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A Tyrosinase Inhibitor Isolated from the Seeds of Eriobotrya japonica  

Kim, Tae-Hoon (Department of Herbal Medicinal Pharmacology, Daegu Haany University)
Shin, Seung-Ryeul (Faculty of Herbal Food & Nutrition, Daegu Haany University)
Kim, Tae-Wan (Faculty of Food Science & Biotechnology, Andong National University)
Lee, In-Chul (Senior Industry Cluster Agency, Youngdong University)
Park, Moon-Young (Subtropical Fruit Crops Experiment Station, Jeonnam Agricultural Research & Extension Services)
Jo, Cheo-Run (Department of Animal Science and Biotechnology, Chungnam National University)
Publication Information
Food Science and Preservation / v.16, no.3, 2009 , pp. 435-441 More about this Journal
Abstract
Activity-guided isolation from the ethylacetate (EtOAc)-soluble portion of a methanolic extract of the seeds of Eriobotrya japonica, using several bioassays, led to the isolation and identification of six phenolic compounds of previously known structure: benzaldehyde (1), chlorogenic acid (2), caffeic acid (3), benzoic acid (4), ferulic acid (5), and amygdalin (6). Of these, benzaldehyde (1) exhibited tyrosinase inhibitory activity in a bioassay. In addition, chlorogenic acid (2) and caffeic acid (3) were found to have strong antioxidative effects on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and superoxide dismutase (SOD)-like activity.
Keywords
Eriobotrya japonica; tyrosinase inhibition; antioxidant; phenolic compounds;
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1 Young, H.S., Chung, H.Y., Lee, C.K., Park, K.Y., Yokozawa, T., Oura, H. (1994) Ursolic acid inhibits aflatoxin B1-induced mutagenicity in a Salmonella assay system. Biol. Pharm. Bull., 17, 990-992   DOI   PUBMED   ScienceOn
2 Ito, H., Kobayashi, E., Takamatsu, Y., Li, SH., Hatano, T., Sakagami, H., Kusama, K., Satoh, K., Sugita, D., Shimura, S., Itoh, Y., Yoshida, T. (2000) Polyphenols from Eriobotrya japonica and their cytotoxicity against human oral tumor cell lines. Chem. Pharm. Bull.. 48, 687-693   DOI   PUBMED   ScienceOn
3 Kawahara, N., Satake, M., Goda, Y. (2002) A new acylated flavonol glycoside from the leaves of Eriobotrya japonica. Chem. Pharm. Bull., 50, 1619-1620   DOI   ScienceOn
4 Yokota, J., Takuma, D., Hamada, A., Onogawa, M., Yoshioka, S., Kusunose, M., Miyamura, M., Kyotani, S., Nishioka, Y. (2008) Gastroprotective activity of Eriobotrya japonica seed extract on experimentally induced gastric lesions in rats. Nat. Med., 62, 96-100
5 Hearing, V.J., Jimenez, M. (1987) Mammalian tyrosinasethe critical regulatory control point in melanocyte pigmentation. Int. J. Biochem., 19, 1141-1147   DOI   ScienceOn
6 Maeda, K., Naitou, T., Umishio, K., Fukuhara, T., Motoyama, A. (2007) A novel melanin inhibitor: hydroperoxy traxastane-type triterpene from flowers of Arnica montana. Biol. Pharm. Bull. 30, 873-87   DOI   ScienceOn
7 Badria, F.A., elGayyar, M.A. (2001) A new type pf tyrosinase inhibitors from natural products as potential treatments for hyperpigmentation. Boll. Chim. Farm., 140, 267-71
8 Namba, T. (1994) The encyclopedia of Wakan-Yaku (Traditional Sinojapanese Medicines) with color pictures. Hoikusa, Osaka. Vol II., 80-82
9 Liang, Z.Z., Aquino, R., De Feo, V., De Simone, F.,Pizza, C. (1990) Polyhydroxylated Triterpenes from Eriobotrya japonica. Planta Medica, 56, 330-332   DOI   PUBMED   ScienceOn
10 De Tommasi N., De Simone F., Pizza, C., Mahmood, N., Moore, P.S., Conti, C., Orsi, N., Stein, M.L. (1992) Constituents of Eriobotrya japonica. A study of their antiviral properties. J. Nat. Prod., 55, 1067-1073   DOI   PUBMED
11 Ito, H., Kobayashi, E., Li, S.H., Hatano, T., Sugita, D., Kubo, N., Shimura, S., Itoh, Y., Yoshida, T. (2001) Megastigmane glycosides and an acylated triterpenoid from Eriobotrya japonica. J. Nat. Prod., 64, 737-740   DOI   ScienceOn
12 Prota, G. (1980) Recent advances in the chemistry of melanogenesis in mamals. J. Invest. Dermatol., 75, 122-127   DOI   ScienceOn
