Elsevier

Phytochemistry

Volume 68, Issue 13, July 2007, Pages 1805-1812
Phytochemistry

Phenolic glycosides from Foeniculum vulgare fruit and evaluation of antioxidative activity

https://doi.org/10.1016/j.phytochem.2007.03.029Get rights and content

Abstract

Two diglucoside stilbene trimers and a benzoisofuranone derivative were isolated from Foeniculum vulgare fruit together with nine known compounds. Their structures were elucidated by spectral methods including 1D, 2D NMR and MS and chemical methods. Antioxidant activity was tested using three methods: DPPHradical dot, total antioxidant capacity and assay of lipid peroxidation.

Graphical abstract

Two diglucoside stilbene trimers and a benzoisofuranone derivative were isolated from Foeniculum vulgare fruits, together with nine known compounds. Their structures were elucidated by spectral methods including 1D, 2D NMR and MS. The antioxidant activity was tested using three methods: DPPH, total antioxidant capacity and assay of lipid peroxidation

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Introduction

Fennel (Foeniculum vulgare Miller, Apiaceae) is a well-known Mediterranean aromatic plant, widespread in middle and southern Italy, which is used in traditional medicine and as spice. Herbal drug preparations, from numerous wild types, are active for dyspeptic complaints, bloating and flatulence (Forster et al., 1980). Diuretic, analgesic and antipyretic activity has also been found in the fennel fruit (Tanira et al., 1996) as well as antioxidant activity (Oktay et al., 2003). The leaves and fruit are mainly used to flavour fish and meat, giving them a strong aroma and taste, and as an ingredient in cosmetics. The most frequently investigated was the essential oil which showed antioxidant, antimicrobial and hepatoprotective activity (Ruberto et al., 2000, Ozbek et al., 2003). The chemical composition of the volatile oil fraction has been well described in the literature (Piccaglia and Marotti, 2001, Badoc et al., 1994, Damianova et al., 2004). Earlier investigation of F. vulgare fruit led to the isolation of phenolic components with antihypertensive activity (Ono et al., 1996, Nyemba et al., 1995).

The aim of this study was to determine the phytochemical composition of the non-volatile fraction of fennel fruit and evaluate antioxidant activity. In this report, we describe the isolation and structure elucidation of two new stilbene trimer diglucosides: foeniculosides X (1) and XI (2) and a new benzoisofuranone derivative (5) together with nine known compounds: cis-miyabenol C (3) (Ono et al., 1995), trans-miyabenol C (4) (Ono et al., 1995), trans-resveratrol 3-O-β-d-glucopyranoside (6) (Nyemba et al., 1995), sinapyl glucoside (7) (Della Greca et al., 1998), syringin 4-O-β-glucoside (8) (Park, 1996), oleanolic acid (9) (Seebacher et al., 2003), 7α-hydroxycampesterol (10) (Louter, 2004), (3β,5α,8α,22E) 5,8-epidioxy-ergosta-6,22-dien-3-ol (11) (Guyot and Durgeat, 1981), and 2,3-dihydropropylheptadec-5-enoate (12) (Coleman et al., 2004). The structural elucidation has been performed by spectral analysis, including various two-dimensional (2D) nuclear magnetic resonance (NMR) techniques and by chemical means. We also describe the antioxidant activity of crude extracts (CCl4, CHCl3, n-BuOH and the aqueous residue) and pure compounds 1, 3, 4, 7 and 8.

Section snippets

Results and discussion

The methanol extract of powdered fresh fruits of F. vulgare was subjected to Kupchan’s partitioning methodology (Kupchan et al., 1973) to give four extracts: n-hexane, CCl4, CHCl3, n-BuOH and the aqueous residue. Crude extracts obtained were tested for their radical scavenging activity (Table 2).

The n-BuOH extract, after purification, yielded two new phenolic diglucosides 1 and 2, the unusual benzoisofuranone derivative (5) and the known compounds: cis-miyabenol C (3), trans-miyabenol C (4) and

General experimental procedures

Fast atom bombardment mass spectrometry (FAB-MS), electron ionization mass spectrometry (EI-MS) high-resolution (HR) FAB-MS were recorded on a Fisons VG Prospec instrument. Optical rotations were determined on a Perkin–Elmer 141 polarimeter. 1H and 13C NMR spectra were determined on a Varian Unity INOVA spectrometer at 500.13 and 125.77 MHz, respectively, equipped with an indirect detection probe. Chemical shifts were referenced to the solvent signals: deuterated methanol (CD3OD) and deuterated

Acknowledgements

The chemical work was supported by MURST Grant PRIN 2004038183/002. MS and NMR spectra were provided by Centro di Servizio Interdipartimentale di Analisi Strumentale (CSIAS), Università di Napoli “Federico II”, Napoli, Italy.

References (29)

  • M. Della Greca et al.

    Antialgal compounds from Zantedeschia aethiopica

    Phytochemistry

    (1998)
  • H.B. Forster et al.

    Antispasmodic effects of some medicinal plants

    Planta Med.

    (1980)
  • R.J. Havel et al.

    The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum

    J. Clin. Invest.

    (1995)
  • H. Kessler et al.

    Separation of cross-relaxation and J cross-peaks in 2D rotating-frame NMR spectroscopy

    J. Am. Chem. Soc.

    (1987)
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