Cabbage looper moths

Fig.i General biosynthetic pathways for the production of alcohol, aldehyde, and acetate ester pheromone components in female moths. Top production of saturated fatty acids. Middle production of monounsaturated fatty acids and limited chain shortening produces intermediate compounds that can be reduced to an alcohol. Aldehyde and acetate ester pheromones are produced by an oxidase and acetyl-transferase, respectively. Bottom biosynthetic pathway for the production of the acetate ester pheromone components in the cabbage looper moth, Trichoplusia ni. The CoA derivatives are reduced and acetylated to form the acetate esters. Additional pheromone components include 12 OAc and ll-12 OAc... 

FIGURE 2 Pheromone structures of the American cockroach (periplanone B), the brownbanded cockroach (supellapyrone), bark beetles (ipsdienol enantiomers), and the cabbage looper moth (six acetates). 

In contrast to pheromones that involve single complex compounds, many moth species have been found to utilize a specific blend of relatively simple fatty acid-derived compounds. It appears that the evolution of a unique enzyme, A1 desaturase, used in combination with 2-carbon chain-shortening reactions (Figure 3) has allowed moth species to produce a variety of unsaturated acetates, aldehydes, and alcohols that can be combined in almost unlimited blends to impart species specificity. For example, biosynthetic precursors for the six-component pheromone blend of acetates for the cabbage looper moth (12) (Figure 2) can be determined easily from the cascade of acyl intermediates produced by the A11-desaturase and chain-shortening reactions (Figure 3). 

This olefination protocol was applied to a short and efficient synthesis of (Z)-dodec-7-enyl acetate, the cabbage looper moth pheromone131. 

Landolt, P. J. (1993). Effects of host plant leaf damage on cabbage-looper moth attraction and oviposition. Entomologia Experimentalis etApplicata 67 79-85. 

Haynes, K.F., Zhao, J. Z. and Latif, A. (1991). Identification of floral compounds from Abelia grandiflora that stimulate upwind flight in cabbage looper moths. Journal of Chemical Ecology 17 637-646. 

Heath, R. R., Landolt, P. J., Dueben, B. and Senczewski, B. (1992). Identification of floral compounds of night-blooming jessamine attractive to cabbage looper moths. Environmental Entomology 21 854-859. 

Hydroxydanaidal has been extracted from coremata (Krasnoff and Roelofs, 1989). Like the cabbage looper moth, the salt marsh caterpillar moth has a dual signaling system, but in the case of E. acrea both males and females are attracted, leading to aggregations. 

Genetics of pheromone communication in the cabbage looper moth, Trichoplusia ni. In Insect Pheromone Research New Directions, eds. R. T. Carde and... 

Haynes, K. F. and Hunt, R.E. (1990). A mutation in pheromonal communication system of cabbage looper moth, Trichoplusia ni. Journal of Chemical Ecology 16 1249-1257. 

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. Insect Biochemistry and Molecular Biology 24 373-381. 

Todd, J. L., Anton, S., Hansson, B. S. and Baker, T. C. (1995). Functional organization of the macroglomerular complex related to behaviourally expressed olfactory redundancy in male cabbage looper moths. Physiological Entomology 20 349-361. 

These acids are very important in human nutrition.1193 1 (See also Box 21-B.) In the absence of adequate essential fatty acids oleate is desaturated and elongated in a similar sequence to the unusual 20 3 (A5 8 11 co9) acid. Vertebrate tissues also carry out desaturation at the A4 and A3 positions.111 Lepidoptera, which synthesize a great diversity of pheromones, are rich in unusual desaturases such as the gland-specific acyl-CoA A11 desaturase of cabbage looper moths.120... 

Percy J. (1979) Development and ultrastructure of sex pheromone gland cells of the cabbage looper moth, Trichoplusia ni (Lepidoptera Noctuidae). Can. J. Zool. 57, 220-236. 

Knipple D. C Rosenfield C Miller S. J., Liu W Tang J., Ma P. W. K. and Roelofs W. L. (1998). Cloning and functional expression of a cDNA encoding a pheromone gland-specific acyl-CoA All-desaturase of the cabbage looper moth, Trichoplusia ni. Proc. Natl. Acad. Sci. USA 95, 15287-15292. 

Wolf W. A. and Roelofs W. L. (1986) Properties of the All-desaturase enzyme used in cabbage looper moth sex pheromone biosynthesis. Arch. Insect Biochem. Physiol. 3, 45-52. 

Jurenka R. A., Haynes K. F., Adlof R. O., Bengtsson M. and Roelofs W. L. (1994) Sex pheromone component ratio in the cabbage looper moth altered by a mutation affecting the fatty acid chain-shortening reactions in the pheromone bisoynthetic pathway. Insect Biochem. Molec. Biol. 24, 373-381. 

Tang J., Wolf W. A., Roelofs W. L. and Knipple D. C. (1991) The development of functionally competent cabbage looper moth sex pheromone glands. Insect Biochem. 21, 573-581. 

Ferkovich S. M., Oliver J. E. and Dillard C. (1982) Pheromone hydrolysis by cuticular and interior esterases of the antennae, legs, and wings of the cabbage looper moth, Trichoplusia ni (Hubner). J. Chem. Ecol. 8, 859-866. 

Taylor T. R., Ferkovich S. M. and Van Essen F. (1981) Increased pheromone catabolism by antennal esterases after adult eclosion of the cabbage looper moth. Experentia 37, 729-731. 

Todd J. L. and Baker T. C. (1996) Antennal lobe partitioning of behaviorally active odors in female cabbage looper moths. Naturwissenschaften. 83, 324—326. 

Harry Shorey Discovered pheromones can be used for mating disruption in cabbage looper moths... 

Another important result was obtained from in vivo experiments using the cabbage looper moth (CL), Trichoplusia ni (11). The biosynthetic pathway postulated for this insect is given in Fig 2. Substrates were applied to the gland and the (Z)-7-dodecenyl acetate isolated, cleaved at the double bond by ozonolysis, and the products isolated as benzyloximes. When acetate was used as substrate, radioactivity appeared in both products, but when hexadecanoic acid tritiated at the 16 position was used, radioactivity only appeared in the fragment derived from the terminal carbons. This demonstrated that incorporation took place as proposed in Fig 2, not by some scheme involving degradation and resynthesis. 

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