Electron transport inhibitor in Cyperus javanicus.
The natural quinone, hydroxydietrichequinone (3-heptadec-8-enyl-2-hydroxy-5-methoxy-[1,4]benzoquinone) is a secondary metabolite of Cyperus javanicus. We found that this quinone inhibited both mitochondrial respiration and photosynthesis in their electron transportation systems. The quinone was found to have a mode of action against the ubiquinone reductase site from the results of different electron donor experiments on intact mitochondria from rat liver. The electron transport system, photosystem-II (PS-II), in chroloplast from spinach leaves was inhibited by the quinone in a similar way to that of the triazin sires herbicide, atrazin, with its mode of action against PS II. This natural quinone has a long aliphatic chain (C17) including an unsaturated bond at its midpoint. We recognized 8-9 unsaturated bonds in the aliphatic chain from an MS analysis of the methylthio-addact, and spectral data presumed a configuration of cis. form.
Morimoto
M
M
Department of Agricultural Chemistry, Faculty of Agriculture, Kinki University, Nakamachi, Nara, Japan.
Shimomura
Y
Y
Mizuno
R
R
Komai
K
K
D000818:Animals; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002855:Chromatography, Thin Layer; D029785:Cyperaceae / Q000737:chemistry*; D004579:Electron Transport / Q000187:drug effects*; D066298:In Vitro Techniques; D008099:Liver / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008930:Mitochondria, Liver / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism; D010101:Oxygen Consumption / Q000187:drug effects; D010946:Plants, Medicinal / Q000737:chemistry*; D051381:Rats; D017208:Rats, Wistar; D013055:Spectrophotometry, Infrared
D016227:Benzoquinones; C448764:hydroxydietrichequinone