Mexican propolis flavonoids affect photosynthesis and seedling growth

• Flavonoids isolated from Mexican propolis were identified by NMR and mass techniques.
• Acacetin acts as an uncoupler on spinach leaves chloroplasts.
• Chrysin and 4′,7-dimethylnarangenin inhibit the PS II acceptor side of photosynthesis.
• Acacetin, chrysin and 4′,7-dimethylnarangenin are inhibitors of seedling growth.

As a continuous effort to find new natural products with potential herbicide activity, flavonoids acacetin (1), chrysin (2) and 4′,7-dimethylnarangenin (3) were isolated from a propolis sample collected in the rural area of Mexico City and their effects on the photosynthesis light reactions and on the growth of Lolium perenne, Echinochloa crus-galli and Physalis ixocarpa seedlings were investigated. Acacetin (1) acted as an uncoupler by enhancing the electron transport under basal and phosphorylating conditions and the Mg2+-ATPase. Chrysin (2) at low concentrations behaved as an uncoupler and at concentrations up to 100 μM its behavior was as a Hill reaction inhibitor. Finally, 4′,7-dimethylnarangenin (3) in a concentration-dependent manner behaved as a Hill reaction inhibitor. Flavonoids 2 and 3 inhibited the uncoupled photosystem II reaction measured from water to 2,5-dichloro-1,4-benzoquinone (DCBQ), and they did not inhibit the uncoupled partial reactions measured from water to sodium silicomolybdate (SiMo) and from diphenylcarbazide (DPC) to diclorophenol indophenol (DCPIP). These results indicated that chrysin and 4′,7-dimethylnarangenin inhibited the acceptor side of PS II. The results were corroborated with fluorescence of chlorophyll a measurements. Flavonoids also showed activity on the growth of seedlings of Lolium perenne and Echinochloa crus-galli.

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