Synthetic Search for Cosmetic Ingredients: Preparations, Tyrosinase Inhibitory and Antioxidant Activities of Caffeic Amides.

Tada, Takahiro; Ohnishi, Kazuomi; Komiya, Takashi; Imai, Kunio

doi:10.5650/jos.51.19

Cited by 6 publications

(5 citation statements)

References 10 publications

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“…Tyrosinase Inhibitory Activity. The activity of mushroom tyrosinase (EC 1.14.18.1) was determined using L-tyrosine and L-DOPA as substrates according to a modified method of Tada et al (18). The activity was expressed as the sample concentration that gave a 50% inhibition in the enzyme activity (IC50).…”

Section: Introductionmentioning

confidence: 99%

In Vitro Antioxidative Effects and Tyrosinase Inhibitory Activities of Seven Hydroxycinnamoyl Derivatives in Green Coffee Beans

Iwai

Kishimoto

Kakino

et al. 2004

J. Agric. Food Chem.

234

140

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Seven kinds of hydroxycinnamic acid derivatives identified as 3-caffeoylquinic acid (3-CQA), 4-caffeolyquinic acid (4-CQA), 5-caffeoylquinic acid (5-CQA), 5-feruloylquinic acid (5-FQA), 3,4-dicaffeoylquinic acid (3,4-diCQA), 3,5-dicaffeoylquinic acid (3,5-diCQA), and 4,5-dicaffoylquinic acid (4,5-diCQA) by MS, 1H NMR, and HPLC analyses were isolated from low-quality (immature) and commercial quality green coffee beans. The quantity of chlorogenic acid isomers (10.4 g/100 g), especially 5-CQA, in commercial green coffee beans [West Indische Bereiding (West India processing beans from Sumatra Island, Indonesia, WIB)] was higher than that in low-quality beans [9.1 g/100 g, Eerste Kwaliteit (Export low-quality beans from Java Island, Indonesia, EK-1, grade 4)], whereas little difference in diCQAs was detected between the two kinds of beans. The free radical scavenging activity of these isolates was evaluated in assay systems using DPPH free radicals and superoxide anion radicals generated by xanthine-XOD. The diCQAs showed strong (1.0-1.8-fold) free radical scavenging activity compared to commonly used antioxidants such as alpha-tocopherol and ascorbic acid. The potency order of superoxide anion radical scavenging activity was diCQAs > caffeic acid, CQAs > 5-FQA. The activities of the diCQAs were twice as effective as those of CQAs and 4 times as effective as that of 5-FQA. The diCQAs also exhibited more potent (2.0-2.2-fold) tyrosinase inhibitory activities compared to CQAs, arbutin, and ascorbic acid. The isolates exhibited antiproliferation activities in four cancer cell lines, U937, KB, MCF7, and WI38-VA. Among these, KB cells were most sensitive (IC50 = 0.10-0.56 mM).

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Section: Introductionmentioning

confidence: 99%

In Vitro Antioxidative Effects and Tyrosinase Inhibitory Activities of Seven Hydroxycinnamoyl Derivatives in Green Coffee Beans

Iwai

Kishimoto

Kakino

et al. 2004

J. Agric. Food Chem.

234

140

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“…However, the possibility that the higher inhibitory activity observed following conjugation with DHLA is not due to the presence of the sulfur substituent, per se, but rather to the hydrophobicity acquired by the compound cannot be excluded. Actually, the tyrosinase inhibition properties of caffeoyl-amino acidyl-hydroxamic acid derivatives have been ascribed in part to their hydrophobicity, making them suitable for binding to the active site of tyrosinase [26,27,28].…”

Section: Resultsmentioning

confidence: 99%

“…Among the catecholic compounds of natural origin, a prominent position is occupied by caffeic acid (3,4-dihydroxycinnamic acid) due to its health-beneficial properties [22,23,24]. A number of caffeic acid derivatives, mostly amides, have been described as tyrosinase inhibitors, while caffeic acid is not, and this ability has been attributed to both the structural similarity of the caffeic acid moiety to the substrate 3,4-dihydroxy- l -phenylalanine ( l -DOPA) [20] and to the hydrophobicity and copper-chelating properties imparted by the particular nitrogen substituents [25,26,27,28].…”

