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Arachidonic acid as a bioactive molecule
Open accessAbstract
Prostaglandins and their precursorsArachidonic acid is a slippery molecule that owes its mobility to its four cis double bonds.These are the source of its flexibility, keeping the pure fatty acid liquid, even at subzero temperatures, and helping to give mammalian cell membranes their correct fluidity at physiological temperatures.The double bonds are also the key to the propensity of arachidonic acid to react with molecular oxygen.This can happen nonenzymatically, contributing to oxidative stress, or through the actions of three types of oxygenase: cyclooxygenase (COX), lipoxygenase (LOX), and cytochrome P450.While the products of these enzymes and of the nonenzymatic transformations have well-substantiated bioactivities, unchanged arachidonic acid itself has biological activity.This will be a main focus this review.Before dealing with bioactivity, I will consider the solubility properties of the molecule, which are crucial to understanding the availability within the cell of endogenous and exogenous arachidonic acid.I then discuss two controversial issues, arachidonic acid transport into cells and the accessibility of added arachidonic acid to endogenous cellular compartments, and finally turn to selected biological actions of this lipid.The enzymes of arachidonic acid release have been well covered in specialized reviews and are introduced here only in passing. Physical properties and their relevance to the distribution of arachidonic acidThe sodium salt of arachidonic acid is a soap, the same as might be prepared for any other long-chain fatty acid.It can be dissolved fairly readily in aqueous solution.This is in complete contrast to arachidonic free acid, which is an insoluble oil.Interconversion of the salt (ionic) and nonionic forms of arachidonic acid occurs in the range of normal physiological pH.The high pKa of arachidonic acid is crucial, as it sets the solubility properties and the possible distribution of the unesterified fatty acid in cells.It is also central to many of the topics of this review, as most studies of enzymatic transformations and biological activities of arachidonic acid are dependent on addition of exogenous arachidonic acid to cells and tissues.What is the solubility of this added arachidonic acid, and where will it distribute?Cells have hydrophobic (membrane and protein) sites and aqueous/polar sites, so "choices" are available for the different ionic forms of the fatty acid.Like other fatty acids (and certain other membrane components, including acylated pro- Arachidonic acid as a bioactive molecule
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Citations
Cites
Spector, A. A. (1999) · Lipids · doi:10.1007/bf02562220 · Cited by 310
Ligand Selectivity of the Peroxisome Proliferator-Activated Receptor α
Lin, Q., Ruuska, S. E., Shaw, N. S., Dong, D., & Noy, N. (1999) · Biochemistry · doi:10.1021/bi9816094 · Cited by 263
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Arachidonic acid: Physiological roles and potential health benefits – A review
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Reid, G., Wielinga, P., Zelcer, N., van der Heijden, I., Kuil, A., de Haas, M., Wijnholds, J., & Borst, P. (2003) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1033060100 · Cited by 463
Forsythe, C. E., Phinney, S. D., Fernandez, M. L., Quann, E. E., Wood, R. J., Bibus, D. M., Kraemer, W. J., Feinman, R. D., & Volek, J. S. (2008) · Lipids · doi:10.1007/s11745-007-3132-7 · Cited by 371
Metadata
- Authors
- Brash, A. R.
- Venue
- Journal of Clinical Investigation
- Published
- 2001-06-01
- Volume
- 107
- Issue
- 11
- Pages
- 1339-1345
- ISSN
- 0021-9738 (ISSN-L)
- OpenAlex
- W2124922239
- Cited by
- 571
- References
- 2
- FWCI
- 22.90
- Type
- journal article
- Language
- en
- Open access
- bronze
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