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Identification of a Female-Specific, Antennally Active Volatile Compound of the Currant Stem Girdler*

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Identification of a Female-Specific, Antennally Active Volatile Compound of the Currant Stem Girdler* Joumal ofChemical Ecology, Vol. 27, No.9, September 2001 (@ 2001) IDENTIFICATION OF A FEMALE-SPECIFIC, ANTENNALLY ACTIVE VOLATILE COMPOUND OF THE CURRANT STEM GIRDLER* ALLARD A. COSSE,I.t ROBERT J. BARTELT,! DAVID G. JAMES,2 and RICHARD J. PETROSKI' I USDA Agricultural Research Service National Centerfor Agricultural Utilization Research Bioactive Agents Research Unit 1815 N. University Street, Peoria, Illinois 61604 21rrigated Agriculture Research and Extension Center Washington State University 24106 North BUlllI Road Prosser, Washington 99350 (Received November 30,2000; accepted May 12,2001) Abstract-We identified (Z)-9-octadecen-4-olide as a female-specific, anten­ nally active compound from the currant stem girdler Janus integer Norton. Fe­ male specificity was demonstrated by gas chromatographic comparison of liq­ uid chromatography fractions of male and female volatile emissions and whole body extracts. The y-lactone was identified by coupled gas chromatographic­ electroantennographic detection (GC-EAD), coupled gas chromatographic-mass spectrometric (GC-MS) analysis, microchemical reactions, and GC and MS comparison with authentic standards. GC-EAD analysis offemale volatile emis­ sions and cuticular extracts showed a single peak of activity on male antennae, which was not present in male-derived materials. Female antennae did not re­ spond to any of the tested materials. The hydrogenation product of the natural EAD-active material was a known saturated y-lactone. The mass spectrum of the dimethyl disulfide derivative of the natural y-lactone was consistent with a double bond present in the 9 position. Comparison ofthe natural y-Iactone and a synthesized racemic mixture of (Z)-9-octadecen-4-0Iide on a chiral GC column showed the presence of a single enantiomer in the natural material. *Mention of trade names or commercial products in this article is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the U.S. Department of Agriculture. tTo whom correspondence should be addressed. e-mail: [email protected] 1841 0098·0331/0 1I0900·184IS19.50/0 '£' 2001 Plenum Publishing Corporation 1842 COSSE, BARTELT, JAMES, AND PETROSKI Key Words-Jan liS illteger, sawfly, Hymenoptera, Cephidae, sex pheromone, (Zl-9-octadecen-4-o1ide, coupled gas chromatographic-electroantennographic detection (GC-EAD). INTRODUCTION The currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), is an occasional pest of red currant (Ribes spp,) in North America (Crassweller et aI., 1997), In spring, egg laying female 1. integer can make numerous punctures in canes, resulting in drooping and wilting of new shoots, Further damage occurs as emerging larvae tunnel within the canes, This insect also attacks poplar and willow trees, and damage to currants usually is more severe near stands of these trees (Crassweller et aI., 1997), Preliminary field observations indicated that caged virgin females attracted male 1. integer (D, G, James, unpublished data), thus 1. integer could utilize a female-produced sex pheromone for mate location, Currently, the only studied cephid pheromone is that of the wheat stem sawfly, Cephus cinctus Norton (Cosse et aI., unpublished data), The pheromone may be beneficial to current pest control practices, especially since insecticides are ineffective against larvae inside the currant stems, This paper describes the isolation, structure determination, and electroan­ tennographic activity of a female-specific volatile compound and compares this with other sawfly pheromones, MATERIALS AND METHODS Insects, Overwintering currant stem girdler larvae present in dormant red cur­ rant stems were collected near Prosser, Washington, during January 2000, Larva­ containing stems were placed individually into glass vials, capped with a moist piece ofcloth-covered cotton, and sent to NCAUR. Upon arrival in Peoria, Illinois, the vials were kept at 25°C under a 16:8 (LD) hour photoperiod regime, Adults emerged about three weeks later. Adults used in this study were 1- to 4-days old, Volatile Collections and Cuticular Extracts, One- to three-day volatile collec­ tions were made from individuals or groups of 4 male or female insects. Volatiles were trapped on Super Qporous polymer (80-100 mesh, Alltech, Deerfield, IL) or on solid-phase microextraction (SPME) fibers (l00 !Lm poly(dimethyl)siloxane, Supelco, Bellefonte, PA). Volatile collections were made by methods and equip­ ment generally described by Cosse and Bartelt (2000), Cuticular extracts were obtained by a single rub of the abdomen of individual male or female insects with a SPME fiber, In addition, individuals or groups of 8 male or female insects were killed by freezing when 1-4 days old, and soaked overnight in 1 ml hexane, FEMALE-SPECIFIC, COMPOUND OF THE CURRANT STEM GIRDLER 1843 Hexane extracts were stored at -20°C Extracts were concentrated under a gentle