Anticancer Activity of Phenolic Acids of Natural or Synthetic Origin:  A Structure−Activity Study

Abstract

Several phenolic acids-caffeic and gallic acid derivatives-were synthesized and screened for their potential antiproliferative and cytotoxic properties, in different human cancer cell lines: mammary gland and cervix adenocarcinomas and lymphoblastic leukemia. The selected phenols were structurally related, which allowed us to gather important information regarding the structure-activity relationships underlying the biological activity of such compounds. This is proposed to be due to a balance between the antioxidant and pro-oxidant properties of this kind of agent. Distinct effects were found for different cell lines, which points to a significant specificity of action of the drugs tested. It was verified, for the types of cancer investigated, that the trihydroxylated derivatives yielded better results than the dihydroxylated ones. Tests in noncancerous cells, human lung fibroblasts, were also undertaken, in view of determining the toxic side effects of the compounds studied.

Crataegus monogyna buds and fruits phenolic extracts: Growth inhibitory activity on human tumor cell lines and chemical characterization by HPLC–DAD–ESI/MS

“…Also phenolic acids, such as gallic and caffeic acid derivatives had shown antiproliferative effect toward HeLa cervix adenocarcinoma, breast cancer and leukemia cell lines (Gomes et al, 2003). Furthermore, it was demonstrated that treatment of MCF-7 and MAD-MB-231 human breast cancer cells with caffeic acid or chlorogenic acid partially inhibited the methylation of the promoter region of the RARb gene (De, Baltas & Bedos-Belval, 2011).…”

New insights on the anticancer properties of dietary polyphenols

“…[10][11][12][13] Naturally occurring phenolic acids and analogs (e.g., caffeic and gallic acids) are known to display a wide variety of biological functions, in addition to their primary antioxidant activity, which are mainly related to modulation of carcinogenesis. [10][11][12][13] Thus, phenolic derivatives have lately received increased attention, namely the ones which are taken exogenously from the diet (as nutritional supplements).…”

“…Several types of hydroxybenzoic and hydroxycinnamic acids have been identified in the human diet, and are known to play an important role due to their abundance and diversity. Natural phenolic acids, either occurring in the free or conjugated forms, usually appear as esters or amides 12,13 (Table I). Due to their structural similarity, several other polyphenols are considered as acid analogs (Table I).…”

Antioxidant phenolic esters with potential anticancer activity: solution equilibria studied by Raman spectroscopy

“…[1 -5] In particular, phenolic antioxidant compounds are capable of preventing or inhibiting carcinogenesis at different levels, by distinct mechanisms, thereby reducing the risk and/or progression of certain types of cancer. [6,7] Accordingly, a growing interest in phenolic antioxidant agents is emerging, aiming at the prevention of numerous diseases mainly caused by the occurrence of deleterious free radical species. [6,8 -12] For phenolic acid derivatives such as hydroxycinnamic and hydroxybenzoic n-alkyl esters, either of natural or synthetic origin, the presence of the ring substituent hydroxyl groups is known to be an essential chemical feature for their particular biological profile, while the influence of the nature of both the pendant carbon chain and the ester moiety is still controversial.…”