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IDENTIFICATION of CHIRAL SEX PHEROMONE SECRETED by GIANT GEOMETRID MOTH, Biston Robustum Butler

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IDENTIFICATION of CHIRAL SEX PHEROMONE SECRETED by GIANT GEOMETRID MOTH, Biston Robustum Butler Journal of Chemical Ecology, Vol. 26, No. 11, 2000 IDENTIFICATION OF CHIRAL SEX PHEROMONE SECRETED BY GIANT GEOMETRID MOTH, Biston robustum Butler MASANOBU YAMAMOTO,1 MASAAKI KISO,2,3 HIROYUKI YAMAZAWA,1 JUN TAKEUCHI,2 and TETSU ANDO1,* 1Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology Koganei, Tokyo 184-8588, Japan 2Agricultural Technology Center Hachijo-jima, Tokyo 100-1401, Japan (Received November 15, 1999; accepted July 8, 2000) Abstract—Biston robustum Butler, a polyphagous defoliator, multiplied on Hachijo-jima Island in 1997–1998. Based on GC-MS data of authentic standards, an analysis of a pheromone gland extract of the females indicated that it included (Z,Z)-6,9-nonadecadiene (I), (Z,Z,Z)-3,6,9-nonadecatriene (II), cis-(Z)-6,7-epoxy-9-nonadecene (III), and cis-(Z,Z)-6,7-epoxy-3,9-nona- decadiene (IV) in a ratio of 13 : 2 : 70 : 15. The structure of III was confirmed by a GC-MS analysis of another extract treated with dimethyl disulfide (DMDS). This epoxymonoene was successfully converted into the corresponding DMDS adduct that showed diagnostic ions fragmented at an epoxy ring and at thiomethoxy groups reflecting the position of an original double bond. Furthermore, the 6S,7R configuration was assigned for the epoxy ring of III by chiral HPLC analysis. Field examination of synthetic lures revealed that the two epoxy compounds (III and IV) with the 6S,7R configuration were essential components and that the two unsaturated hydrocarbons (I and II) showed a synergistic effect on male attraction. Key Words—Female sex pheromones, Lepidoptera, Geometridae, Ennomi- nae, epoxynonadecene, epoxynonadecadiene, chiral epoxide, chiral HPLC, dimethyl disulfide adduct. *To whom correspondence should be addressed. 3 Present address: Tokyo Metropolitan Agricultural Experimental Station, Tachikawa, Tokyo 190- 0013, Japan; e-mail: [email protected] 2579 0098-0331/ 00/ 1100-2579$18.00/ 0 2000 Plenum Publishing Corporation 2580 YAMAMOTO ET AL. INTRODUCTION The larva of the giant geometrid, Biston robustum Butler (Geometridae: Ennomi- nae), is a common polyphagous defoliator, and the adult appears only once in the early spring. In 1997 and 1998, this univoltine species multiplied to an extraor- dinary population level on the Japanese island of Hachijo-jima, which is a busy tourist resort 280 km south of Tokyo. The southern part of the island is covered with broadleaf trees, the Japanese chinquapin, cherry, and others, which were devastated by the unusually high population of larvae. Authorities are eager to develop a technique for monitoring and further controlling the population. There- fore, we have begun to identify the sex pheromone of B. robustum. Female sex pheromones from about 40 species in the family of Geometri- dae have been chemically characterized. These pheromones are predominantly composed of (Z,Z)-6,9-dienes and (Z,Z,Z)-3,6,9-trienes with a C17–C23 straight chain and their monoepoxy derivatives, which lack a terminal functional group (Arn et al., 1992, 1997). The pheromonal epoxymonoenes and epoxydienes are expected to be synthesized from the dienes and trienes in the pheromone gland by oxidation catalyzed with a monooxygenase (Miyamoto et al., 1999). Variation in the epoxy ring position and the carbon chain length causes com- plexity of the geometrid pheromones, playing an important role in reproductive isolation. In this paper, we report the identification of C19 components in the pheromone extract of B. robustum. The determination of the epoxy ring posi- tion was achieved by a GC-MS measurement, which proposed some diagnostic fragment ions that had been reported in earlier studies (Ando et al., 1993, 1995). Furthermore, the structure of epoxymonoene was confirmed by a GC-MS anal- ysis of a pheromone extract treated with dimethyl disulfide (DMDS), and the stereochemistry of the epoxy ring was determined by chiral HPLC. The results of the preliminary field test with a synthetic chiral pheromone are also reported. METHODS AND MATERIALS GC-MS Analysis. An electron impact GC-MS was achieved by using a Jeol JMS-AM II 20 mass spectrometer equipped with a DB-23 capillary column (0.25 mm ID × 30 m; J&W Scientific) to analyze a pheromone extract, or a DB- 1 capillary column (0.25 mm ID × 30 m; J&W Scientific) to analyze DMDS adducts derived from epoxymonoenes. The oven temperature program for the former column was 808C for 2 min, 108C/ min to 1608C, and finally 