Semisynthesis and cytotoxicity of E-naringenin oximes from naringin

Abstract

Naringenin (N-1) 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-1b-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. © 2013 Chinese Chemical Society & SIOC, CAS.