PMID: 15388960Sep 25, 2004Paper

Importance of the B ring and its substitution on the alpha-glucosidase inhibitory activity of baicalein, 5,6,7-trihydroxyflavone

Bioscience, Biotechnology, and Biochemistry
Hong Gao, J Kawabata

Abstract

Hydroxychromones and B-ring-substituted 5,6,7-trihydroxyflavones were prepared to evaluate the contribution of the B ring of baicalein (5,6,7-trihydroxyflavone, 1) to its potent alpha-glucosidase inhibitory activity. Hydroxychromones, which lack 6-hydroxyl substitution, did not show any inhibitory activity, while 5,6,7-trihydroxy-2-methylchromone (5) showed high activity. Among the tested B-ring-substituted 5,6,7-trihydroxyflavones, the 4'-hydroxy-, 3',4'-dihydroxy-, and 3',4',5'-trihydroxy-substituted derivatives were found to give more activity than that of 1. The methoxy-substituted derivatives, however, showed less activity than 1. The results suggest that the B ring of 1 was not essential, although advantageous to the activity; hydroxyl substitution on the B ring of 5,6,7-trihydroxyflavones was favorable to the activity, whereas methoxyl substitution was unfavorable; at least 4'-hydroxyl substitution of 5,6,7-trihydroxyflavones was required for enhanced activity, in which the number of hydroxyl groups did not take part.

References

Dec 3, 1998·Journal of Natural Products·T NishiokaY Aoyama
Mar 23, 2002·Bioorganic & Medicinal Chemistry Letters·Tomomi NoguchiYuichi Hashimoto
May 6, 2003·Bioscience, Biotechnology, and Biochemistry·Jun KawabataTakanori Kasai

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Citations

May 5, 2011·International Journal of Molecular Sciences·Sung-Hoon JoYoung-In Kwon
Oct 20, 2011·Natural Product Research·Giuliana RighiPaolo Bovicelli
Jun 29, 2006·Journal of Nutritional Science and Vitaminology·Kenjiro TaderaTomoko Matsuoka
Jun 19, 2013·Critical Reviews in Food Science and Nutrition·Jianbo XiaoXiaoqing Chen
Sep 20, 2015·European Journal of Pharmacology·Toshiro Matsui
Feb 25, 2015·Pharmacognosy Magazine·Ratree PranakhonPatchareewan Pannangpetch
Aug 19, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hong GaoJun Kawabata
Nov 11, 2017·Chemistry & Biodiversity·Ana P de OliveiraSilvia H Taleb-Contini
Sep 22, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Carina ProençaEduarda Fernandes
Aug 26, 2014·Chemistry & Biodiversity·Yusuke WatanabeFrancisco A Macías
Jul 25, 2006·American Journal of Physiology. Lung Cellular and Molecular Physiology·Minqing ZhaoVictor E Laubach
Nov 28, 2012·Molecular Nutrition & Food Research·Gary Williamson
Aug 28, 2021·Foods·Elizabeth BarberGary Williamson
May 24, 2008·Journal of Agricultural and Food Chemistry·Kaori YoshidaJun Kawabata

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