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27Th ISCE, 2011 (Epoxytrienes Derived from (3Z,6Z,9Z)-1,3,6,9-Tetraenes)

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27Th ISCE, 2011 (Epoxytrienes Derived from (3Z,6Z,9Z)-1,3,6,9-Tetraenes) 27th ISCE Annual Meeting Vancouver, Canada (July 25, 2011) Characterization of Epoxytrienes Derived from (3Z,6Z,9Z)-1,3,6,9-Tetraenes, Sex Pheromone Components of Arctiid Moths and Related Compounds T. Ando, R. Yamakawa, and Y. Takubo O Graduate School of BASE, Tokyo University of Agriculture and Technology, Tokyo 184-8588, Japan E-mail: [email protected] Representative lepidopteran sex pheromones Sex pheromones have been identified from about 620 species. Male attractants have been reported for other 1200 species. Type I Silkworm moth Smaller tea tortix Rice stem borer Unsaturated fatty OH O H alcohols, acetates bombykol OAc O and aldehydes with H OA c a C10 –C18 chain Found most commonly (75%) Type II O O O Polyunsaturated hydrocarbons and epo3,Z6,Z9-19:H Z3,epo6,Z9-19:H Z3,Z6,epo9-18:H their epoxides with a C17 –C23 chain Identified from evolved-insect groups (15%) Milionia e basalis Giant geometrid moth Mulberry looper Phylogenetic tree of Lepidoptera Lichen moth Yellow peach moth Plum cankerworm moth Z3,Z6,Z9-21:H E10-16:Ald Z3,Z6,Z9-21:H Z3,Z6,Z9-23:H Z3,Z6,Z9-23:H Z3,Z6,Z9-23:H Noctuoidea Bombycoidea Papillionoidea Geometroidea Sesioidea Pyraloidea Hesperioidea Pterophoroidea Zygaenoidea Gelechioidea Tortricoidea Yponomeutoidea Cossoidea Castnioidea Tineoidea Hepialoidea Incurvarioidea Nepticuloidea Ditrysia Eriocranioidea Monotrysia Zeugloptera Dacnonypha Type I pheromone Type II pheromone Paramecoptera Speciation of the groups, which produce Type II pheromones Taxonomy Type of Japanese Super-family Family Sub-family pheromone species Geometroidea Uraniidae Geometridae Ennominae II, others 339 Geometrinae II 86 Sterrhinae I 109 Larentiinae II 346 Alsophilinae II 14 Noctuoidea Notodontidae I 124 Lymantriidae II, others 59 Nolidae II 107 Noctuidae I, II, others 1276 Pantheidae 13 Arctiidae Lithosiinae II, others 79 Syntominae II 4 Arctiinae II, others 51 BiosynthesisRepresentative of Typelepidopteran II sex pheromones sex pheromones Sex pheromonesOenocyte have been identified from about 620 species. Male attractants have been reporO ted for other 1200 species. Type I OH Chain elongation Silkworm moth Smaller tea tortix Rice stem borer Unsaturated fatty Decarboxylation OH O alcohols, acetates R H and aldehydes with bombykol OAc O a C10 –C18 chain OA c H Transport by lipophorin Biosynthesized in a pheromone gland Pheromone gland from acetyl-CoA Epoxidation Type II O O O Polyunsaturated hydrocarbons and epo3,Z6,Z9-19:H Z3,epo6,Z9-19:H Z3,Z6,epo9-18:H their epoxides with a C17 –C23 chain Identified from evolved-insect groups (15%) Milionia e basalis Giant geometrid moth Mulberry looper Biosynthesis of Type II sex pheromones Oenocyte Desaturation O O OH OH n Chain elongation Decarboxylation R R Transport by lipophorin Transport by lipophorin Pheromone gland Pheromone gland Epoxidation Epoxidation EpoxytrienesType II O O O O Polyunsaturated ? hydrocarbonsO and epo3,Z6,Z9-19:H Z3,epo6,Z9-19:H Z3,Z6,epo9-18:H their epoxides withO a C17 –C?23 chain Identified from O evolved-insect Fall webworm ? groups (15%) Milionia e basalis Giant geometrid moth MulberryMulberry tiger looper moth Synthesis of epoxytrienes O O HO + H H R OH Ph3P PPh3 Double-Wittig reaction MCPBA Mixture of epoxytrienes 1,Z3,Z6,Z9-21:H MPLC Lobar column (LiChroprep Si 60) O eluent: 0.5% THF in Hx flow rate: 3.0 ml/min 3,4-epoxide detector: RI 6,7-epoxide O 9,10-epoxide 3,4-epoxide 6,7-epoxide O 9,10-epoxide 1,2-Epoxide was not produced. 