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33Rd ISCE, 2017 (GC/FT-IR Analysis of a Novel 2,4,6,9-Tetraene)

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2017 ISCE/APACE Kyoto, Japan (August 24, 2017) GC / FT-IR analysis of a novel 2,4,6,9-tetraene occurring in a female pheromone gland of Parasemia plantaginis (Lepidoptera: Arctiidae) Yuta Muraki, Hideshi Naka, Atsushi Honma, Johanna Mappes, Kaisa Suisto, and Tetsu Ando* * Tokyo University of Agriculture and Technology, JapanJapan JICA, Can Tho University, Vietnam E-mail: [email protected] 3000 2000 1000 (cm-1) Representative lepidopteran sex pheromones Sex pheromones have been identified from more than 670 species. Male attractants have been reported for other 1300 species. Type I rice stem borer silkworm moth smaller tea tortrix 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 Polyunsaturated hydrocarbons and Z3,Z6,Z9-21:H epo3,Z6,Z9-19:H Z3,epo6,Z9-19:H their epoxides with a C17 –C23 chain Identified from evolved-insect groups (15%) plum cankerworm moth Milionia basalis giant geometrid moth Photos from http://www.jpmoth.org/ Phylogenetic tree of Lepidoptera yellow peach moth E10-16:Ald satin moth Z3,Z6,Z9-23:H plum cankerworm moth Z3,epo6,epo9-21:H Z3,Z6,Z9-21: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 Chemical structures of Type II pheromones Linoleic acid secretion O Z6,Z9-dienes OH E4,Z6,Z9-trienes mono- Z6,Z9,E11-trienes epoxides desaturation Z6,Z9,Z12-trienes Δ12 CnH2n+1 Δ4 Δ11 emerald moth secretion Linolenic acid O Z3,Z6,Z9-trienes OH 1,Z3,Z6,Z9-tetraenes mono- and Z3,Z6,Z9,E11-tetraenes di-epoxides desaturation Z3,Z6,Z9,Z11-tetraenes CnH2n+1 Δ1 Δ11 The known chemical diversity is still limited. Novel compounds must be found. Noctuoidea species and their sex pheromones Taxonomy Type of Japanese Super-family Family Sub-family pheromone species number Noctuoidea Notodontidae I 124 [0] Nolidae II 107 [0] Noctuidae <Trifinae> I 787 [34] <Quadritinae>* II, others 489 [4] Lymantriidae* II, others 59 [16] Arctiidae* Lithosiinae II, others 79 [4] Syntominae II 4 [1] *Erebidae Arctiinae II, others 51 [3] [ ] indicate number of species whose sex pheromone has been identified. Parasemia plantaqinis, wood tiger moth (Arctiidae; Arctiinae) Four subspecies are recorded in Japan. P. p. macromera P. p. melanissima P. p. jezoensis P. p. melanomera GC-EAD analysis of the pheromone extract Parasemia plantaqinis, wood tiger moth (Arctiidae; Arctiinae) Four subspecies are recorded in Japan. P. p. macromera P. p. melanissima P. p. jezoensis P. p. melanomera Comp. I Crude pheromone Z3,Z6,Z9-21:H Comp. I Comp. III extract (1.0 FE) Comp. II Comp. IV EAD GC column: 0.1 mV DB-23 (0.25 mm X 30 m) Temperature program: Mixing ratio 80ºC (1 min) → I : II : III : IV ≑ 30:3:5:1 210ºC (10ºC/min) FID 18.0 20.0 22.0 Rt (min) GC / MS analysis of the pheromone extract Comp. II 79 E4,Z6,Z9-21:H 247 100 194 93 121 79 M+ 107 135 121 149 135 290 194 247 I 0 Crude pheromone 50 100 150 200 250 300 m/z extract (1.0 FE) Comp. III 1,Z3,Z6,Z9-21:H 133 79 91 106 100 91 III 106 79 119 234 II M+ IV 133 234 147 288 0 TIC 50 100 150 200 250 300 m/z Comp. IV 2,4,6,9-tetraene ? 20.0 133 18.0 Rt (min) 94 105 100 91 GC column: 79 DB-23 91 105 94 (0.25 mm X 30 m) 119 220 M+ 133 288 Temperature program: 147 220 0 80ºC (1 min) → 50 100 150 200 250 300 m/z 210ºC (8ºC/min) GC / FT-IR No information on the configurations Merits of IR analysis O-H cis trans OH Double bond Number 2 Functional group OH Position 10, 12 Carbon chain length 16 Configuration E, Z Determined by the IR spectrum, if a large amount of the pure pheromone is available. IR analysis is not utilized, because the species-specific pheromones are composed of multiple components, which are produced at μg level, at most. GC / FT-IR Lq. N2 <Spectra Analysis, Inc.