Regular ArticleInterference of the Natural Product 7-Oxo-7-deacetoxygedunin (cas 13072-74-7) with CF0of H+-ATPase of Spinach Chloroplasts☆☆☆★★★

Add time:09/10/2019    Source:sciencedirect.com

7-Oxo-7-deacetoxygedunin (cas 13072-74-7), a limonoid isolated fromGuarea grandiflora(Meliaceae) has been found to act as an inhibitor of photophosphorylation in spinach thylakoids. ATP synthesis and phosphorylating electron flows were inhibited by 88 and 83%, respectively, at 300 μM of 7-oxo-7-deacetoxygedunin without affecting proton uptake, basal and uncoupled electron transports. The ketone group of 7-oxo-7-deacetoxygedunin is an important structural requirement for the displayed inhibitory activity on chloroplast H+-ATPase, since gedunin possessing a 7α-acetoxy group was a less potent energy transfer inhibitor. The light-activated membrane bound Mg2+-ATPase and the heat-activated Ca2+-ATPase of the isolated coupling factor were insensitive to 7-oxo-7-deacetoxygedunin. 7-oxo-7-deacetoxygedunin shows a competitive kinetic behavior with 5-O-β-D-galactopyranosyl-7-methoxy-3′,4′-dihydroxy-4-phenylcoumarin when they inhibit H+-ATPase activity, but a noncompetitive kinetic with DCCD. These results suggest that 7-oxo-7-deacetoxygedunin and the 4-phenylcoumarin have the same surrounding site of inhibition in C0. Ki for 7-oxo-7-deacetoxygedunin, 4-phenylcoumarin, and DCCD were 146, 220, and 10 μM, respectively.

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