Skip to main content

Advertisement

SpringerLink
Log in

Effects of the isoflavone puerarin and its glycosides on melanogenesis in B16 melanocytes

  • Original Paper
  • Published:
European Food Research and Technology Aims and scope Submit manuscript

Abstract

We investigated the effects of puerarin (8-C-glucosyl-7,4′-dihydroxy isoflavone), an isoflavone found in Kudzu roots (Pueraria lobata), and its glycosides (enzymatically synthesised, water-soluble derivatives of puerarin) on melanogenesis in vitro. Puerarin and its glycosides reduced mushroom tyrosinase activity by 88 and 67% at 4.8 mM, respectively, in a concentration-dependent manner. The puerarin glycosides were less effective than puerarin at the same concentration but showed a comparable inhibitory effect at a concentration at which puerarin is insoluble in water. In cultured B16 melanocytes, the melanin content was reduced significantly; moreover, tyrosinase activity was inhibited significantly by both puerarin and its glycosides when added at a concentration of 480 μM. DNA microarray and RT-PCR analyses showed significant downregulation of the expression of microphthalmia-associated transcription factor (MITF) and its target genes. The protein expression of MITF and tyrosinase was also downregulated significantly by 40 and 50%, respectively. Our findings suggest that puerarin and its glycosides cause hypopigmentation via dual mechanisms: by inhibiting tyrosinase activity directly and by altering the expression of melanogenesis-related genes, such as MITF and tyrosinase. Therefore, puerarin and its glycosides may have potential for the development of functional cosmetics causing hypopigmentation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Costin GE, Hearing VJ (2007) Human skin pigmentation: melanocytes modulate skin color in response to stress. FASEB J 21:976–994

    Article  CAS  Google Scholar 

  2. Iwata M, Corn T, Iwata S, Everett MA, Fuller BB (1990) The relationship between tyrosinase activity and skin color in human foreskins. J Invest Dermatol 95:9–15

    Article  CAS  Google Scholar 

  3. del Marmol V, Beermann F (1996) Tyrosinase and related proteins in mammalian pigmentation. FEBS Lett 381:165–168

    Article  CAS  Google Scholar 

  4. Hearing VJ, Jimenez M (1987) Mammalian tyrosinase–the critical regulatory control point in melanocyte pigmentation. Int J Biochem 19:1141–1147

    Article  CAS  Google Scholar 

  5. Yokoyama K, Yasumoto K, Suzuki H, Shibahara S (1994) Cloning of the human dopachrome tautomerase/tyrosinase-related protein 2 gene and identification of two regulatory regions required for its pigment cell-specific expression. J Biol Chem 269:27080–27087

    CAS  Google Scholar 

  6. Kobayashi T, Urabe K, Winder A, Jimenez-Cervantes C, Imokawa G, Brewington T, Solano F, Garcia-Borron JC, Hearing VJ (1994) Tyrosinase related protein 1 (trp1) functions as a DHICA oxidase in melanin biosynthesis. EMBO J 13:5818–5825

    CAS  Google Scholar 

  7. Kaufman PB, Duke JA, Brielmann H, Boik J, Hoyt JE (1997) A comparative survey of leguminous plants as sources of the isoflavones, genistein and daidzein: implications for human nutrition and health. J Altern Complement Med 3:7–12

    Article  CAS  Google Scholar 

  8. Xiong FL, Sun XH, Gan L, Yang XL, Xu HB (2006) Puerarin protects rat pancreatic islets from damage by hydrogen peroxide. Eur J Pharmacol 529:1–7

    Article  CAS  Google Scholar 

  9. Lucas EA, Khalil DA, Daggy BP, Arjmandi BH (2001) Ethanol-extracted soy protein isolate does not modulate serum cholesterol in golden Syrian hamsters: a model of postmenopausal hypercholesterolemia. J Nutr 131:211–214

    CAS  Google Scholar 

  10. Lin RC, Li TK (1998) Effects of isoflavones on alcohol pharmacokinetics and alcohol-drinking behavior in rats. Am J Clin Nutr 68:1512S–1515S

    CAS  Google Scholar 

  11. Rezvani AH, Overstreet DH, Perfumi M, Massi M (2003) Plant derivatives in the treatment of alcohol dependency. Pharmacol Biochem Behav 75:593–606

    Article  CAS  Google Scholar 

  12. Prasain JK, Jones K, Kirk M, Wilson L, Smith-Johnson M, Weaver C, Barnes S (2003) Profiling and quantification of isoflavonoids in kudzu dietary supplements by high-performance liquid chromatography and electrospray ionization tandem mass spectrometry. J Agric Food Chem 51:4213–4218

    Article  CAS  Google Scholar 

  13. Li D, Park SH, Shim JH, Lee HS, Tang SY, Park CS, Park KH (2004) In vitro enzymatic modification of puerarin to puerarin glycosides by maltogenic amylase. Carb Res 339:2789–2797

    Article  CAS  Google Scholar 

  14. Chung MJ, Sung NJ, Park CS, Kweon DK, Mantovani A, Moon TW, Lee SJ, Park KH (2008) Antioxidative and hypocholesterolemic activities of water-soluble puerarin glycosides in hepg2 cells and in c57 bl/6j mice. Eur J Pharmacol 578:159–170

