2-methyl-L-erythritol glycosides from Gardenia jasminoides

Fitoterapia. 2013 Sep:89:126-30. doi: 10.1016/j.fitote.2013.05.018. Epub 2013 May 31.

Abstract

Two new glycosides, 2-methyl-L-erythritol-4-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside (1) and 2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside (2), along with two known triterpenoids (3-4), four quinic acid derivatives (5-8) and one flavonoid (9) were isolated from the fruit of Gardenia jasminoides. Their structures were elucidated through MS and 2D NMR experiments (HMQC and HMBC). Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. Though 2-methyl-D-erythritol and its glycosides have been reported in a few references, this is the first report about 2-methyl-L-erythritol glycosides. Based on this finding, we propose that 2-methyl-L-erythritol might be a new intermediate in the non-mevalonate biosynthesis of terpenoids.

Keywords: 2-Methyl-l-erythritol glycosides; Anti-inflammatory activity; Flavonoid; Gardenia jasminoides; Quinic acid derivatives; Triterpenoid.

MeSH terms

  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Drugs, Chinese Herbal / chemistry*
  • Drugs, Chinese Herbal / pharmacology
  • Erythritol / analogs & derivatives*
  • Erythritol / chemistry
  • Erythritol / isolation & purification
  • Erythritol / pharmacology
  • Fruit / chemistry
  • Gardenia / chemistry*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Lipopolysaccharides
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Molecular Structure
  • Nitric Oxide / biosynthesis*
  • Terpenes / isolation & purification
  • Terpenes / pharmacology

Substances

  • 2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-beta-D-glucopyranoside
  • 2-methyl-L-erythritol-4-O-(6-O-trans-sinapoyl)-beta-D-glucopyranoside
  • Anti-Inflammatory Agents
  • Drugs, Chinese Herbal
  • Glycosides
  • Lipopolysaccharides
  • Terpenes
  • Nitric Oxide
  • Erythritol