Anti-Rheumatoid Arthritis Effect of the Kochia scoparia Fruits and Activity Comparison of Momordin Ic, its Prosapogenin and Sapogenin

  • Published : 2002.06.01

Abstract

MeOH extract of Kochia scoparia was fractionated into $CHCl_3-$, EtOAc- and BuOH extracts and the last fraction were hydrolyzed by 3%-NaOH ($MeOH-H_2O$) to compare the bioactivities on antinociceptive and anti-inflammatory effects. Silica gel column chromatography of BuOH fraction afforded a large amount of $3-Ο-{\beta}-D-xylopyranosyl {\;}(1{\rightarrow}3)-{\beta}-D-glucuronopyranosyl$ oleanolic acid (momordin Ic, 4) and that of acid hydrolysate of BuOH fraction gave $3-Ο-{\beta}-D-glucuronopyranosyl oleanolic$ acid (momordin Ib, 3), its 6'-Ο-methyl ester (2) and oleanolic acid (1). Silica gel column chromatography of alkaline hydrolysate afforded a large amount of 4. MeOH extract and both EtOAc- and BuOH fractions were active in the rheumatoidal rat induced Freund's complete adjuvant reagent (FCA) whereas $CHCl_3$ fraction was inactive. Compound 1 and 4 showed significant activities in the same assay but oleanolic acid 3-Ο-glucuronopyranoside (3) showed no activity. These fashions were also observed in carrageenan-induced edema of the rat and in the antinociceptive activity tests undertaken in hot plate- and writhing methods. These results suggest that momordin Ic and its aglycone, oleanolic acid, could be active principles for rheumatoid arthritis.

Keywords

References

  1. Choi J. W., Huh, K., Kim, S. H., Lee, K. T., Park, H. J., and Han, Y. N., Antinociceptive and antirheumatoidal effects of Kalopanax pictus extract and its saponin components in excerimental animals. Journal of Ethnopharmacology, 199-202(2002a) https://doi.org/10.1016/S0378-8741(01)00383-X
  2. Choi J. W., Huh, K., Kim, S. H., Lee, K. T., Lee, H. K., and Park, H .J., Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent. Journal of Ethnopharmacology, 113-118 (2002b) https://doi.org/10.1016/S0378-8741(01)00382-8
  3. Gine-Larza E. M., Manez, S., Recio, M. C., and Giner, R. M., Oleanonic acid, a 3-oxotriterpene from Pistacia inhibits leukotriene synthesis and has antiinflammatory activity. European Journal of Pharmacology, 428, 137-143 (2001) https://doi.org/10.1016/S0014-2999(01)01290-0
  4. Kawamura, N., Watanabe, H., and Oshio, H., Saponins from the roots of Momordica cochinchinensis. Phyto-chemistry, 11,3585-3591 (1988)
  5. Kim, D. H., Yu, K. W., Bae, E. A., Park, H. J., and Choi, J. W., Metabolism of Kalopanaxsaponin Band H by human intestinal bacteria and antidiabetic activity of their metabolites. Biological and Pharmaceutical Bulletin, 21, 360-365(1998) https://doi.org/10.1248/bpb.21.360
  6. Matsuda, H., Dai, Y., Ido, Y., Ko, S., Yoshikawa, M., and Kubo, M., Studies on Kochiae Fructus III. Antinociceptive and antiinflammatory effects of 70% ethanol extract and its component, momordin Ic from dried fruits of Kochia scoparia L. Biological and Pharmaceutical Bulletin, 20, 1086-1091(1997a) https://doi.org/10.1248/bpb.20.1086
  7. Matsuda, H., Dai, Y., Ido, Y., Yoshikawa, M., and Kubo, M., Studies on Kochiae Fructus IV. Anti-allergic effects of 70% ethanol extract and its component, momordin Ic from dried fruits of Kochia scoparia L. Biological and Pharmaceutical Bulletin, 20,1165-1170 (1997b) https://doi.org/10.1248/bpb.20.1165
  8. Matsuda, H., Li, Y., Murakami, T., Yarnahara, J., and Yoshikawa, M., Structure-related inhibitory activity of oleanolic acid glycosides on gastric emptying in mice. Bioorg. Med. Chem., 7, 323-327 (1999a) https://doi.org/10.1016/S0968-0896(98)00207-7
  9. Matsuda, H., Li, Y., and Yoshikawa, M., Roles of capsaicinsensitive sensory nerves, endogenous nitric oxide, sulfhydryls, and prostaglandins in gastroprotection by momordin Ic, an oleanolic acid oligoglycoside, on ethanol-induced mucosal lesions in rats. Life Science, 65, PL27-32 (1999b) https://doi.org/10.1016/S0024-3205(99)00241-6
  10. Shao, C. -J., Kasai, R., Xu, J. -D., and Tanaka, O., Saponins from roots of Kalopanax septemlobus (Thunb.) Koidz., Ciqiu: Structures of Kalopanaxsaponins C, D, E and F. Chemical and Pharmaceutical Bulletin, 37, 311-314 (1989) https://doi.org/10.1248/cpb.37.311
  11. Wen Y., Chen, Y., Cui, Z., Li, J., and Wang, Z., Triterpenoid glycosides from the fruits of Kochia scoparia. Planta Medica, 61,450-452 (1995) https://doi.org/10.1055/s-2006-958134
  12. Whittle, B.A., The use of change in capillary permeability to distinguish between narcotic and anagesic. British Journal of Pharmacology 22, 246-460 (1949)
  13. Yoshikawa, M., Dai, Y., Shimada, H., Morikawa, T., Matsumura, N., Yoshizumi, H., Matsuda, H., and Kubo, M., Studies on Kochiae Fructus. II. On the saponin constituets from the fruit of Chinese Kocia scoparia (Chenopodiaceae): Chemical structures of Kochianosides I, II, III, and IV. Chemical and Pharmaceutical Bulletin, 45, 1052-1055 (1997) https://doi.org/10.1248/cpb.45.1052
  14. Yoshikawa, M., Shimada, H., Morikawa, T., Yoshizumi, S., Matsumura, N., Murakami, T., Matsuda, H., Hori, K., and Yamahara, J., Medicinal foodstuffs. VII. On the saponin constituents with glucose and alcohol adsorption-inhibitory activity from a food garnish 'tonburi' , the fruit of Japanese Kochia scoparia (L.) Schrad.: Structures of scoparianosides A, B and C. Chem. Pharm. Bull., 45, 1300-1305 (1997) https://doi.org/10.1248/cpb.45.1300
  15. Winter, C. A., Risley, E. A., and Nuss, G. W., Carrageenin induced edema in hind paw of the rat as an assay for anti-inflammatory drugs. Pro. Soc. Exp. Biol. Med. 111: 544-548(1962)
  16. Yim, T. K., Wu, W. K., Pak, W. F., Ko, K. M., Hepatoprotective action of oleanolic acid-enriched extract of Ligustrum lucidum fruits is mediated through an enhancement on hepatic glutathione regeneration capacity in mice. Phytotherapy Research, 15, 589-592 (2001) https://doi.org/10.1002/ptr.878