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Comparison of a Pair of Synthetic Tea‐Catechin‐Derived Epimers: Synthesis, Antifolate Activity, and Tyrosinase‐Mediated Activation in Melanoma
Author(s) -
SáezAyala Magalí,
SánchezdelCampo Luis,
Montenegro María F.,
Chazarra Soledad,
Tárraga Alberto,
CabezasHerrera Juan,
RodríguezLópez José Neptuno
Publication year - 2011
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201000482
Subject(s) - catechin , tyrosinase , epimer , chemistry , stereochemistry , biochemistry , combinatorial chemistry , enzyme , polyphenol , antioxidant
Despite bioavailability issues, tea catechins have emerged as promising chemopreventive agents because of their efficacy in various animal models. We synthesized two catechin‐derived compounds, 3‐ O ‐(3,4,5‐trimethoxybenzoyl)‐(−)‐catechin (TMCG) and 3‐ O ‐(3,4,5‐trimethoxybenzoyl)‐(−)‐epicatechin (TMECG), in an attempt to improve the stability and cellular absorption of tea polyphenols. The antiproliferative and pro‐apoptotic activities of both compounds were analyzed with various cancer cell systems, and TMCG, which was easily synthesized in excellent yield, was more active than TMECG in both melanoma and non‐melanoma cell lines. TMCG was also a better inhibitor of dihydrofolate reductase and was more efficiently oxidized by tyrosinase, potentially explaining the difference in activity between these epimers.