Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Triterpenoids from Roots of Glycine max (L.) Merr

  • Lee, Jin-Hwan (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University) ;
  • Seo, Kwon-Il (Department of Food and Nutrition, Sunchon National University) ;
  • Kang, Nam-Suk (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University) ;
  • Yang, Min-Suk (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University) ;
  • Park, Ki-Hun (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University)
  • Published : 2006.06.30
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Abstract

Metanolic root extract of Glycine max (L.) Merr. was chromatographed, affording three triterpenoids 1-3. The compound 3 was isolated from microorganism called Fusarium sporotrichioides but never been isolated from any plant sources. Compounds 1-3 showed cytotoxic activity against HT-59 human cancer cell line with $IC_{50}$ values of 62.9, 20.0, and $44.2{\mu}M$, respectively. Compound 3 showed significant activities against Gram-positive bacterial such as Bacillus cereus, Bacillus subtilis, and Staphylococcs aureus.

Keywords

References

  1. EL-Mekkawy, S., Meselhy, M. R., Nakamura, N., Tezuka, Y., Hattori, M., Kakiuchi, N., Shimotohno, K., Kawahata, T. and Otake, T. (1998) Anti-HIV-1 and anti-HIV-protease substances from Ganoderma lucidum. Phytochemistry 49, 1651-1657 https://doi.org/10.1016/S0031-9422(98)00254-4
  2. Honda, T., Rounds, B. V., Bore, L., Finlay, H. J., Favaloro, F. G., Jr., Suh, N., Wang, Y., Sporn, M. B. and Gribble, G. W. (2000) Synthetic oleanane and ursane triterpenoids with modified rings A and C: a series of highly active inhibitors of nitric oxide production in mouse macrophages. J. Med. Chem. 43, 4233-4246 https://doi.org/10.1021/jm0002230
  3. Lee, S. M., Park, J. G., Lee, Y. H., Lee, C. G., Min, B. S., Kim, J. H. and Lee, H. K. (2004) Anti-complementary activity of triterpenoids from fruits of Zizyphus jujube. Biol. Pharm. Bull. 27, 1883-1886 https://doi.org/10.1248/bpb.27.1883
  4. Leu, Y. L., Kuo, S. M., Hwang, T. L. and Chiu, S. T. (2004) The inhibition of superoxide anion generation by neutrophils from Viscum articulactum. Chem. Pharm. Bull. 52, 858-860 https://doi.org/10.1248/cpb.52.858
  5. Yim, T. K., Wu, W. K., Pak, W. F. and Ko, K. M. (2001) Hepatoprotective action of an oleanolic acid-enriched extract of Ligustrum lucidum fruits is mediated through an enhancement on hepatic glutathione regeneration capacity in mice. Phytother. Res. 15, 589-592 https://doi.org/10.1002/ptr.878
  6. Kim, K. A., Lee, J. S., Park, H. J., Kim, J. W., Kim, C. J., Shim, I. S., Kim, N. J. and Han, S. M. (2004) Inhibition of cytochrome P450 activities by oleanolic acid and ursolic acid in human liver microsomes. Life Sci. 74, 2769-2779 https://doi.org/10.1016/j.lfs.2003.10.020
  7. Hsu, H. Y., Yang, J. J. and Lin, C. C. (1997) Effects of oleanolic acid ursolic acid on inhibiting tumor growth and enhancing the recovery of hematopoietic system postirradiation in mice. Cancer Lett. 111, 7-13 https://doi.org/10.1016/S0304-3835(96)04481-3
  8. Choi, C. Y., You, H. J. and Jeong, H. G. (2001) Nitric oxide and tumor necrosis factor-alpha production by oleanolic acid via nuclear factor-kappaB activation in macrophages. Biochem. Biophys. Res. Commun. 288, 49-55 https://doi.org/10.1006/bbrc.2001.5727
  9. Andrikopoulos, N. K., Kaliora, A. C., Assimopoulou, A. N. and Papageorgiou, V. P. (2002) Inhibitory activity of minor polyphenolic and nonpolyphenolic constituents of olive oil against in vitro low-density lipoprotein oxidation. J. Med. Food 5, 1-7 https://doi.org/10.1089/109662002753723160
