Abstract
Mulberroside A, a glycosylated stilbene, was isolated and identified from the ethanol extract of the roots of Morus alba. Oxyresveratrol, the aglycone of mulberroside A, was produced by enzymatic hydrolysis of mulberroside A using the commercial enzyme Pectinex®. Mulberroside A and oxyresveratrol showed inhibitory activity against mushroom tyrosinase with an IC50 of 53.6 and 0.49 μM, respectively. The tyrosinase inhibitory activity of oxyresveratrol was thus approximately 110-fold higher than that of mulberroside A. Inhibition kinetics showed mulberroside A to be a competitive inhibitor of mushroom tyrosinase with l-tyrosine and l-DOPA as substrate. Oxyresveratrol showed mixed inhibition and noncompetitive inhibition against l-tyrosine and l-DOPA, respectively, as substrate. The results indicate that the tyrosinase inhibitory activity of mulberroside A was greatly enhanced by the bioconversion process.
References
Andrabi SA, Spina MG, Lorenz P, Ebmeyer U, Wolf G, Horn TF (2004) Oxyresveratrol (trans-2, 3′, 4, 5′-tetrahydroxystilbene) is neuroprotective and inhibits the apoptotic cell death in transient cerebral ischemia. Brain Res 1017:98–107
Bajpai VK, Kim HR, Hou CT, Kang SC (2009) Bioconverted products of essential fatty acids as potential antimicrobial agents. N Biotechnol 26:122–130
Chen JS, Wei C, Rolle RS, Otwell WS, Balaban MO, Marshall MR (1991) Inhibitory effect of kojic acid on some plant and crustacean polyphenol oxidases. J Agric Food Chem 39:1396–1401
Choi SY, Kim S, Kim H, Suk K, Hwang JS, Lee BG, Kim AJ, Kim SY (2002) (4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene as a potent inhibitor of melanin production. Chem Pharm Bull 50:450–452
Chung KO, Kim BY, Lee MH, Kim YR, Chung HY, Park JH, Moon JO (2003) In vitro and in vivo anti-inflammatory effect of oxyresveratrol from Morus alba L. J Pharm Pharmacol 55:1695–1700
El-Beshbishy HA, Singab ANB, Sinkkonen J, Pihlaja K (2006) Hypolipidemic and antioxidant effects of Morus alba L. (Egyptian mulberry) root bark fractions supplementation in cholesterol-fed rats. Life Sci 78:2724–2733
Feng X, Zhang L, Zhu H (2009) Comparative anticancer and antioxidant activities of different ingredients of Ginkgo biloba extract (EGb 761). Planta Med 75:792–796
Habauzit V, Nielsen IL, Gil-Izquierdo A, Trzeciakiewicz A, Morand C, Chee W, Barron D, Lebecque P, Davicco MJ, Williamson G, Offord E, Coxam V, Horcajada MN (2009) Increased bioavailability of hesperetin-7-glucoside compared with hesperidin results in more efficient prevention of bone loss in adult ovariectomised rats. Br J Nutr 102:976–984
Hirakura K, Fujimoto Y, Fukai T, Nomura T (1986) Two phenolic glycosides from the root bark of the cultivated Mulberry tree (Morus lhou). J Nat Prod 49:218–224
Kim DH, Kim JH, Baek SH, Seo JH, Kho YH, Oh TK, Lee CH (2004) Enhancement of tyrosinase inhibition of the extract of Veratrum patulum using cellulase. Biotechnol Bioeng 87:849–854
Kim YM, Yun J, Lee CK, Lee H, Min KR, Kim Y (2002) Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of action. J Biol Chem 277:16340–16344
Körner AM, Pawelek J (1982) Mammalian tyrosinase catalyzes three reactions in the biosynthesis of melanin. Science 217:1163–1165
Kubo I, Hori IK (1999) Flavonols from Saffron flower: tyrosinase inhibitory activity and inhibition mechanism. J Agric Food Chem 47:4121–4125
Li H, Cheng KW, Cho CH, He Z, Wang M (2007) Oxyresveratrol as an antibrowning agent cloudy apple juices and fresh-cut apples. J Agric Food Chem 55:2604–2610
Liederer BM, Borchardt RT (2006) Enzymes involved in the bioconversion of ester-based prodrugs. J Pharm Sci 95:1177–1195
