Journal
PLANTA MEDICA
Volume 82, Issue 11-12, Pages 1096-1104Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0042-108059
Keywords
Millettia caerulea; Fabaceae; rotenoids and isoflavonoids; cancer cell growth inhibition; NF-kappa B and K-Ras inhibition; quinone reductase induction
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Funding
- National Cancer Institute, NIH, Bethesda, MD
- [P01 CA125066]
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Three new rotenoids (1-3), two new isoflavonoids (4 and 5), and six known analogues (6-11) were isolated from an n-hexane partition of a methanol extract of the fruits of Millettia caerulea, with the structures of the new compounds elucidated by analysis of their spectroscopic data. The relative configurations of the rotenoids were determined by interpretation of their NMR spectroscopic data, and their absolute configurations were established using electronic circular dichroism spectra and specific rotation values. All compounds isolated were evaluated for their cell growth inhibitory activity against the HT-29 human colon cancer cell line, and the known compounds, (-)-3-hydroxyrotenone (6) and (-)-rotenone (7), were found to be potently active. When tested in an NF-kappa B inhibition assay, compound 6 showed activity. This compound, along with the new compound, (-)-caeruleanone D (1), and the known compound, ichthynone (8), exhibited K-Ras inhibitory potency. Further bioactivity studies showed that the new compounds, (-)-3-deoxycaeruleanone D (2) and (-)-3-hydroxycaeruleanone A (3), and the known compounds 8 and 11 induced quinone reductase in murine Hepa 1c1c7 cells.
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