Phytochemistry2022，Vol.1948.DOI:10.1016/j.phytochem.2021.113004

Structures of ganorbifates C-I, seven previously undescribed lanostanoids from the mushroom Ganoderma orbiforme, and insights of computed biosynthesis with DFT

Yin, Xia Yu, Chao Tuong, Thi M. L. Kou, Rong-Wei Yang, An-An Chen, Xin Wang, Wen Ji Gao, Yu-Qi Gao, Jin-Ming
Phytochemistry2022，Vol.1948.DOI:10.1016/j.phytochem.2021.113004
✕
  • NSTL
  • Elsevier

Structures of ganorbifates C-I, seven previously undescribed lanostanoids from the mushroom Ganoderma orbiforme, and insights of computed biosynthesis with DFT

Yin, Xia 1Yu, Chao 1Tuong, Thi M. L. 1Kou, Rong-Wei 1Yang, An-An 1Chen, Xin 1Wang, Wen Ji 1Gao, Yu-Qi 2Gao, Jin-Ming1
扫码查看

作者信息

  • 1. Northwest A&F Univ
  • 2. Northwest Univ
  • 折叠

Abstract

Ganorbifates C-I, seven undescribed biosynthetically related polyoxygenated 3,4-seco-27-norlanostanoid congeners, were isolated from the edible mushroom, Ganoderma orbiforme. Ganorbifate C features a unique cyclo-butene ring constructed at C19/C11, and both D and E incorporate an unusual cyclopropane ring formed by C -19/C-9 linkage. Their structures, including the absolute configurations, were determined by spectroscopic methods and ECD calculations. The proposed Norrish-Yang cyclization-based key biosynthetic pathway for ganorbifates C-E is revealed by density functional theory (DFT) calculations. The computational studies uncover the formation of both cyclobutene and cyclopropane rings in the isolates and the stereoselectivity centers of these steps are consistent with those in the natural products. All compounds exhibited NO generation inhibition in LPS-induced BV-2 microglial cells, among them ganorbifate C was the most promising one with the IC50 values of 4.37 mu M.

Key words

Ganoderma orbiforme/Ganodermataceae/3/4-seco-27-norlanostanoid/Norrish-Yang cyclization/anti-neuroinflammatory activities/3/4-SECO-27-NORLANOSTANE TRITERPENES/BONINENSE

引用本文复制引用

出版年

2022
Phytochemistry

Phytochemistry

CCR
ISSN：0031-9422
被引量1
参考文献量23
段落导航相关论文