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

Research output: Contribution to journal › Article › peer-review

101 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

Access to Document

10.1016/j.bmcl.2004.12.070

Cite this

@article{5a7a787deb5e44ebbd811e5cfceda6a1,

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.",

author = "Lambert, \{Joshua D.\} and Rice, \{Joseph E.\} and Jungil Hong and Zhe Hou and Yang, \{Chung S.\}",

note = "Funding Information: This study was supported by NIH Grant CA88961 (CSY).",

year = "2005",

month = feb,

day = "15",

doi = "10.1016/j.bmcl.2004.12.070",

language = "English (US)",

volume = "15",

pages = "873--876",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "4",

}

TY - JOUR

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

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/16244391107

UR - https://www.scopus.com/pages/publications/16244391107#tab=citedBy

U2 - 10.1016/j.bmcl.2004.12.070

DO - 10.1016/j.bmcl.2004.12.070

M3 - Article

C2 - 15686878

AN - SCOPUS:16244391107

SN - 0960-894X

VL - 15

SP - 873

EP - 876

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 4

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this