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

Coralie Audoin, Adam Zampalégré, Natacha Blanchet, Alexandre Giuliani, Emmanuel Roulland, Olivier Laprévote, Grégory Genta-Jouve
2018 Molecules  
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
more » ... ntal 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 µM.
doi:10.3390/molecules23051237 pmid:29789477 fatcat:7oyqvj7fdbdnhij2ldufhzdvtq