Likhitwitayawuid K, Sornsute A, Sritularak B, Ploypradith P (2006) Chemical transformations of oxyresveratrol (trans-2, 4, 3′, 5′-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. Bioorg Med Chem Lett 16:5650–5653
Lorenz P, Roychowdhury S, Engelmann M, Wolf G, Horn TF (2003) Oxyresveratrol and resveratrol are potent antioxidants and free radical scavengers: effect on nitrosative and oxidative stress derived from microglial cells. Nitric Oxide 9:64–76
Marotti I, Bonetti A, Biavati B, Catizone P, Dinelli G (2007) Biotransformation of common bean (Phaseolus vulgaris L.) flavonoid glycosides by bifidobacterium species from human intestinal origin. J Agric Food Chem 55:3913–3919
Mayer AM (1987) Polyphenol oxidases in plants: recent progress. Phytochemistry 26:11–20
Morito K, Hirose T, Kinjo J, Hirakawa T, Okawa M, Nohara T, Ogawa S, Inoue S, Muramatsu M, Masamune Y (2001) Interaction of phytoestrogens with estrogen receptors alpha and beta. Biol Pharm Bull 24:351–356
Nielsen IL, Chee WS, Poulsen L, Offord-Cavin E, Rasmussen SE, Frederiksen H, Enslen M, Barron D, Horcajada MN, Williamson G (2006) Bioavailability is improved by enzymatic modification of the citrus flavonoid hesperidin in humans: a randomized, double-blind, crossover trial. J Nutr 136:404–408
Otieno DO, Shah NP (2007) A comparison of changes in the transformation of isoflavones in soymilk using varying concentrations of exogenous and probiotic-derived endogenous β-glucosidases. J Appl Microbiol 103:601–612
Pereira JA, Pereira AP, Ferreira IC, Valentão P, Andrade PB, Seabra R, Estevinho L, Bento A (2006) Table olives from Portugal: phenolic compounds, antioxidant potential, and antimicrobial activity. J Agric Food Chem 54:8425–8431
Qiu F, Komatsu K, Kawasaki K, Saito K, Yao X, Kano Y (1996) A novel stilbene glycoside, oxyresveratrol 3′-O-β-glucopyranoside, from the root bark of Morus alba. Planta Med 62:559–561
Rooseboom M, Commandeur JN, Vermeulen NP (2004) Enzyme-catalyzed activation of anticancer prodrugs. Parmacol Rev 56:53–102
Ryu SY, Han YN, Han BH (1988) Monoamine oxidase-A inhibitors from medicinal plants. Arch Pharm Res 11:230–239
Schweikardt T, Olivares C, Solano F, Jaenicke E, García-Borrón JC, Decker H (2007) A three-dimensional model of mammalian tyrosinase active site accounting for loss of function mutations. Pigment Cell Res 20:394–401
Shimizu K, Kondo R, Sakai K (2000) Inhibition of tyrosinase by flavonoids, stilbenes and related 4-substituted resorcinols: structure-activity investigations. Planta Med 66:11–15
Shin NH, Ryu SY, Choi EJ, Kang SH, Chang IM, Min KR, Kim Y (1998) Oxyresveratrol as the potent inhibitor on Dopa oxidase activity of mushroom tyrosinase. Biochem Biophys Res Commun 243:801–803
Tsuchihashi R, Kodera M, Sakamoto S, Nakajima Y, Yamazaki T, Niiho Y, Nohara T, Kinjo J (2009) Microbial transformation and bioactivation of isoflavones from Pueraria flowers by human intestinal bacterial strains. J Nat Med 63:254–260
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This study was supported by the Technology Development Program for Agriculture and Forestry, Ministry for Food, Agriculture, Forestry and Fisheries, Republic of Korea.
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Kim, JK., Kim, M., Cho, SG. et al. Biotransformation of mulberroside A from Morus alba results in enhancement of tyrosinase inhibition. J Ind Microbiol Biotechnol 37, 631–637 (2010). https://doi.org/10.1007/s10295-010-0722-9
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DOI: https://doi.org/10.1007/s10295-010-0722-9