Isolation, Structural Elucidation, and Biological Evaluation of a 5‑Hydroxymethyl-2-furfural Derivative, Asfural, from Enzyme-Treated Asparagus Extract

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 spectroscopi...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2013-09, Vol.61 (38), p.9155-9159
Main Authors: Ito, Tomohiro, Sato, Atsuya, Ono, Tomoko, Goto, Kazunori, Maeda, Takahiro, Takanari, Jun, Nishioka, Hiroshi, Komatsu, Kenichi, Matsuura, Hideyuki
Format: Article
Language:English
Subjects:
Asparagus Plant - chemistry
Biological and medical sciences
Cell Line, Tumor
Food industries
Fruit and vegetable industries
Fundamental and applied biological sciences. Psychology
Furaldehyde - analogs & derivatives
Furaldehyde - chemistry
Furaldehyde - isolation & purification
Furaldehyde - pharmacology
Gene Expression - drug effects
heat shock proteins
high performance liquid chromatography
HSP70 Heat-Shock Proteins - genetics
HSP70 Heat-Shock Proteins - metabolism
Humans
hydroxymethylfurfural
messenger RNA
Molecular Structure
nuclear magnetic resonance spectroscopy
Plant Extracts - chemistry
Plant Extracts - isolation & purification
Plant Extracts - pharmacology
Polygalacturonase - chemistry
Sucrase - chemistry
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Summary: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.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf402010c