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

• Published in: Journal of agricultural and food chemistry Vol. 61; no. 38; pp. 9155 - 9159
• Main Authors: Ito, Tomohiro, Sato, Atsuya, Ono, Tomoko, Goto, Kazunori, Maeda, Takahiro, Takanari, Jun, Nishioka, Hiroshi, Komatsu, Kenichi, Matsuura, Hideyuki
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 25.09.2013; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Asparagus Plant - chemistry; Biological and medical sciences; Cell Line, Tumor; Chemistry; Chemistry, Applied; Food industries; Food Science & Technology; 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; Life Sciences & Biomedicine; messenger RNA; Molecular Structure; nuclear magnetic resonance spectroscopy; Physical Sciences; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Extracts - pharmacology; Polygalacturonase - chemistry; Science & Technology; Sucrase - chemistry; HMF; ETAS; asfural; HSP70; antistress function; 5-hydroxymethyl-2-furfural; Asparagus officinalis L; asparagus; heat shock protein; enzyme-treated asparagus; HEAT-SHOCK-PROTEIN-70; TRANSLOCATION; LOCALIZATION; ACTIVATION; TRANSCRIPTION; HEAT-SHOCK PROTEINS; ACCUMULATION; STRESS; OLIGOMERIZATION; Evaluation; Monocotyledones; Vegetables; Enzyme; Furfural(hydroxymethyl); Extract; Asparagus officinalis; Asparagus (food); Liliaceae; Angiospermae; Heat shock protein; Isolation; Spermatophyta
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf402010c

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.