ol6b03064_si_001.cif (4.04 kB)
(±)-Ganoapplanin, a Pair of Polycyclic Meroterpenoid Enantiomers from Ganoderma applanatum
dataset
posted on 2016-11-18, 18:33 authored by Lei Li, Huan Li, Xing-Rong Peng, Bo Hou, Mu-Yuan Yu, Jin-Run Dong, Xiao-Nian Li, Lin Zhou, Jian Yang, Ming-Hua Qiu(±)-Ganoapplanin
(1), a pair of novel meroterpenoid
enantiomers featuring an unprecedented dioxaspirocyclic skeleton constructed
from a 6/6/6/6 tetracyclic system and an unusual tricyclo[4.3.3.03′,7′]dodecane motif, were isolated from Ganoderma applanatum. Its structure and absolute configurations
were determined by spectroscopic analyses, X-ray crystallography,
and ECD (electronic circular dichroism calculations). A plausible
biogenetic pathway, involving a key Gomberg–Bachmann reaction,
was also proposed for (±)-1. Biological studies
showed that (±)-1 and its enantiomers exhibited
different inhibitory activities on T-type voltage-gated calcium channels.
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dodecanemotifGanoapplaninBiological studiesGanoderma applanatumdioxaspirocyclic skeletondichroism calculationsspectroscopic analysesPolycyclic Meroterpenoid EnantiomersGombergnovel meroterpenoid enantiomersT-type voltage-gated calcium channelsbiogenetic pathwayECDX-ray crystallographyconfigurationtricyclotetracyclic
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