Flavonoid glucosides from the hairy roots of Catharanthus roseus

J Nat Prod. 2009 Apr;72(4):613-20. doi: 10.1021/np800378q.

Abstract

Four new flavonoid glucosides, 3',4'-di-O-methylquercetin-7-O-[(4''-->13''')-2''',6''',10''',14'''-tetramethylhexadec-13'''-ol-14'''-enyl]-beta-D-glucopyranoside (1), 4'-O-methylkaempferol-3-O-[(4''-->13''')- 2''',6''',10''',14'''-tetramethylhexadecan-13'''-olyl]-beta-D-glucopyranoside (2), 3',4'-di-O-methylbutin-7-O-[(6''-->1''')-3''',11'''-dimethyl-7'''-methylenedodeca-3''',10'''-dienyl]-beta-D-glucopyranoside (3), and 4'-O-methylbutin-7-O-[(6''-->1''')-3''',11'''-dimethyl-7'''-hydroxymethylenedodecanyl]-beta-D-glucopyranoside (4), along with the three known compounds were isolated from the methanol extract of Catharanthus roseus hairy roots. Their structures were elucidated spectroscopically. The new flavonoid glucosides inhibited both MMP-9 activity and TNF-alpha production in THP-1 cells treated with lipopolysaccharide.

MeSH terms

  • Animals
  • Catharanthus / chemistry*
  • Dose-Response Relationship, Drug
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology
  • Humans
  • Lipopolysaccharides / pharmacology
  • Matrix Metalloproteinase Inhibitors*
  • Molecular Structure
  • Plant Roots / chemistry
  • Plants, Medicinal / chemistry*
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors*

Substances

  • Flavonoids
  • Glucosides
  • Lipopolysaccharides
  • Matrix Metalloproteinase Inhibitors
  • Tumor Necrosis Factor-alpha