Advances in Traditional Medicine

Kyung Hee Oriental Medicine Research Center (경희대학교 융합한의과학연구소)
권호 표지
DOI QR코드

DOI QR Code

In vitro Biological Activity of Germacranolide sesquiterpene lactones

  • Kim, Myung-Ju (Department of Skin & Beauty, Kwangju Health Science College) ;
  • Lee, Jae-Sug (Department of Beauty Science, Kwangju Women's University) ;
  • Baek, Seung-Hwa (Department of Herbal Resources, Professional Graduate School of Oriental Medicine, Wonkwang University)
  • Published : 2009.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Bioactivity-directed isolation has led to the isolation of (-)-ent-costunolide (1) as the major active compound from Hepatostolonophora paucistipula. This compound (1) was determined by spectroscopic data interpretation. This sesquiterpene lactone (1) inhibited the growth of the dermatophytic fungus Trichophyton mentagrophytes ATCC 28185, (4 mm inhibition zone at $15{\mu}g$/disc), cytotoxic activity to murine leukaemia cell lines ATCC CCL 46 P 388D1 ($IC_{50}$ 687 ng/ml, at $0.075{\mu}g$/disk), BSC monkey kidney cell lines (100% of well at $15{\mu}g$/disk) and antiviral activity to Herpes simplex virus (0.25 mg/ml, 100% of well at $7.5{\mu}g$/disk) and Polio virus (0.125 mg/ml, 100% of well at $3.75{\mu}g$/disk). These results suggest that (-)-ent-costunolide (1) has potential antimicrobial and cytotoxic agents.