  10. Pollard, M. and Wolter, W. (2000) Prevention of spontaneous prostaterelated cancer in Lobund-Wistar rats by a soy protein isolate/isoflavone diet. Prostate 45, 101-105 https://doi.org/10.1002/1097-0045(20001001)45:2<101::AID-PROS3>3.0.CO;2-P
  11. Wu, A. H., Ziegler, R. G., Nomura, A. M. Y., West, D. W., Kolonel, L. N., Ross, P. L. H. and Pike, M. C. (1998) Soy intake and risk of breast cancer in Asians and Asian Americans. Am. J. Clin. Nutr. 68, 1437S-1443S
  12. Anthony, M. S., Clarkson, T. B., Hughes, C. L., Morgan, T. M. and Burke, G. L. (1996) Soybean isoflavones improve cardiovascular risk factors without affecting the reproductive system of peripubertal Rhesus monkeys. J. Nutr. 126, 43-50 https://doi.org/10.1093/jn/126.1.43
  13. Merz-Demlow, B. E., Duncan, A. M., Wangen, K. E., Xu, X., Carr, T. P., Phipps, W. R. and Kurzer, M. S. (2000) Soy isoflavones improve plasma lipids in normcholesterolemic permenopausal women. Am. J. Clin. Nutr. 71, 1462-1469 https://doi.org/10.1093/ajcn/71.6.1462
  14. Wilcox, J. N. and Blumenthal, B. F. (1995) Thrombotic mechanisms in atherosclerosis: potential impact of soy proteins. J. Nutr. 125, 631S-638S
  15. Arjmandi, B. H., Getlinger, M. J., Goyal, N. V., Alekel, L., Hasler, C. M., Juma, S., Drum, M. L., Hollis, B. W. and Kukreja, S. C. (1998) Role of soy protein with normal or reduced isoflavone content in reversing bone loss induced by ovarian hormone deficiency in rats. Am. J. Clin. Nutr. 68, 1358S-1363S https://doi.org/10.1093/ajcn/68.6.1358S
  16. Arjmandi, B. H., Alekel, L., Hollis, B. W., Amin, D., Stacewicz- Sapuntzakis, M., Guo, P. and Kukreja, S. C. (1996) Dietary soybean protein prevents bone loss in an ovarietomized rat model of osteroporosis. J. Nutr. 126, 161-167 https://doi.org/10.1093/jn/126.1.161
  17. Wu, Q., Wang, M., Sciarappa, W. J. and Simon, J. E. (2004) LC/UV/ESI-MS analysis of isoflavones in edamame and tofu soybeans. J. Agric. Food Chem. 52, 2763-2769 https://doi.org/10.1021/jf035053p
  18. Rostagno, M. A., Palma, M. and Barroso, C. G. (2004) Pressurized liquid extraction of isoflavones from soybeans. Anal. Chim. Acta 522, 169-177 https://doi.org/10.1016/j.aca.2004.05.078
  19. Dwyer, J. T, Goldin, B. R., Saul, N., Gualtieri, L., Barakat, S. and Adlercreutz, H. (1994) Tofu and soy drinks contain phytoestrogens. J. Am. Diet. Assoc. 94, 739-743 https://doi.org/10.1016/0002-8223(94)91939-9
  20. Lee, J. H., Lee, B. W., Kim, J. H., Jeong T.-S., Kim, M. J., Lee, W. S. and Park, K. H. (2006) LDL-antioxidant pterocarpans from roots of Glycine max (L.) Merr. J. Agric. Food Chem. 54, 2057-2063 https://doi.org/10.1021/jf052431c
  21. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D. and Warren, J. (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 82, 1107-1112 https://doi.org/10.1093/jnci/82.13.1107
  22. Piddok, L. J. V. (1990) Techinques used for the determination of antibacterial resistance and sensitivity in bacteria. J. Appl. Bacteriol. 68, 307-318 https://doi.org/10.1111/j.1365-2672.1990.tb02880.x
  23. Kitagawa, I., Yoshikawa, M., Wang, H. K., Saito, M., Tosirisuk, V., Fujiwara, T. and Tomita, K. I. (1982) Revised structures of soyasapogenols A, B, and E, oleanene-sapogenols from soybean. Chem. Pharm. Bull. 30, 2294-2297 https://doi.org/10.1248/cpb.30.2294
  24. Yagen, B., Horn, P., Joffe, A. Z. and Cox, R. H. (1980) Iso lation and structural elucidation of a novel sterol metabolite of Fusarium sporotrichioides J. C. S. Perkin I. 921, 2914-2917
  25. Singh, S. B., Zink, D. L., Dombrowski, A. W., Polishook, J. D., Ondeyka, J. G., Hirshfield, J., Felock, P. and Hazuda, D. J. (2003) Integracides: tetracyclic triterpenoid inhibitors of HIV-1 integrase produced by Fusarium Sp. Bioorg. Med. Chem. 11, 1577-1582 https://doi.org/10.1016/S0968-0896(02)00529-1