Article
Biotransformation of Ursonic Acid by Aspergillus ochraceus and Aspergillus oryzae to Discover Anti-Neuroinflammatory Derivatives
by Yan-Ni Wu, Dan Su, Jia Yang, Ying Yi, An-Dong Wang, Min Yang, Jian-Lin Li, Bo-Yi Fan, Guang-Tong Chen, Wen-Li Wang and Bai Ling
Molecules 2023, 28(24), 7943; https://doi.org/10.3390/molecules28247943 - 05 Dec 2023
Viewed by 678
Abstract
Biotransformation of ursonic acid (1) by two fungal strains Aspergillus ochraceus CGMCC 3.5324 and Aspergillus oryzae CGMCC 3.407 yielded thirteen new compounds (4, 5, 7–10, and 13–19), along with five recognized ones. [...] Read more.
Biotransformation of ursonic acid (1) by two fungal strains Aspergillus ochraceus CGMCC 3.5324 and Aspergillus oryzae CGMCC 3.407 yielded thirteen new compounds (4, 5, 7–10, and 13–19), along with five recognized ones. The structural details of new compounds were determined through spectroscopic examination (NMR, IR, and HR-MS) and X-ray crystallography. Various modifications, including hydroxylation, epoxidation, lactonization, oxygen introduction, and transmethylation, were identified on the ursane core. Additionally, the anti-neuroinflammatory efficacy of these derivatives was assessed on BV-2 cells affected by lipopolysaccharides. It was observed that certain methoxylated and epoxylated derivatives (10, 16, and 19) showcased enhanced suppressive capabilities, boasting IC50 values of 8.2, 6.9, and 5.3 μM. Such ursonic acid derivatives might emerge as potential primary molecules in addressing neurodegenerative diseases. Full article
(This article belongs to the Special Issue Terpenoid Natural Products: Discovery, Biological Evaluation, and Structural Modification)
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13 pages, 4891 KiB  
Article
New Tricholomalides D–G from the Mushroom Tricholoma ustaloides Grown in an Italian Beech Wood
by Gianluca Gilardoni, Francesca Negri, Paola Vita Finzi, Faiq H. S. Hussain and Giovanni Vidari
Molecules 2023, 28(21), 7446; https://doi.org/10.3390/molecules28217446 - 06 Nov 2023
Viewed by 750
Abstract
Four novel seconeodolastane diterpenoids, named tricholomalides D–G, were isolated, together with the known tricholomalide C, from the fruiting bodies of Tricholoma ustaloides Romagn., a species belonging to the large Tricholoma genus of higher mushrooms (Basidiomycota, family Tricholomataceae). They were isolated [...] Read more.
Four novel seconeodolastane diterpenoids, named tricholomalides D–G, were isolated, together with the known tricholomalide C, from the fruiting bodies of Tricholoma ustaloides Romagn., a species belonging to the large Tricholoma genus of higher mushrooms (Basidiomycota, family Tricholomataceae). They were isolated through multiple chromatographic separations, and the structures, including the absolute configuration, were established through a detailed analysis of MS, NMR, and CD spectral data and comparison with related compounds reported in the literature, which has been thoroughly revised. Full article
(This article belongs to the Special Issue Terpenoid Natural Products: Discovery, Biological Evaluation, and Structural Modification)
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25 pages, 4861 KiB  
Article
Synthesis of Tricyclic Pterolobirin H Analogue: Evaluation of Anticancer and Anti-Inflammatory Activities and Molecular Docking Investigations
by Houda Zentar, Fatin Jannus, Marta Medina-O’Donnell, Az-eddine El Mansouri, Antonio Fernández, José Justicia, Enrique Alvarez-Manzaneda, Fernando J. Reyes-Zurita and Rachid Chahboun
Molecules 2023, 28(17), 6208; https://doi.org/10.3390/molecules28176208 - 23 Aug 2023
Viewed by 1117
Abstract
Pterolobirin H (3), a cassane diterpene isolated from the roots of Pterolobium macropterum, exhibits important anti-inflammatory and anticancer properties. However, its relatively complex tetracyclic structure makes it difficult to obtain by chemical synthesis, thus limiting the studies of its biological activities. [...] Read more.
Pterolobirin H (3), a cassane diterpene isolated from the roots of Pterolobium macropterum, exhibits important anti-inflammatory and anticancer properties. However, its relatively complex tetracyclic structure makes it difficult to obtain by chemical synthesis, thus limiting the studies of its biological activities. Therefore, we present here a short route to obtain a rational simplification of pterolobirin H (3) and some intermediates. The anti-inflammatory activity of these compounds was assayed in LPS-stimulated RAW 264.7 macrophages. All compounds showed potent inhibition of NO production, with percentages between 54 to 100% at sub-cytotoxic concentrations. The highest anti-inflammatory effect was shown for compounds 15 and 16. The simplified analog 16 revealed potential NO inhibition properties, being 2.34 higher than that of natural cassane pterolobirin H (3). On the other hand, hydroxyphenol 15 was also demonstrated to be the strongest NO inhibitor in RAW 264.7 macrophages (IC50 NO = 0.62 ± 0.21 μg/mL), with an IC50NO value 28.3 times lower than that of pterolobirin H (3). Moreover, the anticancer potential of these compounds was evaluated in three cancer cell lines: HT29 colon cancer cells, Hep-G2 hepatoma cells, and B16-F10 murine melanoma cells. Intermediate 15 was the most active against all the selected tumor cell lines. Compound 15 revealed the highest cytotoxic effect with the lowest IC50 value (IC50 = 2.45 ± 0.29 μg/mL in HT29 cells) and displayed an important apoptotic effect through an extrinsic pathway, as evidenced in the flow cytometry analysis. Furthermore, the Hoechst staining assay showed that analog 15 triggered morphological changes, including nuclear fragmentation and chromatin condensation, in treated HT29 cells. Finally, the in silico studies demonstrated that cassane analogs exhibit promising binding affinities and docking performance with iNOS and caspase 8, which confirms the obtained experimental results. Full article
(This article belongs to the Special Issue Terpenoid Natural Products: Discovery, Biological Evaluation, and Structural Modification)
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