Journal of Microbiology and Biotechnology

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
권호 표지
DOI QR코드

DOI QR Code

Melanin Synthesis Inhibition and Radical Scavenging Activities of Compounds Isolated from the Aerial Part of Lespedeza cyrtobotrya

  • Lee, Mi-Yeon (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Kim, Jin-Hee (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Choi, Jung-Nam (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Kim, Ji-Young (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Hwang, Geum-Sook (Korea Basic Science Institute) ;
  • Lee, Choong-Hwan (Department of Bioscience and Biotechnology, Konkuk University)
  • Received : 2009.05.27
  • Accepted : 2009.07.17
  • Published : 2010.06.28
Download PDF
⟨ Previous Next ⟩

Abstract

The EtOAc fraction of Lespedeza cyrtobotrya showed mushroom tyrosinase inhibitory and radical scavenging activities. Four active compounds were isolated based on Sephadex LH-20 chromatography and HPLC, and the structures were elucidated, on the basis of their LC-MS and NMR spectral data, as 2-(2,4-dihydroxyphenyl)-6-hydroxybenzofuran (1), eriodictyol-7-O-glucopyranoside (2), haginin A (3), and dalbergioidin (4), respectively. Compound (1) showed mushroom tyrosinase inhibitory activity with an $IC_{50}$ value of $5.2\;{\mu}M$ and acted as a competitive inhibitor. Furthermore, $37.3\;{\mu}M$ of compound 1 reduced 50% of the melanin content on human melanoma (MNT-1) cells. The radical scavenging activities of compounds 1, 2, 3, and 4 were shown to have $IC_{50}$ values of 11.0, 24.5, 9.0, and $36.5\;{\mu}M$, respectively, in an ABTS system and $IC_{50}$ values of 42.7, 36.0, 37.7, and $61.7\;{\mu}M$, respectively, in a DPPH system. The mushroom tyrosinase inhibitory activity of the EtOAc fraction of Lespedeza cyrtobotrya was contributed by compounds 1, 3, and 4, and its radical scavenging activity was contributed by compounds 1-4.

