Bruchins, plant mitogens from weevils: structural requirements for activity.

Bruchins are 3-hydroxypropanoate esters of long-chain alpha,omega-diols from pea weevils and cowpea weevils that have been shown to initiate callus formation on pea pods at extremely low application rates. Synthetic analogs have been prepared and examined to evaluate structural requirements for inducing this unusual neoplastic response. Chain length (optimum length C22-C24) is important, whereas unsaturation within the chain is relatively unimportant. Difunctionality is required for maximum activity, but the alpha,omega-diols themselves are inactive. Most critical is the ester portion(s) of the molecules; 3-hydroxypropanoate esters are far more active than any analogs examined.