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Research Article

Inhibitory effects on mushroom tyrosinase by flavones from the stem barks of Morus lhou (S.) Koidz

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Pages 922-930 | Received 14 Jul 2007, Accepted 19 Sep 2007, Published online: 20 Oct 2008

References

  • B Fu, H Li, X Wang, FSC Lee, and S Cui. (2005). Isolation and identification of flavonoids in licorice and a study of their inhibitory effects on tyrosinase. J Agric Food Chem 53:7408–7414.
  • K Maeda, and MJ Fukuda. (1991). In vitro effectiveness of several whitening cosmetic components in human melanocytes. Soc Cosmet Chem 42:361–368.
  • JA Mcevily, R Iyengar, and QS Otwell. (1992). Inhibition of enzymatic browning in food and beverages. Crit Rev Food Sci Nutr 32:253–273.
  • QX Chen, KK Song, L Qiu, XD Liu, H Huang, and HY Guo. (2005). Inhibitory effects on mushroom tyrosinase by p-alkoxybenzoic acids. Food Chem 91:269–274.
  • SM Son, KD Moon, and CY Lee. (2000). Kinetic study of oxalic acid inhibition on enzymatic browning. J Agric Food Chem 48:2071–2074.
  • L Yu. (2003). Inhibitory effects of (S)- and (R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acids on tyrosinase activity. J Agric Food Chem 51:2344–2347.
  • S Khatib, O Nerya, R Musa, M Shmuel, S Tamir, and J Vaya. (2005). Chalcones as potent tyrosinase inhibitors: The importance of a 2,4-substituted resorcinol moiety. Bioorg Med Chem 13:433–441.
  • I Kubo, and KH Ikuyo. (1999). Flavonols from saffron flower: Tyrosinase inhibitory activity and inhibition mechanism. J Agric Food Chem 47:4121–4125.
  • M Jimenez, and F Garcia-Carmona. (1997). 4-Substituted resorcinols (sulfite alternatives) as slow-binging inhibitors of tyrosinase catecholase activity. J Agric Food Chem 45:2061–2065.
  • B Gasowska, B Frąckowiak, and H Wojtasek. (2006). Indirect oxidation of amino acid phenylhydrazides by mushroom tyrosinase. Biochim Biophys Acta 1760:1373–1379.
  • HS Lee. (2002). Tyrosinase inhibitors of Pulsatilla ceunua root-derived materials. J Agric Food Chem 50:1400–1403.
  • S Halaouli, M Asther, JC Sigoillot, M Hamdi, and A Lomascolo. (2006). Fungal tyrosinases: New prospects in molecular characteristics, bioengineering and biotechnological applications. J Appl Microbiol 100 (2):219–232.
  • AM Mayer. (2006). Polyphenol oxidases in plants and fungi: Going places? A review. Phytochemistry 67 (21):2318–2331.
  • LG Fenoll, MJ Penalver, JN Rodriguez-Lopez, R Varon, F Garcia-Canovas, and J Tudela. (2004). Tyrosinase kinetics: Discrimination between two models to explain the oxidation mechanism of monophenol and diphenol substrates. Int J Biochem Cell Biol 36:235–246.
  • MJ Penalver, LG Fenoll, JN Rodriguez-Lopez, PA Garcia-Ruiz, F Garcia-Molina, R Varon, and et al (2005). Reaction mechanism to explain the high kinetic autoactivation of tyrosinase. J Mol Catal B-Enzym 33 (1–2):35–42.
  • F Garcia-Molina, MJ Penalver, LG Fenoll, JN Rodriguez-Lopez, R Varon, F Garcia-Canovas, and et al (2005). Kinetic study of monophenol and o-diphenol binding to oxytyrosinase. J Mol Catal B-Enzym 32 (5–6):185–192.
  • KI Nihei, and I Kubo. (2003). Identification of oxidation product of arbutin in mushroom tyrosinase assay system. Bioorg Med Chem Lett 13:2409–2412.
