Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor

被引:22
作者
Xie, Weijia [1 ,2 ]
Tanabe, Genzoh [1 ]
Matsuoka, Kanjyun [1 ]
Amer, Mumen F. A. [1 ]
Minematsu, Toshie [1 ]
Wu, Xiaoming [2 ]
Yoshikawa, Masayuki [3 ]
Muraoka, Osamu [1 ]
机构
[1] Kinki Univ, Sch Pharm, Osaka 5778502, Japan
[2] China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Peoples R China
[3] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan
关键词
Kotalanol; alpha-Glucosidase inhibitor; Salacia; SAR study; Selective inhibition; THIOSUGAR SULFONIUM SULFATE; MEDICINE SALACIA-RETICULATA; AYURVEDIC MEDICINE; ASYMMETRIC DIHYDROXYLATION; GLYCOSIDASE INHIBITORS; BIOLOGICAL EVALUATION; MALTASE-GLUCOAMYLASE; RECENT INSIGHTS; ANALOGS; SALAPRINOL;
D O I
10.1016/j.bmc.2011.02.028
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Synthesis and evaluation of four diastereomers (9a, 9b, 9c and 9d) of kotalanol, a potent alpha-glucosidase inhibitor isolated from an Ayurvedic medicinal plant Salacia species, are described. Stereo-inversion at C-3' and C-4' of kotalanol (2) caused significant decrease of the inhibitory activities against maltase and sucrase, whereas inhibitory activity against isomaltase sustained, thus resulted in exerting selectivity against isomaltase. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2252 / 2262
页数:11
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