Lipid - Knowledge

7256: 1257: 5791: 5748: 3624: 2143: 787: 603: 688: 395: 22: 974: 8830: 854: 414: 8818: 1249:(mainly cholesterol in animal cell membranes) are also found in biological membranes. In plants and algae, the galactosyldiacylglycerols, and sulfoquinovosyldiacylglycerol, which lack a phosphate group, are important components of membranes of chloroplasts and related organelles and are among the most abundant lipids in photosynthetic tissues, including those of higher plants, algae and certain bacteria. 1053: 1327:. Micelles and bilayers form in the polar medium by a process known as the hydrophobic effect. When dissolving a lipophilic or amphiphilic substance in a polar environment, the polar molecules (i.e., water in an aqueous solution) become more ordered around the dissolved lipophilic substance, since the polar molecules cannot form 1725:. Hence the citric acid cycle can start at acetyl-CoA when fat is being broken down for energy if there is little or no glucose available. The energy yield of the complete oxidation of the fatty acid palmitate is 106 ATP. Unsaturated and odd-chain fatty acids require additional enzymatic steps for degradation. 1831:

A few studies have suggested that total dietary fat intake is linked to an increased risk of obesity. and diabetes; Others, including the Women's Health Initiative Dietary Modification Trial, an eight-year study of 49,000 women, the Nurses' Health Study, and the Health Professionals Follow-up Study,

717:. Neural tissue (including the brain) contains relatively high amounts of glycerophospholipids, and alterations in their composition has been implicated in various neurological disorders. Glycerophospholipids may be subdivided into distinct classes, based on the nature of the polar headgroup at the 1252:

Plant thylakoid membranes have the largest lipid component of a non-bilayer forming monogalactosyl diglyceride (MGDG), and little phospholipids; despite this unique lipid composition, chloroplast thylakoid membranes have been shown to contain a dynamic lipid-bilayer matrix as revealed by magnetic

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The major dietary lipids for humans and other animals are animal and plant triglycerides, sterols, and membrane phospholipids. The process of lipid metabolism synthesizes and degrades the lipid stores and produces the structural and functional lipids characteristic of individual tissues.

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despite environmental low-temperatures, and also makes linolenic acid give dominating sharp peaks in high resolution 13-C NMR spectra of chloroplasts. This in turn plays an important role in the structure and function of cell membranes. Most naturally occurring fatty acids are of the

650:. The word "triacylglycerol" is sometimes used synonymously with "triglyceride". In these compounds, the three hydroxyl groups of glycerol are each esterified, typically by different fatty acids. Because they function as an energy store, these lipids comprise the bulk of storage 5761:

Howard BV, Manson JE, Stefanick ML, Beresford SA, Frank G, Jones B, Rodabough RJ, Snetselaar L, Thomson C, Tinker L, Vitolins M, Prentice R (January 2006). "Low-fat dietary pattern and weight change over 7 years: the Women's Health Initiative Dietary Modification Trial".

1813:. Many studies have shown positive health benefits associated with consumption of omega-3 fatty acids on infant development, cancer, cardiovascular diseases, and various mental illnesses (such as depression, attention-deficit hyperactivity disorder, and dementia). 1458:

which place them exclusively on the cytosolic side and the activation of scramblases, which scramble the orientation of the phospholipids. After this occurs, other cells recognize the phosphatidylserines and phagocytosize the cells or cell fragments exposing them.

1685:. For the most part, fatty acids are oxidized by a mechanism that is similar to, but not identical with, a reversal of the process of fatty acid synthesis. That is, two-carbon fragments are removed sequentially from the carboxyl end of the acid after steps of 471:

in water. The fatty acid structure is one of the most fundamental categories of biological lipids and is commonly used as a building-block of more structurally complex lipids. The carbon chain, typically between four and 24 carbons long, may be saturated or

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revealed no such links. None of these studies suggested any connection between percentage of calories from fat and risk of cancer, heart disease, or weight gain. The Nutrition Source, a website maintained by the department of nutrition at the

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Beresford SA, Johnson KC, Ritenbaugh C, Lasser NL, Snetselaar LG, Black HR, et al. (February 2006). "Low-fat dietary pattern and risk of colorectal cancer: the Women's Health Initiative Randomized Controlled Dietary Modification Trial".

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proposed the substitution of "lipoid" by "lipin". In 1920, Bloor introduced a new classification for "lipoids": simple lipoids (greases and waxes), compound lipoids (phospholipoids and glycolipoids), and the derived lipoids (fatty acids,

1454:. Phosphatidylserine lipids are known to be involved in signaling for the phagocytosis of apoptotic cells or pieces of cells. They accomplish this by being exposed to the extracellular face of the cell membrane after the inactivation of 569:

is also important in biological systems, particularly with respect to sight. Other major lipid classes in the fatty acid category are the fatty esters and fatty amides. Fatty esters include important biochemical intermediates such as

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Triglycerides, stored in adipose tissue, are a major form of energy storage both in animals and plants. They are a major source of energy in aerobic respiration. The complete oxidation of fatty acids releases about 38 kJ/g

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are a subclass of glycerophospholipids containing four acyl chains and three glycerol groups that are particularly abundant in the inner mitochondrial membrane. They are believed to activate enzymes involved with

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group. The enzymes of fatty acid biosynthesis are divided into two groups, in animals and fungi all these fatty acid synthase reactions are carried out by a single multifunctional protein, while in plant

1840:, summarizes the current evidence on the effect of dietary fat: "Detailed research—much of it done at Harvard—shows that the total amount of fat in the diet isn't really linked with weight or disease." 1295:. In an aqueous system, the polar heads of lipids align towards the polar, aqueous environment, while the hydrophobic tails minimize their contact with water and tend to cluster together, forming a 6797: 6791: 1499:

across membranes. Polyprenol phosphate sugars and polyprenol diphosphate sugars function in extra-cytoplasmic glycosylation reactions, in extracellular polysaccharide biosynthesis (for instance,

756:(PS or GPSer). In addition to serving as a primary component of cellular membranes and binding sites for intra- and intercellular proteins, some glycerophospholipids in eukaryotic cells, such as 4741:

Indiveri C, Tonazzi A, Palmieri F (October 1991). "Characterization of the unidirectional transport of carnitine catalyzed by the reconstituted carnitine carrier from rat liver mitochondria".

6017:– Professional medical education organization for health care professionals who seek to prevent morbidity and mortality stemming from dyslipidemias and other cholesterol-related disorders. 6737: 3006:

Farooqui AA, Horrocks LA, Farooqui T (June 2000). "Glycerophospholipids in brain: their metabolism, incorporation into membranes, functions, and involvement in neurological disorders".

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molecules (containing both hydrophobic and hydrophilic regions) that contain a glycerol core linked to two fatty acid-derived "tails" by ester linkages and to one "head" group by a

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Most of the fat found in food is in the form of triglycerides, cholesterol, and phospholipids. Some dietary fat is necessary to facilitate absorption of fat-soluble vitamins (

1000:(MVA) pathway. The simple isoprenoids (linear alcohols, diphosphates, etc.) are formed by the successive addition of C5 units, and are classified according to number of these 1549:

that polymerize and then reduce acetyl-CoA units. The acyl chains in the fatty acids are extended by a cycle of reactions that add the acetyl group, reduce it to an alcohol,

1371:, or fat cell, is designed for continuous synthesis and breakdown of triglycerides in animals, with breakdown controlled mainly by the activation of hormone-sensitive enzyme 7000: 6856: 6719: 4575:"Mechanism of nuclear calcium signaling by inositol 1,4,5-trisphosphate produced in the nucleus, nuclear located protein kinase C and cyclic AMP-dependent protein kinase" 1533:

In animals, when there is an oversupply of dietary carbohydrate, the excess carbohydrate is converted to triglycerides. This involves the synthesis of fatty acids from

8532: 7053: 6707: 6658: 6652: 2391:"Suggestion to teachers of biochemistry. I. A proposed chemical classification of lipins, with a note on the intimate relation between cholesterols and bile salts" 6713: 4690:

Biermann M, Maueröder C, Brauner JM, Chaurio R, Janko C, Herrmann M, Muñoz LE (December 2013). "Surface code--biophysical signals for apoptotic cell clearance".

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Fatty acyls, a generic term for describing fatty acids, their conjugates and derivatives, are a diverse group of molecules synthesized by chain-elongation of an

4229:"Thematic review series: adipocyte biology. The perilipin family of structural lipid droplet proteins: stabilization of lipid droplets and control of lipolysis" 1083:

describe compounds in which fatty acids are linked to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a

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recognized fat ("oily" alimentary matters), along with protein ("albuminous") and carbohydrate ("saccharine"), as an important nutrient for humans and animals.

150:, or membranes in an aqueous environment. Biological lipids originate entirely or in part from two distinct types of biochemical subunits or "building-blocks": 6927: 6887: 6881: 6822: 6695: 4495:

Hinkovska-Galcheva V, VanWay SM, Shanley TP, Kunkel RG (November 2008). "The role of sphingosine-1-phosphate and ceramide-1-phosphate in calcium homeostasis".

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Ivanova PT, Milne SB, Byrne MO, Xiang Y, Brown HA (2007). "Glycerophospholipid identification and quantitation by electrospray ionization mass spectrometry".

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and its derivatives, are an important component of membrane lipids, along with the glycerophospholipids and sphingomyelins. Other examples of sterols are the

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Lees ND, Skaggs B, Kirsch DR, Bard M (March 1995). "Cloning of the late genes in the ergosterol biosynthetic pathway of Saccharomyces cerevisiae--a review".

1901: – Class of organic compounds, a class of natural products composed of long aliphatic chains and phenolic rings that occur in plants, fungi and bacteria 921:, at position 3 in the carbon chain. They have in common with steroids the same fused four-ring core structure. Steroids have different biological roles as 6808: 5598:

Astrup A, Dyerberg J, Selleck M, Stender S (2008), "Nutrition transition and its relationship to the development of obesity and related chronic diseases",

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Eyster KM (March 2007). "The membrane and lipids as integral participants in signal transduction: lipid signal transduction for the non-lipid biochemist".

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and bacteria separate enzymes perform each step in the pathway. The fatty acids may be subsequently converted to triglycerides that are packaged in

1407:, a sphingolipid derived from ceramide that is a potent messenger molecule involved in regulating calcium mobilization, cell growth, and apoptosis; 515:-double bonds cause the fatty acid chain to bend, an effect that is compounded with more double bonds in the chain. Three double bonds in 18-carbon 7162: 5366:

Russo GL (March 2009). "Dietary n-6 and n-3 polyunsaturated fatty acids: from biochemistry to clinical implications in cardiovascular prevention".

768:. Typically, one or both of these hydroxyl groups are acylated with long-chain fatty acids, but there are also alkyl-linked and 1Z-alkenyl-linked ( 3118: 7506: 1612:

by metabolic pathways in which acyl groups in fatty acyl-CoAs are transferred to the hydroxyl groups of glycerol-3-phosphate and diacylglycerol.

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For a century, chemists regarded "fats" as only simple lipids made of fatty acids and glycerol (glycerides), but new forms were described later.

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and their conjugates, which in mammals are oxidized derivatives of cholesterol and are synthesized in the liver. The plant equivalents are the

341:. Bertrand included in the concept not only the traditional fats (glycerides), but also the "lipoids", with a complex constitution. The word 3336:

Villinski JC, Hayes JM, Brassell SC, Riggert VL, Dunbar R (2008). "Sedimentary sterols as biogeochemical indicators in the Southern Ocean".

8248: 2345:"On the ultimate composition of simple alimentary substances, with some preliminary remarks on the analysis of organised bodies in general" 1087:

substitutes for the glycerol backbone present in glycerolipids and glycerophospholipids. The most familiar saccharolipids are the acylated

829:(ceramide phosphocholines), whereas insects contain mainly ceramide phosphoethanolamines and fungi have phytoceramide phosphoinositols and 3871:

Lyu, Jiabao; Gao, Renjun; Guo, Zheng (2021). "Galactosyldiacylglycerols: From a photosynthesis-associated apparatus to structure-defined

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Honke K, Zhang Y, Cheng X, Kotani N, Taniguchi N (2004). "Biological roles of sulfoglycolipids and pathophysiology of their deficiency".

