Bergamotane Sesquiterpenes with Alpha‐Glucosidase Inhibitory Activity from the Plant Pathogenic Fungus <i>Penicillium expansum</i>

Ying, You‐Min; Fang, Cheng-An; Yao, Feng-Qi; Yu, Yuan; Shen, Yin‐Chu; Hou, Zhuo-Ni; Wang, Zhen; Zhang, Wei; Shan, Wei‐Guang; Zhan, Zha‐Jun

doi:10.1002/cbdv.201600184

Cited by 26 publications

(30 citation statements)

References 15 publications

(33 reference statements)

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“…The biosynthesis of the isolated compounds 1−18 and 20−23 was proposed as shown in Scheme 1. Bergamotane sesquiterpenoids, bearing a borneol ring system or a β-pinene ring system, are naturally occurring in plants and fungi (Scheme 1) [9,[14][15][16][17][29][30][31][32][33][34]. In this study, compounds 1 and 2 possess a rare carbon skeleton while the methyl group (C-14) in 2 had a further 1,2-migration.…”

Section: Resultsmentioning

confidence: 68%

“…Therefore, it is necessary to conduct systematic chemical component mining and biological activity evaluation on this mushroom. In this study, a total of 23 sesquiterpenoids (1-23, Figure 1) including eighteen new bergamotane-type ones, namely craterodoratins A-R (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18), and one new victoxinine derivative, namely craterodoratin S (19), were isolated from C. odoratus. Their structures with absolute configurations were elucidated by extensive spectroscopic methods (including 1D and 2D NMR, MS, UV, and IR technologies), single-crystal X-ray diffraction analysis, as well as NMR and ECD calculations.…”

Section: Introductionmentioning

confidence: 99%

“…Their structures with absolute configurations were elucidated by extensive spectroscopic methods (including 1D and 2D NMR, MS, UV, and IR technologies), single-crystal X-ray diffraction analysis, as well as NMR and ECD calculations. Previous pharmacological studies on bergamotane metabolites have demonstrated α-glucosidase inhibitory activity [14], antibacterial activity [9,15,16], inhibition of pancreatic lipase [17], and phytotoxic effects against Johnson grass and Sorghum [18][19][20][21]. In this study, all compounds were evaluated for their cytotoxic activities against five human cancer cell lines, and for their immunosuppressive activity on T-cell and B-cell proliferation.…”

Section: Introductionmentioning

confidence: 99%

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Immunosuppressive Sesquiterpenoids from the Edible Mushroom Craterellus odoratus

Quan

Zhang

et al. 2021

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The aim of this work was to comprehensively understand the chemical constituents of the edible mushroom Craterellus ordoratus and their bioactivity. A chemical investigation on this mushroom led to the isolation of 23 sesquiterpenoids including eighteen previously undescribed bergamotane sesquiterpenes, craterodoratins A–R (1–18), and one new victoxinine derivative, craterodoratin S (19). The new structures were elucidated by detailed interpretation of spectrometric data, theoretical nuclear magnetic resonance (NMR) and electronic circular dichroism (ECD) calculations, and single-crystal X-ray crystallographic analysis. Compounds 1 and 2 possess a ring-rearranged carbon skeleton. Compounds 3, 10, 12–15, 19, 20 and 23 exhibit potent inhibitory activity against the lipopolysaccharide (LPS)-induced proliferation of B lymphocyte cells with the IC50 values ranging from 0.67 to 22.68 μM. Compounds 17 and 20 inhibit the concanavalin A (ConA)-induced proliferation of T lymphocyte cell with IC50 values of 31.50 and 0.98 μM, respectively. It is suggested that C. ordoratus is a good source for bergamotane sesquiterpenoids, and their immunosuppressive activity was reported for the first time. This research is conducive to the further development and utilization of C. ordoratus.

