Furanoaustinol and 7-acetoxydehydroaustinol: new meroterpenoids from a marine-derived fungal strain Penicillium sp. SF-5497

The Journal of Antibiotics
Jin-Soo ParkHyuncheol Oh

Abstract

Two new meroterpenoid-type fungal metabolites, furanoaustinol (1) and 7-acetoxydehydroaustinol (2), were isolated from the ethyl acetate extract of a marine-derived fungal strain Penicillium sp. SF-5497, along with eight (3-10) known meroterpenoids. Their structures were elucidated mainly based on the analysis of their NMR (1D and 2D) and MS data. Particularly, the novel meroterpenoid, furanoaustinol (1), belonging to the austin group, was identified to possess an unprecedented hexacyclic ring system. Biological evaluation of these compounds revealed that furanoaustinol (1) weakly inhibited the activity of protein tyrosine phosphatase 1B in a dose-dependent manner with an IC50 value of 77.2 μM. In addition, 7-acetoxydehydroaustinol (2) and four other known meroterpenoids (5, 7, 9, and 10) weakly suppressed the overproduction of nitric oxide in lipopolysaccharide-challenged BV2 microglial cells with IC50 values of 61.0, 30.1, 58.3, 37.6, and 40.2 μM, respectively.

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Citations

Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Jun 24, 2020·Marine Drugs·Minghua JiangSenhua Chen
Nov 14, 2019·Marine Drugs·Jianzhou XuShan He
Dec 16, 2020·Organic & Biomolecular Chemistry·Minghua JiangSenhua Chen
Feb 10, 2021·Marine Drugs·Anton N YurchenkoEkaterina A Yurchenko
Jul 22, 2021·Journal of Natural Products·Meng BaiGuang-Ying Chen
Apr 17, 2019·Journal of Natural Products·Meng BaiGuang-Ying Chen

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Datasets Mentioned

BETA
KU341382

Methods Mentioned

BETA
nuclear magnetic resonance
NMR
X-ray
column
ELISA

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