Scropolioside-D2 and harpagoside-B: two new iridoid glycosides from Scrophularia deserti and their antidiabetic and antiinflammatory activity

Biol Pharm Bull. 2003 Apr;26(4):462-7. doi: 10.1248/bpb.26.462.

Abstract

Five iridoid glycosides, including the two new compounds scropolioside-D(2) (1) and harpagoside-B (2), were isolated from the aerial parts of Scrophularia deserti DEL (Scrophulariaceae). Their structures were elucidated on the basis of spectral data to be 6-O-[2",4"-di-O-acetyl-3"-O-trans-cinnamoyl)-alpha-L-rhamnopyranosyl]-8 alpha-hydroxymethyl-1 alpha,5 beta,6 alpha,7 alpha,9 beta-pentahydro-7(8)-epoxy-2-oxaind-3-ene-1-O-beta-D-glucopyranoside-6'-O-acetate (1) and 5-O-beta-hydroxy-8-O-beta-trans-cinnamoyl-8 alpha-methyl-1,6,7,9-tetrahydro-2-oxaind-3-ene-1-O-beta-D-glucopyranoside (2), respectively. In addition, three more iridoid glycosides, scropolioside-D (3), koelzioside (4), and 8-O-acetyl-harpagide (5), were also isolated and characterized from this source. The biological activity and the structure activity relationship of the compounds were also studied, and scropolioside-D (3) and harpagoside-B (2) were found to possess significant antidiabetic and antiinflammatory activity, respectively.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / therapeutic use*
  • Diabetes Mellitus, Experimental / chemically induced
  • Diabetes Mellitus, Experimental / drug therapy
  • Edema / chemically induced
  • Edema / drug therapy
  • Female
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / therapeutic use*
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / therapeutic use*
  • Iridoid Glucosides
  • Iridoids / chemistry
  • Iridoids / isolation & purification
  • Iridoids / pharmacology
  • Iridoids / therapeutic use*
  • Male
  • Mice
  • Plant Components, Aerial
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / therapeutic use
  • Pyrans / chemistry
  • Pyrans / isolation & purification
  • Pyrans / therapeutic use*
  • Rats
  • Rats, Wistar
  • Scrophularia*

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Glycosides
  • Hypoglycemic Agents
  • Iridoid Glucosides
  • Iridoids
  • Plant Extracts
  • Pyrans
  • scropolioside D
  • harpagoside