Tricolorin A, (11
S)-11-hydroxyhexadecanoic acid 11-
O-
α-l- rhamnopyranosyl-(1→3)-
O-
α-l-{2-
O-(2
S-methylbutanoyl)-4-
O-(2
S-methylbutanoyl)}-rhamnopyranosyl-(1→2)-
O-
β-d-glucopyranosyl-(1→2)-
β-fucopyranoside-(1,3′′-lactone), the major phytogrowth inhibitor isolated from
Ipomoea tricolor Cav. (Convolvulaceae) was found to be a potent uncoupler (U50=0.33 μ
M) of photophosphorylation in spinach chloroplasts. Tricolorin A inhibited H+-uptake and adenosine 5′-triphosphate (ATP) synthesis, and stimulated basal and phosphorylating electron flows. Using a combination of two well-known fluorescent ΔpH probes, 9-aminoacridine and 9-amino-6-chloro-2-methoxyacridine, the uncoupling behavior of tricolorin A was also demonstrated for submitochondrial particles. Polarographic data showed that high concentrations (20 μ
M) of tricolorin A inhibited photosystem II (PSII) electron flow at the level of plastoquinone B (QB). Chlorophyll (Chl)
a fluorescence analysis showed that tricolorin A induced accumulation of QA− and strongly decreased the electron transport capacity, suggesting that the target of this molecule was located at the QB level. The macrocyclic lactone-type structure of this allelopathic agent proved to be an important structural requirement for uncoupling activity since its hydrolysis caused loss of the inhibitory potential.