Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides

Medicinal Chemistry Research

Volumn 22, Issue 9, 2013, Pages 4173-4182

  Georgiev, Lyubomir ^a   Chochkova, Maya ^a   Totseva, Iskra ^b   Seizova, Katya ^b   Marinova, Emma ^b   Ivanova, Galya ^c   Ninova, Mariana ^d   Najdenski, Hristo ^d   Milkova, Tsenka ^a  

^a SOUTH WEST UNIVERSITY NEOFIT RILSKI   (Bulgaria)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^c UNIVERSITY OF PORTO   (Portugal)

^d INSTITUTE OF MICROBIOLOGY   (Bulgaria)

Author keywords

Antimicrobial activity; Antioxidant activity; Monophenolase activity; Mushroom tyrosinase; N hydroxycinnamoylamides

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; AMIDE; CINNAMIC ACID; HYDROXYCINNAMOYLAMIDE; LIPID; MONOPHENOL MONOOXYGENASE; UNCLASSIFIED DRUG;

ANTI TYROSINASE ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; IN VITRO STUDY; LIPID PEROXIDATION; NONHUMAN; STRUCTURE ACTIVITY RELATION;

EID: 84881143697     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0419-x     Document Type: Article

References (34)

1. Chochkova MG, Chorbadzhiyska EY, Ivanova GI, Najdenski H, Ninova M, Milkova T (2012) Antimicrobial and radical scavenging activities of N-hydroxycinnamoyl-l-cysteine and -l-proline ethyl ester. Nat Prod J 2:50-54
2. Crohns M (2010) Antioxidants, cytokines and markers of oxidative stress in lung cancer. Academic dissertation, Department of Oncology, Medical School, Tampere University Hospital, University of Tampere
3. De Baltas P, Bedos-Belval F (2011) Cinnamic acid derivatives as anticancer agents - a review. Curr Med Chem 18:1672-1703
4. Diplock AT, Charleux JL, Crozier-Willi G, Kok FJ, Rice-Evans C, Roberfroid M, Stahl W, Vina-Ribes J (1998) Functional food science and defence against reactive oxidative species. Br J Nutr 80:77-112
5. Fana Q, Jiang H, Yuana E-D, Zhang J-X, Ning Z-X, Qia S-J, Weia Q-Y (2012) Inhibitory effects on mushroom tyrosinase by cinnamoyl amino acid ester derivatives and their antioxidative activities. Food Chem 134:1081-1087
6. Frankel EN (2001) Interfacial lipid oxidation and antioxidation. J Oleo Sci 50:387-391
7. Friedman M (1996) Food browning and its prevention: an overview. J Agric Food Chem 44:631-653
8. Fu J, Cheng K, Zhang ZM, Fang RQ, Zhu HI (2010) Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials. Eur J Med Chem 45:2638-2643
9. Georgiev L, Totseva I, Seizova K, Marinova E, Chochkova M, Milkova Ts (2010) Antioxidant potential of phenolic acid amides of aromatic amines. In: Lebl M, Meldal M, Jensen K, Hoeg-Jensen T (eds) Peptides: Proceedings of the 31st Eur Pept Symp 60-61
10. Georgiev L, Chochkova M, Ivanova G, Najdenski H, Ninova M, Milkova T (2012) Radical scavenging and antimicrobial activities of cinnamoyl amides of biogenic monoamines. Riv Ital Sost Grasse 89:91-102
11. Heijnen CG, Haenen GR, Vekemans JA, Bast A (2001) Peroxynitrite scavenging of flavonoids: structure activity relationship. Environ Toxicol Pharmacol 10:199-206
12. Hindler J (1992) Clinical microbiology procedures handbook. American Society of Microbiology, Washington, DC
13. Hollman PCH (2001) Evidence for health benefits of plant phenols: local or systemic effects? J Sci Food Agric 81:842-852
