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Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors

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Abstract

Anti-melanogenesis screening of 47 synthesized curcumin-like diarylpentanoid analogues was performed to show that some had a potent inhibitory effect on the melanogenesis in B16 melanoma cells. Their actions were considered to be mostly due to tyrosinase inhibition, tyrosinase expression inhibition, and melanin pigment degradation. The structure–activity relationships of those curcumin-like diarylpentanoid analogues which inhibited the melanogenesis and tyrosinase activity were also discussed. Of those compounds assayed, (2E,6E)-2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone showed the most potent anti-melanogenesis effect, the mechanism of which is considered to be the degradation of the melanin pigment in B16 melanoma cells, affecting neither the tyrosinase activity nor tyrosinase expression.

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Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan and a grant from The Open Research Center Project in Hoshi University. Authors also thank the Ministry of Science Technology and Innovation for the funds provided under the SAGA research funding program.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo, 142-8501, Japan

    Takahiro Hosoya, Asami Nakata, Fumie Yamasaki & Hiroshi Morita

  2. Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    Faridah Abas, Khozirah Shaari & Nordin Hj Lajis

  3. Department of Food Science, Faculty of Food Science and Technology, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    Faridah Abas

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  1. Takahiro Hosoya
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  2. Asami Nakata
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  3. Fumie Yamasaki
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  4. Faridah Abas
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  5. Khozirah Shaari
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  6. Nordin Hj Lajis
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  7. Hiroshi Morita
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Correspondence to Hiroshi Morita.

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Hosoya, T., Nakata, A., Yamasaki, F. et al. Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors. J Nat Med 66, 166–176 (2012). https://doi.org/10.1007/s11418-011-0568-0

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  • DOI: https://doi.org/10.1007/s11418-011-0568-0

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