Mushroom Tyrosinase Inhibitory Activity of Esculetin Isolated from Seeds of<i>Euphorbia lathyris</i>L.

Masamoto, Yukimitsu; Ando, Hironori; Murata, Yoshiyuki; Shimoishi, Yasuaki; Tada, Mikiro; Takahata, Kyoya

doi:10.1271/bbb.67.631

Cited by 204 publications

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“…16) To the best of our knowledge, this is the first report of the tyrosinase-inhibitory effects of esculetin. In this study, 18 coumarins and four cinnamic acid derivatives were examined for antityrosinase activity and study of the structure-activity relationship.…”

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confidence: 80%

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Inhibitory Effects of Esculetin on Melanin Biosynthesis

Masamoto

Murata

et al. 2004

Biological & Pharmaceutical Bulletin

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Coumarins are widely distributed in plants and are especially abundant in the bark, leaves, and roots of Umbelliferae and Rutaceae plants. So far more than 1300 types of coumarin have been identified as natural or synthesized compounds. Coumarins have recently been reported to have interesting pharmacologic and biochemical properties such as antioxidative, 1,2) antiinflammatory, and antiallergic effects, 3,4) inhibition of platelet aggregation 5) and protein kinase, 6) induction of apoptosis, 7) and antiviral, 8) antidifferentiative, 9) and antimutagenic activity. 10)Melanin pigment is a heteropolymer of indole compounds synthesized within melanocytes in the epidermis. Inhibitory compounds on melanogenesis are useful as skin-whitening agents used in cosmetics and as treatment of hyperpigmentation. Tyrosinase is known to play a critical regulatory role in melanin biosynthesis. 11) Therefore, many tyrosinase inhibitors that suppress melanogenesis in epidermal layers have been actively studied in cosmetics and pharmaceuticals. [12][13][14][15] These observations led us to search for naturally occurring tyrosinase inhibitors.Recently, we have isolated esculetin from the seeds of Euphorbia lathyris L. as a mushroom tyrosinase inhibitory compound.16) To the best of our knowledge, this is the first report of the tyrosinase-inhibitory effects of esculetin. In this study, 18 coumarins and four cinnamic acid derivatives were examined for antityrosinase activity and study of the structure-activity relationship. We evaluated further the inhibitory effect on melanin synthesis in B16 melanoma cells and guinea pig epidermal sheets of esculetin, which showed the strongest inhibitory activity among these compounds. MATERIALS AND METHODS MaterialsCoumarin, 4-hydroxycoumarin, umbelliferone, 7-methoxycoumarin, 6-hydroxy-4-methylcoumarin, 7-hydroxy-4-methylcoumarin, esculin, esculetin, scopoletin, 7-hydroxycoumarin-4-acetic acid, and 7-hydroxycoumarin-3-carboxylic acid were purchased from Aldrich Chemical Co. (Milwaukee, WI, U.S.A.). 4-Methylesculetin, 5,7-dihydroxy-4-methylcoumarin, isoscopoletin, and fraxetin were obtained from Extrasynthese Co. (Genay, France). Daphnetin, daphnin, and daphnetin-8-glucoside were isolated from Daphne odora. The chemicals purchased were used as received.Assay of Tyrosinase-Inhibitory Activity The assay was performed as previously described.16) One milliliter of a 1.5 mM L-3,4-dihydroxyphenylalanine (DOPA) solution, 0.1 ml of dimethyl sulfoxide (DMSO) with or without sample, and 1.8 ml of 1/15 M phosphoric acid buffer solution (pH 6.8) were mixed. The mixtures were preincubated at 25°C for 10 min. Then, 0.1 ml of the aqueous solution of mushroom tyrosinase (1000 U/ml, Sigma Chemical Co., St. Louis, MO, U.S.A.) was added, and the reaction was monitored at 475 nm. A control reaction was conducted with DMSO. The percentage of inhibition of tyrosinase activity was calculated as follows: inhibition (%)ϭ(AϪB)/Aϫ100, where A represents the difference in the absorbance of the control sample between the incub...

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“…16) One milliliter of a 1.5 mM L-3,4-dihydroxyphenylalanine (DOPA) solution, 0.1 ml of dimethyl sulfoxide (DMSO) with or without sample, and 1.8 ml of 1/15 M phosphoric acid buffer solution (pH 6.8) were mixed. The mixtures were preincubated at 25°C for 10 min.…”

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confidence: 99%

Inhibitory Effects of Esculetin on Melanin Biosynthesis

Masamoto

Murata

et al. 2004

Biological & Pharmaceutical Bulletin

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“…23) First, 300 ml of 2.5 mM 3,4-dihydroxyphenylalanine (L-DOPA) solution, 50 ml of dimethyl sulfoxide (DMSO) with or without a sample chemical, and 1.1 ml of 0.1 M phosphate buffer (pH 6.8) were mixed. The mixture was preincubated at 25°C for 10 min before 50 ml of 1380 units/ml tyrosinase in aqueous solution was added, and the reaction was monitored at 475 nm.…”

Section: Methodsmentioning

confidence: 99%

Down-Regulation of Tyrosinase Expression by Acetylsalicylic Acid in Murine B16 Melanoma

