title: Characterization and synthesis of volatile compounds from the defensive secretions of some "daddy longlets" (Arachnida: Opiliones: Leiobunum spp.).
abstract: Analyses of the chief volatile constituents of the defensive secretions of three oplionids were carried out. Leiobunum nigripalpi produces three 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. leiopenis 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). Six of these compounds 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.
mesh_terms: D000438:Alcohols / Q000502:physiology; D000818:Animals; D001097:Arachnida / Q000502:physiology*; D002849:Chromatography, Gas; D005260:Female; D007659:Ketones / Q000502:physiology; D008297:Male; D013058:Mass Spectrometry; D013045:Species Specificity
chemical_list: D000438:Alcohols; D007659:Ketones
references.citation: Proc Natl Acad Sci U S A. 1971 Jul;68(7):1467-8
references.pmid: 5283937
references.citation: Science. 1975 May 16;188(4189):734-6
references.pmid: 1124395