Chemistry and Physics of Lipids 2007-06-01

Alloprenols: novel alpha-trans-polyprenols of Allophylus caudatus.

Ewa Ciepichal, Jacek Wojcik, Tomasz Bienkowski, Magdalena Kania, Malgorzata Swist, Witold Danikiewicz, Andrzej Marczewski, Jozefina Hertel, Zdzislaw Matysiak, Ewa Swiezewska, Tadeusz Chojnacki

Index: Chem. Phys. Lipids 147(2) , 103-12, (2007)

Full Text: HTML

Abstract

A novel type of polyprenols, alloprenols, with an alpha-trans-isoprenoid unit was found in the leaves of Allophylus caudatus (Sapindaceae) besides typical alpha-cis-polyprenols. The polyprenol family (Prenol-11-13, Prenol-12 dominating) was accompanied by traces of dolichols of the same chain-length. Prenol alpha-cis- and alpha-trans-isomers were chromatographically separated and their structure was analyzed by HPLC/ESI-MS, HR-ESI-MS and 1H and 13C NMR spectroscopy. Model compounds, semi-synthetic alpha-isomers of all-trans-Pren-9 and mainly-cis-Pren-11, were obtained using an oxidation-reduction procedure. Comparison of their NMR spectra confirmed the structure of the newly identified polyprenols. The observed pattern of NMR signal shifts may be applied for elucidation of isoprenoid structure.

Related Compounds

  • 3-Methyl-2-buten-1...

Related Articles:

Rapid high performance liquid chromatography-high resolution mass spectrometry methodology for multiple prenol lipids analysis in zebrafish embryos.

2015-09-18

[J. Chromatogr. A. 1412 , 59-66, (2015)]

Fumigant toxicity and acetylcholinesterase inhibitory activity of 4 Asteraceae plant essential oils and their constituents against Japanese termite (Reticulitermes speratus Kolbe).

2014-07-01

[Pestic. Biochem. Physiol. 113 , 55-61, (2014)]

A strategy for position-selective epoxidation of polyprenols.

2008-06-25

[J. Am. Chem. Soc. 130(25) , 8089-93, (2008)]

Heteromeric geranyl diphosphate synthase from mint: construction of a functional fusion protein and inhibition by bisphosphonate substrate analogs.

2004-02-01

[Arch. Biochem. Biophys. 422(1) , 52-60, (2004)]

Antibacterial/antifungal activity and synergistic interactions between polyprenols and other lipids isolated from Ginkgo biloba L. leaves.

2013-01-01

[Molecules 18(2) , 2166-82, (2013)]

More Articles...