Skip to main content
Advertisement

Main menu

  • Home
  • Articles
    • Current Issue
    • Fast Forward
    • Latest Articles
    • Archive
  • Information
    • Instructions to Authors
    • Submit a Manuscript
    • FAQs
    • For Subscribers
    • Terms & Conditions of Use
    • Permissions
  • Editorial Board
  • Alerts
    • Alerts
    • RSS Feeds
  • Virtual Issues
  • Feedback
  • Other Publications
    • Drug Metabolism and Disposition
    • Journal of Pharmacology and Experimental Therapeutics
    • Molecular Pharmacology
    • Pharmacological Reviews
    • Pharmacology Research & Perspectives
    • ASPET

User menu

  • My alerts
  • Log in
  • My Cart

Search

  • Advanced search
Drug Metabolism & Disposition
  • Other Publications
    • Drug Metabolism and Disposition
    • Journal of Pharmacology and Experimental Therapeutics
    • Molecular Pharmacology
    • Pharmacological Reviews
    • Pharmacology Research & Perspectives
    • ASPET
  • My alerts
  • Log in
  • My Cart
Drug Metabolism & Disposition

Advanced Search

  • Home
  • Articles
    • Current Issue
    • Fast Forward
    • Latest Articles
    • Archive
  • Information
    • Instructions to Authors
    • Submit a Manuscript
    • FAQs
    • For Subscribers
    • Terms & Conditions of Use
    • Permissions
  • Editorial Board
  • Alerts
    • Alerts
    • RSS Feeds
  • Virtual Issues
  • Feedback
  • Visit dmd on Facebook
  • Follow dmd on Twitter
  • Follow ASPET on LinkedIn
Research ArticleArticle

Glucuronides of Tea Catechins: Enzymology of Biosynthesis and Biological Activities

Hong Lu, Xiaofeng Meng, Chuan Li, Shengmin Sang, Christopher Patten, Shuqun Sheng, Jungil Hong, Naisheng Bai, Bozena Winnik, Chi-Tang Ho and Chung S. Yang
Drug Metabolism and Disposition April 2003, 31 (4) 452-461; DOI: https://doi.org/10.1124/dmd.31.4.452
Hong Lu
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Xiaofeng Meng
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Chuan Li
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Shengmin Sang
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Christopher Patten
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Shuqun Sheng
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Jungil Hong
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Naisheng Bai
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Bozena Winnik
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Chi-Tang Ho
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Chung S. Yang
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
  • Article
  • Figures & Data
  • Info & Metrics
  • eLetters
  • PDF
Loading

Abstract

(−)-Epigallocatechin gallate (EGCG) and (−)-epigallocatechin (EGC) are major green tea catechins with antioxidant and anticancer activities. In this study, we characterized the glucuronidation of EGCG and EGC in human, mouse, and rat microsomes and by nine different human UGT 1A and 2B isozymes expressed in insect cells. Six EGCG and EGC glucuronides were biosynthesized, and their structures were identified for the first time. (−)-EGCG-4"-O-glucuronide was the major EGCG glucuronide formed in all incubations. The catalytic efficiency (Vmax/Km) for (−)-EGCG-4"-O-glucuronide formation followed the order: mouse intestine > mouse liver > human liver > rat liver ≫ rat small intestine. The UGT-catalyzed glucuronidation of EGC was much lower than that of EGCG. TheVmax/Km for (−)-EGC-3′-O-glucuronide followed the following order: mouse liver > human liver > rat liver > rat and mouse small intestine. Human UGT1A1, 1A8, and 1A9 had high activities with EGCG. UGT1A8, an intestine-specific UGT, had the highestVmax/Km for EGCG but low activity with EGC. Mice appeared to be more similar to humans than rats to humans in the glucuronidation of EGCG and EGC. Some of these catechin glucuronides retained the activities of their parent compounds in radical scavenging and in inhibiting the release of arachidonic acid from HT-29 human colon cancer cells. These results provide foundations for understanding the biotransformation and biological activities of tea catechins.

Footnotes

  • This work was supported by National Institutes of Health Grants CA56673 and CA88961.

  • Abbreviations used are::
    EGCG
    (−)-epigallocatechin gallate
    EGC
    (−)-epigallocatechin
    EGCG-7-Gluc
    (−)-EGCG-7-O-glucuronide (and similar abbreviations for other glucuronides)
    4′-MeEGC
    4′-O-methyl-(−)-epigallocatechin
    4"-MeEGCG
    4"-O-methyl-EGCG
    4′,4"-DiMeEGCG
    4′,4"-di-O-methyl-EGCG
    DPPH
    1,1-diphenyl-2-picrylhydrazyl
    UGT
    UDP-glucuronosyltransferase
    UDPGA
    uridine 5′-diphosphoglucuronic acid
    G-7896
    Escherichia coliβ-d-glucuronidase
    HLM
    human liver microsomes
    MLM
    mouse liver microsomes
    RLM
    rat liver microsomes
    LC/MS/MS
    liquid chromatography mass spectrometry
    HPLC
    high performance liquid chromatography
    • Received October 15, 2002.
    • Accepted January 3, 2002.
  • The American Society for Pharmacology and Experimental Therapeutics
View Full Text

 

DMD articles become freely available 12 months after publication, and remain freely available for 5 years. 

