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Sex Pheromone Component Ratio in the Cabbage Looper Moth

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Sex Pheromone Component Ratio in the Cabbage Looper Moth 7162 Insect Biochem. Molec. Bioi. Vol. 24. No.4. pp. 373-381. 1994 Pergamon Copyright i; 1994 Elsevier Science Ltd rf!') Printed in Great Britain. All rights reserved 0965-1 748/94'S6.OO + 0.00 Sex Pheromone Component Ratio In the Cabbage Looper Moth Altered by a Mutation Affecting the Fatty Acid Chain­ Shortening Reactions in the Pheromone Biosynthetic Pathway RUSSELL A. JURENKA.*t KENNETH F. HAYNES,t RICHARD O. ADLOF,§ MARIE BENGTSSON,,' WENDELL L. ROELOFS* Rl.'ceil'ed /9 Afay /993: reUsed and accepted 24 August 1993 Comparisons in the sex pheromone biosynthetic pathway were made between a normal (wild type) and mutant strains of the cabbage looper moth, Trichoplusia ni, maintained in laboratory colonies. The sex pheromone of normal cabbage loopers consists of the major component, (Z-7-dodecenyl acetate) and the minor compounds (all acetate esters) that are biosynthesized from fatty acid precursors by a combination of All desaturation, chain shortening, reduction and acetylation. The mutant strain is characterized by higher amounts of Z-9-tetradecenyl acetate and lower amounts of Z-7-dodecenyl acetate. Amounts of fatty acid precursor found in pheromone glands were determined and indicated that some precursors were not chain shortened in the mutant strain. Amounts of all 12 carbon fatty acids were lower in the mutant strain compared to the normal strain. Incorporation studies using radiolabeled precursors indicated that the All desaturase, reductase and acetyl-CoA: fatty alcohol acetyltransferase were not affected by the mutation. However, it appeared that chain-short­ ening steps in the biosynthetic pathway were affected in the mutant strain. An in vitro chain-shortening assa~' was dewloped using several different deuterium-labeled fatty acyl-CoAs as substrates to determine how the chain shortening reactions were affected in the mutant strain. The amount of labeled product was determined by gas chromatography-mass spectrometry. The normal strain preferentiall~' chain shortened Z-ll-hexadecenoyl CoA by two rounds of p-oxidation to Z-7-dode­ cenoyl CoA. The mutant strain showed lower levels of chain shortening and only one round of {I-oxidation occurred. Pheromone biosynthesis Chain shortening fJ -oxidation Trichop/usia ni INTRODUCTION are produced in precise ratios. The specific blend of compounds are usually composed of straight chain Chemical communication 10 most moth species hydrocarbons with one or more positions of consists of females emitting compounds that attract unsaturation and a functional group at one end. The conspecific males. These compounds. called sex phero­ functional group is typically an aldehyde, alcohol mones. are composed of a blend of compounds that or acetate ester. Thus the pheromone blend is ·Department of Entomology. Cornell University. New York State composed of compounds that may vary by chain Agricultural Experiment Station. Geneva. NY 14456. U.S.A. length, degree and position of unsaturation and func­ tAuthor for correspondence. tional group. This precise pheromone blend must be ;Department of Entomology. University of Kentucky. Lexington. produced by the female to attract conspecific males for KT 40546. U.S.A. mating. §USDA-ARS. National Center for Agricultural Utilization Research. 1815 North University Street. Peoria. IL 61604. U.S.A. The biosynthetic pathways of several moth phero­ ('Department of Organic Chemistry 3. Lund University. S-221 00 mone blends, including the cabbage looper, Trichoplusia Lund. Sweden. ni, have been determined (Bjostad et aI., 1987). The 373 374 RUSSELL A. JURENKA el al. pathway in Fig. I for the cabbage looper shows MATERIALS AND METHODS that saturated 16- and 18-carbon fatty acids are Insects synthesized de nom from acetate and then a ~ II desaturase forms both ZII-16:CoA* and ZII-18:CoA. The mutant colony of T. ni was isolated and main­ The ~ II monounsaturated CoA derivatives are then tained in one of our labs (Lexington, Ky) as described chain shortened by two or four carbon atoms and previously (Haynes and Hunt, 1990b). Female pupae the chain-shortened compounds are reduced and from the mutant colony were sent to Geneva, N.Y. by acetylated to form acetate esters, which make up overnight mail. Two normal colonies, one in each lab the pheromone blend (Bjostad and Roelofs, 1983). (Lexington, Ky and Geneva, N.Y.), were utilized. Both The pheromone blend of T. ni was initially identified the normal and mutant pupae were segregated daily and c as Z7-12:0Ac (100.0) (Berger. 