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Rapid CommunicationShort Communication

Formation and Identification of 4′-O-Methyl-(−)-Epigallocatechin in Humans

Xiaofeng Meng, Mao-Jung Lee, Chuan Li, Shuqun Sheng, Nanqun Zhu, Shengmin Sang, Chi-Tang Ho and Chung S. Yang
Drug Metabolism and Disposition June 2001, 29 (6) 789-793;
Xiaofeng Meng
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Mao-Jung Lee
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Chuan Li
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Shuqun Sheng
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Nanqun Zhu
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Shengmin Sang
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Chi-Tang Ho
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Chung S. Yang
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Abstract

The possible beneficial effects of tea consumption have attracted a great deal of attention. Many of the biological effects have been attributed to tea catechins, but the metabolic fate of these compounds is not clear. In the present study, a major metabolite observed in human blood and urine samples after green tea administration was identified as a O-methylated derivative of (−)-epigallocatechin (EGC) by comparison with products from chemical and enzymatic O-methylation of EGC. The structure of this metabolite was elucidated as 4′-O-methyl-(−)-epigallocatechin (4′-O-MeEGC) by 1H and 13C NMR and heteronuclear multiple bond connectivity experiment. The human plasma level of 4′-O-MeEGC reached its peak value within the first 2 h following tea ingestion. Its maximum concentration was 4 to 6 times higher than that of EGC. The half-lives of EGC and 4′-O-MeEGC in the blood were 1.02 ± 0.07 and 4.39 ± 1.14 h, respectively. The amount of 4′-O-MeEGC excreted in urine was about 3 times higher than that of EGC, and 88% of 4′-O-MeEGC was excreted in urine within 8 h. The present structural information and concentration-time profile of this metabolite provide the basis for understanding the biotransformation of EGC and for future elucidation of its biological activities.

Footnotes

  • Send reprint requests to: Dr. Chung S. Yang, Laboratory for Cancer Research, College of Pharmacy, Rutgers, The State University of New Jersey, 164 Frelinghuysen Rd., Piscataway, NJ 08854-8020. E-mail: csyang{at}rci.rutgers.edu

  • The study was supported by the National Institutes of Health Grant CA 56673.

  • Abbreviations used are::
    EGC
    (−)-epigallocatechin
    EGCG
    (−)-epigallocatechin-3-gallate
    EC
    (−)-epicatechin
    ECG
    (−)-epicatechin-3-gallate
    HPLC
    high-performance liquid chromatography
    CEAS
    coulochem electrode array system
    LC/MS
    liquid chromatography/mass spectrometry
    MS/MS
    tandem mass spectrometry
    ESI
    electrospray ionization
    COMT
    catechol-O-methyltransferase
    SAM
    S-adenosyl-l-methionine
    MeEGC
    mono-O-methylated EGC
    tR
    retention time
    • Received August 27, 2000.
    • Accepted February 22, 2001.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 29 (6)
Drug Metabolism and Disposition
Vol. 29, Issue 6
1 Jun 2001
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Rapid CommunicationShort Communication

Formation and Identification of 4′-O-Methyl-(−)-Epigallocatechin in Humans

Xiaofeng Meng, Mao-Jung Lee, Chuan Li, Shuqun Sheng, Nanqun Zhu, Shengmin Sang, Chi-Tang Ho and Chung S. Yang
Drug Metabolism and Disposition June 1, 2001, 29 (6) 789-793;

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Rapid CommunicationShort Communication

Formation and Identification of 4′-O-Methyl-(−)-Epigallocatechin in Humans

Xiaofeng Meng, Mao-Jung Lee, Chuan Li, Shuqun Sheng, Nanqun Zhu, Shengmin Sang, Chi-Tang Ho and Chung S. Yang
Drug Metabolism and Disposition June 1, 2001, 29 (6) 789-793;
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