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New Nortriterpenoid and Ceramides From Stems and Leaves of Cultivated Triumfetta cordifolia A Rich (Tiliaceae)

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Journal of the American Oil Chemists' Society

Abstract

To highlight the role of plants in traditional healing, the leaves and the stems of cultivated Triumfetta cordifolia were phytochemically studied yielding a new nor-ursane type (1), a new ceramide (2) and a new piperidinic ceramide derivative (3) named, respectively, 2α,19α-dihydroxy-3-oxo-23-nor-urs-12-en-28-oic acid, (2R)-2-hydroxy-N-[(2S,3S,4R,26E)-1,3,4-trihydroxy-26-triaconten-2-yl] tetradecanamide and (2R,8Z)-2-hydroxy-{(2S,3R,5R,6S)-3,5-dihydroxy-6-[(1E,5Z)-hexadeca-1,5-dienyl]-2-(β-d-glucopyranosyloxy)methyl piperidine-1-yl} tetracos-8-enamide (3). These were obtained together with lupeol (4), stigmasterol (5), 3-O-β-d-glucopyranoside of β-sitosterol (6), tormentic acid (7) from stems and heptadecanoic acid (8), β-carotene (9), oleanolic acid (10), and 24-hydroxytormentic acid (11) from leaves. The structures were determined on the basis of NMR data (1H-, 13C-, 2D-NMR analyses), mass spectrometry and confirmed by chemical transformations as well as comparison of spectral data with those reported in the literature. The FRAP method was used to evaluate the antioxidant activity of fractions collected from flash chromatography and isolated compounds. Among the fractions, four reduced FeIII-TPTZ to FeII-TPTZ while isolated pure compounds showed no activity.

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Abbreviations

APT:

Attached proton test

CC:

Column chromatography

COSY:

Correlation spectroscopy

FRAP:

Ferric reducing ability of plasma

FT-IR:

Fourier transformed infra-red

HMBC:

Heteronuclear multiple bond correlation

HSQC:

Heteronuclear single quantum correlation

HR-ESI-MS:

Higher resolution electrospray mass spectrometry

LCB:

Long chain base

MALDI-TOF-MS:

Matrix assisted laser desorption ionisation-time of flight-mass spectrometry

NMR:

Nuclear magnetic resonance

NOESY:

Nuclear overhauser effect spectroscopy

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Acknowledgments

L. P. Sandjo would like to thank EGIDE and SCAC (Service de Cooperation et d’Actions Culturelles: French Grant Government No. 607832K) for their financial support. I would also like to thank the LSMCL (Laboratoire de Spectrométrie de Masse et Chimie Laser) for the MALDI-TOF-MS analyses and Serge Schneider for the LC-MS analyses.

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Authors and Affiliations

  1. Department of Organic Chemistry, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon

    Louis Pergaud Sandjo, Abdou Tchoukoua, Felix Keumedjio & Bonaventure Tchaleu Ngadjui

  2. Laboratoire d’Ingénierie Moléculaire et Biochimie Pharmacologique, Institut Jean Barriol, University of Paul-Verlaine Metz, 1Bld Arago, 57070, Metz, France

    Louis Pergaud Sandjo, Enrico Perspicace & Gilbert Kirsch

  3. National Advanced School of Engineering, University of Yaoundé I, P.O. Box 8390, Yaoundé, Cameroon

    Hippolyte Nga Ntede

  4. Laboratoire de Méthodologie RMN, Institut Jean Barriol, Faculty of Science, University Henri Poincaré, P.O. Box 239, 54506, Vandoeuvre-les-Nancy Cedex, France

    Mehdi Yemloul

  5. Institut Lavoisier de Versailles UMR 8086 University of Versailles-St-Quentin-en-Yvelines, 45 Av. des Etats-Unis, 78035, Versailles Cedex, France

    François Couty

Authors
  1. Louis Pergaud Sandjo
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  2. Abdou Tchoukoua
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  3. Hippolyte Nga Ntede
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  4. Mehdi Yemloul
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  8. Gilbert Kirsch
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  9. Bonaventure Tchaleu Ngadjui
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Correspondence to Louis Pergaud Sandjo or Bonaventure Tchaleu Ngadjui.

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Sandjo, L.P., Tchoukoua, A., Ntede, H.N. et al. New Nortriterpenoid and Ceramides From Stems and Leaves of Cultivated Triumfetta cordifolia A Rich (Tiliaceae). J Am Oil Chem Soc 87, 1167–1177 (2010). https://doi.org/10.1007/s11746-010-1584-z

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  • DOI: https://doi.org/10.1007/s11746-010-1584-z

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