Structural elucidation of natural 2-hydroxy di- and tricarboxilic acids and esters, phenylpropanoid esters, and flavonoids extracted from the bulbs of Autonoë madeirensis using GC-EIMS, ESIMS and MS/MS techniques

• Author(s): Dias, Catarina ; Dias, Mário ; Borges, Carlos ; Ferreira, M. A. Almoster ; Paulo, Alexandra ; Nascimento, José
• Date: 2003
• Persistent ID: http://hdl.handle.net/10451/9030
• Origin: Repositório da Universidade de Lisboa
• Document Type: Conference object
• Language: English
• Contributor(s): Repositório da Universidade de Lisboa

Description

Comunicação oral sob a forma de Poster

Autonoë madeirensis (Menezes) Speta is a Hyacinthaceae endemic from the Portuguese Archipelago of Madeira.1,2 Previous studies on Hyacinthaceae species have shown that they produce a large number of biologically important secondary metabolites, such as triterpenoid and steroid glycosides3, flavone and homoisoflavanone glycosides4 and polyhydroxyalkaloids.5 Included in a systematic phytochemical study of the bulbs of A. madeirensis, we report now the structural identification of three different classes of compounds, mainly by GC-EIMS, ESIMS and tandem mass spectrometry. The phytochemical study was performed using total ethanolic extracts that were fractionated by solvents of increasing polarity. The compounds identified were 2-hydroxy di- and tricarboxilic acids and esters (malic acid, ethylmethylmalate, diethylmalate, citric acid, monomethylcitrate, monoethylcitrate and triethylcitrate), hydroxycinnamic esters (methyl p-coumarate, ethyl p-coumarate, and methyl ferulate), and the three major anthocyanins (cyanidin coumaroyl glycoside, peonidin coumaroyl glycoside and delphinidin diacetyl diglycoside) and a flavone diglucoside, being the interglucosidic linkage (12), to the best of our knowledge, reported for the first time in a diglucoside of apigenin. The analytic conditions, retention times and fragmentation pattern reported now may constitute a fast tool for the systematic identification of these compounds in plant extracts. References: 1- Speta, F., 1998. Systematishe Analyse de gattung Scilla L. s.l. (Hyacinthaceae). Phyton 38(1), 87-95, 121-123. 2- Speta, F., 1998. Hyacinthaceae. In: Kubitzki, K., (Ed.). The families and genera of vascular plants. III. Flowering plants: Monocotyledons. Springer Verlag, Berlin, pp. 261-285. 3- Kopp, B., Krenn, L., Draxler, M., Hoyer, A., Terkola, R., Vallaster, P., Robien, W., 1996. Bufadienolides from Urginea maritima from Egypt. Phytochemistry 42(2), 513-522. 4- Harborne, J.B., Williams, C.A., 1994. Recent advances in the chemosystematics of the monocotyledons. Phytochemistry 37(1), 3-18. 5- Kite, G.C., Grayer, R., Rudall, P., Simmonds, M.S.J., 2000. The potential for chemical characters in monocotyledon systematics. in: Wilson, K.L., Morrison, D.A., (Eds.). Monocotyledons: systematics and evolution. CSIRO, Melbourne, pp. 101-113.

This research was carried out with financial support from Fundação para a Ciência e Tecnologia (FCT/POCTI/FEDER) and Project POCTI QUI/119/94 “Structure and Reactivity of Flavonoid Glycosides and Synthetic Analogues: A Fundamental Research by Mass Spectrometry”.