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New nor-ursane type triterpenoids from Gelsemium elegans.

Hong-Ru Wu1, Xiao-Feng He1, Xiao-Jie Jin1

  • 1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.

Fitoterapia
|September 8, 2015
PubMed
Summary

Five new nor-ursane triterpenoids, gelse-norursane A-E, were isolated from Gelsemium elegans. These compounds, along with twenty known ones, were evaluated for their cytotoxic effects on various human cancer cell lines.

Keywords:
12-Hydroxy-pregna-4,16-diene-3,20-dione (9 CID 155941)14-Hydroxygelsenicine (20 CID 14217347)5α,6β-Dihydroxysitostrerol (11 CID 23427231)6-Hydroxy-7-methoxycoumarin (16 CID 69894)8-Hydroxypinoresinol (13 CID 3010930)Absolute configurationsEthyl caffeate (15 CID 5317238)Ethyl p-coumarate (14 CID 676946)GEIR-2 (17 CID 10398318)Gelsemine (23 CID 23817963)Gelsemium elegansGelsenicine (19 CID 21123652)Humantenine (21 CID 44593672)Koumine (22 CID 20056077)LoganiaceaeNor-ursane triterpenoidsPinoresinol (12 CID 73399)Ursolic acid (6 CID 3001199)

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Area of Science:

  • Natural Product Chemistry
  • Organic Chemistry
  • Pharmacology

Background:

  • Gelsemium elegans is a plant species known for its rich phytochemical profile.
  • Triterpenoids are a diverse class of natural products with a wide range of biological activities.
  • The 24-nor-ursane skeleton is a less common triterpenoid subclass.

Purpose of the Study:

  • To isolate and characterize new triterpenoids from Gelsemium elegans.
  • To investigate the cytotoxic potential of isolated compounds against human cancer cell lines.
  • To report the first isolation of 24-nor-ursane type triterpenoids from the Loganiaceae family.

Main Methods:

  • Phytochemical investigation involving extraction and chromatographic separation techniques.
  • Structure elucidation using high-resolution electrospray ionization mass spectrometry (HRESIMS) and 1D/2D Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Determination of absolute configurations using experimental and calculated Electronic Circular Dichroism (ECD) spectra.
  • Cytotoxicity evaluation using the MTT assay against HL60, Hela, Hep-G2, and Smmc 7221 cell lines.

Main Results:

  • Five new 24-nor-ursane type triterpenoids, designated gelse-norursane A-E, were successfully isolated and their structures elucidated.
  • Twenty known triterpenoids were also identified from the plant extract.
  • The absolute configurations of compounds 1 and 4 were confirmed.
  • Gelse-norursane A-E represent the first reported 24-nor-ursane triterpenoids from the Loganiaceae family.
  • Selected compounds demonstrated varying degrees of cytotoxicity against the tested cancer cell lines in vitro.

Conclusions:

  • The study successfully identified novel 24-nor-ursane triterpenoids from Gelsemium elegans.
  • The isolated compounds, particularly the new gelse-norursanes, warrant further investigation for their potential anticancer properties.
  • This research expands the known chemical diversity of triterpenoids within the Loganiaceae family.