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developed a more detailed classification, including oils, greases, tallow, waxes, resins, balsams and volatile oils (or essential oils).

6011:– Provides dyslipidemia and cardiovascular disease prevention and treatment information as well as continuing medical education programs 5528:

Dalainas I, Ioannou HP (April 2008). "The role of trans fatty acids in atherosclerosis, cardiovascular disease and infant development".

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Comptes rendus hebdomadaires des séances de l'Académie des Sciences, Paris, 1853, 36, 27; Annales de Chimie et de Physique 1854, 41, 216

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ester linkage. While glycerophospholipids are the major component of biological membranes, other non-glyceride lipid components such as

182:(derived from condensation of ketoacyl subunits); and sterol lipids and prenol lipids (derived from condensation of isoprene subunits). 7713: 5401:

Riediger ND, Othman RA, Suh M, Moghadasian MH (April 2009). "A systemic review of the roles of n-3 fatty acids in health and disease".

1765:(an omega-3 fatty acid) because they cannot be synthesized from simple precursors in the diet. Both of these fatty acids are 18-carbon 669:. Examples of structures in this category are the digalactosyldiacylglycerols found in plant membranes and seminolipid from mammalian 5020: 1117:-Lipid A, a hexa-acylated disaccharide of glucosamine that is glycosylated with two 3-deoxy-D-manno-octulosonic acid (Kdo) residues. 1107:

of glucosamine, which are derivatized with as many as seven fatty-acyl chains. The minimal lipopolysaccharide required for growth in

833:-containing headgroups. The glycosphingolipids are a diverse family of molecules composed of one or more sugar residues linked via a 661:

Additional subclasses of glycerolipids are represented by glycosylglycerols, which are characterized by the presence of one or more

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Galli C, Risé P (2009). "Fish consumption, omega 3 fatty acids and cardiovascular disease. The science and the clinical trials".

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Fezza F, De Simone C, Amadio D, Maccarrone M (2008). "Fatty Acid Amide Hydrolase: A Gate-Keeper of the Endocannabinoid System".

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Bouillon R, Verstuyf A, Mathieu C, Van Cromphaut S, Masuyama R, Dehaes P, Carmeliet G (December 2006). "Vitamin D resistance".

822:-linked fatty acid. The fatty acids are typically saturated or mono-unsaturated with chain lengths from 16 to 26 carbon atoms. 814:, phosphosphingolipids, glycosphingolipids and other compounds. The major sphingoid base of mammals is commonly referred to as 209:

both to break down and to synthesize lipids, some essential lipids cannot be made this way and must be obtained from the diet.

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Parodi AJ, Leloir LF (April 1979). "The role of lipid intermediates in the glycosylation of proteins in the eucaryotic cell".

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Fahy E, Subramaniam S, Murphy RC, Nishijima M, Raetz CR, Shimizu T, Spener F, van Meer G, Wakelam MJ, Dennis EA (April 2009).

1828:. Fats that are good for one may be turned into trans fats by improper cooking methods that result in overcooking the lipids. 8855: 7703: 7695: 7687: 6413: 5930: 5909: 5888: 5869: 5850: 5350: 4539: 4155: 3859: 3380: 3133: 3058: 2832: 2759: 2650: 2583: 2552: 2527: 2313: 2167: 1971: 1927: 317:

The terms lipoid, lipin, lipide and lipid have been used with varied meanings from author to author. In 1912, Rosenbloom and

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Mozaffarian D, Willett WC (December 2007). "Trans fatty acids and cardiovascular risk: a unique cardiometabolic imprint?".

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oils). Alpha-linolenic acid is found in the green leaves of plants and in some seeds, nuts, and legumes (in particular

1487:-based lipids – are essential nutrients stored in the liver and fatty tissues, with a diverse range of functions. 654:

in animal tissues. The hydrolysis of the ester bonds of triglycerides and the release of glycerol and fatty acids from

1495:. Polyprenols and their phosphorylated derivatives also play important transport roles, in this case the transport of 7396: 1581:

reaction, whereby a double bond is introduced into the fatty acyl chain. For example, in humans, the desaturation of

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Hunter JE (November 2006). "Dietary trans fatty acids: review of recent human studies and food industry responses".

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Lichtenthaler HK (June 1999). "The 1-dideoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants".

3690:"Biosynthetic engineering of polyene macrolides towards generation of improved antifungal and antiparasitic agents" 3506:

Brunmark A, Cadenas E (1989). "Redox and addition chemistry of quinoid compounds and its biological implications".

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subunits by classic enzymes as well as iterative and multimodular enzymes that share mechanistic features with the

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Saddoughi SA, Song P, Ogretmen B (2008). "Roles of Bioactive Sphingolipids in Cancer Biology and Therapeutics".

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Malinauskas T (March 2008). "Docking of fatty acids into the WIF domain of the human Wnt inhibitory factor-1".

1300: 1040:) in which the terminal isoprenoid unit attached to oxygen remains unsaturated, whereas in animal polyprenols ( 8320: 5173:"Methanocaldococcus jannaschii uses a modified mevalonate pathway for biosynthesis of isopentenyl diphosphate" 1331:

to the lipophilic areas of the amphiphile. So in an aqueous environment, the water molecules form an ordered "

8646: 7406: 7388: 5823:"Fats and Cholesterol: Out with the Bad, In with the Good — What Should You Eat? – The Nutrition Source" 1893: 1225:

and the intracellular membranes of organelles; in animal cells, the plasma membrane physically separates the

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Yashroy RC (1990). "Magnetic resonance studies of dynamic organisation of lipids in chloroplast membranes".

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Hölzl G, Dörmann P (September 2007). "Structure and function of glycoglycerolipids in plants and bacteria".

8713: 7205: 4105:"Nonpolar solutes enhance water structure within hydration shells while reducing interactions between them" 1491:

are involved in the transport and metabolism of fatty acids in and out of mitochondria, where they undergo

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Although the term "lipid" is sometimes used as a synonym for fats, fats are a subgroup of lipids called

8808: 8153: 7740: 6085: 6080: 4969: 1879: – large scale study of an organism's lipid metabolism using high-end chemical analysis techniques 1647: 1392: 1375:. Migratory birds that must fly long distances without eating use triglycerides to fuel their flights. 6933: 3637:

Walsh CT (March 2004). "Polyketide and nonribosomal peptide antibiotics: modularity and versatility".

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Subramaniam S, Fahy E, Gupta S, Sud M, Byrnes RW, Cotter D, Dinasarapu AR, Maurya MR (October 2011).

1627: 1586: 1513: 993: 5790: 5747: 3623: 2142: 1399:, and members of several different lipid categories have been identified as signaling molecules and 1145:

from animal, plant, bacterial, fungal and marine sources, and have great structural diversity. Many

234: 8537: 8258: 8199: 8105: 7617: 7240: 6319: 1849: 1722: 1626:, are made by the assembly and modification of isoprene units donated from the reactive precursors 1488: 1182: 749: 691: 365: 3541:

Swiezewska E, Danikiewicz W (July 2005). "Polyisoprenoids: structure, biosynthesis and function".

2929: 2390: 1443:, which modulate a host of functions such as reproduction, metabolism and blood pressure; and the 8706: 8631: 8380: 8375: 8361: 8336: 8079: 7224: 6646: 5093:

White SW, Zheng J, Zhang YM (2005). "The structural biology of type II fatty acid biosynthesis".

1753:. Humans and other mammals have a dietary requirement for certain essential fatty acids, such as 1404: 1400: 989: 765: 508: 504: 291: 193:

and their derivatives (including tri-, di-, monoglycerides, and phospholipids), as well as other

818:. Ceramides (N-acyl-sphingoid bases) are a major subclass of sphingoid base derivatives with an 8666: 8600: 8486: 8481: 8186: 7905: 7862: 7555: 1825: 1706: 1643: 1574: 1100: 837:

to the sphingoid base. Examples of these are the simple and complex glycosphingolipids such as

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Chirala SS, Wakil SJ (November 2004). "Structure and function of animal fatty acid synthase".

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Coleman RA, Lee DP (March 2004). "Enzymes of triacylglycerol synthesis and their regulation".

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Sphingolipids are a complicated family of compounds that share a common structural feature, a

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are also classified as phospholipids), are ubiquitous in nature and are key components of the

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small molecules; the amphiphilic nature of some lipids allows them to form structures such as

8671: 8636: 8592: 8356: 8215: 8002: 7816: 7416: 6957: 6951: 6779: 6773: 6767: 6640: 5106: 3314: 2575: 2569: 1806: 1609: 550: 361:, from Ancient Greek -ίδης (meaning 'son of' or 'descendant of'), is always pronounced (ɪd). 6834: 6828: 3788:"Investigating lipid headgroup composition within epithelial membranes: a systematic review" 3581:"Kdo2-Lipid A of Escherichia coli, a defined endotoxin that activates macrophages via TLR-4" 1356: 1256: 8760: 8610: 8315: 8291: 8253: 7637: 7632: 6909: 6785: 6610: 6399: 6314: 6090: 6035: 4875: 4820: 4699: 4369: 4170: 3799: 3646: 3345: 2964: 2184: 1810: 1762: 1662:. Lanosterol can then be converted into other steroids such as cholesterol and ergosterol. 1651: 1602: 1598: 1550: 1412: 1288: 1218: 1214: 1138: 757: 631: 579: 566: 473: 444: 147: 7140: 5028: 4614:

Boyce JA (August 2008). "Eicosanoids in asthma, allergic inflammation, and host defense".

1024:, which contain an isoprenoid tail attached to a quinonoid core of non-isoprenoid origin. 8: 8555: 8174: 8098: 7622: 7596: 7245: 2899: 1766: 1546: 1134: 926: 741: 737: 682: 261: 167: 80: 57: 6755: 6743: 5959: 5271: 4879: 4824: 4711: 4703: 4373: 4174: 3850:

Heinz E. (1996). "Plant glycolipids: structure, isolation and analysis", pp. 211–332 in

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Raetz CR, Garrett TA, Reynolds CM, Shaw WA, Moore JD, Smith DC, et al. (May 2006).

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Kuzuyama T, Seto H (April 2003). "Diversity of the biosynthesis of the isoprene units".

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Michelle A, Hopkins J, McLaughlin CW, Johnson S, Warner MQ, LaHart D, Wright JD (1993).

8780: 8770: 8678: 8351: 8296: 8283: 8040: 7926: 7798: 7627: 7378: 7035: 7011: 6968: 6873: 6675: 6309: 6135: 6130: 6125: 5665: 5623: 5580: 5505: 5480: 5461: 5318: 5197: 5172: 5153: 5075: 4945: 4920: 4901: 4844: 4723: 4550: 4477: 4429: 4404: 4342: 4294: 4269: 4194: 4131: 4104: 4028: 4003: 3979: 3954: 3935: 3900: 3833: 3763: 3738: 3670: 2988: 2911: 2691: 2433: 2126: 2099: 2071: 2046: 2022: 1995: 1837: 1758: 1690: 1639: 1428: 1292: 1096: 954: 786: 753: 666: 583: 4080: 4055: 3278: 3261: 3050: 3019: 2796: 8550: 8346: 8190: 8148: 8143: 7973: 7901: 7608: 7320: 7315: 7310: 7305: 7275: 7215: 7122: 6899: 6574: 6550: 6514: 5905: 5884: 5865: 5846: 5779: 5736: 5700: 5669: 5657: 5615: 5611: 5572: 5537: 5510: 5453: 5418: 5383: 5346: 5310: 5275: 5237: 5202: 5145: 5141: 5110: 5067: 5002: 4988: 4950: 4893: 4836: 4793: 4789: 4758: 4754: 4715: 4672: 4667: 4650: 4631: 4596: 4555: 4535: 4504: 4469: 4434: 4385: 4334: 4299: 4250: 4186: 4136: 4085: 4033: 3984: 3904: 3892: 3855: 3837: 3825: 3817: 3768: 3719: 3662: 3612: 3558: 3523: 3519: 3488: 3453: 3413: 3376: 3357: 3318: 3283: 3242: 3201: 3197: 3166: 3162: 3129: 3099: 3095: 3064: 3054: 3023: 2980: 2903: 2868: 2828: 2800: 2765: 2755: 2683: 2646: 2620: 2616: 2600: 2579: 2548: 2523: 2458: 2369: 2262: 2235: 2163: 2157: 2131: 2095: 2076: 2027: 1967: 1923: 1865: 1718: 1296: 801: 761: 602: 456: 448: 440: 318: 277: 143: 120: 8090: 5627: 5584: 5465: 5233: 5188: 5157: 4905: 4727: 4420: 4346: 4198: 3674: 2992: 2955:

Berridge MJ, Irvine RF (September 1989). "Inositol phosphates and cell signalling".

