P-50 α-グルコシダーゼ阻害剤,kotalanolの合成研究(ポスター発表の部)

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Kotalanol (1) is a new class of potent glycosidase inhibitor, isolated together with salacinol (2) from Ayruvedic medicine Salacia reticulata, having the unique zwitterionic structure comprising of 1-deoxy-4-thio-D-arabinofranosyl cation and the sulfate anion in the heptitol side chain. Although 1 is known to possess even stronger inhibitory activity against certain glucosidase enzymes than 2, no synthetic trial of 1 has been reported because of the unidentified absolute stereochemistry of 5 kinds of carbinol carbons in the heptitol unit. During the course of our synthetic study on 1, four diastereomers 1a, 1b, 1c and 1b, which maintained 2'S and 3'S configuration of salacinol (2) in addition to 4'S configuration as common side chain feature, have been synthesized by the use of the coupling reaction of protected cyclic sulfates (5a, 5b, 5c and 5b) derived from D-ribose derivative (9) with thiosugar (4). The inhibitory activities of the synthesized analogs were also evaluated against rat intestinal glucosidases. All analogs showed less inhibitory activity against sucrase and maltase compared to 1 although they possessed the same stereochemistry at C-2' and C-3' as 2, and the results indicated that the C-4' configuration was critical for the inhibitory activity. Interestingly, potent isomaltase inhibitory activity equal to those of 1 and 2 was found for both C-6 epimers 1a and 1d, indicating that the stereochemistry of the hydroxyl at C-6' was not essential for the isomaltase inhibitory activity.
天然有機化合物討論会の論文
2007-08-24

P-50 α-グルコシダーゼ阻害剤,kotalanolの合成研究(ポスター発表の部)

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