Disease relevance of Oxophenylethane

• A novel phenylacetaldehyde reductase was purified about 50-fold to homogeneity from Corynebacterium sp. strain ST-10, which can assimilate gaseous styrene as the sole carbon and energy source [1].
• Consistent with this explanation, the bactericidal effect of phenylacetaldehyde is also stronger with gram-negative bacteria [2].
• Phenylacetaldehyde O-methyloxime: a volatile compound produced by grapefruit leaves infected with the citrus canker pathogen, Xanthomonas axonopodis pv. citri [3].

High impact information on Oxophenylethane

• PAAS is a bifunctional enzyme that catalyzes the unprecedented efficient coupling of phenylalanine decarboxylation to oxidation, generating phenylacetaldehyde, CO2, ammonia, and hydrogen peroxide in stoichiometric amounts [4].
• The enzyme required NADH as a cofactor and showed no activity with NADPH; therefore, it was defined as an NADH-dependent phenylacetaldehyde reductase [1].
• Inhibition constants (Ki) for DPAB, estimated from Dixon plots, were 10 nM (propanal) and 77 nM (phenylacetaldehyde) for mouse ALDH and 3 nM (propanal) and 70 nM (phenylacetaldehyde) for human ALDH [5].
• After incubation with human liver microsomes for 20 min, almost 50% of a 0.03 microM concentration of [3H]-fentanyl was metabolized to the [3H]N-dealkylated metabolite phenylacetaldehyde, which was then converted principally to [3H]2-phenylethanol and to a smaller extent to [3H]phenylacetic acid in microsomal incubates [6].
• While AOR oxidized a wide range of aliphatic and aromatic aldehydes, those with the highest apparent kcat/Km values (> 10 microM-1S-1) were acetaldehyde, isovalerylaldehyde, and phenylacetaldehyde (Km values of < 100 microM) [7].

Chemical compound and disease context of Oxophenylethane

• An aldehyde oxime O-methyl ether, phenylacetaldehyde O-methyloxime, was detected using solid-phase microextraction (SPME) and gas chromatography-mass spectrometry (GC-MS) in the headspace above grapefruit leaves infected with Xanthomonas axonopodis pv. citri, the causal agent of citrus bacterial canker disease (CBCD) [3].

Biological context of Oxophenylethane

• Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation [4].
• NMR analyses of urine showed that a major portion (> 95%) of the excreted (13)C-derived metabolites was derived from hydrolysis of SO, while only a small percentage of the excreted metabolites (< 5%) was derived from metabolism via phenylacetaldehyde [8].
• Intraperitoneal treatment with phenylacetaldehyde and phenylacetic acid (3 x 100 mg/kg b.w./day) increased the levels of apoptosis and cell proliferation in the alveoli without producing any effects in the terminal bronchioli, the target site of tumor formation in mice [9].
• The light emission and the loss of cell viability observed when phenylacetaldehyde is added to neutrophils are greatly enhanced when phenylacetaldehyde is administered as a Schiff base with amino acids [10].

Anatomical context of Oxophenylethane

• Generation of electronically excited states in situ. Polymorphonuclear leukocytes treated with phenylacetaldehyde [11].

Associations of Oxophenylethane with other chemical compounds

• Our objective was to identify the structural gene(s) required for the decarboxylation of phenylpyruvate to phenylacetaldehyde, the first specific step in the Ehrlich pathway [12].
• BCP 54 preferentially oxidizes aromatic aldehyde such as benzaldehyde with NAD as coenzyme, but cannot oxidize phenylacetaldehyde [13].
• In polymorphonuclear leukocytes phenylacetaldehyde promotes an intracellular O2 consuming process in which myeloperoxidase participates [11].
• Moths were trained to feed on flowers that were odour-enhanced using either phenylacetaldehyde or alpha-pinene [14].
• These compounds were subsequently identified using GC linked to mass spectrometry as benzaldehyde, (S)-(-)-limonene, (R,S)-(+/-)-linalool, (E)-myroxide, (Z)-beta-ocimene, phenylacetaldehyde, and (R)-(-)-piperitone [15].

Gene context of Oxophenylethane

• Aldehyde dehydrogenase was the predominant enzyme involved in phenylacetaldehyde oxidation and thus it has a major role in 2-phenylethylamine metabolism with aldehyde oxidase playing a less prominent role [16].
• Metabolism of 2-phenylethylamine to phenylacetaldehyde is catalysed by monoamine oxidase B but the oxidation to its acid is usually ascribed to aldehyde dehydrogenase and the contribution of aldehyde oxidase and xanthine oxidase, if any, is ignored [16].

Analytical, diagnostic and therapeutic context of Oxophenylethane

• In field bioassays using a mixture of the active G. odoratissima compounds and phenylacetaldehyde alone we caught a total of 25 moths, some of which carried Gymnadenia pollinia [17].
• This work attempts to relate the oxidation "status" evaluate by potentiometric titrations, with sensorial degradation and the levels of substances responsible for "off-flavors", such as methional and phenylacetaldehyde [18].
• Cloning, sequence analysis, and expression in Escherichia coli of the gene encoding phenylacetaldehyde reductase from styrene-assimilating Corynebacterium sp. strain ST-10 [19].

References