2437: 8573: 8021: 7938: 7931: 7347: 7337: 7332: 7327: 7297: 6976: 6945: 6816: 6749: 6634: 6598: 6538: 6153: 5998:– Japanese database of lipids and related properties, spectral data and references. 5953: 5771: 5728: 5692: 5649: 5607: 5564: 5500: 5492: 5445: 5410: 5375: 5322: 5302: 5267: 5229: 5192: 5184: 5137: 5102: 5079: 5059: 4992: 4984: 4940: 4932: 4883: 4848: 4828: 4785: 4750: 4707: 4662: 4623: 4586: 4545: 4527: 4481: 4461: 4424: 4416: 4377: 4326: 4289: 4281: 4240: 4178: 4126: 4116: 4075: 4071: 4067: 4051: 4023: 4015: 3974: 3966: 3927: 3884: 3807: 3758: 3750: 3709: 3701: 3654: 3602: 3592: 3550: 3515: 3480: 3445: 3405: 3353: 3310: 3301:

Russell DW (2003). "The enzymes, regulation, and genetics of bile acid synthesis".

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as substrates. One important reaction that uses these activated isoprene donors is

1448: 1416: 1396: 1142: 1108: 546: 477: 338: 5481:"Trans fatty acids: effects on cardiometabolic health and implications for policy" 4888: 4863: 4832: 4202: 3939: 3754: 3554: 2864: 2321: 1359:), compared with only 17 kJ/g (4 kcal/g) for the oxidative breakdown of 294:(1847) discovered phospholipids in mammalian brain and hen egg, called by him as " 8850: 8527: 8409: 7342: 6586: 6568: 6562: 6502: 6478: 6231: 6075: 6028: 5899: 5840: 5340: 4531: 3262:"Phospholipid/cholesterol model membranes: formation of cholesterol crystallites" 2822: 2502: 2452: 2363: 2344: 2256: 2229: 2207: 1686: 1496: 1384: 1320: 1287:. The formation of lipid bilayers is an energetically preferred process when the 1222: 834: 452: 218: 112: 5804: 5496: 4811:

Helenius A, Aebi M (March 2001). "Intracellular functions of N-linked glycans".

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units. Structures containing greater than 40 carbons are known as polyterpenes.

883: 8834: 8729: 8604: 8522: 8512: 8461: 8449: 8422: 7885: 7834: 7373: 7264: 7235: 6994: 6939: 6921: 6616: 6544: 6490: 6442: 6370: 6221: 5989: 5449: 5414: 4921:"Mitochondrial membrane biogenesis: phospholipids and proteins go hand in hand" 4627: 4245: 4228: 4109:

Proceedings of the National Academy of Sciences of the United States of America

3705: 3597: 3580: 3484: 3409: 2012: 1898: 1870: 1670: 1538: 1492: 1420: 1408: 1388: 1281: 1084: 997: 950: 918: 891: 797: 730: 714: 662: 655: 517: 496:. If a fatty acid contains a double bond, there is the possibility of either a 417: 128: 5568: 5379: 5063: 4381: 4330: 4182: 2679: 368:

defined "simple lipids" as greases and waxes (true waxes, sterols, alcohols).

8844: 8750: 8740: 8476: 8163: 8013: 7778: 7097: 7078: 7047: 6982: 6915: 6893: 6604: 6592: 6526: 6520: 6508: 6472: 6466: 6434: 6249: 6211: 6206: 6191: 6158: 6070: 5696: 4465: 4019: 3888: 3821: 1860: 1778: 1774: 1770: 1754: 1746: 1594: 1504: 1500: 1480: 1328: 1312: 1284: 1273: 1242: 1230: 1226: 1170: 1166: 1158: 1150: 1130: 1104: 1080: 826: 790: 706: 702: 623: 554: 406: 311: 284: 257: 175: 124: 116: 100: 5128:

Ohlrogge JB, Jaworski JG (June 1997). "Regulation of fatty acid synthesis".

4121: 3658: 2454:

Lipid Analysis: Isolation, Separation, Identification and Lipidomic Analysis

1315:. Other aggregations are also observed and form part of the polymorphism of 772:) glycerophospholipids, as well as dialkylether variants in archaebacteria. 687: 151: 8745: 8456: 8426: 8231: 8203: 7897: 7582: 7501: 7196: 7025: 6988: 6844: 6622: 6580: 6556: 6532: 6460: 6454: 6448: 6339: 6301: 6264: 6259: 6226: 6216: 6163: 5783: 5740: 5732: 5704: 5661: 5619: 5576: 5541: 5514: 5457: 5422: 5387: 5241: 5206: 5149: 5114: 5071: 4954: 4897: 4840: 4719: 4676: 4635: 4600: 4559: 4508: 4473: 4438: 4389: 4338: 4303: 4254: 4190: 4140: 4037: 3988: 3896: 3829: 3772: 3723: 3666: 3616: 3562: 3492: 3457: 3417: 3322: 3287: 3246: 3068: 3027: 2907: 2872: 2804: 2769: 2687: 2429: 2135: 2080: 2031: 1855: 1674: 1642:

produces these compounds from acetyl-CoA, while in plants and bacteria the

1582: 1567: 1436: 1424: 1360: 1261: 1178: 1021: 946: 942: 938: 887: 879: 781: 698: 647: 398: 394: 249: 186: 171: 163: 108: 54: 42: 34: 5972: 5775: 5653: 5314: 5279: 5006: 4936: 4762: 4270:"Modular mechanism of Wnt signaling inhibition by Wnt inhibitory factor 1" 4089: 3527: 3205: 3170: 3103: 2984: 2624: 1303:

of the lipid, this biophysical interaction may result in the formation of

1016:. Another biologically important class of molecules is exemplified by the 538:

form does exist in some natural and partially hydrogenated fats and oils.

158:

groups. Using this approach, lipids may be divided into eight categories:

8822: 8582: 8444: 8051: 7960: 7948: 7921: 7769: 7755: 7735: 7726: 7211: 7200: 7184: 7175: 7041: 6628: 6496: 6484: 6380: 6375: 6365: 6324: 6274: 6269: 6254: 6201: 6196: 6173: 6168: 5962:– The Virtual Library of Biochemistry, Molecular Biology and Cell Biology 4997: 4797: 4403:

Dinasarapu AR, Saunders B, Ozerlat I, Azam K, Subramaniam S (June 2011).

3739:"Biosynthesis and function of polyacetylenes and allied natural products" 2116: 1996:"Update of the LIPID MAPS comprehensive classification system for lipids" 1786: 1750: 1678: 1542: 1508: 1343: 1234: 1154: 1088: 1061: 1037: 1036:, are examples of this class. Prokaryotes synthesize polyprenols (called 1009: 958: 871: 858: 842: 838: 815: 769: 670: 587: 562: 558: 464: 460: 436: 424: 307: 269: 202: 104: 26: 7547: 8683: 8405: 8326: 8307: 8239: 8182: 8125: 8121: 7893: 7839: 7019: 6426: 6183: 6145: 5306: 3931: 3812: 3787: 3607: 3043:

Lipidomics and Bioactive Lipids: Mass-Spectrometry–Based Lipid Analysis

2545:

Lipodomics and Bioactive Lipids: Mass Spectrometry Based Lipid Analysis

1876: 1742: 1738: 1682: 1659: 1623: 1590: 1578: 1534: 1476: 1472: 1324: 1316: 1190: 1186: 1174: 1146: 1033: 1005: 907: 710: 627: 591: 575: 542: 432: 389: 377: 273: 265: 245: 206: 198: 190: 179: 159: 139: 135: 30: 6391: 4285: 3714: 2062: 8765: 8578: 8385: 8129: 8032: 7994: 7059: 6241: 6120: 4494: 3449: 3398:

Best Practice & Research. Clinical Endocrinology & Metabolism

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is the metabolic process by which fatty acids are broken down in the

1619: 1444: 1368: 1339: 1332: 1308: 1238: 1210: 1206: 1162: 1073: 1029: 1025: 1013: 973: 965:, are characterized by cleavage of the B ring of the core structure. 962: 895: 875: 722: 571: 468: 96: 92: 88: 84: 46: 21: 3970: 3395: 2413: 1541:

of fatty acids in the production of triglycerides, a process called

1291:

described above are in an aqueous environment. This is known as the

8829: 8059: 7913: 7803: 7590: 6347: 6289: 6284: 5904:(2nd ed.). Menlo Park, California: Benjamin/Cummings Pub. Co. 4268:

Malinauskas T, Aricescu AR, Lu W, Siebold C, Jones EY (July 2011).

3689: 2827:(2nd ed.). Menlo Park, California: Benjamin/Cummings Pub. Co. 2601:"C NMR studies of lipid fatty acyl chains of chloroplast membranes" 1885: 1802: 1790: 1782: 1655: 1484: 1455: 1440: 1432: 1265: 1149:

are cyclic molecules whose backbones are often further modified by

1041: 934: 930: 811: 745: 639: 619: 489: 323: 303: 295: 253: 155: 50: 16:

Substance of biological origin that is soluble in nonpolar solvents

6020: 5992:– Comprehensive lipid and lipid-associated gene/protein databases. 1423:, which are one type of fatty-acid derived eicosanoid involved in 8790: 8785: 8698: 8641: 8626: 7829: 6357: 6279: 4591: 4574: 3237: 3220: 3186:

Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism

1734: 1635: 1634:. These precursors can be made in different ways. In animals and 1615: 1563: 1468: 1451: 1364: 1304: 1269: 1092: 1017: 1001: 922: 914: 830: 485: 413: 5717: 5640:

Astrup A (February 2005). "The role of dietary fat in obesity".

4651:"Liver X receptors (LXR) as therapeutic targets in dyslipidemia" 3687: 2547:. Methods in Enzymology. Vol. 423. Boston: Academic Press. 2155: 2093: 582:

derivatives and fatty acid carnitines. The fatty amides include

345:

was unanimously approved by the international commission of the

8755: 7425: 7360: 4689: 3375:. Cambridge, Massachusetts: Blackwell Publishers. p. 342. 1794: 1769:

differing in the number and position of the double bonds. Most

1558: 1554: 1372: 1246: 1126: 985: 903: 865: 807: 493: 481: 194: 76: 38: 5760: 2741: 1993: 1805:

are particularly rich in the longer-chain omega-3 fatty acids

1601:

cannot be synthesized in mammalian tissues, and are therefore

1415:

phosphates (PIPs), involved in calcium-mediated activation of

1052: 853: 638:

Glycerolipids are composed of mono-, di-, and tri-substituted

111:, and others. The functions of lipids include storing energy, 8795: 7536: 7531: 7526: 7488: 7483: 7443: 7290: 7285: 7280: 5947: 5222:

Annual Review of Plant Physiology and Plant Molecular Biology

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Annual Review of Plant Physiology and Plant Molecular Biology

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Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes

4778:

Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes

4405:"Signaling gateway molecule pages – a data model perspective" 4402: 3471:

Rao AV, Rao LG (March 2007). "Carotenoids and human health".

3335: 2282:

Pelouze TJ, Gélis A (1844). "Mémoire sur l'acide butyrique".

