(R)‐ricinoleic acid is the main component of castor oil from Ricinus communis L. Due to the presence of the hydroxyl group in homoallylic position and asymmetrically substituted carbon atom, it may undergo a number of chemical and biochemical transformations resulting in the products with some specific bioactivities. Conversion of (R)‐ricinoleic acid into its (S)‐enantiomer enables synthesis of both (R)‐ and (S)‐ricinoleic acid derivatives and comparison of their biological activities. In the present research, (R)‐ and (S)‐ricinoleic acid amides synthesized from methyl ricinoleates and ethanolamine or pyrrolidine as well as acetate derivatives of ethanolamine amides were studied to demonstrate their biological activities using HT29 cancer cells. Double staining of cells with fluorochromes (Hoechst 33258/propidium iodide) as well as 2,′7′‐dichlorodihydrofluorescein (DCF) and comet assays were performed. Both the tested amides and acetates caused DNA damage and induced apoptotic and necrotic cell death. In the case of (R)‐ and (S)‐enantiomers of one of the tested acetates, significant difference in the ability to induce DNA damage was observed, which showed the impact of the stereogenic center on the activities of these compounds.

中文翻译：

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（R）-和（S）-蓖麻油酸衍生物的细胞毒性和遗传毒性作用。

（- [R）-ricinoleic酸是蓖麻油的从主组件蓖麻L.由于高烯丙基位的羟基和不对称取代的碳原子的存在，它可经历许多化学和生物化学转化的导致产品具有一些特定的生物活性。将（R）-蓖麻油酸转化为其（S）-对映异构体可合成（R）-和（S）-蓖麻油酸衍生物并比较其生物学活性。在本研究中，（R）‐和（S）研究了由蓖麻油酸甲酯和乙醇胺或吡咯烷合成的蓖麻油酸酰胺以及乙醇胺酰胺的乙酸酯衍生物，以证明其在HT29癌细胞中的生物学活性。用荧光染料（Hoechst 33258 /碘化丙啶）以及2，'7'-二氯二氢荧光素（DCF）对细胞进行了两次染色，并进行了彗星试验。测试的酰胺和乙酸盐均引起DNA损伤，并诱导凋亡和坏死细胞死亡。在一种被测乙酸盐的（R）-和（S）-对映异构体的情况下，观察到诱导DNA损伤的能力存在显着差异，这表明立体生成中心对这些化合物活性的影响。