  • I Kubo, and KH Ikuyo. (1998). Tyrosinase inhibitors form anise oil. J Agric Food Chem 46:1268–1271.
  • JA Mercedes, E Josefa, C Juana, GH Fernando, and GC Francisco. (2005). Oxidation of the flavonoid eriodictyol by tyrosinase. Plant Physiol Biochem 43:866–873.
  • I Kubo, KI Nihei, and K Shimizu. (2004). Oxidation products of quercetin catalyzed by mushroom tyrosinase. Bioorg Med Chem 12:5343–5347.
  • R Matsuura, H Ukeda, and M Sawamura. (2006). Tyrosinase inhibitory activity of citrus essential oils. J Agric Food Chem 54:2309–2313.
  • I Kubo, and KH Ikuyo. (1998). Tyrosinase inhibitors from cumin. J Agric Food Chem 46:5338–5341.
  • L Pourcel, JM Routaboul, V Cheynier, L Lepiniec, and I Debeaujon. (2007). Flavonoid oxidation in plants: From biochemical properties to physiological functions. Trends Plant Sci 12 (1):29–36.
  • LG Fenoll, PA Garcia-Ruiz, R Varon, and F Garcia-Canovas. (2003). Kinetic study of the oxidation of quercetin by mushroom tyrosinase. J Agric Food Chem 51 (26):7781–7787.
  • D Kim, J Park, J Kim, C Han, J Yoon, N Kim, and et al (2006). Flavonoids as mushroom tyrosinase inhibitors: A fluorescence quenching study. J Agric Food Chem 54 (3):935–941.
  • H Gao, J Nishida, S Saito, and J Kawabata. (2007). Inhibitory effects of 5,6,7-trihydroxyflavones on tyrosinase. Molecules 12 (1):86–97.
  • N Jun, G Hong, and K Jun. (2007). Synthesis and evaluation of 2,4′,6′-trihydroxychalcones as a new class of tyrosinase inhibitors. Bioorgan Med Chem 15 (6):2396–2402.
  • O Nerya, J Vaya, R Musa, S Izrael, BA Ruth, and S Tamir. (2003). Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots. J Agric Food Chem 51:1201–1207.
  • B Fu, H Li, X Wang, SCL Frank, and S Cui. (2005). Isolation and identification of flavonoids in licorice and a study of their inhibitory effects tyrosinase. J Agric Food Chem 53:7408–7414.
  • CH Jeong, and HS Ki. (2004). Tyrosinase inhibitor isolated from the leaves of Zanthoxylum piperitum. Biosci Biotechnol Biochem 68:1984–1987.
  • T Nomura. (2001). Chemistry and biosynthesis of prenylflavonoids. Yakugaku Zasshi-J Pharm Soc Japan 121 (7):535–556.
  • NK Lee, KH Son, HW Chang, SS Kang, H Park, MY Heo, and et al (2004). Prenylated flavonoids as tyrosinase inhibitors. Arch Pharm Res 27 (11):1132–1135.
  • ET Arung, K Shimizu, and R Kondo. (2006). Inhibitory effect of isoprenoid-substituted flavonoids isolated from Artocarpus heterophyllus on melanin biosynthesis. Planta Medica 72 (9):847–850.
  • T Nomura, T Fukia, S Yamada, and M Katayanagi. (1976). Phenolic constituents of the cultivated mulberry tree (Morus alba L.). Chem Pharm Bull 24:2898–2900.
  • S Yoshizawa, M Suganuma, H Fujiki, T Fukai, T Nomura, and T Sugimura. (1989). Morusin. isolated from root bark of Morus alba L., inhibits tumor promotion of teleocidin. Phytother Res 5:193–195.
  • KM Park, JS You, HY Lee, NI Baek, and JK Hwang. (2003). Kuwanon G: An antibacterial agent from the root bark of Morus alba against oral pathogens. J Ethnopharmacol 84:181–185.
  • Q Chu, M Lin, X Tian, and J Ye. (2006). Study on capillary electrophoresis-amperometric detection profiles of different parts of Morus alba (L). J Chromatogr A 1116:286–290.
