Structure-activity relationships for inhibition of human 5alpha-reductases by polyphenols

Biochemical Pharmacology
R A HiipakkaS Liao

Abstract

The enzyme steroid 5 alpha-reductase (EC 1.3.99.5) catalyzes the NADPH-dependent reduction of the double bond of a variety of 3-oxo-Delta(4) steroids including the conversion of testosterone to 5 alpha-dihydrotestosterone. In humans, 5 alpha-reductase activity is critical for certain aspects of male sexual differentiation, and may be involved in the development of benign prostatic hyperplasia, alopecia, hirsutism, and prostate cancer. Certain natural products contain components that are inhibitors of 5 alpha-reductase, such as the green tea catechin (-)-epigallocatechin gallate (EGCG). EGCG shows potent inhibition in cell-free but not in whole-cell assays of 5 alpha-reductase. Replacement of the gallate ester in EGCG with long-chain fatty acids produced potent 5 alpha-reductase inhibitors that were active in both cell-free and whole-cell assay systems. Other flavonoids that were potent inhibitors of the type 1 5alpha-reductase include myricetin, quercitin, baicalein, and fisetin. Biochanin A, daidzein, genistein, and kaempferol were much better inhibitors of the type 2 than the type 1 isozyme. Several other natural and synthetic polyphenolic compounds were more effective inhibitors of the type 1 than the type 2 isozyme, includi...Continue Reading

References

Oct 1, 1977·The Journal of Endocrinology·F KuttennP Mauvais-Jarvis
Mar 1, 1992·The Journal of Clinical Endocrinology and Metabolism·R Horton
Nov 29, 1972·Journal of the American Chemical Society·J J PlattnerH Rapoport
Apr 1, 1973·The Journal of Endocrinology·K D Bingham, D A Shaw
May 1, 1974·The Journal of Clinical Endocrinology and Metabolism·H U Schweikert, J D Wilson
Sep 25, 1995·Biochemical and Biophysical Research Communications·S Liao, R A Hiipakka
Aug 1, 1993·The Journal of Clinical Investigation·A E ThigpenD W Russell
Sep 15, 1993·Proceedings of the National Academy of Sciences of the United States of America·W S PearD Baltimore
Jan 1, 1994·Annual Review of Biochemistry·D W Russell, J D Wilson
Oct 1, 1993·Endocrine Reviews·J D WilsonD W Russell
Feb 1, 1996·Journal of Natural Products·E Haslam
Jun 1, 1997·Molecular Endocrinology·M S MahendrooD W Russell
Mar 26, 1998·Biological & Pharmaceutical Bulletin·Y H MiuraS Fukui
Aug 26, 1998·Annual Review of Nutrition·S K Clinton, E Giovannucci
Oct 20, 1998·Journal of the American Academy of Dermatology·K D KaufmanG J Gormley
Mar 10, 1999·Journal of the National Cancer Institute·L N KolonelR V Cooney
Mar 31, 1999·Proceedings of the National Academy of Sciences of the United States of America·D W Felsher, J M Bishop
Oct 16, 1999·Reviews of Reproduction·M S Mahendroo, D W Russell
Mar 22, 2000·Chemical Research in Toxicology·J L BoltonT J Monks
Jul 18, 2000·Pharmacogenetics·N M MakridakisJ K Reichardt
May 11, 2001·Vitamins and Hormones·S LiaoR A Hiipakka
May 30, 2001·The Journal of Steroid Biochemistry and Molecular Biology·F O BaxterI R Lee
May 30, 2001·The Journal of Steroid Biochemistry and Molecular Biology·A K Bhattacharyya, D C Collins

❮ Previous
Next ❯

Citations

Mar 31, 2009·Asian Journal of Andrology·Marina S FigueiroaMaria I Wanderley
Feb 24, 2009·Journal of Smooth Muscle Research = Nihon Heikatsukin Gakkai Kikanshi·Witness D H Chiwororo, John A O Ojewole
Jan 6, 2005·Journal of Zhejiang University. Science. B·Hai-ning YuYao-kang Xiong
Jul 5, 2003·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Thomas StrohekerMarie Christine Chagnon
May 9, 2007·Journal of Nutritional Science and Vitaminology·Toru IzumiAsahi Matsuyama
Nov 8, 2007·Critical Reviews in Food Science and Nutrition·Hai-Ning YuJun-Jie Yin
Jun 25, 2008·The British Journal of Nutrition·Claudia SteinerClaudine Manach
Aug 29, 2007·Acta Pharmacologica Sinica·Imtiaz A SiddiquiHasan Mukhtar
May 18, 2013·Daru : Journal of Faculty of Pharmacy, Tehran University of Medical Sciences·Samineh JafariMahnaz Khanavi
Nov 6, 2012·Antioxidants & Redox Signaling·Naghma KhanHasan Mukhtar
May 31, 2014·Expert Opinion on Therapeutic Targets·Ruchy Jain, Wanchai De-Eknamkul
May 27, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ruchy JainWanchai De-Eknamkul
Jan 26, 2010·Expert Opinion on Drug Delivery·Yunjin Jung, Young Mi Kim
Mar 5, 2016·Natural Product Research·Eleonora BassinoLuca Munaron
Jan 26, 2007·Clinical and Experimental Pharmacology & Physiology·Manchao ZhangQ Quentin Li
Apr 1, 2006·Journal of Neurochemistry·Paul T MassaSteven W Barger
Apr 9, 2008·Cancer Letters·Deeba N SyedHasan Mukhtar
Dec 26, 2012·Journal of Acupuncture and Meridian Studies·Mijeong BaeYong-ung Kim
Nov 1, 2005·Expert Opinion on Investigational Drugs·Kalliopi DodouPaul W Groundwater
Feb 25, 2015·Evidence-based Complementary and Alternative Medicine : ECAM·Junichi KosekiYoshio Kase
Feb 24, 2006·Bioscience, Biotechnology, and Biochemistry·Jun-Seong ParkIh Seop Chang
Nov 3, 2009·Advances in Food and Nutrition Research·Xi WangYueming Jiang
Nov 10, 2006·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·O S KwonK H Kim
Feb 11, 2004·Nutrition and Cancer·Mohammad SaleemHasan Mukhtar
Nov 22, 2011·Nutrition and Cancer·Shahnjayla K ConnorsNagi B Kumar
Apr 15, 2004·Archives of Biochemistry and Biophysics·Xiaoda NiuDaniel Lundell
Jan 25, 2006·Critical Reviews in Food Science and Nutrition·Sailendra N NichenametlaJerry H Exon
Apr 15, 2006·Expert Review of Anticancer Therapy·Andy H LeeColin W Binns
Dec 5, 2009·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·J J JohnsonH Mukhtar
Mar 8, 2013·International Journal of Molecular Sciences·Hui-Ping LinChih-Pin Chuu
Jul 11, 2012·Journal of the Science of Food and Agriculture·Dae-won Chung, Seul Bi Lee
May 14, 2011·Journal of the Science of Food and Agriculture·Hyang-Bok LeeDae-won Chung
Dec 6, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Leping YeRen-Shan Ge

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