Chemical profiles of scent gland secretions in the cyphophthalmid opilionid harvestmen, Siro duricorius and S. exilis.

Gas chromatographic-mass spectrometric analyses of the scent gland secretions of Siro duricorius and S. exilis (Opiliones, Cyphophthalmi, Sironidae) revealed a set of 24 components, comprising a series of saturated and unsaturated methyl ketones (C11-C15) and four naphthoquinones. Whereas the scent gland secretions of S. duricorius, collected in Austria, and S. exilis from USA were qualitatively nearly indistinguishable (with the exception of acetophenone that was specific to S. duricorius), they distinctly differed in their relative quantitative compositions: major components of the secretion of S. duricorius were 7-tridecen-2-one, tridecan-2-one, undecan-2-one, 1,4-naphthoquinone, 6-methyl-1,4-naphthoquinone (tentatively identified only), and 4-chloro-1,2-naphthoquinone. In contrast, in S. exilis a compound tentatively identified as 6-methyl-4-chloro-1,2-naphthoquinone was present in large amounts (in S. duricorius a trace component), whereas undecan-2-one only occurred in minor quantities. Secretion profiles of juveniles and adults (both sexes) of each species showed high correspondence. This is the first report on the chemistry of scent gland secretions of the opilionid suborder Cyphophthalmi. 4-Chloro-1,2-naphthoquinone was identified as a new exocrine product of arthropods, whereas 1,4-naphthoquinone and the tentatively identified 6-methyl-1,4-naphthoquinone are known constituents of exocrine secretions from one species of palpatorid opilionids, Phalangium opilio. In contrast, all ketones identified were new for opilionid scent glands, although similar ketones are characteristic of scent gland secretions of palpatorid genera Leiobunum and Hadrobunus. With regard to the near-basic position of Cyphophthalmi in currently proposed phylogenetic trees of Opiliones, naphthoquinones and ketones from Siro may represent the condition ancestral to the (derived) naphthoquinone- and ketone-rich secretions in phalangid Palpatores.