Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK

Yamauchi, Kosei; Mitsunaga, Tohru; Inagaki, Mizuho; Suzuki, Tohru

doi:10.1016/j.bmc.2014.04.053

Cited by 37 publications

(35 citation statements)

References 34 publications

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“…These differences in cell cytotoxicity between the quercetin methylethers may depend on the presence of both 4 0 and 7-methoxyl groups. These results are described in the previous published [78].…”

Section: Synthesis Of Quercetin Derivatives and The Melanogenesis Stisupporting

confidence: 86%

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 Stisupporting

confidence: 86%

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Mitsunaga

Yamauchi

2015

J Wood Sci

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“…3. For the melanogenesis activity assay for each compound, we adopted a concentration that did not show strong cytotoxicity on the B16 melanoma cells as reported in our previous paper [26]. The shapes of cells treated with 200-25 mM 3C4 0 GQ exhibited no dendrite elongation effect (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…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%

“…Western blot analysis was performed according to the previously described method [26]. B16 melanoma cells treated with the samples at 12.5-0 mM for 72 h were lysed with radioimmunoprecipitation assay (RIPA) buffer containing protease inhibitor cocktail at 0 8C for 30 min.…”

Section: Western Blot Analysismentioning

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%

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