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Section: Resultsmentioning

confidence: 68%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Immunosuppressive Sesquiterpenoids from the Edible Mushroom Craterellus odoratus

Quan

Zhang

et al. 2021

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“…Expansolides C 28 and D 29 were two new bergamotane sesquiterpene lactones isolated from the plant pathogenic fungus Penicillium expansum [28]. The epimeric mixture of expansolides C 28 and D 29 (in a ratio of 2:1 at the temperature of the bioassay) exhibited more potent α-glucosidase inhibitory activity (IC 50 0.50 mM) as compared with the positive control acarbose (IC 50 1.90 mM) in an in vitro bioassay.…”

Section: Bergamotane Spiroaminal and Spiroaxanementioning

confidence: 99%

Sesquiterpenoids Specially Produced by Fungi: Structures, Biological Activities, Chemical and Biosynthesis (2015–2020)

Quan

Zhang

Feng

2021

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Fungi are widely distributed in the terrestrial environment, freshwater, and marine habitat. Only approximately 100,000 of these have been classified although there are about 5.1 million characteristic fungi all over the world. These eukaryotic microbes produce specialized metabolites and participate in a variety of ecological functions, such as quorum detection, chemical defense, allelopathy, and maintenance of symbiosis. Fungi therefore remain an important resource for the screening and discovery of biologically active natural products. Sesquiterpenoids are arguably the richest natural products from plants and micro-organisms. The rearrangement of the 15 high-ductility carbons gave rise to a large number of different skeletons. At the same time, abundant structural variations lead to a diversification of biological activity. This review examines the isolation, structural determination, bioactivities, and synthesis of sesquiterpenoids that were specially produced by fungi over the past five years (2015–2020).

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“…Prior to the isolation of massarinolin A, only expansolides A and B (5 a, 5 b), a pair of C4 epimers, share the same tetracyclic ring system. [2] Later on, closely related molecules such as purpurolides B, D, and E (2, 3, and 4), [3] expansolides C and D (6 a, 6 b), [4] and decipienolides A and B (7 a, 7 b) [5] were isolated and characterized. Purpurolides C and F (8, 9) and eutypellacytosporins A-D [6] (10 a, 10 b, 11 a, 11 b) with higher oxidation state at C14 were isolated as well.…”

mentioning

confidence: 99%

Flow Chemistry‐Enabled Divergent and Enantioselective Total Syntheses of Massarinolin A, Purpurolides B, D, E, 2,3‐Deoxypurpurolide C, and Structural Revision of Massarinolin A

2021

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Massarinolin A and purpurolides are bioactive bergamotane sesquiterpenes condensed with a variety of synthetically challenging ring systems: a bicyclo[3.1.1]heptane, an oxaspiro[3.4]octane, and a dioxaspiro[4.4]nonane (oxaspirolactone). Herein, we report the first enantioselective total syntheses of massarinolin A, purpurolides B, D, E, and 2,3deoxypurpurolide C. Our synthesis and computational analysis also led to a structural revision of massarinolin A. The divergent approach features an enantioselective organocatalyzed Diels-Alder reaction to install the first stereogenic center in high ee, a scalable flow photochemical Wolff rearrangement to build the key bicyclo[3.1.1]heptane, a furan oxidative cyclization to form the oxaspirolactone, a late-stage allylic CÀH oxidation, and a Myers NBSH-promoted sigmatropic elimination to install the exo methylene group of massarinolin A.

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Bergamotane Sesquiterpenes with Alpha‐Glucosidase Inhibitory Activity from the Plant Pathogenic Fungus Penicillium expansum

Cited by 26 publications

References 15 publications

Immunosuppressive Sesquiterpenoids from the Edible Mushroom Craterellus odoratus

Immunosuppressive Sesquiterpenoids from the Edible Mushroom Craterellus odoratus

Sesquiterpenoids Specially Produced by Fungi: Structures, Biological Activities, Chemical and Biosynthesis (2015–2020)

Flow Chemistry‐Enabled Divergent and Enantioselective Total Syntheses of Massarinolin A, Purpurolides B, D, E, 2,3‐Deoxypurpurolide C, and Structural Revision of Massarinolin A

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