Lipid of the Month Archive

The LIPID MAPS Lipid of the Month Archive currently lists lipids highlighted from August, 2012 - present.

2016

StigmasterolStigmasterol

Stigmasterol (stigmasta-5,22E-dien-3beta-ol) is an unsaturated phytosterol (plant sterol) occurring in the plant fats or oils of soybean, rape seed, and in a number of medicinal herbs. It differs structurally from cholesterol due to the presence of a side-chain double bond and ethyl group. Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. Phytosterols normally are broken down in the bile.


Leukotriene B4

C16-Sphingomyelin or SM(d18:1/16:0) ( systematic name: N-(hexadecanoyl)-sphing-4-enine-1-phosphocholine) is a commonly occurring member of the sphingomyelin class of sphingolipids. Sphingomyelins are present in the plasma membranes of animal cells and are especially prominent in myelin, a membranous sheath that surrounds and insulates the axons of some neurons. Sphingomyelins contain a phosphocholine polar head group attached to a ceramide backbone and resemble phosphatidylcholines in their general properties and three-dimensional structure.


Leukotriene B4

Leukotriene B4 (5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid) is a pro-inflammatory eicosanoid mediator synthesised in myeloid cells from arachidonic acid. Synthesis is catalysed by 5-lipoxygenase and leukotriene A4 hydrolase and is increased by inflammatory mediators including endotoxin, complement fragments, tumor necrosis factor and interleukins. Leukotriene B4 is able to induce the adhesion and activation of leukocytes on the endothelium, allowing them to bind to and cross it into the tissue. In neutrophils, it is also a potent chemoattractant, and is able to induce the formation of reactive oxygen species and the release of lysosomal enzymes by these cells.


ceramide.png

Chenodeoxycholic acid (3alpha,7alpha-dihydroxy-5ß-cholan-24-oic acid) is a C24 bile acid and one of the main bile acids produced by the liver. Chenodeoxycholic acid is synthesized in the liver from cholesterol and can be conjugated in the liver with taurine or glycine, forming taurochenodeoxycholic acid or glycochenodeoxycholic acid. Chenodeoxycholic acid is the most potent natural bile acid for stimulating the nuclear bile acid receptor, farnesoid X receptor. The transcription of many genes is activated by FXR.


ceramide.png

Ceramides, such as Cer(d18:1/16:0) (systematic name: N-(hexadecanoyl)-sphing-4-enine) are a class of sphingolipids composed of the long-chain base sphingosine attached to a fatty acid via an N-acyl linkage. Ceramides are found in high concentrations within the cell membrane of cells. De novo synthesis of ceramide occurs in the endoplasmic reticulum. Ceramide is subsequently transported to the Golgi apparatus by either vesicular trafficking or the ceramide transfer protein CERT. Once in the Golgi apparatus, ceramide can be further metabolized to other sphingolipids, such as sphingomyelin (a key component of cell membranes) and the complex glycosphingolipids.


Cyanidin.png

Cyanidin (2-(3,4-Dihydroxyphenyl) chromenylium-3,5,7-triol) is a polyketide metabolite belonging to the anthocyanidin subclass of flavonoids. It is a pigment found in many red berries including grapes, bilberry, blackberry and blueberry. Cyanidin, like other anthocyanidins, has putative antioxidant and radical-scavenging effects which may protect cells from oxidative damage and reduce risk of cardiovascular diseases and cancer.


oleanolic_acid.png

Oleanolic acid ((3beta-hydroxyolean-12-en-28-oic acid)) is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins. Oleanolic acid is relatively non-toxic, hepatoprotective, and exhibits antitumor and antiviral properties.


oleanolic_acid.png

Oleanolic acid ((3beta-hydroxyolean-12-en-28-oic acid)) is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins. Oleanolic acid is relatively non-toxic, hepatoprotective, and exhibits antitumor and antiviral properties.


DHA

Palmitic acid (LMFA01010001), or hexadecanoic acid, is the most common saturated fatty acid found in animals, plants and microorganisms. As its name indicates, it is a major component of the oil from palm trees (palm oil), but can also be found in meats, cheeses, butter, and dairy products. Palmitic acid is the first fatty acid produced during fatty acid synthesis and the precursor to longer chain fatty acids. Palmitic acid is used to produce soaps and cosmetics. These applications utilize sodium palmitate, which is commonly obtained by saponification of palm oil.


DHA

Docosahexaenoic acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, sperm, testicles and retina. It can be synthesized from alpha-linolenic acid or obtained directly from maternal milk or fish oil. It's systematic name is 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid. DHA is the most abundant omega-3 fatty acid in the brain and retina. DHA comprises 40% of the polyunsaturated fatty acids (PUFAs) in the brain and 60% of the PUFAs in the retina. Fifty percent of the weight of a neuron's plasma membrane is composed of DHA.


