Sarglaromatics A–E: A Class of Naphthalene-Like Architecture Fused Norlindenane Sesquiterpene Dimers from <i>Sarcandra glabra</i>
Yunpeng Sun, Jun Chi, Lv-Jun Zhang, Siyuan Wang, Zhenhao Chen, Hao Zhang, Lingyi Kong, Jun Luo
Abstract
Sarglaromatics A–E (1–5, respectively), five unprecedented naphthalene-like architecture-fused norlindenane sesquiterpene dimers, were discovered from the roots of Sarcandra glabra. The unique naphthalene core skeleton was obtained from classical lindenane [4 + 2] dimers via a free-radical-mediated C11–C11′ bond formation reaction and 12'-decarboxylation. The highly fused octonary ring skeleton was elucidated by HRMS, NMR, ECD, quantum chemical calculations, and biogenetic inspiration. Compounds 1 and 2 showed significant anti-nonalcoholic steatohepatitis (NASH) activity by inhibiting lipid deposition in L02 cells.
Topics & Concepts
ChemistryNaphthaleneSesquiterpeneDecarboxylationQuantum chemicalStereochemistryRing (chemistry)MoleculeOrganic chemistryCatalysisPhytochemistry and Biological ActivitiesSesquiterpenes and Asteraceae StudiesNatural product bioactivities and synthesis