Bioactive Constituents of Conyza albida

Abstract

The bioactivity-guided fractionation of an active chloroform extract of Conyza albida led to the isolation of three alkenynes, deca-4,6-diyn-2-(Z)-enoic methyl ester (1), deca-4,6-diyn-2-(Z)-enoic ethyl ester (2) and deca-2,4-diene-4-hydroxy-6-yn-1,4-olide (3), and the terpenoid spathulenol (4), as the active toxic metabolites in the Artemia sp. lethality test. When tested in the KB cell cytotoxicity assay, compounds 1 - 4 demonstrated IC₅₀ values of 52.2, 38.4, 117.9, and 83.8 μM, respectively. All compounds studied were inactive in the DNA methyl green and DNA strand scission assays, while compounds 3 and 4 showed moderate activity as inhibitors of human topoisomerase I. Compound 2 is reported here for the first time.

Key words

Conyza albida - Compositae - alkenynes - cytotoxic activity - topoisomerase I - DNA interaction - DNA strand scission

References

• 1 Ariza Espinar L. Conyza albida (Compositae) en Argentina.  Boletín de la Sociedad Argentina de Botánica. 1982;  21 269-71
• 2 Marzocca A. Conyza bonariensis. Vademécum de Malezas Medicinales de la Argentina, Indígenas y Exóticas. Editorial Hemisferio Sur Buenos Aires, Argentina; 1997: 259
• 3 González A, Ferreira F, Vázquez A, Moyna P, Alonso Paz E. Biological screening of Uruguayan medicinal plants.  Journal of Ethnopharmacology. 1993;  39 217-20
• 4 Gutierrez-Lugo M T, Barrientos-Benitez T, Luna B, Ramirez-Gamma R M, Bye R, Linares E, Mata R. Antimicrobial and cytotoxic activities of some crude drug extracts from Mexican medicinal plants.  Phytomedicine. 1996;  2 341-7
• 5 Al-Yahya M A, Mossa J S, Al-Meshal I A, Antoun M D, Mc Cloud T G, Cassady J M, Jacobsen L B, McLaughlin J L. Phytochemical and biological studies on Saudi medicinal plants part 9. Antitumor testing.  International Journal of Crude Drug Research. 1985;  23 45-66
• 6 Anderberg A A. Taxonomy and phylogeny of the tribe Plucheeae (Asteraceae).  Plant Systematic Evolution. 1991;  176 145-77
• 7 Bohlmann F, Jakupovic J. 8-Oxo-α-selinen und neue Scopoletin-derivate aus Conyza-arten.  Phytochemistry. 1979;  18 1367-70
• 8 Sanz J F, Marco J A. Ein neues Butenolid aus Conyza bonariensis .  Liebigs Annalen Chemie. 1991;  399-400
• 9 Krebs H C, Rakotoarimanga J V, Habermehl G G. Isolation of spathulenol and (-)-caryophyllene oxide from Vernonia mollissima Don and ¹H and ¹³C reassignment by two-dimensional NMR spectroscopy.  Magnetic Resonance in Chemistry. 1990;  28 124-8
• 10 Mongelli E, Romano A, Desmarchelier C, Coussio J, Ciccia G. Cytotoxic 4-nerolidylcatechol from Pothomorphe peltata inhibits topoisomerase I activity.  Planta Medica. 1999;  65 376-8
• 11 McLaughlin J. Methods in Plant Biochemistry. Crown gall tumors on potato discs and brine shrimp lethality: two bioassays for higher plant screening and fractionation. In: Harborne JB, editor . Academic Press New York; 1991: 1-32
• 12 Sugiyama H, Ehrenfeld G N, Shipley J B, Kilkuskie R E, Chang L H, Hecht S M. DNA strand scission by bleomycin group antibiotics.  Journal of Natural Products. 1985;  48 869-77
• 13 Carpita A, Neri D, Rossi R. Stereocontrolled synthesis of naturally-occurring poliacetylenes characterized by (E)-1-en-3-yne, (E)-1-en-3,5-diyne, (1E,5E)-1,5-dien-3-yne, and (1E,7E)-1,7-dien-3,5-diyne moieties.  Gazzetta Chimica Italiana. 1987;  117 481-97
• 14 Miyazawa M, Yamamoto K, Kameoka H. The essential oil of Erigeron canadensis .  Journal of Essential Oil Research. 1992;  4 227-30
• 15 Köning G, Wright A, Sticher O, Angerhofer C, Pezzuto J. Biological activities of selected marine natural products.  Planta Medica. 1994;  60 532-7
• 16 Fullas F, Hussain R A, Chai H B, Pezzuto J M, Soejarto D D, Kinghorn A D. Cytotoic constituents of Baccharis gaudichaudiana .  Journal of Natural Products. 1994;  57 801-7
• 17 Bonjean K, De Pauw-Gillet M, Bassleer R, Quentin-Leclercq J, Angenot L, Wright A. Cytotoxic activities of Colombian plant extracts on Chinense hamster lung fibroblasts.  Phytotherapy Research. 1996;  10 159-60
• 18 Suffness M, Pezzuto J. Methods in Plant Biochemistry. Assays related to cancer drug discovery. In: Harborne JB, editor Academic Press New York; 1991: 71-133
• 19 Liu L F. DNA Topoisomerase poisons as antitumor drugs.  Annual Review of Biochemistry. 1989;  58 351-75
• 20 Jung J H, Kim Y, Lee C O, Kang S S, Park J H, Im K S. Cytotoxic constituents of Saussurea lappa .  Archives of Pharmaceutical Research. 1998;  21 153-56
• 21 Takaishi Y, Okuyama T, Masuda A, Nakano K, Murakami K, Tomimatsu T. Acetylenes from Cirsium japonicum .  Phytochemistry. 1990;. 29 3849-52