Isolation, structural elucidation, and biological evaluation of a 5-hydroxymethyl-2-furfural derivative, asfural, from enzyme-treated asparagus extract

J Agric Food Chem. 2013 Sep 25;61(38):9155-9. doi: 10.1021/jf402010c. Epub 2013 Sep 13.

Abstract

A novel 5-hydroxymethyl-2-furfural (HMF; 1) derivative, which is named asfural (compound 2), was isolated from enzyme-treated asparagus extract (ETAS) along with HMF (1) as a heat shock protein 70 (HSP70) inducible compound. The structure of compound 2 was elucidated on the basis of its spectroscopic data from HREIMS and NMR, whereas the absolute configuration was determined using chiral HPLC analysis, compared to two synthesized compounds, (S)- and (R)-asfural. As a result, compound 2 derived from ETAS was assigned as (S)-(2-formylfuran-5-yl)methyl 5-oxopyrrolidine-2-carboxylate. When compound 2, synthesized (S)- and (R)-asfural, and HMF (1) were evaluated in terms of HSP70 mRNA expression-enhancing activity in HL-60 cells, compound 2 and (S)-asfural significantly increased the expression level in a concentration-dependent manner. HMF (1) also showed significant activity at 0.25 mg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Asparagus Plant / chemistry*
  • Cell Line, Tumor
  • Furaldehyde / analogs & derivatives*
  • Furaldehyde / chemistry
  • Furaldehyde / isolation & purification
  • Furaldehyde / pharmacology
  • Gene Expression / drug effects
  • HSP70 Heat-Shock Proteins / genetics
  • HSP70 Heat-Shock Proteins / metabolism
  • Humans
  • Molecular Structure
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Polygalacturonase / chemistry*
  • Sucrase / chemistry*

Substances

  • HSP70 Heat-Shock Proteins
  • Plant Extracts
  • 5-hydroxymethylfurfural
  • Furaldehyde
  • Polygalacturonase
  • Sucrase