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Molecules 2016, 21(9), 1184; doi:10.3390/molecules21091184

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

1
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China
2
Clinical Experimental Center, First Affiliated Hospital of Jinan University, Guangzhou 510632, China
3
State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, China
*
Authors to whom correspondence should be addressed.
Academic Editors: Derek J. McPhee and Antigoni Kotali
Received: 12 August 2016 / Revised: 27 August 2016 / Accepted: 2 September 2016 / Published: 7 September 2016
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Abstract

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. View Full-Text
Keywords: isopentenyl dibenzo[b,e]oxepinone; wetland soil-derived fungus; Talaromyces flavus; arugosins K–N isopentenyl dibenzo[b,e]oxepinone; wetland soil-derived fungus; Talaromyces flavus; arugosins K–N
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Sun, T.-Y.; Kuang, R.-Q.; Chen, G.-D.; Qin, S.-Y.; Wang, C.-X.; Hu, D.; Wu, B.; Liu, X.-Z.; Yao, X.-S.; Gao, H. Three Pairs of New Isopentenyl Dibenzo[b,e]oxepinone Enantiomers from Talaromyces flavus, a Wetland Soil-Derived Fungus. Molecules 2016, 21, 1184.

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