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24Th ISCE, 2008 (Novel C 20 and C 22 Trienyl Biosynthetic Precursors

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24th ISCE Annual Meeting Pennsylvania, USA (August 21, 2008) Identification of C21 Type II sex pheromone components and novel C20 and C22 trienyl biosynthetic precursors from a wasp moth, Syntomoides imaon (Arctiidae: Syntominae) Tetsu ANDO et al. Graduate School of BASE, Tokyo University of Agriculture and Technology, Tokyo 184-8588, Japan E-mail: [email protected] Diurnal moths Wasp moth Clearwing moth Pheromone: Type II ? Z3,Z13-18:OAc Hawk moth E10,E12-16:Ald 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 Arctiid species and pheromone study Taxonomy Japanese Super-family Family Sub-family species Noctuoidea Notodontidae Lymantriidae Arctiidae Lithosiinae 79 Nolidae Syntominae 4 wasp moth Pantheidae Arctiinae 51 Noctuidae In Syntominae, Type II pheromones (C21 triene and 9,10-epoxide) have been identified from two tropical species, Empyreuma mucro and Syntomeida epilais (no field data) (Descoins et al., 1989). Insects used in this study Syntomoides imaon Cramer (a wasp mimic species) Distributed in Southeast Asia, such as India and Taiwan Found only in the Yonaguni-jima Island in Japan Reared on a semisynthetic diet (16L-8D, 25oC) GC-EAD and GC-MS The pheromone gland extract of S. imaon females was analyzed by GC-EAD and GC-MS equipped with a DB-23 column. GC-EAD (0.5 FE) Mass spectra (1 FE) 79 Comp. I 100 - Comp. II 108 (%) 108 234 Comp. I 67 50 - 55 93 121 EAD 135 79 234 290 0 - 100 200 m/z 300 79 - 91 Comp. II 100 106 91 (%) 234 67 50 - 106 FID 55 119 133 79 234 16 17 18 19 288 Rt (min) 0- 100 200 m/z 300 Comp. I (Z3,Z6,Z9-21:H) Comp. II (1,Z3,Z6,Z9-21:H, 1.5 g/female) Comp. III (Z3,Z6,Z9-20:H) Comp. IV (1,Z3,Z6,Z9-20:H) I : II : III : IV = 32:67:0.6:0.7 Chemical reactions with tetraene Ex. 1) 3,6,9-triene Gland extract (20 FE) dienes tetraene N2H4 + H2O2 / EtOH 65oC, 2 hr monoenes GC-MS analysis TIC 14.0 16.0 18.0 Rt (min) Only one triene Selective reduction at 1-position Ex. 2) I Mass chromatogram at m/z 388 II Gland extract (20 FE) III N H + H O / EtOH 2 4 2 2 m/z 388 65oC, 8 hr 24.5 25.0 25.5 o Rt (min) DMDS / I2 , 40 C, 2 hr I DMDS of 9-21:H (m/z 173, 215) II DMDS of 6-21:H (m/z 131, 257) GC-MS analysis III DMDS of 3-21:H (m/z 89, 299) 1,3,6,9-tetraene Field tests Ordinal wasp moth in Japan Amata fortunei Z3,Z6,Z9-21:H & other components (without tetraene) *Syntomoides imaon Triene Tetraene Total males 0.5 mg 1.0 mg 31 1.0 0 0 0 1.0 0 * Z3,Z6,Z9-21:H 0 0 0 & 1,Z3,Z6,Z9-21:H From 28 June to 5 July, 2007 Future works: the optical mixing ratio, roles of minor C20 compounds and visual cues, and etc. Identification of tetraenes C21 C19 Epirrita autumnata (Geometridae) Operophtera brumata Arctia villica (Arctiidae) O. bruceata (Geometridae) Utetheisa ornatrix (Arctiidae) Biosynthesis of Type II pheromones Confirmed step Hemolymph Unconfirmed step Linolenic acid Z9,Z12,Z15-18:Acid Head PBAN 3 6 Z11,Z14,Z17-20:Acid Ingestion 2 Z3,Z6,Z9-19:H SG PBAN 1 5 Z3,Z6,Z9-19:H Lipophorin OenocyteOenocyte 4 epo3,Z6,Z9-19:H Pheromone gland 1 Specific epoxidation (Miyamoto et al., 1999. IBMB, 29: 63) 2 Transportation in hemolymph (Wei et al., 2003. IBMB, 33: 397) C19 triene & epoxide 3 Mode of action of PBAN (Wei et al., 2004. IBMB, 34: 1215) 4 Lipophorin association (Matsuoka et al., 2006. IBMB, 36: 576) 5 Identification of PBAN (Kawai et al., 2007. IBMB, 37: 330) Geometrid moth 6 Structure of pheromone gland (Fujii et al., 2007. JIP, 53: 312) C21 triene desaturation New subject + tetraene Z9,Z12,Z15-18:Acid Z9,Z12,Z15,17-18:Acid -oxidation Z11,Z14,Z17-20:Acid Z11,Z14,Z17,19-20:Acid