Xishacorenes A-C, Diterpenes with Bicyclo[3.3.1]nonane Nucleus from the Xisha Soft Coral Sinularia polydactyla

Org Lett. 2017 Aug 18;19(16):4183-4186. doi: 10.1021/acs.orglett.7b01716. Epub 2017 Aug 1.

Abstract

Three new diterpenes, xishacorenes A-C, featuring an undescribed bicyclo[3.3.1]nonane nucleus bearing 1-vinyl and 13-[(E)-4-methylpenta-1,3-dien-1-yl] alkyl chains, and a related monocyclic known compound, were isolated from the Xisha soft coral Sinularia polydactyla. The structures of xishacorenes A-C, including their absolute configurations, were elucidated by extensive spectroscopic analysis and TDDFT ECD calculations. The new compounds exhibit an interesting dose-dependent promotion effect on the ConA-induced T lymphocyte proliferation. A plausible biosynthetic pathway of xishacorenes A-C is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Concanavalin A / metabolism
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Dose-Response Relationship, Drug
  • Models, Molecular
  • Molecular Structure
  • T-Lymphocytes / cytology
  • T-Lymphocytes / drug effects
  • T-Lymphocytes / immunology

Substances

  • Diterpenes
  • Concanavalin A