Malondialdehyde

Malondialdehyde
Names
IUPAC name
propanedial
Other names
Malonic aldehyde; Malonodialdehyde; Propanedial; 1,3-Propanedial ; Malonaldehyde
Identifiers
542-78-9 YesY
3D model (Jmol) Interactive image
Abbreviations MDA
ChemSpider 10499 N
KEGG C19440 YesY
PubChem 10964
Properties
C3H4O2
Molar mass 72.06 g·mol−1
Appearance Needle-like solid[1]
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[1]
REL (Recommended)
 Ca[1]
IDLH (Immediate danger)
 Ca [N.D.][1]
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).
N verify (what is YesYN ?)
Infobox references

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]

See also

References

  1. 1 2 3 4 "NIOSH Pocket Guide to Chemical Hazards #0377". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 4 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
  3. 1 2 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.
  4. ↑ J. Biol. Chem. 248:5673; 1973
  5. ↑ Proc. Natl. Acad. Sci. USA 71:3400; 1974
  6. ↑ Prostaglandins Other Lipid Mediat. 1998 Jun;56(2-3):53-76
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ Moore K, Roberts LJ (1998). "Measurement of lipid peroxidation". Free Radic. Res. 28 (6): 659–71. doi:10.3109/10715769809065821. PMID 9736317.
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33 Archived September 14, 2006, at the Wayback Machine.
  13. ↑ Hartman PE, Putative mutagens and carcinogens in foods. IV. Malonaldehyde (malondialdehyde) Environ Mutagen. 1983;5(4):603-7
  14. ↑ 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
  15. ↑ 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.
  16. ↑ 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 Research & Therapy. 9 (4): R76. doi:10.1186/ar2274. PMC 2206377Freely accessible. PMID 17686167.
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