The characterization and properties of castaprenol-11, -12 and -13 from the leaves of Aesculus hippocastanum (horse chestnut)

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The characterization and properties of castaprenol-11, -12 and -13 from the leaves of Aesculus hippocastanum (horse chestnut)

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Abstract

The isolation and purification of a mixture of cis–trans-polyprenols from the leaves of Aesculus hippocastanum (horse chestnut) are described. Results of studies involving mass spectrometry, nuclear magnetic resonance, infrared spectroscopy, micro-hydrogenation and ozonolytic degradation show the mixture to be made up of undecaprenol, dodecaprenol and tridecaprenol with dodecaprenol predominating. Each of the prenols contains three trans internal isoprene residues and a cis `OH-terminal' isoprene residue. They differ from each other only in the number of cis internal isoprene residues. The trivial names castaprenol-11, castaprenol-12 and castaprenol-13 are proposed to describe these compounds. Gas–liquid-chromatographic and reversed-phase partition thin-layer chromatographic evidence suggest the presence in the mixture of small quantities of castaprenol-10 also.

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