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题名: First total synthesis of (+)-broussonetine W: glycosidase inhibition of natural product & analogs
作者: Song, Ying-Ying1, 2; Kinami, Kyoko3; Kato, Atsushi3; Jia, Yue-Mei1; Li, Yi-Xian1; Fleet, George W. J.4, 5; Yu, Chu-Yi1, 5
刊名: ORGANIC & BIOMOLECULAR CHEMISTRY
发表日期: 2016-06-14
卷: 14, 期:22, 页:5157-5174
收录类别: SCI
英文摘要: The first total synthesis of (+)-broussonetine W (4), a naturally-occurring pyrrolidine iminosugar isolated from the traditional Chinese medical plant Broussonetia kazinoki SIEB (Moraceae), has been completed through a concise synthetic route starting from the readily available D-arabinose derived cyclic nitrone 10 in 11 steps and 31% overall yield, with regioselective installation of the alpha,beta-unsaturated ketone functional group by the elimination of HBr from alpha-bromoketone as the key step. A number of analogs of (+)-broussonetine W (4) with variable side chain length, different polyhydroxylated pyrrolidine core configurations or saturated cyclohexanones have also been prepared to explore the glycosidase inhibition and the preliminary structure activity relationship of this intriguing class of compounds. Glycosidase inhibition studies identified the natural product (+)-broussonetine W (4) as a selective and potent inhibitor of p-galactosidase (IC50 = 0.03 mu M), while its enantiomer was a selective and potent inhibitor of a-glucosidase (IC50 = 0.047 mu M). It was found that the configuration of the polyhydroxylated pyrrolidine ring played a key role on their glycosidase inhibitory activities. The length of side chain and alpha,beta-unsaturated ketone functional group also exhibited some effect on their glycosidase inhibition.
语种: 英语
内容类型: 期刊论文
URI标识: http://ir.iccas.ac.cn/handle/121111/35583
Appears in Collections:分子识别与功能实验室_期刊论文

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作者单位: 1.Chinese Acad Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, BNLMS, Beying 100190, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Toyama Univ, Dept Hosp Pharm, 2630 Sugitani, Toyama 9300194, Japan
4.Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England
5.Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Peoples R China
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