柚皮苷半合成E-柚皮素肟类化合物及细胞活性

Semisynthesis and Cytotoxicity of E-Naringenin Oximes from Naringin

从丰富价廉的天然柚皮苷(Naringin)出发,经水解、选择性甲基化、异戊烯基化分别得到了柚皮素N-1及柚皮素衍生物N-2~N-6.N-1~N-6分别与盐酸羟胺、盐酸甲氧胺、盐酸苄氧胺反应合成了6个E-柚皮素肟N-1a^N-6a和10个E-柚皮素肟醚化合物N-1b^N-6c.所合成产物通过NMR,HR-ESI-MS方法进行了结构确证;MTT法体外抑制肿瘤增值活性测试显示N-1a,N-1b,N-1c,N-2a,N-4a对胃癌细胞SGC-7901有一定的抑制活性.

Naringenin （N-l） and naringenin derivatives N-2～N-6 were synthesized by the hydrolysis, selective methylation or selective O-prenylation using natural naringin as starting material. Six E-naringenin oximes N-1a～N-6a and ten E-naringenin oxime ethers N-lb^N-6c were synthesiszed by reacting N-1～N-6 with hydroxylamine hydrochloride, methoxylamine hydrochloride and benzyloxygen amine hydrochloride, respectively. The structures of the compounds were identified by NMR and HR-ESI-MS. The cytotoxicities of the compounds were evaluated by MTT assay and the results showed that N-1a, N-1b, N-1c, N-2a, N-4a displayed moderate activity against human cancer cell line SGC-7901.