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Malondialdehyde

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Malondialdehyde
Names
IUPAC name
propanedial
Other names
Malonic aldehyde; Malonodialdehyde; Propanedial; 1,3-Propanedial ; Malonaldehyde
Identifiers
3D model (JSmol)
Abbreviations MDA
ChemSpider
KEGG
  • InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2 ☒N
    Key: WSMYVTOQOOLQHP-UHFFFAOYSA-N ☒N
  • InChI=1/C3H4O2/c4-2-1-3-5/h2-3H,1H2
    Key: WSMYVTOQOOLQHP-UHFFFAOYAU
  • C(C=O)C=O
Properties
C3H4O2
Molar mass 72.063 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
NIOSH (US health exposure limits):
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 checkY☒N ?)

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. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0377". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ 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
  3. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  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. ^ "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. 1975. doi:10.1021/jo00912a038. PMID 1185332. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  8. ^ "Reactive electrophile species". Curr. Opin. Plant Biol. 10 (4): 380–6. 2007. doi:10.1016/j.pbi.2007.04.019. PMID 17646124. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  9. ^ "Measurement of lipid peroxidation". Free Radic. Res. 28 (6): 659–71. 1998. doi:10.3109/10715769809065821. PMID 9736317. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  10. ^ "A review of recent studies on malondialdehyde as toxic molecule and biological marker of oxidative stress". Nutr Metab Cardiovasc Dis. 15 (4): 316–28. 2005. doi:10.1016/j.numecd.2005.05.003. PMID 16054557. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  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. ^ "Evidence of oxidative stress in human corneal diseases". J. Histochem. Cytochem. 50 (3): 341–51. March 2002. doi:10.1177/002215540205000306. PMID 11850437. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  16. ^ "Glucosamine prevents in vitro collagen degradation in chondrocytes by inhibiting advanced lipoxidation reactions and protein oxidation". Arthritis Research & Therapy. 9 (4): R76. 2007. doi:10.1186/ar2274. PMC 2206377. PMID 17686167. {{cite journal}}: Cite uses deprecated parameter |authors= (help)CS1 maint: unflagged free DOI (link)
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