Antifungal activity of alkyl and heterocyclic aza-derivatives of gossypol as well as their complexes with NaClO4 against Fusarium oxysporum f. sp. lupini.
Eight alkyl and six heterocyclic aza-derivatives of gossypol (2-15) have been synthesized using gossypol (1) extracted from Gossypium Herbaceum cottonseeds. The ability of gossypol aza-derivatives to form complexes with NaClO(4) has been investigated by electrospray ionisation (ESI) mass spectra recorded in the positive and negative ion detection modes. The gossypol aza-derivatives have been characterized by FT-IR, (1)H and (13)C NMR spectroscopic methods and subsequently tested for their antifungal properties against Fusarium oxysporum. Four alkyl aza-derivatives (2-5), present in the enamine-enamine tautomeric form, have shown activity comparable or higher than that of gossypol against this fungus. To improve the antifungal activity the complexes of the most active compounds 2-5 with NaClO(4) were prepared. Complexes of 2 and 5 with NaClO(4) have shown antifungal activity higher than that of the uncomplexed compounds.
Przybylski
Piotr
P
Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland. piotrp@amu.edu.pl
Pyta
Krystian
K
Remlein-Starosta
Dorota
D
Schroeder
Grzegorz
G
Brzezinski
Bogumil
B
Bartl
Franz
F
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005670:Fusarium / Q000187:drug effects*; D003368:Gossypium / Q000737:chemistry; D006072:Gossypol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010472:Perchlorates / Q000737:chemistry*; D017670:Sodium Compounds / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D000935:Antifungal Agents; D001372:Aza Compounds; D010472:Perchlorates; D017670:Sodium Compounds; C031068:sodium perchlorate; D006072:Gossypol