Inhibitory effect of 2-methyl-naphtho[1,2,3-de]quinolin-8-one on melanosome transport and skin pigmentation

Park, Jong Il; Lee, Ha Yeon; Lee, Ji Eun; Myung, Cheol Hwan; Hwang, Jae Sung

doi:10.1038/srep29189

Cited by 20 publications

(18 citation statements)

References 26 publications

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“…To confirm that swertiajaponin suppresses skin pigmentation in human, we cultured a viable, three-dimensional, reconstituted human epidermis consisting of human melanocytes and keratinocytes that have been known to undergo spontaneous melanogenesis with time [ 12 ]. We pretreated the human skin model with swertiajaponin for 1 h and cultured it in the maintenance medium for 5 d. Compared to the day 1, the human skin model was darkened at day 5 and swertiajaponin treatment prevented it in a concentration-dependent manner (Figure 3A-3B ).…”

Section: Resultsmentioning

confidence: 99%

Swertiajaponin inhibits skin pigmentation by dual mechanisms to suppress tyrosinase

et al. 2017

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Many skin-whitening compounds target tyrosinase because it catalyzes two rate-limiting steps in melanin synthesis. Although many tyrosinase inhibitors are currently available for a skin–whitening purpose, undesirable adverse effects are also reported. Thus, numerous efforts have been made to develop safer tyrosinase inhibitors from natural products. In line with this, we tested fifty flavonoids, a group of naturally occurring antioxidants and metal chelators, and screened swertiajaponin as the strongest tyrosinase inhibitor in cell-free experiments. Swertiajaponin did not show cytotoxicity in B16F10, HaCat, and Hs27 cells and exhibited strong anti oxidative activity in experiments using the cell-free system and B16F10 cells. It markedly inhibited αMSH- or UVB-induced melanin accumulation in B16F10 cells and suppressed skin pigmentation in a human skin model. As underlying mechanisms, in silico and Lineweaver-Burk plot analyses exhibited that swertiajaponin may directly bind to and inhibit tyrosinase activity by forming multiple hydrogen bonds and hydrophobic interactions with the binding pocket of tyrosinase. In addition, western blotting results indicated that swertiajaponin inhibited oxidative stress-mediated MAPK/MITF signaling, leading to decrease in tyrosinase protein level. Together, swertiajaponin suppresses melanin accumulation by inhibiting both activity and protein expression levels of tyrosinase. Thus, it would be a novel additive for whitening cosmetics.

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Section: Resultsmentioning

confidence: 99%

Swertiajaponin inhibits skin pigmentation by dual mechanisms to suppress tyrosinase

et al. 2017

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“…To further confirm that BMN11 suppresses melanogenesis in human, we cultured a viable, reconstituted, three dimensional human epidermis consisting of human melanocytes and keratinocytes (Neoderm ® -ME, Tegoscience Co) that has been shown to undergo spontaneous melanogenesis with time [ 20 ]. The human skin model was treated with BMN11 and cultured in the maintenance media (Tegoscience Co) for 5 d. Compared with the day 1, the color of the human skin model was darkened at day 5 and BMN11 treatment brightened it (Figure 7a ).…”

Section: Resultsmentioning

confidence: 99%

2-(3, 4-dihydroxybenzylidene)malononitrile as a novel anti-melanogenic compound

et al. 2017

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Tyrosinase is a key player in ultraviolet-induced melanogenesis. Because excessive melanin accumulation in the skin can induce hyperpigmentation, the development of tyrosinase inhibitors has attracted attention in cosmetic-related fields. However, side effects including toxicity and low selectivity have limited the use of many tyrosinase inhibitors in cosmetics. We synthesized 12 novel 2-(substituted benzylidene)malononitrile derivatives and investigated their anti-melanogenic activities. Of these 12 compounds, 2-(3, 4-dihydroxy benzylidene)malononitrile (BMN11) exhibited the strongest inhibitory activity against tyrosinase (IC 50 = 17.05 μM). In parallel with this, BMN11 treatment notably decreased alpha-melanocytestimulating hormone-induced melanin accumulation in B16F10, cells without toxicity and also decreased melanin accumulation in a human skin model. As a mechanism underlying the BMN11-mediated anti-melanogenic effect, docking simulation showed that BMN11 can directly bind to tyrosinase by forming two hydrogen bonds with GLY281 and ASN260 residues, and via three hydrophobic interactions with VAL283, PHE264, and ALA286 residues in the tyrosinase binding pocket, and this likely contributes to its inhibitory effect on tyrosinase. Consistently, Lineweaver-Burk and Cornish-Bowden plots showed that BMN11 is a competitive inhibitor of tyrosinase. We concluded that BMN11 may be a novel tyrosinase inhibitor that could be used in cosmetics.

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“…Oxidative stress, which causes various undesirable effects in the living body, is considered a major casual factor for aging and aging-related disease, and antioxidant substances such as vitamin C or a vitamin E are known to reduce such harmful effects. As the antioxidant ability of carotenoids is well known and believed to be beneficial for a healthy life, it is likely that our formula (AP-BF02) consisting of CPE and vitamin C possesses the potential to improve the quality of life through the alleviation of skin pigmentation as an antioxidant agent [16,17]. Another component of AP-BF02 is L-cystine, a dimer of cysteine.…”

Section: Subjective Efficacymentioning

confidence: 99%

Effect of Oral Intake of A Mixture Containing Natural Citrus Peel Extract, Vitamin C, and L-Cystine on Skin Brightness in Healthy Women

Kim¹,

Park²,

Hwang³

et al. 2018

JFNR

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Citrus peel extract (CPE) has several bioactivities that encompass anti-oxidation, anti-inflammation and anti-melanogenic effect. However, its usage in functional food has been difficult due to uncommon evidence in human trial. The reason of this study is to evaluate the safety and skin brightening effects of natural CPE in human subjects. To enhance its effectiveness in clinical trial, we also used both vitamin C for anti-oxidation and L-cystine for decreasing melanin biosynthesis. All subjects administered 1 test capsule (AP-BF02 including 100mg of CPE, 125mg of vitamin C, 60mg of L-cystine) or placebo for two months. We objectively measured changes in melanin index (MI), skin lightness (L*), and skin color (ITA O). The two investigators also used subjective ratings to analyze skin pigmentation. The MI values were significantly lower in test group, compared with that in placebo group from 4 weeks after. In addition, AP-BF02-intake group had significant improvement in lightness and color at the end of examine period. Consequently, oral supplementation with AP-BF02 can brighten human skin in healthy women without adverse effect.

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Inhibitory effect of 2-methyl-naphtho[1,2,3-de]quinolin-8-one on melanosome transport and skin pigmentation

Cited by 20 publications

References 26 publications

Swertiajaponin inhibits skin pigmentation by dual mechanisms to suppress tyrosinase

Swertiajaponin inhibits skin pigmentation by dual mechanisms to suppress tyrosinase

2-(3, 4-dihydroxybenzylidene)malononitrile as a novel anti-melanogenic compound

Effect of Oral Intake of A Mixture Containing Natural Citrus Peel Extract, Vitamin C, and L-Cystine on Skin Brightness in Healthy Women

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