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Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

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Lipids

Abstract

Novel ceramides, rel-(3S,4S,5S)-3-[(2R)-2-hydroxycosanoyl-hexacosanoylamino]-4-hydroxy-5-[(4Z)-tetradecane-4-ene]-2,3,4,5-tetrahydrofuran (1a-g), and a new glucoceramide, 1-O-β-d-glucopyranosyl-(2S,3S,4R,8E)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-octodecanetriol-8-ene (2) were isolated from the aqueous ethanolic extract of the roots of Incarvillea arguta, together with eight known compounds: β-sitosterol (3), oleanolic acid (4), ursolic acid (5), piperin (6), maslinic acid (7), β-sitosterol 6′-O-acyl-β-d-glucopyranoside (8), 8-epideoxyloganic acid (9), and plantarenaloside (10). Their structures were elucidated on the basis of spectral data including IR, MS, NMR [1H NMR, 13C NMR (distortionless enhancement by polarization transfer), 1H−1H COSY, heteronuclear multiplequantum coherence, and heteronuclear multiple-bond coherence correlations]. The relative configurations were established by nuclear Overhauser effect spectroscopy experiments and by comparison of the NMR spectral data and coupling constants with those already reported in the literature.

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Abbreviations

CC:

column chromatography

DEPT:

distortionless enhancement by polarization transfer

Fr:

fraction

Gly:

glucosyl

HMBC:

(1H-detected) heteronuclear multiple-bond correlation

HMOC:

(1H-detected) heteronuclear multiple-quantum coherence

HRAPCIMS:

high-resolution atmospheric pressure chemical ionization mass spectrum

NOESY:

nuclear Overhauser effect spectroscopy

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Authors and Affiliations

  1. Sichuan Institute of Chinese Materia Medica, 610041, Chengdu, People's Republic of China

    Jinhai Yi

  2. Chengdu Institute of Biology, Chinese Academy of Sciences, P.O. Box 416, 610041, Chengdu, P.R. China

    Yinggang Luo, Jinhai Yi, Bogang Li & Guolin Zhang

Authors
  1. Yinggang Luo
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  2. Jinhai Yi
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  3. Bogang Li
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  4. Guolin Zhang
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Correspondence to Guolin Zhang.

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Luo, Y., Yi, J., Li, B. et al. Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta . Lipids 39, 907–913 (2004). https://doi.org/10.1007/s11745-004-1313-4

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  • DOI: https://doi.org/10.1007/s11745-004-1313-4

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