Non-open access articles that fall outside this five year window are available only to institutional subscribers and current ASPET members, or through the article purchase feature at the bottom of the page. 

 

  • Click here for information on institutional subscriptions.
  • Click here for information on individual ASPET membership.

 

Log in using your username and password

Forgot your user name or password?

Purchase access

You may purchase access to this article. This will require you to create an account if you don't already have one.
PreviousNext
Back to top

In this issue

Drug Metabolism and Disposition: 31 (4)
Drug Metabolism and Disposition
Vol. 31, Issue 4
1 Apr 2003
  • Table of Contents
  • About the Cover
  • Index by author
Download PDF
Article Alerts
Sign In to Email Alerts with your Email Address
Email Article

Thank you for sharing this Drug Metabolism & Disposition article.

NOTE: We request your email address only to inform the recipient that it was you who recommended this article, and that it is not junk mail. We do not retain these email addresses.

Enter multiple addresses on separate lines or separate them with commas.
Glucuronides of Tea Catechins: Enzymology of Biosynthesis and Biological Activities
(Your Name) has forwarded a page to you from Drug Metabolism & Disposition
(Your Name) thought you would be interested in this article in Drug Metabolism & Disposition.
CAPTCHA
This question is for testing whether or not you are a human visitor and to prevent automated spam submissions.
Citation Tools
Research ArticleArticle

Glucuronides of Tea Catechins: Enzymology of Biosynthesis and Biological Activities

Hong Lu, Xiaofeng Meng, Chuan Li, Shengmin Sang, Christopher Patten, Shuqun Sheng, Jungil Hong, Naisheng Bai, Bozena Winnik, Chi-Tang Ho and Chung S. Yang
Drug Metabolism and Disposition April 1, 2003, 31 (4) 452-461; DOI: https://doi.org/10.1124/dmd.31.4.452

Citation Manager Formats

  • BibTeX
  • Bookends
  • EasyBib
  • EndNote (tagged)
  • EndNote 8 (xml)
  • Medlars
  • Mendeley
  • Papers
  • RefWorks Tagged
  • Ref Manager
  • RIS
  • Zotero
Share
Research ArticleArticle

Glucuronides of Tea Catechins: Enzymology of Biosynthesis and Biological Activities

Hong Lu, Xiaofeng Meng, Chuan Li, Shengmin Sang, Christopher Patten, Shuqun Sheng, Jungil Hong, Naisheng Bai, Bozena Winnik, Chi-Tang Ho and Chung S. Yang
Drug Metabolism and Disposition April 1, 2003, 31 (4) 452-461; DOI: https://doi.org/10.1124/dmd.31.4.452
del.icio.us logo Digg logo Reddit logo Twitter logo CiteULike logo Facebook logo Google logo Mendeley logo
  • Tweet Widget
  • Facebook Like
  • Google Plus One

Jump to section

  • Article
    • Abstract
    • Materials and Methods
    • Results
    • Discussion
    • Acknowledgments
    • Footnotes
    • References
  • Figures & Data
  • Info & Metrics
  • eLetters
  • PDF

Related Articles

Cited By...

More in this TOC Section

  • Transporter-Mediated Drug-Drug Interactions for E7766
  • Human Liver Partitioning of OATP Substrates
  • Intestinal Organoid Induction Model
Show more Article

Similar Articles

  • Home
  • Alerts
Facebook   Twitter   LinkedIn   RSS

Navigate

  • Current Issue
  • Fast Forward by date
  • Fast Forward by section
  • Latest Articles
  • Archive
  • Search for Articles
  • Feedback
  • ASPET

More Information

  • About DMD
  • Editorial Board
  • Instructions to Authors
  • Submit a Manuscript
  • Customized Alerts
  • RSS Feeds
  • Subscriptions
  • Permissions
  • Terms & Conditions of Use

ASPET's Other Journals

  • Journal of Pharmacology and Experimental Therapeutics
  • Molecular Pharmacology
  • Pharmacological Reviews
  • Pharmacology Research & Perspectives
ISSN 1521-009X (Online)

Copyright © 2021 by the American Society for Pharmacology and Experimental Therapeutics