Lysophosphatidylcholine

Lysophosphatidylcholines (LPC, lysoPC), also called lysolecithins, are a class of chemical compounds which are derived from phosphatidylcholines.[1]

General chemical structure of lysophosphatidylcholines, where R is a variable fatty acid chain

Overview

They result from partial hydrolysis of phosphatidylcholines, which removes one of the fatty acid groups. The hydrolysis is generally the result of the enzymatic action of phospholipase A2.[2] Among other properties, they activate endothelial cells during early atherosclerosis[3][4] and stimulate phagocyte recruitment when released by apoptotic cells.[5] Moreover, LPCs can be used in the lab to cause demyelination of brain slices, to mimic the effects of demyelinating diseases such as multiple sclerosis. Further, they are known to stimulate phagocytosis of the myelin sheath and can change the surface properties of erythrocytes.[6] LPC-induced demyelination is thought to occur through the actions of recruited macrophages and microglia which phagocytose nearby myelin. Invading T cells are also thought to mediate this process. Bacteria such as Legionella pneumophila utilize phospholipase A2 end-products (fatty acids and lysophospholipids) to cause host cell (macrophage) apoptosis through cytochrome C release.

LPCs are present as minor phospholipids in the cell membrane (≤ 3%) and in the blood plasma (8–12%).[6] Since LPCs are quickly metabolized by lysophospholipase and LPC-acyltransferase, they last only shortly in vivo. By replacing the acyl-group within the LPC with an alkyl-group, alkyl-lysophospholipids (ALP) were synthesized. These LPC analogues are metabolically stable, and several such as edelfosine, miltefosine and perifosine are under research and development as drugs against cancer and other diseases.[6][7] Lysophosphatidylcholine processing has been discovered to be an essential component of normal human brain development: those born with genes that prevent adequate uptake suffer from lethal microcephaly.[8]

LPCs occur in many foods naturally. In Starch: Chemistry and Technology third edition on page 592, the authors state that "lysophosphatidylcholine makes up about 70% of the lipids in oat starch".[9]

The anti-cancer abilities of synthetic LPC variants are special since they do not target the cell DNA but insert into the plasma membrane and cause apoptosis through influencing several signal pathways. Therefore, their effects are independent of the proliferation state of the tumor cell.[10]

Industrial Applications of Enzymes Producing Lysophosphatidylcholine

FoodPro LysoMaxa Oil is an FDA approved commercialized PLA2 enzyme preparation utilized for the degumming of vegetable oils in large-scale productions to increase yield. Variants of lysophosphatidylcholine are the main products of this enzyme. [11] Lysophosphatidylcholine has been studied as an immune activator for differentiating monocytes to mature dendritic cells.[12] Lysophosphatidylcholine present in blood amplifies microbial TLR ligands induced inflammatory responses from human cells like intestinal epithelial cells and macrophages/monocytes [13].This has an implication in sepsis induced by microbes.

Composition in Foods

Lysophosphatidylcholine accounts for 4.6% of phospholipids found in coconut oil, which make up 0.2% of lipids in coconut oil. This is compared to vegetable oils, which may contain 2-3% phospholipids.[14]