899: 819: 643: 357:

because of its pronunciation ('lɪpɪd). In French, the suffix

8817: 5935: 5597: 5400: 4526:. Subcellular Biochemistry. Vol. 49. pp. 413–440. 4267: 2746:. Subcellular Biochemistry. Vol. 49. pp. 101–132. 1816:

In contrast, it is now well-established that consumption of

988:

lipids are synthesized from the five-carbon-unit precursors

7473: 7463: 7453: 7448: 7438: 7170: 3149:

Hori T, Sugita M (1993). "Sphingolipids in lower animals".

3082:

Paltauf F (December 1994). "Ether lipids in biomembranes".

2922: 2480:"Projet de reforme de la nomenclature de Chimie biologique" 1069: 541:

Examples of biologically important fatty acids include the

337:'fat', was introduced in 1923 by the French pharmacologist 3119:"Chapter 14: Sphingolipids: Metabolism and Cell Signaling" 1658:

and then folded up and formed into a set of rings to make

1177:

agents are polyketides or polyketide derivatives, such as

764:

are either precursors of or, themselves, membrane-derived

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Caffrey P, Aparicio JF, Malpartida F, Zotchev SB (2008).

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polymerization in bacteria), and in eukaryotic protein N-

917:

in which one of the hydrogen atoms is substituted with a

651: 376:

Lipids have been classified into eight categories by the

72: 68: 6014: 4153: 3952: 3578: 3045:. Methods in Enzymology. Vol. 432. pp. 21–57. 3005: 2368:(3rd ed.). London: Butterworths. pp. 351–376. 2255:

Leray C (2015). "Introduction, History and Evolution.".

5995: 5944:– General reference on lipid chemistry and biochemistry 5485:

Prostaglandins, Leukotrienes, and Essential Fatty Acids

4740: 4488: 3128:(4th ed.). Amsterdam: Elsevier. pp. 373–407. 2362:

Culling CF (1974). "Lipids. (Fats, Lipoids. Lipins).".

2044: 1654:. Here, the isoprene units are joined together to make 8323:(amino acid→pyruvate, acetyl CoA, or TCA intermediate) 3953:

van Meer G, Voelker DR, Feigenson GW (February 2008).

3040: 8806: 8120: 5978:

IUPAC glossary entry for the lipid class of molecules

4861: 4521: 3955:"Membrane lipids: where they are and how they behave" 3540: 2885: 810:

and a long-chain fatty acyl CoA, then converted into

349:

during the plenary session on July 3, 1923. The word

67:

are a broad group of organic compounds which include

5862:

Textbook of Biochemistry: With Clinical Correlations

5292: 2702: 2643:

Textbook of Biochemistry: With Clinical Correlations

2047:"Bioinformatics and systems biology of the lipidome" 1881:

Pages displaying wikidata descriptions as a fallback

1201: 455:

group; this arrangement confers the molecule with a

5864:(4th ed.). Chichester: John Wiley & Sons. 3854:, Vol. 3. W.W. Christie (ed.). Oily Press, Dundee. 2645:(4th ed.). Chichester: John Wiley & Sons. 1705:. The acetyl-CoA is then ultimately converted into 1213:that carry out different biological functions. The 1209:cells feature the compartmentalized membrane-bound 5683:Astrup A (2008). "Dietary management of obesity". 5554: 5253: 5251: 5213: 4743:Biochimica et Biophysica Acta (BBA) - Biomembranes 3785: 3266:Biochimica et Biophysica Acta (BBA) - Biomembranes 3126:Biochemistry of Lipids, Lipoproteins and Membranes 2520:Biochemistry of Lipids, Lipoproteins and Membranes 1961: 1516:. Lipids also form the basis of steroid hormones. 1008:are important simple isoprenoids that function as 5938:– Round-up and summaries of recent lipid research 5170: 3184:Wiegandt H (January 1992). "Insect glycolipids". 2816: 2814: 2711:"A Long Lipid, a Long Name: Docosahexaenoic Acid" 1335:" cage around the dissolved lipophilic molecule. 1125:Polyketides are synthesized by polymerization of 929:. The eighteen-carbon (C18) steroids include the 240:The first synthetic triglyceride was reported by 25:Structures of some common lipids. At the top are 8842: 5548: 5478: 5334: 5332: 5127: 4154:Segré D, Ben-Eli D, Deamer DW, Lancet D (2001). 3431: 3429: 3427: 2820: 2567: 205:. Although humans and other mammals use various 5711: 5527: 5248: 5164: 5092: 4396: 3864: 3534: 3505: 2209:Recherches sur les corps gras d'origine animale 2162:. Englewood Cliffs, New Jersey: Prentice Hall. 2038: 521:, the most abundant fatty-acyl chains of plant 333:, which stems etymologically from Greek λίπος, 4918: 4864:"Cardiolipin synthase of Arabidopsis thaliana" 4862:Nowicki M, Müller F, Frentzen M (April 2005). 4642: 4515: 4220: 4163:Origins of Life and Evolution of the Biosphere 3995: 3736: 3329: 3116: 2954: 2811: 2729:"DHA for Optimal Brain and Visual Functioning" 2636: 2634: 2388: 1391:. Lipid signaling may occur via activation of 825:The major phosphosphingolipids of mammals are 302:discovered in human brain some phospholipids ( 8714: 8106: 7870: 7563: 7156: 6407: 6036: 5883:(6th ed.). San Francisco: W.H. Freeman. 5676: 5521: 5394: 5329: 5258:Schroepfer GJ (1981). "Sterol biosynthesis". 5219: 5121: 4804: 4683: 4310: 4102: 3946: 3786:Coones RT, Green RJ, Frazier RA (July 2021). 3574: 3572: 3499: 3424: 3389: 3177: 2948: 2846: 2844: 2605:Indian Journal of Biochemistry and Biophysics 2574:. Belmont, California: West Pub. Co. p. 2176: 1966:(6th ed.). San Francisco: W.H. Freeman. 1957: 1955: 1953: 1951: 1949: 1947: 1945: 1943: 1941: 1939: 1922:. W W Norton & Co Inc (Np). p. 139. 1342:membranes represents a key step in models of 933:family whereas the C19 steroids comprise the 697:Glycerophospholipids, usually referred to as 606:Example of an unsaturated fat triglyceride (C 507:, which significantly affects the molecule's 5754: 5403:Journal of the American Dietetic Association 5049: 5043: 4855: 4810: 4775: 4572: 4261: 4096: 4056:"Role of water in some biological processes" 4044: 3911: 3681: 3435: 3294: 3075: 3034: 2999: 2850: 2776: 2592: 2281: 2223: 2221: 2219: 2199: 2149: 2087: 1911: 5764:Journal of the American Medical Association 5721:Journal of the American Medical Association 5685:Journal of Parenteral and Enteral Nutrition 5633: 5591: 4769: 4445: 4316: 3364: 3259: 2659: 2631: 2484:Bulletin de la Société de Chimie Biologique 2450: 2104:International Journal of Molecular Sciences 1989: 1987: 1985: 1983: 1253:resonance and electron microscope studies. 658:are the initial steps in metabolizing fat. 8721: 8707: 8113: 8099: 7877: 7863: 7570: 7556: 7163: 7149: 6414: 6400: 6043: 6029: 5472: 5429: 5359: 5257: 5171:Grochowski LL, Xu H, White RH (May 2006). 5086: 4912: 4607: 4566: 4147: 3877:Journal of Agricultural and Food Chemistry 3730: 3630: 3569: 3148: 2879: 2841: 2782: 2735: 2536: 2517: 2511: 2248: 1936: 1608:Triglyceride synthesis takes place in the 1233:environment. The glycerophospholipids are 736:Examples of glycerophospholipids found in 189:. Lipids also encompass molecules such as 7577: 5960:Lipids, Membranes and Vesicle Trafficking 5504: 5435: 5286: 5196: 4996: 4961: 4944: 4887: 4666: 4648: 4590: 4549: 4428: 4353: 4293: 4274:Nature Structural & Molecular Biology 4244: 4226: 4130: 4120: 4079: 4027: 4001: 3978: 3870: 3811: 3762: 3713: 3606: 3596: 3277: 3253: 3236: 3212: 3142: 2561: 2504:The Chemical Constitution of Natural Fats 2414:"Outline of a classication of the lipids" 2216: 2182: 2125: 2115: 2070: 2021: 2011: 1165:, or other processes. Many commonly used 276:with glycerin in the presence of gaseous 264:, one of Pelouze's students, synthesized 115:, and acting as structural components of 5815: 5338: 5107:10.1146/annurev.biochem.74.082803.133524 4919:Gohil VM, Greenberg ML (February 2009). 4497:Current Opinion in Investigational Drugs 3464: 3315:10.1146/annurev.biochem.72.121801.161712 3218: 3183: 2500: 2477: 2365:Handbook of Histopathological Techniques 2205: 1980: 1917: 1873: – Lipid molecules on cell membrane 1447:such as 25-hydroxy-cholesterol that are 1255: 1051: 972: 894:; the latter compound is also used as a 852: 785: 721:-3 position of the glycerol backbone in 686: 601: 412: 393: 20: 6421: 5879:Stryer L, Berg JM, Tymoczko JL (2007). 4970:"Cardiolipins and biomembrane function" 4360:Wang X (June 2004). "Lipid signaling". 4050: 3917: 3300: 3110: 3081: 2598: 2571:Advanced Nutrition and Human Metabolism 2457:. Bridgwater, England: The Oily Press. 2361: 2314:"Chronological history of lipid center" 1962:Stryer L, Berg JM, Tymoczko JL (2007). 1728: 1196: 709:of cells, as well as being involved in 676: 8843: 5845:. San Diego: Harcourt/Academic Press. 5682: 5639: 5345:. San Diego: Harcourt/Academic Press. 4451: 3470: 3370: 2665: 2640: 2568:Hunt SM, Groff JL, Gropper SA (1995). 1044:) the terminal isoprenoid is reduced. 642:, the best-known being the fatty acid 53:backbone. At the bottom is the common 8702: 8094: 7858: 7551: 7144: 6395: 6024: 5365: 4613: 3959:Nature Reviews Molecular Cell Biology 3844: 3694:Current Topics in Medicinal Chemistry 3636: 2708: 2542: 2411: 2342: 2254: 2227: 1822:partially hydrogenated vegetable oils 1557:group and then reduce it again to an 1217:are the main structural component of 1103:. Typical lipid A molecules are 8223:Electron acceptors other than oxygen 4967: 4573:Klein C, Malviya AN (January 2008). 4359: 3737:Minto RE, Blacklock BJ (July 2008). 1605:and must be obtained from the diet. 1593:. The doubly unsaturated fatty acid 996:, which are produced mainly via the 6050: 5950:– Resources and history for lipids. 5272:10.1146/annurev.bi.50.070181.003101 3508:Free Radical Biology & Medicine 1888: – Totality of lipids in cells 1280:A biological membrane is a form of 13: 8728: 6798:6,9,12,15,18,21-Tetracosahexaenoic 5825:. Harvard School of Public Health. 5809:T. H. Chan School of Public Health 4004:"Phase behavior of lipid mixtures" 2900:10.1023/B:GLYC.0000043749.06556.3d 1852: – Novel drug delivery system 1834:T. H. Chan School of Public Health 1597:as well as the triply unsaturated 1462: 1383:Evidence has emerged showing that 1056:Structure of the saccharolipid Kdo 902:growth. The predominant sterol in 622:; right part, from top to bottom: 578:derivatives, fatty acid thioester 119:. Lipids have applications in the 14: 8867: 6792:9,12,15,18,21-Tetracosapentaenoic 5919: 5898:van Holde KE, Mathews CK (1996). 4103:Raschke TM, Levitt M (May 2005). 3221:"Biochemistry of inositol lipids" 2821:van Holde KE, Mathews CK (1996). 2311: 1349: 1202:Component of biological membranes 1047: 134:Lipids may be broadly defined as 8828: 8816: 7254: 5797: 5789: 5746: 5612:10.1111/j.1467-789X.2007.00438.x 5142:10.1146/annurev.arplant.48.1.109 4668:10.1111/j.1755-5922.2008.00062.x 4454:Advances in Physiology Education 4362:Current Opinion in Plant Biology 3622: 3358:10.1016/j.orggeochem.2008.01.009 3260:Bach D, Wachtel E (March 2003). 3124:. In Vance JE, Vance EE (eds.). 2284:Annales de Chimie et de Physique 2141: 945:. The C21 subclass includes the 775: 597: 525:, render these membranes highly 256:in the presence of concentrated 8244:Substrate-level phosphorylation 5931:List of lipid-related web sites 5832: 5557:Current Atherosclerosis Reports 5479:Micha R, Mozaffarian D (2008). 5234:10.1146/annurev.arplant.50.1.47 5189:10.1128/JB.188.9.3192-3198.2006 5013: 4734: 3779: 3084:Chemistry and Physics of Lipids 3008:Chemistry and Physics of Lipids 2721: 2501:Hilditch, Thomas Percy (1956). 2494: 2471: 2444: 2405: 2382: 2355: 2336: 2305: 2294: 2275: 1528: 1431:; the steroid hormones such as 8781:"Minerals" (Chemical elements) 6330:Dipalmitoylphosphatidylcholine 5954:Molecular Computer Simulations 4227:Brasaemle DL (December 2007). 4072:10.1128/MMBR.54.4.432-449.1990 4002:Feigenson GW (November 2006). 3117:Merrill AH, Sandoff K (2002). 2389:Rosenbloom J, Gies WJ (1911). 2185:"Sur la nature des corps gras" 2098:, Mashaghi A (February 2013). 1665: 1120: 961:, comprising various forms of 383: 229:(solid greases or tallow) and 1: 8647:Reverse cholesterol transport 5956:– Modeling of Lipid Membranes 5838: 5642:Seminars in Vascular Medicine 5260:Annual Review of Biochemistry 5095:Annual Review of Biochemistry 4889:10.1016/j.febslet.2005.03.007 4833:10.1126/science.291.5512.2364 4712:10.1088/1478-3975/10/6/065007 4421:10.1093/bioinformatics/btr190 3852:Advances in Lipid Methodology 3755:10.1016/j.plipres.2008.02.002 3555:10.1016/j.plipres.2005.05.002 3303:Annual Review of Biochemistry 3279:10.1016/S0005-2736(03)00017-8 3051:10.1016/S0076-6879(07)32002-8 3020:10.1016/S0009-3084(00)00128-6 2930:"The Structure of a Membrane" 2865:10.1016/j.plipres.2007.05.001 2797:10.1016/S0163-7827(03)00051-1 2183:Braconnot H (31 March 1815). 1905: 1570:and secreted from the liver. 1519: 1338:The formation of lipids into 800:backbone that is synthesized 371: 272:by reaction of the analogous 8856:Underwater diving physiology 8299:(protein→peptide→amino acid) 5973:IUPAC nomenclature of lipids 4989:10.1016/0304-4157(92)90035-9 4790:10.1016/0304-4157(79)90006-6 4755:10.1016/0005-2736(91)90110-t 4532:10.1007/978-1-4020-8831-5_16 4524:Lipids in Health and Disease 3520:10.1016/0891-5849(89)90126-3 3219:Guan X, Wenk MR (May 2008). 