New constituent from Podocarpus macrophyllus var. macrophyllus shows anti-tyrosinase effect and regulates tyrosinase-related proteins and mRNA in human epidermal melanocytes

Kur Ta Cheng, Feng Lin Hsu, Shih Hui Chen, Peng Ke Hsieh, Hsu Shan Huang, Ching Kuo Lee, Mei Hsien Lee

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A new biflavonoid, 2,3-dihydro-4′,4‴-di-O-methylamentoflavone (5), and five known compounds, (-)-catechin (1), quercetin (2), 2,3-dihydrosciadopitysin (3), sciadopitysin (4), and isoginkgetin (6), were isolated from Podocarpus macrophyllus var. macrophyllus (Podocarpaceae). These compounds were evaluated their ability to inhibit cellular tyrosinase activity and for their melanin inhibitory activity in human epidermal melanocytes (HEMn). In the melanin synthesis assay, 2,3-dihydro-4′,4‴-di-O- methylamentoflavone (5) showed a potent anti-tyrosinase effect with IC 50=0.098 mM in HEMn. It also significantly decreased both protein and mRNA levels of the tyrosinase-related protein-2 (TRP-2) by Western blot and quantitative real-time PCR (qRT-PCR) analysis. These findings suggest that the new compound, 2,3-dihydro-4′,4‴-di-O-methylamentoflavone (5), is the most active component of P. macrophyllus var. macrophyllus in inhibiting pigmentation and that this inhibition is exerted through inhibition of transcription of the genes encoding TRP2.

Original languageEnglish
Pages (from-to)757-761
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume55
Issue number5
DOIs
Publication statusPublished - May 2007

Fingerprint

Monophenol Monooxygenase
Melanocytes
Melanins
Biflavonoids
Messenger RNA
Gene encoding
Catechin
Quercetin
Pigmentation
Transcription
Human Activities
Real-Time Polymerase Chain Reaction
Assays
Proteins
Western Blotting
Genes
isoginkgetin
sciadopitysin
dopachrome isomerase

Keywords

  • 2,3-dihydro-4′,4‴-di-O-methylamentoflavone
  • Human epidermal melanocyte
  • Quantitative real-time PCR
  • Tyrosinase
  • Tyrosinase-related protein-2

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

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title = "New constituent from Podocarpus macrophyllus var. macrophyllus shows anti-tyrosinase effect and regulates tyrosinase-related proteins and mRNA in human epidermal melanocytes",
abstract = "A new biflavonoid, 2,3-dihydro-4′,4‴-di-O-methylamentoflavone (5), and five known compounds, (-)-catechin (1), quercetin (2), 2,3-dihydrosciadopitysin (3), sciadopitysin (4), and isoginkgetin (6), were isolated from Podocarpus macrophyllus var. macrophyllus (Podocarpaceae). These compounds were evaluated their ability to inhibit cellular tyrosinase activity and for their melanin inhibitory activity in human epidermal melanocytes (HEMn). In the melanin synthesis assay, 2,3-dihydro-4′,4‴-di-O- methylamentoflavone (5) showed a potent anti-tyrosinase effect with IC 50=0.098 mM in HEMn. It also significantly decreased both protein and mRNA levels of the tyrosinase-related protein-2 (TRP-2) by Western blot and quantitative real-time PCR (qRT-PCR) analysis. These findings suggest that the new compound, 2,3-dihydro-4′,4‴-di-O-methylamentoflavone (5), is the most active component of P. macrophyllus var. macrophyllus in inhibiting pigmentation and that this inhibition is exerted through inhibition of transcription of the genes encoding TRP2.",
keywords = "2,3-dihydro-4′,4‴-di-O-methylamentoflavone, Human epidermal melanocyte, Quantitative real-time PCR, Tyrosinase, Tyrosinase-related protein-2",
author = "Cheng, {Kur Ta} and Hsu, {Feng Lin} and Chen, {Shih Hui} and Hsieh, {Peng Ke} and Huang, {Hsu Shan} and Lee, {Ching Kuo} and Lee, {Mei Hsien}",
year = "2007",
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T1 - New constituent from Podocarpus macrophyllus var. macrophyllus shows anti-tyrosinase effect and regulates tyrosinase-related proteins and mRNA in human epidermal melanocytes

AU - Cheng, Kur Ta

AU - Hsu, Feng Lin

AU - Chen, Shih Hui

AU - Hsieh, Peng Ke

AU - Huang, Hsu Shan

AU - Lee, Ching Kuo

AU - Lee, Mei Hsien

PY - 2007/5

Y1 - 2007/5

N2 - A new biflavonoid, 2,3-dihydro-4′,4‴-di-O-methylamentoflavone (5), and five known compounds, (-)-catechin (1), quercetin (2), 2,3-dihydrosciadopitysin (3), sciadopitysin (4), and isoginkgetin (6), were isolated from Podocarpus macrophyllus var. macrophyllus (Podocarpaceae). These compounds were evaluated their ability to inhibit cellular tyrosinase activity and for their melanin inhibitory activity in human epidermal melanocytes (HEMn). In the melanin synthesis assay, 2,3-dihydro-4′,4‴-di-O- methylamentoflavone (5) showed a potent anti-tyrosinase effect with IC 50=0.098 mM in HEMn. It also significantly decreased both protein and mRNA levels of the tyrosinase-related protein-2 (TRP-2) by Western blot and quantitative real-time PCR (qRT-PCR) analysis. These findings suggest that the new compound, 2,3-dihydro-4′,4‴-di-O-methylamentoflavone (5), is the most active component of P. macrophyllus var. macrophyllus in inhibiting pigmentation and that this inhibition is exerted through inhibition of transcription of the genes encoding TRP2.

AB - A new biflavonoid, 2,3-dihydro-4′,4‴-di-O-methylamentoflavone (5), and five known compounds, (-)-catechin (1), quercetin (2), 2,3-dihydrosciadopitysin (3), sciadopitysin (4), and isoginkgetin (6), were isolated from Podocarpus macrophyllus var. macrophyllus (Podocarpaceae). These compounds were evaluated their ability to inhibit cellular tyrosinase activity and for their melanin inhibitory activity in human epidermal melanocytes (HEMn). In the melanin synthesis assay, 2,3-dihydro-4′,4‴-di-O- methylamentoflavone (5) showed a potent anti-tyrosinase effect with IC 50=0.098 mM in HEMn. It also significantly decreased both protein and mRNA levels of the tyrosinase-related protein-2 (TRP-2) by Western blot and quantitative real-time PCR (qRT-PCR) analysis. These findings suggest that the new compound, 2,3-dihydro-4′,4‴-di-O-methylamentoflavone (5), is the most active component of P. macrophyllus var. macrophyllus in inhibiting pigmentation and that this inhibition is exerted through inhibition of transcription of the genes encoding TRP2.

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