Skip to main content
Log in

Melanin biosynthesis inhibitory effects of calycosin-7-O-β-d-glucoside isolated from astragalus (Astragalus membranaceus)

  • Research Article
  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

Abstract

To discover an active skin depigmentation agent, we isolated a melanin biosynthesis inhibitor from the methanol extract of astragalus (Astragalus membranaceus) using a bioactivity-guided fractionation and identified it as calycosin-7-O-β-d-glucoside via spectroscopic analysis. The active compound exhibited tyrosinase inhibitory activity with an IC50 value of 68 μM. In addition, calycosin-7-O-β-d-glucoside showed a melanin biosynthesis inhibition zone in a culture plate of Streptomyces bikiniensis. Furthermore, 75.78 μM of calycosin-7-O-β-d-glucoside dramatically decreased 50% of the melanin content on Melan-a cells without any apparent cytotoxicity. Theses results indicate that the calycosin-7-O-β-d-glucoside isolated from astragalus may be a good candidate for skin-whitening agent.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Kumar KJ, Yang JC, Chu FH, Chang ST, Wang SY. Lucidone, a novel melanin inhibitor from the fruit of Lindera erythrocarpa Makino. Phytother. Res. 24: 1158–1165 (2010)

    CAS  Google Scholar 

  2. Zhang X, Hu XA, Hou A, Wang H. Inhibitory effect of 2,4,2′,4′-tetrahydroxy-3-(3-methyl-2-butenyl)-chalcone on tyrosinase activity and melanin biosynthesis. Biol. Pharm. Bull. 32: 86–90 (2009)

    Article  CAS  Google Scholar 

  3. Heo SJ, Ko SC, Cha SH, Kang DH, Park HS, Choi YU, Kim D, Jung WK, Jeon J. Effect of phlorotannins isolated from Ecklonia cava on melanogenesis and their protective effect against photooxidative stress induced by UV-B radiation. Toxicol. In Vitro 23: 1123–1130 (2009)

    Article  CAS  Google Scholar 

  4. Luo LH, Kim HJ, Nguyen DH, Lee HB. Lee NH, Kim EK. Depigmentation of melanocytes by (2Z,8Z)-matricaria acid methyl ester isolated from Erigeron breviscapus. Biol. Pharm. Bull. 32: 1091–1094 (2009)

    Article  CAS  Google Scholar 

  5. Wakamatsu K, Kavanagh RA, Kadekaro AL, Terzieva S, Sturm RA, Leachman S, Abdel-Malek Z, Ito S. Diversity of pigmentation in cultured human melanocytes is due to differences in the type as well as quantity of melanin. Pigm. Cell Res. 19: 154–162 (2006)

    Article  CAS  Google Scholar 

  6. Briganti S, Camera E, Picardo M. Chemical and instrumental approaches to treat hyperpigmentation. Pigm. Cell Res. 16: 101–110 (2003)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  8. Sato K, Toriyama M. Effect of pyrroloquinoline quinone (PQQ) on melanogenic protein expression in murine B16 melanoma. J. Dermatol. Sci. 53: 140–145 (2009)

    Article  CAS  Google Scholar 

  9. Karioti A, Protopappa A, Megoulas N, Skaltsa H. Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum. Bioorg. Med. Chem. 15: 2708–2714 (2007)

    Article  CAS  Google Scholar 

  10. Fujii T, Saito M. Inhibitory effect of quercetin isolated from rose hip (Rosa canina L.) against melanogenesis by mouse melanoma cells. Biosci. Biotech. Bioch. 73: 1989–1993 (2009)

    Article  CAS  Google Scholar 

  11. Kim YJ, Uyama H. Tyrosinase inhibitors from natural and synthetic sources: Structure, inhibition mechanism, and perspective for the future. Cell Mol. Life Sci. 62: 1707–1723 (2005)

    Article  CAS  Google Scholar 

  12. Marongiu B, Piras A, Porcedda S, Tuveri E, Sanjust E, Meli M, Sollai F, Zucca P, Rescigno A. Supercritical CO2 extract of Cinnamomum zeylanicum: Chemical characterization and antityrosinase activity. J. Agr. Food Chem. 55: 10022–10027 (2007)