Section: Introductionmentioning

confidence: 99%

2-S-Lipoylcaffeic Acid, a Natural Product-Based Entry to Tyrosinase Inhibition via Catechol Manipulation

et al. 2017

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Conjugation of naturally occurring catecholic compounds with thiols is a versatile and facile entry to a broad range of bioinspired multifunctional compounds for diverse applications in biomedicine and materials science. We report herein the inhibition properties of the caffeic acid-dihydrolipoic acid S-conjugate, 2-S-lipoylcaffeic acid (LC), on mushroom tyrosinase. Half maximum inhibitory concentration (IC 50 ) values of 3.22 ± 0.02 and 2.0 ± 0.1 µM were determined for the catecholase and cresolase activity of the enzyme, respectively, indicating a greater efficiency of LC compared to the parent caffeic acid and the standard inhibitor kojic acid. Analysis of the Lineweaver-Burk plot suggested a mixed-type inhibition mechanism. LC proved to be non-toxic on human keratinocytes (HaCaT) at concentrations up to 30 µM. These results would point to LC as a novel prototype of melanogenesis regulators for the treatment of pigmentary disorders.

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“…The activity of mushroom tyrosinase was spectrophotometrically determined as previously described with minor modifications [17] . l -DOPA (2mM, 0.05 mL) in phosphate-buffered saline (PBS; 50mM, pH 6.8) and 0.05 mL of the same buffer with or without test sample were added to a 96-well microplate; then, 0.05 mL of mushroom tyrosinase (200 U/mL) was mixed in.…”

Section: Methodsmentioning

confidence: 99%

Applications of Panax ginseng leaves-mediated gold nanoparticles in cosmetics relation to antioxidant, moisture retention, and whitening effect on B16BL6 cells

Pérez

Singh

Kim

et al. 2018

Journal of Ginseng Research

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BackgroundBioactive compounds in plant extracts are able to reduce metal ions to nanoparticles through the process of green synthesis. Panax ginseng is an oriental medicinal herb and an adaptogen which has been historically used to cure various diseases. In addition, the P. ginseng leaves-mediated gold nanoparticles are the value-added novel materials. Its potential as a cosmetic ingredient is still unexplored. The aim of this study was to evaluate the antioxidant, moisture retention and whitening properties of gold nanoparticles (PgAuNPs) in cosmetic applications.MethodsCell-free experiments were performed to evaluate PgAuNP's antioxidant and moisture retention properties and inhibition activity on mushroom tyrosinase. Furthermore, in vitro cell cytotoxicity was evaluated using normal human dermal fibroblast and murine B16BL6 melanoma cells (B16) after treatment with increasing concentrations of PgAuNPs for 24 h, 48 h, and 72 h. Finally, in vitro cell assays on B16 cells were performed to evaluate the whitening effect of PgAuNPs through reduction of cellular melanin content and tyrosinase activity.ResultsIn vitro DPPH radical scavenging assay results revealed that PgAuNPs exhibited antioxidant activity in a dose-dependent manner. PgAuNPs exhibited moisture retention capacity and effectively inhibited mushroom tyrosinase. In addition, 3-(4,5-dimethyl-thiazol-2yl)-2,5-diphenyl tetrazolium bromide results revealed that PgAuNPs were not toxic to human dermal fibroblast and B16 cells; in addition, they significantly reduced melanin content, tyrosinase activity, and mRNA expression of melanogenesis-associated transcription factor and tyrosinase in B16 cells.ConclusionOur study is the first report to provide evidence supporting that P. ginseng leaves-capped gold nanoparticles could be used as multifunctional ingredients in cosmetics.

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Synthetic Search for Cosmetic Ingredients: Preparations, Tyrosinase Inhibitory and Antioxidant Activities of Caffeic Amides.

Cited by 6 publications

References 10 publications

In Vitro Antioxidative Effects and Tyrosinase Inhibitory Activities of Seven Hydroxycinnamoyl Derivatives in Green Coffee Beans

In Vitro Antioxidative Effects and Tyrosinase Inhibitory Activities of Seven Hydroxycinnamoyl Derivatives in Green Coffee Beans

2-S-Lipoylcaffeic Acid, a Natural Product-Based Entry to Tyrosinase Inhibition via Catechol Manipulation

Applications of Panax ginseng leaves-mediated gold nanoparticles in cosmetics relation to antioxidant, moisture retention, and whitening effect on B16BL6 cells

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