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Anti-allergic activity of 18β-glycyrrhetinic acid-3-O-β-D-glucuronide

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Abstract

Glycyrrhizin (18β-glycyrrhetinic acid-3-O-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronide, GL) was transformed to 18β-glycyrrhetinic acid-3-O-β-D-glucuronide (GAMG) byStreptococcus LJ-22. The antiallergic activities of GL and GAMG was measured using a RBL cell assay system and contact hypersensitivity model mice. GAMG exhibited anti-allergic activity with IC50 values of 0.28 mM. GAMG, which is sweeter than GL, and 18β-glycyrrhetinic acid, which is a GAMG metabolite by human intestinal bacteria, also inhibited the passive cutaneous anaphylaxis and skin contact inflammation. In conclusion, GAMG may be useful as a new sweet food additive and an anti-allergic agent.

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References

  • Abe, N., Ebina, T., and Ishida, N., Interferon induction by glycyrrhizin and glycyrrhetinic acid in mice.Microbiol. Immunol., 26, 535–539 (1982).

    PubMed  CAS  Google Scholar 

  • Brieskom, C. H. and Lang, J., 18β-Glycyrrhetinsaure und suer Geschmack.Arch. Pharm. (Weinheim), 311, 1001–1009 (1978).

    Article  Google Scholar 

  • Finney, R. S. H. and Somers, G. F., The anti-inflammatory activity of glycyrrhetinic acid and derivatives.J. Pharm. Pharmacol., 10, 613–620 (1958).

    PubMed  CAS  Google Scholar 

  • Fujii, Y., Takeuchi, H., Tanaka, K., Sakuma, S., Ohkubo, Y., and Mutoh, S., Effects of FK506 (tacrolimus hydrate) on chronic oxazolone-induced dermatitis in rats.Eur. J. Pharmacol., 456, 115–121 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Hirabayashi, K., Iwata, S., Matsumoto, H., Mori, T., Shibata, S., Baba, M., Ito, M., Shigeta, S., Nakashima, H., and Yamamoto, N., Antiviral activities of glycyrrhizin and its modified com- pounds against human immunodeficiency virus type 1 (HIV-1) and herpes simplex virus type 1 (HSV-1)in vitro.Chem. Pharm. Bull., 39, 112–115 (1991).

    PubMed  CAS  Google Scholar 

  • Katayama, S., Shionoya, H., and Ohtake, S., A new method for extraction of extravasated dye in the skin and the influence of fasting stress on passive cutaneous anaphylaxis in guinea pigs and rats.Microbiol. Immunol., 22, 89–101 (1978).

    Article  PubMed  CAS  Google Scholar 

  • Kim, D.-H., Lee, S.-W., and Han, M. J., Biotransformation of glycyrrhizin to 18β-glycyrrhetinic acid 3-O-β-D-glucuronide byStreptococcus LJ-22, a human intestinal bacteria.Biol. Pharm. Bull., 22, 320–322 (1999).

    PubMed  CAS  Google Scholar 

  • Kim, D.-H., Hong, S.-H., Kim, B. T., Bae, E.-A., Park, H. Y., and Han, M. J., Biotransformation of glycyrrhizin by human intestinal bacteria and its relation to biological activities.Arch. Pharm. Res., 23, 172–177 (2000).

    Article  PubMed  CAS  Google Scholar 

  • Kondo, Y. and Takano F., Nitric oxide production in mouse peritoneal macrophages enhanced with glycyrrhizin.Biol. Pharm. Bull., 17, 759–761 (1994).

    PubMed  CAS  Google Scholar 

  • Kumagai, A., Yano, M., Otomo, M., and Tekuchi, K., Study on the corticoid-like action of glycyrrhizin and mechanism of its action.Endocrinol. Jpn., 4, 1727 (1957).

    Google Scholar 

  • Kuramoto, T., Ito, Y., Oda, M., Tamura, Y., and Kitahata, S., Microbial production of glycyrrhetic acid 3-O-mono-β-D-glucuronide from glycyrrhizin byCryptococcus magnus MG-27,Biotech. Biochem., 58, 455–458 (1994).

    CAS  Google Scholar 

  • Mizutani, K., Kuramoto, T., Tamura, Y., Ohtake, N., Dol, S., Nakaura M., and Tanaka, O., Sweetess of glycyrrhetic acid 3-O-β-D-monoglucuronide and related glycosides.Biosci. Boitech. Biochem., 58, 554–555 (1994).

    Article  CAS  Google Scholar 

  • Mizutani, K. and Yukiyoshi, T., Development of sweet MGGR and its chemopreventive effect.Bioindustry, 12, 22–24 (1995).

    Google Scholar 

  • Pompeo, R., Flore, O., Marccialis, M. A., Pani, A., and Loddo, B., Glycyrrhizic acid inhibits virus growth and inactivates virus particles.Nature (London), 281, 689–690 (1979).

    Article  Google Scholar 

  • Ryu, S. Y., Oak, M. H., and Kim, K. M., Yomogin inhibits the degranulation of mast cells and the production of the nitric oxide in activated RAW 264.7 cells.Planta Med., 66, 171–173 (2000).

    Article  PubMed  CAS  Google Scholar 

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Correspondence to Dong-Hyun Kim.

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Park, HY., Park, SH., Yoon, HK. et al. Anti-allergic activity of 18β-glycyrrhetinic acid-3-O-β-D-glucuronide. Arch Pharm Res 27, 57–60 (2004). https://doi.org/10.1007/BF02980047

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  • DOI: https://doi.org/10.1007/BF02980047

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