    Article  CAS  Google Scholar 

  13. Cabanes J, Chazarra S, Garcia-Carmona F. Kojic acid, a cosmetic skin whitening agent, is a slow-binding inhibitor of catecholase activity of tyrosinase. J. Pharm. Pharmacol. 46: 982–985 (1994)

    Article  CAS  Google Scholar 

  14. Maeda K, Fukuda M. Arbutin: Mechanism of its depigmenting action in human melanocyte culture. J. Pharmacol. Exp. Ther. 276: 765–769 (1996)

    CAS  Google Scholar 

  15. Shimogaki H, Tanaka Y, Tamai H, Masuda M. In vitro and in vivo evaluation of ellagic acid on melanogenesis inhibition. Int. J. Cosmetic Sci. 22: 291–303 (2000)

    Article  CAS  Google Scholar 

  16. Curto EV, Kwong C, Hermersdorfer H, Glatt H, Santis C, Virador V, Hearing VJ, Dooley TP. Inhibitors of mammalian melanocyte tyrosinase: In vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors. Biochem. Pharmacol. 57: 663–672 (1999)

    Article  CAS  Google Scholar 

  17. Penney KB, Smith CJ, Allen JC. Depigmenting action of hydroquinone depends on disruption of fundamental cell processes. J. Invest. Dermatol. 82: 308–310 (1984)

    Article  CAS  Google Scholar 

  18. Zhong S, Wu Y, Soo-Mi A, Zhao J, Wang K, Yang S, Jae-Ho Y, Zhu X. Depigmentation of melanocytes by the treatment of extracts from traditional Chinese herbs: A cell culture assay. Biol. Pharm. Bull. 29: 1947–1951 (2006)

    Article  CAS  Google Scholar 

  19. Auyeung KK, Cho CH, Ko JK. A novel anticancer effect of Astragalus saponins: Transcriptional activation of NSAID-activated gene. Int. J. Cancer 125: 1082–1091 (2009)

    Article  CAS  Google Scholar 

  20. Mao XQ, Yu F, Wang N, Wu Y, Zou F, Wu K, Liu M, Ouyang JP. Hypoglycemic effect of polysaccharide enriched extract of Astragalus membranaceus in diet induced insulin resistant C57BL/ 6J mice and its potential mechanism. Phytomedicine 16: 416–425 (2009)

    Article  CAS  Google Scholar 

  21. Ryu M, Kim EH, Chun M, Kang S, Shim B, Yu YB, Jeong GJ, Lee JS. Astragali Radix elicits anti-inflammation via activation of MKP-1, concomitant with attenuation of p38 and Erk. J. Ethnopharmacol. 115: 184–193 (2008)

    Article  CAS  Google Scholar 

  22. Song Y, Li P, Wang D, Cheng YY. Micellar electrokinetic chromatography for the quantitative analysis of flavonoids in the radix of Astragalus membranaceus var. mongholicus. Planta Med. 74: 84–89 (2008)

    Article  CAS  Google Scholar 

  23. Zhang WD, Chen H, Zhang C, Liu RH, Li HL, Chen HZ. Astragaloside IV from Astragalus membranaceus shows cardioprotection during myocardial ischemia in vivo and in vitro. Planta Med. 72: 4–8 (2006)

    Article  CAS  Google Scholar 

  24. Zhu H, Zhang Y, Ye G, Li Z, Zhou P, Huang C. In vivo and in vitro antiviral activities of calycosin-7-O-β-d-glucopyranoside against coxsackie virus B3. Biol. Pharm. Bull. 32: 68–73 (2009)

    Article  CAS  Google Scholar 

  25. Kim JH, Baek SH, Kim DH, Choi TY, Yoon TJ, Hwang JS, Kim MR, Kwon HJ, Lee CH. Downregulation of melanin synthesis by haginin A and its application to in vivo lightening model. J. Invest. Dermatol. 128: 1227–1235 (2008)

