Ingol - a new macrocyclic diterpene alcohol from euphorbia ingens

Tetrahedron Letters
1973.0

Abstract

The acetone soluble compounds of the latex of Euphorbia ingens can be separated by combination of adsorption chromatography and Craig-distribution. Besides irritant and tumor promoting derivatives of the diterpene ingenol, an additional compound 1 has been isolated, which is the 3,7,12-triacetate-8-nicotinate of a new polyfunctional diterpene ingol 2. Structural elucidation via spectral analysis (high resolution mass spectrometry, NMR, 13C NMR, IR, UV) and chemical reactions (transesterification, acetylation, reduction, oxidation) revealed that ingol 2 exhibits the same tricyclic carbon skeleton as lathyrole and its derivatives, and berthyadionol, and may be biogenetically formed from geranylgeranyl-pyrophosphate via casbene. In the mouse ear assay system, neither compound 1 nor any other derivative of ingol 2 shows irritant activity in doses up to 100 μM/ear. A chromatographically uniform mixture of further tetraesters of ingol 2 was isolated from non-irritant fractions, and their molecular formulae were identified by mass spectrometric analysis.

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