Isolation, Structure Elucidation, and Absolute Configuration of Highly Oxygenated Germacranolides from Carpesium cernuum

J Nat Prod. 2016 Oct 28;79(10):2479-2486. doi: 10.1021/acs.jnatprod.6b00315. Epub 2016 Sep 26.

Abstract

The new highly oxygenated germacranolides cernuumolides A-J (1-10) and the known compounds 11-20 were isolated from Carpesium cernuum. Among these compounds, 1-4 are 11-methoxymethylgermacranolides and 5-7 as well as 11-17 are 2,9-hemiacetal-linked germacranolides. Their structures were elucidated using NMR and HRESIMS analyses, and X-ray diffraction studies were used to confirm the absolute configurations of 1, 2, 5, 6, 8, and 9. Cernuumolides A-J were evaluated for their in vitro cytotoxicity against the A549, HCT116, MDA-MB-231, and BEL7404 cell lines, and 8 exhibited moderate cytotoxicity with IC50 values in the 0.87-2.02 μM range.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Asteraceae / chemistry*
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • HCT116 Cells
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxygen / chemistry*
  • Sesquiterpenes, Germacrane / chemistry
  • Sesquiterpenes, Germacrane / isolation & purification*
  • Sesquiterpenes, Germacrane / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Sesquiterpenes, Germacrane
  • germacranolide
  • Oxygen