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 Greeklekithos (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.
Palmitoyl-oleyl-sn-phosphatidylcholine, a phosphatidylcholine derivative
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.
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 there is not enough evidence to support lecithin or phosphatidylcholine supplementation for patients with dementia. The study does admit that a moderate benefit cannot be ruled out until further large scale studies are performed.
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.
^Jackowski, Suzanne; Cronan, jr., John E.; Rock, Charles O. (1991). "Chapter 2: Lipid metabolism in procaryotes". In Vance, Dennis E.; Vance, J. Biochemistry of Lipids, Lipoproteins and Membranes. Elsevier. pp. 80–81. ISBN0-444-89321-0.
^Chen F, Zhao Q, Cai X, Lv L, Lin W, Yu X, Li C, Li Y, Xiong M, Wang XG (November 2009). "Phosphatidylcholine in membrane of Escherichia coli changes bacterial antigenicity.". Can. J. Microbiol.55 (11): 1328–34. doi:10.1139/w09-082. PMID19940943.
^Kanno K, Wu MK, Agate DA, Fanelli BK, Wagle N, Scapa EF, Ukomadu C, Cohen DE (October 2007). "Interacting proteins dictate function of the minimal START domain phosphatidylcholine transfer protein/StarD2.". J. Biol. Chem.282 (42): 30728–36. doi:10.1074/jbc.M703745200. PMID17704541.
^Mei-Chu Hung, Koji Shibasaki, Riki Yoshida, Masao Sato and Katsumi Imaizumi (2001). Learning behaviour and cerebral protein kinase C, antioxidant status, lipid composition in senescence-accelerated mouse: influence of a phosphatidylcholine–vitamin B12 diet. British Journal of Nutrition, 86, pp 163-171 doi:10.1079/BJN2001391
^Chung, Shu-Ying, Tomoe Moriyama, Eiko Uezu, Kayoko Uezu, Rieko Hirata, Noriko Yohena, Yasnunobu Masuda, Toyohiko Kokubu, and Shigeru Yamamoto. 1995. "Administration of Phosphatidylcholine Increases Brain Acetylcholine Concentration and Improves Memory in Mice with Dementia." The Journal of Nutrition 125: 1484-489. Print.
^Higgins, Julian; Leon Flicker (21 January 2009). Higgins, Julian PT, ed. "Lecithin for dementia and cognitive impairment". Cochrane Database of Systematic Reviews of Systematic Reviews4 (3): CD001015. doi:10.1002/14651858.CD001015. PMID12917896.
^Niebergall, LJ; Jacobs, RL; Chaba, T; Vance, DE (2011). "Phosphatidylcholine protects against steatosis in mice but not non-alcoholic steatohepatitis". Biochimica et Biophysica Acta1811 (12): 1177–85. doi:10.1016/j.bbalip.2011.06.021. PMID21745592.
^Sally Tandy; Rosanna WS Chung; Alvin Kamili; Elaine Wat; Jacquelyn M Weir; Peter J Meikle; Jeffrey S Cohn (30 November 2010). "Hydrogenated phosphatidylcholine supplementation reduces hepatic lipid levels in mice fed a high-fat diet". Atherosclerosis (Elsevier) 213 (1): 142–147. doi:10.1016/j.atherosclerosis.2010.07.050.
^Rotunda, Adam M.; Kolodney, Michael S. (2006). "Mesotherapy and Phosphatidylcholine Injections: Historical Clarification and Review". Dermatologic Surgery32 (4): 465–480. doi:10.1111/j.1524-4725.2006.32100.x. PMID16681654. 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.
^Park, Seung Ha; Kim, Deok Woo; Lee, Min Ah; Yoo, Sang Chul; Rhee, Seung Chul; Koo, Sang Hwan; Seol, Geun Hye; Cho, Eun Young (April 2008). "Effectiveness of Mesotherapy on Body Contouring". Plastic & Reconstructive Surgery121 (4): 179e–185e. doi:10.1097/01.prs.0000304611.71480.0a. PMID18349597. 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.'