New sesquiterpenes from Sonchus transcaspicus

Yi Feng Han, Qi Zhang, Kun Cao, Zhong Jian Jia

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Four new eudesmanolides were isolated from the whole plant of Sonchus transcaspicus and their structures were elucidated by means of spectroscopic methods, including 2D-NMR (1H-1H COSY, HMQC, HMBC and NOESY) and NOEDS (NOE difference spectra) as 1β-O-β-D-glucopyranosyl- 5α,6βH-eudesma-3-en-12,6α-olide (1), 1β-O-β-D- glucopyranosyl-15-O-(p-hydroxyphenylacetyl)-5α,6βH-eudesma-3,11(13) -dien-12,6α-olide (2), 1β-O-β-D-glucopyranosyl-(6′-O-p- hydroxyphenyl acetate)-15-O-(p-hydroxyphenylacetyl)-5α,6βH-eudesma-3, 11(13)-dien-12,6α-olide (3) and 1β-hydroxy-15-O-(p- methoxyphenylacetyl)-5α,6βH-eudesma-3,11(13)-dien-12,6α-olide (4). Compounds 1, 2 and 3 showed antibacterial activity against Escherichia coli and Staphylococcus aureus cells. Compounds 2 and 3 were evaluated for their in vitro cytotoxic activity against cultured SMMC-7721 (human hepatoma), HELA (human cervical carcinoma) and B-16 (murine melanoma) cells. The IC50 values for 2 were 108.0, 161.1 and 203.0 μM and those for 3 were 74.1, 117.3 and 135.0 μM, respectively. The structure-activity relationship is discussed.

Original languageEnglish (US)
Pages (from-to)543-547
Number of pages5
JournalPlanta Medica
Volume71
Issue number6
DOIs
StatePublished - Jun 2005

Keywords

  • Antibacterial activity
  • Compositae
  • Cytotoxic activity
  • Eudesmanolide
  • Sesquiterpene
  • Sonchus transcaspicus

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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