Structure-Function Analysis of Volatile (Z)-3-Fatty Alcohols in Tomato

Plants emit green leaf volatiles (GLVs) in response to biotic and abiotic stress. Receiver plants perceive GLVs as alarm cues resulting in activation of defensive or protective mechanisms. While this is well documented, it is not known how GLVs are perceived by receiver cells and what the structural determinants are for GLV activity. We tested whether the carbon chain length in (Z)-3-fatty alcohols with four to nine carbons and the double bonds in six-carbon alcohols contribute to bioactivity. In Solanum peruvianum suspension-cultured cells we found that (Z)-3-fatty alcohols, except (Z)-3-butenol, induce medium alkalinization and MAP kinase phosphorylation, two signaling responses often tied to the perception of molecular patterns that function in plant immunity and resistance to herbivores. In tomato (S. lycopersicum) seedlings, we found that (Z)-3-fatty alcohols induce inhibition of root growth. In both signaling and physiological responses, (Z)-3-octenol and (Z)-3-nonenol had a higher bioactivity than (Z)-3-heptenol and (Z)-3-hexenol, with (Z)-3-butenol only being active in root growth assays. Bioactivity correlated not only with chain length but also with lipophilicity of the fatty alcohols. The natural GLVs (E)-2-hexenol and the saturated 1-hexanol exhibited a higher bioactivity in pH assays than (Z)-3-hexenol, indicating that the presence and position of a double bond also contributes to bioactivity. Our results indicate that perceiving mechanisms for (Z)-3-fatty alcohols show a preference for longer chain fatty alcohols or that longer chain fatty alcohols are more accessible to receptors.