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Phosphatidylcholine

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.http://lipidlibrary.aocs.org/Lipids/pc/index.htm Phospholipase D catalyzes the hydrolysis of phosphatidylcholine to form phosphatidic acid (PA), releasing the soluble choline headgroup into the cytosol. 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.Tayebeh Jadidi et al 2013 1|Europhysics Letters 102 28008

Possible health benefits

Senescence

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.

Liver repair

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.{{cite journal | title = Hydrogenated phosphatidylcholine supplementation reduces hepatic lipid levels in mice fed a high-fat diet | journal = Atherosclerosis | date = 30 November 2010 | author1 = Sally Tandy | author2 = Rosanna WS Chung | author3= Alvin Kamili | author4= Elaine Wat | author5= Jacquelyn M Weir | author6= Peter J Meikle | author7= Jeffrey S Cohn | volume = 213 | pages = 142–147 | doi = 10.1016/j.atherosclerosis.2010.07.050 | issue = 1 | publisher = Elsevier | pmid=20832797 }}

Lipolysis

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,{{cite journal | last1 = Hasegawa | first1 = Toshio | last2 = Matsukura | first2 = Tomoyuki | last3 = Ikeda | first3 = Shigaku | title = Mesotherapy for Benign Symmetric Lipomatosis | journal = Aesthetic Plastic Surgery | year = 2010 | volume = 34 | issue = 2 | pages = 153–156 | pmid = 19488808 | doi = 10.1007/s00266-009-9374-4 | url=http://www.springerlink.com/content/pn55k77954un9217/ | quote = 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. }} no peer-reviewed studies have shown any amount of lipolysis even remotely comparable to liposuction.{{cite journal | last1 = Park | first1 = Seung Ha | last2 = Kim | first2 = Deok Woo | last3 = Lee | first3 = Min Ah | last4 = Yoo | first4 = Sang Chul | last5 = Rhee | first5 = Seung Chul | last6 = Koo | first6 = Sang Hwan | last7 = Seol | first7 = Geun Hye | last8 = Cho | first8 = Eun Young | title = Effectiveness of Mesotherapy on Body Contouring | journal = Plastic & Reconstructive Surgery | date = April 2008 | volume = 121 | issue = 4 | pages = 179e–185e | pmid = 18349597 | doi = 10.1097/01.prs.0000304611.71480.0a | quote = The author, when discussing phosphatidylcholine as a part of mesotherapy concludes: 'Although there is a preliminary report contradictory to this result, there was no body contouring observed in this study. There were no statistically significant changes in thigh girth, cross-sectional area, or laboratory values for the lipid profile except for a decrease in the triglyceride level in the blood, which might be an indirect effect of the method of aminophylline absorption into the systemic circulation.' }} 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.Amber KT, Ovadia S, Camacho I (2014) Injection therapy for the management of superficial subcutaneous lipomas. J Clin Aesthet Dermatol 7 (6):46-8. PMID: 25013540 Dr. Patrick Treacy has used phosphatidylcholine and deoxcholate successfully in the treatment of infraorbital fat pads.

Ulcerative colitis

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

A report in 2011 has linked the microbial catabolites of phosphatidylcholine with increased atherosclerosis in mice through the production of choline, trimethylamine oxide, and betaine.

See also

Additional images

Image:Phosphatidylcholine.jpg|General structural formula of phosphatidylcholines Image:Membrane lipids.png| Membrane lipids Image:Choline metabolism-en.svg|Choline metabolism Image:Phosphatidate2.png| Phosphatidate Image:Choline-skeletal.png| Choline

References

External links

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"green air" © 2007 - Ingo Malchow, Webdesign Neustrelitz
This article based upon the http://en.wikipedia.org/wiki/Phosphatidylcholine, the free encyclopaedia Wikipedia and is licensed under the GNU Free Documentation License.
Further informations available on the list of authors and history: http://en.wikipedia.org/w/index.php?title=Phosphatidylcholine&action=history
presented by: Ingo Malchow, Mirower Bogen 22, 17235 Neustrelitz, Germany