    Article  CAS  Google Scholar 

  15. Matsuda H, Nakamura S, Kubo M (1994) Studies of cuticle drugs from natural sources. II. Inhibitory effects of Prunus plants on melanin biosynthesis. Biol Pharm Bull 17:1417–1420

    CAS  Google Scholar 

  16. Tusher VG, Tibshirani R, Chu G (2001) Significance analysis of microarrays applied to the ionizing radiation response. Proc Natl Acad Sci USA 98:5116–5121

    Article  CAS  Google Scholar 

  17. AMIGO http://amigo.Geneontology.Org

  18. Mouse genome informatics http://www.informatics.jax.org

  19. UniGene database http://www.ncbi.nlm.nih.gov/unigene

  20. Ando H, Kondoh H, Ichihashi M, Hearing VJ (2007) Approaches to identify inhibitors of melanin biosynthesis via the quality control of tyrosinase. J Invest Dermatol 127:751–761

    Article  CAS  Google Scholar 

  21. Schallreuter KU (2007) Advances in melanocyte basic science research. Dermatol Clin 25:283–291, vii

    Google Scholar 

  22. Solano F, Briganti S, Picardo M, Ghanem G (2006) Hypopigmenting agents: an updated review on biological, chemical and clinical aspects. Pigment Cell Res 19:550–571

    Article  CAS  Google Scholar 

  23. Badria FA, Elgayyar MA (2001) A new type of tyrosinase inhibitors from natural products as potential treatments for hyperpigmentation. Boll Chim Farm 140:267–271

    CAS  Google Scholar 

  24. Shimizu K, Kondo R, Sakai K (2000) Inhibition of tyrosinase by flavonoids, stilbenes and related 4-substituted resorcinols: Structure-activity investigations. Planta Med 66:11–15

    Article  CAS  Google Scholar 

  25. Chang TS (2007) Two potent suicide substrates of mushroom tyrosinase: 7, 8, 4′-trihydroxyisoflavone and 5, 7, 8, 4′-tetrahydroxyisoflavone. J Agric Food Chem 55:2010–2015

    Article  CAS  Google Scholar 

  26. Chang TS, Ding HY, Lin HC (2005) Identifying 6, 7, 4′-trihydroxyisoflavone as a potent tyrosinase inhibitor. Biosci Biotechnol Biochem 69:1999–2001

    Article  CAS  Google Scholar 

  27. Schaffer JV, Bolognia JL (2001) The melanocortin-1 receptor: red hair and beyond. Arch Dermatol 137:1477–1485

    CAS  Google Scholar 

  28. Thody AJ (1999) Alpha-MSH and the regulation of melanocyte function. Ann NY Acad Sci 885:217–229

    Article  CAS  Google Scholar 

  29. Schwyzer R, Eberle A (1977) On the molecular mechanism of alpha-MSH receptor interactions. Front Horm Res 4:18–25

    CAS  Google Scholar 

  30. Goverde HJ, Pesman GJ, Smals AG (1988) The melanotropin potentiating factor and beta-endorphin do not modulate the alpha-melanotropin- or adrenocorticotropin-induced corticosteroidogenesis in purified isolated rat adrenal cells. Neuropeptides 12:125–130

    Article  CAS  Google Scholar 

  31. Huber WE, Price ER, Widlund HR, Du J, Davis IJ, Wegner M, Fisher DE (2003) A tissue-restricted camp transcriptional response: Sox10 modulates alpha-melanocyte-stimulating hormone-triggered expression of microphthalmia-associated transcription factor in melanocytes. J Biol Chem 278:45224–45230

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This study was supported by a grant from the Korea Health 21 R&D Project, Ministry of Health and Welfare, Republic of Korea (A050376), and by the Technology Development Program of the Ministry of Agriculture and Forestry (105054-03-2-HD110).

Author information

Authors and Affiliations

  1. Division of Food Bioscience and Technology, College of Life Sciences and Biotechnology, Korea University, Seoul, 136-713, South Korea

    Young-Mi Choi, Hee-jin Jun, Mi Ran Roh, Jungae Jun & Sung-Joon Lee

  2. Laboratory for High Performance Computing and Informatics, University of California, Davis MCB, One Shields Avenue, Davis, CA, 95616, USA

    Kevin Dawson & Raymond L. Rodriguez

  3. Department of Food Science and Technology, School of Agricultural Biotechnology, Center for Agricultural Biomaterials, Seoul National University, Seoul, 151-921, South Korea

    Chung-Hyo Choi, Jae-Hoon Shim & Kwan-Hwa Park

  4. Division of Bioscience and Biotechnology, Konkuk University, Seoul, 143-701, Korea

    ChoongHwan Lee

  5. Food Research Institute, Amorepacific Corporation R&D Center, Yougin, 314-1, Korea

    Sang Jun Lee

Authors
  1. Young-Mi Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hee-jin Jun
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kevin Dawson
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Raymond L. Rodriguez
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mi Ran Roh
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jungae Jun
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Chung-Hyo Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Jae-Hoon Shim
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. ChoongHwan Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Sang Jun Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Kwan-Hwa Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Sung-Joon Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sung-Joon Lee.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PPT 339 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Choi, YM., Jun, Hj., Dawson, K. et al. Effects of the isoflavone puerarin and its glycosides on melanogenesis in B16 melanocytes. Eur Food Res Technol 231, 75–83 (2010). https://doi.org/10.1007/s00217-010-1251-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00217-010-1251-5

Keywords

Search

Navigation