Proversilins A–E, Drimane-Type Sesquiterpenoids from the Endophytic <i>Aspergillus versicolor</i>

Li, Huaqiang; Zhang, Runge; Cao, Fei; Wang, Jianping; Hu, Zhengxi; Zhang, Yonghui

doi:10.1021/acs.jnatprod.0c00298

Cited by 19 publications

(10 citation statements)

References 43 publications

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“…There have only been a few examples identified, including flavunoidine (16), aculene A (17), ergokonin A (18), and proversilin C (19) (Fig. 4a) (Lee et al 2019;Li et al 2020b;Yee et al 2019).…”

Section: Nrps-terpenoidsmentioning

confidence: 99%

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Peculiarities of meroterpenoids and their bioproduction

Han

Jiang

Zhang

et al. 2021

Appl Microbiol Biotechnol

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Meroterpenoids are a class of terpenoid-containing hybrid natural products with impressive structural architectures and remarkable pharmacological activities. Remarkable advances in enzymology and synthetic biology have greatly contributed to the elucidation of the molecular basis for their biosynthesis. Here, we review structurally unique meroterpenoids catalyzed by novel enzymes and unusual enzymatic reactions over the period of last five years. We also discuss recent progress on the biomimetic synthesis of chrome meroterpenoids and synthetic biology driven biomanufacturing of tropolone sesquiterpenoids, merochlorins, and plant-derived meroterpenoid cannabinoids. In particular, we focus on the novel enzymes involved in the biosynthesis of polyketide-terpenoids, nonribosomal peptide-terpenoids, terpenoid alkaloids, and meroterpenoid with unique structures. The biological activities of these meroterpenoids are also discussed. The information reviewed here might provide useful clues and lay the foundation for developing new meroterpenoid-derived drugs. Key points• Meroterpenoids possess intriguing structural features and relevant biological activities.• Novel enzymes are involved in the biosynthesis of meroterpenoids with unique structures.• Biomimetic synthesis and synthetic biology enable the construction and manufacturing of complex meroterpenoids.

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Section: Nrps-terpenoidsmentioning

confidence: 99%

“…Five new drimane-type sesquiterpenoids featuring an N-acetyl-β-phenylalanine moiety (one example proversilin C 19) were isolated from the endophytic fungus A. versicolor F210. Proversilin C showed moderate cytotoxic activity against human tumor HL-60 cells with an IC50 value of 7.3 µM (Li et al 2020b).…”

Section: Nrps-terpenoidsmentioning

confidence: 99%

Peculiarities of meroterpenoids and their bioproduction

Han

Jiang

Zhang

et al. 2021

Appl Microbiol Biotechnol

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“…(2019) SW620 08.63 ± 0.15 μM HCT116 09.03 ± 0.61 μM CaCo2 12.56 ± 0.91 μM SMMC-7721 27.66 ± 0.88 μM A-549 37.06 ± 2.24 μM MCF-7 27.89 ± 0.70 μM Isopenicin B (68) SW480 11.60 ± 0.18 μM SW620 15.48 ± 1.39 μM HCT116 14.95 ± 0.22 μM CaCo2 20.34 ± 0.25 μM SMMC-7721 33.49 ± 0.17 μM MCF-7 33.05 ± 0.19 μM Sesquiterpenoids Fumagillene A (69) MV4-11 8.40 ± 2.9 μg/mL Aspergillus fumigatus Ligusticum wallichii (T) China Li et al. (2020c) MDA-MB-231 14.3 ± 5.8 μg/mL Fumagillene B (70) MV4-11 11.2 ± 3.6 μg/mL MDA-MB-231 17.3 ± 6.4 μg/mL Proversilin C (71) HL-60 7.30 ± 1.2 μM Aspergillus versicolor F210 Lycoris radiata (T) China Li et al. (2020d) SMMC-7721 12.6 ± 0.9 μM A-549 15.0 ± 0.8 μM MCF-7 11.8 ± 0.5 μM SW-480 12.4 ± 0.4 μM Proversilin E (72) HL-60 9.90 ± 1.4 μM SMMC-7721 19.4 ± 0.7 μM A-549 28.4 ± 1.2 μM MCF-7 18.3 ± 1.2 μM SW-480 16.4 ± 1.0 μM Lithocarin B (73) SF-268 41.68 ± 0.88 μM Diaporthe lithocar...…”

