The characterization and properties of castaprenol-11, -12 and -13 from the leaves of Aesculus hippocastanum (horse chestnut).
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.
D000085:Acetates; D000438:Alcohols / Q000032:analysis*; D002247:Carbon Isotopes; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D066298:In Vitro Techniques; D007259:Infrared Rays; D009682:Magnetic Resonance Spectroscopy; D010126:Ozone; D010946:Plants, Medicinal / Q000032:analysis*; D013053:Spectrophotometry; D013057:Spectrum Analysis; D013729:Terpenes / Q000032:analysis*
D000085:Acetates; D000438:Alcohols; D002247:Carbon Isotopes; D013729:Terpenes; D010126:Ozone