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Chemical Compound Review:

isohexana 4-methylpentanal

Synonyms: isohexanal, AG-D-30682, CHEBI:17998, HMDB01318, WTI-10483, ...

Lefrançois-Martinez, A.M. et al., Matsuura, K. et al., Kotokorpi, P. et al., Val, P. et al., Martinez, A. et al., et al.

Martinez, Val, Sahut-Barnola, Aigueperse, Veyssière, Lefrançois-Martinez,

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Disease relevance of isohexanal

In cells stably transfected with MVDP antisense cDNA, NADH-linked ICR activity was abolished even in the presence of forskolin, and the isocaproaldehyde toxicity was increased compared with that of intact Y1 cells, as measured by isocaproaldehyde LD(50) [1].

High impact information on isohexanal

These results indicate that in adrenocortical cells, MVDP is responsible for detoxifying isocaproaldehyde generated by steroidogenesis [1].
Product of side-chain cleavage of cholesterol, isocaproaldehyde, is an endogenous specific substrate of mouse vas deferens protein, an aldose reductase-like protein in adrenocortical cells [1].
For MVDP, isocaproaldehyde, a product of side-chain cleavage of cholesterol generated during steroidogenesis, is the best natural substrate identified so far [1].
In the zona fasciculata of the adrenal cortex where its expression is controlled by ACTH, AKR1-B7 detoxifies isocaproaldehyde produced during the first step of steroidogenesis [2].
The akr1b7 gene encodes an aldo-keto reductase involved in detoxification of isocaproaldehyde, the product from side chain cleavage of cholesterol, and of 4-hydroxynonenal (4-HNE) formed by lipid peroxidation and cleavage [3].

Biological context of isohexanal

Role of three SF-1 binding sites in the expression of the mvdp/akr1-b7 isocaproaldehyde reductase in Y1 cells [4].

Anatomical context of isohexanal

Here, we report the characterization of enzymes responsible for the oxidoreduction of isocaproaldehyde in human, monkey, dog, and rabbit adrenal glands [5].

Associations of isohexanal with other chemical compounds

NADPH-linked isocaproaldehyde reductase activity in the adrenal extracts of the four species was much higher than the NADH-linked reductase and NAD(P)(+)-linked dehydrogenase activities and was potently inhibited by aldose reductase inhibitors [5].

Gene context of isohexanal

In steroidogenic organs, AKR1B7/MVDP scavenges isocaproaldehyde produced from the cholesterol side-chain cleavage reaction [6].
Thus, aldose reductase acts not only as a major reductase for isocaproaldehyde formed from steroidogenesis but also as a scavenger of aldehydes derived from lipid peroxidation in mammalian adrenal glands [5].

References

Product of side-chain cleavage of cholesterol, isocaproaldehyde, is an endogenous specific substrate of mouse vas deferens protein, an aldose reductase-like protein in adrenocortical cells. Lefrançois-Martinez, A.M., Tournaire, C., Martinez, A., Berger, M., Daoudal, S., Tritsch, D., Veyssière, G., Jean, C. J. Biol. Chem. (1999) [Pubmed]
Adrenocorticotropin/3',5'-cyclic AMP-mediated transcription of the scavenger akr1-b7 gene in adrenocortical cells is dependent on three functionally distinct steroidogenic factor-1-responsive elements. Val, P., Aigueperse, C., Ragazzon, B., Veyssière, G., Lefrançois-Martinez, A.M., Martinez, A. Endocrinology (2004) [Pubmed]
Activation of the glucocorticoid receptor or liver X receptors interferes with growth hormone-induced akr1b7 gene expression in rat hepatocytes. Kotokorpi, P., Gardmo, C., Nyström, C.S., Mode, A. Endocrinology (2004) [Pubmed]
Role of three SF-1 binding sites in the expression of the mvdp/akr1-b7 isocaproaldehyde reductase in Y1 cells. Val, P., Aigueperse, C., Lefrançois-Martinez, A.M., Jean, C., Veyssière, G., Martinez, A. Endocr. Res. (2002) [Pubmed]
Aldose reductase is a major reductase for isocaproaldehyde, a product of side-chain cleavage of cholesterol, in human and animal adrenal glands. Matsuura, K., Deyashiki, Y., Bunai, Y., Ohya, I., Hara, A. Arch. Biochem. Biophys. (1996) [Pubmed]
Steroidogenic factor-1 controls the aldose reductase akr1b7 gene promoter in transgenic mice through an atypical binding site. Martinez, A., Val, P., Sahut-Barnola, I., Aigueperse, C., Veyssière, G., Lefrançois-Martinez, A.M. Endocrinology (2003) [Pubmed]

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