Synthetically derived samples of (+)-(6aS,11aS)-2,3,9-trimethoxypterocarpan [(+)-1] and its enantiomer [(−)-1], both of which are examples of naturally occurring isoflavonoids, were evaluated, together with the corresponding racemate, as cytotoxic agents against the HL-60, HCT-116, OVCAR-8, and SF-295 tumor cell lines. As a result it was established that compound (+)-1 was particularly active with OVCAR-8 cells being the most sensitive and responding in a dose-dependent manner. A study of cell viability and drug-induced morphological changes revealed the compound causes cell death through a mechanism characteristic of apoptosis. Finally, a computational study of the interactions of compound (+)-1 and (S)-monastrol, an established, synthetically derived, potent, and cell-permeant inhibitor of mitosis, with the kinesin-type protein Eg5 revealed that both bind to this receptor in a similar manner. Significantly, compound (+)-1 binds with greater affinity, an effect attributed to the presence of the associated methoxy groups.

中文翻译：

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异黄酮类化合物（+）-和（-）-2,3,9-三甲氧基翼果聚糖的抗肿瘤潜力：作用机理研究。

（+）-（6a S，11a S）-2,3,9-三甲氧基翼果烷[（+）- 1 ]及其对映异构体[（-）- 1 ]的合成衍生样品，它们都是天然存在的异黄酮的实例作为抗HL-60，HCT-116，OVCAR-8和SF-295肿瘤细胞系的细胞毒剂，将其与相应的外消旋物一起评估。结果证实了化合物（+）- 1对OVCAR-8细胞是最敏感的并且以剂量依赖性方式响应的特别活性。对细胞活力和药物诱导的形态变化的研究表明，该化合物通过凋亡的机制特征导致细胞死亡。最后，对化合物（+）-的相互作用进行了计算研究1和（S）-monastrol是一种成熟的，合成的，有力的和细胞渗透性的有丝分裂抑制剂，具有驱动蛋白类型的蛋白Eg5，表明两者都以相似的方式与该受体结合。明显地，化合物（+1）-1以更大的亲和力结合，这归因于相关甲氧基的存在。