stream of nitrogen and fractionated on open columns of silica gel (0.5 x 3 cm). Two-milliliter fractions were collected for each of the following elution solvents: hexane; 5%, 10%, and 25% ether in hexane (by volume); and ether. Fractions were concentrated to a volume similar to the non-fractionated samples prior to any further analysis. Electrophysiology. Coupled gas chromatographic-electroantennographic (GC-EAD) analyses were made by methods and equipment generally described by Cosse and Bartelt (2000). GC-EAD connections were made by inserting a glass­ pipette Ag-AgCl-grounding electrode into the back of an excised sawfly head. A second glass-pipette Ag-AgCl-recording probe was placed in contact with the dis­ tal end of one antenna. Both pipettes were filled with Beadle-Ephrussi (Ephrussi and Beadle, 1936) saline. Instrumentation. Volatile collections, extracts, and liquid chromatography (LC) fractions were analyzed by gas chromatography with flame-ionization de­ tection (GC-FID) and coupled GC-mass spectrometry (GC-MS, electron impact and chemical ionization). Samples were injected in splitless mode using Hewlett Packard 6890 instruments fitted with 30 meter EC-l capillary columns (0.25 mm LD., 0.25 {Lm film thickness, Alltech, Deerfield, IL). Temperature programs were from 50°C to 275°C at lQoC per min (GC-MS) or at lSOCpermin (GC-EAD). Injec­ tor temperatures were maintained at 250°C, and GC-EAD effluent interface from post-column splitter was kept at 275°C Injectors were fitted with SPME injector liners (Supelco, Bellefonte, PA) for SPME analysis. Mass spectrometry was per­ formed with a Hewlett Packard 5973 instrument (electron impact, 70 eV). Chemical ionization spectra (isobutane) were obtained on a Thermo Quest Trace GC 2000 quadrupole mass spectrometer. The Wiley mass spectral library, with 275,821 spectra, was available on the MS data system (Wiley, 1995). Chiral resolution was achieved on a capillary column having a diacetyl-derivatized ,B-cyclodextrin phase, ,B-DEX 225 (30 m length, 0.25 mm ID, 0.25 {Lm film thickness; Supelco, Bellefonte, PA) operated at 200°C Microchemical Reactions. Hydrogenation of GC-EAD-active LC fractions was used to confirm the number of carbon-carbon double bonds. Samples (100 {Ll) were stripped to dryness under a stream of nitrogen and resuspended in 100 {Ll ethanol to which was added "-'0.5 mg of 10% Pd on charcoal. Reduction was accomplished by bubbling a gentle stearn of hydrogen through the sample for 5 min at room temperature. The reduced sample was filtered and analyzed by GC-MS and GC-EAD. Dimethyl disulfide (DMDS) derivatives were prepared for determination of double bond locations of EAD-active material (Carlson et aI., 1989). Samples (lOa {Ll) were stripped to dryness under a stream of nitrogen, and DMDS and 5% iodine in ether were added (equal volumes, about 25 {Ll each). The samples were heated at 45°C for 1-2 hr, then diluted with hexane and worked up with 1844 COSSE, BARTELT, JAMES, AND PETROSKI aqueous sodium thiosulfate to destroy the iodine. The organic layer was dried over sodium sulfate, evaporated under nitrogen, resuspended in about 10 III hexane, and analyzed by GC-MS. Oven temperature was programmed up to 300°C, and MS scanning range was 40-600 amu. The antenally active 10% etherlhexane LC fractions contained two major free fatty acids, linoleic- and oleic acid, which were methylated to the corresponding methyl esters with diazomethane. Approximately 5 mg of N-methyl-N-nitroso­ p-toluenesulfonamide (Diazald, Aldrich, Milwaukee, WI) were added to a 1: 1 mixture of ether and a mixture of 5% aqueous KOH and methanol 0:1). Ten micro liters of the yellow ether layer were added to 100 ILl of the EAD-active LC fraction. After 5 min, the mixture was evaporated and the residue dissolved in hexane for GC-MS and GC-EAD analysis. HO(CH2)60H PPTS 1hexane, acetonitrile HO(CH2)60THP ~ PDC, CH 2CI 2 OHC(CH2)sOTHP nonyl(triphenyl)phosphonium bromide, 1THF,BuLi CH3(CH2hCH=CH(CH2hOTHP (mostly Z) ~ Dowex SOW x 8, MeOH CH3(CH2hCH=CH(CH2)SOH ~ PDC, CH 2C1 2 CH3(CH2hCH=CH(CH2)4CHO 1. Br(CH2hC02Et, SmI2, HMPA, THF 12. HCI CH3(CH2hC=C(CH2)4~O + (E)-isomer II HH (Z)-9-octadecen-4-olide FIG. 1. Synthesis of (Z)-9-octadecen-4-o1ide (see text for abbreviations). FEMALE-SPECIFIC, COMPOUND OF THE CURRANT STEM GIRDLER 1845 Synthesis of (Z)-9-octadecen-4-0Iide. A preliminary synthesis to confirm structure was conducted by one of us (RJP), based on well-known reactions (Figure I). One hydroxy group of 1,6-hexanediol (Aldrich, Milwaukee, WI) was protected as a tetrahydropyranyl (THP) ether by using pyridinium p-toluenesulfo­ nate (PPTS) as catalyst (Miyashita et aI., 1977). Monoprotection of the diol was accomplished by modification of the published procedure (Miyashita et aI., 1977). In a biphasic mixture ofacetonitrile and hexane, the reactants were primarily in the more polar (acetonitrile) phase, but the mono ether migrated to the hexane phase, reducing the chance offurther derivatization to the diether. The free hydroxyl was oxidized with pyridinium dichromate (PDq in CH2Ch to give the aldehyde (Corey and Schmidt 1979).
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