Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells

Yamauchi, Kosei; Mitsunaga, Tohru; Batubara, Irmanida

doi:10.1016/j.bmc.2013.12.062

Cited by 35 publications

(36 citation statements)

References 21 publications

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“…The data for cell viability and the melanogenesis activity of B16 melanoma cells are shown in Table 1. Quercetin glycosides 1, 3, and 4 showed intracellular melanogenesis stimulatory activity in a dose-dependent manner, and their activities were higher than that of theophyline used as positive control [76]. Interestingly, the other quercetin glycosides had little or no melanogenesis stimulatory activity despite their structural similarities.…”

Section: Synthesis Of Quercetin Derivatives and The Melanogenesis Stimentioning

confidence: 97%

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Mitsunaga

Yamauchi

2015

J Wood Sci

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Controlling melanogenesis is important for maintaining the good health and cosmetic appearance of a human body. This study aims to search the active compounds from natural products exhibiting the melanogenesis modulating activity and elucidate the mechanism underlying the observed activity. Two novel quercetin glycosideswere isolated and identified from Helminthostachys zeylanica roots 50 % ethanol extract. Compound 1 exhibited intracellular melanogenesis stimulatory activity, while 2 showed no effect even the structural similarity. To understand the structure-activity relationships, twelve quercetin glycosides and seven methylquercetins were synthesized from rutin as starting material. As the result of bioassay using synthesized nineteen quercetin derivatives in B16 melanoma cells, some quercetin-3-O-b-D-glucopyranosides stimulated the intracellular melanogenesis. On the other hand, synthesized 3-O-methylquercetin 12 and 3,4 0 ,7-Otrimethylquercetin 15 increased both intra and extracellular melanin contents with no cytotoxicity. Compoud 15 increased the phosphorylated p38 mitogen-activated protein kinase (MAPK) and microphthalmia-associated transcription factor (MITF) which regulates the expression of tyrosinase, TRP-1 and TRP-2. While 12 enhanced the expression of the melanogenic enzymes without involving the MITF, as evidenced by its lack of any stimulation of the expression of MITF and p-p38 MAPK. This result indicates that 12 may stimulate the expression of tyrosinase, TRP-1, and TRP-2 by stimulating currently unidentified transcriptional factors and/or by regulating the degradation of melanogenic enzymes.

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Section: Synthesis Of Quercetin Derivatives and The Melanogenesis Stimentioning

confidence: 97%

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Mitsunaga

Yamauchi

2015

J Wood Sci

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“…Quercetin derivatives 3C4 0 GQ, 3MQ, and 34 0 7TMQ were synthesized using the methods presented in our previous publication [25,26].…”

Section: Synthesis Of 3c4 0 Gq 3mq and 34 0 7tmqmentioning

confidence: 99%

“…1, was isolated from Helminthostachys zeylanica root extract as an intracellular melanogenesis stimulator [24]. 34 0 7TMQ and other distinct quercetin derivatives were synthesized in order to understand the structure-activity relationship of quercetin derivatives in our previous report [25,26]. Among the synthesized compounds, 3-O-methylquercetin (3MQ) and 3,4 0 ,7-O-trimethylquercetin (34 0 7TMQ) ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Quercetin derivatives regulate melanosome transportation via EPI64 inhibition and elongate the cell shape of B16 melanoma cells

Yamauchi

Mitsunaga

Inagaki

et al. 2015

Biomedicine & Pharmacotherapy

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“…Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-β-d-glucopyranoside quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside, and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect [15]. Ali et al [16] have also determined the ability of berberine, a principal active ingredient present in the roots of the herb Berberis vulgaris, to stimulate pigment dispersion in the isolated skin melanophores of the toad Bufo melanostictus.…”

Section: Effect Of Herbal Extract and Their Actives On Melanogenesismentioning

confidence: 99%

Natural Melanogenesis Stimulator a Potential Tool for the Treatment of Hypopigmentation Disease

Zaidi¹

2017

IJMBOA

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The synthesis of melanin pigments or melanogenesis has many important physiological functions that include photo protection of the human skin from ultraviolet (UV) irradiation. Melanogenesis is a complex pathway involving melanin synthesis, melanin transport, and melanosome release. Melanin synthesis is stimulated by various effects such as α-melanocyte-stimulating hormone (α-MSH); cyclic AMP (cAMP) elevating agents including palmitic acid, methyl ester, psoralen, thymoquinone, piperine, berberine and withaferin-A. Loss of the hair shaft melanin is associated with decrease of tyrosinase activity in the bulb of melanocytes. Activators of tyrosinase with stimulatory effects on melanogenesis are beneficial for the treatment of hypopigmentation diseases. This is only report authors found in literature about tyrosinase activation. Melanogenesis stimulator are rarely studied as most industries are more interested on inhibitors of the enzyme in order to reduce the adverse effects of melanin formation in, for example, processed food and human skin. Hence, there is a need to review the successful utilization of tyrosinase stimulators from natural herbs for medicinal applications.

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Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells

Cited by 35 publications

References 21 publications

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Quercetin derivatives regulate melanosome transportation via EPI64 inhibition and elongate the cell shape of B16 melanoma cells

Natural Melanogenesis Stimulator a Potential Tool for the Treatment of Hypopigmentation Disease

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