14. Kim HJ, Seo SH, Lee BG, Lee YS (2005) Identification of tyrosinase inhibitors from Glycyrrhiza uralensis. Planta Med 71:785-787
15. Kwak SY, Seo HS, Lee YS (2009) Synergistic antioxidative activities of hydroxycinnamoyl-peptides. J Pept Sci 15:634-641
16. Kwak SY, Lee S, Choi HR, Park KC, Lee YS (2011) Dual effects of caffeoyl-amino acidyl-hydroxamic acid as an antioxidant and depigmenting agent. Bioorg Med Chem Lett 21:5155-5158
17. Kwak SY, Lee S, Yang JK, Lee YS (2012) Antioxidative activities of caffeoyl-proline dipeptides. Food Chem 130:847-852
18. Masamoto Y, Murata Y, Baba K, Shimoishi Y, Tada M, Takahata K (2004) Inhibitory effects of esculetin on melanin biosynthesis. Biol Pharm Bull 27:422-425
19. Matsuda H, Higashino M, Chen W, Tosa H, Iinuma M, Kubo M (1995) Studies of cuticle drugs from natural sources. III. Inhibitory effect of Myrica rubra on melanin biosynthesis. Biol Pharm Bull 18:1148-1150
20. Mosher DB, Pathak MA, Fitzpatrick TB (1983) In: Fitzpatrick TB, Eisen AZ, Wolff K, Freedberg IM, Austen KF (eds) Update: Dermatology in general medicine. McGraw-Hill, New York, pp 205-225
21. Narsimhan B, Belsare D, Pharande D, Mourya V, Dhake A (2004) Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations. Eur J Med Chem 39:827-834
22. •) tests. JAOCS 79:1191-1195
23. Noh JM, Lee YS (2011) Inhibitory activities of hydroxyphenolic acid-amino acid conjugates on tyrosinase. Food Chem 125:953-957
24. Noh JM, Kwak SY, Seo HS, Lee YS (2009) Kojic acid-amino acid conjugates as tyrosinase inhibitors. Bioorg Med Chem Lett 19:5586-5589
25. Ohshima H, Yoshie Y, Auriol S, Gilibert I (1998) Antioxidant and pro-oxidant actions of flavonoids: effects on DNA damage induced by nitric oxide, peroxynitrite and nitroxyl anion. Free Radic Biol Med 25:1057-1065
26. Parvez S, Kang M, Chung HS, Bae H (2007) Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries. Phytother Res 21:805-816
27. Qiu L, Chen QH, Zhuang JX, Zhong X, Zhou JJ, Guo YJ et al (2009) Inhibitory effects of a-cyano-4-hydroxycinnamic acid on the activity of mushroom tyrosinase. Food Chem 112:609-613
28. Seo HS, Kwak SY, Lee YS (2010) Antioxidative activities of histidine containing caffeic acid-dipeptides. Bioorg Med Chem Lett 20:4266-4272
29. Son S, Lewis BA (2002) Free radical scavenging and antioxidative activity of caffeic acid amide and ester analogues: structure-activity relationship. J Agric Food Chem 50:468-472
30. Spasova M, Kortenska-Kancheva V, Totseva I, Ivanova G, Georgiev L, Milkova T (2006) Synthesis of cinnamoyl and hydroxycinnamoyl amino acid conjugates and evaluation of their antioxidant activity. J Pept Sci 12:369-375
31. Stetinová V, Smetanová L, Grossmann V, Anzenbacher-Gen P (2002) In vitro and in vivo assessment of the antioxidant activity of melatonin and related indole derivatives. Physiol Biophys 21:153-162
32. Wei Q-Y, Jiang H, Zhang J-X, Guo P-F, Wang H (2012a) Synthesis of N-hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities. Med Chem Res 21:1905-1911
33. Wei Q-Y, Jiang H, Zhang J-X, Zhang C, Guo P-F (2012b) The antimicrobial activities of the cinnamoyl amide of amino acid derivatives. Asian J Chem 24:2383-2388
34. Yanishlieva N, Popov A, Marinova E (1978) Eine modifizierte jodometrische Methode zur Bestimmung der Peroxidzahl in kleinen Lipidproben. C R Acad Sci Bulg 31:869-871