Anti-oestrogenic diarylheptanoids from Aframomum melegueta with in silico oestrogen receptor alpha binding conformation similar to enterodiol and enterolactone

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• 作者：Ali M. El-Halawany^a ; ^b ; ^{ahalawany2003@yahoo.com} ; Masao Hattori^a
• 关键词：Aframomum melegueta ; Diarylheptanoids ; ER伪 ; Enterodiol ; Enterolactone ; Gingerenone ; SERM
• 刊名：Food Chemistry
• 出版年：2012
• 期刊代码：48_03088146
• 类别：abs
• 出版时间：1 September, 2012
• 卷：134
• 期：1
• 页码：219-226
• 文件大小：586 K

摘要

Aframomum melegueta is a spice widely used in African folk medicine. The chloroform soluble fraction of A. melegueta seeds yielded four new diarylheptanoids named gingerenone D (1), dihydrogingerenone A (2), dihydrogingerenone B (3), and dihydrogingerenone C (4), in addition to six known diarylheptanoids and hydroxyphenylalkanones. The most potent oestrogen receptor binding ability in an oestrogen receptor alpha (ER伪) competitive-binding assay was for compounds 1, 2 and 5 with IC₅₀ values of 50, 79 and 39 渭M, respectively, compared with 18 nM for the natural steroid 17尾-oestradiol (E2). In addition, the diarylheptanoids 1, 2 and 5 showed anti-oestrogenic activity in a receptor cofactor assay system for ER伪, while the hydroxyphenylalkanone, [6]dehydrogingerdione, (7) exhibited an agonistic action. Results were interpreted via virtual docking of the active compounds to an ER伪 crystal structure, in comparison with the known oestrogenic compounds: enterodiol (END), enterolactone (ENL), genistein and E2. The anti-oestrogenic compounds 1, 2 and 5 showed a binding similarity to that of END and ENL while compound 7 was similar in binding to genistein and E2 interpreting its agonistic effect.