94530-69-5Relevant articles and documents
Coumaric acid derivatives as tyrosinase inhibitors: Efficacy studies through in silico, in vitro and ex vivo approaches
Fernandes, Jo?o Paulo S.,Ferrarini, Márcio,Mercaldi, Vitória Gallo,Nazato, Lucas Idacir Sbrugnera,Padovani, Giovana,Sufi, Bianca da Silva,Varela, Marina Themoteo
, (2020/08/06)
p-Coumaric acid is a known inhibitor of tyrosinase, an enzyme involved in the initial steps of the melanin synthesis in human and other species. However, its low lipophilicity impairs its penetration through skin and efficacy as antimelanogenic agent indeed. Accordingly, this paper reports the assessment of several coumaric acid derivatives as tyrosinase inhibitors and antimelanogenic agents in in vitro, in silico and ex vivo assays. The compounds were designed with modifications in the aromatic and acid moieties of p-coumaric acid, being the coumarate esters the most promising derivatives. The compounds showed higher tyrosinase inhibitory activity (pIC50 3.7–4.2) than the parent acid, being compounds 1d, 1e and 1f the most potent inhibitors. Docking analysis showed that these esters are competitive inhibitors per se, and act independently of a redox mechanism as suggested by DPPH assays. Moreover, the esters showed efficacy in reducing the melanin deposition in human skin fragments at 0.1% concentration, especially compound 1e. In summary, there is an important equilibria between tyrosinase affinity and lipophilicity that must be considered to get effective antimelanogenic agents with adequate permeability in the skin.
Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain
Zhu, Fengxian,Xu, Zhongming,Yonekura, Lina,Yang, Ronghua,Tamura, Hirotoshi
, p. 1178 - 1182 (2015/10/05)
Methyl, propyl and hexyl esters of rosmarinic, caffeic and p-coumaric acids were tested for antiallergic activity, and rosmarinic acid propyl ester exhibited the greatest β-hexosaminidase release suppression (IC50, 23.7 μM). Quadratic correlations between pIC50 and cLogP (r2 = 0.94, 0.98, and 1.00, respectively) were observed in each acid ester series. The antiallergic activity is modulated by hydrophobicity, and alkyl chain bulkiness.
Synthesis of alkyl coumarate esters by celite-bound lipase of Bacillus licheniformis SCD11501
Sharma, Shivika,Dogra, Priyanka,Chauhan, Ghanshyam S.,Kanwar, Shamsher S.
, p. 80 - 86 (2014/02/14)
Coumaric acid and its derivatives are known to inhibit UV-induced melanogenesis, skin erythema, angiogenesis, platelet accumulation and osteoclastogenesis besides regulation of bone formation, anti-oxidant and anti-microbial activities. The present study is a novel piece of work in which the syntheses of a series of alkyl coumarates (methyl coumarate, ethyl coumarate, propyl coumarate and butyl coumarate) have been achieved using celite-immobilized lipase of Bacillus licheniformis strain SCD11501 in a water-free medium at 55 C under shaking in a chemical reactor. The maximum yield(s) of coumaric acid based esters i.e. methyl coumarate (69.0%), ethyl coumarate (63.1%), n-propyl coumarate (59.8%) and n-butyl coumarate (55.1%) using celite-immobilized lipase could be achieved after optimizing various reaction parameters such as incubation time, incubation temperature, relative molar concentration of reactants, biocatalyst concentration and amount of molecular sieves added to the reaction system. Molecular sieves had an important effect on the ester synthesis resulting in an enhanced yield. Maximum yield was recorded for methyl coumarate (69.0%) possibly because methyl group causes less stearic hindrance to the catalytic site of the lipase due to which it becomes more accessible for immobilized lipase to undergo esterification. The characterization of synthesized esters was done through FTIR spectroscopy and 1H NMR spectra.
