Polyhydroxylated pyrrolidine and piperidine alkaloids from Adenophora triphylla var. japonica (Campanulaceae)

Phytochemistry. 2000 Feb;53(3):379-82. doi: 10.1016/s0031-9422(99)00555-5.

Abstract

Adenophora triphylla var. japonica (Campanulaceae) yielded two new alkaloids, the 6-C-butyl derivative of 2R,5R-bis(hydroxymethyl)-3R,4R-dihydroxypyrrolidine (DMDP) and alpha-1-C-ethyl-fagomine, together with the known alkaloids 1,4-dideoxy-1,4-imino-D-arabinitol, 1-deoxynojirimycin, and 1-deoxymannojirimycin. 6-C-Butyl-DMDP showed inhibitory activity toward almond beta-glucosidase (IC50 = 68 microM), whereas alpha-1-C-ethyl-fagomine inhibited bovine liver beta-galactosidase (IC50 = 29 microM).

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Hydroxylation
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Piperidines / chemistry
  • Piperidines / isolation & purification*
  • Plants / chemistry*
  • Pyrrolidines / chemistry
  • Pyrrolidines / isolation & purification*

Substances

  • Alkaloids
  • Piperidines
  • Pyrrolidines