> Capillary GC High separation FT-IR (solid phase) High sensitivity Familiarized spectrum ® Discover IR GC capillary IR beam ZnSe disk cooled at −30ºC Detector IR spectra of four EAG-active components Measured by GC / FT-IR Disk temperature: −30ºC Crude extract (4 FE) 2918 Disk speed: 2 mm/min 2965 Comp. I 970 728 3007 2851 Z3,Z6,Z9-21:H 1472 1396 935 2919 Comp. II 2958 E4,Z6,Z9-21:H 2852 951 3013 1473 983 2919 Comp. III 2954 1,Z3,Z6,Z9-21:H 899 3010 1000 2853 2921 Comp. IV Conjugated 2957 2853 Z2,E4,Z6,Z9-21:H Z,Z-diene 992 765 3020 1470 941 3040 3000 2000 1000 (cm-1) Comp. IV includes E,Z conjugated systems, and no Z,Z conjugation. Synthesis of 2,4,6,9-tetraene _ + + _ Br Br Br• Ph3 PPPh3•Br Ph3P PPh3 O O O H H H Poor yield (< 5%), but a very simple route GC / FT-IR analyses of natural and synthetic 2,4,6,9-tetraene [Peak chromatogram] Crude extract 2921 Comp. IV I Crude extract (4 FE) 766 3020 942 993 III II IV good coincident Synthetic 2921 20.0 22.0 Z2,E4,Z6,Z9-21:H 766 942 3020 993 E2,E4 2921 Synthetic Synthetic Z2,E4 996 E2,E4,Z6,Z9-21:H 752 3017 20.0 22.0 Rt (min) Column: HP-5 (0.25 mm X 30 m) 3000 2000 1000 (cm-1) Summary & discussion 1) Four EAG-active components were found in the pheromone grand of P. p. melanomera and a Finnish subspecies. 2) GC/MS and GC/FT-IR analyses showed the following structures. Comp. I Z3,Z6,Z9-21:H ( ← linolenic acid) Comp. II E4.Z6,Z9-21:H ( ← linoleic acid) Comp. III 1,Z3,Z6,Z9-21:H ( ← linolenic acid) Comp. IV Z2,E4,Z6,Z9-21:H ( ← linoleic acid) Mixing ratio; I : II : III : IV ≑ 30 : 3 : 5 : 1 3) An IR spectrum of the minor Comp. IV measured by a high-sensitive GC/FT-IR instrument indicated its 2Z,4E configuration. 4) The structure of Comp. IV was confirmed by synthesis utilizing the double Wittig reaction. 5) Male attraction by synthetic lures in the field has not succeeded, indicating necessity of additional pheromone component(s). Thank you for attention !! Present address: Can Tho University (CTU) in Can Tho City, Vietnam Chief advisor of JICA’s project for “Building Capacity for CTU” I retired Tokyo University of Agriculture and Technology (TUAT) in 2015. I retired Tokyo University of Agriculture and Technology (TUAT) in 2015. I am grateful to all member of Chemical Ecology Laboratory of TUAT, I am gratefulwho studiedto all member lepidopteran of Chemical sex pheromones Ecology Laboratory together. of TUAT for study of lepidopteran sex pheromones. https://lepipheromone.sakura.ne.jp/index_eng.html.
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    Lepidoptera Conservation Bulletin Number 11 April 2010 – March 2011 Butterfly Conservation Report No. S11-13 Compiled & Edited by B. Noake (Conservation Officer – Threatened Species), A. Rosenthal (Conservation Officer – Threatened Species), M. Parsons (Head of Moth Conservation) & Dr. N. Bourn (Director of Conservation) March 2011 Butterfly Conservation Company limited by guarantee, registered in England (2206468) Registered Office: Manor Yard, East Lulworth, Wareham, Dorset. BH20 5QP Charity registered in England and Wales (254937) and in Scotland (SCO39268) www.butterfly-conservation.org Noake. B., Rosenthal, A., Parsons, M. & Bourn, N. (eds.) (2011) Lepidoptera Conservation Bulletin Number 11: April 2010 – March 2011, Butterfly Conservation, Wareham. (Butterfly Conservation Report No. S11-13) Contents 1 INTRODUCTION ................................................................................................................................................. 1 2 ACKNOWLEDGMENTS ....................................................................................................................................... 2 3 CONSERVATION ACTION FOR UK BIODIVERSITY ACTION PLAN LEPIDOPTERA ................................................... 2 3.1 UPDATE ON UK BAP MOTHS – A SUMMARY FOR THE YEAR 2010 ........................................................................................... 3 Anania funebris.........................................................................................................................................................