Structural Revisions of a Class of Natural Products: Scaffolds of Aglycon Analogues of Fusicoccins and Cotylenins Isolated from Fungi

Author:

Tang Ying1,Xue Yongbo2ORCID,Du Guang1,Wang Jianping2,Liu Junjun2,Sun Bin2,Li Xiao‐Nian3,Yao Guangmin2,Luo Zengwei2,Zhang Yonghui2

Affiliation:

1. Tongji Hospital, Tongji Medical College Huazhong University of Science and Technology Wuhan China

2. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College Huazhong University of Science and Technology Wuhan 430030 China

3. State Key Laboratory of Phytochemistry and Plant Resources in West China Chinese Academy of Sciences Kunming China

Abstract

AbstractThe reisolation and structural revision of brassicicene D is described, and inspired us to reassign the core skeletons of brassicicenes C–H, J and K, ranging from dicyclopenta[a,d]cyclooctane to tricyclo[9.2.1.03,7]tetradecane using quantum‐chemical predictions and experimental validation strategies. Three novel, highly modified fusicoccanes, brassicicenes L–N, were also isolated from the fungus Alternaria brassicicola, and their structures were unequivocally established by spectroscopic data, ECD calculations, and crystallography. The reassigned structures represent the first class of bridgehead double‐bond‐containing natural products with a bicyclo[6.2.1]undecane carbon skeleton. Furthermore, their stabilities were first predicted with olefin strain energy calculations. Collectively, these findings extend our view of the application of computational predictions and biosynthetic logic‐based structure elucidation to address problems related to the structure and stability of natural products.

Funder

Program for New Century Excellent Talents in University

State Education Ministry of China

National Natural Science Foundation of China

National Science and Technology Project of China

Publisher

Wiley

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