Synthesis of N-hydroxycinnamoyl amide derivatives and evaluation of their anti-oxidative and anti-tyrosinase activities

Huang, 2006, Inhibition of the activity of mushroom tyrosinase by alkylbenzoic acids, Food Chem, 94, 1, 10.1016/j.foodchem.2004.09.008 Martinez, 1995, The biochemistry and control of enzymatic browning, Trends Food Sci Technol, 6, 195, 10.1016/S0924-2244(00)89054-8 Sang JL, Hann SK, Im S. The pigmentary system: physiology and pathophysiology, second edition. Tidsskrift for Den Norske Legeforening, 2015;86(9):618-621. Stefania, 2010, Chemical and instrumental approaches to treat hyperpigmentation, Pigment Cell & Melanoma Res, 16, 101 Wei, 2012, Synthesis of N -hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities, Med Chem Res, 21, 1905, 10.1007/s00044-011-9713-2 Gulcin, 2006, Antioxidant activity of caffeic acid (3, 4-dihydroxycinnamic acid), Toxicology, 217, 213, 10.1016/j.tox.2005.09.011 Cheng, 2006, Structure–activity relationship studies of resveratrol and its analogues by the reaction kinetics of low density lipoprotein peroxidation, Bioorg Chem, 34, 142, 10.1016/j.bioorg.2006.04.001 Chochkova, 2013, N -Hydroxycinnamoyl amides of fluorinated amino acids: synthesis, anti-tyrosinase and DPPH scavenging activities, J Fluorine Chem, 156, 203, 10.1016/j.jfluchem.2013.09.013 Zhao, 2008, Chemistry, natural sources, dietary intake and pharmacokinetic properties of ferulic acid: a review, Food Chem, 109, 691, 10.1016/j.foodchem.2008.02.039 Mattila, 2005, Contents of phenolic acids, alkyl- and alkenylresorcinols, and avenanthramides in commercial grain products, J Agric Food Chem, 53, 8290, 10.1021/jf051437z Mattila, 2006, Phenolic acids in berries, fruits, and beverages, J Agric Food Chem, 54, 7193, 10.1021/jf0615247 Clifford, 1999, Chlorogenic acids and other cinnamates &ndash; nature, occurrence and dietary burden, J Sci Food Agric, 79, 362, 10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D Pei, 2015, P-Coumaric acid and its conjugates: dietary sources, pharmacokinetic properties and biological activities, J Sci Food Agric, 96, 2952, 10.1002/jsfa.7578 Martin-Tanguy, 1985, The occurrence and possible function of hydroxycinnamoyl acid amides in plants, Plant Growth Regul, 3, 381, 10.1007/BF00117595 Shi, 2005, Inhibitory effects of cinnamic acid and its derivatives on the diphenolase activity of mushroom (Agaricus bisporus) tyrosinase, Food Chem, 92, 707, 10.1016/j.foodchem.2004.08.031 Spasova, 2008, Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities, Bioorg Med Chem, 16, 7457, 10.1016/j.bmc.2008.06.010 Lee, 2003, Anti-atherogenic effects of 3,4-Dihydroxy hydrocinnamides, Cheminform, 13, 2681 Rajan, 2001, Synthesis and evaluation of caffeic acid amides as antioxidants, Bioorg Med Chem Lett, 11, 215, 10.1016/S0960-894X(00)00630-2 Kim, 2012, Anti-inflammatory activity of hydroxycinnamic acid derivatives isolated from corn bran in lipopolysaccharide-stimulated Raw 264.7 macrophages, Food Chem Toxicol, 50, 1309, 10.1016/j.fct.2012.02.011 Chuang, 2015, KS370G, a caffeamide derivative, attenuates unilateral ureteral obstruction-induced renal fibrosis by the reduction of inflammation and oxidative stress in mice, Eur J Pharmacol, 750, 1, 10.1016/j.ejphar.2015.01.020 Kuo, 2017, N-(4-bromophenethyl) caffeamide protects skin from UVB-induced inflammation through MAPK/IL-6/NF-ΰB-dependent signaling in human skin fibroblasts and hairless mouse skin, Molecules, 22, 1639, 10.3390/molecules22101639 Hoshino, 2003, Synthesis of amide compounds of ferulic acid, and their stimulatory effects on insulin secretion in vitro, Bioorg Med Chem, 11, 3807, 10.1016/S0968-0896(03)00280-3 Wang, 2019, Synthesis and antioxidation of caffeic acid amino acid ethyl ester, Fine Chemicals, 36, 494 Fan, 2012, Tyrosinase inhibitory effects and antioxidative activities of novel cinnamoyl amides with amino acid ester moiety, Food Chem, 134, 1081, 10.1016/j.foodchem.2012.03.021 Hung, 2005, Evaluation of caffeic acid amide analogues as anti-platelet aggregation and anti-oxidative agents, Bioorg Med Chem, 13, 1791, 10.1016/j.bmc.2004.11.055 Treml, 2016, Flavonoids as potent scavengers of hydroxyl radicals, Compr Rev Food Sci Food Saf, 15, 720, 10.1111/1541-4337.12204 Gmez-cordov, 2001, Effects of wine phenolics and sorghum tannins on tyrosinase activity and growth of melanoma cells, J Agric Food Chem, 49, 1620, 10.1021/jf001116h Spasova, 2010, Synthesis of cinnamoyl and hydroxycinnamoyl amino acid conjugates and evaluation of their antioxidant activity, J Pept Sci, 12, 369, 10.1002/psc.736 Wang, 2019, Study on chemical modification of caffeic acid and antioxidation of products, China Surfactant Detergent & Cosmetics, 49, 98 Anselmi, 2004, Conformational analysis: a tool for the elucidation of the antioxidant properties of ferulic acid derivatives in membrane models, J Pharm Biomed Anal, 35, 1241, 10.1016/j.jpba.2004.04.008 Boath, 2012, Berry components inhibit α-glucosidase in vitro: synergies between acarbose and polyphenols from black currant and rowanberry, Food Chem, 135, 929, 10.1016/j.foodchem.2012.06.065