Cabbage looper moth, pheromone

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). 

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. 

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. 

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

The activity does not sediment in a 100,000 g fraction, indicating it is soluble. A similar activity may be observed in preparations from the pheromone gland of the cabbage looper moth (21). 

The importance of elucidation of pathways of biosynthesis which regulate pheromone production is exemplified by the identification of additional pheromone components for the cabbage looper moth. 

Sex pheromones are usually emitted by females to attract males for mating. They have been reported from many moths and certain families of beetles, including Anobiidae, Bruchidae and Dermestidae, in which adults are relatively short lived and feed very little or not at all (Burkholder and Ma, 1985). Rarely, the male attracts the female, as in the cabbage looper moth (Landolt and Heath, 1990) and the arctiid moth Estigmene acrea (Willis and Birch, 1982). 

Landolt, P.J. and Heath, R.R. (1990) Attraction of female cabbage looper moths (Lep-idoptera Noctuidae) to male-produced sex pheromone. Annals of the Entomological Society of America 82, 520-525. 

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