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Int. J. Mol. Sci. 2015, 16(12), 28598-28613; doi:10.3390/ijms161226115

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

1
Department of Internal Medicine, Heping Branch, Taipei City Hospital, Taipei 100, Taiwan
2
Graduate Institute of Pharmacognosy, College of Pharmacy, Taipei Medical University, Taipei 110, Taiwan
3
Ph.D. Program for the Clinical Drug Discovery from Botanical Herbs, College of Pharmacy, Taipei Medical University, Taipei 110, Taiwan
4
National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei 112, Taiwan
5
Center for Reproductive Medicine & Sciences, Taipei Medical University Hospital, Taipei 110, Taiwan
*
Author to whom correspondence should be addressed.
Academic Editor: Manickam Sugumaran
Received: 8 August 2015 / Revised: 18 November 2015 / Accepted: 23 November 2015 / Published: 2 December 2015
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
View Full-Text   |   Download PDF [1801 KB, uploaded 2 December 2015]   |  

Abstract

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 Km 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. View Full-Text
Keywords: 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 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
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Lin, R.-D.; Chen, M.-C.; Liu, Y.-L.; Lin, Y.-T.; Lu, M.-K.; Hsu, F.-L.; Lee, M.-H. New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes. Int. J. Mol. Sci. 2015, 16, 28598-28613.

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