1966), but along with the newly emerged females maintained at 26 C with this major component several minor components light: dark cycle of 16: 8. All females used in this study have also been identified: 12:0Ac (10.8), Z5-12:0Ac were 1-2 days old and were utilized during the (10.8). ZII-12:0Ac (2.9). Z7-14:0Ac (2.0), photophase. Z9-14:0Ac (0.8). with the relative proportions found in gland extracts indicated in parentheses (Bjostad et al., In duo labeling experiments 1984). The labeled precursors, [U- 14 C]16:acid (0.5.uCi) The ratio of components in the blend emitted by and [18- 14 C] 18: acid (0.2 pCi), were topically applied female moths of some species is very consistent and does to pheromone glands in 0.4 pi of dimethyl sulfoxide, not change even under selection pressure in laboratory allowed to penetrate the cuticle and after a 4 h incu­ colonies (Collins and Carde. 1985: Sreng et al., 1989). bation the glands were removed and extracted and The major pheromone components appear to be methyl esters were made as described later. To follow strongly canalized and it is difficult to shift the blend the incorporation of [1.'4C]acetate, glands were ratio ~;ith laboratory selection. However, minor com­ removed and incubated in 10 pi of saline containing ponent ratios were altered in the redbanded leafroller 0.5 pCi of labeled acetate and after a I h incubation the moth. Argrrotaenia relutinana, with experimental selec­ glands were extracted and methyl esters made as tion pressure (Sreng et al.. 1989). These minor com­ described below. After base methanolysis the acetate ponents consisted of 12-carbon compounds that were esters are present as alcohols and these were separated derived from chain shortening the major 14-carbon fatty from the methyl esters using a small column of silica acvl intermediates. Changes in minor component ratios gel. The methyl esters were eluted with hexane/ w~re also observed in various laboratory colonies of methylene chloride (60/40) and the alcohols with methyl­ T. ni (Havnes and Hunt, 1990a). ene chloride. The alcohols were converted back to Upon ~xamining different populations of T. ni for the acetate esters with acetyl chloride. Both the altered pheromone blends, a laboratory colony was methyl and acetate esters were analyzed separately by found to have some females that had a dramatic differ­ thermal conductivity GC on a 30 m macrobore ence in the pheromone component ratio (Haynes and (i.d. = 0.53) capillary column (SP-2380, Supelco) tem­ Hunt, 1990b). The mutant population was isolated from perature programmed from 90°C (I min) to 200 cC at this laboratorv colonv and genetic studies indicated that 3 Clmin. Compounds eluting from the detector were the altered pheromo~e ble;d was due to an autosomal collected in cold glass micropipets, which were then inheritance of a recessive gene. The mutant has an washed with scintillation fluid, and radioactivity increased amount of Z9-14: OAc and decreased measured. amounts of Z5-12:0Ac, Z7-12:0Ac. II 12:0Ac and Z7-14:0Ac found in air-borne collections of gland volatiles. In the present paper, using a combination of in riro labeling studies and in l'itro enzyme assays, we All r 18:CoA ------. ZlH8:CoA investigated h;w this mutation could alter the phero­ FatlY add !-2C mone blend of T. ni. We demonstrate that chain short­ synthesis ening through limited fJ-oxidation of fatty acyl-CoAs is '-.16:CoA ~ ZlH6:CoA Z9-16:CoA affected by the mutation. !-2C !-2C !-2C 14:CoA Z9-14:CoA' Z7-14:CoA' *The abbreViations used for the fatty acids. acetate esters and methyl esters are as follows. The first number indicates the position of the !-2C !-2C !-2C double bond from the carboxy carbon (all bonds are Z (cis) 12:CoA' Z7-12:CoA' Z5-12:CoA' configuration unless indicated otherwise], the second number indi­ cates the hvdrocarbon chain length, the abbreviation after the All'\ lJ-12:CoA' colon indic~tes the class of compound. Acid = free carboxy acid, OAc = acetate ester. CoA = coenzyme A ester. acyl = fatty acid FIGURE I. Pheromone biosynthetic pathway of the cabbage looper. linked to complex lipid. For example Z7-12: OAc = (Z)-7-dode­ The acyl-CoA derivatives that are reduced and acetylated to form the cenyl acetate. GC = gas chromatography. MS = mass spec­ pheromone blend are indicated by *. till = till desaturase. trometry. -2C =chain-shortening enzymes. FATTY ACID CHAIN-SHORTENING 375 Gland extraction (80GC for I min and then 10GC;min to 200 G C) in a Glands were extracted with chloroform: methanol Hewlett-Packard 5890 was used to separate methyl (2: I) for 16 h. Methyl esters were generated by base esters. The compounds were detected with a HP 5970 methanolysis and the acetate esters regenerated with series mass selective detector set in the single ion moni­ acetyl chloride (Bjostad and Roelofs, 1981). Internal toring mode. For the saturated series the ions that were standards of triheptadecanoylglycerol and 13: OAc were monitored were as follows: CI8-298, CI6-270. CI4-242. added at the beginning of the extraction procedure to CI2-214, CIQ-186. The ~HJ labeled compounds were quantify the fatty acyl and acetate esters. respectively. monitored at the above ions + 3.
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