• Natural Product Sciences
• /
• v.3 no.2
• /
• pp.111-121
• /
• 1997

Tyrosinase catalyzes the rate-limiting steps in melanin biosynthesis which is involved in skin-coloring and local hyperpigmentation of human beings, and unfavorable darkening of food products, Inhibitory effects on 3,4-dihydroxy-phenylalanine (dopa) oxidase activity of tyrosinase by 594 kinds of herbal extracts prepared from herbal medicines and wild plants in Korea were estimated. Two herbal extracts prepared from radicis cortex of Morus alba and rhizoma of Curcuma longa were selected as those exhibiting potent inhibitory effects on the enzyme activity. These herbal extracts were subjected to sequential fractionations with methylene chloride, ethyl acetate, n-butanol, and polar residue. The inhibitory effects on dopa oxidase activity of tyrosinase were shown in ethyl acetate fraction of Morus alba, and in methylene chloride fraction of Curcuma langa. The ethyl acetate fraction of Marus alba exhibited 50% of inhibition on dopa oxidase activity of tyrosinase at the concentration of 12 ${\mu}g/ml$, and methylene chloride fraction of Curcuma langa at 51 ${\mu}g/ml$.

• Journal of the Society of Cosmetic Scientists of Korea
• /
• v.36 no.3
• /
• pp.199-205
• /
• 2010

The structure-activity relationships (SARs) between a series of phenyl-2,2'-methylenebis(cyclohexane-1,3-dione) analogues (1-22) as substrate molecules and their inhibitory activity against tyrosinase were studied quantitatively using molecular hologram quantitative structure-activity relationships (HQSARs). Based on the results, new compounds with the increased tyrosinase inhibitory activity were designed. In addition, statistically favored E-2 model ($q_2$ = 0.564 & $r_2$ = 0.929) was derived. It is predicted that the activity of the most potent one (P1) of compounds newly designed by the optimized HQSAR E-2 model was $Pred.pI_{50}$ = 5.48 and the predicted inhibitory activity was about 13.4 fold higher than that of the kojic acid used as standard compound.

• YAKHAK HOEJI
• /
• v.43 no.1
• /
• pp.28-32
• /
• 1999

Four derivatives of kojic acid were synthesized and their inhibitory activities against tyrosinase were evaluated. The C-2 hydroxymethyl and C-7 hydroxyl of kojic acid were replaced by carboxylate and amine, respectively. These derivatives were coupled to L-phenylalanine, producing two amide compounds. The carboxylate derivative (3), its amide compound (5), and the amine derivative (7) were weak inhibitors. The amide compound (9) where amine derivative (7) coupled to L-phenylalanine showed strong inhibitory activity ($IC_{50}=24.6{\;}{\mu}M$) comparable to kojic acid.

• Animal cells and systems
• /
• v.10 no.4
• /
• pp.233-236
• /
• 2006

For the purpose of the development of skin-whitening or therapeutic agents against hyperpigmentation, aqueous extract from Nardostachys chinensis (AENC) was evaluated for melanogenesis inhibitory activity in B16F10 melanoma cell. The treatment with AENC at the 0.2, 0.5 and 1.0 mg/ml level significantly inhibits the biosynthesis of melanin compared with untreated control. The tyrosinase activity also significantly decreased in AENC-treated cells at the 0.2 and 0.5 mg/ml level and inhibitory effects were more efficient than commercial arbutin at 0.1 mg/ml. The Western analyses confirmed the significantly decreased expression of tyrosinase and tyrosinase-related protein-2 by AENC treatment. These results indicate that AENC may contribute to the inhibition of melanin biosynthesis through regulating the expression as well as activity of tyrosinase and AENC may be useful as a new candidate in the design of new skinwhitening or therapeutic agents.

