関: malonaldehyde、MDA

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/02 17:24:04」(JST)

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Malondialdehyde (MDA) is the organic compound with the formula CH₂(CHO)₂. The structure of this species is more complex than this formula suggests. This reactive species occurs naturally and is a marker for oxidative stress.

Structure and synthesis

Malondialdehyde mainly exists in the enol form:^[2]

CH₂(CHO)₂ → HOCH=CH-CHO

In organic solvents, the cis-isomer is favored, whereas in water the trans-isomer predominates.

Malondialdehyde is a highly reactive compound that is not typically observed in pure form. In the laboratory it can be generated in situ by hydrolysis of 1,1,3,3-tetramethoxypropane, which is commercially available.^[2] It is easily deprotonated to give the sodium salt of the enolate (m.p. 245 °C).

Malondialdehyde results from lipid peroxidation of polyunsaturated fatty acids.^[3] It is a prominent product in Thromboxane A2 synthesis wherein cyclooxygenase 1 or cycloxygenase 2 metabolizes arachidonic acid to prostaglandin H2 by platelets and a wide array of other cell types and tissues. This product is further metabolized by Thromboxane synthase to Thromboxane A2, 12-Hydroxyheptadecatrienoic acid, and malonyldialdehyde.^[4]^[5] Alternatively, it may rearrange non-enzymatically to a mixture of 8-cis and 8-trans isomers of 12-hydroxyeicosaheptaenoic acid plus malonyldialdehyde (see 12-Hydroxyheptadecatrienoic acid).^[6] The degree of lipid peroxidation can be estimated by the amount of malondialdehyde in tissues.^[3]

Biochemistry

Reactive oxygen species degrade polyunsaturated lipids, forming malondialdehyde.^[7] This compound is a reactive aldehyde and is one of the many reactive electrophile species that cause toxic stress in cells and form covalent protein adducts referred to as advanced lipoxidation end-products (ALE), in analogy to advanced glycation end-products (AGE).^[8] The production of this aldehyde is used as a biomarker to measure the level of oxidative stress in an organism.^[9]^[10]

Malondialdehyde reacts with deoxyadenosine and deoxyguanosine in DNA, forming DNA adducts, the primary one being M₁G, which is mutagenic.^[11] The guanidine group of arginine residues condense with malondialdehyde to give 2-aminopyrimidines.

Human ALDH1A1 aldehyde dehydrogenase is capable of oxidizing malondialdehyde.

Analysis

Malondialdehyde and other thiobarbituric reactive substances (TBARS) condense with two equivalents of thiobarbituric acid to give a fluorescent red derivative that can be assayed spectrophotometrically.^[2]^[12] 1-Methyl-2-phenylindole is an alternative more selective reagent.^[2]

Hazards and pathology

Malondialdehyde is reactive and potentially mutagenic.^[13] It has been found in heated edible oils such as sunflower and palm oils.^[14]

Corneas of patients suffering from keratoconus and bullous keratopathy have increased levels of malondialdehyde, according to one study.^[15] MDA also can be found in tissue sections of joints from patients with osteoarthritis.^[16]

References

^ ^a ^b ^c ^d "NIOSH Pocket Guide to Chemical Hazards #0377". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c ^d V. Nair, C. L. O'Neil, P. G. Wang "Malondialdehyde", Encyclopedia of Reagents for Organic Synthesis, 2008, John Wiley & Sons, New York. doi:10.1002/047084289X.rm013.pub2 Article Online Posting Date: March 14, 2008
^ ^a ^b Davey MW1, Stals E, Panis B, Keulemans J, Swennen RL (2005). "High-throughput determination of malondialdehyde in plant tissues". Analytical Biochemistry 347 (2): 201–207. doi:10.1016/j.ab.2005.09.041. PMID 16289006.
^ J. Biol. Chem. 248:5673; 1973
^ Proc. Natl. Acad. Sci. USA 71:3400; 1974
^ Prostaglandins Other Lipid Mediat. 1998 Jun;56(2-3):53-76
^ Pryor WA, Stanley JP (1975). "Letter: A suggested mechanism for the production of malondialdehyde during the autoxidation of polyunsaturated fatty acids. Nonenzymatic production of prostaglandin endoperoxides during autoxidation". J. Org. Chem. 40 (24): 3615–7. doi:10.1021/jo00912a038. PMID 1185332.
^ Farmer EE, Davoine C (2007). "Reactive electrophile species". Curr. Opin. Plant Biol. 10 (4): 380–6. doi:10.1016/j.pbi.2007.04.019. PMID 17646124.
^ Moore K, Roberts LJ (1998). "Measurement of lipid peroxidation". Free Radic. Res. 28 (6): 659–71. doi:10.3109/10715769809065821. PMID 9736317.
^ Del Rio D, Stewart AJ, Pellegrini N (2005). "A review of recent studies on malondialdehyde as toxic molecule and biological marker of oxidative stress". Nutr Metab Cardiovasc Dis 15 (4): 316–28. doi:10.1016/j.numecd.2005.05.003. PMID 16054557.
^ Marnett LJ (1999). "Lipid peroxidation-DNA damage by malondialdehyde". Mutat. Res. 424 (1–2): 83–95. doi:10.1016/S0027-5107(99)00010-X. PMID 10064852.
^ http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33^{[dead link]}
^ Hartman PE, Putative mutagens and carcinogens in foods. IV. Malonaldehyde (malondialdehyde) Environ Mutagen. 1983;5(4):603-7
^ Dourerdjou, P.; Koner, B. C. (2008), Effect of Different Cooking Vessels on Heat-Induced Lipid Peroxidation of Different Edible Oils" Journal of Food Biochemistry, 32: 740–751. doi:10.1111/j.1745-4514.2008.00195.x
^ Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ (March 2002). "Evidence of oxidative stress in human corneal diseases". J. Histochem. Cytochem. 50 (3): 341–51. doi:10.1177/002215540205000306. PMID 11850437.
^ Tiku ML, Narla H, Jain M, Yalamanchili P (2007). "Glucosamine prevents in vitro collagen degradation in chondrocytes by inhibiting advanced lipoxidation reactions and protein oxidation". Arthritis Res. Ther. 9 (4): R76. doi:10.1186/ar2274. PMC 2206377. PMID 17686167.

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★リンクテーブル★

リンク元	「MDA」「malonaldehyde」

「MDA」

Malondialdehyde
Names
	IUPAC name propanedial
	Other names Malonic aldehyde; Malonodialdehyde; Propanedial; 1,3-Propanedial ; Malonaldehyde
Identifiers
Abbreviations	MDA
CAS Registry Number	542-78-9
ChemSpider	10499
	InChI InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2 ; Key: WSMYVTOQOOLQHP-UHFFFAOYSA-N ; InChI=1/C3H4O2/c4-2-1-3-5/h2-3H,1H2; Key: WSMYVTOQOOLQHP-UHFFFAOYAU ;
Jmol-3D images	Image
KEGG	C19440
PubChem	10964
	SMILES C(C=O)C=O ;
Properties
Molecular formula	C3H4O2
Molar mass	72.06 g·mol−1
Appearance	Needle-like solid
Density	0.991 g/mL
Melting point	72 °C (162 °F; 345 K)
Boiling point	108 °C (226 °F; 381 K)
Hazards
	US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	Ca
IDLH (Immediate danger)	Ca [N.D.]
Related compounds
Related alkenals	Glucic acid; 4-Hydroxynonenal
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is: /?)
	Infobox references