Approach to the study of C-glycosyl flavones acylated with aliphatic and aromatic acids from Spergularia rubra by high-performance liquid chromatography-photodiode array detection/electrospray ionization multi-stage mass spectrometry

• Type: Article in International Scientific Journal
• Date: 2011

Authors

Federico Ferreres (Author) Other; Angel Gil Izquierdo (Author) Other; Juliana Vinholes (Author) Other; Clara Grosso (Author) Other; Patricia Valentao (Author) FFUP; Paula B Andrade (Author) FFUP

Journal

Title: Rapid Communications in Mass Spectrometry

Vol. 25 No. 6

Pages: 700-712

ISSN: 0951-4198

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 27 Citations

ISI Web of Science

Scopus - 41 Citations

Pubmed / Medline

Scientific classification

FOS: Natural sciences > Chemical sciences

CORDIS: Health sciences > Pharmacological sciences > Pharmacognosy

Other information

Authenticus ID: P-002-T58

DOI: 10.1002/rcm.4910

Resumo (PT): The use of mass spectrometry (MS) coupled to liquid chromatography (LC) as working tool for the study of the C-glycosyl flavones acylated with aliphatic and aromatic acids has allowed the tentative characterization of these compounds in Spergularia rubra and the establishment of the position of the acylation on the sugar moiety of the C-glycosylation by use of MS data. The combination of retention time (Rt), ultraviolet (UV) and MSn data of the compounds revealed their C-glycosyl flavone nature, being luteolin, apigenin and chrysoeriol derivatives. Ten non-acylated flavones were identified, from which six are described for the first time (one 7-O-glycosyl-6,8-diC-glycosyl flavone, four 6,8-diC-glycosyl flavones and one 2”-O-glycosyl-6-C-glycosyl flavone). Twenty-six acylated derivatives were also found for the first time. These compounds are grouped in three classes, namely, C-glycosyl flavones acylated with aliphatic acids, with aromatic acids or with a mixed acylation. The first group is characterized by the presence of one 6,8-diC-(acetyl)glycosyl flavone, four 6,8-diC-(malonyl)glycosyl flavones and two 7-O-glycosyl-6,8-diC-(malonyl)glycosyl flavones, while in the second one twelve 6,8-diC-(acyl)glycosyl flavones and two 7-O-glycosyl-6,8-diC-(acyl)glycosyl flavones are described. The last class contained five 6,8-diC-(malonyl,acyl)glycosyl flavones. No previous work has described the presence of C-glycosyl flavones acylated with aliphatic acids in this genus <br> <br> <a target="_blank" href="http://onlinelibrary.wiley.com/doi/10.1002/rcm.4910/abstract">Texto integral </a> <br> <br>

Abstract (EN): The use of mass spectrometry (MS) coupled to liquid chromatography (LC) as working tool for the study of the C-glycosyl flavones acylated with aliphatic and aromatic acids has allowed the tentative characterization of these compounds in Spergularia rubra and the establishment of the position of the acylation on the sugar moiety of the C-glycosylation by use of MS data. The combination of retention time (Rt), ultraviolet (UV) and MS(n) data of the compounds revealed their C-glycosyl flavone nature, being luteolin, apigenin and chrysoeriol derivatives. Ten non-acylated flavones were identified, from which six are described for the first time (one 7-O-glycosyl-6, 8-diC-glycosyl flavone, four 6,8-diC-glycosyl flavones and one 2 ''-O-glycosyl-6-C-glycosyl flavone). Twenty-six acylated derivatives were also found for the first time. These compounds are grouped in three classes, namely, C-glycosyl flavones acylated with aliphatic acids, with aromatic acids or with a mixed acylation. The first group is characterized by the presence of one 6,8-diC-(acetyl) glycosyl flavone, four 6,8-diC-(malonyl) glycosyl flavones and two 7-O-glycosyl-6,8-diC-(malonyl) glycosyl flavones, while in the second one twelve 6,8-diC-(acyl) glycosyl flavones and two 7-O-glycosyl-6,8-diC-(acyl) glycosyl flavones are described. The last class contained five 6,8-diC-(malonyl, acyl) glycosyl flavones. No previous work has described the presence of C-glycosyl flavones acylated with aliphatic acids in this genus. Copyright (C) 2011 John Wiley & Sons, Ltd.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 13