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. 2014 May 30;4(2):421-32.
doi: 10.3390/metabo4020421.

Metabolome consistency: additional parazoanthines from the mediterranean zoanthid parazoanthus axinellae

Coralie Audoin  1 , Vincent Cocandeau  2 , Olivier P Thomas  3 , Adrien Bruschini  4 , Serge Holderith  5 , Grégory Genta-Jouve  6
Affiliations

Metabolome consistency: additional parazoanthines from the mediterranean zoanthid parazoanthus axinellae

Coralie Audoin et al. Metabolites. .

Abstract

Ultra-high pressure liquid chromatography coupled to high resolution mass spectrometry (UHPLC-MS/MS) analysis of the organic extract obtained from the Mediterranean zoanthid Parazoanthus axinellae yielded to the identification of five new parazoanthines F-J. The structures were fully determined by comparison of fragmentation patterns with those of previously isolated parazoathines and MS/MS spectra simulation of in silico predicted compounds according to the metabolome consistency. The absolute configuration of the new compounds has been assigned using on-line electronic circular dichroism (UHPLC-ECD). We thus demonstrated the potential of highly sensitive hyphenated techniques to characterize the structures of a whole family of natural products within the metabolome of a marine species. Minor compounds can be characterized using these techniques thus avoiding long isolation processes that may alter the structure of the natural products. These results are also of interest to identify putative bioactive compounds present at low concentration in a complex mixture.

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Figures

Figure 1
Figure 1
Proposed work-flow for the identification of new compounds.
Figure 2
Figure 2
Extracted ions chromatograms (EIC) of the five known parazoanthines: (a) parazoanthine A, (b) parazoanthine B, (c) parazoanthine C, (d) parazoanthine D, (e) parazoanthine E.
Figure 3
Figure 3
Fragmentation pattern of the parazoanthine A using a 20 V collision energy on the pseudo-molecular ion at m/z 318.1558.
Figure 4
Figure 4
Comparison between simulated and experimental MS/MS spectra.
Figure 5
Figure 5
Relative isotopic abundance (RIA) of mono- and di-brominated compounds 4 (left) and 9 (right).
Figure 6
Figure 6
Comparison of simulated and experimental MS/MS spectra of parazoanthine I (9).
Figure 7
Figure 7
BPC (a), UV (b) and ECD (c) profiles of the crude extract of Parazoanthus axinellae.
See this image and copyright information in PMC

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