Three Pairs of New Isopentenyl Dibenzo[b,e]oxepinone Enantiomers from Talaromyces flavus, a Wetland Soil-Derived Fungus

Three pairs of new isopentenyl dibenzo[b,e]oxepinone enantiomers, (+)-(5S)-arugosin K (1a), (-)-(5R)-arugosin K (1b), (+)-(5S)-arugosin L (2a), (-)-(5R)-arugosin L (2b), (+)-(5S)-arugosin M (3a), (-)-(5R)-arugosin M (3b), and a new isopentenyl dibenzo[b,e]oxepinone, arugosin N (4), were isolated fro...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2016-09, Vol.21 (9), p.1184
Main Authors: Sun, Tian-Yu, Kuang, Run-Qiao, Chen, Guo-Dong, Qin, Sheng-Ying, Wang, Chuan-Xi, Hu, Dan, Wu, Bing, Liu, Xing-Zhong, Yao, Xin-Sheng, Gao, Hao
Format: Article
Language:English
Subjects:
arugosins K–N
isopentenyl dibenzo[b,e]oxepinone
Oxepins - chemistry
Oxepins - isolation & purification
Soil Microbiology
Talaromyces - chemistry
Talaromyces flavus
wetland soil-derived fungus
Wetlands
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Summary:Three pairs of new isopentenyl dibenzo[b,e]oxepinone enantiomers, (+)-(5S)-arugosin K (1a), (-)-(5R)-arugosin K (1b), (+)-(5S)-arugosin L (2a), (-)-(5R)-arugosin L (2b), (+)-(5S)-arugosin M (3a), (-)-(5R)-arugosin M (3b), and a new isopentenyl dibenzo[b,e]oxepinone, arugosin N (4), were isolated from a wetland soil-derived fungus Talaromyces flavus, along with two known biosynthetically-related compounds 5 and 6. Among them, arugosin N (4) and 1,6,10-trihydroxy-8-methyl-2-(3-methyl-2-butenyl)-dibenz[b,e]oxepin-11(6H)-one (CAS: 160585-91-1, 5) were obtained as the tautomeric mixtures. The structures of isolated compounds were determined by detailed spectroscopic analysis. In addition, the absolute configurations of these three pairs of new enantiomers were determined by quantum chemical ECD calculations.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules21091184