3198:10.1016/0005-2760(92)90101-Z 3163:10.1016/0163-7827(93)90003-F 3096:10.1016/0009-3084(94)90054-X 2744:Lipids in Health and Disease 2731:. DHA/EPA Omega-3 Institute. 2617:10.1016/0165-022X(91)90019-S 2258:Lipids. Nutrition and health 1467:The "fat-soluble" vitamins ( 1378: 744:(also known as PC, GPCho or 534:configuration, although the 347:Société de Chimie Biologique 33:. The middle structure is a 7: 7618:-ethanolamine/cephalin (PE) 5878: 5859: 5497:10.1016/j.plefa.2008.09.008 4925:The Journal of Cell Biology 4655:Cardiovascular Therapeutics 2752:10.1007/978-1-4020-8831-5_4 2709:Furse S (2 December 2011). 2518:Vance JE, Vance DE (2002). 2451:Christie WW, Han X (2010). 1843: 1820:, such as those present in 1773:are rich in linoleic acid ( 1767:polyunsaturated fatty acids 1632:dimethylallyl pyrophosphate 1323:is an area of study within 729:-1 position in the case of 665:attached to glycerol via a 443:groups in a process called 427:, an eicosanoid fatty acid) 409:, an eicosanoid fatty acid) 10: 8872: 8684:Phospagen system (ATP-PCr) 8154:Primary nutritional groups 7741:Platelet-activating factor 6086:Polyunsaturated fatty acid 6081:Monounsaturated fatty acid 6015:National Lipid Association 5897: 5450:10.1177/026010600902000102 5415:10.1016/j.jada.2008.12.022 4628:10.2174/156652408785160989 4616:Current Molecular Medicine 4246:10.1194/jlr.R700014-JLR200 3743:Progress in Lipid Research 3706:10.2174/156802608784221479 3598:10.1194/jlr.M600027-JLR200 3543:Progress in Lipid Research 3485:10.1016/j.phrs.2007.01.012 3410:10.1016/j.beem.2006.09.008 3151:Progress in Lipid Research 2853:Progress in Lipid Research 2785:Progress in Lipid Research 2231:Introduction to Lipidomics 2013:10.1194/jlr.R800095-JLR200 1648:glyceraldehyde 3-phosphate 1545:. Fatty acids are made by 968: 863: 848: 779: 680: 387: 244:in 1844, when he produced 212: 8736: 8659: 8619: 8591: 8572: 8546: 8518:Anoxygenic photosynthesis 8508: 8501: 8472: 8440:Pentose phosphate pathway 8435: 8418: 8401: 8394: 8374: 8335: 8306: 8282: 8273: 8230: 8214: 8195:Oxidative phosphorylation 8173: 8162: 8136: 8072: 8049: 8030: 8011: 7992: 7958: 7947: 7912: 7825: 7812: 7794: 7787: 7768: 7751: 7725: 7654: 7607: 7589: 7515: 7415: 7387: 7358: 7263: 7252: 7183: 7107: 7088: 7069: 7010: 6967: 6872: 6807: 6674: 6433: 6356: 6338: 6320:Phosphatidyl ethanolamine 6300: 6240: 6182: 6144: 6113: 6059: 5936:Nature Lipidomics Gateway 5569:10.1007/s11883-007-0065-9 5380:10.1016/j.bcp.2008.10.020 5064:10.1007/s11745-004-1329-9 4382:10.1016/j.pbi.2004.03.012 4331:10.1007/s11745-007-3144-3 4233:Journal of Lipid Research 3585:Journal of Lipid Research 2680:10.1007/s11745-006-5049-y 2418:Proc. Soc. Exp. Biol. Med 2261:. Boca Raton: CRC Press. 2234:. Boca Raton: CRC Press. 2000:Journal of Lipid Research 1894:Protein–lipid interaction 1628:isopentenyl pyrophosphate 1587:stearoyl-CoA desaturase-1 1514:oxidative phosphorylation 994:dimethylallyl diphosphate 545:, derived primarily from 476:, and may be attached to 8538:Entner-Doudoroff pathway 8200:electron transport chain 8187:Pyruvate decarboxylation 6851:7,10,13-Octadecatrienoic 5697:10.1177/0148607108321707 5368:Biochemical Pharmacology 4466:10.1152/advan.00088.2006 4020:10.1038/nchembio1106-560 3889:10.1021/acs.jafc.1c00204 3473:Pharmacological Research 2159:Human Biology and Health 1850:Solid lipid nanoparticle 1824:, are a risk factor for 1723:electron transport chain 750:phosphatidylethanolamine 692:Phosphatidylethanolamine 353:was later anglicized as 8632:Sphingolipid metabolism 8533:DeLey-Doudoroff pathway 8381:carbohydrate catabolism 8376:Carbohydrate metabolism 8362:Purine nucleotide cycle 8080:Sphingosine-1-phosphate 7906:metabolic intermediates 7389:Lipid transfer proteins 5530:International Angiology 5177:Journal of Bacteriology 4579:Frontiers in Bioscience 4183:10.1023/A:1006746807104 4122:10.1073/pnas.0500225102 4060:Microbiological Reviews 4008:Nature Chemical Biology 3659:10.1126/science.1094318 3438:Natural Product Reports 3225:Frontiers in Bioscience 2522:. Amsterdam: Elsevier. 1575:unsaturated fatty acids 1405:sphingosine-1-phosphate 1387:is a vital part of the 990:isopentenyl diphosphate 725:and eubacteria, or the 574:, fatty acid thioester 451:that terminates with a 380:consortium as follows: 260:. Several years later, 242:Théophile-Jules Pelouze 233:(fluid oils). In 1823, 8601:Fatty acid degradation 8321:Amino acid degradation 7623:-choline/lecithin (PC) 7417:Cell surface receptors 7001:7,10,13-Eicosatrienoic 6857:9,12,15-Eicosatrienoic 5805:"The Nutrition Source" 5733:10.1001/jama.295.6.643 4968:Hoch FL (March 1992). 3920:Journal of Biosciences 2888:Glycoconjugate Journal 2543:Brown HA, ed. (2007). 2430:10.3181/00379727-17-75 2100:"Lipid nanotechnology" 2094:Mashaghi S, Jadidi T, 1918:Maitland J Jr (1998). 1826:cardiovascular disease 1707:adenosine triphosphate 1644:non-mevalonate pathway 1346:, the origin of life. 1277: 1101:Gram-negative bacteria 1077: 982: 861: 857:Chemical structure of 793: 694: 635: 428: 410: 235:Michel Eugène Chevreul 61: 8761:Essential fatty acids 8637:Eicosanoid metabolism 8593:Fatty acid metabolism 8357:Pyrimidine metabolism 8216:Anaerobic respiration 8003:Globotriaosylceramide 7817:Lysophosphatidic acid 7597:Glycerophospholipids/ 5811:. Harvard University. 5776:10.1001/jama.295.1.39 5654:10.1055/s-2005-871740 4937:10.1083/jcb.200901127 1807:eicosapentaenoic acid 1610:endoplasmic reticulum 1603:essential fatty acids 1260:Self-organization of 1259: 1139:secondary metabolites 1137:. They comprise many 1055: 1012:and as precursors of 976: 856: 789: 758:phosphatidylinositols 690: 605: 551:eicosapentaenoic acid 463:end, and a nonpolar, 447:. They are made of a 416: 397: 310:) and sphingolipids ( 280:at high temperature. 225:) in two categories, 207:biosynthetic pathways 148:unilamellar liposomes 49:chains attached to a 24: 8611:Fatty acid synthesis 8316:Amino acid synthesis 7519:cassette transporter 6315:Phosphatidylinositol 6091:Essential fatty acid 5842:Medical Biochemistry 5839:Bhagavan NV (2002). 5438:Nutrition and Health 5342:Medical Biochemistry 5339:Bhagavan NV (2002). 4649:Bełtowski J (2008). 4208:on 11 September 2008 3338:Organic Geochemistry 2934:The Lipid Chronicles 2715:The Lipid Chronicles 2206:Chevreul ME (1823). 2117:10.3390/ijms14024242 1811:docosahexaenoic acid 1763:alpha-linolenic acid 1729:Nutrition and health 1701:, which is split by 1652:steroid biosynthesis 1547:fatty acid synthases 1413:phosphatidylinositol 1289:glycerophospholipids 1229:components from the 1219:biological membranes 1215:glycerophospholipids 1197:Biological functions 1135:fatty acid synthases 1072:chains in black and 806:from the amino acid 738:biological membranes 677:Glycerophospholipids 646:of glycerol, called 632:alpha-linolenic acid 584:N-acyl ethanolamines 567:Docosahexaenoic acid 445:fatty acid synthesis 168:glycerophospholipids 81:fat-soluble vitamins 8175:Aerobic respiration 7246:Remnant cholesterol 7178:particle metabolism 4880:2005FEBSL.579.2161N 4825:2001Sci...291.2364H 4819:(5512): 2364–2369. 4704:2013PhBio..10f5007B 4374:2004COPB....7..329W 4175:2001OLEB...31..119S 3804:2021SMat...17.6773C 3651:2004Sci...303.1805W 3645:(5665): 1805–1810. 3350:2008OrGeo..39..567V 2969:1989Natur.341..197B 2599:Yashroy RC (1987). 2478:Bertrand G (1923). 1483:) – which are 1401:cellular messengers 1299:; depending on the 1097:lipopolysaccharides 927:signaling molecules 742:phosphatidylcholine 683:Glycerophospholipid 523:thylakoid membranes 505:geometric isomerism 262:Marcellin Berthelot 221:classified lipids ( 58:phosphatidylcholine 8679:Ethanol metabolism 8627:Steroid metabolism 8352:Nucleotide salvage 8284:Protein metabolism 8041:Galactocerebroside 7927:Galactocerebroside 7902:glycosphingolipids 7799:Inositol phosphate 7655:Phosphoinositides: 7054:8,11-Eicosadienoic 6934:Dihomo-γ-linolenic 6863:β-Eicosatetraenoic 6762:Dihomo-α-linolenic 6647:Heptatriacontanoic 6310:Phosphatidylserine 6136:Omega−9 fatty acid 6131:Omega−6 fatty acid 6126:Omega−3 fatty acid 5860:Devlin TM (1997). 5307:10.1007/BF02537824 5031:on 23 October 2011 3932:10.1007/BF02702669 3813:10.1039/D1SM00703C 2641:Devlin TM (1997). 2324:on 13 October 2017 2212:. Paris: Levrault. 1838:Harvard University 1759:omega-6 fatty acid 1646:uses pyruvate and 1640:mevalonate pathway 1319:(lipid) behavior. 1293:hydrophobic effect 1278: 1221:, as the cellular 1091:precursors of the 1078: 1064:residues in blue, 983: 955:mineralocorticoids 906:cell membranes is 862: 794: 762:phosphatidic acids 754:phosphatidylserine 752:(PE or GPEtn) and 695: 667:glycosidic linkage 636: 429: 411: 83:(such as vitamins 62: 8804: 8803: 8696: 8695: 8692: 8691: 8655: 8654: 8568: 8567: 8564: 8563: 8551:Xylose metabolism 8497: 8496: 8370: 8369: 8347:Purine metabolism 8292:Protein synthesis 8269: 8268: 8191:Citric acid cycle 8149:Metabolic network 8144:Metabolic pathway 8088: 8087: 8068: 8067: 7852: 7851: 7848: 7847: 7764: 7763: 7599:Phosphoglycerides 7545: 7544: 7138: 7137: 6659:Nonatriacontanoic 6653:Octatriacontanoic 6389: 6388: 5911:978-0-8053-3931-4 5890:978-0-7167-8724-2 5871:978-0-471-17053-2 5852:978-0-12-095440-7 5352:978-0-12-095440-7 5058:(11): 1045–1053. 4874:(10): 2161–2165. 4585:(13): 1206–1226. 4541:978-1-4020-8830-8 4503:(11): 1192–1205. 4415:(12): 1736–1738. 4286:10.1038/nsmb.2081 4239:(12): 2547–2559. 4156:"The lipid world" 4115:(19): 6777–6782. 4054:(December 1990). 3883:(32): 8910–8928. 3860:978-0-9514171-6-4 3798:(28): 6773–6786. 3382:978-1-4051-3066-0 3371:Deacon J (2005). 3231:(13): 3239–3251. 3135:978-0-444-51138-6 3060:978-0-12-373895-0 2963:(6239): 197–205. 2936:. 5 November 2011 2834:978-0-8053-3931-4 2761:978-1-4020-8830-8 2652:978-0-471-17053-2 2585:978-0-314-04467-9 2554:978-0-12-373895-0 2529:978-0-444-51139-3 2412:Bloor WR (1920). 2318:Cyberlipid Center 2195:(XCIII): 225–277. 2189:Annales de chimie 2169:978-0-13-981176-0 2063:10.1021/cr200295k 2057:(10): 6452–6490. 