20 25 30 Rt (min) 4 1H NMR Synthesis of epoxytrienes6 7 9 10 5 8 1 O O 11 HO2 3 + 1 H H R 1,Z3,Z6,Z9-21:H OH Ph3P PPh3 Double-Wittig reaction 6.07 10 5.0 4.0 3.0 2.0 9 6 MCPBA 8 1 1 Mixture of epoxytrienes11 2 4 3 5 5 1,Z3,Z6,Z9-21:H 3,4-epoxide MPLC Lobar column (LiChroprep Si 60) O eluent: 0.5% THF 4in Hx 1 6 7 11 flow rate: 3.0 ml/min10 9 1 3,4-epoxide8 detector:2 3 RI 6,7-epoxide O 5 5 6,7-epoxide 9,10-epoxide 3,4-epoxide 6,7-epoxide 6 9 O 7 10 1 5 2 3 1 9,10-epoxide 4 8 8 9,10-epoxide 1,2-Epoxide was not produced. 20 25 30 Rt (min) 6.0 5.0 4.0 3.0 2.0(ppm) The 9,10-epoxytriene characteristically showed some ions Mass spectra (1) corresponding to diagnostic ions of the 9,10-epoxydiene. The terminal double bond did not effect strongly on the fragmentation. 122 Z3,Z6,epo9-21:H 108 -H O 100 79 R 108 -H -H 183 93 79 50 183 197 X 5 M+ 122 151 197 306 Relative intensity (%) intensity Relative 0 50 100 150 200 250 300 m/z 1,Z3,Z6,epo9-21:H 120 106 100 106 -H O 91 R -H -H 79 183 50 79 197 183 X 5 M+ 120 149 197 304 Relative intensity (%) intensity Relative 0 50 100 150 200 250 300 m/z Similar fragmentations were also observed for compounds Mass spectra (2) with a C and C chain. 19 21 248 O m/z 79 (100%) 1,epo3,Z6,Z9-21:H R 263 -H 100 79 -H 79 O -H 234 R 50 -H 79 M+ 234 263 -H 234 304 Relative intensity (%) intensity Relative 0 50 100 150 200 250 300 m/z 111 97 -H O m/z 67 (100%) 1,Z3,epo6,Z9-21:H 109 R 95 -H 100 79 -H O 223 237 R 109 50 95 79 M+ 149 149 304 Relative intensity (%) intensity Relative 0 50 100 150 200 250 300 m/z These diagnostic fragment ions are useful to find new pheromone components. Resolution of epoxytrienes by chiral HPLC Chiralpak AY-H O 0.1 % 2-propanol in Hx 0.5 ml/min 1,Z3,Z6,epo9-21:H UV 215 nm Fr. A O Fr. B O R,S H2 / Pd-C 10 15 Rt (min) 20 H / Pd-C O R,S 2 Fr. A O R,S epo3,Z6,Z9-21:H Z3,epo6,Z9-21:H S,R-isomer 1,epo3,Z6,Z9-21:H 1,Z3,epo6,Z9-21:H R,S-isomer Stereochemistry of the H. cunea pheromone (1) (A) GC-MS analysis III DB-23 I (0.25 mm x 30 m) II IV Fall webworm Hyphantria cunea (Arctiidae) 18 20 22Rt (min) 24 O (B) Preparative HPLC I H Z9,Z12-18:Ald Inertsil ODS IV O (4.6 mm x 25 cm) II H 3.5 % H2O in MeOH Z9,Z12,Z15-18:Ald 1.0 ml/min O UV 215 nm III III 50 females Z3,Z6,epo9-21:H O IV 0 10 20 Rt (min) 1,Z3,Z6,epo9-21:H Stereochemistry of the H. cunea pheromone (2) (C) Chiral HPLC IV R,S S,R Chiralpak AY-H 0.1 % 2-propanol in Hx III 0.5 ml/min UV 215 nm R,S S,R A B C 0 5 10 15 Rt (min) A: Synthetic racemic mixtures (10 g of III and 1 g of IV) B: Natural pheromone (Fr. IV, 1,Z3,Z6,epo9-21:H) (9S,10R)-Isomers C: Natural pheromone (Fr. III, Z3,Z6,epo9-21:H) Male attraction in the fields Further studies Epoxytrienes derived from 1,Z3,Z6,Z9-tetraenes 1. Synthesis and characterization of 1,2-epoxytrienes 2. Field screening tests of the synthetic pheromone candidates to find new male attractants of the species in Arctiidae, Geometridae, and etc. Epoxy compounds derived from Z6,Z9,E11-trienes and Z3,Z6,Z9,E11-tetraenes 1. Synthesis of a mixture of epoxides and separation by MPLC 2. GC-MS analysis to find diagnostic fragment ions 3. Optical resolution by chiral HPLC Tussock moth Winter moth Orgyia postica Inurois fletcheri (Lymantriidae) (Geometridae) (attractant) O Wakamura et al.,Tetrahedron Lett., 42, 687 Yamamoto et al., 2008 J. Chem. Ecol., 34, 1057 Acknowledgments Drs. F. Mochizuki and T. Fukumoto Shin-etsu Chemical Co., Ltd. for supplying starting materials for syntheses. Chemical Ecology Laboratory of TUAT N. D. Do Dr. M. Yamamoto Y. Takubo Dr. R. Yamakawa H. Shibasaki R. Maruyama Y. Murakami.
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