Umbelactonyl cinnamate derivatives from Crypteronia paniculata that mediate DNA strand scission

Jing Zhen Deng, David J. Newman, Sidney M. Hecht

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

As part of an initiative to discover functional natural product analogues of bleomycin guided by the use of the COMPARE algorithm, a CH2Cl 2-MeOH extract prepared from Crypteronia paniculata was found to exhibit relaxation of supercoiled pSP64 DNA in the presence of Cu2+. Bioassay-guided fractionation employing a DNA strand scission assay resulted in the isolation of three novel DNA cleavage agents. Their structures were elucidated as umbelactonyl cinnamate derivatives 1-3 through their NMR and MS spectral data analyses. This is the first example of the isolation and structural characterization of naturally occurring umbelactonyl cinnamate derivatives. Compound 1 exhibited strong Cu2+-dependent relaxation of supercoiled pSP64 DNA, while compounds 2 and 3 had only weak DNA cleavage activity.

Original languageEnglish (US)
Pages (from-to)465-467
Number of pages3
JournalJournal of Natural Products
Volume68
Issue number3
DOIs
StatePublished - Mar 2005
Externally publishedYes

ASJC Scopus subject areas

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

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