Keywords

References

  1. Abdel-Malek, Z. A., J. Knittel, A. L. Kadekaro, V. B. Swope, and R. Starner. 2008. The melanocortin 1 receptor and the UV response of human melanocytes - a shift in paradigm. Photochem. Photobiol. 84: 501-508. https://doi.org/10.1111/j.1751-1097.2008.00294.x
  2. Baek, S. H., J. H. Kim, D. H. Kim, C. Y. Lee, J. Y. Kim, D. K. Chung, and C. H. Lee. 2008. Inhibitory effect of dalbergioidin isolated from the trunk of Lespedeza cyrtobotrya on melanin biosynthesis. J. Microbiol. Biotechnol. 18: 874-879.
  3. Duncan, C. L. and E. M. Foster. 1968. Effect of sodium nitrite, sodium chloride, and sodium nitrate on germination and outgrowth of anaerobic spores. Appl. Microbiol. 16: 406-411.
  4. Fitton, A. and K. L. Goa. 1991. Azelaic acid. A review of its pharmacological properties and therapeutic efficacy in acne and hyperpigmentary skin disorders. Drugs 41: 780-798. https://doi.org/10.2165/00003495-199141050-00007
  5. Garrett, R. and C. Grisham. 2005. Biochemistry, pp. 421-432. 3rd Ed. Thomson Brooks/Cole, Belmont, CA.
  6. Ha, Y. M., S. W. Chung, S. Song, H. Lee, H. Suh, and H. Y. Chung. 2007. 4-(6-Hydroxy-2-naphthyl)-1,3-bezendiol: A potent, new tyrosinase inhibitor. Biol. Pharm. Bull. 30: 1711-1715. https://doi.org/10.1248/bpb.30.1711
  7. Kim, J. H., S. H. Baek, D. H. Kim, T. Y. Choi, T. J. Yoon, J. S. Hwang, M. R. Kim, H. J. Kwon, and C. H. Lee. 2008. Downregulation of melanin synthesis by haginin A and its application to in vivo lightening model. J. Invest. Dermatol. 128: 1227-1235. https://doi.org/10.1038/sj.jid.5701177
  8. Kim, Y. J. 2007. Antimelanogenic and antioxidant properties of gallic acid. Biol. Pharm. Bull. 30: 1052-1055. https://doi.org/10.1248/bpb.30.1052
  9. Kubo, I., I. Kinst-Hori, S. K. Chaudhuri, Y. Kubo, Y. Sanchez, and T. Ogura. 2000. Flavonols from Heterotheca inuloides: Tyrosinase inhibitory activity and structural criteria. Bioorg. Med. Chem. 8: 1749-1755. https://doi.org/10.1016/S0968-0896(00)00102-4
  10. Lee, C. H., M. C. Chung, H. J. Lee, K. S. Bae, and Y. H. Kho. 1997. MR566A and MR566B, new melanin synthesis inhibitors produced by Trichoderma harzianum. I. Taxonomy, fermentation, isolation and biological activities. J. Antibiot. 50: 469-473. https://doi.org/10.7164/antibiotics.50.469
  11. Lee, Y. S., J. H. Park, M. H. Kim, S. H. Seo, and H. J. Kim. 2006. Synthesis of tyrosinase inhibitory kojic acid derivative. Arch. Pharm. 339: 111-114. https://doi.org/10.1002/ardp.200500213
  12. Maeda, K. and M. Fukuda. 1996. Arbutin: Mechanism of its depigmenting action in human melanocyte culture. J. Pharmacol. Exp. Ther. 276: 765-769.
  13. Miyase, T., A. Ueno, T. Noro, and S. Fukushima. 1980. Studies on the constituents of Lespedeza cyrtobotrya $M_{IQ}$. I. The structures of a new chalcone and two new isoflav-3-ens. Chem. Pharm. Bull. 28: 1172-1177. https://doi.org/10.1248/cpb.28.1172
  14. Miyase, T., A. Ueno, T. Noro, and S. Fukushima. 1981. Studies on the constituents of Lespedeza cyrtobotrya $M_{IQ}$. II. The structures of haginin C, haginin D and lespedol C. Chem. Pharm. Bull. 29: 2205-2209.
  15. Mori-Hongo, M., H. Yamaguchi, T. Warashina, and T. Miyase. 2009. Melanin synthesis inhibitors from Lespedeza cyrtobotrya. J. Nat. Prod. 72: 63-71. https://doi.org/10.1021/np800535g
  16. Pan, J., S. Zhang, L. Yan, J. Tai, Q. Xiao, K. Zou, Y. Zhou, and J. Wu. 2008. Separation of flavanone enantiomers and flavanone glucoside diastereomers from Balanophora involucrata Hook. f. by capillary electrophoresis and reversed-phase high-performance liquid chromatography on a C18 column. J. Chromatogr. A 1185: 117-129. https://doi.org/10.1016/j.chroma.2008.01.049
  17. Park, D. J. and J. C. Lee. 2008. A study on the antioxidative and depigmentation activities of the ethanol extract of Saururus herba. Kor. J. Herbology 23: 193-102.
  18. Park, S. H., D. S. Kim, W. G. Kim, I. J. Ryoo, D. H. Lee, C. H. Huh, S. W. Youn, I. D. Yoo, and K. C. Park. 2004. Terrein: A new melanogenesis inhibitor and its mechanism. Cell Mol. Life Sci. 61: 2878-2885. https://doi.org/10.1007/s00018-004-4341-3
  19. Parvez, S., M. Kang, H. S. Chung, C. Cho, M. C. Hong, M. K. Shin, and H. Bae. 2006. Survey and mechanism of skin depigmenting and lightening agents. Phytother. Res. 20: 921-934. https://doi.org/10.1002/ptr.1954
  20. Parvez, S., M. Kang, H. S. Chung, and H. Bae. 2007. Naturally occurring tyrosinase inhibitors: Mechanism and applications in skin health, cosmetics and agriculture industries. Phytother. Res. 21: 805-816. https://doi.org/10.1002/ptr.2184
  21. Perluigi, M., F. De Marco, C. Foppoli, R. Coccia, C. Blarzino, M. L. Marcante, and C. Cini. 2003. Tyrosinase protects human melanocytes from ROS-generating compounds. Biochem. Biophys. Res. Commun. 305: 250-256. https://doi.org/10.1016/S0006-291X(03)00751-4
  22. Prota, G. 1988. Progress in the chemistry of melanins and related metabolites. Med. Res. Rev. 8: 525-556. https://doi.org/10.1002/med.2610080405
  23. Re, R., N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, and C. Rice-Evans. 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med. 26: 1231-1237. https://doi.org/10.1016/S0891-5849(98)00315-3
  24. Solano, F., S. Briganti, M. Picardo, and G. Ghanem. 2006. Hypopigmenting agents: An updated review on biological, chemical and clinical aspects. Pigment Cell Res. 19: 550-571. https://doi.org/10.1111/j.1600-0749.2006.00334.x
  25. Valverde, P., P. Manning, C. Todd, C. J. McNeil, and A. J. Thody. 1996. Tyrosinase may protect human melanocytes from the cytotoxic effects of the superoxide anion. Exp. Dermatol. 5: 247-253. https://doi.org/10.1111/j.1600-0625.1996.tb00125.x
  26. Vielhaber, G., G. Schmaus, K. Jacobs, H. Franke, S. Lange, M. Herrmann, H. Joppe, and O. Koch. 2007. 4-(1-Phenylethyl)1,3-benzenediol: A new, highly efficient lightening agent. Int. J. Cosmet. Sci. 29: 65-66.
  27. Yasui, H. and H. Sakurai. 2003. Age-dependent generation of reactive oxygen species in the skin of live hairless rats exposed to UVA light. Exp. Dermatol. 12: 655-661. https://doi.org/10.1034/j.1600-0625.2003.00033.x
  28. Yoshida, T., K. Mori, T. Hatano, T. Okumura, I. Uehara, K. Komagoe, Y. Fujita and T. Okuda. 1989. Studies on inhibition mechanism of autoxidation by tannins and flavonoids. V. Radical-scavenging effects of tannins and related polyphenols on 1,1-diphenyl-2-picrylhydrzyl radical. Chem. Pharm. Bull. 37: 1919-1921. https://doi.org/10.1248/cpb.37.1919

Cited by

  1. Metabolite Profiling and Bioactivity of Rice Koji Fermented by Aspergillus Strains vol.22, pp.1, 2012, https://doi.org/10.4014/jmb.1106.06033
  2. Antimelanogenic chemicals with in vivo efficacy against skin pigmentation in guinea pigs vol.37, pp.10, 2010, https://doi.org/10.1007/s12272-014-0447-9
  3. Seasonal Variations of Metabolome and Tyrosinase Inhibitory Activity of Lespedeza maximowiczii during Growth Periods vol.63, pp.38, 2010, https://doi.org/10.1021/acs.jafc.5b03566
  4. Dalbergioidin (DAL) protects MC3T3-E1 osteoblastic cells against H2O2-induced cell damage through activation of the PI3K/AKT/SMAD1 pathway vol.390, pp.7, 2010, https://doi.org/10.1007/s00210-017-1365-4
  5. The pharmacological and biological roles of eriodictyol vol.43, pp.6, 2010, https://doi.org/10.1007/s12272-020-01243-0