Keywords

References

  1. Asakawa Y. (1995) In progress in the Chemistry of Organic Natural Products, Vol. 65, p.1-185, Herz W, Kirby GW, Moore RE, Steglich W, Tamm C, Eds.; Springer Vienma
  2. Asakawa Y, Matsuda R, Cheminat A. (1987) Bibenzyl derivatives form Frullaniaspecies. Phytochem. 26, 1117-1122 https://doi.org/10.1016/S0031-9422(00)82361-4
  3. Asakawa Y, Muller JC, Ourisson G, Foussereau J, Ducombs G. (1976) New sesquiterpene lactones of Frullania (Hepaticae). Isolation, structures, allergenic properties. Bull. Soc. Chim. Fr. (Chim. Mol.) 1465-1466
  4. Appendino G, Taglialatela-Scafati O, Romano A, Pollastro F, Avonto C, Rubiolo P (2009): Genepolide, a sesquiterpene gamma-lactone with a novel carbon skeleton from mountain wormwood (Artemisia umbelliformis) (perpendicular) J. Nat. Prod. In press
  5. Baek SH, Perry NB, Lorimer SD (2003): (-)-ent-Costunolide from the liverwort Hepatostolonophora paucistipula, J. Chem. Res. 14-15 https://doi.org/10.3184/030823403103172977
  6. Baek SH, Perry NB, Weavers RT, Tangney RS. (1998) Geranyl phenyl ethers from the New Zealand liverwort Trichocolea hatcheri. J. Nat. Prod. 61, 126-129 https://doi.org/10.1021/np970379b
  7. Baek SH, Lim JA, Kwag JS, Lee HO, Chun HJ, Lee JH, Perry NB. (2003) Screening for biological activity of crude extract and fractions from Brachyglottis monroi. Kor. J. Orien. Physiol. Pathol. 17, 826-828
  8. Baek SH, Shin JH, Chung WY, Han DS. (2000) Antitumor evaluation of cannabidiol and its derivatives by colorimetric methods. J. Toxicol. Pub. Health 16, 101-107
  9. Beekman, A.C., Woerdenbag, H.J., Van Uden, W., Pras, N., Konings, A.W.T., Wiksom, K.V., Schmidt, T.J., 1997. Structure.cytotoxicity relationships of some hele anolide -type sesquiterpene lactones. J. Nat. Prod. 60, 252.257
  10. Cane DE. (1999) In Isoprenoids incluing carotenoids and steroids, p. 155-200, Cane, DE, ed., Elsevier; Amsterdam
  11. Chen WM, Ralf M, Helmuth Z, Gerhard R. (1998) A non-oxidized melamolide and other germacranolides from Aristolochia yunnanensis. Phytochem. 28, 3233-3234. https://doi.org/10.1016/0031-9422(89)80315-2
  12. EI-Feraly FS, Chan YM, Capiton GA, Doskotch RW, Fairchild EH. (1979) Isolation and characterization of peroxycostunolide (verlotorin) and peroxyparthenolide from Magnolia grandiflora. Carbon-13 nuclear magnetic resonance spectroscopy of costunolide and related compounds. J. Org. Chem. 44, 3952-3955 https://doi.org/10.1021/jo01336a041
  13. Greene AE, Muller JC, Ourisson G. (1974) Conversions of alpha-methyl to alpha-methylene-gamma-lactones. Synthesis of two allergenic sesquiterpene lactones. (-)-frullanolide and (+)-arbusculine B. J. Org. Chem. 39, 186-191 https://doi.org/10.1021/jo00916a014
  14. Kim MJ, Oh HJ, Baek SH.(2005) Isolation and biological activity of sesquiterpene lactone. Kor. J. Orien. Physiol. Pathol. 19, 1375-1378
  15. Kraut L, Mues R, Sim-Sim M. (1994) Sesquiterpene lactones and 3-benzylphthalides from Frullania muscicola. Phytochem. 37, 1337-1346 https://doi.org/10.1016/S0031-9422(00)90409-6
  16. Kim YC, Bolzani VDS, Baj N, Gunatilaka AAL, Kingston DGI. (1996) A DNA-damaging sesquiterpene and other constituents from Frullania nisquallensis. Planta Med. 62, 61-63 https://doi.org/10.1055/s-2006-957800
  17. Kim MJ, Baek SH (2006) Antifungal activity of (-)-entcostunolide on the dermatophytic fungus Trichophyton mentagrophytes, Kor. J. Orien. Physiol. Pathol. 20, 467-470
  18. Kim MJ, Lee JS, Baek SH (2009) In vitro cytotoxic activity of (-)-ent-costunolide. Orien. Pharm. Exp. Med. 9, 97-99, 2009 https://doi.org/10.3742/OPEM.2009.9.1.097
  19. Kupchan SM, Eakin MA, Thomas AM. (1971) Tumor inhibitors. 69. Structure.cytotoxicity relations among the sesquiterpene lactones. J. Med. Chem. 14, 1147-1152 https://doi.org/10.1021/jm00294a001
  20. Lee, K.H., Hall, I.H., Mar, E.C., Starnes, C.O., ElGebaly, S.A., Waddell, T.G., Hadg aft, R.I., Ruffner, C.G., Weidner, I., 1997. Sesquiterpene antitumor agents: inhibitors of cellular metabolism. Science (Wash. DC) 196, 533.535 https://doi.org/10.1126/science.191909
  21. Lyss, G., Knorre, A., Schmidt, T.J., Pahl, H.L., Merfort, I., 1998. The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-nB by directly targeting p65. J. Biol. Chem. 273, 33508.33516 https://doi.org/10.1074/jbc.273.50.33508
  22. Park HJ, Jung WT, Basnet P, Kadota S, Namba T. (1996) Syringin 4-O-$\beta$-glucoside,a new phenylpropanoid glycoside, and costunolide, a nitrite oxide synthase inhibitor, from the stem bark of Magnolia sieboldii. J. Nat. Prod. 59, 1128-1130 https://doi.org/10.1021/np960452i
  23. Shin JH, Oh HJ, Park NK, Kim YH, Jeong JH, Lee JH, Baek SH. (2001): Isolation of cytotoxic component from Trichocolea hatcheri. Orient. Pharm. Exp. Med. 1, 49-56
  24. Stocking EM, Williams RM (2003): Chemistry and biology of biosynthetic Diels-Alder reactions, Angew. Chem., Int. Ed. 42, 3078.3155 https://doi.org/10.1002/chin.200340294
  25. Schmidt, T.J., 1997. Rates and stereochemistry in the reaction of helenalin and related helenanolides with sulfhydryl containing biomolecules. Bioorg. Med. Chem. 5, 645.653 https://doi.org/10.1016/S0968-0896(97)00003-5
  26. Zhang S, Won YK, Ong CN, Shen HM (2005): Anticancer potential of sesquiterpene lactones: bioactivity and molecular mechanisms. Curr. Med. Chem. Anticancer Agents. 5, 239-249 https://doi.org/10.2174/1568011053765976