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Two new flavonoids from Dracaena usambarensis Engl.
Phytochemistry Letters ( IF 1.7 ) Pub Date : 2020-01-29 , DOI: 10.1016/j.phytol.2020.01.001
Vaderament-A. Nchiozem-Ngnitedem , Leonidah Kerubo Omosa , Solomon Derese , Pierre Tane , Matthias Heydenreich , Michael Spiteller , Ean-Jeong Seo , Thomas Efferth

Investigations of the root extract of Dracaena usambarensis Engl. for anticancer principles led to the characterization of one new homoisoflavonoid, (3S)-3,4ʹ,5,6-tetrahydroxy-7-methoxyhomoisoflavanone (1) and a new retrodihydrochalcone, 4ʹ,4-dihydroxy-2,3-dimethoxydihydrochalcone (2) along with six previously reported compounds, including two homoisoflavonoids, 7-O-methyl-8-demethoxy-3-hydroxy-3,9-dihydropunctatin (3) and loureiriol (4); a phenolic amide, 3-(4ʹʹʹ-hydroxyphenyl)-N-[2ʹ-(4ʹʹ-hydroxyphenyl)-2ʹ-methoxyethyl]acrylamide (5); a spirostane, 25S-spirosta-1,4-dien-3-one (6) and two steroids, stigmasterol (7) and stigmasterol 3-O-β-D-glucopyranoside (8). The structures of 1-8 were determined using spectroscopic and spectrometric techniques. The absolute configurations of compounds 1 and 3 were achieved using circular dichroism spectroscopy. Using the resazurin reduction assay and doxorubicin as reference anticancer drug, 1 showed moderate cytotoxicity against drug sensitive CCRF-CEM but was inactive against all the other tested drug sensitive, resistance phenotypes and normal cells. The crude extract and 2-8 were inactive in the preliminary screening against CCRF-CEM and drug resistant CEM/ADR5000 cell lines. Interestingly, the activity of the standard drug, doxorubicin was comparable to those of inactive compounds against CEM/ADR5000 cells. Future studies should focus on structure modifications of 1-3, in order to obtain more potent analogues.



中文翻译:

来自美国龙血树Dragona usambarensis Engl的两种新黄酮。

龙血树龙脑根提取物的研究。的抗癌原理导致表征了一种新的同型异黄酮类化合物(3 S)-3,4ʹ,5,6-四羟基-7-甲氧基高异黄酮(1)和新的逆二氢查耳酮4ʹ,4-二羟基-2,3-二甲氧基二氢查耳酮(2)以及六个先前报道的化合物,包括两个同型异黄酮类化合物,7 - O-甲基-8-去甲氧基-3-羟基-3,9-二氢punctatin (3)和卢瑞洛尔(4);酚酰胺,3-(4′-羟基苯基)-N- [2′-(4′-羟基苯基)-2′-甲氧基乙基]丙烯酰胺(5);螺环烷25 S-螺环-1,4-二-3-6)和两种类固醇,豆甾醇(7)和豆甾醇3- O- β- D-吡喃葡萄糖苷(8)。的结构1 - 8使用光谱和光谱技术进行了测定。化合物13的绝对构型是使用圆二色光谱法获得的。使用刃天青素还原测定法和阿霉素作为参考抗癌药,1显示出对药敏CCRF-CEM的中等细胞毒性,但对所有其他测试的药敏,耐药表型和正常细胞无活性。将粗提取物和2 - 8在针对CCRF-CEM和耐药性CEM / ADR5000细胞系的初步筛选中没有活性。有趣的是,标准药物阿霉素的活性与无活性化合物对CEM / ADR5000细胞的活性相当。未来的研究应集中在结构修改1 - 3中,为了获得更有效的类似物。

更新日期:2020-01-29
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