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Bioactive 5,6-Dihydro-alpha-pyrone Derivatives from Hyptis brevipes

Deng, Ye and Balunas, Marcy J. and Kim, Jeong-Ah and Lantvit, Daniel D. and Chin, Young-Won and Chai, Heebyung and Sugiarso, Sugeng and Kardono, Leonardus B. S. and Fong, Harry H. S. and Pezzuto, John M. and Swanson, Steven M. and de Blanco, Esperanza J. Carcache and Kinghorn, A. Douglas (2009) Bioactive 5,6-Dihydro-alpha-pyrone Derivatives from Hyptis brevipes. JOURNAL OF NATURAL PRODUCTS, 72 (6). 1165 -1169. ISSN 0163-3864

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Six new 5,6-dihydro-alpha-pyrone derivatives (1-6), namely, brevipolides A-F, together with seven known compounds, including a 5,6-dihydro-alpha-pyrone derivative (7), three flavonoids, a steroid glycoside, and two triterpenoids, were isolated from the entire plant of Hyptis brevipes. Compounds 1-7 were assigned with the absolute configuration 5R, 6S, 7S, and 9S, as elucidated by analysis of data obtained from their CD spectra and by Mosher ester reactions. Compounds 2, 6, and 7 exhibited ED50 values of 6.1, 6.7, and 3.6 mu M against MCF-7 cells, and compounds 1, 2, 6, and 8 (the known 5,6,3'-trihydroxy-3,7,4'-trimethoxyflavone) gave ED50 values of 5.8, 6.1, 7.5, and 3.6 mu M against HT-29 cells, respectively. However, no significant cytotoxicity was found against Lu l cells for any of the compounds isolated. When these compounds were subjected to evaluation in a panel of mechanism-based in vitro assays, compound 7 was found to be active in an enzyme-based ELISA NF-kappa B assay, with an ED50 value of 15.3 mu M. In a mitochondrial transmembrane potential assay, compounds 3, 7, and 8 showed ED50 values of 8.5, 75, and 310 nM, respectively. No potent activity was found in a proteasome inhibition assay for any of the isolated compounds.

Item Type:Article
Subjects:Material Science > Nanochemistry
Biomedical Science > Nanomedicine
ID Code:7896
Deposited By:CSMNT
Deposited On:02 Jan 2010 08:03
Last Modified:02 Jan 2010 08:03

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