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

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

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MDPI and ACS Style

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. https://doi.org/10.3390/molecules23051237

AMA Style

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(5):1237. https://doi.org/10.3390/molecules23051237

Chicago/Turabian Style

Audoin, Coralie, Adam Zampalégré, Natacha Blanchet, Alexandre Giuliani, Emmanuel Roulland, Olivier Laprévote, and Grégory Genta-Jouve. 2018. "MS/MS-Guided Isolation of Clarinoside, a New Anti-Inflammatory Pentalogin Derivative" Molecules 23, no. 5: 1237. https://doi.org/10.3390/molecules23051237

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