Antifeedants polygodial

Example A family of biologically active compounds Isolated from African trees include polygodial (39), an antifeedant which protects the tree against plagues of caterpillars. ... 

Polygodial Warburgia stuhlmanii (Canellaceae), Insect antifeedant [pepper... 

The potent biological activity (insect antifeedant, antitumour, antifungal) of warburganal (35) has stimulated considerable synthetic interest in this compound. Three total syntheses of this compound have been recorded in the period under review. " The synthesis by Tanis and Nakanishi has additional flexibility since the key intermediate diol (34) can be used in the syntheses of cinnamolide (36), drimenin (37), and polygodial (38). Both norisoambreinolide (39 R = O) and isoambrox (39 R = H2) have been synthesized from (40), the product of the stannic chloride-catalysed cyclization of farnesyl phenyl sulphone. Yahazunol (41), a bicyclofarnesyl hydroquinone, has been identified in the brown seaweed... 

Moreno-Osorio, L., Cortes, M., Armstrong, V., Bailen, M. and Gonzalez-Coloma, A. (2008) Antifeedant activity of some polygodial derivatives. Z. Naturforsch. C, 63, 215-20. 

K. Mori and H. Watanabe, Synthesis of both the enantiomers of polygodial, an insect antifeedant sesquiterpene. Tetrahedron, 42 (1986) 273-281. 

When Mr. Watanabe (now Prof. Watanabe at the University of Tokyo) and I tasted the synthetic samples, both (—)-64 and (+)-64 were extremely hot-tasting. Examination of piscicidal activity by Prof. Asakawa and that of antifeedant activity by Prof. Pickett showed no difference between the enantiomers of polygodial. In this particular case, both the enantiomers 64 and 64 showed the same bioactivity.44... 

A variety of drimane-type sesquiterpenes occur in the plant Polygonum hydropiper which is also known as water pepper [88-90]. The main constituents of the leaves and seed are (-)-polygodial (22) and (-)-tadeonal drime-7-en-l 1,12-dial. These compounds were found to be cytotoxic and inhibit plant growth [91]. The synthesis of polygodial (22), an antifeedant and antimicrobial agent [92], can be formed in a few steps from (2E, 6E)-famesyl pyrophosphate, 53 [93]. The intermediate of the reaction is drimenol (54) (Scheme 1). 

Polygodial (48) also occurs in the mantle of a dorid nudi-branch Dendrodoris limbata and has antifeedant properties against a number of marine and freshwater fish. This sesquiterpene defensive compound is synthesized by the nudi-branch, in contrast to the protective compounds of most nu-dibranchs that are taken from the sponges on which they feed (Harbome, 1986b). 

DTschia, M., G. Prota, and G. Sodano Reaction of Polygodial with Primary Amines An Alternative Explanation to the Antifeedant Activity. Tetrahedron Lett. 23, 3295 (1982). 

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