Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Australian Journal of Chemistry Année : 2017

Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis

Résumé

Dactylospongia metachromia and Dactylospongia elegans collected from French Polynesia were studied with a particular focus on the variation of the diastereomeric ratio between ilimaquinone (4) and 5-epi-ilimaquinone (5). More than 100 samples, covering an area of 4100km(2), were studied to try to clarify this intriguing issue. Nuclear magnetic resonance appeared as the non-destructive, straightforward technique of choice for a relative quantitative study. A random distribution, unique at that point in nature, is observed and leads to biosynthetic considerations. Biological evaluation of both compounds was also performed and showed moderate discrepancies in cytotoxicity and apoptosis induction.
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Dates et versions

hal-01483154 , version 1 (04-03-2017)

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Asmaa Boufridi, David Lachkar, Dirk Erpenbeck, Mehdi A. Beniddir, Laurent Evanno, et al.. Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis. Australian Journal of Chemistry, 2017, 70 (6), pp.743-750. ⟨10.1071/CH16455⟩. ⟨hal-01483154⟩
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