Sato

Takahashi

Iraha

et al. 2008

Biological & Pharmaceutical Bulletin

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Acetylsalicylic acid (aspirin; ASA) is one of the leading non-steroidal anti-inflammatory drugs (NSAIDs) and is known to act by directly suppressing the activity of cyclooxygenase (COX), the key enzyme catalyzing the biosynthesis of prostaglandins. ASA has wide range of effects and the most well known pharmacological effect is reducing pain or fever.1) Previous reports showed ASA and some other NSAIDs were able to prevent the development of cancer of the colon, breast, stomach, and lung.2-5) These biological effects of NSAIDs are the results of their anti-cancer ability, by inducing apoptosis and cell cycle arrest. 6) Moreover, ASA has been shown to be effective as an antiplatelet drug in preventing heart attacks, stroke, and cerebral thrombosis. 1,[7][8][9] Skin pigmentation results from melanin synthesis by melanocytes and is caused by exposure to UV radiation. Melanin plays an important role in the prevention of suninduced skin injury, and is a major determinant of skin color. 10,11) Tyrosinase is a key enzyme in melanin synthesis that catalyzes three different chemical reactions; the hydroxylation of tyrosine to 3,4-dihydroxyphenylalanine (DOPA), the oxidation of DOPA to DOPAquinone, and the oxidation of 5,6-dihydroxyindole (DHI) to indole-quinone.12) In the absence of thiols, DOPAquinone changes to DOPAchrome and then to DHI or indole 5,6-quinone 2-carboxylic acid (DHICA). There are two other factors in this melanogenic pathway, one is tyrosinase-related protein-2 (TRP-2; DOPAchrome tautomerase), which catalyzes the conversion of DOPAchrome to DHICA, and the other is TRP-1 (DHICA oxidase) that catalyzes the oxidation of DHICA.13-17) Cyclic AMP (cAMP) is a key messenger in melanin synthesis. 18) cAMP inducers such as a-melanocyte stimulating hormone (a-MSH), forskolin, and isobutylmethylxanthine (IBMX) enhance melanogenesis. 19) Investigation of the depigmenting mechanisms and clinical aspects of skin-whitening agents is very important. In addition, increased production and accumulation of melanin leads to many hyperpigmentation disorders such as melasma, postinflammatory pigmentation, solar lentigo, etc., which become prominent with aging. Many chemicals have been demonstrated to show inhibitory effects on melanogenesis through inhibition of the enzymatic activity of tyrosinase, but effects on related gene expression, protein degradation, glycosylation, melanosome transfer, and regulation of cellular signaling are also reported to control melanogenesis (reviewed by Solano et al. 20) and Briganti et al. 21)). Among these studies the effect of ASA on the pigmentary system is as yet unreported. Therefore, we conducted an investigation on the depigmenting mechanisms of ASA in murine B16 melanoma cells. In this study, we showed that ASA inhibited a-MSH-enhanced melanogenesis in B16 melanoma and this depigmenting mechanism was attributed to the downregulation of tyrosinase expression and/or the increase of tyrosinase degradation. MATERIALS AND METHODSCell Culture B16F1 murine melanoma cells were cultured in Dul...

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“…The whitening effects of OCE were measured by tyrosinase inhibitory assay 16) and melanin formation test in B16/F10 murine melanoma cells 17) in this study.…”

Section: Whitening Effectsmentioning

confidence: 99%

In Vitro Cytotoxicity, Skin Regeneration, Anti-wrinkle, Whitening and In Vivo Skin Moisturizing Effects of Oncheongeum

An¹,

Kim²

2016

The Journal of Oriental Obstetrics and Gynecology

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Objectives: The objective of this study was to evaluate the effects of cytotoxicity, skin regeneration, anti-wrinkle, whitening and skin moisturizing of Oncheongeum (OCE).Methods: The cytotoxicity of OCE lyophilized aqueous extracts (yield=13.82%) was observed against human normal fibroblast cells and B16/F10 murine melanoma cells by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium Bromide (MTT) assay, and skin regeneration and anti-wrinkle effects were also evaluated through the assay of collagen type I synthesis compared to the transformation of the growth factor (TGF)-β1, hyaluronidase, collagenase and matrix metalloproteinase (MMP)-1 inhibitory assays compared to oleanolic acid (OA), and elastase inhibitory effects compared to phosphoramidon disodium salt (PP). In addition, OCE's whitening effects were measured by a tyrosinase inhibitory assay and melanin formation test in B16/F10 murine melanoma cells compared to arbutin, and skin moisturizing effects were observed through a mouse skin water content test, respectively.Results: No OCE treatment-related cytotoxic effects appeared on human normal fibroblasts and B16/F10 murine melanoma cells. OCE concentration-dependently increased the collagen Type I synthesis on human normal fibroblast cells, and also effectively inhibited hyaluronidase, elastase, collagenase and MMP-1 activities. In addition, OCE inhibited melanin production of B16/F10 murine melanoma cells and activity of tyrosinase. And significant and dose-dependent increases of skin water content were detected in OCE-treated mouse skin compared to vehicle control skins.Conclusions: OCE showed favorable and sufficient effects in skin regeneration, anti-wrinkle, whitening and skin moisturizing in this experiment. But more detail mechanisms and studies on the skin protective efficiency of in vivo are needed with the screening of active biological compounds in individual OCE herbs.

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Mushroom Tyrosinase Inhibitory Activity of Esculetin Isolated from Seeds ofEuphorbia lathyrisL.

Cited by 204 publications

References 21 publications

Inhibitory Effects of Esculetin on Melanin Biosynthesis

Inhibitory Effects of Esculetin on Melanin Biosynthesis

Down-Regulation of Tyrosinase Expression by Acetylsalicylic Acid in Murine B16 Melanoma

In Vitro Cytotoxicity, Skin Regeneration, Anti-wrinkle, Whitening and In Vivo Skin Moisturizing Effects of Oncheongeum

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