Cytotoxic Homoisoflavones from the Bulbs of Bellevalia eigii

被引:33
作者
Alali, Feras [1 ]
El-Elimat, Tamam [2 ]
Albataineh, Hanan [2 ]
Al-Balas, Qosay [2 ]
Al-Gharaibeh, Mohammad [3 ,4 ]
Falkinham, Joseph O., III [5 ]
Chen, Wei-Lun [6 ]
Swanson, Steven M. [6 ]
Oberlies, Nicholas H. [7 ]
机构
[1] Qatar Univ, Fac Pharm, Doha 2713, Qatar
[2] Jordan Univ Sci & Technol, Fac Pharm, Dept Med Chem & Pharmacognosy, Irbid 22110, Jordan
[3] Jordan Univ Sci & Technol, Fac Agr, Dept Nat Resources & Environm, Irbid 22110, Jordan
[4] Univ Halle Wittenberg, Inst Geobot & Bot Garten, D-06108 Halle, Germany
[5] Virginia Polytech Inst & State Univ, Dept Biol Sci, Blacksburg, VA 24061 USA
[6] Univ Illinois, Coll Pharm, Dept Med Chem & Pharmacognosy, Chicago, IL 60612 USA
[7] Univ N Carolina, Dept Chem & Geochem, Greensboro, NC 27402 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 07期
基金
美国国家卫生研究院;
关键词
ABSOLUTE-CONFIGURATION; MUSCARI-COMOSUM; 3-BENZYL-4-CHROMANONES; COLCHICINOIDS; HYACINTHACEAE;
D O I
10.1021/acs.jnatprod.5b00357
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
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 (1-16) comprise the seven new analogues 7-O-methyl-3'-hydroxy-3,9-dihydropunctatin (3), 6-hydroxy-7-O-methyl-3,9-dihydropunctatin (6), 7,4'-di-O-methyl-3'-hydroxy-3,9-dihydropunctatin (9), 7-O-rnethylpunctatin (10), 7-O-methyl-3'-hydroxypunctatin (13), 5-hydroxy-7,8-dimethoxychroman-4-one (14), and 7-O-methy1-8-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 1-9, 15, and 16 were determined using ECD spectroscbpy, while a modified Mosher's 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 mu M, respectively. Compounds 1-18 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 mu g/mL, respectively.
引用
收藏
页码:1708 / 1715
页数:8
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