Synthesis and evaluation of bibenzyl glycosides as potent tyrosinase inhibitors

Tajima, Reiko; Oozeki, Hiromi; Muraoka, Seiichi; Tanaka, Saori; Motegi, Yukari; Nihei, Hiroyuki; Yamada, Yoichi M. A.; Masuoka, Noriyoshi; Nihei, Keiji

doi:10.1016/j.ejmech.2011.01.065

Cited by 32 publications

(22 citation statements)

References 29 publications

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“…Mushroom tyrosinase inhibitory activity was evaluated using a previously reported method, with modifications. Briefly, a mixture of sodium phosphate buffer (pH 6.8, 1/15 mol/L; 1.2 mL), levodopa (L‐DOPA; 1.5 mmol/L; 0.5 mL) and DMSO sample solution (10 mg/mL; 0.2 mL) was added to the enzyme solution (500 U/mL; 0.1 mL), and the solution was then incubated at 30°C for 10 min.…”

Section: Methodsmentioning

confidence: 99%

Skin protective effect of guava leaves against UV‐induced melanogenesis via inhibition of ORAI1 channel and tyrosinase activity

Lee

Weon

Nam

et al. 2016

Experimental Dermatology

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Ultraviolet (UV) irradiation is a major environmental factor affecting photoageing, which is characterized by skin wrinkle formation and hyperpigmentation. Although many factors are involved in the photoageing process, UV irradiation is thought to play a major role in melanogenesis. Tyrosinase is the key enzyme in melanin synthesis; therefore, many whitening agents target tyrosinase through various mechanisms, such as direct interference of tyrosinase catalytic activity or inhibition of tyrosinase mRNA expression. Furthermore, the highly selective calcium channel ORAI1 has been shown to be associated with UV-induced melanogenesis. Thus, ORAI1 antagonists may have applications in the prevention of melanogenesis. Here, we aimed to identify the antimelanogenesis agents from methanolic extract of guava leaves (Psidium guajava) that can inhibit tyrosinase and ORAI1 channel. The n-butanol (47.47%±7.503% inhibition at 10 μg/mL) and hexane (57.88%±7.09% inhibition at 10 μg/mL) fractions were found to inhibit ORAI1 channel activity. In addition, both fractions showed effective tyrosinase inhibitory activity (68.3%±0.50% and 56.9%±1.53% inhibition, respectively). We also confirmed that the hexane fraction decreased the melanin content induced by UVB irradiation and the ET-1-induced melanogenesis in murine B16F10 melanoma cells. These results suggest that the leaves of P. guajava can be used to protect against direct and indirect UV-induced melanogenesis.

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Section: Methodsmentioning

confidence: 99%

Skin protective effect of guava leaves against UV‐induced melanogenesis via inhibition of ORAI1 channel and tyrosinase activity

Lee

Weon

Nam

et al. 2016

Experimental Dermatology

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“…Arbutin, a structural analog of hydroquinone, can be metabolized into hydroquinone (Blaut et al, 2006), increasing the possibility of getting cancer. Thus, much research has identified tyrosinase inhibitors synthesized in the laboratory (Kubo et al, 2000;Shiino et al, 2001;Jun et al, 2007;Jirawattanapong et al, 2009;Delogu et al, 2010;Yi et al, 2010;Cha et al, 2011;Tajima et al, 2011;Song et al, 2012;Hamidian, 2013;Hamidian et al, 2013;Zhu et al, 2013) and extracted from plants (Piao et al, 2009;Sung et al, 2009;Chang et al, 2011;Liang et al, 2012;Zheng et al, 2012;Sarkhail et al, 2013). Some attention has been drawn to applying peptide sequences for tyrosinase inhibition; however, most of them are fragments isolated from known proteins and peptide-derived compounds.…”

Section: Introductionmentioning

confidence: 99%

Phage Display–Mediated Discovery of Novel Tyrosinase-Targeting Tetrapeptide Inhibitors Reveals the Significance of N-Terminal Preference of Cysteine Residues and Their Functional Sulfur Atom

et al. 2014

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Tyrosinase, a key copper-containing enzyme involved in melanin biosynthesis, is closely associated with hyperpigmentation disorders, cancer, and neurodegenerative diseases, and as such, it is an essential target in medicine and cosmetics. Known tyrosinase inhibitors possess adverse side effects, and there are no safety regulations; therefore, it is necessary to develop new inhibitors with fewer side effects and less toxicity. Peptides are exquisitely specific to their in vivo targets, with high potencies and relatively few off-target side effects. Thus, we systematically and comprehensively investigated the tyrosinase-inhibitory abilities of N-and C-terminal cysteine/tyrosine-containing tetrapeptides by constructing a phage-display random tetrapeptide library and conducting computational molecular docking studies on novel tyrosinase tetrapeptide inhibitors. We found that N-terminal cysteine-containing tetrapeptides exhibited the most potent tyrosinase-inhibitory abilities. The positional preference of cysteine residues at the N terminus in the tetrapeptides significantly contributed to their tyrosinase-inhibitory function. The sulfur atom in cysteine moieties of N-and C-terminal cysteine-containing tetrapeptides coordinated with copper ions, which then tightly blocked substrate-binding sites. N-and C-terminal tyrosinecontaining tetrapeptides functioned as competitive inhibitors against mushroom tyrosinase by using the phenol ring of tyrosine to stack with the imidazole ring of His263, thus competing for the substrate-binding site. The N-terminal cysteine-containing tetrapeptide CRVI exhibited the strongest tyrosinase-inhibitory potency (with an IC 50 of 2.7 6 0.5 mM), which was superior to those of the known tyrosinase inhibitors (arbutin and kojic acid) and outperformed kojic acid-tripeptides, mimosine-FFY, and shortsequence oligopeptides at inhibiting mushroom tyrosinase.

