BIOMAT Database Logo BIOMAT Database Logo

DNA strand break by 2,5-dimethyl-4-hydroxy-3(2H)-furanone, a fragrant compound in various foodstuffs. 1996

K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
Tokyo College of Pharmacy, Japan.

2,5-Dimethyl-4-hydroxy-3(2 H)-furanone (DMHF), produced by Maillard reaction of sugar/amino acid and found in various foodstuffs, showed mutagenicity to Salmonella typhimurium TA100 strain with and without S9 mix, and induced micronucleated mouse peripheral reticulocytes. DNA strand breaking activity of the compound at pH 7.4 increased with the increasing dose of the compound and with the increasing incubation time. The breaking activity was inhibited in the presence of superoxide dismutase, catalase, hydroxyl radical scavengers, spin trapping agents, thiol compounds and metal chelators, and also by removal of dissolved oxygen from the incubation mixture. Addition of Fe(III) ion to the incubation mixture enhanced the breaking activity. Incubation of DMHF with 5,5-dimethyl-1-pyrroline N-oxide (DMPO) gave electron spin resonance signals characteristic to DMPO-OH adduct, indicating generation of hydroxyl radical. It was found that DMHF generated hydroxyl radical with an aid of a trace amount of metal ions, and induced DNA strand breaking. Mutagenicity and induction of micronucleated reticulocytes by DMHF may be caused as a result of DNA modification via hydroxyl radical.

UI MeSH Term Description Entries
D004249 DNA Damage Injuries to DNA that introduce deviations from its normal, intact structure and which may, if left unrepaired, result in a MUTATION or a block of DNA REPLICATION. These deviations may be caused by physical or chemical agents and occur by natural or unnatural, introduced circumstances. They include the introduction of illegitimate bases during replication or by deamination or other modification of bases; the loss of a base from the DNA backbone leaving an abasic site; single-strand breaks; double strand breaks; and intrastrand (PYRIMIDINE DIMERS) or interstrand crosslinking. Damage can often be repaired (DNA REPAIR). If the damage is extensive, it can induce APOPTOSIS. DNA Injury,DNA Lesion,DNA Lesions,Genotoxic Stress,Stress, Genotoxic,Injury, DNA,DNA Injuries
D005609 Free Radicals Highly reactive molecules with an unsatisfied electron valence pair. Free radicals are produced in both normal and pathological processes. Free radicals include reactive oxygen and nitrogen species (RONS). They are proven or suspected agents of tissue damage in a wide variety of circumstances including radiation, damage from environment chemicals, and aging. Natural and pharmacological prevention of free radical damage is being actively investigated. Free Radical
D005663 Furans Compounds with a 5-membered ring of four carbons and an oxygen. They are aromatic heterocycles. The reduced form is tetrahydrofuran. Tetrahydrofurans
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D012486 Salmonella typhimurium A serotype of Salmonella enterica that is a frequent agent of Salmonella gastroenteritis in humans. It also causes PARATYPHOID FEVER. Salmonella typhimurium LT2
D015162 Micronucleus Tests Induction and quantitative measurement of chromosomal damage leading to the formation of micronuclei (MICRONUCLEI, CHROMOSOME-DEFECTIVE) in cells which have been exposed to genotoxic agents or IONIZING RADIATION. Micronucleus Assays,Assay, Micronucleus,Assays, Micronucleus,Micronucleus Assay,Micronucleus Test,Test, Micronucleus,Tests, Micronucleus
D015416 Maillard Reaction A group of nonenzymatic reactions in which ALDEHYDES; KETONES; or reducing sugars react with the amino groups of AMINO ACIDS; PEPTIDES; PROTEINS; LIPIDS; or NUCLEIC ACIDS.The reaction with reducing sugars (glycation) results in formation of Schiff bases which undergo Amadori rearrangement and other reactions that result in the irreversible formation of ADVANCED GLYCATION END PRODUCTS (AGEs). Food browning, such as occurs when cooking with high heat (grilling, frying, roasting, etc.) is attributed to the Maillard reaction. Non-enzymatic glycation and subsequent formation of AGEs also occurs in vivo and is accelerated under hyperglycemic and inflammatory conditions, and OXIDATIVE STRESS. Browning Reaction,Food Browning,Fructation,Glucation,Glycation,Lipid Glycation,Non-Enzymatic Glycation,Non-Enzymatic Glycosylation,Nonenzymatic Protein Glycation,Protein Glycation,Ribation,Browning Reactions,Browning, Food,Glycation, Lipid,Glycation, Non-Enzymatic,Glycation, Protein,Glycosylation, Non-Enzymatic,Non Enzymatic Glycation,Non Enzymatic Glycosylation,Protein Glycation, Nonenzymatic,Reaction, Browning,Reaction, Maillard,Reactions, Browning
D051379 Mice The common name for the genus Mus. Mice, House,Mus,Mus musculus,Mice, Laboratory,Mouse,Mouse, House,Mouse, Laboratory,Mouse, Swiss,Mus domesticus,Mus musculus domesticus,Swiss Mice,House Mice,House Mouse,Laboratory Mice,Laboratory Mouse,Mice, Swiss,Swiss Mouse,domesticus, Mus musculus

Related Publications

K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
Natural 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol®).
June 2013, Molecules (Basel, Switzerland),
K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
Mechanisms of melanogenesis inhibition by 2,5-dimethyl-4-hydroxy-3(2H)-furanone.
August 2007, The British journal of dermatology,
K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
A glucosyltransferase specific for 4-hydroxy-2,5-dimethyl-3(2H)-furanone in strawberry.
September 2018, Bioscience, biotechnology, and biochemistry,
K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
Glucosylation of 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, the Key Strawberry Flavor Compound in Strawberry Fruit.
May 2016, Plant physiology,
K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF); antimicrobial compound with cell cycle arrest in nosocomial pathogens.
January 2007, Life sciences,
K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
4-hydroxy-2,5-dimethyl-3(2H)-furanone formation by Zygosaccharomyces rouxii: effect of the medium.
July 2003, Journal of agricultural and food chemistry,
K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
Tautomerism of 4-hydroxy-2,5-dimethyl-3(2H)-furanone: evidence for its enantioselective biosynthesis.
August 2003, Chirality,
K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
Formation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone through methylglyoxal: a Maillard reaction intermediate.
August 2008, Journal of agricultural and food chemistry,
K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
Formation of 4-hydroxy-2,5-dimethyl-3[2H]-furanone by Zygosaccharomyces rouxii: identification of an intermediate.
July 2003, Applied and environmental microbiology,
K Hiramoto, and R Aso-o, and H Ni-iyama, and S Hikage, and T Kato, and K Kikugawa
Structural basis for the enzymatic formation of the key strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone.
June 2013, The Journal of biological chemistry,
Copied contents to your clipboard!