Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

Joshua D. Lambert; Joseph E. Rice; Jungil Hong; Zhe Hou; Chung S. Yang

doi:10.1016/j.bmcl.2004.12.070

Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

Joshua D. Lambert, Joseph E. Rice, Jungil Hong, Zhe Hou, Chung S. Yang

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100 Scopus citations

Abstract

Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 μM.

Original language	English (US)
Pages (from-to)	873-876
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	4
DOIs	https://doi.org/10.1016/j.bmcl.2004.12.070
State	Published - Feb 15 2005

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Keywords

Antiinflammatory
Green tea
Growth inhibition
Lactones
Synthesis

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10.1016/j.bmcl.2004.12.070

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title = "Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives",

abstract = "Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 μM.",

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T1 - Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

AU - Lambert, Joshua D.

AU - Rice, Joseph E.

AU - Hong, Jungil

AU - Hou, Zhe

AU - Yang, Chung S.

N1 - Funding Information: This study was supported by NIH Grant CA88961 (CSY).

PY - 2005/2/15

Y1 - 2005/2/15

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AB - Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 μM.

KW - Antiinflammatory

KW - Green tea

KW - Growth inhibition

KW - Lactones

KW - Synthesis

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JO - Bioorganic and Medicinal Chemistry Letters

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Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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