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Natural wax constituents of a supercritical fluid CO2 extract from quince (Cydonia oblonga Mill.) pomace

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Abstract

The chemical constituents of a lipophilic extract from quince (Cydonia oblonga Mill.), obtained by supercritical fluid CO2 extraction of the dried fruit pomace were investigated. Solvent partition of quince wax with n-hexane or acetone yielded an insoluble (crystalline) and a soluble (oily) fraction. Both fractions were analyzed separately using gas chromatography/mass spectrometry (GC/MS). The insoluble fraction consisted of saturated n-aldehydes, n-alcohols and free n-alkanoic acids of carbon chain lengths between 22 and 32, with carbon chain lengths of 26 and 28 dominating. Also odd-numbered unbranched hydrocarbons, mainly C27, C29 and C31, were detected particularly in the acetone-insoluble fraction (total, 15.8%). By means of vacuum liquid chromatography, triterpenoic acids were separated from the hexane-insoluble matter and identified as a mixture of ursolic, oleanolic and betulinic acids. The major constituents of the hexane-soluble fraction were glycerides of linoleic [Δ9,12, 18:2] and oleic [Δ9, 18:1] acids, accompanied by free linoleic, oleic and palmitic acids (C16). Moreover β-sitosterol, Δ5-avenasterol as well as trace amounts of other sterols were assigned. Finally the carotenoids phytoene and phytofluene were identified and quantified by UV/vis and high-performance liquid chromatography/MS techniques, yielding 1.0 and 0.3% of the quince wax, respectively. It is anticipated that the complex of lipid constituents from quince wax may exert interesting biological activities, the elucidation of which awaits further studies.

Quince fruits and some of their fruit wax constituents. Clockwise (starting at one o’clock): structure formulas of Δ5-avenasterol, linoleic acid, oleanolic acid, and phytofluen.

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Abbreviations

APCI:

atmospheric pressure chemical ionization

GC:

gas chromatography

HPLC:

high-performance liquid chromatography

LC:

liquid chromatography

MS:

mass spectrometry

PCC:

pyridinium chlorochromate

TIC:

total ion chromatogram

TLC:

thin-layer chromatography

TMSi:

trimethylsilyl

VLC:

vacuum liquid chromatography

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Acknowledgements

The authors wish to thank Jürgen Conrad (Department of Chemistry, Hohenheim University, Stuttgart, Germany) for recording the NMR spectra, Bernhard Weigl (BASF, Ludwigshafen, Germany) for a sample of synthetic phytoene and Zohar Nir (LycoRed Ltd., Israel) for providing a sample of a phytoene/phytofluene mixture.

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Authors and Affiliations

  1. WALA Heilmittel GmbH, Dorfstrasse 3, 73087, Bad Boll/Eckwälden, Germany

    Peter Lorenz, Melanie Berger, Julia Bertrams, Ulrich Meyer & Florian C. Stintzing

  2. Institute of Pharmacy, Ernst-Moritz-Arndt-University, Friedrich-Ludwig-Jahn-Str. 17, 17487, Greifswald, Germany

    Kristian Wende, Kristin Wenzel & Ulrike Lindequist

Authors
  1. Peter Lorenz
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  2. Melanie Berger
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  3. Julia Bertrams
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  4. Kristian Wende
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  5. Kristin Wenzel
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  6. Ulrike Lindequist
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  7. Ulrich Meyer
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  8. Florian C. Stintzing
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Correspondence to Florian C. Stintzing.

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Lorenz, P., Berger, M., Bertrams, J. et al. Natural wax constituents of a supercritical fluid CO2 extract from quince (Cydonia oblonga Mill.) pomace. Anal Bioanal Chem 391, 633–646 (2008). https://doi.org/10.1007/s00216-008-2000-5

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  • DOI: https://doi.org/10.1007/s00216-008-2000-5

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