S1P

Sphingosine-1-phosphate (S1P) is an signaling sphingolipid and is composed of a C18 sphingoid base with a phosphate group at the C1 position. Phosphorylation of sphingosine to S1P is catalyzed by sphingosine kinase, an enzyme ubiquitously found in the cytosol and endoplasmatic reticulum of various types of cells. Although S1P is of importance in the entire human body, it is a major regulator of vascular and immune systems. In the vascular system, S1P regulates angioge nesis, vascular stability, and permeability. In the immune system, it is now recognized as a major regulator of trafficking of T- and B-cells.


2015

>ResolvinD2

Resolvin D2 (7S,16R,17S-trihydroxy-4Z,8E,10Z,12E,14E,19Z-docosahexaenoic acid) is a member of class of eicosanoids and docosanoids known as resolvins. Resolvins are compounds that are made by the human body from the omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). They are produced by the COX-2 pathway especially in the presence of aspirin. Experimental evidence indicates that resolvins reduce cellular inflammation by inhibiting the production and transportation of inflammatory cells and chemicals to the sites of inflammation.


>Taurocholic aci

Taurocholic acid ,(N-(3alpha,73alpha,123alpha-trihydroxy-5beta-cholan-24-oyl)-taurine), known also as cholyltaurine, is a bile acid conjugate involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with taurine.


OPDA

12-oxo Phytodienoic acid (OPDA) or 12-oxo-PDA LMFA02010001 is an octadecanoid and a biologically active, immediate precursor of 7-epi jasmonic acid. In addition to its link with jasmonic acid activity, OPDA appears to play an independent role in mediating resistance to pathogens and pests.


Geranial.png

Geranial, or 3,7-dimethyl-2E,6-octadienal is a monoterpenoid with the molecular formula C10H16O. The two compounds are double bond isomers. The 2E-isomer is also called citral A. The 2Z-isomer is known as neral or citral B. Geranial is present in the oils of several plants, including limes, lemons and oranges and has a strong lemon odor. It also has strong antimicrobial qualities and pheromonal effects in insects.


Mayolene-16

Mayolene-16 or 11R-hexadecanoyloxyoctadeca-9Z,12Z,15Z-trienoic acid is a member of a class of fatty esters (mayolenes) found in the larvae of the European cabbage butterfly, Pieris rapae. They are composed of esters between straight-chain fatty acids and 11-hydroxy alpha-linolenic acid. The mayolenes have been shown to act as potent chemical deterrents to larval predators such as ants.


Myristoleic acid

Myristoleic acid, or 9Z-tetradecenoic acid, is an omega-5 fatty acid. It is biosynthesized from myristic acid by the enzyme delta-9 desaturase, but it is uncommon in nature. One of the major sources of this fatty acid is the seed oil from plants of the family Myristicaceae, comprising up to 30 per cent of the oil in some species.


Prostaglandin

Prostaglandin D2 (or PGD2) is a prostaglandin that binds to the receptor PTGDR, as well as CRTH2. It is a major prostaglandin produced by mast cells and recruits Th2 cells, eosinophils, and basophils. In mammalian organs, large amounts of PGD2 are found only in the brain and in mast cells. It is critical to development of allergic diseases such as asthma. Cellular synthesis occurs through the arachidonic acid cascade with the final conversion from PGH2 performed by PGD2 synthase (PTGDS).



Lauric acid
Lauric acid, or dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain. Lauric acid, as a component of triglycerides, comprises about half of the fatty acid content in coconut oil, laurel oil, and palm kernel oil. It is also found in human breast milk (6.2% of total fat), cow's milk and goat's milk. Industrially, it is mainly used for the production of soaps and cosmetics.


Lithocholic acid
Lithocholic acid, or 3alpha-hydroxy-5beta-cholan-24-oic acid is a monohydroxy secondary bile acid that acts as a detergent to solubilize fats for absorption. Bacterial action in the colon produces lithocholic acid from chenodeoxycholic acid by reduction of the C7 hydroxyl group in the B ring. Lithocholic acid can activate the vitamin D receptor without raising calcium levels as much as vitamin D itself.


Aldosterone
Aldosterone (LMST02030026) is a steroid hormone of the mineralocorticoid family synthesized from cholesterol in the adrenal gland. It plays a central role in the regulation of blood pressure, mainly by acting on the distal tubules and collecting ducts of the nephron, increasing reabsorption of ions and water. When dysregulated, aldosterone is pathogenic and contributes to the development and progression of cardiovascular and renal disease. Aldosterone is part of the renin-angiotensin system and tends to promote Na+ and water retention, and lower plasma K+ concentration.



