Literature DB >> 1124395

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

J Smolanoff, A F Kluge, J Meinwald, A McPhail, R W Miller, K Hicks, T Eisner.   

Abstract

A nitrogen-containing terpene 6,6-dimethyl-2-azaspiro[4.4]non-1-ene (polyzonimine) was isolated from the defensive secretion of the milliped Polyzonium rosalbum. Polyzonimine, which is repellent to such natural enemies of the milliped as ants, acts as a topical irritant to insects (10-4 M induces scratching in cockroaches). Its structure was confirmed by a five-step synthesis starting from 2,2-dimethyl-7-oxabicyclo[4.1.0]heptane.

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Year:  1975        PMID： 1124395     DOI： 10.1126/science.1124395

Source DB:  PubMed          Journal:  Science        ISSN： 0036-8075            Impact factor:   47.728


  8 in total

1.  Convergent evolution of chemical defense in poison frogs and arthropod prey between Madagascar and the Neotropics.

Authors:  Valerie C Clark; Christopher J Raxworthy; Valérie Rakotomalala; Petra Sierwald; Brian L Fisher
Journal:  Proc Natl Acad Sci U S A       Date:  2005-08-08       Impact factor: 11.205

2.  Bioactive alkaloids of frog skin: combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source.

Authors:  John W Daly; Tetsuo Kaneko; Jason Wilham; H Martin Garraffo; Thomas F Spande; Alex Espinosa; Maureen A Donnelly
Journal:  Proc Natl Acad Sci U S A       Date:  2002-10-14       Impact factor: 11.205

3.  Contact toxicities of anuran skin alkaloids against the fire ant (Solenopsis invicta).

Authors:  Paul J Weldon; Yasmin J Cardoza; Robert K Vander Meer; W Clint Hoffmann; John W Daly; Thomas F Spande
Journal:  Naturwissenschaften       Date:  2013-01-23

Review 4.  The chemistry of phyletic dominance.

Authors:  J Meinwald; T Eisner
Journal:  Proc Natl Acad Sci U S A       Date:  1995-01-03       Impact factor: 11.205

5.  1-Octen-3-ol together with geosmin: new secretion compounds from a polydesmid millipede, Niponia nodulosa.

Authors:  Hisashi Omura; Yasumasa Kuwahara; Tsutomu Tanabe
Journal:  J Chem Ecol       Date:  2002-12       Impact factor: 2.626

6.  Necrodols: Anti-insectan terpenes from defensive secretion of carrion beetle (Necrodes surinamensis).

Authors:  T Eisner; M Deyrup; R Jacobs; J Meinwald
Journal:  J Chem Ecol       Date:  1986-06       Impact factor: 2.626

7.  Characterization and synthesis of volatile compounds from the defensive secretions of some "daddy longlets" (Arachnida: Opiliones: Leiobunum spp.).

Authors:  T H Jones; J Meinwald; K Hicks; T Eisner
Journal:  Proc Natl Acad Sci U S A       Date:  1977-02       Impact factor: 11.205

8.  Pygidial secretions ofPasimachus subsulcatus (Coleoptera: Carabidae) deter predation byEumeces inexpectatus (Squamata: Scincidae).

Authors:  B W Witz; H R Mushinsky
Journal:  J Chem Ecol       Date:  1989-03       Impact factor: 2.626
  8 in total

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