Preprint Article Version 2 This version is not peer-reviewed

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

Version 1 : Received: 24 March 2018 / Approved: 26 March 2018 / Online: 26 March 2018 (08:37:45 CEST)
Version 2 : Received: 10 May 2018 / Approved: 10 May 2018 / Online: 10 May 2018 (11:51:09 CEST)

How to cite: 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. Preprints 2018, 2018030209 (doi: 10.20944/preprints201803.0209.v2). 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. Preprints 2018, 2018030209 (doi: 10.20944/preprints201803.0209.v2).

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 MS and quantum mechanics calculations (QM), the tridimensional structure was unravelled after isolation and NMR analysis. The absolute configuration was assigned by comparison of experimental and theoretical SRCD 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 IC50 of 9.17 µM.

Subject Areas

Mitracarpus scaber Zucc.; pentalogin; anti-inflammatory; MS/MS; Il-8

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