Tyrosinase inhibitory effects and antioxidative activities of novel cinnamoyl amides with amino acid ester moiety

Food Chemistry

Volumn 134, Issue 2, 2012, Pages 1081-1087

  Fan, Qian ^a   Jiang, Hong ^b   Yuan, Er Dong ^a   Zhang, Jian Xun ^c   Ning, Zheng Xiang ^a   Qi, Sui Jian ^a   Wei, Qing Yi ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b HUAZHONG AGRICULTURAL UNIVERSITY   (China)

^c Yichang Humanwell Pharmaceutical Co Ltd   (China)

Author keywords

Antioxidative activities; Cinnamoyl amides with amino acid ester (CAAE) moiety; Tyrosinase inhibitory activity

Indexed keywords

AMINO ACID ESTERS; ANTI OXIDATIVE ACTIVITY; ANTIOXIDANT ACTIVITIES; CAFFEIC ACIDS; CINNAMIC ACIDS; FERULIC ACIDS; HYDROCARBON CHAINS; HYDROXYL RADICALS; INHIBITION MECHANISMS; INHIBITORY ACTIVITY; INHIBITORY EFFECT; MUSHROOM TYROSINASE; PEROXIDATION; STRUCTURE-ACTIVITY RELATIONSHIPS; TYROSINASE INHIBITORY ACTIVITIES;

AMIDES; ESTERIFICATION; ESTERS; HYDROCARBONS; STYRENE;

AMINO ACIDS;

4 HYDROXY CINNAMIC ACID; ANTIOXIDANT; BUTYL N (3 PHENYL 1 OXO 2 PROPEN 1 YL)GLYCINATE; CAFFEIC ACID; CINNAMIC ACID; FERULIC ACID; ISOPROPYL N (3 PHENYL 1 OXO 2 PROPEN 1 YL)GLYCINATE; LEVODOPA; METHYL N (3 PHENYL 1 OXO 2 PROPEN 1 YL)GLYCINATE; MONOPHENOL MONOOXYGENASE; PROPYL N (3 PHENYL 1 OXO 2 PROPEN 1 YL)GLYCINATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; FEMALE; IC 50; LIPID PEROXIDATION; NONHUMAN; RAT; SPECTROPHOTOMETRY; STRUCTURE ACTIVITY RELATION;

AGARICALES; AMIDES; AMINO ACIDS; ANTIOXIDANTS; CINNAMATES; ENZYME INHIBITORS; ESTERS; FUNGAL PROTEINS; MOLECULAR STRUCTURE; MONOPHENOL MONOOXYGENASE; STRUCTURE-ACTIVITY RELATIONSHIP;

BASIDIOMYCOTA;

EID: 84862831788     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.03.021     Document Type: Article

References (26)