Section: Cytotoxic Secondary Metabolites From Endophytic Fungimentioning

confidence: 99%

“…Proversilin C (71) and Proversilin E (72) are unprecedented drimane-type sesquiterpenoids which were obtained from fungi Aspergillus versicolor F210, an endophyte associated with Lycoris radiata . Both the compounds showed antiproliferation activity against HL-60, SMMC-7721, A-549, MCF-7 and SW-480 cells with IC 50 s of 7.3 ± 1.2, 12.6 ± 0.9, 15.0 ± 0.8, 11.8 ± 0.5, 12.4 ± 0.4 μM and 9.9 ± 1.4, 19.4 ± 0.7, 28.4 ± 1.2, 18.3 ± 1.2, 16.4 ± 1.0 μM respectively, while remain inactive against normal colonic epithelial cells (NCM460) with IC 50 of >40 μM ( Li et al., 2020d ). Two new eremophilane sesquiterpenes, Lithocarin B (73) and Lithocarin C (74) have been extracted along with two more new metabolites from EtOAc extract of fungus Diaporthe lithocarpus A740, an endophyte associated with medicinal plant Morinda officinalis .…”

Section: Cytotoxic Secondary Metabolites From Endophytic Fungimentioning

confidence: 99%

Endophytic fungi: A treasure trove of novel anticancer compounds

Prajapati

Goswami

Rawal

2021

Current Research in Pharmacology and Drug Discovery

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Cancer is a multifactorial disease with a convoluted genesis and progression. The emergence of multidrug resistance to presently be offered drug and relapse is by far, the most critical concern to tackle this deteriorating disease. Henceforth, there is undeniably an inflated necessity for safe, promising, and less harmful new anticancer drugs. Natural compounds from various sources like plants, animals, and microorganisms have occupied a center stage in drug discovery due to their tremendous chemical diversity and potential as therapeutic agents. Endophytic microbes are symbiotically associated with plants and have been proven to produce novel or analogues of host bioactive metabolites exhibiting a variety of biological activities including anticancer activity. This review emphasizes on structurally diverse unprecedented anticancer natural compounds that have been reported exclusively from endophytic fungi from 2016 to 2020. It covers chemical nature of metabolites, its fungal source associated with terrestrial, as well as marine plants and anticancer activity based on their cytotoxicity profile against various cancer cell lines. Many of these fungal metabolites with promising anticancer activity can be used as lead molecules for in silico experiments and deserve special attention from scientists for further in vitro and clinical research.

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“…The in vitro cytotoxic effect of the pure metabolites was studied against human tumour SW‐480, MCF‐7, A‐549, SMMC‐7721 and HL‐60 cell lines, in addition to NCM460 (the normal colonic epithelial cells). Compounds ( 119 ) and ( 121 ) have moderately inhibited the growth of HL‐60 cells, with IC 50 values of 7.3 to 9.9 μmol l −1 , respectively (Li et al 2020b).…”

Section: Introductionmentioning

confidence: 99%

The endophytic Aspergillus strains: A bountiful source of natural products

Hagag

Abdelwahab

El-kader

et al. 2022

Journal of Applied Microbiology

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Fungi that invade plant inner tissues without inducing disease symptoms are known as fungal endophytes. They represent a promising and tremendous reservoir of natural products with valuable biological potentials for application in medicine, agriculture and industry. Among the numerous existing endophytic fungi, Aspergillus strains constitute one of the most prolific sources of secondary metabolites with diverse chemical classes and interesting biological activities. This review covers the literature of the year 2020, reporting the isolation of 202 compounds obtained from more than 10 different endophytic Aspergillus species associated with different host plants. Analysis and interpretation of the collected data revealed that chemical investigation of endophytes belonging to the genus Aspergillus may greatly contribute to the discovery of potential drug leads. The isolated metabolites were chemically various and exhibited diverse biological activities such as antibacterial, anti‐cancer, anti‐plasmodial, anti‐inflammatory, antioxidant, immunosuppressive and antifungal activities. Moreover, adoption of advanced technology in molecular biology together with modern chemical tools is anticipated to improve the discovery of new biopharmaceuticals from this valuable microbial world in the future.

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Proversilins A–E, Drimane-Type Sesquiterpenoids from the Endophytic Aspergillus versicolor

Cited by 19 publications

References 43 publications

Peculiarities of meroterpenoids and their bioproduction

Peculiarities of meroterpenoids and their bioproduction

Endophytic fungi: A treasure trove of novel anticancer compounds

The endophytic Aspergillus strains: A bountiful source of natural products

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