Download PDF
Planta Med 2011; 77(17): 1912-1915
DOI: 10.1055/s-0031-1279994
Biological and Pharmacological Activity
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Furanogermacranolides from the Flowers of Helianthus angustifolius

Nadine Kretschmer1 , Martina Blunder1 , Olaf Kunert2 , Gerald N. Rechberger3 , Rudolf Bauer1 , Wolfgang Schuehly1
  • 1Department of Pharmacognosy, Institute of Pharmaceutical Sciences, Karl-Franzens-University Graz, Graz, Austria
  • 2Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, Karl-Franzens-University Graz, Graz, Austria
  • 3Institute of Molecular Biosciences, Karl-Franzens-University Graz, Graz, Austria
Further Information

Publication History

received March 10, 2011 revised May 17, 2011

accepted May 21, 2011

Publication Date:
14 June 2011 (online)

    Permissions and Reprints

Abstract

The dichloromethane extract of the flowers of Helianthus angustifolius L. (Asteraceae, Heliantheae) was investigated in vitro for its cytotoxic activity using human cancer cell lines: CCRF-CEM leukemia, MDA-MB-231 breast cancer, U251 glioblastoma, HCT 116 colon cancer cells, and the human lung fibroblast cell line MRC-5. Cytotoxicity-guided fractionation led to the isolation of four related heliangolide-type sesquiterpene lactones. The structures were elucidated by means of NMR spectroscopy and high-resolution mass spectrometry. Of the investigated compounds, 8-methacrylyl-4,15-iso-atriplicolide (1) showed the highest activity against all tested cancer cell lines with IC50 values ranging from 0.26 ± 0.01 µM for CCRF-CEM cells to 4.22 ± 0.26 µM for MRC-5 cells.

Key words

Helianthus angustifolius - Asteraceae - heliangolide - isoatriplicolide - cancer cell lines - MRC-5 lung fibroblast cells

Supporting Information

References

  • 1 Radford A E, Ahles H E, Bell C R. Manual of the vascular flora of the Carolinas. Chapel Hill: The University of North Carolina Press; 1964: 1113
    Google Scholar
  • 2 Correll D S, Johnston M C. Manual of the vascular plants of Texas. Richardson: The University of Texas at Dallas; 1996: 1650-1653
    Google Scholar
  • 3 Weakley A S. Flora of the Southern and Mid-Atlantic states working draft of 8 March 2010. University of North Carolina; 2010: 844-849
    Google Scholar
  • 4 Ohno N, Mabry T J. Germacranolides in Helianthus mollis.  Phytochemistry. 1979;  18 1003-1006
    CrossrefPubMedGoogle Scholar
  • 5 Watanabe K, Ohno N, Yoshioka H, Gershenzon J, Mabry T J. Sesquiterpene lactones and diterpenoids from Helianthus argophyllus.  Phytochemistry. 1982;  21 709-713
    CrossrefPubMedGoogle Scholar
  • 6 Bohlmann F, Jakupovic J, Kin R M, Robinson H. Neue ent-Atisiren- und ent-Kaurensäure-Derivate aus Helianthus-Arten.  Phytochemistry. 1980;  19 863-868
    CrossrefPubMedGoogle Scholar
  • 7 Waddell T G. Hymenoxin a flavone from Helianthus angustifolius.  Phytochemistry. 1973;  12 2061
    CrossrefPubMedGoogle Scholar
  • 8 Ohno N, Gershenzon J, Neuman P, Mabry T J. Diterpene carboxylic acids and a heliangolide from Helianthus angustifolius.  Phytochemistry. 1981;  20 2393-2396
    CrossrefPubMedGoogle Scholar
  • 9 Zhang S, Won Y-K, Ong C-N, Shen H-M. Anti-cancer potential of sesquiterpene lactones: bioactivity and molecular mechanisms.  Curr Med Chem. 2005;  5 239-249
    PubMedGoogle Scholar
  • 10 Kinghorn A D, Carcache-Blanco E J, Chai H-B, Orjala J, Farnsworth N R, Kramer R A, Rose W C, Emanuel S, Vite G D, Jarjoura J, Cope F O. Discovery of anticancer agents of diverse natural origin.  Pure Appl Chem. 2009;  81 1051-1063
    CrossrefPubMedGoogle Scholar
  • 11 Efferth T, Kahl S, Paulus K, Adams M, Rauh R, Boechzelt H, Hao X, Kaina B, Bauer R. Phytochemistry and pharmacogenomics of natural products derived from traditional Chinese medicine and Chinese materia medica with activity against tumor cells.  Mol Cancer Ther. 2008;  7 152-161
    PubMedGoogle Scholar
  • 12 Gershenzon J, Mabry T J. Furanoheliangolides from Helianthus schweinitzii.  Phytochemistry. 1984;  23 2557-2559
    CrossrefPubMedGoogle Scholar
  • 13 Spring O. Sesquiterpene lactones from Helianthus tuberosus.  Phytochemistry. 1991;  30 519-522
    CrossrefPubMedGoogle Scholar
  • 14 Kupchan S M, Eakin M A, Thomas A M. Tumor inhibitors. 69. Structure-cytotoxicity relationships among the sesquiterpene lactones.  J Med Chem. 1971;  14 1147-1152
    CrossrefPubMedGoogle Scholar
  • 15 Lee K H, Huang E S, Piantadosi C, Pagano J S, Geissman T A. Cytotoxicity of sesquiterpene lactones.  Cancer Res. 1971;  31 1649-1654
    PubMedGoogle Scholar
  • 16 Fischer N H, Lu T, Cantrell C L, Castañeda-Acosta J, Quijano L, Franzblau S G. Antimycobacterial evaluation of germacranolides in honour of Professor G.H. Neil Towers 75th birthday.  Phytochemistry. 1998;  49 559-564
    CrossrefPubMedGoogle Scholar
  • 17 Schmidt T J. Toxic activities of sesquiterpene lactones: structural and biochemical aspects.  Curr Org Chem. 1999;  3 577-608
    PubMedGoogle Scholar
  • 18 Schmidt T J. Quantitative structure-cytotoxicity relationships within a series of helenanolide type sesquiterpene lactones.  Pharm Pharmacol Lett. 1999;  9 9-13
    PubMedGoogle Scholar
  • 19 Seebacher W, Simic N, Weis R, Saf R, Kunert O. Spectral assignments of reference data.  Magn Reson Chem. 2003;  41 636-638
    CrossrefPubMedGoogle Scholar
  • 20 Scudiero D A, Shoemaker R H, Paull K D, Monks A, Tierney S, Nofziger T H, Currens M J, Seniff D, Boyd M. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines.  Cancer Res. 1988;  48 4827-4833
    PubMedGoogle Scholar
  • 21 Rinner B, Kretschmer N, Knausz H, Mayer A, Boechzelt H, Hao X J, Heubl G, Efferth T, Schaider H, Bauer R. A petrol ether extract of the roots of Onosma paniculatum induces cell death in a caspase dependent manner.  J Ethnopharmacol. 2010;  129 182-188
    CrossrefPubMedGoogle Scholar

Dr. Wolfgang Schuehly

Department of Pharmacognosy
Institute of Pharmaceutical Sciences
Karl-Franzens-University Graz

Universitätsplatz 4

8010 Graz

Austria

Phone: +43 316 3 80 55 27

Fax: +43 316 3 80 98 60

Email: wolfgang.schuehly@uni-graz.at

>