1. Q.X. Chen, K.K. Song, L. Qiu, X.D. Liu, H. Huang, and H.Y. Gao Inhibitory effects on mushroom tyrosinase by p-alkoxybenzoic acids Food Chemistry 91 2005 269 274
2. M.N. Clifford Chlorogenic acids and other cinnamates: Nature, occurrence and dietary burden Journal of the Science of Food and Agriculture 79 1999 362 372
3. C. Gómez-Cordovés, B. Bartolomé, W. Vieira, and V.M. Virador Effects of wine phenolics and sorghum tannins on tyrosinase activity and growth of melanoma cells Journal of Agricultural and Food Chemistry 49 2001 1620 1624
4. X.H. Huang, Q.X. Chen, Q. Wang, K.K. Song, J. Wang, L. Sha, and X. Guan Inhibition of the activity of mushroom tyrosinase by alkylbenzoic acids Food Chemistry 94 1 2006 1 6
5. S. Khatib, O. Nerya, R. Musa, S. Tamir, T. Pete, and J. Vaya Enhanced substituted resorcinol hydrophobicity augments tyrosinase inhibition potency Journal of Medicinal Chemistry 50 2007 2676 2681
6. J. Kim, M.R. Marshall, and C. Wei Polyphenoloxidase N.F. Haard, B.K. Simpson, Seafood enzyme utilization and influence on post harvest seafood quality 2000 Marcel Dekker New York 271 315
7. J.E. Kinsella, E. Frankel, B. German, and J. Kanner Possible mechanisms for the protective role of antioxidants in wine and plant foods Food Technology 47 4 1993 85 89
8. P.A. Kroon, and G. Williamson Hydroxycinnamates in plants and food: Current and future perspectives Journal of the Science of Food and Agriculture 79 1999 355 361
9. I. Kubo, and I. Kinst-Hori Flavonols from saffron flower: Tyrosinase inhibitory activity and inhibition mechanism Journal of Agricultural and Food Chemistry 47 1999 4121 4125
10. H.S. Lee Tyrosinase inhibitors of Pulsatilla cernua root-derived materials Journal of Agricultural and Food Chemistry 50 2002 1400 1403
11. O.H. Lowry, M.J. Rosebrough, A. Farr, and R.J. Randall Protein measurement with the folin phenol reagent Journal of Biological Chemistry 193 1951 265 275
12. M.V. Martinez, and J.R. Whitaker The biochemistry and control of enzymatic browning Trends in Food Science and Technology 6 1995 195 200
13. Y. Matoba, T. Kumagai, A. Yamamoto, H. Yoshitsu, and M. Sugiyama Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis Journal of Biological Chemistry 281 2006 8980 8990
14. A.M. Mayer Polyphenol oxidases in plants-recent progress Phytochemistry 26 1995 11 20
15. N.P. Nirmal, and S. Benjakul Effect of ferulic acid on inhibition of polyphenoloxidase and quality changes of Pacific white shrimp (Litopenaeus vannamei) during iced storage Food Chemistry 116 2009 323 331
16. J.M. Noh, S.Y. Kwak, H.S. Seo, J.H. Seo, B.G. Kim, and Y.S. Lee Kojic acid-amino acid conjugates as tyrosinase inhibitors Bioorganic & Medicinal Chemistry Letters 19 2009 5586 5589
17. J.M. Noh, and Y.S. Lee Inhibitory activities of hydroxyphenolic acid-amino acid conjugates on tyrosinase Food Chemistry 125 2011 953 957
18. S. Okombi, D. Rival, S. Bonnet, A.M. Mariotte, E. Perrier, and A. Boumendjel Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase Bioorganic & Medicinal Chemistry Letters 16 2006 2252 2255
19. H. Okutana, N. Ozcelikb, H. Ramazan Yilmaz, and E. Uz Effects of caffeic acid phenethyl ester on lipid peroxidation and antioxidant enzymes in diabetic rat heart Clinical Biochemistry 38 2005 191 196
20. M. Orlandi, B. Rindone, G. Molteni, P. Rummakko, and G. Brunow Asymmetric biomimetic oxidations of phenols: The mechanism of the diastereo- and enantioselective synthesis of dehydrodiconiferyl ferulate (DDF) and dehydrodiconiferyl alcohol (DDA) Tetrahedron 57 2001 371 378
21. L. Qiu, Q.H. Chen, J.X. Zhuang, X. Zhong, J.J. Zhou, and Y.J. Guo Inhibitory effects of α-cyano-4-hydroxy cinnamic acid on the activity of mushroom tyrosinase Food Chemistry 112 2009 609 613
22. J.S. Roh, J.Y. Han, J.H. Kim, and J.K. Hwang Inhibitory effects of active compounds isolated from safflower (Carthamus tinctorius L.) seeds for melanogenesis Biological & Pharmaceutical Bulletin 27 2004 1976
23. Y. Shi, Q.X. Chen, Q. Wang, K.K. Song, and L. Qiu Inhibitory effects of cinnamic acid and its derivatives on the diphenolase activity of mushroom (Agaricus bisporus) tyrosinase Food Chemistry 92 4 2005 707 712
24. Q.Y. Wei, W.F. Chen, B. Zhou, L. Yang, and Z.L. Liu Inhibition of lipid peroxidation and protein oxidation in rat liver mitochondria by curcumin and its analogues Biochimica et Biophysica Acta 1760 2006 70 77
25. Wei, Q. Y., Jiang, H., Zhang, J. X., Guo, P. F., & Wang, H. (in press) Synthesis of N-hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities. Medicinal Chemistry Research. http://dx.doi.org/10.1007/s00044-011-9713-2.
26. W. Yi, X.Q. Wu, R.H. Cao, H.C. Song, and L. Ma Biological evaluations of novel vitamin C esters as mushroom tyrosinase inhibitors and antioxidants Food Chemistry 117 2009 381 386