Characterization and synthesis of volatile compounds from the defensive secretions of some "daddy longlets" (Arachnida: Opiliones: Leiobunum spp.).

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Abstract
Analyses of the chief volatile constituents of the defensive secretions of 3 opilionids were carried out. L. nigripalpi produces 3 closely related C7 compounds: E-4-methyl-4-hexen-3-one(I), 4-methylhexan-3-one(II), and 4-methylhexan-3-ol(III), along with E-4-methyl-4-hepten-3-one(IV), E,E-2,4-dimethylhexa-2,4-dienal(IX), and a minor, unidentified component. L. leiopensis secretion contains E-4-methyl-4-hepten-3-one(IV), 4-methylheptan-3-one(V), E,E-2,4-dimethylhexa-2,4-dien-1-ol(VII), and E,E-2,4-dimethylhepta-2,4-dien-1-ol(VIII). L. calcar yields chiefly E-4,6-dimethyl-6-octen-3-one(VI) and E,E-2,4-dimethylhexa-2,4-dien-1-ol(VII). Of these compounds, 6 are new natural products. The structures of these compounds, which can be regarded either as polyketide-derived or as modified isoprenoids, raise interesting biosynthetic questions.

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