Scaparvin A, a novel caged cis-clerodane with an unprecedented C-6/C-11 bond, and related diterpenoids from the liverwort Scapania parva.
A novel caged cis-clerodane diterpenoid, scaparvin A, possessing an unprecedented C-6/C-11 bond and a ketal ring, as well as four new cis-clerodane derivatives, scaparvins B-E, were isolated from the Chinese liverwort Scapania parva. Their absolute structures were elucidated by analysis of NMR and CD data coupled with electronic circular dichroism (ECD) calculations. It was proposed that an enzymatic intramolecular aldol reaction was the key step in the biogenetic pathway of scaparvin A.
Guo
Dong-Xiao
DX
Department of Natural Products Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan 250012, PR China.
Zhu
Rong-Xiu
RX
Wang
Xiao-Ning
XN
Wang
Li-Ning
LN
Wang
Shu-Qi
SQ
Lin
Zhao-Min
ZM
Lou
Hong-Xiang
HX
D002244:Carbon / Q000737:chemistry*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D045785:Diterpenes, Clerodane / Q000737:chemistry* / Q000494:pharmacology; D035926:Hepatophyta / Q000737:chemistry*; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure
D045785:Diterpenes, Clerodane; C554706:scaparvin A; D002244:Carbon