Sarglaromatics A-E: A Class of Naphthalene-Like Architecture Fused Norlindenane Sesquiterpene Dimers from Sarcandra glabra

J Org Chem. 2022 Mar 18;87(6):4323-4332. doi: 10.1021/acs.joc.2c00014. Epub 2022 Mar 1.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Naphthalenes
  • Plant Roots / chemistry
  • Polymers
  • Sesquiterpenes* / chemistry

Substances

  • Naphthalenes
  • Polymers
  • Sesquiterpenes
  • naphthalene