Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. They are a major component of biological membranes and can be easily obtained from a variety of readily available sources, such as egg yolk or soybeans, from which they are mechanically or chemically extracted using hexane. They are also a member of the lecithin group of yellow-brownish fatty substances occurring in animal and plant tissues. Dipalmitoyl phosphatidylcholine (aka: lecithin) is a major component of pulmonary surfactant and is often used in the L/S ratio to calculate fetal lung maturity. While phosphatidylcholines are found in all plant and animal cells, they are absent in the membranes of most bacteria, including Escherichia coli. Purified phosphatidylcholine is produced commercially.
The name "lecithin" was originally defined from the Greek lekithos (λεκιθος, egg yolk) by Theodore Nicolas Gobley, a French chemist and pharmacist of the mid-19th century, who applied it to the egg yolk phosphatidylcholine that he identified in 1847. Gobley eventually completely described his lecithin from chemical structural point of view, in 1874. Phosphatidylcholines are such a major component of lecithin that in some contexts the terms are sometimes used as synonyms. However, lecithin extracts consist of a mixture of phosphatidylcholine and other compounds. It is also used along with sodium taurocholate for simulating fed- and fasted-state biorelevant media in dissolution studies of highly lipophilic drugs.
Phosphatidylcholine is a major constituent of cell membranes and pulmonary surfactant, and is more commonly found in the exoplasmic or outer leaflet of a cell membrane. It is thought to be transported between membranes within the cell by phosphatidylcholine transfer protein (PCTP).
Structure and physical properties
The phospholipid is composed of a choline head group and glycerophosphoric acid, with a variety of fatty acids, one being a saturated fatty acid (in the given figure, this can be palmitic or hexadecanoic acid, H3C-(CH2)14-COOH; margaric acid identified by Gobley in egg yolk, or heptadecanoic acid H3C-(CH2)15-COOH, also belong to that class); and one being an unsaturated fatty acid (here oleic acid, or 9Z-octadecenoic acid, as in Gobley's original egg yolk lecithin).
Phosphatidylcholine is a neutral lipid, but it carries an electric dipole moment of about 10 D. Vibrational dynamics of phosphatidylcholine and its hydration waters has been recently calculated from first principles.
Possible health benefits
Phosphatidylcholine is a vital substance found in every cell of the human body. Thus, some researchers have used mutant mouse models with severe oxidative damage as a model of "accelerated aging" to investigate the possible role of phosphatidylcholine supplementation as a way of slowing down aging-related processes and improving brain functioning and memory capacity in dementia. However, a systematic review of clinical trials in humans found that lecithin or phosphatidylcholine supplementation does not benefit patients with dementia.
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Recent studies have examined potential benefits of phosphatidylcholine for liver repair. Results are mixed in animal models, and no clinical evidence shows a health benefit in humans. One study shows the healing effect of phosphatidylcholine in mice with hepatitis A, hepatitis B, and hepatitis C. The administration of phosphatidylcholine for chronic, active hepatitis resulted in significant reduction of disease activity in mice.[full citation needed][unreliable source?]
Some organizations promote the use of injected phosphatidylcholine, otherwise known as injection lipolysis, claiming the procedure can break down fat cells, and thus serve as an alternative to liposuction. While the procedure cites early experiments that showed lipolysis in cases of fat emboli, no peer-reviewed studies have shown any amount of lipolysis even remotely comparable to liposuction.
Phase IIa/b clinical trials performed at the Heidelberg University Hospital have shown that delayed release purified phosphatidylcholine is an anti-inflammatory agent, and a surface hydrophobicity increasing compound with promising therapeutic potential in the treatment of inflammatory bowel disease.
Possible health risks
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- Phosphatidylcholines at the US National Library of Medicine Medical Subject Headings (MeSH)