Flavonoids from carnation (Dianthus caryophyllus) and their antifungal activity
Graphical abstract
The new kaempferol 3-O-β-d-glucopyranosyl (1 → 2)-O-β-d-glucopyranosyl (1 → 2)-O-[α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside (1) has been isolated from carnation (Dianthus caryophyllus) along with two known C- and O-flavonoid glycosides. The isolated compounds exhibited antifungal activity against different Fusarium oxysporum f.sp. dianthi pathotypes.
Introduction
Flavonoids are a class of secondary metabolites generally located in plant leaves as water soluble glycosides in the vacuoles of epidermal cells (Harborne & Williams, 2000). These compounds are not only present in plants as constitutive agents but are also accumulated in plant tissues in response to microbial attack (Harborne, 1999; Grayer & Harborne, 1994).
In a search for natural antifungal compounds from plants (Barile et al., 2007; Curir, Dolci, Lanzotti, & Taglialatela-Scafati, 2001; Curir, Dolci, Dolci, Lanzotti, & De Cooman, 2003; Curir, Dolci, Corea, Galeotti, & Lanzotti, 2006) we have performed a phytochemical screening on leaves of carnation (Dianthus caryophyllus), cultivar Tirana. This species is one of the flower crops cultivated extensively around the world, due to its enduring commercial importance as a cut flower, and its growing employment as a pot plant and in floral compositions. However, carnation growing is affected by diverse natural threats, among which fusaric wilt, caused by Fusarium oxysporum f.sp. dianthi (Fod), could be considered one the major serious diseases (Baker, Nelson, & Lawson, 1985).
Previous study on D. caryophyllus, cultivar Novada, led to the isolation of a kaempferide triglycoside (Curir et al., 2001) that showed the ability to resist Fod infection. Now, from the active extract of cultivar Tirana we have isolated the new flavonoid tetraglycoside, kaempferol 3-O-β-d-glucopyranosyl (1 → 2)-O-β-d-glucopyranosyl (1 → 2)-O-[α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside, along with two known C- and O-flavonoid glycosides (2 and 3, respectively). The stereostructure of the new compound was elucidated by extensive NMR techniques and chemical methods. The flavonoids along with two kaempferol diglycosides (4 and 5), isolated from cultivar Esperia (Galeotti, 2007), have been subjected to antifungal tests on different Fod pathotypes to evaluate the possible involvement of D. caryophyllus flavonoids in resistance to pathogen attack.
Section snippets
Results and discussion
Carnation (D. caryophyllus) fresh stems were extracted with EtOH/MeOH (1:1), homogenized and refluxed for 2 h at 80 °C. The dried extract, dissolved in MeOH/H2O (1:1), was paper filtered, thus obtaining a clear yellow-brown solution that was taken to dryness and then purified by chromatographic steps based on gel filtration and RP-18 chromatography, yielding compounds 1–3 in a pure form.
The chemical structures of the known compounds 2–3 were identified by comparison of UV, FABMS, 1H and 13C NMR
General experimental procedures
Optical rotations were measured on a PerkinElmer 192 polarimeter equipped with a sodium lamp (589 nm) and 10-cm microcell. High-resolution FAB mass spectra (glycerol matrix) were performed on a VG Prospec (FISONS) mass spectrometer. GCMS analysis was performed on a Carlo Erba instrument. 1H and 13C NMR spectra were recorded on a Varian Unity Inova spectrometer at 500.13 and 125.77 MHz, respectively. Chemical shifts were referred to the residual solvent signal (CD3OD: δH 3.31, δC 49.0). The
Acknowledgements
This work was supported by MESCOSAGR Project and by the Italian Ministry of Agriculture, Food and Forestry Policies, VIVAFLOR Project. Mass and NMR spectra were recorded at CSIAS, University of Naples Federico II. The assistance of the staff is gratefully appreciated.
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