Tyrosinase inhibitors isolated from the roots of <i>Paeonia suffruticosa</i>

Ding, Hsiou-Yu; Lin, H. -C.; Chang, Ting-Kai

doi:10.1111/j.1468-2494.2010.00549_4.x

Cited by 12 publications

(11 citation statements)

References 16 publications

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“…In a previous study, a gallic acid methyl derivative was shown to be a poorer inhibitor of the diphenolase activity of mushroom tyrosinase than gallic acid or kojic acid (Nithitanakool et al 2009 ). Meanwhile, the glycosylated forms of gallic acid (pentagalloyl glucopyranose) isolated from the seed kernels of Mangifera indica (Nithitanakool et al 2009 ) and the roots of Paeonia suffruticosa (Ding et al 2009 ) have been reported to be 16 times stronger than gallic acid for the inhibition of mushroom tyrosinase in a non-competitive inhibition manner. The previous studies correlated well with this finding that glycosylated gallic acid (1.23 mM) showed a slightly stronger whitening effect with a lower Ki value than gallic acid itself (1.98 mM) by mixed noncompetitive inhibition, instead of competitive-type inhibition (Fig.…”

Section: Discussionmentioning

confidence: 99%

Transglycosylation of gallic acid by using Leuconostoc glucansucrase and its characterization as a functional cosmetic agent

et al. 2017

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Gallic acid glycoside was enzymatically synthesized by using dextransucrase and sucrose from gallic acid. After purification by butanol partitioning and preparative HPLC, gallic acid glucoside was detected at m/z 355 (C13, H16, O10, Na)+ by matrix-assisted laser desorption ionization time-of-flight mass spectrometry. The yield of gallic acid glucoside was found to be 35.7% (114 mM) by response surface methodology using a reaction mixture of 319 mM gallic acid, 355 mM sucrose, and 930 mU/mL dextransucrase. The gallic acid glucoside obtained showed 31% higher anti-lipid peroxidation and stronger inhibition (Ki = 1.23 mM) against tyrosinase than that shown by gallic acid (Ki = 1.98 mM). In UVB-irradiated human fibroblast cells, gallic acid glucoside lowered matrix metalloproteinase-1 levels and increased the collagen content, which was indicative of a stronger anti-aging effect than that of gallic acid or arbutin. These results indicated that gallic acid glucoside is likely a superior cosmetic ingredient with skin-whitening and anti-aging functions.Electronic supplementary materialThe online version of this article (10.1186/s13568-017-0523-x) contains supplementary material, which is available to authorized users.

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Section: Discussionmentioning

confidence: 99%

Transglycosylation of gallic acid by using Leuconostoc glucansucrase and its characterization as a functional cosmetic agent

et al. 2017

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“…Although melanin mainly plays a photoprotective role, the accumulation of abnormal amounts of melanin in different parts of the skin, results in pigmented patches on skin, poses as an esthetic problem. Therefore, several studies have been carried out to identify methods of inhibition of tyrosinase activity and the prevention of abnormal pigmentation (Ding et al, 2009;Chang et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Inhibitory effect of danazol on melanogenesis in mouse B16 melanoma cells

Chang

Lin

2010

Arch. Pharm. Res.

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In the present study, more than 200 generic drugs were screened to verify their applicability as a skin-lightening agent using mouse B16 melanoma cells. Of the numerous agents, danazol was found to inhibit melanogenesis in B16 cells in a dose-dependent manner with an IC(50) value of 9.3 μM. In addition, danazol reduced cellular tyrosinase activity in B16 cells but did not directly inhibit the murine tyrosinase activity in the cell-free system. Western blotting analysis confirmed that danazol downregulated the levels of tyrosinase protein in B16 cells, and reverse-transcription polymerase chain reaction (RT-PCR) analysis revealed that danazol did not downregulate the levels of tyrosinase mRNA in the cells. These results indicate that danazol inhibits melanogenesis in B16 cells via reducing the tyrosinase activity by post-transcriptional regulation.

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“…Because tyrosinase is a rate-limiting enzyme related to the first two steps of melanogenesis, agents possessing tyrosinase inhibitory activity can be regarded as potential candidates for a depigmentation strategy [ 39 ]. Therefore, tyrosinase activity was analyzed for evaluation of the involved mechanisms of VARM and its solvent fractions-induced antimelanogenesis in B16F10 cells.…”

Section: Discussionmentioning

confidence: 99%

Vitis amurensisRuprecht root inhibited α-melanocyte stimulating hormone-induced melanogenesis in B16F10 cells

Jin

Hyun

et al. 2014

Nutr Res Pract

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BACKGROUND/OBJECTIVESThe root of Vitis amurensis Ruprecht, a sort of wild-growing grape, has been used in oriental medicine for treatment of skin ailments; however, its dermatological activity is not sufficiently understood. The aim of this study was to investigate tyrosinase inhibitory and anti-melanogenic activities of V. amurensis Ruprecht root methanol extract (VARM) in B16F10 mouse melanoma cells and to attempt to isolate and identify the active compound issued from VARM.MATERIALS/METHODSAnti-melanogenic activity of VARM was analyzed in α-melanocyte stimulating hormone (MSH)-stimulated B16F10 cells through evaluation of antioxidative activity as well as inhibited tyrosinase activity and melanin contents compared with those of kojic acid and arbutin. After anti-melanogenic analysis of VARM, serial fractionation, nuclear magnetic resonance (NMR), and thin layer chromatorgraphy (TLC) were applied for identification of active compounds contained in VARM.RESULTSVARM significantly inhibited oxidative stress and tyrosinase activity and attenuated α-MSH-induced melanin production in B16F10 cells. For isolation of active compounds, VARM was fractionated using a series of organic solvents, including dichloromethane (CH2Cl2), ethyl acetate (EtOAc), and n-butanol (n-BuOH). Among fractions showing anti-melanogenic activity, the CH2Cl2 fraction induced the most potent attenuation of melanogenesis without cytotoxicity and the major compound in the CH2Cl2 fraction was identified as betulinic acid. Betulinic acid isolated from the CH2Cl2 fraction of VARM significantly attenuated α-MSH-induced melanogenesis in a dose dependent manner, which was stronger than that of arbutin used as a positive control.CONCLUSIONSThese results indicate that VARM inhibits oxidative stress, tyrosinase activity, and α-MSH-induced melanogenesis in B16F10 cells, due primarily to the active compound, betulinic acid, in the CH2Cl2 fraction.

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Tyrosinase inhibitors isolated from the roots of Paeonia suffruticosa

Cited by 12 publications

References 16 publications

Transglycosylation of gallic acid by using Leuconostoc glucansucrase and its characterization as a functional cosmetic agent

Transglycosylation of gallic acid by using Leuconostoc glucansucrase and its characterization as a functional cosmetic agent

Inhibitory effect of danazol on melanogenesis in mouse B16 melanoma cells

Vitis amurensisRuprecht root inhibited α-melanocyte stimulating hormone-induced melanogenesis in B16F10 cells

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