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

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 do-decaprenol 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.