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

• Tipo: Artigo em Revista Científica Internacional
• Data: 2011

Autores

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

Revista

Título: Rapid Communications in Mass Spectrometry

Vol. 25 Nº 6

Páginas: 700-712

ISSN: 0951-4198

Editora: Wiley-Blackwell

Indexação

ISI Web of Knowledge - 27 Citações

ISI Web of Science

Scopus - 41 Citações

Pubmed / Medline

Classificação Científica

FOS: Ciências exactas e naturais > Química

CORDIS: Ciências da Saúde > Ciências farmacológicas > Farmacognosia

Outras Informações

ID Authenticus: 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.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 13