Alali Feras, El-Elimat Tamam, Albataineh Hanan, Al-Balas Qosay, Al-Gharaibeh Mohammad, Falkinham Joseph O, Chen Wei-Lun, Swanson Steven M, Oberlies Nicholas H
†Faculty of Pharmacy, Qatar University, Doha 2713, Qatar.
⊥Institut für Geobotanik und Botanischer Garten, Martin-Luther-Universität, Am Kirchtor 1, 06108 Halle, Germany.
J Nat Prod. 2015 Jul 24;78(7):1708-15. doi: 10.1021/acs.jnatprod.5b00357. Epub 2015 Jul 6.
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-methylpunctatin (10), 7-O-methyl-3'-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 1-9, 15, and 16 were determined using ECD spectroscopy, 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 μM, 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 μg/mL, respectively.
作为从约旦本土植物中寻找抗癌先导物的一部分，从埃及绵枣儿鳞茎的有机提取物中分离出了8种新化合物和10种已知化合物。其中，16种高异黄酮类化合物（1-16）包括7种新类似物，即7-O-甲基-3'-羟基-3,9-二氢斑点菌素（3）、6-羟基-7-O-甲基-3,9-二氢斑点菌素（6）、7,4'-二-O-甲基-3'-羟基-3,9-二氢斑点菌素（9）、7-O-甲基斑点菌素（10）、7-O-甲基-3'-羟基斑点菌素（13）、5-羟基-7,8-二甲氧基色满-4-酮（14）和7-O-甲基-8-去甲氧基-3-羟基-3,9-二氢斑点菌素（15）。还报道了已知的阿魏酸衍生的丙烯酰胺（17）和新的甲硫基丙烯酸酯类化合物埃及绵枣儿霉素（18）。使用一系列光谱和光谱技术阐明了这些化合物的结构；化合物1-9、15和16的绝对构型通过电子圆二色光谱法确定，而化合物18则使用改良的莫舍尔酯法。首次报道了已知化合物1、2和8的旋光数据。使用MDA-MB-435（黑色素瘤）和HT-29（结肠）癌细胞系评估了所有化合物的细胞毒性活性。化合物4和9对后一种细胞系的活性最强，IC50值分别为1.0和1.1μM。使用一组细菌和真菌评估了化合物1-18的抗菌活性；化合物4和12对耻垢分枝杆菌显示出有前景的活性，MIC值分别为17和24μg/mL。
