Structural elucidation of natural 2-hydroxy di- and tricarboxylic acids and esters, phenylpropanoid esters and a flavonoid from Autonoe madeirensis using gas chromatographic/electron ionization, electrospray ionization and tandem mass spectrometric techniques

• Author(s): Dias, C ; Dias, M ; Borges, C ; Ferreira, MAA ; Paulo, A ; Nascimento, J
• Date: 2003
• Persistent ID: http://hdl.handle.net/10451/20867
• Origin: Repositório da Universidade de Lisboa
• Subject(s): Biophysics; Chemistry, Organic; Spectroscopy
• Document Type: Journal article
• Language: English
• Contributor(s): Repositório Científico de Acesso Aberto da ULisboa

Description

The chemical composition of Autonoe 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-[beta-glucosyl-(1--2)-O-beta-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 Autonoe genus and lead to a rapid tool for the systematic characterization of these compounds in plant extracts. Copyright (C) 2003 John Wiley Sons, Ltd.