• Journal of the Society of Cosmetic Scientists of Korea
• /
• v.30 no.1
• /
• pp.33-38
• /
• 2004

Melanin pigmentation in human skin is a major defense mechanism against ultraviolet light of the sun, but abnormal pigmentation such as freckles, liver spot could be a serious aesthetic problem. Nearly all studies are mainly concentrated on searching for the materials that have inhibitory activities on tyrosinase. In this work, to isolate phenolic compounds from Gastrodia elata, we purified the extract through solvent fractionation, column chromatography, and recrystallization. They were identified as 4-hydroxybenzyl alcohol 1, bis(4-hydroxyphenyl)methane 2, gastrodin (4-${\beta}$-D-glucopyranosyloxybenzyl alcohol) 3 on the base of spectroscopic evidences. In order to investigate their depigmentation effect, inhibitory activity against mushroom tyrosinase and inhibitory activity of melanin synthesis in B16 melanoma cells were evaluated in vitro. We have found that 4-hydroxybenzyl alcohol 1 and gastrodin (4- ${\beta}$-D-glucopyranosyloxybenzyl alcohol) 3 have no tyrosinase inhibitory activity, but inhibit the melanin synthesis in B16 melanoma cells. Tyrosinase inhibitory activities of bis(4-hydroxyphenyl)methane 2 (IC$\_$50/ = 400 $\mu\textrm{g}$/mL) and butanol fraction (IC$\_$50/ = 46 $\mu\textrm{g}$/mL) were lower/higher than that of arbutin (IC$\_$50/ = 114 $\mu\textrm{g}$/mL), but inhibitory activities of melanin synthesis in B16 melanoma cells were much higher than that of arbutin. Especially, tyrosinase inhibitory activities of isolated phenolic fraction (IC$\_$50/ = 2.37 $\mu\textrm{g}$/mL) from butanol fraction was very higher than that of arbutin (IC$\_$50/ = 114 $\mu\textrm{g}$/mL). Therefore, these results suggest that isolated phenolic compounds from Gastrodia elata have inhibitory activity against mushroom tyrosinase and inhibitory activity of melanin synthesis in 816 melanoma cells in vitro.

• Korean Journal of Pharmacognosy
• /
• v.35 no.4 s.139
• /
• pp.380-383
• /
• 2004

The purpose of this study was to evaluate mushroom Tyrosinase inhibitory activity of Cuscuta japonica Choisy and C. australis R.Be. The experimental materials were expressed juice from their stems and flowers, both water and ethanol extracts, their seeds, and two kinds of commercially available cosmetic packing Wontosa and Bupjetosa (made from seeds of C. japonica). The 50% inhibitory concentration $(IC_{50})$ of C. Japonica juice was 5.4 mg/ml. However, C. australis juice showed negligible mushroom tyrosinase inhibitory activity. The $IC_{50}$ of water extracted C. japonica seed was $54.0\;{\mu}g/ml$, water extracted product of Wontosa $50.0\;{\mu}g/ml$ and Bupjetosa $40\;{\mu}g/ml$. The $IC_{50}$ of ethanol extracted C. japonica seed was $10\;{\mu}g/ml$, Wontosa $10\;{\mu}g/ml$ and Bupjetosa $20\;{\mu}g/ml$.

• YAKHAK HOEJI
• /
• v.41 no.4
• /
• pp.518-523
• /
• 1997

To isolate biologically active compounds which exhibit tyrosinase inhibition activity and ultimately express skin whitening effect, 14 oriental herbal drugs were screened in ter ms of tyrosinase inhibition. For this purpose, in vitro enzyme assay system for tyrosinase, so called Pomerantz method with some modifications has been established. Crude methanolic extracts from 14 herbal drugs were made and examined for their inhibitory activity against tyrosinase. Those extracts from Cnidii Rhizoma, Arecae Semen, Caryophylli Flos, and Ephedrae Herba showed strong inhibitory activities on mushroom tyrosinase. Therefore, crude methanolic extracts from those 4 herbal drugs were further fractionated using ether, butanol and water. respectively. The ether and n-butanol extracts from Arecae Semen and the n-butanol and water extracts from Caryophylli Flos, respectively, showed relatively strong tyrosinase inhibitory activity compared to arbutin.

