title: Isolation, structural elucidation, and biological evaluation of a 5-hydroxymethyl-2-furfural derivative, asfural, from enzyme-treated asparagus extract.
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.
authors.affiliation: Research and Development Division, Amino Up Chemical Company, Ltd. , 363-32 Shin-ei, Kiyota, Sapporo 004-0839, Japan.
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Ito
authors.forename: Atsuya
authors.initials: A
authors.lastname: Sato
authors.forename: Tomoko
authors.initials: T
authors.lastname: Ono
authors.forename: Kazunori
authors.initials: K
authors.lastname: Goto
authors.forename: Takahiro
authors.initials: T
authors.lastname: Maeda
authors.forename: Jun
authors.initials: J
authors.lastname: Takanari
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nishioka
authors.forename: Kenichi
authors.initials: K
authors.lastname: Komatsu
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Matsuura
mesh_terms: D027761:Asparagus Plant / Q000737:chemistry*; D045744:Cell Line, Tumor; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015870:Gene Expression / Q000187:drug effects; D018840:HSP70 Heat-Shock Proteins / Q000235:genetics / Q000378:metabolism; D006801:Humans; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D011096:Polygalacturonase / Q000737:chemistry*; D013393:Sucrase / Q000737:chemistry*
chemical_list: D018840:HSP70 Heat-Shock Proteins; D010936:Plant Extracts; C008046:5-hydroxymethylfurfural; D005662:Furaldehyde; D011096:Polygalacturonase; D013393:Sucrase