title: Structure elucidation of chlorophyll catabolites (phyllobilins) by ESI-mass spectrometry-Pseudo-molecular ions and fragmentation analysis of a nonfluorescent chlorophyll catabolite (NCC).
abstract: The hyphenation of high performance chromatography with modern mass spectrometric techniques providing high-resolution data as well as structural information from MS/MS experiments has become a versatile tool for rapid natural product identification and characterization. A recent application of this methodology concerned the investigation of the annually occurring degradation of green plant pigments. Since the first structural elucidation of a breakdown product in the early 1990s, a number of similarly structured, tetrapyrrolic catabolites have been discovered with the help of chromatographic, spectroscopic and spectrometric methods. A prerequisite for a satisfactory, manually operated or database supported analysis of mass spectrometric fragmentation patterns is a deeper knowledge of the underlying gas phase chemistry. Still, a thorough investigation of the common fragmentation behavior of these ubiquitous, naturally occurring chlorophyll breakdown products is lacking. This study closes the gap and gives a comprehensive overview of collision-induced fragmentation reactions of a tetrapyrrolic nonfluorescent chlorophyll catabolite, which is intended to serve as a model compound for the substance class of phyllobilins.
authors.affiliation: Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, 6020 Innsbruck, Austria.
authors.forename: Thomas
authors.initials: T
authors.lastname: Müller
authors.affiliation: Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, 6020 Innsbruck, Austria.
authors.forename: Stefan
authors.initials: S
authors.lastname: Vergeiner
authors.affiliation: Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, 6020 Innsbruck, Austria.
authors.forename: Bernhard
authors.initials: B
authors.lastname: Kräutler
keywords: Catabolomics; Chlorophyll; Collision-induced dissociation; Ionic fragmentation; Phyllobilin; Structure elucidation
references.citation: Plant Physiol. 2005 Sep;139(1):52-63
references.pmid: 16113212
references.citation: Rapid Commun Mass Spectrom. 1992 Feb;6(2):105-8
references.pmid: 1504338
references.citation: European J Org Chem. 2009 Jan;2009(1):21-31
references.pmid: 21037946
references.citation: Chembiochem. 2006 Jan;7(1):40-2
references.pmid: 16292786
references.citation: J Biol Chem. 1998 Jun 19;273(25):15335-9
references.pmid: 9624113
references.citation: Biochim Biophys Acta. 2011 Aug;1807(8):977-88
references.pmid: 21167811
references.citation: Anal Chem. 2011 Jul 15;83(14):5754-61
references.pmid: 21675752
references.citation: Biomed Mass Spectrom. 1982 May;9(5):208-14
references.pmid: 7093442
references.citation: Angew Chem Int Ed Engl. 2008;47(46):8954-7
references.pmid: 18850621
references.citation: Chemistry. 2011 Feb 18;17(8):2330-4
references.pmid: 21308817
references.citation: Proc Natl Acad Sci U S A. 2003 Jun 10;100(12):6910-5
references.pmid: 12777622
references.citation: Angew Chem Int Ed Engl. 2007;46(45):8699-702
references.pmid: 17943948
references.citation: Anal Chem. 1988 Oct 15;60(20):2299-301
references.pmid: 3239801
references.citation: Plant Physiol. 2012 Feb;158(2):628-41
references.pmid: 22147518
references.citation: Anal Chem. 2010 Jun 1;82(11):4648-51
references.pmid: 20465224
references.citation: Science. 1989 Oct 6;246(4926):64-71
references.pmid: 2675315