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Furanocembranoid Diterpenes as Defensive Compounds in the Dufour Gland of the Ant Crematogaster brevispinosa rochai

Leclercq, Sabine ; de Biseau, Jean-Cristophe ; Braekman, Jean-Claude ; Daloze, Désiré ; Quinet, Yves ; Luhmer, Michel ; Sundin, Anders LU and Pasteels, Jacques M. (2000) In Tetrahedron 56(14). p.2037-2042
Abstract
Two new furanocembranoid diterpenes, crematofuran [(1R∗,11R∗,12R∗)-6,19:11,12-bisepoxycembra-3,6,8(19),15-tetraene] (1) and isocrematofuran [(1R∗,3S∗,4S∗)-3,4:6,19-bisepoxycembra-6,8(19),11,15-tetraene] (2), have been isolated from the Dufour gland secretion of the Brazilian ant Crematogaster brevispinosa rochai. Their structures, including the relative configuration, have been determined by a combination of NMR and molecular mechanics methods. The toxicity of 1 towards other ants is on the same level as that of nicotine. This is the first report of cembranoid... (More)
Two new furanocembranoid diterpenes, crematofuran [(1R∗,11R∗,12R∗)-6,19:11,12-bisepoxycembra-3,6,8(19),15-tetraene] (1) and isocrematofuran [(1R∗,3S∗,4S∗)-3,4:6,19-bisepoxycembra-6,8(19),11,15-tetraene] (2), have been isolated from the Dufour gland secretion of the Brazilian ant Crematogaster brevispinosa rochai. Their structures, including the relative configuration, have been determined by a combination of NMR and molecular mechanics methods. The toxicity of 1 towards other ants is on the same level as that of nicotine. This is the first report of cembranoid diterpenes as defensive compounds in an ant. (Less)
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron
volume
56
issue
14
pages
6 pages
publisher
Elsevier
external identifiers
  • scopus:0034737721
ISSN
0040-4020
DOI
10.1016/S0040-4020(00)00113-7
language
English
LU publication?
yes
id
5ac47474-1c4e-4c90-af63-2207d06f53b0
date added to LUP
2022-05-16 17:45:58
date last changed
2022-05-18 13:05:58
@article{5ac47474-1c4e-4c90-af63-2207d06f53b0,
  abstract     = {{Two new furanocembranoid diterpenes, crematofuran [(1<em>R</em><sup>∗</sup>,11<em>R</em><sup>∗</sup>,12<em>R</em><sup>∗</sup>)-6,19:11,12-bisepoxycembra-3,6,8(19),15-tetraene] (<strong>1</strong>) and isocrematofuran [(1<em>R</em><sup>∗</sup>,3<em>S</em><sup>∗</sup>,4<em>S</em><sup>∗</sup>)-3,4:6,19-bisepoxycembra-6,8(19),11,15-tetraene] (<strong>2</strong>), have been isolated from the Dufour gland secretion of the Brazilian ant <em>Crematogaster brevispinosa rochai.</em> Their structures, including the relative configuration, have been determined by a combination of NMR and molecular mechanics methods. The toxicity of <strong>1</strong> towards other ants is on the same level as that of nicotine. This is the first report of cembranoid diterpenes as defensive compounds in an ant.}},
  author       = {{Leclercq, Sabine and de Biseau, Jean-Cristophe and Braekman, Jean-Claude and Daloze, Désiré and Quinet, Yves and Luhmer, Michel and Sundin, Anders and Pasteels, Jacques M.}},
  issn         = {{0040-4020}},
  language     = {{eng}},
  number       = {{14}},
  pages        = {{2037--2042}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron}},
  title        = {{Furanocembranoid Diterpenes as Defensive Compounds in the Dufour Gland of the Ant <i>Crematogaster brevispinosa rochai</i>}},
  url          = {{http://dx.doi.org/10.1016/S0040-4020(00)00113-7}},
  doi          = {{10.1016/S0040-4020(00)00113-7}},
  volume       = {{56}},
  year         = {{2000}},
}