Identification of these long-chain fatty Z13,Z16,Z19-22:Acid Z13,Z16,Z19,21-22:Acid acids, candidates of Oenocyte biosynthetic Z3,Z6,Z9-21:H 1,Z3,Z6,Z9-21:H Wasp moth Oenocyte precursors Analysis of fatty acids Abdominal integument with oenocytes and peripheral fat bodies Extraction, basic methanolysis, methylation with CH2N2 Mixture of fatty acid methyl esters (FAMEs) biosynthetic GC-MS X HPLC separation (ODS column) precursors Fractions including a long-chain fatty acid ester (A) HPLC Rts of FAMEs Triene diene monoene saturated 2 4 C16 C17 Column: ODS Eluent: 13 5 C18 5% water C19 in MeOH C20 (1.0 ml/min) C21 10 20 30 40 C22 50 Rt (min) (B) Fractionation of S. imaon FAMEs (1 female) 1 GC-MS 3 Fr. A (14-15 min) C20 trienyl o 1 18:3 2 16:1 C20 tetraenyl 3 18:2 4 16:0 Fr. B (18-20 min) X 5 18:1 5 2 4 Fr. C (20-22 min) C22 trienyl o 210 nm 10 20 30 40 50 Rt (min) GC-MS of HPLC fractions Fr. A (14-15 min) 79 100 - 108 264 20:3 O ester (%) 95 OMe 108 50 - 79 TIC M+ 264 289 320 18 20 22 Rt (min) 0 - 100 200 300 m/z 79 Fr. C (20-22 min) 100 - 108 292 22:3 (%) 95 O ester 108 OMe 50 - 79 TIC M+ 292 317 348 18 20 22 Rt (min) 0 - 100 200 300 m/z Ion fragments lower than m/z 150 in the spectra of the 20:3 and 22:3 esters were identical to those of the ester of linolenic acid (18:3), indicating the same trienyl structure. Relative contents; 16:0 (0.3 mg/female, 100%), 20:3 (0.08%), 22:3 (0.03%) Unsaturated positions of C20 trienoate Diimide reduction Fr. A (14-15 min) Mixture of monoenyl esters 20:3 ester DMDS / I 2 GC-MS analysis DMDS adducts of monoenyl esters (A) (B) (C) m/z 173 173 245 m/z 245 SCH H3CS 11 3 O (A) m/z 213 OMe 213 25 26 27 Rt.(min) m/z 131 131 287 H3CS SCH3 m/z 287 14 OMe (B) m/z 255 255 O 25 26 27 Rt.(min) 89 329 m/z 89 H CS SCH3 O 3 17 m/z 329 (C) OMe m/z 297 297 25 26 27 Rt.(min) Methyl ester of 11,14,17-20:Acid Summery Female wasp moths produce Type II pheromones, a mixture of C21 triene and tetraene to attract males. Fatty acid methyl esters (FAMEs) derived from lipids were fractionated by HPLC. GC-MS analysis revealed novel C20 and C22 trienoates, longer-chain analogs of linolenate. In the another experiment with the geometrid moth, which produces C19 pheromone components, only C20 trienoate was detected. Different systems of the chain elongation might play an important role in developing species-specific communication systems mediated with polyunsaturated hydrocarbons and derivatives, components of Type II lepidopteran sex pheromones. Recent related studies 1) Biosynthesis of tetraene in Utetheisa ornatrix (Arctiidae: Arctiinae) Choi et al., 2007. JCE, 33: 1336 “D4-Z3,Z6,Z9-21:H was injected into pupae. No label was incorporated into 1,Z3,Z6,Z9-21:H, indicating that the terminal double bond is introduced earlier in the biosynthetic pathway.” Tetraenyl acid intermediate was not detected in our study. Is the step of desaturation linked effectively with decarboxylation? 2) Biosynthesis of even numbered triene in Erannis bajaria (Geometridae) Goller et al., 2007. JCE, 33: 1505 “D4-Z3,Z6,Z9-18:H was detected after treatment of D4-trienyl C19 or C20 acid. The result indicates that the C20 acid is shorted by -oxidation to C19 acid, which can be reduced to an aldehyde and decarbonylated or decarboxylated to the pheromone component.” Biosynthesis of odd numbered triene has not been experimentally confirmed. Where is decarboxylation carried out? Acknowledgments Co-workers Dr. M. Muramatsu The Ayamihabiru Museum, Okinawa, Japan Dr. H. Naka JT Biohistory Research Hall, Osaka, Japan Dr. Y. Kondo Gifu University, Gifu, Japan Chemical Ecology Laboratory of TUAT Dr. M. Yamamoto K. Matsuoka MD. A. Islam R. Yamakawa N. D. Do Y. Adachi A. Yasmine R. Kiyota.
