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CHEMICAL PROFILES of SCENT GLAND SECRETIONS in the CYPHOPHTHALMID OPILIONID HARVESTMEN, Siro Duricorius and S

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CHEMICAL PROFILES of SCENT GLAND SECRETIONS in the CYPHOPHTHALMID OPILIONID HARVESTMEN, Siro Duricorius and S Journal of Chemical Ecology, Vol. 31, No. 6, June 2005 ( #2005) DOI: 10.1007/s10886-005-5291-4 CHEMICAL PROFILES OF SCENT GLAND SECRETIONS IN THE CYPHOPHTHALMID OPILIONID HARVESTMEN, Siro duricorius AND S. exilis GUENTHER RASPOTNIG,1,2,* GUENTER FAULER,2 MATTHIAS LEIS,2 and HANS-JOERG LEIS2 1Institute of Zoology, Karl-Franzens-University, Universitaetsplatz 2, 8010 Graz, Austria 2Department of Biochemical Analysis and Mass Spectrometry, University Children’s Hospital, Auenbruggerplatz 30, 8036 Graz, Austria (Received December 15, 2004; accepted February 1, 2005) Abstract—Gas chromatographicYmass 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 (C11YC15) 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 identi- fied as a new exocrine product of arthropods, whereas 1,4-naphthoquinone and the tentatively identified 6-methyl-1,4-naphthoquinone are known con- stituents 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 *To whom correspondence should be addressed. E-mail: [email protected] 1353 0098-0331/05/0600-1353/0 # 2005 Springer Science + Business Media, Inc. 1354 RASPOTNIG ET AL. trees of Opiliones, naphthoquinones and ketones from Siro may represent the condition ancestral to the (derived) naphthoquinone- and ketone-rich secretions in phalangid Palpatores. Key WordsVSiro, Cyphophthalmi, Opiliones, scent glands, naphthoquinones, methyl ketones. INTRODUCTION The arachnid order Opiliones (also known as harvestmen or daddy longlegs) is estimated to comprise about 5,000 species (Shear, 1982). All possess large scent glands in the prosoma (Juberthie, 1976; Martens, 1978). These glands constitute paired hollow sacs that are surrounded by secretory tissue, each sac opening to the body surface via one single pore at either of the lateral margins of the cephalothorax (Juberthie, 1961; Clawson, 1988). Glandular openings may be developed as oblique slits (Acosta et al., 1993) or, as is the case in the opilionid suborder Cyphophthalmi, they may be located atop conspicuous tubercles, so- called ozophores that dorsolaterally protrude from the carapace (Juberthie, 1961). With regard to biological roles, opilionid scent glands are considered to serve mainly for chemical defense: their secretions, discharged as fine sprays or administered by so-called Bleg-dabbing^ behavior, have been shown to deter ants and other predatory invertebrates (Juberthie, 1976; Martens, 1978; Holmberg, 1986). In addition, pheromonal roles, such as for territorial marking, have been suggested (Juberthie et al., 1991), and recently, the scent gland secretion of a laniatorid opilionid has been reported to possess alarm pher- omonal properties (Machado et al., 2002). Opilionid scent glands not only represent sources of diverse natural products with interesting biological functions, but also may prove useful in chemosystematic studies. Several authors have already alluded to the chemo- taxonomic potential of these secretions (Roach et al., 1980; Ekpa et al., 1985), particularly as the taxonomy of this group is in a state of flux (Shultz and Regier, 2001; Giribet et al., 2002). In fact, in Laniatores, benzoquinones and phenols seem to characterize the scent gland secretions of the superfamily Gonyleptoidea (Eisner et al., 1971, 1977; Roach et al., 1980; Duffield et al., 1981; Gnaspini and Cavalheiro, 1998) whereas from one representative of the laniatorid superfamily Travunioidea, terpenes, bornyl esters, and nitrogen- containing products have been reported (Ekpa et al., 1984). In Palpatores, acyclic compounds have been found in representatives of the genera Leiobunum and Hadrobunus, and naphthoquinones have been found in scent glands of Phalangium (overview in Ekpa et al., 1985). In contrast, nothing is known about the scent gland chemistry of the mitelike representatives of the third classical suborder of Opiliones, the Cyphophthalmi. This small group of Opiliones, so far CHEMICAL PROFILES OF SCENT GLAND SECRETIONS 