Dimericbiscognienyne A: A Meroterpenoid Dimer from Biscogniauxia sp. with New Skeleton and Its Activity

• DOI: 10.1021/acs.orglett.6b03264
• Publication Date: 2016-12-09T12:57:53Z
• Authors: Huan Zhao; Guo-Dong Chen; Jian Zou; Rong-Rong He; Sheng-Ying Qin; Dan Hu; Guo-Qiang Li; Liang-Dong Guo; Xin-Sheng Yao; Hao Gao
• Keywords: Models, Molecular; Amyloid beta-Peptides; Cycloaddition Reaction; Xylariales; Cell Survival; Terpenes; Diptera; Antineoplastic Agents; 01 natural sciences; Peptide Fragments; 0104 chemical sciences; 3. Good health; Structure-Activity Relationship; Alzheimer Disease; Cell Line, Tumor; Animals; Humans; Dimerization; Oxidation-Reduction

Dimericbiscognienyne A (1), an unusual diisoprenyl-cyclohexene-type meroterpenoid dimer, was isolated from Biscogniauxia sp. together with three new monomeric diisoprenyl-cyclohexene-type meroterpenoids (2-4) and one new isoprenyl-benzoic acid-type meroterpenoid (5). All structures were determined by extensive NMR spectroscopic methods, quantum chemical calculations, chemical derivatization, and X-ray crystallography. The formation of 1 is related to a unique intermolecular redox coupling Diels-Alder adduct reaction. Their cytotoxicities and short-term memory enhancement activities against Alzheimer's disease were assessed.