905726-67-2Relevant academic research and scientific papers
Antioxidant properties and efficacies of synthesized alkyl caffeates, ferulates, and coumarates
Sorensen, Ann-Dorit Moltke,Jacobsen, Charlotte,Durand, Erwann,Laguerre, Mickal,Bayrasy, Christelle,Lecomte, Jrme,Villeneuve, Pierre
, p. 12553 - 12562 (2015/04/21)
Caffeic, ferulic, and coumaric acids were lipophilized with saturated fatty alcohols (C1-C20). The antioxidant properties of these hydroxycinnamic acids and their alkyl esters were evaluated in various assays. Furthermore, the antioxidant efficiency of the compounds was evaluated in a simple o/w microemulsion using the conjugated autoxidizable triene (CAT) assay. All evaluated phenolipids had radical scavenging, reducing power, and metal chelating properties. Only caffeic acid and caffeates were able to form a complex with iron via their catechol group in the phenolic ring. In the o/w emulsion, the medium chain phenolipids of the three homologues series were most efficient. The antioxidant properties and efficacies were dependent upon functional groups substituted to the ring structure and were in the following order: caffeic acid and caffeates > ferulic acid and ferulates > coumaric acid and coumarates. Moreover, the results demonstrated that the test system has an impact on the antioxidative properties measured.
Antioxidant and antimicrobial activity evaluation of polyhydroxycinnamic acid ester derivatives
Venkateswarlu, Somepalli,Ramachandra, Mareullapudi S.,Krishnaraju, Alluri V.,Trimurtulu, Golakoti,Subbaraju, Gottumukkala V.
, p. 252 - 257 (2007/10/03)
Polyhydroxycinnamic acid esters 5a-p have been synthesized starting from the appropriately substituted benzaldehydes. The antioxidant activity of these esters has been determined by superoxide free radical scavenging activity and DPPH free radical scavenging activity. The SAR studies reveal that pyrogallol, catechol moieties are essential for good antioxidant activity and an increase in the length of alkyl chain of the ester decreases the activity. Butyl hydroxycinnamates exhibit higher antibacterial activity among the synthesized hydroxycinnamates 5a-p, but, none of these show significant antifungal activity.
Impact of alkyl esters of caffeic and ferulic acids on tumor cell proliferation, cyclooxygenase enzyme, and lipid peroxidation
Jayaprakasam, Bolleddula,Vanisree, Mulabagal,Zhang, Yanjun,Dewitt, David L.,Nair, Muraleedharan G.
, p. 5375 - 5381 (2008/04/03)
The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C12-caffeate), 11 (C16-caffeate), 21 (C 8-ferulate), and 23 (C12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 μg/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 μg/ mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 μg/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 μg/ mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C4-C 12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C3-C8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 μg/mL. Long-chain caffeates 11-14 (C 16-C22) and short-chain ferulates 15-20 (C 3-C5) were the most active in lipid peroxidation inhibition and showed 60-70% activity at 5 μg/mL concentration.
