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 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.
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China. sty4048588@163.com.
Tian-Yu
TY
Sun
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China. bridgekuang@163.com.
Run-Qiao
RQ
Kuang
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China. chgdtong@163.com.
Guo-Dong
GD
Chen
Clinical Experimental Center, First Affiliated Hospital of Jinan University, Guangzhou 510632, China. qinshengying78@163.com.
Sheng-Ying
SY
Qin
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China. wcxjnu@163.com.
Chuan-Xi
CX
Wang
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China. thudan@jnu.edu.cn.
Dan
D
Hu
State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, China. wubing@im.ac.cn.
Bing
B
Wu
State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, China. liuxz@sun.im.ac.cn.
Xing-Zhong
XZ
Liu
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China. tyaoxs@jnu.edu.cn.
Xin-Sheng
XS
Yao
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China. tghao@jnu.edu.cn.
Hao
H
Gao
D010082:Oxepins / Q000737:chemistry / Q000302:isolation & purification; D012988:Soil Microbiology; D032901:Talaromyces / Q000737:chemistry*; D053833:Wetlands
D010082:Oxepins
Talaromyces flavus; arugosins K–N; isopentenyl dibenzo[b,e]oxepinone; wetland soil-derived fungus