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Benzopyran Derivatives and an Aliphatic Compound from a Mangrove Endophytic Fungus Penicillium citrinum QJF‐22
Author(s) -
Yang Wencong,
Chen Yan,
Cai Runlin,
Zou Ge,
Wang Bo,
She Zhigang
Publication year - 2020
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202000192
Subject(s) - penicillium citrinum , chemistry , benzopyran , stereochemistry , mangrove , fungus , penicillium , botany , biology , food science , ecology
Two new benzopyran derivatives, (2 R ,4 S )‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2 H ‐1‐benzopyran‐4‐ol and (2 S ,4 R ,2′ S ,4′ R )‐4,4′‐oxybis(5‐methoxy‐2‐methyl‐3,4‐dihydro‐2 H ‐1‐benzopyran), and a new aliphatic compound, (3 E ,5 Z ,8 S ,10 E )‐8‐hydroxytrideca‐3,5,10,12‐tetraen‐2‐one, together with three known benzopyran derivatives, were obtained from a mangrove endophytic fungus Penicillium citrinum QJF‐22 collected in Hainan island. Their structures were determined by analysis of spectroscopic data and the relative configuration of (2 R ,4 S )‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2 H ‐1‐benzopyran‐4‐ol was also confirmed by single‐crystal X‐ray diffraction. The absolute configurations of four compounds were established by comparison of ECD spectra to calculations. The configuration of (3 E ,5 Z ,8 S ,10 E )‐8‐hydroxytrideca‐3,5,10,12‐tetraen‐2‐one was confirmed by comparison of optical value to the similar compound. The configurations of the compounds (2 S ,4 S )‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2 H ‐1‐benzopyran‐4‐ol and (2 R ,4 R )‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2 H ‐1‐benzopyran‐4‐ol were first determined. (3 R ,4 S )‐3,4,8‐Trihydroxy‐3,4‐dihydronaphthalen‐1(2 H )‐one exhibited moderate inhibitory effects on LPS‐induced NO production in RAW264.7 cells with IC 50 of 44.7 μM, and without cytotoxicity to RAW264.7 cells within 50 μM.