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Structural elucidation of natural 2‐hydroxy di‐ and tricarboxylic acids and esters, phenylpropanoid esters and a flavonoid from Autonoë madeirensis using gas chromatographic/electron ionization, electrospray ionization and tandem mass spectrometric techniques
Author(s) -
Dias C.,
Dias M.,
Borges C.,
Almoster Ferreira M. A.,
Paulo A.,
Nascimento J.
Publication year - 2003
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.554
Subject(s) - chemistry , phenylpropanoid , electrospray ionization , apigenin , electron ionization , chemical ionization , organic chemistry , tandem mass spectrometry , mass spectrometry , tricarboxylic acid , chromatography , stereochemistry , flavonoid , ionization , citric acid cycle , biosynthesis , enzyme , antioxidant , ion
The chemical composition of Autonoë madeirensis bulbs was characterized as part of a systematic phytochemical study of this species. The compounds reported were mainly identified on the basis of gas chromatography/electron ionization, electrospray ionization and tandem mass spectrometry. The structures of the pure compounds were also characterized by means of other physical and spectroscopic data (m.p., IR, UV, NMR). The compounds identified were 2‐hydroxy di‐ and tricarboxylic acids and esters (malic acid, citric acid and their methyl and ethyl esters), cis ‐ and trans ‐hydroxycinnamic esters (methyl and ethyl p ‐coumarate and methyl ferulate) and a new flavone diglucoside, 7‐ O ‐[β‐glucosyl‐(1→2)‐ O ‐β‐glucosyl]apigenin, the interglucosidic linkage (1→2) of which is, to the best of our knowledge, reported for the first time in a diglucoside of apigenin. The results may contribute to the chemotaxonomy of the Autonoë genus and lead to a rapid tool for the systematic characterization of these compounds in plant extracts. Copyright © 2003 John Wiley & Sons, Ltd.