Structure-activity Relationships for α-Glucosidase Inhibition of Baicalein, 5,6,7-Trihydroxyflavone : the Effect of A-Ring Substitution

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概要

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• In order to estimate the effects of the A-ring hydroxyl group of baicalein (5,6,7-trihydroxyflavone, 1) on rat intestinal α-glucosidase inhibition, flavone, monohydroxyflavones, dihydroxyflavones, and methylated derivatives of 5,6,7-trihydroxyflavone were used for the structure-activity relationship (SAR) study. The importance of the 6-hydroxyl group of baicalein was validated for an exertion of the activity. And also, the tested flavones which lacked a hydroxyl substituent on any of positions 5, 6, or 7, showed no activity. Hence, the 5,6,7-trihydroxyflavone structure was concluded to be crucial for the potent inhibitory activity. In addition, an introduction of electron-withdrawing or electron-donating groups at position 8 of baicalein led to a dramatic decrease for activity, except for 8-fluoro-5,6,7-trihydroxyflavone, which carried a less bulky substituent on position 8. Hence, this result suggested that a sterically bulky substituent on C-8 of baicalein was detrimental for the activity regardless of its electronic nature. Through examining the inhibitory mechanism of baicalein against rat intestinal α-glucosidase, it was suggested to be a mixed type inhibition.

• 社団法人 日本農芸化学会の論文
• 2004-02-23

著者

• Kawabata J

  Hokkaido Univ. Sapporo Jpn

• Kawabata Jun

  Lab. Of Food Biochemistry Div. Of Applied Bioscience Graduate School Of Agriculture Hokkaido Univ.

• Kawabata Jun

  Graduate School Of Agriculture Hokkaido University

• Kawabata Jun

  Laboratory Of Food Biochemistry Division Of Applied Bioscience Graduate School Of Agriculture Hokkai

• KASAI Takanori

  Laboratory of Food Biochemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hok

• GAO Hong

  Laboratory of Food Biochemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hok

• NISHIOKA Tetsuo

  Laboratory of Food Biochemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hok

• Kawabata Jun

  Bioscience And Chemistry Faculty Of Agriculture Hokkaido University

• Kasai T

  Laboratory Of Food Biochemistry Division Of Applied Bioscience Graduate School Of Agriculture Hokkai

• Kasai Takanori

  Laboratory Of Food Biochemistry Department Of Bioscience And Chemistry Faculty Of Agriculture Hokkai

• Nishioka T

  Laboratory Of Food Biochemistry Division Of Applied Bioscience Graduate School Of Agriculture Hokkai

• Kawabata Jun

  Laboratory Of Food Biochemistry Division Of Applied Bioscience Graduate School Of Agriculture Hokkai

• Gao Hong

  Laboratory Of Food Biochemistry Division Of Applied Bioscience Graduate School Of Agriculture Hokkai

• Gao Hong

  Laboratory Of Food Biochemistry Division Of Applied Bioscience Graduate School Of Agriculture Hokkai

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