Guaiane sesquiterpene lactones and amino acid-sesquiterpene lactone conjugates from the aerial parts of Saussurea pulchella

J Nat Prod. 2008 Apr;71(4):678-83. doi: 10.1021/np800005r. Epub 2008 Mar 4.

Abstract

Two new guaiane sesquiterpene lactones ( 1 and 2) and seven new amino acid-sesquiterpene lactone conjugates ( 3- 9), together with six known sesquiterpene lactones ( 10- 15), were isolated from the methanol extract of the aerial parts of Saussurea pulchella. Their structures were determined on the basis of spectroscopic and chemical methods to be 8alpha- O-(3'-hydroxy-3'-methylbutyryl)desacylcynaropicrin ( 1), 8alpha- O-(2', 3'-dihydroxyisobutyryl)11beta,13-dihydrodesacylcynaropicrin ( 2), and pulchellamines A, B, C, D, E, F, and G ( 3- 9). The structures of the new amino acid-sesquiterpene lactone conjugates, pulchellamines A, B, C, D, E, F, and G ( 3- 9), were confirmed by synthesis. The isolated compounds were evaluated for cytotoxic activity against four human tumor cell lines. Compounds 11 and 12 exhibited cytotoxicity against skin melanoma (SK-MEL-2) and ovary malignant ascites (SK-OV-3) human tumor cell lines with ED 50 values of 1.53 and 4.07 microM, and 2.49 and 7.42 microM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • Korea
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Saussurea / chemistry*
  • Sesquiterpenes, Guaiane / chemistry
  • Sesquiterpenes, Guaiane / isolation & purification*
  • Sesquiterpenes, Guaiane / pharmacology

Substances

  • 8alpha-O-(2',3'-dihydroxyisobutyryl)11beta,13-dihydrodesacylcynaropicrin
  • 8alpha-O-(3'-hydroxy-3'-methylbutyryl)desacylcynaropicrin
  • Antineoplastic Agents, Phytogenic
  • Lactones
  • Sesquiterpenes, Guaiane