Chemical composition and tyrosinase inhibitory activity of Cinnamomum cassia essential oil

Chen-Tien Chang, Wen-Lun Chang, Jaw-Cherng Hsu, Ying Shih, Su-Tze Chou, Chen-Tien Chang, Wen-Lun Chang, Jaw-Cherng Hsu, Ying Shih, Su-Tze Chou

Abstract

Background: Essential oils extracted from aromatic plants exhibit important biological activities and have become increasingly important for scientific research. The essential oil extracted from Cinnamomum cassia Presl (CC-EO) has various functional properties, however, little information is available regarding the tyrosinase inhibitory activity. Therefore, the objectives of this study were to investigate the chemical composition and tyrosinase inhibitory activity of the CC-EO.

Results: cis-2-methoxycinnamic acid (43.06%) and cinnamaldehyde (42.37%) were found to be the two major components of the CC-EO identified by gas chromatography-mass spectrometry (GC-MS). The inhibitory activities of CC-EO and its major constituents were further evaluated against mushroom tyrosinase. The results showed that CC-EO and cinnamaldehyde exhibited anti-tyrosinase activities with IC50 values of 6.16 ± 0.04 mg/mL and 4.04 ± 0.08 mg/mL, respectively. However, cis-2-methoxycinnamic acid did not show any anti-tyrosinase activity. The inhibition kinetics were analyzed by Lineweaver-Burk plots and second replots, which revealed that CC-EO and cinnamaldehyde were mixed-type inhibitors. The inhibition constants (Ki) for CC-EO and cinnamaldehyde were calculated to be 4.71 ± 0.09 mg/mL and 2.38 ± 0.09 mg/mL, respectively.

Conclusion: These results demonstrate that CC-EO and its major component, cinnamaldehyde, possess potent anti-tyrosinase activities and may be a good source for skin-whitening agents.

Keywords: Cinnamaldehyde; Cinnamomum cassia Presl; Mixed-type inhibition; Mushroom tyrosinase; Tyrosinase inhibitor.

Figures

Figure 1
Figure 1
Dose-dependent inhibition of mushroom tyrosinase byC. cassiaessential oil (CC-EO),trans-cinnamaldehyde and kojic acid. Tyrosinase activity was measured using L-DOPA as the substrate. Each value represents means ± S.D. (n = 3).
Figure 2
Figure 2
Determination of inhibition type and inhibition constants ofC. cassiaessential oil. (A) Lineweaver-Burk plots of mushroom tyrosinase and L-DOPA without (●) and with [(○) 1.56 mg/mL, (▼) 3.12 mg/mL, (△) 6.25 mg/mL and (■) 12.50 mg/mL] essential oil from C. cassia. (B) and (C) represent expressions of Ki and αKi, respectively.
Figure 3
Figure 3
Determination of inhibition type and inhibition constants oftrans-cinnamaldehyde. (A) Lineweaver-Burk plots of mushroom tyrosinase and L-DOPA without (●) and with [(○) 0.78 mg/mL, (▼) 1.56 mg/mL, (△) 3.12 mg/mL and (■) 6.25 mg/mL] trans-cinnamaldehyde. (B) and (C) represent expressions of Ki and αKi, respectively.

