Disease relevance of Cyclohexenone

• Thermoregulated expression and characterization of an NAD(P)H-dependent 2-cyclohexen-1-one reductase in the plant pathogenic bacterium Pseudomonas syringae pv. glycinea [1].
• The formation of the tricyclic ketone system is the result of a ring opening and dehydration of a transient oxabicyclic adduct formed by an intramolecular Diels-Alder cycloaddition of an amidofuran with a cyclohexenone moiety tethered such that it participates in the cycloaddition as the 2pi component [2].
• Effects of 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethylphenyl) cyclohex-2-enone on hepatic haem biosynthesis: species differences in hepatic porphyria [3].

High impact information on Cyclohexenone

• The reactions of several active site mutant forms of bacterial morphinone reductase (MR) with NADH and 2-cyclohexen-1-one as substrates have been studied by stopped-flow and steady-state kinetic methods and redox potentiometry [4].
• NMR spectroscopy and flavin reoxidation studies with 2-cyclohexen-1-one are consistent with His-186 being unprotonated in oxidized, reduced, and ligand-bound MR, suggesting that His-186 is not the key proton donor required for the reduction of 2-cyclohexen-1-one [5].
• Insulin secretion induced by [K+50] plus [G16.7] ([K+50 + G16.7]) was markedly suppressed (70%) by 1 uM nifedipine, a Ca(2+)-channel blocker and was completely abolished by 2 mM 2-cyclohexen-1-one, which reportedly decreases reduced glutathione level and blocks glucokinase [6].
• Participation of glucokinase inactivation in inhibition of glucose-induced insulin secretion by 2-cyclohexen-1-one [7].
• While such a rearrangement can occur post-enzymatically under physiological conditions by acid catalysis, the computations reveal a novel mechanism whereby the active species of the enzyme catalyzes directly the production of phenol and cyclohexenone [8].

Biological context of Cyclohexenone

• Reduction of 2-cyclohexen-1-one by FMNH(2) is concerted with proton transfer from an unknown proton donor in the active site [5].
• Moreover, compounds possessing an alpha,beta-unsaturated carbonyl group, like 2-cyclopenten-1-one and 2-cyclohexen-1-one, reduce pro-inflammatory gene expression [9].
• Complex 1" is an effective (hourly turnover frequency=16) and very selective (100 %) catalyst for the hydrogenation of cyclohexen-2-one to cyclohexanone with dihydrogen under mild conditions [10].
• A sequence of three reactions, enantioselective Birch reduction-allylation, enol ether hydrolysis, and Cope rearrangement, is used to stereoselectively generate chiral quaternary centers on a 2-cyclohexen-1-one ring [11].
• Subsequent reductive amination of this cyclohexenone was found to depend on the nature of the protecting groups and led to the protected form of 4-epi- and -iso-narciclasine [12].

Anatomical context of Cyclohexenone

• Effects of glutathione depletion by 2-cyclohexen-1-one on excitatory amino acids-induced enhancement of activator protein-1 DNA binding in murine hippocampus [13].
• 5,6-Dihydro-2H-pyran-2-one and 2-cyclohexen-1-one also produced substantial depletion of GSH in the direct reaction, which was not increased by the addition of liver microsomes [14].

Associations of Cyclohexenone with other chemical compounds

• We assessed our speculation that 2-cyclohexen-1-one (CHX) impairs glucose-induced insulin secretion through inactivation of glucokinase [7].
• Morphinone reductase was active against morphinone, codeinone, neopinone and 2-cyclohexen-1-one, but not against morphine, codeine or isocodeine [15].
• The recombinant OPR3 protein also showed beta-NADPH oxidation activity in the presence of cyclohexenone, but not cyclohexanone, suggesting that the enzyme has specificity to cleavage of olefinic bonds in cyclic enones [16].
• The polymer-supported Al-Li-bis(binaphthoxide) (ALB) catalyst was more effective than the dendrimer-supported ALB in the Michael reaction of 2-cyclohexen-1-one with dibenzyl malonate affording the adduct in 91% yield with 96% ee [17].
• Conformational study of the acetyl group and cyclohexenone in progesterone interacting with phosphatidyllipid by means of circular dichroism [18].

Gene context of Cyclohexenone

• The cyclohexenone segment 2 of scyphostatin (1), a potent inhibitor of neutral sphingomyelinase, was synthesized in an enantioselective manner starting from the bromo ether 5 and D-serinal derivative 3 [19].
• [reaction: see text] The first example of catalytic asymmetric conjugate addition of TMS-acetylene to a cyclic alpha,beta-enone has been accomplished using the chiral bisoxazoline-Ni complex 9 as catalyst and dimethylalumino TMS-acetylide and 2-cyclohexen-1-one as reactants [20].
• Three hours after administration of the pro-oxidant 2-cyclohexen-1-one, calpain activity was significantly reduced in the brain of young rats, but not in the brain of adult rats, and cathepsin D activity remained unchanged [21].

Analytical, diagnostic and therapeutic context of Cyclohexenone

• The absolute stereochemistry of the cyclohexenone moiety of malyngamide H -1- was deduced by a combination of 2D NOESY and exciton chirality circular dichroism spectroscopy [22].
• Bioassays showed that both the flavone and cyclohexenone significantly inhibited the growth of weeds Echinochloa crus-galli, Cyperus difformis and Cyperus iris, and the spore germination of fungal pathogens Pyricularia oryzae and Rhizoctonia solani at all tested concentrations [23].

References