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Homoisoflavonoids from the bulbs of Bellevalia longipes and an assessment of their potential cytotoxic activity
Phytochemistry ( IF 3.8 ) Pub Date : 2022-08-11 , DOI: 10.1016/j.phytochem.2022.113343
Tamam El-Elimat 1 , Reema Al-Qiam 1 , Joanna E Burdette 2 , Ahmed H Al Sharie 3 , Mohammad Al-Gharaibeh 4 , Nicholas H Oberlies 5
Affiliation  

Seven undescribed homoisoflavonoids were identified from the bulbs of Bellevalia longipes Post (Asparagaceae) as well as thirteen known and one natural homoisoflavonoid that had been reported as a synthetic product previously. A general approach for recognizing homoisoflavonoids via NMR spectroscopy data were presented. The undescribed compounds were: 8-dehydroxy-5-O-demethyl-6-hydroxyscillapersicone, 6-methoxyscillapersicone, 5-O-demethyl-6-methoxyscillapersicone, 8-O-methylscillapersicone, 4′-O-methylscillapersicone, 4′,8-O,O-dimethylscillapersicone, 3′-O-methylscillapersicone, and 3-hydroxy-desmethylophiopogonanone A. Structures were determined based on analysis of HRMS and NMR data, while absolute configurations were assigned using ECD spectroscopy. Human cancer cell lines were used to assess the cytotoxic activities of the isolated compounds, where 3-dehydroxy-3′-hydroxyeucomol showed IC50 values of 0.62 μM, 5.36 μM, and 2.52 μM, when tested against MDA-MB-435 (melanoma), MDA-MB-231 (breast), and OVCAR3 (ovarian) cells, respectively.



中文翻译:

来自 Bellevalia longipes 球茎的同种异黄酮及其潜在细胞毒活性的评估

从 Bellevalia longipes Post(天门冬科)的球茎中鉴定出七种未描述的同型异黄酮,以及十三种已知的同型异黄酮和一种天然的同型异黄酮,这些同型异黄酮之前被报道为合成产品。介绍了通过 NMR 光谱数据识别同型异黄酮的一般方法。未描述的化合物是:8-dehydroxy-5- O -demethyl-6-hydroxyscillapersicone、6-methoxyscillapersicone、5 - O -demethyl-6-methoxyscillapersicone、8- O - methylscillapersicone 、4'- O - methylscillapersicone、4',8 - O,O -二甲基scillapersicone, 3'- O-methylscillapersicone 和 3-hydroxy-desmethylophiopogonanone A. 结构是根据 HRMS 和 NMR 数据的分析确定的,而绝对配置是使用 ECD 光谱分配的。人类癌细胞系用于评估分离化合物的细胞毒活性,其中 3-dehydroxy-3'-hydroxyeucomol 在针对 MDA-MB-435(黑色素瘤)进行测试时显示 IC 50值为 0.62 μM、5.36 μM 和 2.52 μM )、MDA-MB-231(乳腺)和 OVCAR3(卵巢)细胞。

更新日期:2022-08-13
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