Evaluation of the anticancer activities of two fungal polycyclic ethanones, alternethanoxins A and B, and two of their derivatives

  • Authors:
    • Marina Bury
    • Biancavaleria Punzo
    • Alexander Berestetskiy
    • Benjamin Lallemand
    • Jacques Dubois
    • Florence Lefranc
    • Véronique Mathieu
    • Anna Andolfi
    • Robert Kiss
    • Antonio Evidente
  • View Affiliations

  • Published online on: January 1, 2011     https://doi.org/10.3892/ijo_00000842
  • Pages: 227-232
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Abstract

Alternethanoxins A (1) and B (2) are fungal phytotoxins that are produced by Alternaria sonchi and have been recently characterized as new polycyclic ethanones. Triacetyl (3) and dimethyl (4) derivatives of compound 1 were evaluated together with alternethanoxins for their in vitro growth inhibitory activities in five human and one mouse cancer cell lines in comparison to the reference compound temozolomide (TMZ). Compounds 1-4 and TMZ displayed similar growth inhibitory activities, and these anticancer activities were equivalent in cancer cell lines that display certain levels of resistance to pro-apoptotic stimuli and those that are sensitive to pro-apoptotic stimuli. Of the six cancer cell lines under study, the human esophageal cancer cell line OE21 was the most sensitive to the four polycyclic ethanones. Computer-assisted phase-contrast microscopy (quantitative videomicroscopy) revealed that compounds 1, 2 and 4 displayed cytostatic rather than cytotoxic growth inhibitory effects, while compound 3 appeared to have cytotoxic effects. Thus, this study creates a stimulus for further structure-activity investigations with respect to the anticancer activities of compounds belonging to the alternethanoxin group. The observed toxicity does not seem to be affected by the stereochemistry of C-6 of the B ring, the presence of a hydroxy group at C-1 or the presence of a furan ring joining rings A and C in alternethanoxin B. The anticancer activity (cytostatic versus cytotoxic) of this type of compound could be affected by the chemical moieties present at the hydroxy groups at C-4 and C-6, as was observed for the cytostatic and cytotoxic activities of derivatives 4 and 3, respectively.

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January 2011
Volume 38 Issue 1

Print ISSN: 1019-6439
Online ISSN:1791-2423

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APA
Bury, M., Punzo, B., Berestetskiy, A., Lallemand, B., Dubois, J., Lefranc, F. ... Evidente, A. (2011). Evaluation of the anticancer activities of two fungal polycyclic ethanones, alternethanoxins A and B, and two of their derivatives. International Journal of Oncology, 38, 227-232. https://doi.org/10.3892/ijo_00000842
MLA
Bury, M., Punzo, B., Berestetskiy, A., Lallemand, B., Dubois, J., Lefranc, F., Mathieu, V., Andolfi, A., Kiss, R., Evidente, A."Evaluation of the anticancer activities of two fungal polycyclic ethanones, alternethanoxins A and B, and two of their derivatives". International Journal of Oncology 38.1 (2011): 227-232.
Chicago
Bury, M., Punzo, B., Berestetskiy, A., Lallemand, B., Dubois, J., Lefranc, F., Mathieu, V., Andolfi, A., Kiss, R., Evidente, A."Evaluation of the anticancer activities of two fungal polycyclic ethanones, alternethanoxins A and B, and two of their derivatives". International Journal of Oncology 38, no. 1 (2011): 227-232. https://doi.org/10.3892/ijo_00000842