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Chemical Compound Review:

m-Coumarate (E)-3-(3-hydroxyphenyl)prop- 2-enoic acid

Synonyms: PubChem8222, AC1LCUFW, CHEMBL98521, SureCN442408, H23007_ALDRICH, ...

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Disease relevance of m-Hydroxycinnamic acid

E. coli K-12 also grew with 3-hydroxycinnamic acid as sole source of carbon; the ability of cells to oxidize cinnamic and 3-phenylpropionic acids, and hydroxylated derivatives, was investigated [1].
Expression in Salmonella typhimurium of the mhp genes alone or in combination with the hca cluster allowed the growth of the recombinant bacteria in 3-hydroxycinnamic acid (3HCI) and CI, respectively [2].

High impact information on m-Hydroxycinnamic acid

The IC50 values of chlorogenic acid, gallic acid, o-coumaric acid and m-coumaric acid on 3T3-L1 preadipocytes were 72.3, 43.3, 48.2, and 49.2 microM, respectively [3].
The cell cycle assay indicated that the treatment of 3T3-L1 preadipocytes with chlorogenic acid, o-coumaric acid, and m-coumaric acid caused cell cycle arrest in the G1 phase [3].
Caffeic acid (3,4-dihydroxycinnamic acid) was the strongest antioxidant amongst cinnamate derivatives with a SA(HP) = 8.2 microM(-1), as opposed to m-coumaric acid (2-hydroxycinnamic acid), which was found to be a poor hydrogen peroxide scavenger (SA(HP) = 0.18 microM(-1)) [4].
Furthermore, m-coumaric acid and 3-(m-hydroxyphenyl)propionic acid, the main metabolites of chlorogenic and caffeic acid by colonic microflora, competitively inhibited the transport of fluorescein, a known substrate of MCT [5].
The proton-coupled directional transport of m-coumaric acid, mHPP, and DHPP was observed, and the transport was inhibited by an MCT substrate [6].

Biological context of m-Hydroxycinnamic acid

However, m-coumaric acid displayed the strongest activity (IC50 = 63.31 microM) and induced uncompetitive inhibition with respect to the substrate xanthine (Ki = 21.568 microM) [7].
The present studies were undertaken to analyze the factors regulating 3-hydroxycinnamic acid-induced apoptosis and cell cycle arrest [8].
Enzymatic hydroxylation of m-coumaric acid by mice liver hydroxylase [9].

Anatomical context of m-Hydroxycinnamic acid

The percentage of apoptosis induced by 3-hydroxycinnamic acid in HeLa cells was increased with incubation time [8].
Induction of G0/G1 arrest and apoptosis by 3-hydroxycinnamic acid in human cervix epithelial carcinoma (HeLa) cells [8].

Associations of m-Hydroxycinnamic acid with other chemical compounds

It was previously reported that m-coumaric acid, m-hydroxyphenylpropionic acid (mHPP), and 3,4-dihydroxyphenylpropionic acid (DHPP) are major metabolites of ingested caffeic acid formed by gut microflora and would be transported by the monocarboxylic acid transporter (MCT) [6].

Gene context of m-Hydroxycinnamic acid

The results also demonstrated that 3-hydroxycinnamic acid increased the expression of p53, caspase-3, Bax and cyclin B. These results demonstrated that 3-hydroxycinnamic acid induced apoptosis through p53- and caspase-3-dependent pathways [8].
Kinetic study on the slow inhibition of epidermis tyrosinase by m-coumaric acid [10].

References

Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli. Burlingame, R., Chapman, P.J. J. Bacteriol. (1983) [Pubmed]
Characterization of the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid in Escherichia coli K-12. Díaz, E., Ferrández, A., García, J.L. J. Bacteriol. (1998) [Pubmed]
Inhibitory effect of phenolic acids on the proliferation of 3T3-L1 preadipocytes in relation to their antioxidant activity. Hsu, C.L., Huang, S.L., Yen, G.C. J. Agric. Food Chem. (2006) [Pubmed]
Determination of hydrogen peroxide scavenging activity of cinnamic and benzoic acids employing a highly sensitive peroxyoxalate chemiluminescence-based assay: structure-activity relationships. Mansouri, A., Makris, D.P., Kefalas, P. Journal of pharmaceutical and biomedical analysis. (2005) [Pubmed]
Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal caco-2 cell monolayers. Konishi, Y., Kobayashi, S. J. Agric. Food Chem. (2004) [Pubmed]
Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. Konishi, Y., Kobayashi, S. J. Agric. Food Chem. (2004) [Pubmed]
Structure-activity relationship of caffeic acid analogues on xanthine oxidase inhibition. Chan, W.S., Wen, P.C., Chiang, H.C. Anticancer Res. (1995) [Pubmed]
Induction of G0/G1 arrest and apoptosis by 3-hydroxycinnamic acid in human cervix epithelial carcinoma (HeLa) cells. Chuang, J.Y., Tsai, Y.Y., Chen, S.C., Hsieh, T.J., Chung, J.G. In Vivo (2005) [Pubmed]
Enzymatic hydroxylation of m-coumaric acid by mice liver hydroxylase. Bajaj, K.L., Singh, J., Chakravarti, P. Indian J. Exp. Biol. (1977) [Pubmed]
Kinetic study on the slow inhibition of epidermis tyrosinase by m-coumaric acid. Cabanes, J., García-Carmona, F., García-Cánovas, F., Iborra, J.L., Lozano, J.A. Biochim. Biophys. Acta (1984) [Pubmed]

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