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1.
Exp Dermatol ; 20(11): 950-2, 2011 Nov.
Article in English | MEDLINE | ID: mdl-21843252

ABSTRACT

We synthesized a novel derivative of a well-known skin-lightening compound niacinamide, N-nicotinoyl dopamine (NND). NND did not show inhibitory effects of tyrosinase and melanin synthesis in B16F10 mouse melanoma cells. However, NND retains high antioxidant activity without affecting viability of cells. In a reconstructed skin model, topical applications of 0.05% and 0.1% NND induced skin lightening and decreased melanin production without affecting the viability and morphology of melanocytes and overall tissue histology. Moreover, no evidence for skin irritation or sensitization was observed when 0.1% NND emulsion was applied onto the skin of 52 volunteers. The effect of NND on skin lightening was further revealed by pigmented spot analyses of human clinical trial. Overall, NND treatment may be a useful trial for skin lightening and treating pigmentary disorders.


Subject(s)
Antioxidants/pharmacology , Dopamine/analogs & derivatives , Niacinamide/analogs & derivatives , Skin Pigmentation/drug effects , Animals , Bleaching Agents/pharmacology , Cell Line , Cell Line, Tumor , Dopamine/pharmacology , Humans , Hyperpigmentation/drug therapy , Melanoma, Experimental , Mice , Niacinamide/pharmacology
2.
Bioorg Med Chem Lett ; 20(24): 7534-6, 2010 Dec 15.
Article in English | MEDLINE | ID: mdl-21050756

ABSTRACT

The tyrosinase inhibitory activity of ethanolic extract of kenaf (Hibiscus cannabinus L.) leaf was evaluated before and after subjecting it to far-infrared (FIR) irradiation. The main component of the extract was analyzed as kaempferitrin (kaempferol-3,7-O-α-dirhamnoside). Prior to FIR irradiation, no inhibitory activity of the extract was detected in a tyrosinase assay. However, after FIR irradiation for 1h at 60°C, significant tyrosinase inhibitory activity (IC(50)=3500 ppm) was observed in it. In HPLC analysis, derhamnosylation products (kaempferol, afzelin, and α-rhamnoisorobin) were detected. The inhibitory activity may be due to the existence of derhamnosylation products. This study demonstrated that FIR irradiation can be used as a convenient tool for deglycosylation of flavonoid glycoside.


Subject(s)
Flavonoids/metabolism , Hibiscus/chemistry , Infrared Rays , Monophenol Monooxygenase/antagonists & inhibitors , Flavonoids/chemistry , Kaempferols/chemistry , Kaempferols/isolation & purification , Kaempferols/pharmacology , Mannosides/chemistry , Mannosides/isolation & purification , Mannosides/pharmacology , Monophenol Monooxygenase/metabolism , Plant Extracts/chemistry , Plant Leaves/chemistry , Proanthocyanidins/chemistry , Proanthocyanidins/isolation & purification , Proanthocyanidins/pharmacology
3.
Bioorg Med Chem Lett ; 20(22): 6569-71, 2010 Nov 15.
Article in English | MEDLINE | ID: mdl-20934336

ABSTRACT

This study was conducted to examine the tyrosinase inhibitory and anti-inflammatory activities of kojic acid derivatives. A series of kojic acid derivatives containing thioether, sulfoxide, and sulfone linkages were synthesized. In the tyrosinase assay, kojyl thioether derivatives containing appropriate lipophilic alkyl chains (pentane, hexane, and cyclohexane) showed potent inhibitory activity. However, sulfoxides and sulfones exhibited decreased activity. Similar experimental results were obtained with inhibitory activities of NO production being induced by LPS. The presence of thioether linkage and appropriated lipophilic acid moiety was critical for the tyrosinase inhibitory and anti-inflammatory activities.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Monophenol Monooxygenase/antagonists & inhibitors , Sulfides/pharmacology , Anti-Inflammatory Agents/chemistry , Models, Molecular , Sulfides/chemistry
4.
J Ind Microbiol Biotechnol ; 37(6): 631-7, 2010 Jun.
Article in English | MEDLINE | ID: mdl-20411402

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 IC(50) of 53.6 and 0.49 microM, 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.


Subject(s)
Disaccharides/metabolism , Enzyme Inhibitors/metabolism , Monophenol Monooxygenase/antagonists & inhibitors , Morus/metabolism , Stilbenes/metabolism , Agaricales/enzymology , Biotransformation , Disaccharides/isolation & purification , Disaccharides/pharmacology , Enzyme Inhibitors/pharmacology , Monophenol Monooxygenase/metabolism , Plant Extracts/metabolism , Stilbenes/isolation & purification , Stilbenes/pharmacology
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