Premium
3,5‐Dimethylorsellinic Acid Derived Meroterpenoids from Eupenicillium sp. 6A‐9, a Fungus Isolated from the Marine Sponge Plakortis simplex
Author(s) -
Gu BinBin,
Wu Wei,
Liu LiYun,
Tang Jie,
Zeng YaJun,
Wang ShuPing,
Sun Fan,
Li Lei,
Yang Fan,
Lin HouWen
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701335
Subject(s) - sponge , chemistry , stereochemistry , fungus , ring (chemistry) , organic chemistry , botany , biology
Two rare 6(D)/5(E) ring‐fused meroterpenoids, eupeniacetal A ( 1 ) and eupeniacetal B ( 2 ), and three new meroterpenoids, 1‐methoxy‐hydropreaustinoid A1 ( 3 ), hydroberkeleyone B ( 4 ), and 22‐deoxy‐10‐oxominiolutelide B ( 5 ), as well as five known meroterpenoids, 22‐deoxyminiolutelide B ( 6 ), preaustinoid A1 ( 7 ), berkeleyone C ( 8 ), berkeleyacetal A ( 9 ), and preaustinoid A3 ( 10 ), have been isolated, through the aid of LC–MS, from the sponge‐derived fungus Eupenicillium sp. 6A‐9. The structures of these meroterpenoids were elucidated by detailed spectroscopic analysis, comparison with literature data, and single‐crystal X‐ray diffraction. The absolute configurations were assigned by means of TDDFT/ECD and [ α ] D calculations as well as by X‐ray diffraction analysis. These compounds showed inhibitory activity towards TNF‐α production in the induced THP‐1 cell line but were inactive against normal tumor cell lines.