Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities

Shengmin Sang; Joshua D. Lambert; Shiying Tian; Jungil Hong; Zhe Hou; Jae-He Ryu; Ruth E. Stark; Robert T. Rosen; Mou-Tuan Huang; Chung S. Yang; Chi-Tang Ho

doi:10.1016/j.bmc.2003.10.024

Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities

Shengmin Sang
, Joshua D. Lambert
, Shiying Tian
, Jungil Hong
, Zhe Hou
, Jae-He Ryu
, Ruth E. Stark
, Robert T. Rosen
, Mou-Tuan Huang
, Chung S. Yang
, Chi-Tang Ho

Family and Consumer Sciences

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

147 Scopus citations

Abstract

Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activites against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. © 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	459-467
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	12
Issue number	2
DOIs	https://doi.org/10.1016/j.bmc.2003.10.024
State	Published - Jan 15 2004

Keywords

Anti-inflammatory activities
Benzotropolone
Black tea
Cytotoxic activities
Enzymatic synthesis
Peroxidase
Theaflavins

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2003.10.024

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title = "Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities",

abstract = "Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activites against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. {\textcopyright} 2003 Elsevier Ltd. All rights reserved.",

keywords = "Anti-inflammatory activities, Benzotropolone, Black tea, Cytotoxic activities, Enzymatic synthesis, Peroxidase, Theaflavins",

author = "Shengmin Sang and Lambert, \{Joshua D.\} and Shiying Tian and Jungil Hong and Zhe Hou and Jae-He Ryu and Stark, \{Ruth E.\} and Rosen, \{Robert T.\} and Mou-Tuan Huang and Yang, \{Chung S.\} and Chi-Tang Ho",

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doi = "10.1016/j.bmc.2003.10.024",

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journal = "Bioorganic and Medicinal Chemistry",

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T1 - Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities

AU - Sang, Shengmin

AU - Lambert, Joshua D.

AU - Tian, Shiying

AU - Hong, Jungil

AU - Hou, Zhe

AU - Ryu, Jae-He

AU - Stark, Ruth E.

AU - Rosen, Robert T.

AU - Huang, Mou-Tuan

AU - Yang, Chung S.

AU - Ho, Chi-Tang

PY - 2004/1/15

Y1 - 2004/1/15

N2 - Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activites against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. © 2003 Elsevier Ltd. All rights reserved.

AB - Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activites against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. © 2003 Elsevier Ltd. All rights reserved.

KW - Anti-inflammatory activities

KW - Benzotropolone

KW - Black tea

KW - Cytotoxic activities

KW - Enzymatic synthesis

KW - Peroxidase

KW - Theaflavins

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DO - 10.1016/j.bmc.2003.10.024

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SN - 0968-0896

VL - 12

SP - 459

EP - 467

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 2

ER -

Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities

Abstract

Keywords

UN SDGs

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