Isolation, synthesis, and structure - Activity relationships of bioactive benzoquinones from Miconia lepidota from the suriname rainforest

A. A. Leslie Gunatilaka, John M. Berger, Randy Evans, James S. Miller, Jan H. Wisse, Kim M. Neddermann, Isia Bursuker, David G.I. Kingston

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

Bioactivity-directed fractionation of an EtOAc extract from the leaves of Miconia lepidota afforded the two benzoquinones 2-methoxy-6-heptyl-1,4-benzoquinone (1) and 2-methoxy-6-pentyl-1,4-benzoquinone (primin) (2). This is the first reported isolation of 1. Both quinones 1 and 2 exhibited activity toward mutant yeast strains based on Saccharomyces cerevisiae, indicative of their cytotoxicity and potential anticancer activity. A number of previously synthesized and new analogues were prepared and tested in the same strains. Compounds 1, 2, 2-methoxy-6-butyl-1,4-benzoquinone (5), and 2-methoxy-6-decyl-1,4-benzoquinone (6) were tested in two cytotoxicity assays. In the M109 tumor cell lines, quinones 1, 2, and 6 had an IC50 value of 10 μg/mL. In the A2780 cell line, compounds 1, 2 and 5 had IC50 values of 7.9, 2.9, and 3.2/ μg/mL, respectively.

Original languageEnglish (US)
Pages (from-to)2-5
Number of pages4
JournalJournal Of Natural Products
Volume64
Issue number1
DOIs
StatePublished - 2001

ASJC Scopus subject areas

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

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