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Effect of glycoside bond on insulin mimetic activity of flavonoid-neohesperidose conjugate

Effect of glycoside bond on insulin mimetic activity of flavonoid-neohesperidose conjugate 〇 Ryogo Hishiki , Eisuke Kato, Jun Kawabata Laboratory of Food Biochemistry, Research Faculty of Agriculture, Hokkaido University. Experiment 1. Introduction.

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Effect of glycoside bond on insulin mimetic activity of flavonoid-neohesperidose conjugate

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  1. Effect of glycoside bond on insulin mimetic activity of flavonoid-neohesperidose conjugate • 〇RyogoHishiki, Eisuke Kato, Jun Kawabata • Laboratory of Food Biochemistry, Research Faculty of Agriculture, Hokkaido University Experiment 1 Introduction Kaempferol 3-O-neohesperidoside (1), which is one of flavonoid glycosides, was reported to induce glucose uptake in skeletal muscle cells. This compound is expected to become a new drug for Diabetes mellitus because it shows insulin mimetic activity in nanomolar scale and probably has a mechanism which is different from traditional model. We recently reported that neohesperidose, which is the glycoside part of 1, is the key structurefor the activity. However, further study indicated that naringindid not show the activity in spite of containing neohesperidose in its strucure. Insulin Mimetic Activity of 2 & 3 Conclusion & Discussion Flavonoid glycoside 2 and 3 did not show any insulin mimetic activity. This result further supported hypothesis Ⅰ, but there was still another possibility that altered steric hindrance was the reason of altered activity. Then we focused on S-glycosyl bond which is more stable than O-glycosyl one and we are currently synthesizing apigeninS-neohesperidoside(4) to investigate the effect of steric hindrance. Objective Based on the above result, we made two hypotheses about the mechanism. Hypothesis Ⅰ is that the activity of 1 is induced from the released neohesperidose, because the position of the glycoside bond of 1 has the highest reactivity (blue arrow in the figure below). And hypothesis Ⅱ is that the difference of the steric structures affects the activity (red arrow). To investigate these possibilities, we planned two experiments. (Experiment1 & 2). Synthesis of 2 & 3 Exp.1 Seeing the activity of the flavonoid glycosides 2 and 3whose glycosylation positions are different from 1 Seeing the effect of steric hindrance by the activity of flavonoidthioglycoside4 Exp.2 Assay Procedure Experiment 2 Synthesis of 4

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