48C/ min to 2208C. The program of the latter column was 1208C for 2 min and 68C/ min to 2708C. The ionization voltage was 70 eV, and the ion-source temperature was 2408C. Chromatography. The HPLC involved a Jasco PU-980 liquid chromato- CHIRAL SEX PHEROMONE OF GEOMETRID FEMALES 2581 graph equipped with an integrator (System Instrument Chromatocorder 21J), an RI detector (Labo System RI-98SCOPE), and a Chiralpak AD column (0.46 cm ID × 25 cm; Daicel Chemical Industry Co.) or an ODS column (0.46 cm ID × 25 cm; Senshukagaku). As a mobile phase, 0.1% 2-propanol in n-hexane was used for the former normal-phase chiral column at a flow rate of 0.45 ml/ min, and 5% water in methanol for the latter reversed-phase achiral column at a flow rate of 1.0 ml/ min. GC analysis was achieved by using an HP GC System 6890 series with a flame ionization detector and a DB-23 capillary column (0.25 mm ID × 30 m, J&W Scientific). The temperature program was 508C for 2 min, 108C/ min to 1608C, and finally 48C/ min to 2208C. Insect and Pheromone Extraction. Adult females of B. robustum drawn towards a street lamp were collected at Hachijo-jima Island in the early spring of 1998 and 1999. Two or three days after the collection, pheromone glands were removed from the moths during scotophase and soaked in n-hexane for 30 min to extract the sex pheromone. The GC-MS analysis of the extract was carried out without any purification, but the extract was partially purified by HPLC with an ODS column to examine the stereochemistry of the natural pheromone by chiral HPLC. Chemicals. Synthesis, purification, and chemical characterization of all unsaturated hydrocarbons and their monoepoxy derivatives used in this report have been reported in detail previously (Ando et al., 1993, 1995). Opti- cally active epoxy compounds were prepared by resolution of a racemic mix- ture that used chiral HPLC (Qin et al., 1997; Yamamoto et al., 1999). In this text, chemicals are abbreviated as follows: cis-(Z)-6,7-epoxy-9-nonadecene c epo6,Z9–19 : H, cis-(Z,Z)-6,7-epoxy-3,9-nonadecadiene c Z3,epo6,Z9–19 : H, and so on. Derivatization with DMDS. Each synthetic epoxymonoene (500 ng) was dissolved in a mixture of DMDS (10 ml) and diethyl ether (30 ml) including iodine (1.8 mg). The reaction mixture was kept at 408C for 4 hr and diluted with diethyl ether after cooling. Iodine was removed by shaking with a 10% aqueous Na2S2O3 solution, and crude products were analyzed by GC-MS. The pheromone extract [10 female extract (FE)] was also treated with DMDS in the same manner. Field Tests. Field attraction of the synthetic lures was examined in 1999 by using white rubber septa (8 mm OD, Aldrich), which were totally immersed with 1 mg of epoxy compounds as follows: (a) racemic epo6,Z9–19 : H mixed with racemic Z3,epo6,Z9–19 : H in a ratio of 10 : 0, 9 : 1, 5 : 5, 1 : 9,or0 : 10, (b) opti- cally active epo6,Z9–19 : H (6S,7R and 6R,7S isomers with 100 or 80% ee) mixed with Z3,epo6,Z9–19 : H possessing the same stereochemistry in a ratio of 9 : 1, and (c) optically active epo6,Z9–19 : H mixed with Z3,epo6,Z9–19 : H possess- ing the opposite stereochemistry in a ratio of 9 : 1.In2000, effect of unsaturated hydrocarbons on the attractive activity of these epoxy compounds was exam- 2582 YAMAMOTO ET AL. ined. The tested lures were baited with 0.5 mg of Z6,Z9–19 : H, Z3,Z6,Z9–19 : H, epo6,Z9–19 : H (6S,7R isomer), and Z3,epo6,Z9–19 : H (6S,7R isomer) in ratios of 9 : 1 : 81 : 9, 10 : 0 : 81 : 9,or0 : 0 : 90 : 10. Each lure was placed in a trap (30 × 27 cm bottom plate with roof; Takeda Chemical Ind.) that was set at a height of 1.5 m along a forest road in Hachijo-jima Island from February to March. RESULTS GC-MS Analysis of Pheromone Gland Extract. A GC-MS analysis of the pheromone extract (1 FE) produced a total ion chromatogram (TIC) shown in Figure 1A. Mass chromatograms with M+ ions of tri- and diunsaturated hydro- carbons with a C17–C23 chain and their monoepoxides, which were character- ized as pheromone components of geometrid moths or their biosynthetic pre- cursors (Arn et al., 1992, 1997; Ando et al., 1997), indicated that the extract included the following four C19 compounds (I–IV) in a ratio of 13 : 2 : 70 : 15; i.e. diene (compound I) with a peak of m/ z 264 at 10.10 min (Figure 1C), triene FIG. 1. GC-MS analysis of a pheromone extract of Biston robustum (1 FE); total ion chro- matogram (TIC) (A) and mass chromatograms (B–E). The mass chromatograms moni- + tored M of C19 triene (B, m/ z 262), diene (C, m/ z 264), epoxydiene (D, m/ z 278), and epoxymonoene (E, m/ z 280). Compounds: I c Z6,Z9–19 : H, II c Z3,Z6,Z9–19 : H, III c epo6,Z9–19 : H, and IV c Z3,epo6,Z9–19 : H.
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