1973:978-0-7167-8724-2 1929:978-0-393-97378-5 1920:Organic Chemistry 1866:Lipid microdomain 1719:citric acid cycle 1573:The synthesis of 1397:nuclear receptors 1393:G protein-coupled 1095:component of the 1068:residues in red, 1032:, as well as the 870:Sterols, such as 766:second messengers 590:neurotransmitter 478:functional groups 449:hydrocarbon chain 441:methylmalonyl-CoA 423:(an example of a 405:(an example of a 278:hydrogen chloride 8863: 8833: 8832: 8821: 8820: 8812: 8723: 8716: 8709: 8700: 8699: 8667:Metal metabolism 8589: 8588: 8574:Lipid metabolism 8506: 8505: 8399: 8398: 8392: 8391: 8304: 8303: 8280: 8279: 8206: 8171: 8170: 8115: 8108: 8101: 8092: 8091: 8022:Glucocerebroside 7956: 7955: 7939:Lactosylceramide 7932:Glucocerebroside 7879: 7872: 7865: 7856: 7855: 7792: 7791: 7605: 7604: 7572: 7565: 7558: 7549: 7548: 7258: 7187:particle classes 7165: 7158: 7151: 7142: 7141: 7109:ω−12 Unsaturated 7090:ω−11 Unsaturated 7071:ω−10 Unsaturated 6774:Eicosapentaenoic 6768:Eicosatetraenoic 6732:Palmitolinolenic 6726:Myristolinolenic 6641:Hexatriacontylic 6416: 6409: 6402: 6393: 6392: 6154:Arachidonic acid 6045: 6038: 6031: 6022: 6021: 5915: 5894: 5875: 5856: 5827: 5826: 5819: 5813: 5812: 5801: 5795: 5794: 5793: 5787: 5758: 5752: 5751: 5750: 5744: 5715: 5709: 5708: 5680: 5674: 5673: 5637: 5631: 5630: 5595: 5589: 5588: 5552: 5546: 5545: 5525: 5519: 5518: 5508: 5491:(3–5): 147–152. 5476: 5470: 5469: 5433: 5427: 5426: 5398: 5392: 5391: 5363: 5357: 5356: 5336: 5327: 5326: 5290: 5284: 5283: 5255: 5246: 5245: 5217: 5211: 5210: 5200: 5183:(9): 3192–3198. 5168: 5162: 5161: 5125: 5119: 5118: 5090: 5084: 5083: 5047: 5041: 5040: 5038: 5036: 5027:. Archived from 5017: 5011: 5010: 5000: 4974: 4965: 4959: 4958: 4948: 4916: 4910: 4909: 4891: 4859: 4853: 4852: 4808: 4802: 4801: 4773: 4767: 4766: 4738: 4732: 4731: 4692:Physical Biology 4687: 4681: 4680: 4670: 4646: 4640: 4639: 4611: 4605: 4604: 4594: 4570: 4564: 4563: 4553: 4519: 4513: 4512: 4492: 4486: 4485: 4449: 4443: 4442: 4432: 4400: 4394: 4393: 4357: 4351: 4350: 4314: 4308: 4307: 4297: 4265: 4259: 4258: 4248: 4224: 4218: 4217: 4215: 4213: 4207: 4201:. Archived from 4169:(1–2): 119–145. 4160: 4151: 4145: 4144: 4134: 4124: 4100: 4094: 4093: 4083: 4048: 4042: 4041: 4031: 3999: 3993: 3992: 3982: 3950: 3944: 3943: 3915: 3909: 3908: 3868: 3862: 3848: 3842: 3841: 3815: 3783: 3777: 3776: 3766: 3734: 3728: 3727: 3717: 3685: 3679: 3678: 3634: 3628: 3627: 3626: 3620: 3610: 3600: 3591:(5): 1097–1111. 3576: 3567: 3566: 3538: 3532: 3531: 3503: 3497: 3496: 3468: 3462: 3461: 3450:10.1039/b109860h 3433: 3422: 3421: 3393: 3387: 3386: 3368: 3362: 3361: 3333: 3327: 3326: 3298: 3292: 3291: 3281: 3257: 3251: 3250: 3240: 3216: 3210: 3209: 3181: 3175: 3174: 3146: 3140: 3139: 3123: 3114: 3108: 3107: 3079: 3073: 3072: 3038: 3032: 3031: 3003: 2997: 2996: 2977:10.1038/341197a0 2952: 2946: 2945: 2943: 2941: 2926: 2920: 2919: 2883: 2877: 2876: 2848: 2839: 2838: 2818: 2809: 2808: 2780: 2774: 2773: 2739: 2733: 2732: 2725: 2719: 2718: 2706: 2700: 2699: 2663: 2657: 2656: 2638: 2629: 2628: 2596: 2590: 2589: 2565: 2559: 2558: 2540: 2534: 2533: 2515: 2509: 2508: 2498: 2492: 2491: 2475: 2469: 2468: 2448: 2442: 2441: 2409: 2403: 2402: 2386: 2380: 2379: 2359: 2353: 2352: 2343:Prout W (1827). 2340: 2334: 2333: 2331: 2329: 2320:. Archived from 2309: 2303: 2298: 2292: 2291: 2279: 2273: 2272: 2252: 2246: 2245: 2228:Leray C (2012). 2225: 2214: 2213: 2203: 2197: 2196: 2180: 2174: 2173: 2153: 2147: 2146: 2145: 2139: 2129: 2119: 2110:(2): 4242–4282. 2091: 2085: 2084: 2074: 2051:Chemical Reviews 2042: 2036: 2035: 2025: 2015: 1991: 1978: 1977: 1959: 1934: 1933: 1915: 1882: 1622:, including the 1599:α-linolenic acid 1497:oligosaccharides 1449:liver X receptor 1417:protein kinase C 1403:. These include 1189:, and antitumor 1143:natural products 1076:groups in green. 547:arachidonic acid 339:Gabriel Bertrand 306:), glycolipids ( 146:, multilamellar/ 8871: 8870: 8866: 8865: 8864: 8862: 8861: 8860: 8841: 8840: 8839: 8827: 8815: 8807: 8805: 8800: 8732: 8727: 8697: 8688: 8672:Iron metabolism 8651: 8615: 8576: 8560: 8542: 8528:Carbon fixation 8493: 8468: 8431: 8414: 8410:Gluconeogenesis 8383: 8378: 8366: 8338: 8331: 8302: 8275: 8265: 8226: 8210: 8198: 8165: 8158: 8132: 8119: 8089: 8084: 8064: 8045: 8026: 8007: 7988: 7951: 7943: 7908: 7886:Glycoconjugates 7883: 7853: 7844: 7821: 7808: 7783: 7760: 7747: 7721: 7717: 7707: 7699: 7691: 7684: 7650: 7598: 7594: 7585: 7576: 7546: 7541: 7518: 7511: 7411: 7383: 7354: 7265:Apolipoproteins 7259: 7250: 7188: 7179: 7169: 7139: 7134: 7103: 7084: 7065: 7012:ω−9 Unsaturated 7006: 6969:ω−7 Unsaturated 6963: 6928:Dihomo-linoleic 6888:12-Octadecenoic 6882:8-Tetradecenoic 6874:ω−6 Unsaturated 6868: 6823:Palmitovaccenic 6809:ω−5 Unsaturated 6803: 6786:Docosahexaenoic 6720:Myristolinoleic 6714:Myristovaccenic 6676:ω−3 Unsaturated 6670: 6611:Hentriacontylic 6429: 6420: 6390: 6385: 6371:Corticosteroids 6352: 6334: 6296: 6236: 6232:Lignoceric acid 6178: 6140: 6109: 6076:Unsaturated fat 6055: 6049: 5922: 5912: 5891: 5872: 5853: 5835: 5830: 5821: 5820: 5816: 5803: 5802: 5798: 5788: 5759: 5755: 5745: 5716: 5712: 5681: 5677: 5638: 5634: 5596: 5592: 5553: 5549: 5526: 5522: 5477: 5473: 5434: 5430: 5399: 5395: 5364: 5360: 5353: 5337: 5330: 5291: 5287: 5256: 5249: 5218: 5214: 5169: 5165: 5126: 5122: 5091: 5087: 5048: 5044: 5034: 5032: 5019: 5018: 5014: 4972: 4966: 4962: 4917: 4913: 4860: 4856: 4809: 4805: 4774: 4770: 4739: 4735: 4688: 4684: 4647: 4643: 4612: 4608: 4571: 4567: 4542: 4520: 4516: 4493: 4489: 4450: 4446: 4401: 4397: 4358: 4354: 4315: 4311: 4266: 4262: 4225: 4221: 4211: 4209: 4205: 4158: 4152: 4148: 4101: 4097: 4049: 4045: 4014:(11): 560–563. 4000: 3996: 3971:10.1038/nrm2330 3951: 3947: 3916: 3912: 3869: 3865: 3849: 3845: 3784: 3780: 3735: 3731: 3686: 3682: 3635: 3631: 3621: 3577: 3570: 3539: 3535: 3504: 3500: 3469: 3465: 3434: 3425: 3394: 3390: 3383: 3369: 3365: 3334: 3330: 3299: 3295: 3258: 3254: 3217: 3213: 3182: 3178: 3147: 3143: 3136: 3121: 3115: 3111: 3080: 3076: 3061: 3039: 3035: 3004: 3000: 2953: 2949: 2939: 2937: 2928: 2927: 2923: 2884: 2880: 2849: 2842: 2835: 2819: 2812: 2781: 2777: 2762: 2740: 2736: 2727: 2726: 2722: 2707: 2703: 2674:(11): 967–992. 2664: 2660: 2653: 2639: 2632: 2597: 2593: 2586: 2566: 2562: 2555: 2541: 2537: 2530: 2516: 2512: 2499: 2495: 2476: 2472: 2465: 2449: 2445: 2410: 2406: 2387: 2383: 2376: 2360: 2356: 2341: 2337: 2327: 2325: 2310: 2306: 2299: 2295: 2280: 2276: 2269: 2253: 2249: 2242: 2226: 2217: 2204: 2200: 2181: 2177: 2170: 2154: 2150: 2140: 2092: 2088: 2043: 2039: 1992: 1981: 1974: 1960: 1937: 1930: 1916: 1912: 1908: 1880: 1846: 1731: 1716: 1712: 1687:dehydrogenation 1668: 1531: 1522: 1489:Acyl-carnitines 1465: 1463:Other functions 1385:lipid signaling 1381: 1352: 1223:plasma membrane 1204: 1199: 1123: 1116: 1059: 1050: 977:Prenol lipid (2 971: 951:glucocorticoids 949:as well as the 868: 851: 835:glycosidic bond 784: 778: 685: 679: 617: 613: 609: 600: 553:, that include 453:carboxylic acid 421: 402: 392: 386: 374: 292:Theodore Gobley 219:Henri Braconnot 215: 125:food industries 17: 12: 11: 5: 8869: 8859: 8858: 8853: 8838: 8837: 8825: 8802: 8801: 8799: 8798: 8793: 8788: 8783: 8778: 8773: 8768: 8763: 8758: 8753: 8748: 8743: 8737: 8734: 8733: 8730:Food chemistry 8726: 8725: 8718: 8711: 8703: 8694: 8693: 8690: 8689: 8687: 8686: 8681: 8676: 8675: 8674: 8663: 8661: 8657: 8656: 8653: 8652: 8650: 8649: 8644: 8639: 8634: 8629: 8623: 8621: 8617: 8616: 8614: 8613: 8608: 8605:Beta oxidation 8597: 8595: 8586: 8570: 8569: 8566: 8565: 8562: 8561: 8559: 8558: 8553: 8547: 8544: 8543: 8541: 8540: 8535: 8530: 8525: 8523:Chemosynthesis 8520: 8515: 8513:Photosynthesis 8509: 8503: 8499: 8498: 8495: 8494: 8492: 8491: 8490: 8489: 8484: 8473: 8470: 8469: 8467: 8466: 8465: 8464: 8462:Leloir pathway 8454: 8453: 8452: 8450:Polyol pathway 8442: 8436: 8433: 8432: 8430: 8429: 8423:Glycogenolysis 8419: 8416: 8415: 8413: 8412: 8402: 8396: 8389: 8372: 8371: 8368: 8367: 8365: 8364: 8359: 8354: 8349: 8343: 8341: 8333: 8332: 8330: 8329: 8324: 8318: 8312: 8310: 8301: 8300: 8294: 8288: 8286: 8277: 8271: 8270: 8267: 8266: 8264: 8263: 8262: 8261: 8256: 8251: 8236: 8234: 8228: 8227: 8225: 8224: 8220: 8218: 8212: 8211: 8209: 8208: 8179: 8177: 8168: 8160: 8159: 8157: 8156: 8151: 8146: 8140: 8138: 8134: 8133: 8118: 8117: 8110: 8103: 8095: 8086: 8085: 8083: 8082: 8076: 8074: 8070: 8069: 8066: 8065: 8063: 8062: 8056: 8054: 8047: 8046: 8044: 8043: 8037: 8035: 8028: 8027: 8025: 8024: 8018: 8016: 8009: 8008: 8006: 8005: 7999: 7997: 7990: 7989: 7987: 7986: 7981: 7976: 7971: 7965: 7963: 7953: 7945: 7944: 7942: 7941: 7936: 7935: 7934: 7929: 7918: 7916: 7910: 7909: 7882: 7881: 7874: 7867: 7859: 7850: 7849: 7846: 7845: 7843: 7842: 7837: 7835:Phosphocholine 7832: 7826: 7823: 7822: 7820: 7819: 7813: 7810: 7809: 7807: 7806: 7801: 7795: 7789: 7785: 7784: 7782: 7781: 7775: 7773: 7766: 7765: 7762: 7761: 7759: 7758: 7752: 7749: 7748: 7746: 7745: 7744: 7743: 7732: 7730: 7723: 7722: 7720: 7719: 7715: 7711: 7710: 7709: 7705: 7701: 7697: 7693: 7689: 7682: 7679: 7678: 7677: 7672: 7667: 7658: 7656: 7652: 7651: 7649: 7648: 7647: 7646: 7638:-inositol (PI) 7635: 7633:-glycerol (PG) 7630: 7625: 7620: 7614: 7612: 7602: 7587: 7586: 7575: 7574: 7567: 7560: 7552: 7543: 7542: 7540: 7539: 7534: 7529: 7523: 7521: 7513: 7512: 7510: 7509: 7504: 7498: 7497: 7496: 7491: 7486: 7481: 7476: 7471: 7466: 7461: 7456: 7451: 7446: 7441: 7429: 7428: 7421: 7419: 7413: 7412: 7410: 7409: 7404: 7399: 7393: 7391: 7385: 7384: 7382: 7381: 7376: 7371: 7365: 7363: 7359:Extracellular 7356: 7355: 7353: 7352: 7351: 7350: 7340: 7335: 7330: 7325: 7324: 7323: 7318: 7313: 7308: 7300: 7295: 7294: 7293: 7288: 7283: 7278: 7269: 7267: 7261: 7260: 7253: 7251: 7249: 7248: 7243: 7238: 7233: 7230: 7227: 7222: 7208: 7203: 7192: 7190: 7189:and subclasses 7181: 7180: 7168: 7167: 7160: 7153: 7145: 7136: 7135: 7133: 7132: 7126: 7120: 7117:4-Hexadecenoic 7113: 7111: 7105: 7104: 7102: 7101: 7094: 7092: 7086: 7085: 7083: 7082: 7075: 7073: 7067: 7066: 7064: 7063: 7057: 7051: 7045: 7039: 7033: 7023: 7016: 7014: 7008: 7007: 7005: 7004: 6998: 6992: 6986: 6980: 6973: 6971: 6965: 6964: 6962: 6961: 6955: 6949: 6943: 6937: 6931: 6925: 6919: 6913: 6907: 6897: 6891: 6885: 6878: 6876: 6870: 6869: 6867: 6866: 6860: 6854: 6848: 6842: 6832: 6826: 6820: 6813: 6811: 6805: 6804: 6802: 6801: 6795: 6789: 6783: 6777: 6771: 6765: 6759: 6753: 6747: 6741: 6735: 6729: 6723: 6717: 6711: 6705: 6699: 6693: 6687: 6680: 6678: 6672: 6671: 6669: 6668: 6665:Tetracontanoic 6662: 6656: 6650: 6644: 6638: 6632: 6626: 6620: 6614: 6608: 6602: 6596: 6590: 6584: 6578: 6572: 6566: 6560: 6554: 6548: 6542: 6536: 6530: 6524: 6518: 6512: 6506: 6500: 6494: 6488: 6482: 6476: 6470: 6464: 6458: 6452: 6446: 6439: 6437: 6431: 6430: 6419: 6418: 6411: 6404: 6396: 6387: 6386: 6384: 6383: 6378: 6373: 6368: 6362: 6360: 6354: 6353: 6351: 6350: 6344: 6342: 6336: 6335: 6333: 6332: 6327: 6322: 6317: 6312: 6306: 6304: 6298: 6297: 6295: 6294: 6293: 6292: 6287: 6282: 6277: 6272: 6267: 6257: 6252: 6246: 6244: 6238: 6237: 6235: 6234: 6229: 6224: 6222:Arachidic acid 6219: 6214: 6209: 6204: 6199: 6194: 6188: 6186: 6180: 6179: 6177: 6176: 6171: 6166: 6161: 6159:Prostaglandins 6156: 6150: 6148: 6142: 6141: 6139: 6138: 6133: 6128: 6123: 6117: 6115: 6111: 6110: 6108: 6107: 6102: 6093: 6088: 6083: 6078: 6073: 6063: 6061: 6057: 6056: 6048: 6047: 6040: 6033: 6025: 6019: 6018: 6012: 6000: 5999: 5993: 5981: 5980: 5975: 5964: 5963: 5957: 5951: 5948:Cyberlipid.org 5945: 5939: 5933: 5921: 5920:External links 5918: 5917: 5916: 5910: 5895: 5889: 5876: 5870: 5857: 5851: 5834: 5831: 5829: 5828: 5814: 5796: 5753: 5727:(6): 643–654. 