References

    1. Asanuma M, Miyazaki I, Ogawa N. Dopamine- or L-DOPA-induced neurotoxicity: the role of dopamine quinone formation and tyrosinase in a model of Parkinson’s disease. Neurotox Res. 2003;5:165–176. doi: 10.1007/BF03033137.
    1. Chen JS, Wei CI, Marshall MR. Inhibition mechanism of kojic acid on polyphenol oxidase. J Agric Food Chem. 1991;39:1897–1901. doi: 10.1021/jf00011a001.
    1. Chen JS, Wei C, Rolle RS, Otwell WS, Balaban MO, Marshall MR. Inhibitory effect of kojic acid on some plant and crustacean polyphenol oxidases. J Agric Food Chem. 1991;39:1396–1401. doi: 10.1021/jf00008a008.
    1. Chen QX, Kubo I. Kinetics of mushroom tyrosinase inhibition by quercetin. J Agric Food Chem. 2002;50:4108–4112. doi: 10.1021/jf011378z.
    1. Chiari ME, Vera DM, Palacios SM, Carpinella MC. Tyrosinase inhibitory activity of a 6-isoprenoid-substituted flavanone isolated from Dalea elegans. Bioorg Med Chem. 2011;19:3474–3482. doi: 10.1016/j.bmc.2011.04.025.
    1. Choi J, Lee KT, Ka H, Jung WT, Jung HJ, Park HJ. Constituents of the essential oil of the Cinnamomum cassia stem bark and the biological properties. Arch Pharm Res. 2001;24:418–423. doi: 10.1007/BF02975187.
    1. Dooley T. Topical skin depigmentation agents. J Dermatolog Treat. 1997;8:275–283. doi: 10.3109/09546639709160535.
    1. Dugoua JJ, Seely D, Perri D, Cooley K, Forelli T, Mills E, Koren G. From type 2 diabetes to antioxidant activity: a systematic review of the safety and efficacy of common and cassia cinnamon bark. Can J Physiol Pharmacol. 2007;85:837–847. doi: 10.1139/Y07-080.
    1. Fiocco D, Fiorentino D, Frabboni L, Benvenuti S, Orlandini G, Pellati F, Gallone A. Lavender and peppermint essential oils as effective mushroom tyrosinase inhibitors: a basic study. Flavour Fragr J. 2011;26:441–446. doi: 10.1002/ffj.2072.
    1. Fitzpatrick TB, Eisen AZ, Wolff K, Freedberg IM, Austen KF. Updates: dermatology in general medicine. In: Mosher DB, Pathak MA, Fitzpatrick TB, editors. Vitiligo: ethology, pathogenesis, diagnosis and treatment. New York: Mcgraw-Hill; 1983.
    1. Friedman M. Food browning and its prevention: an overview. J Agric Food Chem. 1996;44:631–653. doi: 10.1021/jf950394r.
    1. Giordani R, Regli P, Kaloustian J, Portugal H. Potentiation of antifungal activity of amphotericin B by essential oil from Cinnamomum cassia. Phytother Res. 2006;20:58–61. doi: 10.1002/ptr.1803.
    1. Ka H, Park HJ, Jung HJ, Choi JW, Cho KS, Ha J, Lee KT. Cinnamaldehyde induces apoptosis by ROS-mediated mitochondrial permeability transition in human promyelocytic leukemia HL-60 cells. Cancer Lett. 2003;196:143–152. doi: 10.1016/S0304-3835(03)00238-6.
    1. Kim YJ, Uyama H. Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci. 2005;62:1707–1723. doi: 10.1007/s00018-005-5054-y.
    1. Koh WS, Yoon SY, Kwon BM, Jeong TC, Nam KS, Han MY. Cinnamaldehyde inhibits lymphocyte proliferation and modulates T-cell differentiation. Int J Immunopharmacol. 1998;20:643–660. doi: 10.1016/S0192-0561(98)00064-2.
    1. Kubo I, Kinst-Hori I. Tyrosinase inhibitors from anise oil. J Agric Food Chem. 1998;46:1268–1271. doi: 10.1021/jf9708958.
    1. Kubo I, Kinst-Hori I. Tyrosinase inhibitory activity of the olive oil flavor compounds. J Agric Food Chem. 1999;47:4574–4578. doi: 10.1021/jf990165v.
    1. Lee HS. Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. J Agric Food Chem. 2002;50:1400–1403. doi: 10.1021/jf011230f.
    1. Lee HS, Ahn YJ. Growth-inhibiting effects of Cinnamomum cassia bark-derived materials on human intestinal bacteria. J Agric Food Chem. 1998;46:8–12. doi: 10.1021/jf970548y.
    1. Lee HS, Kim BS, Kim MK. Suppression effect of Cinnamomum cassia bark-derived component on nitric oxide synthase. J Agric Food Chem. 2002;50:7700–7703. doi: 10.1021/jf020751f.
    1. Lee SE, Kim MK, Lee SG, Ahn YJ, Lee HS. Inhibitory effects of Cinnamomum cassia bark-derived materials on mushroom tyrosinase. Food Sci Biotechnol. 2000;9:330–333.
    1. Marongiu B, Piras A, Porcedda S, Tuveri E, Sanjust E, Meli M, Sollai F, Zucca P, Rescigno A. Supercritical CO2 extract of Cinnamomum zeylanicum: chemical characterization and antityrosinase activity. J Agric Food Chem. 2007;55:10022–10027. doi: 10.1021/jf071938f.
    1. Matsuura R, Ukeda H, Sawamura M. Tyrosinase inhibitory activity of citrus essential oils. J Agric Food Chem. 2006;54:2309–2313. doi: 10.1021/jf051682i.
    1. Ngoc TM, Lee I, Ha DT, Kim H, Min B, Bae K. Tyrosinase-inhibitory constituents from the twigs of Cinnamomum cassia. J Nat Prod. 2009;72:1205–1208. doi: 10.1021/np900031q.
    1. Ooi LS, Li Y, Kam SL, Wang H, Wong EY, Ooi VE. Antimicrobial activities of cinnamon oil and cinnamaldehyde from the Chinese medicinal herb Cinnamomum cassia Blume. Am J Chin Med. 2006;34:511–522. doi: 10.1142/S0192415X06004041.
    1. Sánchez-Ferrer A, Rodríguez-López JN, García-Cánovas F, García-Carmona F. Tyrosinase: a comprehensive review of its mechanism. Biochim Biophys Acta. 1995;1247:1–11. doi: 10.1016/0167-4838(94)00204-T.
    1. Segel IH. Biochemical calculations. 2. New York: John Wiley & Sons; 1976.
    1. Seo SY, Sharma VK, Sharma N. Mushroom tyrosinase: recent prospects. J Agric Food Chem. 2003;51:2837–2853. doi: 10.1021/jf020826f.
    1. Shaughnessy DT, Setzer RW, DeMarini DM. The antimutagenic effect of vanillin and cinnamaldehyde on spontaneous mutation in Salmonella TA104 is due to a reduction in mutations at GC but not AT sites. Mutat Res. 2001;480–481:55–69. doi: 10.1016/S0027-5107(01)00169-5.
    1. Verspohl EJ, Bauer K, Neddermann E. Antidiabetic effect of Cinnamomum cassia and Cinnamomum zeylanicum in vivo and in vitro. Phytother Res. 2005;19:203–206. doi: 10.1002/ptr.1643.
    1. Webb JL. Enzyme and metabolic inhibitors. New York: Academic Press; 1963.
    1. Zhao X, Zhu JX, Mo SF, Pan Y, Kong LD. Effects of cassia oil on serum and hepatic uric acid levels in oxonate-induced mice and xanthine dehydrogenase and xanthine oxidase activities in mouse liver. J Ethnopharmacol. 2006;103:357–365. doi: 10.1016/j.jep.2005.08.040.

Source: PubMed

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