Tyrosinase inhibitory effects of 1,3-diphenylpropanes from Broussonetia kazinoki.

Published on Jan 1, 2009in Bioorganic & Medicinal Chemistry3.641
· DOI :10.1016/J.BMC.2008.11.022
Tae Joung Ha12
Estimated H-index: 12
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Abstract
Abstract Six 1,3-diphenylpropanes exhibiting inhibitory activities against both the monophenolase and diphenolase actions of tyrosinase were isolated from the methanol (95%) extract of Broussonetia kazinoki . These compounds, 1 – 6, were identified as kazinol C ( 1 ), D ( 2 ), F ( 3 ), broussonin C ( 4 ), kazinol S ( 5 ) and kazinol T ( 6 ). The latter two species ( 5 and 6 ) emerged to be new 1,3-diphenylpropanes which we fully spectroscopically characterized. The IC 50 values of compounds ( 1 , 3 – 5 ) for monophenolase inhibition were determined to range between 0.43 and 17.9 μM. Compounds 1 and 3 – 5 also inhibited diphenolase significantly with IC 50 values of 22.8, 1.7, 0.57, and 26.9 μM, respectively. All four active tyrosinase inhibitors ( 1 , 3 – 5 ) were competitive inhibitors. Interestigly they all mainfested simple reversible slow-binding inhibition against diphenolase. The most potent inhibitor, compound 4 diplayed the following kinetic parameters k 3  = 0.0993 μM −1  min −1 , k 4  = 0.0048 min -1 , and K i app  = 0.0485 μM.
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Thirteen kinds of citrus essential oils and their volatile flavor constituents were investigated for tyrosinase inhibitory activity. Eureka lemon, Lisbon lemon, Keraji, and Kiyookadaidai significantly inhibited the oxidation of l-dihydroxy phenylalanine (l-DOPA) by mushroom tyrosinase. Citral and myrcene among volatile flavor constituents of citrus essential oils exhibited tyrosinase inhibitory activities with Ki values of 0.318 and 2.38 mM, respectively. The inhibition kinetics analyzed by a Li...
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Tyrosinases are type-3 copper proteins involved in the initial step of melanin synthesis. These enzymes catalyse both the o-hydroxylation of monophenols and the subsequent oxidation of the resulting o-diphenols into reactive o-qui-nones, which evolve spontaneously to produce intermediates, which associate in dark brown pigments. In fungi, tyrosinases are generally associated with the formation and stability of spores, in defence and virulence mechanisms, and in browning and pigmentation. First c...
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Abstract The kinetic behaviour of tyrosinase is very complex because the enzymatic oxidation of monophenol and o-diphenol to o-quinones occurs simultaneously with the coupled non-enzymatic reactions of the latter. Both reaction types are included in the kinetic mechanism proposed for tyrosinase (Mechanism I [J. Biol. Chem. 267 (1992) 3801–3810]). We previously confirmed the validity of the rate equations by the oxidation of numerous monophenols and o-diphenols catalysed by tyrosinase from differ...
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