Jasmonic Acid
Jasmonic Acid (LMFA02020001), is a C12 fatty acid which is is biosynthesized from linolenic acid by the octadecanoid pathway. It is a plant growth regulator involved in the signaling mechanisms for a variety of conditions including plant defense, wound healing, tuberization, fruit ripening, and senescence Jasmonic acid is also converted to a variety of derivatives including esters such as methyl jasmonate and may also be conjugated to amino acids.



Chenodeoxycholic Acid
Chenodeoxycholic Acid (LMST04010032), along with cholic acid, is one of two primary bile acids found in humans. Chenodeoxycholic Acid is synthesized in the liver from cholesterol. It is known to aid digestion and can be used to dissolve gallstones and in the treatment of cerebral cholesterosis.


2014


Cyanidin
Cyanidin (LMPK12010002) is a flavonoid polyketide pigment with a characteristic reddish-purple color found in many red berries including but not limited to grapes, blackberry, blueberry, cherry, cranberry, and raspberry. Cyanidin, like other anthocyanidins, has putative antioxidant and radical-scavenging effects which may protect cells from oxidative damage and reduce risk of cardiovascular diseases and cancer.



Ergosterol
Ergosterol (ergosta-5,7,22E-trien-3beta-ol) is a sterol found in cell membranes of fungi and protozoa, serving many of the same functions that cholesterol serves in animal cells. Like cholesterol and in contrast to the plant sterols, it is synthesised via lanosterol as the key intermediate. Some antifungal drugs are targeted against ergosterol biosynthesis. Ergosterol is the provitamin form of vitamin D2; exposure to ultraviolet (UV) light causes a chemical reaction that produces vitamin D2.



Germacrene A
Germacrene A is a cyclic sesquiterpene (C15 prenol). Germacrenes are typically produced in a number of plant species for their antimicrobial and insecticidal properties, though they also play a role as insect pheromones.



margaric acid
Margaric acid (LMFA01010017) or heptadecanoic acid is a straight-chain saturated fatty acid. It occurs as a trace component of the fat and milkfat of ruminants, but it does not occur in any natural animal or vegetable fat at high concentrations. It has been reported as a constituent of various fungi and lichens.



(22,23-methylene-23,24-dimethylcholest-5-en-3ß-ol or gorgost-5-en-3ß-ol)
Gorgosterol (22,23-methylene-23,24-dimethylcholest-5-en-3ß-ol or gorgost-5-en-3ß-ol) is a sterol with a gorgostane skelton characterized by a cyclopropyl group at C22,C23 on the side-chain. This sterol, its hydrogenated counterpart gorgostanol and 4-methylated analogues have been reported in a number of marine invertebrates, dinoflagellates and organisms that prey on these species.



Spisulosine
Spisulosine (1-deoxy-sphinganine) is a sphingoid base analog of sphinganine where the C1-hydroxyl group is absent and therefore cannot be metabolized to complex sphingolipids nor degraded by the regular sphingolipid catabolism pathway. It is biosynthesized by Serine Palmitoyltransferase (SPT) from palmitoyl-CoA and alanine, where alanine replaces serine as the amino-acid substrate. Inhibition of ceramide synthases by the mycotoxin Fumonisin B causes accumulation of 1-deoxysphinganine, leading to kidney and liver toxicity and other diseases.



Spisulosine
Spisulosine (1-deoxy-sphinganine) is a sphingoid base analog of sphinganine where the C1-hydroxyl group is absent and therefore cannot be metabolized to complex sphingolipids nor degraded by the regular sphingolipid catabolism pathway. It is biosynthesized by Serine Palmitoyltransferase (SPT) from palmitoyl-CoA and alanine, where alanine replaces serine as the amino-acid substrate. Inhibition of ceramide synthases by the mycotoxin Fumonisin B causes accumulation of 1-deoxysphinganine, leading to kidney and liver toxicity and other diseases.



Lipoxin A4
Lipoxin A4 (5S,6R,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid) is a member of the lipoxin family which are derived enzymatically from arachidonic acid, an w-6 fatty acid. They have a number of immunomodulatory and anti-inflammatory actions. Lipoxins are short lived endogenously produced nonclassic eicosanoids whose appearance in inflammation signals the resolution of inflammation.



Glucuronosyldiacylglycerol Glucuronosyldiacylglycerol (GlcADG) Glycosyl diacylglycerols are ubiquitous membranous components of higher plants and Gram-positive bacteria. Bacterial glucuronosyldiacylglycerols have been shown to have highly antigenic properties and have been reported to be essential for protection against phosphorus depletion in the plant Arabidopsis thaliana




Taurocholic acid (N-(3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oyl)-taurine), is a bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with taurine.


