Cytotoxic Homoisoflavones from the Bulbs of Bellevalia eigii

详细信息    查看全文

• 作者：Feras Alali ; Tamam El-Elimat ; Hanan Albataineh ; Qosay Al-Balas ; Mohammad Al-Gharaibeh ; Joseph O. Falkinham ; III ; Wei-Lun Chen ; Steven M. Swanson ; Nicholas H. Oberlies
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：July 24, 2015
• 年：2015
• 卷：78
• 期：7
• 页码：1708-1715
• 全文大小：376K
• ISSN：1520-6025

文摘

Eight new and 10 known compounds were isolated from an organic extract of the bulbs of Bellevalia eigii as part of a search for anticancer leads from native plants of Jordan. Of these, the series of 16 homoisoflavonoids (1鈥?b>16) comprise the seven new analogues 7-O-methyl-3鈥?hydroxy-3,9-dihydropunctatin (3), 6-hydroxy-7-O-methyl-3,9-dihydropunctatin (6), 7,4鈥?di-O-methyl-3鈥?hydroxy-3,9-dihydropunctatin (9), 7-O-methylpunctatin (10), 7-O-methyl-3鈥?hydroxypunctatin (13), 5-hydroxy-7,8-dimethoxychroman-4-one (14), and 7-O-methyl-8-demethoxy-3-hydroxy-3,9-dihydropunctatin (15). The known ferulic acid-derived acrylamide (17) and the new methylthioacrylate bellegimycin (18) are also reported. The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configurations of compounds 1鈥?b>9, 15, and 16 were determined using ECD spectroscopy, while a modified Mosher鈥檚 ester method was used for compound 18. Optical rotation data for the known compounds 1, 2, and 8 are reported here for the first time. The cytotoxic activities of all compounds were evaluated using the MDA-MB-435 (melanoma) and HT-29 (colon) cancer cell lines. Compounds 4 and 9 were the most potent on the latter cell line, with IC₅₀ values of 1.0 and 1.1 渭M, respectively. Compounds 1鈥?b>18 were assessed for antimicrobial activity using a collection of bacteria and fungi; compounds 4 and 12 showed promising activity against the bacterium Mycobacterium smegmatis with MIC values of 17 and 24 渭g/mL, respectively.