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Plagiodera Versicolora)* (Arthropods/Iridoids/Chrysomelidial/Plagiolactone) JERROLD Meinwaldt, TAPPEY H

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Plagiodera Versicolora)* (Arthropods/Iridoids/Chrysomelidial/Plagiolactone) JERROLD Meinwaldt, TAPPEY H Proc. Natl. Acad. Sci. USA Vol. 74, No. 6, pp. 2189-2193, June 1977 Chemistry New methylcyclopentanoid terpenes from the larval defensive secretion of a chrysomelid beetle (Plagiodera versicolora)* (arthropods/iridoids/chrysomelidial/plagiolactone) JERROLD MEINWALDt, TAPPEY H. JONESt, THOMAS EISNERf, AND KAREN HICKSt t Department of Chemistry and * Section of Neurobiology and Behavior, Cornell University, Ithaca, New York 14853 Contributed by Jerrold Meinwald and Thomas Eisner, April 11, 1977 ABSTRACT The defensive secretion of larvae of the CH3 o CH3 -Glucose chrysomelid beetle Plagiodera versicolora contains two un- stable, volatile methylcyclopentanoid terpenes: a dialdehyde (chrysomelidial) isomeric with dolichodial and anisomorphal, H and a closely related enol lactone (plagiolactone). Chrysomel- idial and plagiolactone are shown to have structures III and IV on the basis of a detailed analysis of their spectra, coupled with H3 CO2CH3 chemical transformations to products of known structure. I II CH3 H3 CHO CH3 H3 CHO / 0 CHO 0 CHO H3 H3 III IV -H3 H3 la IV The structure of nepetalactone (I) was established over 20 years species of Chrysomelidae have comparable discharge mecha- ago (1, 2). At that time this compound, which had been isolated nisms, which have been described (9). Chemical work on the from the essential oil of the mint Nepeta cataria (3), was re- secretion of some of these larvae has led to the isolation of garded chiefly as a chemical curiosity; it had gained some salicylaldehyde from Phyllodecta vztellinae (10), Melasoma low-keyed notoriety because of the bizarre behavioral responses populi (11), and Chrysomela scripta (12), and of fl-phenyl- it was capable of eliciting in a variety of felids of both sexes (4). ethyl isobutyrate and fl-phenylethyl 2-methybutyrate from It subsequently developed, however, that nepetalactone was Chrysomela interrupta (13). It was clear from the odor of the the first recognized representative of the methylcyclopentanoid secretion of Plagiodera that this animal produces a secretion terpenes, a large and diverse group of natural products based of entirely different composition. on the 1,2-dimethyl-3-isopropylcyclopentane skeleton, whose chemistry was summarized in an extensive monograph pub- EXPERIMENTAL SECTION lished some 15 years later (5). These terpenoids are widely distributed in nature, and members of the group have been Gas chromatographic analyses were carried out using 2.5 m X found to serve many diverse functions, including insect repel- 2 mm columns packed with 5% OV-1 on Gas-Chrom Q (column lent in plants (6), "anti-aphrodisiac" (ref. 5, p. 136) antibiotic A), 3% OV-225 on Gas-Chrom Q (column B), or 5% FFAP on (ref. 5, p. 136), and insect defense agent (ref. 5, pp. 203-238). Gas-Chrom Q (column C) (packing materials from Applied The recognition of the central role played in the biosynthesis Sciences Laboratories, Inc). Mass spectra were obtained at 70 of many alkaloids by loganin (II), a methylcyclopentanoid eV using a Finnigan model 3300 gas chromatograph/mass terpene glycoside, has provided an important insight into the metabolic link between the alkaloids and the terpenes (5, 7, 8). We wish to report the isolation and characterization of two new methylcyclopentanoid terpene derivatives, chrysomelidial (III) and plagiolactone (IV), from the defensive secretion of larvae of a chrysomelid beetle, Plagiodera versicolora. Plagiodera larvae occur commonly during the summer months on leaves of willow trees (Salix spp.) in the environs of Ithaca, NY. The larvae have nine pairs of glands, arranged segmentally along the sides of the body. They discharge se- cretion readily in response to direct disturbance (Fig. 1). Related Abbreviations: GC, gas chromatography; MS, mass spectrometry; m/e, mass-to-charge ratio; IR, infrared; NMR, nuclear magnetic resonance; for NMR spectroscopy, s is a singlet peak, d is a doublet, t is a triplet, q is a quartet, m is a multiplet, and br is broad. * This is report no. 56 of the series "Defense Mechanisms of Arthro- FIG. 1. Larva ofPlagiodera versicolora responding to pinching pods." Report no. 55 is Brattsten, L. B., Wilkinson, C. F. & Eisner, ofone ofits legs with forceps by emitting secretion from its segmental T. (1977) Science, in press. defensive glands. (Reference bar = 1 mm.) 2189 Downloaded by guest on September 28, 2021 2190 Chemistry: Meinwald et al. Proc. Natl. Acad. Sci. USA 74 (1977) spectrometer (GC/MS) coupled with a System Industries model J = 2.5 Hz, CHCHO), 2.2-0.9(15 protons, complex multiplet); 150 computer. High resolution mass spectra were obtained MS, mle 111(4),107(2),97(2),95(2),93(2),91(2),83(20),82(26), using an AEI MS-902 instrument coupled with a VG Data 81(13), 80(5), 79(6), 69(87), 67(39), 58(100), 55(95), 43(20), System 2020 computer. 