2013


PGF2α
Sphingosine is long-chain aliphatic amine which provides the structural backbone of several classes of sphingolipids including ceramides, sphingomeylins, gangliosides and various glycosphingolipids. Sphingosine plays a role in cellular apoptosis and is believed to have a signalling role in plants by controlling pH gradients across membranes. In animals, free sphingosine is produced by the action of ceramidases, which hydrolze ceramides to sphingosine and free fatty acids.



Cholic acid
Cholic acid or 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.



PGF2α
Prostaglandin F2α (PGF2α), is a naturally occurring prostaglandin used in medicine to induce labor. It stimulates the contraction of uterine and bronchial smooth muscle and produces vasoconstriction in some blood vessels.



Desmosterol
Desmosterol is a direct precursor of cholesterol and contains a double bond at C24 which is reduced by the enzyme DHCR24. Desmosterol has recently been shown to play an important role in cholesterol homeostasis and modulation of inflammation in macrophages (http://dx.doi.org/10.1016/j.cell.2012.06.054).



Colneleic acid
Colneleic acid is a divinyl ether-containing fatty acid produced from 9S-hydroperoxy-10E,12Z-octadecadienoic acid. Colneleic acid and the related colnelenic acid are found in leaves of potato plants infected by fungi or viruses, and they are believed to play a defensive role against potato blight.



TXA

Thromboxane A2 (TXA2) is an eicosanoid that is generated from prostaglandin H2 by the enzyme thromboxane-A synthase. It is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation. TXA2 is very unstable and is rapidly hydrolyzed to the biologically inactive thromboxane B2.


Psychosine

Psychosine (Galactosylsphingosine) is a basic glycosphingolipid present in low concentrations in animal cells. It consists of sphingosine having a beta-D-galactosyl residue attached at the C1-position. Psychosine accumulates in tissues in the genetic disorder Krabbe disease which is caused by a deficiency of the enzyme beta-galactosylceramidase.



Isopentenyl pyrophosphate (IPP)

Isopentenyl pyrophosphate (IPP) Isopentenyl pyrophosphate (IPP) is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of sterols and prenols. IPP is formed from acetyl-CoA via mevalonic acid. IPP can then be isomerized to dimethylallyl pyrophosphate by the enzyme isopentenyl pyrophosphate isomerase.



Prostaglandin E2 (PGE2)

Prostaglandin E2 (PGE2) Prostaglandin E2 (PGE2) is one of a group of hormone-like substances that participate in a wide range of body functions such as the contraction and relaxation of smooth muscle, the dilation and constriction of blood vessels, control of blood pressure, and modulation of inflammation. PGE2 is released by blood vessel walls in response to infection or inflammation that acts on the brain to induce fever.


Sphingosine-1-phosphate (S1P)

Sphingosine-1-phosphate (S1P) is a signaling sphingolipid derived from ceramide that is synthesized de novo or as part of the sphingomyelin cycle in animal cells. It exerts its biological effects by interacting with cell surface receptors. Although S1P is of importance in the entire human body, it is a major regulator of vascular and immune systems and is also involved in cardiac function, inflammation, cancer and Alzheimer's disease.


2012

lanosterol

Jasmonic acid (JA) is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway. The major function of jasmonic acid and its various metabolites is regulating plant responses to abiotic and biotic stresses as well as plant growth and development.


lanosterol

Lanosterol (lanosta-8,24-dien-3beta-ol) is the first cyclic intermediate in the cholesterol biosynthetic pathway and is produced by the cyclization of the triterpene (3S)-squalene-2,3-epoxide catalyzed by the enzyme lanosterol synthase.


Arachidyl linoleate

Arachidyl linoleate is an example of a wax ester.
Wax esters (WEs), lipids composed of long-chain fatty alcohols esterified to long-chain fatty acids, are widespread in nature. They serve a variety of functions in living organisms, including surface protection, energy storage and chemical communication.


PAPC

1-palmitoyl-2-arachidonoyl -sn- phosphatidylcholine (PAPC)
is a naturally occuring phospholipid containing palmitic acid and arachidonic acid, which is common in mammalian cell membranes and lipoproteins. PAPC is used as an unoxidized control in experiments utilizing oxidized PAPC (OxPAPC).


Arachidonic Acid

Arachidonic Acid
Also known as "arachidonate", this polyunsaturated omega-6 fatty acid found in fatty meats, egg yolks, certain varieties of fish, and human breast milk plays important roles in muscle growth, brain function, and mental health.



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