Anti-Allergic Activity of 18$\beta$-Glycyrrhetinic acid-3-O-$\beta$-D-glucuronide

  • Published : 2004.01.01

Abstract

Glycyrrhizin (18$\beta$-glycyrrhetinic acid-3-O-$\beta$-D-glucuronopyranosyl-(1$\rightarrow2)-\beta$-D-glucuronide, GL) was transformed to 18$\beta$-glycyrrhetinic acid-3-O-$\beta$-D-glucuronide (GAMG) by Streptococcus 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 $IC_{50}$ values of 0.28 mM. GAMG, which is sweeter than GL, and 18$\beta$-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.

Keywords

References

  1. Abe, N., Ebina, T., and Ishida, N., Interferon induction by glycyrrhizin and glycyrrhetinic acid in mice. Microbiol. Immunol., 26, 535-539 (1982) https://doi.org/10.1111/j.1348-0421.1982.tb00207.x
  2. Brieskorn, C.H. and Lang, J., $18{\beta}$-Glycyrrhetinsaure und suer Geschmack. Arch. Pharm. (Weinheim), 311, 1001-1009 (1978) https://doi.org/10.1002/ardp.19783111205
  3. Finney, R. S. H. and Somers, G. F., The anti-inflammatory activity of glycyrrhetinic acid and derivatives. J. Pharm. Pharmacol., 10, 613-620 (1958) https://doi.org/10.1111/j.2042-7158.1958.tb10349.x
  4. 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) https://doi.org/10.1016/S0014-2999(02)02554-2
  5. 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 compounds 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) https://doi.org/10.1248/cpb.39.112
  6. 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. lmmunol., 22, 89-101 (1978) https://doi.org/10.1111/j.1348-0421.1978.tb00352.x
  7. Kim, D.-H., Lee, S.-W., and Han, M. J., Biotransformation of glycyrrhizin to $18{\beta}$-glycyrrhetinic acid 3-O-$\beta$-D-glucuronide by Streptococcus LJ-22, a human intestinal bacteria. BioI. Pharm. Bull., 22, 320-322 (1999) https://doi.org/10.1248/bpb.22.320
  8. 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) https://doi.org/10.1007/BF02975509
  9. Kondo, Y. and Takano F., Nitric oxide production in mouse peritoneal macrophages enhanced with glycyrrhizin. BioI. Pharm. Bull., 17, 759-761 (1994) https://doi.org/10.1248/bpb.17.759
  10. 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)
  11. Kuramoto, T, Ito, Y., Oda, M., Tamura, Y., and Kitahata, S., Microbial production of glycyrrhetic acid 3-O-mono-$\beta$-D-glucuronide from glycyrrhizin by Cryptococcus magnus MG-27, Biotech. Biochem., 58, 455-458 (1994) https://doi.org/10.1271/bbb.58.455
  12. Mizutani, K., Kuramoto, T., Tamura, Y., Ohtake, N., Dol, S., Nakaura M., and Tanaka, O., Sweetess of glycyrrhetic acid 3-O-$\beta$- D-monoglucuronide and related glycosides. Biosci. Boitech. Biochem., 58, 554-555 (1994) https://doi.org/10.1271/bbb.58.554
  13. Mizutani, K. and Yukiyoshi, T., Development of sweet MGGR and its chemopreventive effect. Bioindustry, 12, 22-24 (1995)
  14. 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) https://doi.org/10.1038/281689a0
  15. 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. Plante Med., 66, 171-173 (2000) https://doi.org/10.1055/s-0029-1243124