41(65). Except for the parent peak and the peak for parent ion Hydrogenation of Chrysomelid Secretion. The secretion minus 15 mass units, which were not observed under the con- from 282 larvae was taken up in a few milliliters of ether. This ditions used to obtain this mass spectrum, these data compare solution was added to 1 ml of ether containing 25 mg of 10% well with the data obtained for the major hydrogenolysis Pd/C which had been saturated with hydrogen. The mixture product from the chrysomelid secretion. was stirred for 1 hr under a slight positive pressure of hydrogen. Chrysomelidial and Plagiolactone. Gas chromatographic After filtration and concentration of the solution, GC/MS analysis (column B) of fresh chrysomelid secretion showed two analysis (column A) showed the presence of 7 to 10 peaks de- major components, the first, chrysomelidial, always more than pending on theGC conditions. One of the minor components twice as abundant as the second, plagiolactone. Preparative GC (about 10%) had a mass spectrum identical to that reported for (column B) of the concentrated ether washings of filter paper 1-ethyl-3-methylcyclopentane (V) (14). The major component squares used to absorb the secretion of 2000 larvae gave ap- of the mixture had MS, m/e peaks (relative intensities in pa- proximately 0.2 mg of chrysomelidial as a pale yellow liquid. rentheses) 140(1), 125(4), 111(11), 97(6), 95(3), 93(2), 91(2), IR (CC14) 1720, 1660, 1620 (shoulder) cm-1; NMR (100 MHz) 83(27), 82(45), 81(21), 80(6), 79(7), 69(89), 67(38), 58(100), a 10.19(1, s, C=C-CHO), 9.98, 9.85 (1, s, s, CH-CHO), 3.63 55(82), 43(16), 41(57). This mass spectrum corresponds well [1, br m, C=C(CHO)-CHI, 3.08(1, m, CHCHO), 2.60(2, br with that obtained for synthetic 2-(3-methylcyclopentanyl)- t, CH2C=C), 2.18 (3, s, CH3-CC), 1.02 and 0.89 (3, pair propionaldehyde (VI), prepared as described below. of d, J = 7.2 Hz, CH3CHCHO); there was also an absorption 2e(3-Methylcyclopentylidene)propionaldehyde. This al- at a 1.3 due to water; MS (column C), m/e 166(4), 148(21), dehyde was prepared in low yield using the general method 136(8), 134(8), 120(10), 109(52), 108(39), 107(32), 105(16), described by Meyers et al. (15). A solution containing 5.0 g (32.2 96(10), 95(20), 93(16), 91(19), 82(10), 81(100), 80(25), 79(71), mmol) of 2-ethyl-4,4,6-trimethyldihydro-1,3-oxazine in 30 ml 78(15), 77(26), 67(20), 65(10), 55(22), 53(27), 51(10); calculated of tetrahydrofuran was cooled to -780 and treated with 17.5 mass for CloH1402 166.0994, found m/e 166.0997; calculated ml of 2 M 1-butyllithium. After stirring of the mixture for 1 hr, mass for C7H9O 109.0655, found m/e 109.0632; calculated a solution containing 3.44 g (35.2 mmol) of 3-methyl-1-cyclo- mass for C7H80 108.0575, found m/e 108.0551. pentanone in 10 ml of tetrahydrofuran was added dropwise Approximately 0.1 mg of plagiolactone was also isolated by over 1k hr. The mixture was allowed to warm to room temper- preparative GC of the same ether washings, as a waxy solid ature over 1 hr, poured into ice, acidified with 10% HCI, and which melted as room temperature. This compound had the extracted with pentane. The aqueous layer was then made basic following spectral data. UV XEt1' 244-252 nm, E _ 5,000 M- with 10% NaOH and ice, and extracted with three 75 ml por- cm- 1; IR (CC14) 1764 cm-1; NMR (100 MHz) (assignable sig- tions of ether. The-ether extract was dried over anhydrous nals) 66.53(1, br s, C-CH-0C=0), 5.73(1, br s, HCC), K2CO3 and concentrated under reduced pressure, and the 2.47 (1, d of q, J = 6.6 Hz and 14 Hz), 1.82 (3, br s, CH3- residue was taken up in a mixture of 30 ml of ethanol and 30 C=C), and 1.28(3, d, J = 6.6 Hz, CH3-CH). Decoupling of ml of tetrahydofuran. The pH was adjusted to 7; the mixture the doublet at 51.29 collapsed the doublet of quartets at 52.47 was cooled to -350, and treated with a solution containing 1.22 to a doublet, J = 14.0 Hz; MS, m/e 164(60), 136(21), 121(28), g of NaBH4 in 5 ml of H20 containing 1 drop of 40% NaOH. 109(11), 108(48), 107(49), 106(15), 93(39), 91(45),-80(85), During this addition, the pH was maintained at 6-8 by the 79(100), 78(16), 77(50), 65(16), 53(11), 51(18); calculated mass addition of dilute HCL.
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