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Kaempferol triosides from Silphium perfoliatum.

Nabil H el-Sayed1, Małgorzata Wojcińska, Krystyna Drost-Karbowska

  • 1National Research Centre, El-Tahrir St., Dokki, Cairo, Egypt. nabil_17@yahoo.com

Phytochemistry
|August 2, 2002
PubMed
Summary

Two new apiose-containing kaempferol triosides were identified in Silphium perfoliatum L. leaves. These compounds were characterized using advanced spectroscopic techniques and acid hydrolysis.

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Area of Science:

  • Phytochemistry
  • Natural Product Chemistry
  • Organic Chemistry

Background:

  • Silphium perfoliatum L. is a medicinal plant with a rich history of traditional use.
  • Flavonoids are a diverse group of plant secondary metabolites known for their biological activities.
  • Previous research has indicated the presence of various flavonoids in S. perfoliatum.

Purpose of the Study:

  • To isolate and characterize novel flavonoid compounds from the leaves of Silphium perfoliatum L.
  • To elucidate the chemical structures of newly discovered compounds using comprehensive analytical methods.
  • To contribute to the understanding of the phytochemical profile of S. perfoliatum.

Main Methods:

  • Isolation of compounds using chromatographic techniques.

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  • Structure elucidation employing acid hydrolysis.
  • Spectroscopic analysis including UV-Vis, LSI MS, FAB MS, CI MS, 1D NMR (1H, 13C, DEPT), and 2D NMR (HMQC, HMBC).

    • Main Results:

    • Two new apiose-containing kaempferol triosides were successfully isolated and identified.
    • Nine known flavonoids were also isolated from the plant material.
    • The structures of the new compounds were confirmed through detailed spectroscopic data and hydrolysis.
    • The identified new compounds are kaempferol 3-O-beta-D-apiofuranoside 7-O-alpha-L-rhamnosyl-(1"-->6")-O-beta-D-galactopyranoside and kaempferol 3-O-beta-D-apiofuranoside 7-O-alpha-L-rhamnosyl-(1''''-->6")-O-beta-D (2"'-O-E-caffeoylgalactopyranoside).

    Conclusions:

    • The phytochemical investigation of Silphium perfoliatum L. leaves led to the discovery of two novel flavonoid glycosides.
    • The structural elucidation confirmed the presence of unique apiose-containing kaempferol triosides.
    • This study expands the knowledge of S. perfoliatum's chemical constituents and provides a basis for further pharmacological research.