Elsevier

Phytochemistry Letters

Volume 1, Issue 1, 15 April 2008, Pages 44-48
Phytochemistry Letters

Flavonoids from carnation (Dianthus caryophyllus) and their antifungal activity

https://doi.org/10.1016/j.phytol.2007.10.001Get rights and content

Abstract

A flavonoid glycoside, kaempferol 3-O-β-d-glucopyranosyl (1  2)-O-β-d-glucopyranosyl (1  2)-O-[α-l-rhamnopyranosyl-(1  6)]-β-d-glucopyranoside (1), along with two known C- and O-flavonoid glycosides (2 and 3, respectively), were isolated from carnation (Dianthus caryophyllus). The structures of the isolated compounds have been elucidated unambiguously by UV, MS, and a series of 1D and 2D NMR analyses. The isolated compounds and other flavonoid glycoside analogues exhibited antifungal activity against different Fusarium oxysporum f.sp. dianthi pathotypes.

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 13 in a pure form.

The chemical structures of the known compounds 23 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.

References (23)

  • P. Curir et al.

    The plant antifungal isoflavone genistein is metabolized by Armillaria mellea Vahl to give non-fungitoxic products

    Plant Biosystems

    (2006)
  • Cited by (150)

    • Stabilization of dairy industry sludge with leaf litter using as composting and its effect on Spinacia oleracea plant growth

      2023, Materials Today: Proceedings
      Citation Excerpt :

      In higher plant, they are involved in UV filtration, symbiotic nitrogen fixation and floral pigmentation. They may act as a chemical messenger or physiological regulators [14]. The spinach plant treated with different combination of Dairy and leaf litter waste showed variation in their height, number of leaves.

    • Edible rose flowers: A doorway to gastronomic and nutraceutical research

      2022, Food Research International
      Citation Excerpt :

      Flavonoids are a huge class of polyphenolic secondary metabolites found ubiquitously in plants and are divided into six subgroups based on their structure- flavonols, flavones, isoflavones, flavanones, flavanols, and anthocyanins. These flavonoids help plants by acting as an anti-microbial agent and are responsible for the color and aroma of flowers (Spencer, 2008; Galeotti et al., 2008; Panche, Diwan, and Chandra, 2016). Flavonoids are very useful in treating various health problems such as oxidative stress, mutation, cancer, and inflammation and they also modulate key cellular enzyme functions.

    View all citing articles on Scopus
    View full text