Glycosylation of capsaicin and 8-nordihydrocapsaicin by cultured cells of Catharanthus roseus

Phytochemistry. 2007 May;68(10):1391-6. doi: 10.1016/j.phytochem.2007.03.005. Epub 2007 Apr 20.

Abstract

The glycosylation of capsaicin and 8-nordihydrocapsaicin was investigated using cultured cells of Catharanthus roseus. In addition to capsaicin 4-O-beta-d-glucopyranoside (170 microg/g fr. wt of cells), the biotransformation products, capsaicin 4-O-(6-O-beta-D-xylopyranosyl)-beta-D-glucopyranoside (116 microg/g fr. wt of cells) and capsaicin 4-O-(6-O-alpha-L-arabinopyranosyl)-beta-D-glucopyranoside (83 microg/g fr. wt of cells), were isolated from the cell suspension after three days of incubation with capsaicin. Two other compounds, 8-nordihydrocapsaicin 4-O-(6-O-beta-D-xylopyranosyl)-beta-D-glucopyranoside (171 microg/g fr. wt of cells) and 8-nordihydrocapsaicin 4-O-(6-O-alpha-L-arabinopyranosyl)-beta-D-glucopyranoside (122 microg/g fr. wt of cells), together with the known 8-nordihydrocapsaicin 4-O-beta-D-glucopyranoside (204 microg/g fr. wt of cells) were also isolated from the cell suspension after incubation with 8-nordihydrocapsaicin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Capsaicin / analogs & derivatives*
  • Capsaicin / chemistry
  • Capsaicin / metabolism*
  • Catharanthus / metabolism*
  • Cells, Cultured
  • Glycosylation

Substances

  • nordihydrocapsaicin
  • Capsaicin