New iridoid glucosides from the aerial parts of Verbena brasiliensis

Chem Pharm Bull (Tokyo). 2006 Oct;54(10):1421-4. doi: 10.1248/cpb.54.1421.

Abstract

Two new iridoid glucosides, verbenabraside A (1) and verbenabraside B (2), were isolated from the aerial parts of Verbena brasiliensis VELL., along with six known iridoid glucosides, gelsemiol 3-O-beta-D-glucoside (3), verbraside (4), 9-hydroxysemperoside (5), griselinoside (6), aralidioside (7), and 6alpha-hydroxyforsythide dimethyl ester (8), three known phenylethanoid glycosides, 2-phenylethyl O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (9), acteoside (10), and leucosceptoside A (11), two known lignan glucosides, dihydroxymethyl-bis(3,5-dimethoxy-4-hydroxyphenyl) tetrahydrofuran-9 (or 9')-O-beta-glucopyranoside (12) and (+)-lyoniresinol 3alpha-O-beta-D-glucopyranoside (13), a known methyl salicylate glucoside, methyl 2-O-beta-D-glucopyranosylbenzoate (14), and two known sterols, beta-sitosterol 3-O-beta-D-glucopyranoside (15) and beta-sitosterol (16). Their chemical structures were determined on the basis of spectroscopic data. Compound 1 exhibited stronger scavenging effect on the stable free radical 1,1-diphenyl-2-picrylhydrazyl than that of alpha-tocopherol.

MeSH terms

  • Iridoids / chemistry*
  • Iridoids / isolation & purification
  • Magnetic Resonance Spectroscopy / methods
  • Models, Molecular
  • Molecular Conformation
  • Plant Components, Aerial / chemistry
  • Sensitivity and Specificity
  • Stereoisomerism
  • Verbena / chemistry*

Substances

  • Iridoids
  • verbenabraside A
  • verbenabraside B