ChemInform Abstract: The Development of Strategies for Terpenoid Structure Determination

School of Chemistry, Physics and Environmental Science, University of Sussex, Brighton, UK.
Natural Product Reports (Impact Factor: 10.72). 04/2002; 18(6):607-17. DOI: 10.1039/B103772M
Source: PubMed

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    ABSTRACT: Sixteen terpene compounds were isolated from the soldier defensive secretions of seven European termite taxa of the genus Reticulitermes (Isoptera, Rhinotermitidae). We describe species-specific mixtures of monoterpenes (alpha-pinene, beta-pinene, limonene), sesquiterpenes (germacrene C, germacrene A, germacrene B, beta-selinene, delta-selinene, gamma-selinene, (E)-beta-farnesene, gamma-cadinene, nerolidol), diterpenes (geranyl linalool, geranyl geraniol, geranyl geranial), and one sesterterpene (geranyl farnesol). Compounds were purified by HPLC and their structures determined by means of MS spectrometry, or 1D and 2D NMR spectroscopy. Comparison of two different analytical approaches, CC-MS and HPLC with subsequent NMR spectroscopy, revealed Cope rearrangement of germacrene A, germacrene B, and germacrene C to the respective beta-elemene, gamma-elemene, and delta-elemene under GC conditions, thus demonstrating the limits for this analytical approach. The species-specific compound composition provides insight into taxonomy and species origin of European Reticulitermes. The biological significance of the species-specific composition of Reticulitermes defensive secretions is briefly discussed.
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