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    SHILAP Revista de Lepidopterología ISSN: 0300-5267 [email protected] Sociedad Hispano-Luso-Americana de Lepidopterología España Lu, H. F.; Chen, F. Q.; Wu, C. S. Catalogue of Ctenuchinina Heppner, 1992 from China (Lepidoptera: Erebidae, Arctiinae) SHILAP Revista de Lepidopterología, vol. 40, núm. 160, diciembre, 2012, pp. 447-463 Sociedad Hispano-Luso-Americana de Lepidopterología Madrid, España Available in: http://www.redalyc.org/articulo.oa?id=45526984008 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative 447-463 Catalogue of Ctenuchini 4/12/12 20:07 Página 447 SHILAP Revta. lepid., 40 (160), diciembre 2012: 447-463 CODEN: SRLPEF ISSN:0300-5267 Catalogue of Ctenuchinina Heppner, 1992 from China (Lepidoptera: Erebidae, Arctiinae) H. F. Lu, F. Q. Chen & C. S. Wu Abstract A total of 86 valid species in 7 genera of Ctenuchinina Heppner, 1992 (6 genera of Syntomini and 1 genus of Euchromiini) are included in this catalogue, of which 6 species are newly recorded for China. The references for each species and known synonyms are given. The distribution of each species is also reported. KEY WORDS: Lepidoptera, Erebidae, Arctiinae, Ctenuchinina, catalogue, China. Catálogo de los Ctenuchinina Heppner, 1992 de China (Lepidoptera: Erebidae, Arctiinae) Resumen Se incluyen en este catálogo un total de 86 especies válidas en 7 géneros de Ctenuchinina Heppner, 1992 (6 géneros de Syntomini y 1 género de Euchromiini), de las cuales 6 especies son nuevos registros para China.
  • 【令和2年度】川口いきもの調査結果 (Pdfファイル: 91.6Kb)

    【令和2年度】川口いきもの調査結果 (Pdfファイル: 91.6Kb)

    令和２年度 川口いきもの調査 結果 ほ乳類 目名 科名 種名 学名 中央 横曽根 青木 南平 新郷 神根 芝 安行 戸塚 鳩ヶ谷 不明 コウモリ目（翼手目） ヒナコウモリ科 アブラコウモリ Pipistrellus abramus 〇 ネコ目（食肉目） イヌ科 タヌキ Nyctereutes procyonoides 〇〇 〇〇 鳥類 目名 科名 種名 学名 中央 横曽根 青木 南平 新郷 神根 芝 安行 戸塚 鳩ヶ谷 不明 カイツブリ目 カイツブリ科 カイツブリ Tachybaptus ruficollis 〇 〇 〇〇 カイツブリ目 カイツブリ科 カンムリカイツブリ Podiceps cristatus 〇 〇 カイツブリ目 カイツブリ科 ハジロカイツブリ Podiceps nigricollis 〇 カツオドリ目 ウ科 カワウ Phalacrocorax carbo 〇〇〇〇 〇 〇 カッコウ目 カッコウ科 ホトトギス Cuculus poliocephalus 〇 カモ目 カモ科 オカヨシガモ Anas strepera 〇 カモ目 カモ科 オナガガモ Anas acuta 〇 〇 〇〇 カモ目 カモ科 カモ科の一種 Anatidae sp. 