Structural Elucidation of Three 9,11- Seco Tetracyclic Triterpenoids Enables the Structural Revision of Euphorol J

J Org Chem. 2021 Jun 4;86(11):7588-7593. doi: 10.1021/acs.joc.1c00631. Epub 2021 May 20.

Abstract

Compounds 1-3, the rare examples of 9,11-seco euphane or lanostane triterpenoids featuring an enol-hemiacetal functionality, were isolated from Euphorbia stracheyi. Their structures were elucidated by a combination of spectroscopic, computational, chemical, and single-crystal X-ray diffraction means, which enables the structure of previously published euphorol J to be revised as 1. 1-3 showed significant cytotoxicities on the breast cancer cell line MDA-MB-468 with IC50 values in the range of 2.9-3.9 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Euphorbia*
  • Molecular Structure
  • Steroids
  • Triterpenes* / pharmacology

Substances

  • Steroids
  • Triterpenes