Composition of the Unsaturated Hydrocarbons of the Millipede Graphidostreptus Tumuliporus (Karsch) (Diplopoda: Spirostreptida)

Author： Oudejans R.C.H.M.

Publisher： Brill

ISSN： 1568-542X

Source： Netherlands Journal of Zoology, Vol.23, Iss.3, 1972-01, pp. : 330-342

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Abstract

Upon fractionation on silicagel impregnated with silver nitrate the total hydrocarbons from males and females of the millipede Graphidostreptus tumuliporus (Karsch) were separated into four fractions, viz., on an average 10% alkanes, 38% alk-1-enes, 46% alkadienes and 6% alkatrienes with traces of squalene. The alk-1-enes and also the alkadienes and alkatrienes contain one terminal double bond (vinyl group, - CH=CH₂), while the remaining internal double bonds appear to be of the cis-type. Apart from straight-chain homologues with chain lengths up to 38 carbon atoms several series of homologous branched-chain hydrocarbons are present in all fractions. The complete composition of all fractions is given, based on gas-liquid chromatography and infrared and nuclear magnetic resonance spectrometry. Most of the hydrocarbons isolated from Graphidostreptus possess a structure which is not known from other organisms. Especially the cis-cyclopropane-alk-1-enes with a chain length of 25 to 35 carbon atoms are intriguing, since these structures were present in only the females (15% of the alk-1-enes), suggesting a relationship with the unusual cyclopropane fatty acids that have been isolated from only this sex, too. Except for these cyclopropane hydrocarbons only quantitative differences exist between the hydrocarbon compositions of male and female G. tumuliporus.