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

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

144 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.

Original language	English (US)
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

All Science Journal Classification (ASJC) codes

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

UN SDGs

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

Access to Document

10.1016/j.bmc.2003.10.024

Cite this

@article{7c6428ae78774b8f9defd36b6898192b,

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.",

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

note = "Funding Information: This work was supported by NIH Grant PO1 CA88961 and New Jersey Commission on Science and Technology. Funds to purchase the 600 MHz NMR spectrometer at CUNY College of Staten Island were provided by the New York State Dormitory Authority and the New York State Higher Education Applied Technology Program.",

year = "2004",

month = jan,

day = "15",

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

language = "English (US)",

volume = "12",

pages = "459--467",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd",

number = "2",

}

TY - JOUR

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

N1 - Funding Information: This work was supported by NIH Grant PO1 CA88961 and New Jersey Commission on Science and Technology. Funds to purchase the 600 MHz NMR spectrometer at CUNY College of Staten Island were provided by the New York State Dormitory Authority and the New York State Higher Education Applied Technology Program.

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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0347320708&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0347320708&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2003.10.024

DO - 10.1016/j.bmc.2003.10.024

M3 - Article

C2 - 14723964

AN - SCOPUS:0347320708

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

All Science Journal Classification (ASJC) codes

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this