1355 comprising about 115 species (Giribet and Boyer, 2002), holds a key position in the phylogenetic systematics of Opiliones, possibly representing the most basal opilionid group (e.g., Giribet et al., 2002). In the present paper, to address this gap in opilionid scent gland chemistry, we investigated the scent gland secretions of two species of cyphophthalmid opilionids from two continents, Siro duricorius (mainly distributed in South- eastern Europe) and S. exilis (from the United States). METHODS AND MATERIALS Specimen Collection. S. duricorius (Joseph, 1868) was collected from soil samples at two different localities in Austria. Collection site I was South Carinthia, near Waidischbach (= first collection: 30 adult and 7 juvenile individuals). Collection site II was South Carinthia, Sattnitz (= second and third collection: 27 adults, 9 juveniles and 38 adults, 3 juveniles, respectively). Siro exilis Hoffman (1963) was collected from two soil samples from West Virginia, USA (= fourth and fifth collection: 12 adults, 1 juvenile and 14 adults, 8 juveniles, respectively). Sample Preparation. Scent gland secretions were either directly collected from ozophores or indirectly by whole-body extraction. For direct sampling from ozophores, a specimen was grasped by a leg with forceps, which usually led to the immediate extrusion of a yellowish or brownish droplet of scent gland secretion. The droplet was absorbed on a small piece of filter paper (2  2 mm), then extracted for 5 min in hexane (100 ml). Alternatively, whole specimens were extracted in 100 ml of hexane for about 15 min, expelling their secretions directly into the solvent. Extracts were separated from filter paper pieces or bodies, respectively, and frozen until analysis. Each extract contained the exudate from one individual. Chemical Analysis. Aliquots of crude extracts, in most cases 1 ml, were analyzed by gas chromatographyYmass spectrometry (GC-MS), using a Fisions MD 800 GC-MS (Thermo-Quest, Vienna, Austria). The GC column (ZB-5, 30 m  0.25 mm  0.25 mm film thickness, Phenomenex via HPLC Service, Vienna, Austria) was directly connected to the ion source of the MS. The splitless Grob injector was held at 260-C with helium carrier gas (1.5 ml/min). The electron impact (EI) ion source of the MS was kept at 200-C and the transfer line at 310-C. The following temperature program was used: initial temperature 50-C/1 min, 10-C/min to 200-C, then 15-C/min to 300-C and hold for 5 min. Dimethyldisulfide (DMDS) derivatives, to determine the positions of double bonds, were prepared according to Vincenti et al. (1987). Methyloxime derivatives of the DMDS-derivatized alkanones were prepared by concentrating 20 ml of the solution containing the DMDS adducts under a stream of N2 1356 RASPOTNIG ET AL. and then adding 50 mlofO-methylhydroxylamine hydrochloride (Pierce Bio- technology Inc., Rockford, IL, USA) in pyridine (2%, w/w). The mixture was heated at 75-C for 1 hr. After cooling, 0.5 ml of water was added and the methyloximes were extracted with hexane (2 ml). The solvent was removed under nitrogen and the residue was dissolved in 100 ml ethyl acetate for GC-MS analysis. Reference Compounds. Undecan-2-one, dodecan-2-one, tridecan-2-one, 1,4-naphthoquinone, and 2-methyl-1,4-naphthoquinone, were purchased from Aldrich (Vienna, Austria). 4-Chloro-1,2-naphthoquinone was prepared as de- scribed by Perumal and Bhatt (1980) and Paquet and Brassard (1989): 800 mg lead tetraacetate were added to a solution of 200 mg of 2,4-dichloro-1-naphthol (Aldrich) in 12 ml benzene. The mixture was stirred under nitrogen for 10 hr at room temperature, then poured into 50 ml of water and extracted with ether. The product was purified using silica gel chromatography and CHCl3:hexane (1:2) as eluent. Scanning Electron Microscopy. For scanning electron microscopy (SEM), specimens were fixed in glutaraldehyde, dehydrated, and mounted on small dishes before sputtering with gold. Micrographs were prepared at the Research Institute for Electron Microscopy, Technical University of Graz, Austria. RESULTS Extraction, Separation, and Identification of Scent Gland Components. GC analyses of scent gland secretions of S. duricorius and
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