Elsevier

Fitoterapia

Volume 75, Issue 6, September 2004, Pages 533-538
Fitoterapia

A new acylated quercetin glycoside from Ranunculus lanuginosus

https://doi.org/10.1016/j.fitote.2004.03.014Get rights and content

Abstract

A new acylated quercetin glycoside, quercetin 3-O-(2-t-p-coumaroyl)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside-7-O-β-d-glucopyranoside (1), together with the known 3-(3,4-dihydroxyphenyl)lactic acid (2) were isolated from Ranunculus lanuginosus leaves and identified on the basis of detailed spectral analysis, including 2D-NMR spectrometry and ESI-MS.

Introduction

Flavonoids have been employed as taxonomic markers in Ranunculus spp. There is some pattern of occurrence of flavones, flavonols, O-heterosides, and C-heterosides that allow to establish interspecific relationships even in reduced areas or to redefine the taxonomy of the Ranunculus chromosome type species [1], [2]. Ranunculus lanuginosus is an endemic plant widely distributed in Europe from South-East France to Romania, and extending to Denmark and Estonia [3]. No previous chemical study on this plant is reported. The plant was selected by INCHECO (INsect CHemical ECOlogy) research project since it strongly attracted a species of Monophadnus, an herbivorous sawfly. The aim of the project was to understand all relevant interactions existing among the evolution, ecology, behaviour, morphology, physiology, and chemistry of these insects and their host plants. In the present report, the isolation and the structural characterization of a new acylated quercetin glycoside from the plant leaves, is described.

Section snippets

General

Optical rotations were measured on a Perkin–Elmer 241 polarimeter equipped with a sodium lamp (589 nm) and a 1 dm microcell. Elemental analysis was obtained from a Carlo Erba 1106 elemental analyzer. UV spectra were recorded on a Perkin–Elmer-Lambda 12 spectrophotometer. A Bruker DRX-600 NMR spectrometer using the UXNMR software package was used for NMR experiments [4]. ESIMS (negative mode) were obtained from a Finningan LC-Q Advantage Termoquest spectrometer. TLC was performed on precoated

Results and discussion

The methanolic extract of the fresh leaves of R. lanuginosus was fractionated by Sephadex LH-20 followed by RP-18 flash column chromatography to afford a new quercetin acylated glycoside (1).

Compound 1 was isolated as a yellow amorphous powder. Its molecular formula was established as C42H46O24 by means of ESI-MS, 13C, 13C-DEPT NMR, and elemental analysis. Its ESI-MS spectrum showed a [M-H]- peak at m/z 933, together with two major fragments at m/z 771 (due to the loss of 162 mass unit) and 609

Acknowledgements

The authors acknowledge the financial support provided through the European Community's Improving Human Potential Programme under contract HPRN-CT-1999-00054 INCHECO: Integrated approach to defence strategies in herbivorous Hymenoptera.

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