Anticomplement and antioxidant activities of new acetylated flavonoid glycosides from Centaurium spicatum

Planta Med. 2003 Dec;69(12):1153-6. doi: 10.1055/s-2003-818009.

Abstract

In addition to the three acetylated flavonol glycosides, quercetin 3- O-[(2,3,4-triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-beta-galactopyranoside, quercetin 3- O-[(2,3,4-triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-3-acetyl-beta-galactopyranoside, and quercetin 3- O-[(2,3,4- triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-4-acetyl-beta-galactopyranoside, which have recently been isolated from Centaurium spicatum (L.) Fritsch (Gentianaceae), a new pentaacetylated flavonoid glycoside was isolated from the same plant. Structure elucidation, especially the localization of the acetyl groups, and complete (1)H- and (13)C-NMR assignments, was carried out using one- and two-dimensional NMR methods, including (1)H- and (13)C-NMR, DEPT-135 and DEPT-90, and gradient-assisted experiments such as DQF-COSY, TOCSY, HSQC and HMBC. The structure of the new flavonoid glycoside was established as quercetin 3- O-[(2,3,4-triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-3,4-diacetyl-beta-galactopyranoside. The anticomplement and antioxidant activities of these compounds were evaluated. The triacetylated flavonoid glycoside showed the highest activity in the two assays.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / administration & dosage
  • Antioxidants / pharmacology*
  • Biphenyl Compounds
  • Centaurium*
  • Complement Inactivator Proteins / administration & dosage
  • Complement Inactivator Proteins / pharmacology*
  • Dose-Response Relationship, Drug
  • Flavonoids / administration & dosage
  • Flavonoids / pharmacology*
  • Glycosides / administration & dosage
  • Glycosides / pharmacology*
  • Humans
  • Inhibitory Concentration 50
  • Phytotherapy*
  • Picrates / chemistry
  • Plant Extracts / administration & dosage
  • Plant Extracts / pharmacology

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Complement Inactivator Proteins
  • Flavonoids
  • Glycosides
  • Picrates
  • Plant Extracts
  • anticomplement
  • 1,1-diphenyl-2-picrylhydrazyl