Use este identificador para citar ou linkar para este item: https://locus.ufv.br//handle/123456789/19088
Tipo: Artigo
Título: Synthetic analogues of the natural compound cryphonectric acid interfere with photosynthetic machinery through two different mechanisms
Autor(es): Teixeira, Róbson Ricardo
Pereira, Wagner Luiz
Tomaz, Deborah Campos
Oliveira, Fabrício Marques de
Giberti, Samuele
Forlani, Giuseppe
Abstract: A series of isobenzofuran-1(3H)-ones (phthalides), analogues of the naturally occurring phytotoxin cryphonectric acid, were designed, synthesized, and fully characterized by NMR, IR, and MS analyses. Their synthesis was achieved via condensation, aromatization, and acetylation reactions. The measurement of the electron transport chain in spinach chloroplasts showed that several derivatives are capable of interfering with the photosynthetic apparatus. Few of them were found to inhibit the basal rate, but a significant inhibition was brought about only at concentrations exceeding 50 μM. Some other analogues acted as uncouplers or energy transfer inhibitors, with a remarkably higher effectiveness. Isobenzofuranone addition to the culture medium inhibited the growth of the cyanobacterium Synechococcus elongatus, with patterns consistent with the effects measured in vitro upon isolated chloroplasts. The most active derivatives, being able to completely suppress algal growth at 20 μM, may represent structures to be exploited for the design of new active ingredients for weed control.
Palavras-chave: Herbicides
Isobenzofuran-1(3H)-ones
Photosynthetic electron transport
Phtalides
Uncouplers
Editor: Journal of Agricultural and Food Chemistry
Tipo de Acesso: American Chemical Society
URI: https://www.ncbi.nlm.nih.gov/pubmed/23678958
http://www.locus.ufv.br/handle/123456789/19088
Data do documento: 17-Mai-2013
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