Article
In conclusion, trans-cinnamaldehyde thiosemicarbazone could
J. Agric. Food Chem., Vol. 57, No. 12, 2009 5523
dehydes to human solid tumor cells. Arch. Pharm. Res. 1998, 21,
147–152.
10) Shaughnessy, D. T.; Setzer, R. W.; DeMarini, D. M. The anti-
mutagenic effect of vanillin and cinnamaldehyde on spontaneous
mutation at GC but not AT sites. Mutat. Res. 2001, 480-481,
inhibit both the monophenolase activity and diphenolase activity
of tyrosinase. Furthermore, we found that trans-cinnamaldehyde
thiosemicarbazone had bacteriostatic activity. All of these
data may provide the basis for developing novel tyrosinase
inhibitors and developing new potent food preservatives or
cosmetic additives.
(
55–69.
(
11) Lee, H. S. Tyrosinase inhibitors of Pulsatilla cernua root-derived
materials. J. Agric. Food Chem. 2002, 50 (6), 1400–1403.
(
12) Chen, Q. X.; Song, K. K.; Qiu, L.; Liu, X. D.; Huang, H.; Guo, H. Y.
Inhibitory effects on mushroom tyrosinase by p-alkoxybenzoic acids.
Food Chem. 2005, 91, 269–274.
ABBREVIATIONS USED
DMSO, dimethylsulfoxide;
lalanine; -Tyr, -tyrosine; IC , inhibitor concentrations leading
to 50% activity lost; MIC, minimum inhibitory concentration;
L-DOPA, L-3,4-dihydroxypheny-
(
13) Chen, Q. X.; Liu, X. D.; Huang, H. Inactivation kinetics of mush-
L
L
5
0
room tyrosinase in the dimethyl sulfoxide solution. Biochemistry
(Moscow) 2003, 68, 644–649.
MBC, minimum bactericidal concentration; v , initial velocity in
0
(14) Perez, C.; Pauli, M.; Bazerque, P. An antibiotic assay by the agar well
diffusion method. Acta Biol. Med. Exp. 1990, 15, 113–115.
(15) Owais, M.; Sharad, K. S.; Shehbaz, A.; Saleemuddin, M. Antibac-
terial efficacy of Withania somnifera (ashwagandha), an indigenous
medicinal plant against experimental murine salmonellosis. Phyto-
medicine 2005, 12, 229–235.
the absence of the inhibitor; v , initial velocity in the presence of
i
the inhibitor; K , equilibrium constant of the inhibitor combining
I
with the free enzyme; K , equilibrium constant of the inhibitor
IS
combining with the enzyme-substrate complex.
(
16) Kubo, I.; Fujita, K. I.; Kubo, A.; Nihei, K. I.; Ogura, T. Antibacter-
ial activity of coriander volatile compounds against Salmonella
choleraesuis. J. Agric. Food Chem. 2004, 52, 3329–3332.
LITERATURE CITED
(
1) Whitaker, J. R. Polyphenol Oxidase. In Food Enzymes, Structure and
Mechanism; Wong, D. W. S., Ed.; Chapman & Hall: New York,
(17) Han, P.; Chen, C. Q.; Zhang, C. L.; Song, K. K.; Zhou, H. T.; Chen,
Q. X. Inhibitory effects of 4-chlorosalicylic acid on mushroom
tyrosinase and its antimicrobial activities. Food Chem. 2008, 107,
797–803.
(18) Ley, J. P.; Bertram, H. J. Hydroxy- or methoxy-substituted benzal-
doximes and benzaldehyde-o-alkyloximes as tyrosinase inhibitors.
Bioorg. Med. Chem. 2001, 9, 1879–1885.
(19) Gong S. Z.; Yang, Z.; Cheng, J. Calculating method and verification
on IC50 value of tyrosinase inhibitor. China Sufactant Deterg.
Cosmet. 2007, 37 (3), 149-151; 155.
(20) Liu, J. B.; Yi, W.; Wan, Y. Q.; Ma, L.; Song, H. C. 1-(1-Arylethy-
lidene) thiosemicarbazide derivatives: A new class of tyrosinase
inhibitors. Bioorg. Med. Chem. 2008, 16, 1096–1102.
1
995; pp 271-307.
(
(
(
2) Friedman, M. Food browning and its prevention: an overview. J.
Agric. Food Chem. 1996, 44, 631–653.
3) Martinez, M. V.; Whitaker, J. R. The biochemistry and control of
enzymatic browning. Trends Food Sci. Technol. 1995, 6, 195–200.
4) Likhitwitayawuid, K.; Sritularak, B. A new dimeric stilbene with
tyrosinase inhibitory activity from Artocarpus gomezianus. J. Nat.
Prod. 2001, 64, 1457–1459.
(
5) Scotter, M. J.; Castle, L. Chemical interactions between additives in
foodstuffs: a review. Food Addit. Contam. 2004, 21, 93–124.
6) Chen, Q. X.; Song, K. K.; Wang, Q.; Huang, H. Inhibitory effects on
mushroom tyrosinase by some alkylbenzaldehydes. J. Enzyme Inhib.
Med. Chem. 2003, 15, 491–496.
(
(
7) Huang, H.; Liu, X. D.; Chen, Q. X. Studies on mushroom tyrosinase
activity inhibited by benzaldehyde family compounds. J. Xiamen
Univ. (Nature Sci.) 2003, 1, 97–101.
8) Xie, X. Y.; Jiang, L.; Xue, C. B.; Luo, W. C. Synthesis of substituted
benzaldehyde and its activity for inhibition of the phenoloxidase of
the diamondback moth Plutella xylostella (L.). Huaxue Shiji 2007, 29
Received March 5, 2009. Revised manuscript received May 8, 2009.
Accepted May 11, 2009. The present investigation was supported
by the National Key Technology R & D Program of China (No.
(
2
007BAD07B06), the National High Technology Research and
Development Program (“863” Program) of China (2006AA10211),
the Science and Technology Foundation of Fujian Province (No.
2007N0051), the Natural Science Foundation of China (No.
20832005) and the Postdoctoral Foundation of China (20080430787).
(1), 34–36.
(
9) Kwon, B. M.; Lee, S. H.; Choi, S. U.; Park, S. H.; Lee, C. O.;
Cho, Y. K. Synthesis and in vitro cytotoxicity of cinnamal-