    Article  CAS  Google Scholar 

  26. Lee CH, Chung MC, Lee HJ, Bae KS, Kho YH. MR566A and MR566B, new melanin synthesis inhibitors produced by Trichoderma harzianum. I. Taxonomy, fermentation, isolation, and biological activities. J. Antibiot. 50: 469–473 (1997)

    CAS  Google Scholar 

  27. Bennett DC, Cooper PJ, Hart IR. A line of non-tumorigenic mouse melanocytes, syngeneic with the B16 melanoma and requiring a tumour promoter for growth. Int. J. Cancer 39: 414–418 (1987)

    Article  CAS  Google Scholar 

  28. Du X, Bai Y, Liang H, Wang Z, Zhao Y, Zhang Q, Huang L. Solvent effect in 1H NMR spectra of 3′-hydroxy-4′-methoxy isoflavonoids from Astragalus membranaceus var. mongholicus. Magn. Reson. Chem. 44: 708–712 (2006)

    Article  CAS  Google Scholar 

  29. Yu DH, Bao YM, An LJ, Yang M. Protection of PC12 cells against superoxide-induced damage by isoflavonoids from Astragalus mongholicus. Biomed. Environ. Sci. 22: 50–54 (2009)

    Article  CAS  Google Scholar 

  30. Zhang LJ, Liu HK, Hsiao PC, Kuo LM, Lee IJ, Wu TS, Chiou WF, Kuo YH. New isoflavonoid glycosides and related constituents from Astragali Radix (Astragalus membranaceus) and their inhibitory activity on nitric oxide production. J. Agr. Food Chem. 59: 1131–1137 (2011)

    Article  CAS  Google Scholar 

  31. Efdi M, Ohguchi K, Akao NY, Koketsu M, Ishihara H. N-transferuloyltyramine as a melanin biosynthesis inhibitor. Biol. Pharm. Bull. 30: 1972–1974 (2007)

    Article  CAS  Google Scholar 

  32. Tai SS, Lin CG, Wu MH, Chang TS. Evaluation of depigmenting activity by 8-hydroxydaidzein in mouse B16 melanoma cells and human volunteers. Int. J. Mol. Sci. 10: 4257–4266 (2009)

    Article  CAS  Google Scholar 

  33. Schurink M, van Berkel WJ, Wichers HJ, Boeriu CG. Novel peptides with tyrosinase inhibitory activity. Peptides 28: 485–495 (2007)

    Article  CAS  Google Scholar 

  34. Chu HL, Wang BS, Duh PD. Effects of selected organo-sulfur compounds on melanin formation. J. Agr. Food Chem. 57: 7072–7077 (2009)

    Article  CAS  Google Scholar 

  35. Kim JH, Kim MR, Lee ES, Lee CH. Inhibitory effects of calycosin isolated from the root of Astragalus membranaceus on melanin biosynthesis. Biol. Pharm. Bull. 32: 264–268 (2009)

    Article  CAS  Google Scholar 

  36. Park EJ, Kim Y, Kim J. Acylated flavonol glycosides from the flower of Inula britannica. J. Nat. Prod. 63: 34–36 (2000)

    Article  CAS  Google Scholar 

  37. Gilgun-Sherki Y, Melamed E, Offen D. Oxidative stress inducedneurodegenerative diseases: The need for antioxidants that penetrate the blood brain barrier. Neuropharmacology 40: 959–975 (2001)

    Article  CAS  Google Scholar 

  38. Dearden JC. Partitioning and lipophilicity in quantitative structureactivity relationships. Environ. Health Persp. 61: 203–228

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Choong Hwan Lee.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kim, J.H., Lee, E.S. & Lee, C.H. Melanin biosynthesis inhibitory effects of calycosin-7-O-β-d-glucoside isolated from astragalus (Astragalus membranaceus). Food Sci Biotechnol 20, 1481–1485 (2011). https://doi.org/10.1007/s10068-011-0205-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-011-0205-4

Keywords

Navigation