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

被引:128
作者
Sang, SM
Lambert, JD
Tian, SY
Hong, JL
Hou, Z
Ryu, JH
Stark, RE
Rosen, RT
Huang, MT
Yang, CS
Ho, CT
机构
[1] Rutgers State Univ, Ernest Mario Sch Pharm, Dept Biol Chem, Piscataway, NJ 08854 USA
[2] Rutgers State Univ, Dept Food Sci, New Brunswick, NJ 08901 USA
[3] Rutgers State Univ, Ctr Adv Food Technol, New Brunswick, NJ 08901 USA
[4] CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
[5] CUNY Coll Staten Isl, Inst Macromol Assemblies, Staten Isl, NY 10314 USA
关键词
black tea; theaflavins; benzotropolone; enzymatic synthesis; peroxidase; anti-inflammatory activities; cytotoxic activities;
D O I
10.1016/j.bmc.2003.10.024
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:459 / 467
页数:9
相关论文
共 43 条
[1]   Inhibition of PhIP mutagenicity by catechins, and by theaflavins and gallate esters [J].
Apostolides, Z ;
Balentine, DA ;
Harbowy, ME ;
Hara, Y ;
Weisburger, JH .
MUTATION RESEARCH-GENETIC TOXICOLOGY AND ENVIRONMENTAL MUTAGENESIS, 1997, 389 (2-3) :167-172
[2]   THE CHEMICAL OXIDATION OF CATECHINS AND OTHER PHENOLICS - A STUDY OF THE FORMATION OF BLACK TEA PIGMENTS [J].
BAILEY, RG ;
NURSTEN, HE ;
MCDOWELL, I .
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 1993, 63 (04) :455-464
[3]   THEAFLAVINS OF BLACK TEA [J].
COLLIER, PD ;
BRYCE, T ;
MALLOWS, R ;
THOMAS, PE ;
FROST, DJ ;
KORVER, O ;
WILKINS, CK .
TETRAHEDRON, 1973, 29 (01) :125-142
[4]   FERMENTATION OF TEA IN AQUEOUS SUSPENSION - INFLUENCE OF TEA PEROXIDASE [J].
DIX, MA ;
FAIRLEY, CJ ;
MILLIN, DJ ;
SWAINE, D .
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 1981, 32 (09) :920-932
[5]   NMR studies of molecular structure in fruit cuticle polyesters [J].
Fang, XH ;
Qiu, F ;
Yan, B ;
Wang, H ;
Mort, AJ ;
Stark, RE .
PHYTOCHEMISTRY, 2001, 57 (06) :1035-1042
[6]   Black tea polyphenols, theaflavins, prevent cellular DNA damage by inhibiting oxidative stress and suppressing cytochrome P450 1A1 in cell cultures [J].
Feng, Q ;
Torii, Y ;
Uchida, K ;
Nakamura, Y ;
Hara, Y ;
Osawa, T .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (01) :213-220
[7]   IN-VITRO STUDIES ON THE EFFECT OF POLYPHENOL OXIDASE AND PEROXIDASE ON THE FORMATION OF POLYPHENOLIC BLACK TEA CONSTITUENTS [J].
FINGER, A .
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 1994, 66 (03) :293-305
[8]  
GEISSMAN T.A., 1962, CHEMISTRY FLAVONO ED, P468
[9]  
GROSS GG, 1999, PLANT POLYPHENOLS, V2, P697
[10]   Anticlastogenic effects of black tea (World blend) and its two active polyphenols theaflavins and thearubigins in vivo in Swiss albino mice [J].
Gupta, S ;
Chaudhuri, T ;
Ganguly, DK ;
Giri, AK .
LIFE SCIENCES, 2001, 69 (23) :2735-2744