Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol,a potent natural α-glucosidase inhibitor. Part 2 |
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Authors: | Genzoh Tanabe Kanjyun Matsuoka Masahiro Yoshinaga Weijia Xie Nozomi Tsutsui Mumen F A Amer Shinya Nakamura Isao Nakanishi Xiaoming Wu Masayuki Yoshikawa Osamu Muraoka |
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Institution: | 1. School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan;2. Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing, Jiang Su 210009, People’s Republic of China;3. Kyoto Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan |
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Abstract: | To examine the role of the side chain of kotalanol (2), a potent natural α-glucosidase inhibitor isolated from Salacia reticulata, on inhibitory activity, four diastereomers (11a–11d) with reversed configuration (S) at the C-4′ position in the side chain were synthesized and evaluated. Two of the four (11b and 11d) significantly lost their inhibitory activity against both maltase and sucrase, while the other two (11a and 11c) sustained the inhibitory activity to a considerable extent, showing distinct activity in response to the change of stereochemistry of the hydroxyls at the 5′and 6′ positions. Different activities were rationalized with reference to in silico docking studies on these inhibitors with hNtMGAM. Against isomaltase, all four analogs showed potent inhibitory activity as well as 2, and 11b and 11d exhibited enzyme selectivity. |
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