• Fisheries and Aquatic Sciences
• /
• v.3 no.3_4
• /
• pp.195-199
• /
• 2000

Tyrosinase inhibitory activities of 14 kinds of seaweed, Ecklonia stolonifera, Ecklonia cava, Undaria pinnatiflda, Laminaria japonica, Sargassum fulvellum, Sargassum miyabei, Sargassum thunbergii, Porphyra yezoensis, Gracilaria verrucosa, Carpopeltis affinis, Pachymeniopsis elliptica, Gelidium amansii, Codium fragile and Ulva pertusa were determined using commercially available mushroom tyrosinase in an in vitro assay system. The $1\%$ (w/v) methanol extract from E. stolonifera showed the highest tyrosinase inhibitory activity of $79.0\%$, electron donating activity of $79.0\%$ and total phenol content of 3.75 mg/100g. Ethyl acetate-methanol-water (7 : 2 : 0.2, v/v) fraction $(0.5\%,\;w/v)$ isolated from the methanol extract showed tyrosinase inhibitory activity of $75.9 \%$, electron donating activity of $88.1 \%$ and total phenol content of 4.38 mg/100g. Tyrosinase inhibitory activity was closely associated with total phenol content (R = 0.99) and electron donating activity (R=0.99). Maximum absorption wavelength of the fraction was 218nm and that of phenolic compounds showed about a range from 210 to 220nm. The inhibition mode of the fraction was noncompetitive inhibition.

• Journal of the Korean Applied Science and Technology
• /
• v.34 no.2
• /
• pp.296-304
• /
• 2017

The purpose of this study was to investigate the applicability of the Psidium guajava leaf extract as a whitening functional cosmetic material. We measured DPPH radical scavenging activity, intracellular ROS, cytotoxicity in B16F10 melanoma cells and cytoprotective effect on ultraviolet A, in vitro tyrosinase inhibitory effect and melanin biosynthesis inhibitory effect. The antioxidative effect was confirmed through high DPPH radical scavenging activity and intracellular ROS activity inhibition measurement of the Psidium guajava leaf extract. The survival rate of B16F10 melanoma cells was more than 98% at all concentrations, and the cytoprotective effect from ultraviolet ray A was found to increase in a concentration-dependent manner. In addition, in vitro tyrosinase activity inhibitory effect of 10% and melanin biosynthesis inhibitory effect of 20% were observed. Through less toxicity for B16F10 melanoma cell, high antioxidant activity, inhibition of tyrosinase activity and melanin biosynthesis inhibitory effect, we confirmed the possibility of developing the Psidium guajava leaf extract as a whitening functional cosmetic material with a safe and excellent whitening effect.

• Archives of Pharmacal Research
• /
• v.22 no.4
• /
• pp.335-339
• /
• 1999

The oxidation-reduction potentials of cosmetic raw materials, showing tyrosinase inhibitory action, and phenolic compounds structurally similar to L-tyrosine were determined by cylcic voltammetry. The voltammograms obtained could be classified ito 4 patterns (patterns 1-4). Patterns 1, characterized by oxidation and reduction peaks as a pair, was observed with catechol, hydroquinone or phenol, and pattern 2 exhibiting another oxidation peak in addition to oxidation and reduction peaks as a pair was found with arbutin, kojic acid, resorcinol, methyl p-hydroxybenzoate and L-tyrosine as the substrate of tyrosinase. Pattern 3 with an independent oxidation peak only was expressed by L-ascorbic acid, and pattern 4 with a reduction peak only at high potentials, by hinokitiol. The tyrosinase inhibitory activity of these compounds was also evaluated using the 50% inhibitory concentration ($IC_{50}$) and the inhibition constant (Ki) as parameters. Hinokitiol, classified as patterns 4, showed the highest inhibitory activity (lowest $IC_{50}$ and Ki). Hydroquinone showing the second highest activity belonged to pattern 1, which also included compounds exhibiting pattern 2 was relatively low with Ki values being in the order of 10-4 M. Although there was no consistent relationship between oxidation-reduction potentials and tyrosinase inhibitory action, the voltammetry data can be used as an additional index to establish the relationship between the structure and the tyrosine inhibitory activity.