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Molecules 2018, 23(5), 1237; https://doi.org/10.3390/molecules23051237

MS/MS-Guided Isolation of Clarinoside, a New Anti-Inflammatory Pentalogin Derivative

1
Laboratoires Clarins, 5 rue Ampère, 95300 Pontoise, France
2
DISCO Beamline, Synchrotron SOLEIL, 91192 Gif-sur-Yvette, France
3
UAR1008, CEPIA, INRA, 44316 Nantes, France
4
C-TAC, UMR 8638 CNRS, Faculté de Pharmacie de Paris, Université Paris Descartes, Sorbonne Paris Cité, 4 Avenue de l’Observatoire, 75006 Paris, France
5
Department of Biochemistry, Hôpital Européen Georges Pompidou, AH-HP, 75015 Paris, France
*
Author to whom correspondence should be addressed.
Received: 30 March 2018 / Revised: 10 May 2018 / Accepted: 19 May 2018 / Published: 22 May 2018
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Abstract

Re-investigation of the chemical composition of the annual plant Mitracarpus scaber Zucc. led to the identification of clarinoside, a new pentalogin derivative containing a rare quinovose moiety, and the known compound harounoside. While the planar structure was fully determined using tandem mass spectrometry (MS) and quantum mechanics (QM) calculations, the tridimensional structure was unravelled after isolation and NMR analysis. The absolute configuration was assigned by comparison of experimental and theoretical synchrotron radiation circular dichroism spectra. Both compounds were tested for anti-inflammatory activity, and compound 1 showed the ability to inhibit the production of interleukin-8 (Il-8) with an IC 50 value of 9.17 μ M. View Full-Text
Keywords: Mitracarpus scaber Zucc.; pentalogin; anti-inflammatory; MS/MS; Il-8 Mitracarpus scaber Zucc.; pentalogin; anti-inflammatory; MS/MS; Il-8
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Audoin, C.; Zampalégré, A.; Blanchet, N.; Giuliani, A.; Roulland, E.; Laprévote, O.; Genta-Jouve, G. MS/MS-Guided Isolation of Clarinoside, a New Anti-Inflammatory Pentalogin Derivative. Molecules 2018, 23, 1237.

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