In Vitro and In Vivo Prolonged Biological Activities of Novel Vitamin C Derivative, 2-O-.ALPHA.-D-Glucopyranosyl-L-Ascorbic Acid (AA-2G), in Cosmetic Fields.

Kumano, Yoshimaru; Sakamoto, Tetsuo; Egawa, Mariko; Iwai, Ichiro; Tanaka, Muneo; Yamamoto, Ichiro

doi:10.3177/jnsv.44.345

Cited by 70 publications

(59 citation statements)

References 13 publications

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“…Among these compounds, esculetin (11), which has hydroxyl groups at the C6 and C7 positions of the coumarin ring, exhibited the strongest inhibitory activity (IC 50 ϭ0.043 mM), followed by umbelliferone (4) (IC 50 ϭ0.42 mM), which has only one hydroxy group at C7. Daphnetin (10), scopoletin (12), and 6,7-dihydroxy-4-methylcoumarin (14) showed a weak inhibitory effect and the other compounds were ineffective. The mutual comparison of these results indicates that the introduction of hydroxyl groups to the ortho position of C6 and C7 potentiates the inhibitory activity, and conversely, the introduction of hydroxyl groups to the ortho position of C7 and C8 drastically decreases the activity.…”

Section: Resultsmentioning

confidence: 99%

“…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.…”

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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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Inhibitory Effects of Esculetin on Melanin Biosynthesis

Masamoto

Murata

et al. 2004

Biological & Pharmaceutical Bulletin

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“…As shown in Fig. 11, (2S,7S,13R,14R,15S)-14-acetyl-14-hydroperoxy-2,13,15-trimethyltetracyclo [8.7.0.0 2,7 .0 11,15 ]heptadec-5-yl acetate (C 24 H 38 O 5 ) inhibited melanin accumulation at 0.5 mg/ml (1.23 mM), although it was less effective than compound [1].…”

Section: Effect Of Similar Hydroperoxy Compound On Melanin Accumulationmentioning

confidence: 99%

“…For example, hydroquinone and 4-methoxyphenol are used as topical therapies for hyperpigmentation disorders. Active ingredients available for medicated whitening cosmetics in Japan include vitamin C and its stabilized phosphate 1) and glucoside derivatives, 2) kojic acid, 3) arbutin, 4) linoleic acid, 5) tranexamic acid, 6) 3-O-ethyl ascorbic acid 7) and ellagic acid. 8) Among them, kojic acid, arbutin, linoleic acid and ellagic acid are plant products.…”

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