The Fungal Phytotoxin Alternariol 9‑Methyl Ether and Some of Its Synthetic Analogues Inhibit the Photosynthetic Electron Transport Chain

Abstract

Alternariol and monomethylalternariol are natural phytotoxins produced by some fungal strains, such as <i>Nimbya</i> and <i>Alternaria</i>. These substances confer virulence to phytopathogens, yet no information is available concerning their mode of action. Here we show that in the micromolar range alternariol 9-methyl ether is able to inhibit the electron transport chain (IC₅₀ = 29.1 ± 6.5 μM) in isolated spinach chloroplasts. Since its effectiveness is limited by poor solubility in water, several alternariol analogues were synthesized using different aromatic aldehydes. The synthesized 6<i>H</i>-benzo­[<i>c</i>]­cromen-6-ones, 5<i>H</i>-chromene­[4,3-<i>b</i>]­pyridin-5-one, and 5<i>H</i>-chromene­[4,3-<i>c</i>]­pyridin-5-one also showed inhibitory properties, and three 6<i>H</i>-benzo­[<i>c</i>]­cromen-6-ones were more effective (IC₅₀ = 12.8–22.8 μM) than the lead compound. Their addition to the culture medium of a cyanobacterial model strain was found to inhibit algal growth, with a relative effectiveness that was consistent with their activity <i>in vitro</i>. In contrast, the growth of a nonphotosynthetic plant cell culture was poorly affected. These compounds may represent a novel lead for the development of new active principles targeting photosynthesis