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Indole alkaloids from Gelsemium elegans.

Ming-Xue Sun1, Yan Cui2, Yu Li3

  • 1Lab of Toxicology and Pharmacology, Faculty of Naval Medicine, Second Military Medical University, Shanghai, 200433, China.

Phytochemistry
|April 7, 2019
PubMed
Summary
This summary is machine-generated.

Five new monoterpenoid indole alkaloids from Gelsemium elegans roots were identified. Two compounds showed significant nitric oxide inhibition in macrophage cells, suggesting therapeutic potential.

Keywords:
GelsemiaceaeGelsemium elegansIndole alkaloidNitric oxide

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology
  • Organic Chemistry

Background:

  • Gelsemium elegans is a plant known for its medicinal properties.
  • Indole alkaloids are a diverse class of natural products with various biological activities.

Purpose of the Study:

  • To isolate and characterize new monoterpenoid indole alkaloids from Gelsemium elegans roots.
  • To evaluate the anti-inflammatory potential of the isolated compounds.

Main Methods:

  • Isolation and purification of alkaloids using chromatographic techniques.
  • Structure elucidation through High-Resolution Electrospray Ionization Mass Spectrometry (HRESIMS), X-ray diffraction, Electronic Circular Dichroism (ECD) spectra, and molecular modeling.
  • In vitro anti-inflammatory assay using lipopolysaccharide-induced RAW 264.7 macrophage cells to measure nitric oxide production.

Main Results:

  • Five new monoterpenoid indole alkaloids were identified: 19,20-Epoxyhumantenine, (4R)-19-oxo-gelsevirine N4-oxide, gelsedethenine, 10,11-dimethoxy-N1-demethoxy-gelsemamide, and 11-demethoxy-gelsemazonamide.
  • The structures and absolute configurations of these alkaloids were fully determined.
  • (4R)-19-oxo-gelsevirine N4-oxide and 10,11-dimethoxy-N1-demethoxy-gelsemamide demonstrated significant inhibition of nitric oxide production, with IC50 values of 6.18 ± 1.07 μM and 12.2 ± 1.02 μM, respectively.

Conclusions:

  • The study successfully identified five novel monoterpenoid indole alkaloids from Gelsemium elegans.
  • Two of the isolated alkaloids possess notable anti-inflammatory properties, warranting further investigation for therapeutic applications.