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http://dx.doi.org/10.14478/ace.2020.1078

Synthesis and Biological Evaluation of Water-Soluble Oleanolic Acid Derivatives for use as Melanogenesis Inhibitors  

An, Hyun-Jin (Department of Engineering Chemistry, Chungbuk National University)
Yoon, Young-kyung (Yeomyung Biochem Co., Ltd.)
Lee, Jae-Duck (Yeomyung Biochem Co., Ltd.)
Jeong, Noh-Hee (Department of Engineering Chemistry, Chungbuk National University)
Publication Information
Applied Chemistry for Engineering / v.31, no.6, 2020 , pp. 653-659 More about this Journal
Abstract
This study was focused on the synthesis of methoxy polyethylene glycol-oleanolic acid ester (mPEG-OA derivative) and investigation of its water solubility and anti-melanogenic effects. mPEG-OA derivative was identified by 1H and 13C NMR and FT-IR spectroscopic measurements. The water solubilities of mPEG-OA derivative and OA were found to be 13 and 0.013 mg/mL and that of mPEG-OA was found to be 1000-fold higher than that of OA. The effects of mPEG-OA derivative and OA on cell viability were measured using B16F10 melanoma cells. The viability of cells treated with mPEG-OA derivative (250 μM) increased 4-fold compared to that of cells treated with OA (62.5 μM). At mPEG-OA derivative and OA concentrations where the cell viability was unaffected, the inhibitory effect of mPEG-OA derivative and OA on the melanogenesis in B16F10 melanoma cells were 36 and 35% at 50 and 10 μM, respectively. The expression level of microphthalmia-associated transcription (MITF) was also reduced in B16F10 melanoma cells treated with mPEG-OA and OA. Overall, mPEG-OA derivative showed excellent water solubility and inhibitory effects of the melanogenesis, which could be used as a potential formulation for use in whitening functional cosmetic material.
Keywords
Oleanolic acid; Water solubility; Pegylation; Melanogenesis; Cosmetics material;
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