Positions and stereochemistry of methyl branches in the novel sex pheromone components produced by a lichen moth, lyclene dharma dharma

Journal of Chemical Ecology

Volumn 36, Issue 8, 2010, Pages 814-823

  Adachi, Yasushi ^a   Do, Nguyen Duc ^a   Kinjo, Masakatsu ^b   Makisako, Saori ^a   Yamakawa, Rei ^a   Mori, Kenji ^c   Ando, Tetsu ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b UNIVERSITY OF THE RYUKYUS   (Japan)

^c TOYO GOSEI CO LTD   (Japan)

Author keywords

Absolute configuration; Enantiomers; Female sex pheromone; Field evaluation of synthetic isomers; Lepidoptera; Methyl branched 2 ketones; Positional isomers; Resolution by chiral HPLC

Indexed keywords

SEX PHEROMONE;

ATTRACTANT; BIOCHEMISTRY; BIOLOGICAL CONTROL; FIELDWORK; GAS CHROMATOGRAPHY; KETONE; LICHEN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOTH; SEX PHEROMONE; TRAPPING;

ANIMAL; ARTICLE; BIOSYNTHESIS; CHEMISTRY; DRUG EFFECT; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGHT RELATED PHENOMENA; MALE; MASS FRAGMENTOGRAPHY; METABOLISM; MOTH; STEREOISOMERISM; SYNTHESIS;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MALE; MOTHS; OPTICAL PROCESSES; SEX ATTRACTANTS; STEREOISOMERISM;

IRIOMOTE; JAPAN; OKINAWA [RYUKYU ISLANDS]; RYUKYU ISLANDS;

ARCTIIDAE; HEXAPODA; LEPIDOPTERA; LITHOSIINAE;

EID: 77955053511     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-010-9813-3     Document Type: Article

References (26)

