New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes

International Journal of Molecular Sciences

Rong-Dih Lin¹  Mei-Chuan Chen²  Yan-Ling Liu²  Yi-Tzu Lin²  Mei-Kuang Lu³  Feng-Lin Hsu²  Mei-Hsien Lee² 

[1] Department of Internal Medicine, Heping Branch, Taipei City Hospital, Taipei 100, Taiwan;Graduate Institute of Pharmacognosy, College of Pharmacy, Taipei Medical University, Taipei 110, Taiwan;National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei 112, Taiwan;

关键词: Pyracantha koidzumii;    3;    4-dihydroxy-5-methoxybiphenyl-2′-O-β-d-glucopyranoside;    human epidermal melanocytes;    tyrosinase;    tyrosinase-related proteins;    Paired box 3;    microphthalmia-associated transcription factor;   

DOI  :  10.3390/ijms161226115

来源: mdpi

【 摘 要 】

Nontoxic natural products useful in skin care cosmetics are of considerable interest. Tyrosinase is a rate-limiting enzyme for which its inhibitor is useful in developing whitening cosmetics. Pyracantha koidzumii (Hayata) Rehder is an endemic species in Taiwan that exhibits tyrosinase-inhibitory activity. To find new active natural compounds from P. koidzumii, we performed bioguided isolation and studied the related activity in human epidermal melanocytes. In total, 13 compounds were identified from P. koidzumii in the present study, including two new compounds, 3,6-dihydroxy-2,4-dimethoxy-dibenzofuran (9) and 3,4-dihydroxy-5-methoxybiphenyl-2ʹ-O-β-d-glucopyranoside (13), as well as 11 known compounds. The new compound 13 exhibited maximum potency in inhibiting cellular tyrosinase activity, the protein expression of cellular tyrosinase and tyrosinase-related protein-2, as well as the mRNA expression of Paired box 3 and microphthalmia-associated transcription factor in a concentration-dependent manner. In the enzyme kinetic assay, the new compound 13 acted as an uncompetitive mixed-type inhibitor against the substrate l-3,4-dihydroxyphenylalanine and had a K_m value against this substrate of 0.262 mM, as calculated using the Lineweaver–Burk plots. Taken together, our findings show compound 13 exhibits tyrosinase inhibition in human melanocytes and compound 13 may be a potential candidate for use in cosmetics.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.