Biomimetic synthesis of two salmahyrtisanes: salmahyrtisol A and hippospongide A

J Org Chem. 2015 May 1;80(9):4566-72. doi: 10.1021/acs.joc.5b00420. Epub 2015 Apr 16.

Abstract

Sesterterpenes with a salmahyrtisane skeleton have been synthesized for the first time. (-)-Sclareol has been selected as a precursor for the synthesis of two novel natural products: salmahyrtisol A (1) and hippospongide A (2). Our results represent a biomimetic approach to obtaining salmahyrtisanes from hyrtiosanes. Salmahyrtisol A has shown an activity comparable to that of the standard anticancer drugs in the cell lines A549, HBL-100, HeLa, and SW1573.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Biomimetic Materials / chemical synthesis
  • Biomimetic Materials / chemistry
  • Biomimetic Materials / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Molecular Conformation
  • Sesterterpenes / chemical synthesis
  • Sesterterpenes / chemistry
  • Sesterterpenes / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Terpenes / chemical synthesis
  • Terpenes / chemistry
  • Terpenes / pharmacology*

Substances

  • Antineoplastic Agents
  • Sesterterpenes
  • Terpenes
  • hippospongide A
  • salmahyrtisol A