13 Kim, H.J., Jo, C.H., Kim, T.H., Kim, D.S., Park, M.Y., Byun, M.W. (2006) Biological evaluation of the methanolic extract of Eribotrya japonica and its irradiation effect. Korean J. Food. Sci. Technol., 38, 684-690
14 De Tommasi N., De Simone F., Pizza, C., Nahmood, N., Moore, P.S., Conti, C., Orsi, N., Stein, M.L. (1992) Constituents of Eriobotrya japonica. A study of their antiviral properties. J. Nat. Prod., 55, 1067-1073   DOI   PUBMED
15 Taniguchi, S., Imayoshi, Y., Kobayashi, E., Takamatsu, Y., Ito, H., Hatano, T., Sakagami, H., Tokuda, H., Nishino, H., Sugita, D., Shimura, S., Yoshida, T. (2002) Production of bioactive triterpenes by Eriobotrya japonica calli. Phytochem.. 59, 315-23   DOI   ScienceOn
16 Jung, H.A., Park, J.C., Chung, H.Y., Kim, J., Choi, J.S. (1999) Antioxidant flavonoids and chlorogenic acid from the leaves of Eriobotrya japonica. Arch. Pharm. Res., 22, 213-218   DOI   ScienceOn
17 Stefan, M., Gudrun, M. (1974) Involvement of the superoxide anion radical in the autooxidation of pyrogallol and a convenient assay for superoxide dismutase. Eur. J. Biochem., 47, 469-474   DOI   ScienceOn
18 De Tommasi N., De Simone F., Cirino, G, Cicala, C, Pizza, C. (1991) Hypoglycemic effects of sesquiterpene glycosides and polyhydroxylated triterpenoids of Eriobotrya japonica. Planta Medica, 57, 414-416   DOI   ScienceOn
19 Kwon, Y.S., Won, H.M., Kim, C.M. (2000) Flavonoids from Indigofera pseudo-tinctoria stem. Korean J. Pharmacogn., 31, 280-283
20 Andray, C., Wingernitz, F. (1982) Structures of Vervascoside and Orobanchoside, caffeic acid sugar esters from Orobanche Rapum-Genistate. Phytochem. 21, 1123-1127   DOI   ScienceOn
21 Pave,l S, Muskiet, F.A. (1983) Eumelanin (precursor) metabolites as markers for pigmented malignant melanoma: a preliminary report. Cancer Detect Prev., 6, 311-316   PUBMED
22 Shimizu, M., Fukumura, H., Tsuji, H., Tanaami, S., Hayashi, T., Morita, N. (1986) Anti-inflammatory constituents of topically applied crude drugs. I. Constituents and anti-inflammatory effect of Eriobotrya japonica LINDL. Chem. Pharm. Bull., 34, 2614-2617   DOI   PUBMED   ScienceOn
23 Ito, H., Kobayashi, E., Li, S.H., Hatano, T., Sugita, D., Kubo, N., Shimura, S., Itoh, Y., Tokuda, H., Nishino, H., Yoshida, T. (2002) Antitumor activity of compounds isolated from leaves of Eriobotrya japonica. J. Agric. Food. Chem., 50, 2400-2403   DOI   ScienceOn
24 Baek, Y.S., Ryu, Y.B., Curtis-Long, M.J., Ha, T.J., Rengasamy, R., Yang, M.S., Park, K.H. (2009) Tyrosinase inhibitory effects of 1,3-diphenylpropanes from broussonetia kazinoki. Bioorg. Med. Chem., 17, 35-41   DOI   ScienceOn
25 Kwon, H.J., Kang, M.J., Kim, H.J., Choi, J.S., Paik, K.J., Chung, H.Y. (2000) Inhibition of NF kappaB by methyl chlorogenate from Eriobotrya japonica. Mol. Cells, 10, 241-246   PUBMED
26 Seeram, N.P., Cichewicz, R.H., Chandra, A., Nair, M.G. (2003) Cyclooxygenase inhibitory and antioxidant compounds from crabapple fruits. J. Agric. Food Chem., 51, 1948-1951   DOI   ScienceOn
27 Tanaka. K., Nishizono, S., Makino, N., Tamaru, S., Terai, O., Ikeda, I. (2008) Hypoglycemic activity of Eriobotrya japonica seeds in type 2 diabetic rats and mice. Biosci. Biotechnol. Biochem., 72, 686-693   DOI   ScienceOn
28 Yokota, J., Takuma, D., Hamada, A,, Onogawa, M., Yoshioka, S., Kusunose, M., Miyamura, M., Kyotani, S., Nishioka, Y. (2006) Scavenging of reactive oxygen species by Eriobotrya japonica seed extract. Biol. Pharm. Bull., 29, 467-471   DOI   ScienceOn
29 Blois, M.S. (1958) Antioxidant activity determination by the use of a stable free radical. Nature, 181, 1199-1200   DOI   ScienceOn
30 Yagi, A., Kanbara, T., Morinobu, N. (1987) Inhibition of mushroom-tyrosinase by aloe extract. Planta Med., 53, 515-517   DOI   PUBMED   ScienceOn
31 Morishita, H., Iwahashi, H., Osaka, N., Kido, R. (1984) Chromatographic separation and identification of naturally occurring chlorogenic acids by 1H nuclear magnetic resonance spectroscopy and mass spectrometry. J. Chromatogr., 19, 253-60