New rubrolide analogues as inhibitors of photosynthesis light reactions.
Natural products called rubrolides have been investigated as a model for the development of new herbicides that act on the photosynthesis apparatus. This study comprises a comprehensive analysis of the photosynthesis inhibitory ability of 27 new structurally diverse rubrolide analogues. In general, the results revealed that the compounds exhibited efficient inhibition of the photosynthetic process, but in some cases low water solubility may be a limiting factor. To elucidate their mode of action, the effects of the compounds on PSII and PSI, as well as their partial reaction on chloroplasts and the chlorophyll a fluorescence transients were measured. Our results showed that some of the most active rubrolide analogues act as a Hill reaction inhibitors at the QB level by interacting with the D1 protein at the reducing side of PSII. All of the active analogues follow Tice's rule of 5, which indicates that these compounds present physicochemical properties suitable for herbicides.
Department of Chemistry, Universidade Federal de Viçosa, Av. P.H. Rolfs, s/n, 36570-000 Viçosa, MG, Brazil.
Jodieh O S
JO
Varejão
Department of Chemistry, Universidade Federal de Viçosa, Av. P.H. Rolfs, s/n, 36570-000 Viçosa, MG, Brazil; Department of Chemistry, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Campus Pampulha, CEP 31270-901 Belo Horizonte, MG, Brazil. Electronic address: lcab@ufmg.br.
Luiz C A
LC
Barbosa
Department of Biochemistry, School of Chemistry, National Autonomous University of México, México, D.F. C.P. 04510, Mexico.
Gabriela Álvarez
GÁ
Ramos
Department of Chemistry, Universidade Federal de Viçosa, Av. P.H. Rolfs, s/n, 36570-000 Viçosa, MG, Brazil.
Eduardo V V
EV
Varejão
Department of Biochemistry, School of Chemistry, National Autonomous University of México, México, D.F. C.P. 04510, Mexico.
Beatriz
B
King-Díaz
Department of Biochemistry, School of Chemistry, National Autonomous University of México, México, D.F. C.P. 04510, Mexico.
Blas
B
Lotina-Hennsen
D002734:Chlorophyll / Q000737:chemistry; D000077194:Chlorophyll A; D002736:Chloroplasts / Q000378:metabolism; D004579:Electron Transport; D005663:Furans / Q000737:chemistry* / Q000378:metabolism / Q000633:toxicity; D006540:Herbicides / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity; D008027:Light; D010788:Photosynthesis / Q000187:drug effects / Q000528:radiation effects; D045331:Photosystem I Protein Complex / Q000037:antagonists & inhibitors* / Q000378:metabolism; D045332:Photosystem II Protein Complex / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D018724:Spinacia oleracea / Q000378:metabolism
D005663:Furans; D006540:Herbicides; D045331:Photosystem I Protein Complex; D045332:Photosystem II Protein Complex; D002734:Chlorophyll; D000077194:Chlorophyll A