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Phenolic constituents of Nelumbinis Semen and Their Tyrosinase Inhibitory Activity  

Jeong, Ji Yeon (College of Pharmacy, Chungbuk National University)
Mo, Eun Jin (College of Pharmacy, Chungbuk National University)
Hwang, Bang Yeon (College of Pharmacy, Chungbuk National University)
Lee, Mi Kyeong (College of Pharmacy, Chungbuk National University)
Publication Information
Korean Journal of Pharmacognosy / v.46, no.1, 2015 , pp. 1-5 More about this Journal
Abstract
In the course of screening tyrosinase inhibitory activity, EtOAc-soluble fraction of Nelumbinis Semen (Seeds of Nelumbo nucifera) showed significant inhibition. Further fractionation of the EtOAc-soluble fraction resulted in 12 compounds, which were identified as 4-(hydroxymethyl)phenol (1), tyrosol (2), 4-(hydroxymethyl)benzaldehyde (3), 4-hydroxybenzoic acid (4), 4-(2-methoxyvinyl)benzene-1,2-diol (5), 2,6-dihydroxybenzoic acid (6), (2R-trans)-2,3-dihydro-3,5,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (7), (+)-catechin (8), elephantorrhizol (9), (+)-dehydrovomifoliol (10), (-)-boscialin (11) and uridine (12). Compounds 5 and 7 were first reported from this plant. Among the isolated compounds, compound 7 showed strong inhibition on tyrosinase activity with mixed mechanism of competitive and noncompetitive inhibition.
Keywords
Nelumbinis Semen; Tyrosinase; Phenolic compounds;
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1 Mayo, F., Gashe, B. A. and Majinda, R. R. T. (1999) A new flavan from Elephantorrhiza goetzei. Fitoterapia 70: 412-416.   DOI
2 Wattanapiromsakul, C., Forsterc, P. I. and Waterman, P. G. (2003) Alkaloids and limonoids from Bouchardatia neurococca: systematic significance. Phytochemistry 64: 609-615   DOI
3 Yalcin, F. N., Ersoz, T., Akbay, P. and Calis, I. (2003) Phenolic, megastigmane, nucleotide, acetophenon and monoterpene glycosides from Phlomis samia and P. carica. Turk. J. Chem. 27: 703-711.
4 Zheng, Z., Tan, H., Chen, J. and Wang, M. (2013) Characterization of tyrosinase inhibitors in the twigs of Cudrania tricuspidata and their structure-activity relationship study. Fitoterapia 84: 242-247.   DOI   ScienceOn
5 Hasnah, M. S., Mohd, F. R. and Zanariah, U. (2010) Isolation and identification of radical scavenging and tyrosinase inhibition of polyphenols from Tibouchina semidecandra L. J. Agric. Food. Chem. 58: 10404-10409.   DOI
6 Husam, M. K., Dihui, H., Bijun, X., Hui, H., Erning, Y., Binqiang, T. and Di, X. (2010) Flavonols of lotus (Nelumbo nucifera, Gaertn.) seed epicarp and their antioxidant potential. Eur. Food Res. Technol. 23: 387-394.
7 Parvez, S., Kang, M., Chung, H. W. and Bae, H. (2007) Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries. Phytother. Res. 21: 805-816.   DOI
8 배기환 (2000) 한국의 약용식물, 교학사, 서울
9 Wattanapiromsakul, C., Forsterc, P. I. and Waterman, P. G. (2003) Alkaloids and limonoids from Bouchardatia neurococca: systematic significance. Phytochemistry 64: 609-615.   DOI
10 Lee, J. Y., Im, K. R., Jung, T. K. and Yoon, K. S. (2013) The inhibitory effects of Nelumbo nucifera Gaertner extract on melanogenesis. Kor. Soc. Biotechnol. Bioeng. J. 28: 137-145.
11 Thomas, H. F., Ping, C., Cindy, G. U. and Anthony, J. D. (1995) One-and two-dimensional NMR study of resol phenol-formaldehyde prepolymer resins. Magn. Reson. Chem. 33: 717-723.   DOI
12 Yoshiaki, T., Tadashi, F., Shunsuke, M., Takashi, A., Yoshihiro, H., Naohisa, I. and Masatake, N. (2007) Antoxidant constituents in distillation residue of Awamori spirits. J. Agric. Food. Chem. 55: 75-79.   DOI
13 Fox, M. E., Jackson, M., Meek, G. and Willets, M. (2011) Large-scale synthesis of a substitued D-phenylalanine using asymmetric hydrogenation. Org. Process Res. Dev. 15: 1163-1171.   DOI
14 Rukachaisirikul, V., Khamthong, N., Sukpondma, Y., Phongpaichit, S., Hutadilok-Towatana, N., Graidist, P., Sakayaroj, J. and Kirtikara, K. (2010) Cyclohexene, diketopiperazine, lactone and phenol derivatives from the sea fan-derived fungi Nigrospora sp. PSU-F11 and PSU-F12. Arch. Pharm. Res. 33: 375-380.   DOI
15 Prota, G. (1988) Progress in the chemistry of melanins and related metabolites. Med. Res. Rev. 8: 525-556.   DOI
16 Seiberg, M., Paine, C., Sharlow, E., Andrade-Gordon, P., Costanzo, M., Eisinger, M. and Shapiro, S. S. (2000) Inhibition of melanosome transfer results in skin lightening. J. Invest. Dermatol. 115: 162-167.   DOI
17 Yamaguchi, Y., Brenner, M. and Hearing, V. J. (2007) The regulation of skin pigmentation. J. Biol. Chem. 282: 27557-27561.   DOI
18 Seo, S. Y., Sharma, V. K. and Sharma, N. (2003) Mushroom tyrosinase: recent prospects. J. Agric. Food Chem. 51: 2837-2853.   DOI
19 Friedman, M. (1996) Food browning and its prevention: an overview. J. Agric. Food Chem. 44: 631-653.   DOI
20 Mayer, A. M. (1987) Polyphenol oxidases in plant: recent progress. Phytochemistry 26: 11-20.   DOI
21 Chang, T. S. (2009) An updated review of tyrosinase inhibitors. Int. J. Mol. Sci. 10: 2440-2475.   DOI   ScienceOn
22 Kim, Y.-J. and Uyana, H. (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell. Mol. Life Sci. 62: 1707-1723.   DOI
23 Sugumaran, M. (1991) Molecular mechanisms mammalian melanogenesis comparison with insect culticular sclerotization. FEBS Lett. 293: 4-10.   DOI