1. Ando, T. 2010. Internet database: http://www. tuat. ac. jp/~antetsu/LepiPheroList. htm.
2. Ando, T., Inomata, S., and Yamamoto, M. 2004. Lepidopteran sex pheromones. Topics Current Chem. 239: 51-96.
3. Aplin, R. T., and Birch, M. C. 1970. Identification of odorous compounds from male Lepidoptera. Experientia 26: 1193-1194.
4. Chuman, T., Guss, P. L., Doolittle, R. E., McLaughlin, J. R., Krysan, J. L., Schalk, J. M., and Tumlinson, J. H. 1987. Identification of female-produced sex pheromone from banded cucumber beetle, Diabrotica balteata LeConte (Coleoptera: Chrysomelidae). J. Chem. Ecol. 13: 1601-1616.
5. Do, N. D., Kinjo, M., Taguri, T., Adachi, Y., Yamakawa, R., and Ando, T. 2009. Synthesis and field evaluation of methyl-branched ketones, sex pheromone components produced by Lithosiinae female moths in the family of Arctiidae. Biosci. Biotechnol. Biochem. 73: 1618-1622.
6. Duff, C. M., Gries, G., Mori, K., Shirai, Y., Seki, M., Takikawa, H., Sheng, T., Slessor, K. N., Gries, R., Maier, C. T., and Ferguson, D. C. 2001. Dose pheromone biology of Lambdina athasaria and L. pellucidaria contribute to their reproductive isolation? J. Chem. Ecol. 27: 431-442.
7. El-Sayed, A. M. 2009. Internet database: http://www. pherobase. com/.
8. Fouquet, G., and Schlosser, M. 1974. Improved carbon-carbon linking by controlled copper catalysis. Angew. Chem. Int. Ed. Engl. 13: 82-83.
9. Guss, P. L., Tumlinson, J. H., Sonnet, P. E., and McLaughlin, J. R. 1983 Identification of a female-produced sex pheromone from the southern corn rootworm, Diabrotica undecimpunctata howardi Barber. J. Chem. Ecol. 9: 1363-1375.
10. Hall, D. R., Farman, D. I., Cross, J. V., Pope, T. W., Ando, T., and Yamamoto, M. 2009 (S)-2-Acetoxy-5-undecanone, female sex pheromone of the raspberry cane midge, Resseliella theobaldi (Barnes). J. Chem. Ecol. 35: 230-242.
11. Honda, K. 1980. Odor of a papilionid butterfly. Odoriferous substances emitted by Atrophaneura alcinous alcinous (Lepidoptera: papilionidae). J. Chem. Ecol. 6: 867-873.
12. King, G. G. S., Gries, R., Gries, G., and Slessor, K. N. 1995. Optical isomers of 3, 13-dimethylheptadecane: sex pheromone components of the western false hemlock looper, Nepytia freemani (Lepidoptera: Geometridae). J. Chem. Ecol. 21: 2027-2045.
13. Kiyota, R., Yamakawa, R., Iwabuchi, K., Hoshino, K., and Ando, T. 2009. Synthesis of the deuterated sex pheromone components of the grape borer, Xylotrechus pyrrhoderus. Biosci. Biotechnol. Biochem. 73: 2252-2256.
14. Li, J., Gries, R., Gries, G., Slessor, K. N., King, G. G. S., Bowers, W. W., and West, R. J. 1993a. Chirality of 5, 11-dimethylheptadecane, the major sex pheromone component of the hemlock looper, Lambdina fiscellaria (Lepidoptera: Geometridae). J. Chem. Ecol. 19: 1057-1062.
15. Li, J.-X., Gries, G., Gries, R., Bikic, J., and Slessor, K. N. 1993b. Chirality of synergistic sex pheromone components of the western hemlock looper Lambdina fiscellaria lugubrosa (Hulst) (Lepidoptera: Geometridae). J. Chem. Ecol. 19: 2547-2561.
16. Mori, K. 2009. Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 6, 14-diemthyl-2-octadecanone, and 14-methyl-2-octadecanone, the components of the female-produced sex pheromone of a moth, Lyclene dharma dharma. Tetrahedron, 65: 2798-2805.
17. Nishida, R., Fukami, H., and Ishii, S. 1974. Sex pheromone of the German cockroach (Blattella germanica L.) responsible for male wing-raising: 3, 11-dimethyl-2-nonacosanone. Experientia 30: 978-979.
18. Qin, X.-R., Ando, T., Yamamoto, M., Yamashita, M., Kusano, K., and Abe, H. 1997. Resolution of pheromonal epoxydienes by chiral HPLC, stereochemistry of separated enantiomers, and their field evaluation. J. Chem. Ecol. 23: 1403-1417.
19. Sato, R., Abe, N., Sugie, H., Kato, M., Mori, K., and Tamaki, Y. 1986. Biological activity of the chiral sex pheromone of the peach leafminer moth, Lyonetia clerkella Linné (Lepidoptera: Lyonetiidae). Appl. Entomol. Zool. 21: 478-480.
20. Schal, C., Burns, E. L., Jurenka, R. A., and Blomquist, G. J. 1990. A new component of the female sex pheromone of Blattella germanica (L.) (Dictyoptera: Blatellidae) and interaction with other pheromone components. J. Chem. Ecol. 16: 1997-2008.
21. Taguri, T., Yamakawa, R., Adachi, Y., Mori, K., and Ando, T. 2010. Improved synthesis of three methyl-branched pheromone components produced by the female lichen moth. Biosci. Biotechnol. Biochem. 74: 119-124.
22. Tamaki, Y., Sugie, H., Osakabe, M., and Sonnet, P. 1983. Biological activities of R- and S-10-methyldodecyl acetates, the chiral component of the sex pheromone of the smaller tea tortrix moth (Adoxophyes sp., Lepidoptera: Tortricidae). Appl. Entomol. Zool. 18: 292-294.
23. Tóth, M., Helmchen, G., Leikauf, U., Sziráki, G. Y., and Szöcs, G. 1989. Behavioral activity of optical isomers of 5, 9-dimethylheptadecane, the sex pheromone of Leucoptera scitella L. (Lepidoptera: Lyonetidae). J. Chem. Ecol. 15: 1535-1543.
24. Tsuji, J. 1984. Synthetic applications of the palladium-catalyzed oxidation of olefins to ketones. Synthesis. 369-384.
25. Yamamoto, M., Takeuchi, Y., Ohmasa, Y., Yamazawa, H., and Ando, T. 1999. Chiral HPLC resolution of monoepoxides derived from 6, 9-dienes and its application to stereochemistry assignment of fruit-piercing noctuid pheromone. Biomed. Chromatogr. 13: 410-417.
26. Yamamoto, M., Kamata, T., Do, N. D., Adachi, Y., Kinjo, M., and Ando, T. 2007. A Novel lepidopteran sex pheromone produced by females of a Lithosiinae species, Lyclene dharma dharma, in the family of Arctiidae. Biosci. Biotechnol. Biochem. 71: 2860-2863.