  • WY Jin, MK Na, RB An, HY Lee, KH Bae, and SS Kang. (2002). Antioxidant compounds from twig of Morus alba. Nat Prod Sci 8:129–132.
  • SA Achmad, NA Emilo, L Ghisalberti, EH Hakim, M Kitajima, L Makmur, and et al (2004). Molecular diversity and biological activity of natural products from Indonesian moraceous plants. J Chem Soc Pakistan 26 (3):316–321.
  • ET Arung, IW Kusuma, YM Iskandar, S Yasutake, K Shimizu, and R Kondo. (2005). Screening of Indonesian plants for tyrosinase inhibitory activity. J Wood Sci 51 (5):520–525.
  • TH Kang, HR Oh, SM Jung, JH Ryu, MW Park, YK Park, and SY Kim. (2006). Enhancement of neuroprotection of mulberry leaves (Morus alba L.) prepared by the anaerobic treatment against ischemic damage. Biol Pharm Bull 29:270–274.
  • ANB Singab, HA El-Beshbishy, M Yonekawa, T Nomura, and T Fukai. (2005). Hypoglycemic effect of egyptian Morus alba root bark extract: Effect on diabetes and lipid peroxidation of streptozotocin-induced diabetic rats. J Ethnopharmacol 100:333–338.
  • T Nomura, T Fukai, and T Narita. (1980). Hypotensive constituent, kuwanon H, a new flavone derivative from the root bark of the cultivated mulberry tree (Morus alba L.). Heterocycles 14:1943–1951.
  • HY Sohn, KH Son, CS Kwon, GS Kwon, and SS Kang. (2004). Antimicrobial and cytotoxic activity of 18 prenylated flavonoids isolated from medicinal plants: Morus alba L., Morus mongolica Schneider, Broussnetia papyrifera (L.) Vent, Sophora flavescens Ait and Echinosophora koreensis Nakai. Phytomedicine 11:666–672.
  • J Du, ZD He, RW Jiang, WC Ye, HX Xu, and PPH But. (2003). Antiviral flavonoids from the root bark of Morus alba L. Phytochemistry 62 (8):1235–1238.
  • T Fukai, K Satoh, T Nomura, and H Sakagami. (2003). Antinephritis and radical scavenging activity of prenylflavonoids. Fitoterapia 74 (7–8):720–724.
  • BL Wei, JR Weng, PH Chiu, CF Hung, JP Wang, and CN Lin. (2005). Antiinflammatory flavonoids from Artocarpus heterophyllus and Artocarpus communis. J Agric Food Chem 53 (10):3867–3871.
  • T Nomura, T Fukai, and M Katayanagi. (1978). Studies on the constituents of the cultived mulberry tree. III. Isolation of four new flavones, kuwanon A, B, C, and oxydihydromorusin from the root bark Morus alba L. Chem Pharm Bull 26:1453–1458.
  • CN Lin, CM Lu, and PL Huang. (1995). Flavonoids from Artocarpus heterophyllus. Phytochemistry 39:1447–1451.
  • L Kittisak, S Boonchoo, and DE Wanchai. (2000). Tyrosinase inhibitors from Artocarpus gomezianus. Planta Med 66:275–277.
  • TJ Ha, S Tamura, and I Kubo. (2005). Effects of mushroom tyrosinase on anisaldehyde. J Agric Food Chem 53:7024–7028.
  • RA Copeland. Enzyme: A practical introduction to structure, mechanism, and data analysis. Wiley-VCH, New York, (2000) 266–332.
  • C Frieden. (1970). Kinetic aspects of regulation of metabolic processes. The hysteretic enzyme concept. J Biol Chem 245:5578–5799.
  • JF Morrison, and CT Walsh. (1988). The behavior and significance of slow-binding enzyme inhibitors. Adv Enzymol 61:201–301.
  • MJ Sculley, JF Morrison, and WW Cleland. (1996). Slow-binding inhibition: The general case. Biochimi Biophys Acta-Protein Struct Mol Enzymol 1298 (1):78–86.

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