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

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• 作者：Ye Deng ; Marcy J. Balunas ; Jeong-Ah Kim ; Daniel D. Lantvit ; Young-Won Chin ; Heebyung Chai ; Sugeng Sugiarso ; Leonardus B. S. Kardono ; Harry H. S. Fong ; John M. Pezzuto ; Steven M. Swanson ; Esperanza J.
• 刊名：Journal of Natural Products
• 出版年：2009
• 出版时间：June 26, 2009
• 年：2009
• 卷：72
• 期：6
• 页码：1165-1169
• 全文大小：117K
• 年卷期：v.72,no.6(June 26, 2009)
• ISSN：1520-6025

文摘

Six new 5,6-dihydro-α-pyrone derivatives (1−6), namely, brevipolides A−F, together with seven known compounds, including a 5,6-dihydro-α-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 μM 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 μM against HT-29 cells, respectively. However, no significant cytotoxicity was found against Lu1 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-κB assay, with an ED₅₀ value of 15.3 μM. 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.