title: (±)-Ganoapplanin, a Pair of Polycyclic Meroterpenoid Enantiomers from Ganoderma applanatum.
abstract: (±)-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.
authors.affiliation: Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.|Graduate University of the Chinese Academy of Sciences , Beijing 100049, People's Republic of China.
authors.forename: Lei
authors.initials: L
authors.lastname: Li
authors.affiliation: Graduate University of the Chinese Academy of Sciences , Beijing 100049, People's Republic of China.|Key Laboratory of Animal Models and Human Disease Mechanisms, and Ion Channel Research and Drug Development Center, Kunming Institute of Zoology, Chinese Academy of Sciences , Kunming 650223, People's Republic of China.
authors.forename: Huan
authors.initials: H
authors.lastname: Li
authors.affiliation: Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.
authors.forename: Xing-Rong
authors.initials: XR
authors.lastname: Peng
authors.affiliation: Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.|Graduate University of the Chinese Academy of Sciences , Beijing 100049, People's Republic of China.
authors.forename: Bo
authors.initials: B
authors.lastname: Hou
authors.affiliation: Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.|Graduate University of the Chinese Academy of Sciences , Beijing 100049, People's Republic of China.
authors.forename: Mu-Yuan
authors.initials: MY
authors.lastname: Yu
authors.affiliation: Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.|Graduate University of the Chinese Academy of Sciences , Beijing 100049, People's Republic of China.
authors.forename: Jin-Run
authors.initials: JR
authors.lastname: Dong
authors.affiliation: Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.
authors.forename: Xiao-Nian
authors.initials: XN
authors.lastname: Li
authors.affiliation: Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.
authors.forename: Lin
authors.initials: L
authors.lastname: Zhou
authors.affiliation: Key Laboratory of Animal Models and Human Disease Mechanisms, and Ion Channel Research and Drug Development Center, Kunming Institute of Zoology, Chinese Academy of Sciences , Kunming 650223, People's Republic of China.
authors.forename: Jian
authors.initials: J
authors.lastname: Yang
authors.affiliation: Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.|Graduate University of the Chinese Academy of Sciences , Beijing 100049, People's Republic of China.
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Qiu
mesh_terms: D002121:Calcium Channel Blockers / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D020747:Calcium Channels, T-Type / Q000378:metabolism*; D018360:Crystallography, X-Ray; D032902:Ganoderma / Q000737:chemistry*; D057809:HEK293 Cells; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification / Q000493:pharmacokinetics*
chemical_list: D002121:Calcium Channel Blockers; D020747:Calcium Channels, T-Type; D013729:Terpenes; C000627545:ganoapplanin