〇 〇 カモ目 カモ科 カルガモ Anas zonorhyncha 〇〇〇 〇〇〇 カモ目 カモ科 キンクロハジロ Aythya fuligula 〇〇 〇〇〇 カモ目 カモ科 コガモ Anas crecca 〇〇 〇〇 カモ目 カモ科 コハクチョウ Cygnus columbianus 〇 カモ目 カモ科 スズガモ Aythya marila 〇 〇 カモ目 カモ科 ハシビロガモ Anas clypeata 〇 カモ目 カモ科 ヒドリガモ Anas penelope 〇〇〇 〇〇 カモ目 カモ科 ホシハジロ Aythya ferina 〇〇〇 〇〇〇 カモ目 カモ科 マガモ Anas platyrhynchos 〇 〇 〇 カモ目 カモ科 ヨシガモ Anas falcata 〇 キジ目 キジ科 キジ Phasianus colchicus 〇 キジ目 キジ科 コジュケイ Bambusicola thoracicus 〇 〇 キツツキ目 キツツキ科 アリスイ Jynx torquilla 〇 キツツキ目 キツツキ科 コゲラ Dendrocopos kizuki 〇 〇 コウノトリ目 コウノトリ科 コウノトリ Ciconia boyciana 〇 スズメ目 アトリ科 カワラヒワ Chloris sinica 〇 〇 〇 〇〇〇 スズメ目 カササギヒタキ科 サンコウチョウ Terpsiphone atrocaudata 〇 スズメ目 カラス科 オナガ Cyanopica cyanus 〇 〇〇 〇〇〇 スズメ目 カラス科 カケス Garrulus glandarius 〇 〇〇〇 スズメ目 カラス科 カラス科の一種 Corvibae sp. 〇 〇 スズメ目 カラス科 ハシブトガラス Corvus macrorhynchos 〇 〇 スズメ目 カラス科 ハシボソガラス Corvus corone 〇〇〇〇 〇〇 〇 スズメ目 シジュウカラ科 シジュウカラ Parus minor 〇〇 〇〇〇 スズメ目 スズメ科 スズメ Passer montanus 〇〇 〇〇 スズメ目 セキレイ科 キセキレイ Motacilla cinerea 〇 スズメ目 セキレイ科 セグロセキレイ Motacilla grandis 〇 〇 スズメ目 セキレイ科 ハクセキレイ Motacilla alba 〇 〇〇 〇〇 〇 スズメ目 セッカ科 セッカ
  • Hemiptera): a Synthesis

    Hemiptera): a Synthesis

    Insects 2014, 5, 577-595; doi:10.3390/insects5030577 OPEN ACCESS insects ISSN 2075-4450 www.mdpi.com/journal/insects/ Review Semiochemical and Vibrational Cues and Signals Mediating Mate Finding and Courtship in Psylloidea (Hemiptera): A Synthesis Umar K. Lubanga 1,*, Christelle Guédot 2, Diana M. Percy 3 and Martin J. Steinbauer 1 1 Department of Zoology, La Trobe University, Melbourne, Victoria 3086, Australia; E-Mail: [email protected] 2 Department of Entomology, University of Wisconsin, Madison, WI 53706, USA; E-Mail: [email protected] 3 Natural History Museum, London, SW7 5BD, UK; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +61-4055-2667. Received: 12 May 2014; in revised form: 7 July 2014 / Accepted: 10 July 2014 / Published: 21 July 2014 Abstract: Mate finding and courtship involve complex interactions that require close coordination between individuals of the opposite gender. Well-organized signalling systems, sometimes involving a combination of signal modalities, are required to convey species-specific and individual information to members of the opposite gender. Previous studies of psyllids have focused on single-signal modalities and have largely ignored the potentially interdependent nature of different types of signals. Several studies have shown that semiochemicals play a role in psyllid mate finding. However, long-range semiochemical sex attractants, such as the highly volatile sex pheromones used by many Lepidoptera (molecular weights <300), are yet to be identified. The compounds identified thus far, namely 13-methylheptacosane (from Cacopsylla pyricola) and dodecanoic acid (from Diaphorina citri), seem to have short range activity or no activity under field conditions.