P1: KEG
joec2004.cls (04/06/2004 v1.1 LaTeX2e JOEC document class) pp1276-joec-490202 September 13, 2004 18:0
Journal of Chemical Ecology, Vol. 30, No. 8, August 2004 (
C
2004)
THE CHEMISTRY OF EXPLODING ANTS, Camponotus SPP.
(cylindricus COMPLEX)
T. H. JONES,
1,∗
D. A. CLARK,
1
A. A. EDWARDS,
2
D. W. DAVIDSON,
3
T. F. SPANDE,
4
and R. R. SNELLING
5
1
Department of Chemistry
Virginia Military Institute
Lexington, Virginia 24450, USA
2
Department of Chemistry
Universiti Brunei Darussalam
Tungku Link, BE 1410, Brunei Darussalam
3
Department of Biology, University of Utah
257 South, 1400 East
Salt Lake City, Utah 84112-0840, USA
4
Laboratory of Bioorganic Chemistry
NIH, NIDDK
Bethesda, Maryland 20892-0820, USA
5
Entomology Division
Natural History Museum of Los Angeles County
900 Exposition Blvd.
Los Angeles 90007, USA
(Received January 15, 2004; accepted April 8, 2004)
Abstract—A detailed comparative analysis of the exocrine chemistry of nine
Bruneian Camponotus species in the cylindricus complex is reported. Workers
of these species are known to have hypertrophied mandibular glands and re-
lease their glandular contents suicidally from the head by rupturing the inter-
segmental membrane of the gaster. All of the species produce mixtures of
polyacetate-derived aromatics, including hydroxyacetophenones, which display
pH-dependent color changes, and aliphatic hydrocarbons and alcohols. In addi-
tion, three species contained (6R)-2,6-dimethyl-(2E)-octen-1,8-dioic acid (9)
or (3S)-8-hydroxycitro-nellic acid (10a), previously unreported from insects.
These compounds were characterized from their spectral data, and confirmed
by comparison with synthetic samples. The allomonal role of these compounds
∗
To whom correspondence should be addressed. E-mail: jonesth@mail.vmi.edu
1479
0098-0331/04/0800-1479/0
C
2004 Plenum Publishing Corporation