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Chemical Compound Review:

non-1-en-1-one non-1-en-1-one

Synonyms: AC1MI1AV

Barrera, G. et al., Van der Vliet, A. et al., Niknahad, H. et al., Kuroda, H. et al., Nilsson, L.O. et al.

Kuroda, Kojima, Kaneda, Takashio,

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High impact information on Nonenal

The final product of the sequential redesign of GST A1-1, mutant GIMFhelix, had a 300-fold increase in catalytic efficiency with nonenal and a >10 times decreased activity with 1-chloro-2,4-dinitrobenzene [1].
The cytotoxicity of alkenals towards hepatocytes was related to their electrophilicity not their hydrophobicity as cytotoxicity decreased as the chain length increased from acrolein to hexenal and then cytotoxicity increased from hexenal to nonenal [2].
In this study, we compared the HNE effects with those of 4-hydroxyoctenal (HOE), 4-hydroxyundecenal (HUE; different lengths of the lipophilic tail), and the analogous aldehydes 2-trans-nonanal (lacking the OH group) and nonenal (lacking the OH group and the trans CC double bond), on HL-60 cell proliferation and c-myc expression [3].
The effects of the lipid peroxidation product 4-hydroxy-2,3-trans-1 nonenal (HNE) on intestinal smooth muscle function have been studied [4].
The lipid peroxidation product 4-hydroxy-2,3-trans-1 nonenal decreases rat intestinal smooth muscle function in-vitro by alkylation of sulphydryl groups [4].

Gene context of Nonenal

To assess the involvement of 9-HPL-like activity in beer staling, we compared the values of the wort nonenal potential, an index for predicting the staleness of beer, with the lipoxygenase and 9-HPL-like activity of 20 commercial malts [5].

References

Redesign of substrate-selectivity determining modules of glutathione transferase A1-1 installs high catalytic efficiency with toxic alkenal products of lipid peroxidation. Nilsson, L.O., Gustafsson, A., Mannervik, B. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
Modulating carbonyl cytotoxicity in intact rat hepatocytes by inhibiting carbonyl-metabolizing enzymes. I. Aliphatic alkenals. Niknahad, H., Siraki, A.G., Shuhendler, A., Khan, S., Teng, S., Galati, G., Easson, E., Poon, R., O'Brien, P.J. Chem. Biol. Interact. (2003) [Pubmed]
Effect of bioactive aldehydes on cell proliferation and c-myc expression in HL-60 human leukemic cells. Barrera, G., Pizzimenti, S., Serra, A., Fazio, V.M., Canuto, R.A., Dianzani, M.U. Cancer Detect. Prev. (2000) [Pubmed]
The lipid peroxidation product 4-hydroxy-2,3-trans-1 nonenal decreases rat intestinal smooth muscle function in-vitro by alkylation of sulphydryl groups. Van der Vliet, A., Van der Aar, E.M., Bast, A. J. Pharm. Pharmacol. (1991) [Pubmed]
Characterization of 9-fatty acid hydroperoxide lyase-like activity in germinating barley seeds that transforms 9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid into 2(E)-nonenal. Kuroda, H., Kojima, H., Kaneda, H., Takashio, M. Biosci. Biotechnol. Biochem. (2005) [Pubmed]

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