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 (a.k.a. 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).
Phosphatidylcholine also plays a role in membrane-mediated cell signaling and PCTP activation of other enzymes.
Structure and physical properties
This phospholipid is composed of a choline head group and glycerophosphoric acid, with a variety of fatty acids. Usually, one is 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 the other is an unsaturated fatty acid (here oleic acid, or 9Z-octadecenoic acid, as in Gobley's original egg yolk lecithin). However, there are also examples of disaturated species. Animal lung phosphatidylcholine, for example, contains a high proportion of Dipalmitoylphosphatidylcholine.
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. 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 2009 systematic review of clinical trials in humans found that there was not enough evidence to support the use of lecithin or phosphatidylcholine supplementation for patients with dementia. The study found that a moderate benefit could not be ruled out until further large scale studies are performed.
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.
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. Injection of phosphatidyl choline in small numbers of patients has been reported to reduce or completely resolve a majority of lipomas, although some actually increased in size. There were side-effects, which resolved without complication. Long-term studies are deemed necessary to judge efficacy. Dr. Patrick Treacy has used phosphatidylcholine and deoxcholate successfully in the treatment of infraorbital fat pads.
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 ulcerative colitis.
Possible health risks
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Intralesional injection, termed mesotherapy, using phosphatidylcholine is a potentially effective therapy for benign symmetric lipomatosis that should be reconsidered as a therapeutic option for this disease.
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Recent laboratory investigations17 demonstrate that sodium deoxycholate, a bile salt also used as a laboratory detergent,102,103 was just as potent at causing adipocyte lysis and cell death as the complete phosphatidylcholine formula, which contains both phosphatidylcholine and deoxycholate (Figure 3). This bile salt is used to solubilize phosphatidylcholine by forming mixed micelles composed of phosphatidylcholine and deoxycholate.102,104 It is common practice to combine intravenous medications with bile salts to improve their water solubility.105,106 These findings suggest that sodium deoxycholate is the primary active ingredient in the phosphatidylchloline preparations.
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- Phosphatidylcholines at the US National Library of Medicine Medical Subject Headings (MeSH)