New whitening constituents from taiwan-native Pyracantha koidzumii: Structures and tyrosinase inhibitory analysis in human epidermalmelanocytes

Rong Dih Lin, Mei Chuan Chen, Yan Ling Liu, Yi Tzu Lin, Mei Kuang Lu, Feng-Lin Hsu, Mei Hsien Lee

Research output: Contribution to journalArticle

7 Citations (Scopus)

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-2′-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.

Original languageEnglish
Pages (from-to)28598-28613
Number of pages16
JournalInternational Journal of Molecular Sciences
Volume16
Issue number12
DOIs
Publication statusPublished - Dec 2 2015

Fingerprint

Pyracantha
Monophenol Monooxygenase
Cosmetics
Taiwan
inhibitors
enzymes
dopa
Melanocytes
proteins
Proteins
Enzyme kinetics
Transcription factors
Substrates
Microphthalmia-Associated Transcription Factor
boxes
Assays
isolation
Skin
Skin Care
Enzymes

Keywords

  • 3,4-dihydroxy-5-methoxybiphenyl-2′-O-β-D-glucopyranoside
  • Human epidermal melanocytes
  • Microphthalmia-associated transcription factor
  • Paired box 3
  • Pyracantha koidzumii
  • Tyrosinase
  • Tyrosinase-related proteins

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Spectroscopy
  • Inorganic Chemistry
  • Catalysis
  • Molecular Biology
  • Computer Science Applications

Cite this

New whitening constituents from taiwan-native Pyracantha koidzumii : Structures and tyrosinase inhibitory analysis in human epidermalmelanocytes. / Lin, Rong Dih; Chen, Mei Chuan; Liu, Yan Ling; Lin, Yi Tzu; Lu, Mei Kuang; Hsu, Feng-Lin; Lee, Mei Hsien.

In: International Journal of Molecular Sciences, Vol. 16, No. 12, 02.12.2015, p. 28598-28613.

Research output: Contribution to journalArticle

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title = "New whitening constituents from taiwan-native Pyracantha koidzumii: Structures and tyrosinase inhibitory analysis in human epidermalmelanocytes",
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-2′-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.",
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AU - Liu, Yan Ling

AU - Lin, Yi Tzu

AU - Lu, Mei Kuang

AU - Hsu, Feng-Lin

AU - Lee, Mei Hsien

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AB - 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-2′-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.

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