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

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

43 Citations (Scopus)

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

Fingerprint

Melastomataceae
Benzoquinones
Suriname
Miconia
benzoquinones
structure-activity relationships
Structure-Activity Relationship
rain forests
Quinones
synthesis
Cytotoxicity
Yeast
Inhibitory Concentration 50
quinones
Cells
inhibitory concentration 50
cytotoxicity
cell lines
Fractionation
Bioactivity

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Isolation, synthesis, and structure - Activity relationships of bioactive benzoquinones from Miconia lepidota from the suriname rainforest. / Gunatilaka, Leslie; Berger, John M.; Evans, Randy; Miller, James S.; Wisse, Jan H.; Neddermann, Kim M.; Bursuker, Isia; Kingston, David G I.

In: Journal of Natural Products, Vol. 64, No. 1, 2001, p. 2-5.

Research output: Contribution to journalArticle

Gunatilaka, Leslie ; Berger, John M. ; Evans, Randy ; Miller, James S. ; Wisse, Jan H. ; Neddermann, Kim M. ; Bursuker, Isia ; Kingston, David G I. / Isolation, synthesis, and structure - Activity relationships of bioactive benzoquinones from Miconia lepidota from the suriname rainforest. In: Journal of Natural Products. 2001 ; Vol. 64, No. 1. pp. 2-5.
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