Isolation, Synthesis, and Structure−Activity Relationships of Bioactive Benzoquinones from Miconia lepidota from the Suriname Rainforest
2000; American Chemical Society; Volume: 64; Issue: 1 Linguagem: Inglês
10.1021/np000219r
ISSN1520-6025
AutoresA. A. Leslie Gunatilaka, John M. Berger, Randy Evans, James S. Miller, Jan H. Wisse, Kim M. Neddermann, Isia Bursuker, David G. I. Kingston,
Tópico(s)Morinda citrifolia extract uses
ResumoBioactivity-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 IC(50) value of 10 microg/mL. In the A2780 cell line, compounds 1, 2 and 5 had IC(50) values of 7.9, 2.9, and 3.2 microg/mL, respectively.
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