Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds

J Nat Prod. 2002 Feb;65(2):206-9. doi: 10.1021/np010073b.

Abstract

Four lignanamides, a tyramine derivative, and 10 other nonalkaloidal components were isolated from the seeds of Hyoscyamus niger. Among them, hyoscyamide (1), 1,24-tetracosanediol diferulate (6), and 1-O-(9Z,12Z-octadecadienoyl)-3-O-nonadecanoyl glycerol (7) are new structures. The other compounds were identified as grossamide, cannabisin D, cannabisin G, N-trans-feruloyl tyramine, 1-O-octadecanoyl glycerol, 1-O-(9Z,12Z-octadecadienoyl) glycerol, 1-O-(9Z,12Z-octadecadienoyl)-2-O-(9Z,12Z-octadecadienoyl) glycerol, 1-O-(9Z,12Z-octadecadienoyl)-3-O-(9Z-octadecenoyl) glycerol, rutin, vanillic acid, beta-sitosterol, and daucosterol. Grossamide, and cannabisins D and G exhibited moderate cytotoxicity in cultured LNCaP human prostate cancer cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • China
  • Chromatography, Thin Layer
  • Coumaric Acids / chemistry
  • Coumaric Acids / isolation & purification*
  • Coumaric Acids / pharmacology
  • Drug Screening Assays, Antitumor
  • Fatty Acids / chemistry
  • Fatty Acids / isolation & purification*
  • Fatty Acids / pharmacology
  • Glycerol / analogs & derivatives
  • Glycerol / chemistry
  • Glycerol / isolation & purification*
  • Glycerol / pharmacology
  • Humans
  • Hydrolysis
  • Inhibitory Concentration 50
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Male
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Prostatic Neoplasms
  • Seeds / chemistry
  • Solanaceae / chemistry*
  • Spectrophotometry, Infrared
  • Spectroscopy, Fourier Transform Infrared
  • Stereoisomerism
  • Tumor Cells, Cultured / drug effects
  • Tyramine / analogs & derivatives
  • Tyramine / chemistry
  • Tyramine / isolation & purification
  • Tyramine / pharmacology

Substances

  • 1,24-tetracosanediol diferulate
  • 1-O-(9Z,12Z-octadecadienoyl)-3-O-nonadecanoyl glycerol
  • Coumaric Acids
  • Fatty Acids
  • Lignans
  • hyoscyamide
  • Glycerol
  • Tyramine