Cytotoxic and ACAT-inhibitory sesquiterpene lactones from the root ofIxeris dentata formaalbiflora

  • Eun-Mi Ahn
  • Myun-Ho Bang
  • Myoung-Chong Song
  • Mi-Hyun Park
  • Hwa-Young Kim
  • Byoung-Mog Kwon
  • Nam-In Baek
Articles Drug Design
Received:

Abstract

Ixeris dentata formaalbiflora was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc,n-BuOH and H2O. Eight sesquiterpenes were isolated through repeated silica gel and octadecyl silica gel (C18, ODS) column chromatography of the EtOAc andn-BuOH fractions. Physicochemical analysis using NMR, MS and IR revealed the chemical structures of the sesquiterpenes, which were zaluzanin (1), 9a-hydroxyguaian-4(15), 10(14), 11(13)-triene-6, 12-olide (2), 3β-O-β-D-glucopyranosyl-8β-hydroxyguaian-4(15), 10(14)-diene-6,12-olide (3), 3-O-β-D-glucopyranosyl-8β-hydroxyguauan-10(14)-ene-6,12-olide (4), ixerinM (5), glucozaluzanin C (6), crepiside I (7), and ixerin D (8). This is the first time that these sesquiterpene lactones have been isolated from this plant. Compounds1, 2 and7 revealed relatively high cytotoxicities on human colon carcinoma cell and lung adenocarcinoma cell, while compounds5 and7 showed acyl-CoA: cholesterol acyltransferase (ACAT) inhibitory activity.

Key words

Ixeris dentata formaalbiflora Sesquiterpene lactone ACAT HT29 A549 
This is a preview of subscription content, log in to check access.

References

  1. Arai, Y., Kusumoto, Y., Nagao, M., Shiojima, K., and Ageta, H., Compositae constituents: Aliphatics and triterpenoide isolated from the whole plants ofIxeris debilis andI. dentata.Yakugaku Zasshi, 103, 356 (1985).Google Scholar
  2. Bang, M. H., Jang, T. H., Song, M. C., Kim, D. H., Kwon, B. M., Kim, Y. K., Lee, H. S., Chung, I. S., Kim, D. K., Kim, S. H., Park, M. H., and Baek, N. I., Screening of biologically active compound from edible plant sources-IX. Isolation and identification of sesquiterpene lactones isolated from the root ofIxeris dentate formaalbiflora; inhibition effects on ACAT, DGAT and FPTase activity.J. Korean Soc. Appl. Biol. Chem., 47, 251–257 (2004).Google Scholar
  3. Brown, M. S., Dana, S. E., and Goldstein, J. L., Cholsterol ester formation in cultured human fibroblasts.J. Biol. Chem., 250, 4025–4027 (1975).PubMedGoogle Scholar
  4. Brecher, P. and Chan, C. T., Properties of acyl-CoA: CholesterolO-acyltransferase in aortic microsomes from atherosclerotic rabbits.Biochem. Biophys. Acta., 617, 458–471 (1980).PubMedGoogle Scholar
  5. Chan, E. W., Cheng, S. C., Sin, F. W., and Xie, Y., Triptolide induced cytotoxic effects on human promyelocytic leukemia, T cell lymphoa and human hepatocellular carcinoma cell lines.Toxicol. Lett., 122, 81–87 (2001).PubMedCrossRefGoogle Scholar
  6. Geissman, T. A., in Recent Advances in Phytochemistry. Vol. 6. Runeckless, V. C. and Mabry, T. J. (eds.), Academic Press, New York. (1973).Google Scholar
  7. Hidehisa, A., Toshio, M., and Seigo F., Sesquiterpene lactones from Ixeris tamagawaensis Kitam II.Chem. Pharm. Bull., 32. 3036–3042 (1984).Google Scholar
  8. Jeong, T. S., Kim, S. U., Son, K. H., Kwon, B. M., Kim, Y. K., Choi, M. U., and Bok, S. H., GERI-BP001 compounds, new inhibitors of acyl-CoA: Cholesterol acytransferase fromAspergillus fumigatus F37.J. Antibiot., 48, 751–756 (1995).PubMedGoogle Scholar
  9. Kim, M. K. and Lee, M. S., Volatile flavor components ofIxeris dentata andAmaranthus mangostanus.J. Kor. Agric. Chem. Soc., 31, 394–399 (1988).Google Scholar
  10. Lee, C. H., Jeong, T. S., Choi, Y. K., Hyun, B. W., Oh, G. T., Kim, E. H., Kim, J. R., Han, J. I., and Bok, S. H., Anti-atherogenic effect of citrus flanonoids, naringin and naringenin, associated with hepatic ACAT and aortic VCAM-1 and MCP-1 in high cholesterol-fed rabits.Biochem. Biophys. Res. Commun., 284, 681–688 (2001).PubMedCrossRefGoogle Scholar
  11. Mamoru, S., Toshio, M. and Seigo, F., Sesquiterpene lactones fromIxeris dentate Nakai.Chem. Pharm. Bull., 34, 4170–4176 (1986).Google Scholar
  12. Miyase, T., Ueno, A., Noro, T., Kuroyanagi, K., and Fukushima S., Studies on sesquiterpene glycosides fromCrepis japonica BENTH.Chem. Pharm. Bull., 33, 4451–4456 (1985).Google Scholar
  13. Miyase, T. and Fukushima, S., Sesquiterpene lactones fromAinsliaea acerifolia Sch. Bip. andA. dissecta Franch. Et Sav.Chem. Pharm. Bull., 32, 3043–3046 (1984).Google Scholar
  14. Robles, M., Aregullin, M., West, J., and Rodriguez, E., Recent studies on the zoopharmacognosy, pharmacology and neurotoxicology of sesquiterpene lactones.Planta Med., 61, 199–203 (1995).PubMedCrossRefGoogle Scholar
  15. Seto, M., Miyasa, T., and Fukushima, S. Sesquiterpene lactones fromIxeris dentata Nakai.Chem. Pharm. Bull., 34, 4170–4176 (1986).Google Scholar
  16. Soka, T., InDictionary of Chinese Drugs (1st ed.) Shanghai Science Technology Shogakukan Press, Tokyo (1985).Google Scholar
  17. Warashina, T., Ishino, M., Miyase, T., and Ueno, A., Sesquiterpene glycosides fromIxeris debilis andIxeris repens.Phytochemistry. 29, 3217–3224 (1990).CrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea 2006

Authors and Affiliations

  • Eun-Mi Ahn
    • 1
  • Myun-Ho Bang
    • 2
  • Myoung-Chong Song
    • 2
  • Mi-Hyun Park
    • 3
  • Hwa-Young Kim
    • 3
  • Byoung-Mog Kwon
    • 4
  • Nam-In Baek
    • 2
  1. 1.Department of Herbal Food ScienceDaegu Haany UniversityGyeongsanKorea
  2. 2.Graduate School of BiotechnologyKyungHee UniversitySuwonKorea
  3. 3.Erom Life Co. Ltd.SeoulKorea
  4. 4.Korea Research Institute of Bioscience and BiotechnologyDaejonKorea

Personalised recommendations