Uncommon Polyoxygenated Sesquiterpenoids from South China Sea Soft Coral Lemnalia flava

J Org Chem. 2019 Mar 15;84(6):3083-3092. doi: 10.1021/acs.joc.8b02912. Epub 2019 Mar 1.

Abstract

A detailed chemical investigation of the Chinese soft coral Lemnalia flava yielded four new nardosinane-type sesquiterpenoids (1-4), one new neolemnane-type sesquiterpenoid (5), and one new sesquiterpenoid with an uncommon 6/9 fused bicyclic skeleton (6), together with two known related compounds (7 and 8). The structures and absolute configurations of 1-8 were determined on the basis of extensive spectroscopic data analyses, X-ray diffraction analysis, chemical reactions, and computer-assisted structural elucidation including 13C NMR data calculation, residual dipolar coupling based NMR analysis, and time-dependent density functional theoryelectronic circular dichroism calculation. Plausible biogenetic pathways of two uncommon sesquiterpenoids (4 and 6) were proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa
  • China
  • Crystallography, X-Ray
  • Density Functional Theory
  • Models, Molecular
  • Molecular Conformation
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / metabolism

Substances

  • Sesquiterpenes