Literature DB >> 12564803

1-Octen-3-ol together with geosmin: new secretion compounds from a polydesmid millipede, Niponia nodulosa.

Hisashi Omura1, Yasumasa Kuwahara, Tsutomu Tanabe.   

Abstract

The small millipede Niponia nodulosa (Polydesmida: Cryptodesmidae) emits an earthy smell when disturbed. This smell was obtained from hexane extracts from both sexes at the sixth and seventh instars and adult stages, and was found by GC/MS analyses to be composed of two compounds, 1-octen-3-ol as the major component and geosmin as the minor component. This is the first report of these compounds in secreted substances from millipedes. As they showed little repellent activity against foraging ants in bioassays, their biological function as defensive allomones was not clearly elucidated. However, both compounds provoked negative chemotaxis of conspecific millipedes in a Y-tube olfactometer, especially 1-octen-3-ol, which was active at a dose equivalent to the content of a single millipede. Such biological activity suggests that this compound is involved in intraspecific communication in this millipede and may play a role as an alarm pheromone.

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Year:  2002        PMID: 12564803     DOI: 10.1023/a:1021400606217

Source DB:  PubMed          Journal:  J Chem Ecol        ISSN: 0098-0331            Impact factor:   2.626


  13 in total

1.  Species-specific production of microbial volatile organic compounds (MVOC) by airborne fungi from a compost facility.

Authors:  G Fischer; R Schwalbe; M Möller; R Ostrowski; W Dott
Journal:  Chemosphere       Date:  1999-08       Impact factor: 7.086

2.  1-Octen-3-ol, a banana slug antifeedant from mushrooms.

Authors:  W F. Wood; C L. Archer; D L. Largent
Journal:  Biochem Syst Ecol       Date:  2001-05       Impact factor: 1.381

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Authors:  T Eisner; J Meinwald
Journal:  Science       Date:  1966-09-16       Impact factor: 47.728

4.  Intermediates in the biosynthesis of HCN and benzaldehyde by a polydesmid millipede, Harpaphe haydeniana (Wood).

Authors:  S S Duffey; E W Underhill; G H Towers
Journal:  Comp Biochem Physiol B       Date:  1974-04-15

5.  Geosmin and methylisoborneol biosynthesis in streptomycetes. Evidence for an isoprenoid pathway and its absence in non-differentiating isolates.

Authors:  R Bentley; R Meganathan
Journal:  FEBS Lett       Date:  1981-03-23       Impact factor: 4.124

6.  Geosmin, an earthly-smelling substance isolated from actinomycetes.

Authors:  N N Gerber; H A Lechevalier
Journal:  Appl Microbiol       Date:  1965-11

7.  Polyzonimine: A novel terpenoid insect repellent produced by a milliped.

Authors:  J Smolanoff; A F Kluge; J Meinwald; A McPhail; R W Miller; K Hicks; T Eisner
Journal:  Science       Date:  1975-05-16       Impact factor: 47.728

8.  2-Nitroethenylbenzenes as natural products in millipede defense secretions.

Authors:  Yasumasa Kuwahara; Hisashi Omura; Tsutomu Tanabe
Journal:  Naturwissenschaften       Date:  2002-07

9.  Secretion of Benzaldehyde and Hydrogen Cyanide by the Millipede Pachydesmus crassicutis (Wood).

Authors:  M S Blum; J P Woodring
Journal:  Science       Date:  1962-10-26       Impact factor: 47.728

10.  1,2-Dialkyl-4(3H)-quinazolinones in the defensive secretion of a millipede (Glomeris marginata).

Authors:  Y C Meinwald; J Meinwald; T Eisner
Journal:  Science       Date:  1966-10-21       Impact factor: 47.728

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  10 in total

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Authors:  Thorben Nawrath; Jeroen S Dickschat; Rolf Müller; Jiaoyang Jiang; David E Cane; Stefan Schulz
Journal:  J Am Chem Soc       Date:  2007-12-21       Impact factor: 15.419

2.  Release of hydrogen cyanide via a post-secretion Schotten-Baumann reaction in defensive fluids of polydesmoid millipedes.

Authors:  Yasumasa Kuwahara; Nobuhiro Shimizu; Tsutomu Tanabe
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3.  Millipede Defensive Compounds Are a Double-Edged Sword: Natural History of the Millipede-Parasitic Genus Myriophora Brown (Diptera: Phoridae).

Authors:  John M Hash; Jocelyn G Millar; John M Heraty; James F Harwood; Brian V Brown
Journal:  J Chem Ecol       Date:  2017-01-11       Impact factor: 2.626

4.  Chemical polymorphism in defense secretions during ontogenetic development of the millipede Niponia nodulosa.

Authors:  Yasumasa Kuwahara; Yayoi Ichiki; Masashi Morita; Tsutomu Tanabe; Yasuhisa Asano
Journal:  J Chem Ecol       Date:  2014-12-20       Impact factor: 2.626

5.  Hydrogen peroxide as a new defensive compound in "benzoyl cyanide" producing polydesmid millipedes.

Authors:  Yasumasa Kuwahara; Takuya Yamaguchi; Yayoi Ichiki; Tsutomu Tanabe; Yasuhisa Asano
Journal:  Naturwissenschaften       Date:  2017-03-01

6.  Oviposition in Delia platura (Diptera, Anthomyiidae): the role of volatile and contact cues of bean.

Authors:  Sandrine P Gouinguené; Erich Städler
Journal:  J Chem Ecol       Date:  2006-05-23       Impact factor: 2.626

7.  Defensive secretions in three species of polydesmids (Diplopoda, Polydesmida, Polydesmidae).

Authors:  Slobodan E Makarov; Bozidar P M Curcić; Vele V Tesević; Milka B Jadranin; Ljubodrag V Vujisić; Srećko B Curcić; Boris M Mandić; Tatjana L Sekulić; Bojan M Mitić
Journal:  J Chem Ecol       Date:  2010-08-31       Impact factor: 2.626

8.  n-Hexyl laurate and fourteen related fatty acid esters: new secretory compounds from the julid millipede, Anaulaciulus sp.

Authors:  Nobuhiro Shimizu; Yasumasa Kuwahara; Ryota Yakumaru; Tsutomu Tanabe
Journal:  J Chem Ecol       Date:  2012-01-18       Impact factor: 2.626

9.  Production of Plant-Associated Volatiles by Select Model and Industrially Important Streptomyces spp.

Authors:  Zhenlong Cheng; Sean McCann; Nicoletta Faraone; Jody-Ann Clarke; E Abbie Hudson; Kevin Cloonan; N Kirk Hillier; Kapil Tahlan
Journal:  Microorganisms       Date:  2020-11-11

10.  Phytohormones and volatile organic compounds, like geosmin, in the ectomycorrhiza of Tricholoma vaccinum and Norway spruce (Picea abies).

Authors:  Oluwatosin Abdulsalam; Katharina Wagner; Sophia Wirth; Maritta Kunert; Anja David; Mario Kallenbach; Wilhelm Boland; Erika Kothe; Katrin Krause
Journal:  Mycorrhiza       Date:  2020-11-18       Impact factor: 3.387

  10 in total

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