Bridged tricyclic sesquiterpenes from the tubercle nudibranch Phyllidia coelestis Bergh

J Nat Prod. 2013 Nov 22;76(11):2158-61. doi: 10.1021/np4007074. Epub 2013 Nov 7.

Abstract

A new sesquiterpene, 1-formamido-10(1→2)-abeopupukeanane (1), was isolated from the tubercle nudibranch Phyllidia coelestis Bergh, along with 2-formamidopupukeanane (2), which is reported here as a natural product for the first time. A rearrangement pathway toward the unprecedented tricyclo[4.4.0.0(2,8)]decane skeleton is proposed. Both compounds showed antiproliferative activity when targeting HeLa, MCF-7, KB, and HT-29 cancer cell lines in the range 0.05-10 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • Gastropoda / chemistry*
  • HT29 Cells
  • HeLa Cells
  • Humans
  • KB Cells
  • Molecular Structure
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Thailand

Substances

  • 1-formamido-10(1-2)-abeopupukeanane
  • 2-formamidopupukeanane
  • Antineoplastic Agents
  • Sesquiterpenes