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.
Similar content being viewed by others
References
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)
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)
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)
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)
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)
Briganti S, Camera E, Picardo M. Chemical and instrumental approaches to treat hyperpigmentation. Pigm. Cell Res. 16: 101–110 (2003)
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)
Sato K, Toriyama M. Effect of pyrroloquinoline quinone (PQQ) on melanogenic protein expression in murine B16 melanoma. J. Dermatol. Sci. 53: 140–145 (2009)
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)
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)
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)
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)
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)
Maeda K, Fukuda M. Arbutin: Mechanism of its depigmenting action in human melanocyte culture. J. Pharmacol. Exp. Ther. 276: 765–769 (1996)
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)
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)
Penney KB, Smith CJ, Allen JC. Depigmenting action of hydroquinone depends on disruption of fundamental cell processes. J. Invest. Dermatol. 82: 308–310 (1984)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Efdi M, Ohguchi K, Akao NY, Koketsu M, Ishihara H. N-transferuloyltyramine as a melanin biosynthesis inhibitor. Biol. Pharm. Bull. 30: 1972–1974 (2007)
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)
Schurink M, van Berkel WJ, Wichers HJ, Boeriu CG. Novel peptides with tyrosinase inhibitory activity. Peptides 28: 485–495 (2007)
Chu HL, Wang BS, Duh PD. Effects of selected organo-sulfur compounds on melanin formation. J. Agr. Food Chem. 57: 7072–7077 (2009)
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)
Park EJ, Kim Y, Kim J. Acylated flavonol glycosides from the flower of Inula britannica. J. Nat. Prod. 63: 34–36 (2000)
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)
Dearden JC. Partitioning and lipophilicity in quantitative structureactivity relationships. Environ. Health Persp. 61: 203–228
Author information
Authors and Affiliations
Corresponding author
Rights 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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10068-011-0205-4