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“…The tyrosinase inhibitory activity of S. plebeia was measured using a modified method (36). In brief, a mixture of sodium phosphate buffer (pH 6.8; 0.066 M), L-3,4-dihydroxyphenylalanine (1.5 mM) and DMSO (10 mg/ml) was added to the enzyme solution (500 U/ml), and the mixture was incubated at 30°C for 10 min.…”

Section: Methodsmentioning

confidence: 99%

Inhibitory effect of Salvia plebeia leaf extract on ultraviolet-induced photoaging-associated ion channels and enzymes

Chang

Lee

Nam

et al. 2017

Experimental and Therapeutic Medicine

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Abstract. In traditional Korean/Asian medicine, Salvia plebeia R.Br. (S. plebeia) leaves are used to treat inflammatory diseases, including dermatitis, cough, asthma and toothache. Recently, S. plebeia leaves have been applied in skin care, as they promote skin lightening and elasticity. Therefore, the present study investigated the anti-aging effects of S. plebeia leaf methanolic extract and its fractions (dichloromethane, ethylacetate and n-butanol). The results of a whole-cell patch clamp analysis indicated that the methanolic extract mediated ultraviolet (UV)-induced photoaging-associated ion channels, transient receptor potential vanilloid 1 (TRPV1) and calcium release-activated calcium channel protein 1 (ORAI1) channel activity in HEK293T cells overexpressing TRPV1 or ORAI1 and STIM1. Electrophysiological analysis revealed that the butanol fraction inhibited capsaicin-induced TRPV1 (84±8% at -60 mV/86±1% at 100 mV at 100 µg/ml) and ORAI1 (87±2% at -120 mV at 100 µg/ml) currents. Furthermore, the dichloromethane and hexane fractions inhibited tyrosinase activity by 32.4±0.69 and 22.6±0.96% at 330 µg/ml, respectively. Furthermore, the ethylacetate and butanol fractions inhibited elastase activity by 65.2±1.30 and 31.7±1.23% at 330 µg/ml, respectively. Tyrosinase and elastase, which are UV-induced photoaging-associated enzymes, regulate skin pigmentation and wrinkle formation, respectively. The results of the present study indicated that S. plebeia leaves may be a novel treatment for UV-induced photoaging. IntroductionThe elderly population is rapidly growing, which has led to an increase in dermatological problems, including eczema, wrinkling and pigmentation. Skin aging is associated with several factors, including genetics, environment, hormonal changes and metabolic processes. Although all of these factors can contribute to skin aging, the environment, particularly solar ultraviolet (UV) radiation is a prominent mediator of skin aging (1-3). UV radiation exposure activates fibroblast and keratinocyte growth factor receptors, which activate the nuclear activator protein (AP)-1. This produces matrix metalloproteinases (MMPs), including collagenase (MMP-1), gelatinase B (MMP-9) and stromelysin-1 (MMP-3), which degrade collagen and elastic fibers, thereby inducing skin wrinkling and laxity (4,5). Neutrophils also mediate sun-induced skin aging. Following UV radiation, neutrophils infiltrate the skin and release dermal elastase, a key elastolytic enzyme (6-8). Following skin exposure to UV radiation, the keratinocytes produce endothelins (ETs), which induce melanocyte proliferation and tyrosinase production. ORAI1, calcium release-activated calcium channel protein 1; AP-1, activate the nuclear activator protein; MMPs, metalloproteinases; MMP-1, collagenase; MMP-9, gelatinase B; ET, endothelin; STIM, stromal interaction molecule; ER, endoplasmic reticulum; PKC, calcium-dependent protein kinase C Inhibitory effect of Salvia plebeia leaf extract on ultraviolet-induced photoaging-associated ion channels and enzymes

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Synthesis and evaluation of bibenzyl glycosides as potent tyrosinase inhibitors

Cited by 32 publications

References 29 publications

Skin protective effect of guava leaves against UV‐induced melanogenesis via inhibition of ORAI1 channel and tyrosinase activity

Skin protective effect of guava leaves against UV‐induced melanogenesis via inhibition of ORAI1 channel and tyrosinase activity

Phage Display–Mediated Discovery of Novel Tyrosinase-Targeting Tetrapeptide Inhibitors Reveals the Significance of N-Terminal Preference of Cysteine Residues and Their Functional Sulfur Atom

Inhibitory effect of Salvia plebeia leaf extract on ultraviolet-induced photoaging-associated ion channels and enzymes

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