5710: 5691:(5): 575–577. 5675: 5632: 5590: 5563:(6): 486–493. 5547: 5536:(2): 146–156. 5520: 5471: 5428: 5409:(4): 668–679. 5393: 5374:(6): 937–946. 5358: 5351: 5328: 5301:(3): 221–226. 5285: 5247: 5212: 5163: 5120: 5085: 5042: 5012: 4960: 4931:(4): 469–472. 4911: 4854: 4803: 4768: 4749:(1): 110–116. 4733: 4682: 4661:(4): 297–316. 4641: 4622:(5): 335–349. 4606: 4565: 4540: 4514: 4487: 4444: 4409:Bioinformatics 4395: 4368:(3): 329–336. 4352: 4325:(3): 227–230. 4309: 4280:(8): 886–893. 4260: 4219: 4146: 4095: 4066:(4): 432–449. 4043: 3994: 3965:(2): 112–124. 3945: 3926:(4): 281–288. 3910: 3863: 3843: 3778: 3749:(4): 233–306. 3729: 3700:(8): 639–653. 3680: 3629: 3568: 3549:(4): 235–258. 3533: 3514:(4): 435–477. 3498: 3479:(3): 207–216. 3463: 3444:(2): 171–183. 3423: 3404:(4): 627–645. 3388: 3381: 3373:Fungal Biology 3363: 3344:(5): 567–588. 3328: 3293: 3272:(2): 187–197. 3252: 3211: 3192:(2): 117–126. 3176: 3141: 3134: 3109: 3090:(2): 101–139. 3074: 3059: 3033: 2998: 2947: 2921: 2894:(1–2): 59–62. 2878: 2859:(5): 225–243. 2840: 2833: 2810: 2791:(2): 134–176. 2775: 2760: 2734: 2720: 2701: 2658: 2651: 2630: 2611:(6): 177–178. 2591: 2584: 2560: 2553: 2535: 2528: 2510: 2493: 2470: 2464:978-0857097866 2463: 2443: 2424:(6): 138–140. 2404: 2381: 2375:978-1483164793 2374: 2354: 2335: 2304: 2293: 2274: 2268:978-1482242317 2267: 2247: 2241:978-1466551466 2240: 2215: 2198: 2175: 2168: 2148: 2086: 2037: 1979: 1972: 1935: 1928: 1909: 1907: 1904: 1903: 1902: 1899:Phenolic lipid 1896: 1891: 1890: 1889: 1874: 1871:Membrane lipid 1868: 1863: 1858: 1853: 1845: 1842: 1771:vegetable oils 1730: 1727: 1714: 1710: 1699:beta-keto acid 1671:Beta oxidation 1667: 1664: 1539:esterification 1530: 1527: 1521: 1518: 1493:beta oxidation 1464: 1461: 1421:prostaglandins 1409:diacylglycerol 1389:cell signaling 1380: 1377: 1351: 1350:Energy storage 1348: 1329:hydrogen bonds 1321:Phase behavior 1313:lipid bilayers 1282:lamellar phase 1264:: a spherical 1203: 1200: 1198: 1195: 1122: 1119: 1114: 1085:monosaccharide 1081:Saccharolipids 1057: 1049: 1048:Saccharolipids 1046: 998:mevalonic acid 970: 967: 919:hydroxyl group 892:brassicasterol 864:Main article: 850: 847: 827:sphingomyelins 798:sphingoid base 780:Main article: 777: 774: 731:archaebacteria 715:cell signaling 703:sphingomyelins 681:Main article: 678: 675: 663:sugar residues 656:adipose tissue 618:). Left part: 615: 611: 607: 599: 596: 586:, such as the 555:prostaglandins 518:linolenic acid 419: 403:– Prostacyclin 400: 388:Main article: 385: 382: 373: 370: 366:T. P. Hilditch 214: 211: 176:saccharolipids 129:nanotechnology 117:cell membranes 101:monoglycerides 15: 9: 6: 4: 3: 2: 8868: 8857: 8854: 8852: 8849: 8848: 8846: 8836: 8831: 8826: 8824: 8819: 8814: 8813: 8810: 8797: 8794: 8792: 8789: 8787: 8784: 8782: 8779: 8777: 8774: 8772: 8771:Fortification 8769: 8767: 8764: 8762: 8759: 8757: 8754: 8752: 8749: 8747: 8746:Carbohydrates 8744: 8742: 8739: 8738: 8735: 8731: 8724: 8719: 8717: 8712: 8710: 8705: 8704: 8701: 8685: 8682: 8680: 8677: 8673: 8670: 8669: 8668: 8665: 8664: 8662: 8658: 8648: 8645: 8643: 8640: 8638: 8635: 8633: 8630: 8628: 8625: 8624: 8622: 8618: 8612: 8609: 8606: 8602: 8599: 8598: 8596: 8594: 8590: 8587: 8584: 8580: 8575: 8571: 8557: 8556:Radiotrophism 8554: 8552: 8549: 8548: 8545: 8539: 8536: 8534: 8531: 8529: 8526: 8524: 8521: 8519: 8516: 8514: 8511: 8510: 8507: 8504: 8500: 8488: 8485: 8483: 8480: 8479: 8478: 8477:Glycosylation 8475: 8474: 8471: 8463: 8460: 8459: 8458: 8455: 8451: 8448: 8447: 8446: 8443: 8441: 8438: 8437: 8434: 8428: 8424: 8421: 8420: 8417: 8411: 8407: 8404: 8403: 8400: 8397: 8393: 8390: 8387: 8382: 8377: 8373: 8363: 8360: 8358: 8355: 8353: 8350: 8348: 8345: 8344: 8342: 8340: 8334: 8328: 8325: 8322: 8319: 8317: 8314: 8313: 8311: 8309: 8305: 8298: 8295: 8293: 8290: 8289: 8287: 8285: 8281: 8278: 8272: 8260: 8257: 8255: 8252: 8250: 8247: 8246: 8245: 8241: 8238: 8237: 8235: 8233: 8229: 8222: 8221: 8219: 8217: 8213: 8205: 8201: 8196: 8192: 8188: 8184: 8181: 8180: 8178: 8176: 8172: 8169: 8167: 8161: 8155: 8152: 8150: 8147: 8145: 8142: 8141: 8139: 8135: 8131: 8127: 8123: 8116: 8111: 8109: 8104: 8102: 8097: 8096: 8093: 8081: 8078: 8077: 8075: 8071: 8061: 8058: 8057: 8055: 8053: 8048: 8042: 8039: 8038: 8036: 8034: 8029: 8023: 8020: 8019: 8017: 8015: 8014:sphingomyelin 8010: 8004: 8001: 8000: 7998: 7996: 7991: 7985: 7982: 7980: 7977: 7975: 7972: 7970: 7967: 7966: 7964: 7962: 7957: 7954: 7950: 7946: 7940: 7937: 7933: 7930: 7928: 7925: 7924: 7923: 7920: 7919: 7917: 7915: 7911: 7907: 7903: 7899: 7898:sphingolipids 7895: 7891: 7887: 7880: 7875: 7873: 7868: 7866: 7861: 7860: 7857: 7841: 7838: 7836: 7833: 7831: 7828: 7827: 7824: 7818: 7815: 7814: 7811: 7805: 7802: 7800: 7797: 7796: 7793: 7790: 7786: 7780: 7779:Sphingomyelin 7777: 7776: 7774: 7771: 7767: 7757: 7754: 7753: 7750: 7742: 7739: 7738: 7737: 7734: 7733: 7731: 7728: 7724: 7718: 7712: 7708: 7702: 7700: 7694: 7692: 7686: 7685: 7680: 7676: 7673: 7671: 7668: 7666: 7663: 7662: 7660: 7659: 7657: 7653: 7644: 7641: 7640: 7639: 7636: 7634: 7631: 7629: 7626: 7624: 7621: 7619: 7616: 7615: 7613: 7610: 7609:Phosphatidyl- 7606: 7603: 7600: 7592: 7588: 7584: 7583:phospholipids 7580: 7573: 7568: 7566: 7561: 7559: 7554: 7553: 7550: 7538: 7535: 7533: 7530: 7528: 7525: 7524: 7522: 7520: 7514: 7508: 7505: 7503: 7499: 7495: 7492: 7490: 7487: 7485: 7482: 7480: 7477: 7475: 7472: 7470: 7467: 7465: 7462: 7460: 7457: 7455: 7452: 7450: 7447: 7445: 7442: 7440: 7437: 7436: 7435: 7431: 7430: 7427: 7423: 7422: 7420: 7418: 7414: 7408: 7405: 7403: 7400: 7398: 7395: 7394: 7392: 7390: 7386: 7380: 7377: 7375: 7372: 7370: 7367: 7366: 7364: 7362: 7357: 7349: 7346: 7345: 7344: 7341: 7339: 7336: 7334: 7331: 7329: 7326: 7322: 7319: 7317: 7314: 7312: 7309: 7307: 7304: 7303: 7301: 7299: 7296: 7292: 7289: 7287: 7284: 7282: 7279: 7277: 7274: 7273: 7271: 7270: 7268: 7266: 7262: 7257: 7247: 7244: 7242: 7239: 7237: 7234: 7231: 7228: 7226: 7223: 7221: 7217: 7213: 7209: 7207: 7204: 7202: 7198: 7194: 7193: 7191: 7186: 7182: 7177: 7173: 7166: 7161: 7159: 7154: 7152: 7147: 7146: 7143: 7130: 7127: 7124: 7121: 7118: 7115: 7114: 7112: 7110: 7106: 7099: 7096: 7095: 7093: 7091: 7087: 7080: 7077: 7076: 7074: 7072: 7068: 7061: 7058: 7055: 7052: 7049: 7046: 7043: 7040: 7037: 7034: 7031: 7027: 7024: 7021: 7018: 7017: 7015: 7013: 7009: 7002: 6999: 6996: 6993: 6990: 6987: 6984: 6981: 6978: 6975: 6974: 6972: 6970: 6966: 6959: 6956: 6953: 6950: 6947: 6944: 6941: 6938: 6935: 6932: 6929: 6926: 6923: 6920: 6917: 6914: 6911: 6908: 6905: 6901: 6898: 6895: 6892: 6889: 6886: 6883: 6880: 6879: 6877: 6875: 6871: 6864: 6861: 6858: 6855: 6852: 6849: 6846: 6843: 6840: 6836: 6835:β-Eleostearic 6833: 6830: 6829:α-Eleostearic 6827: 6824: 6821: 6818: 6815: 6814: 6812: 6810: 6806: 6799: 6796: 6793: 6790: 6787: 6784: 6781: 6778: 6775: 6772: 6769: 6766: 6763: 6760: 6757: 6754: 6751: 6748: 6745: 6742: 6739: 6736: 6733: 6730: 6727: 6724: 6721: 6718: 6715: 6712: 6709: 6708:Laurolinoleic 6706: 6703: 6700: 6697: 6694: 6691: 6688: 6685: 6682: 6681: 6679: 6677: 6673: 6666: 6663: 6660: 6657: 6654: 6651: 6648: 6645: 6642: 6639: 6636: 6633: 6630: 6627: 6624: 6621: 6618: 6615: 6612: 6609: 6606: 6603: 6600: 6597: 6594: 6591: 6588: 6585: 6582: 6579: 6576: 6573: 6570: 6567: 6564: 6561: 6558: 6555: 6552: 6549: 6546: 6543: 6540: 6537: 6534: 6531: 6528: 6525: 6522: 6519: 6516: 6513: 6510: 6507: 6504: 6501: 6498: 6495: 6492: 6489: 6486: 6483: 6480: 6477: 6474: 6471: 6468: 6465: 6462: 6459: 6456: 6453: 6450: 6447: 6444: 6441: 6440: 6438: 6436: 6432: 6428: 6424: 6417: 6412: 6410: 6405: 6403: 6398: 6397: 6394: 6382: 6379: 6377: 6374: 6372: 6369: 6367: 6364: 6363: 6361: 6359: 6355: 6349: 6346: 6345: 6343: 6341: 6340:Sphingolipids 6337: 6331: 6328: 6326: 6323: 6321: 6318: 6316: 6313: 6311: 6308: 6307: 6305: 6303: 6302:Phospholipids 6299: 6291: 6288: 6286: 6283: 6281: 6278: 6276: 6273: 6271: 6268: 6266: 6263: 6262: 6261: 6258: 6256: 6253: 6251: 6250:Monoglyceride 6248: 6247: 6245: 6243: 6239: 6233: 6230: 6228: 6225: 6223: 6220: 6218: 6215: 6213: 6212:Palmitic acid 6210: 6208: 6207:Myristic acid 6205: 6203: 6200: 6198: 6195: 6193: 6192:Caprylic acid 6190: 6189: 6187: 6185: 6181: 6175: 6172: 6170: 6167: 6165: 6162: 6160: 6157: 6155: 6152: 6151: 6149: 6147: 6143: 6137: 6134: 6132: 6129: 6127: 6124: 6122: 6119: 6118: 6116: 6112: 6106: 6103: 6101: 6097: 6094: 6092: 6089: 6087: 6084: 6082: 6079: 6077: 6074: 6072: 6071:Saturated fat 6068: 6065: 6064: 6062: 6058: 6054: 6046: 6041: 6039: 6034: 6032: 6027: 6026: 6023: 6016: 6013: 6010: 6007: 6006: 6005: 6004: 5997: 5994: 5991: 5988: 5987: 5986: 5985: 5979: 5976: 5974: 5971: 5970: 5969: 5968: 5961: 5958: 5955: 5952: 5949: 5946: 5943: 5942:Lipid Library 5940: 5937: 5934: 5932: 5929: 5928: 5927: 5926: 5913: 5907: 5903: 5902: 5896: 5892: 5886: 5882: 5877: 5873: 5867: 5863: 5858: 5854: 5848: 5844: 5843: 5837: 5836: 5824: 5818: 5810: 5806: 5800: 5792: 5785: 5781: 5777: 5773: 5769: 5765: 5757: 5749: 5742: 5738: 5734: 5730: 5726: 5722: 5714: 5706: 5702: 5698: 5694: 5690: 5686: 5679: 5671: 5667: 5663: 5659: 5655: 5651: 5647: 5643: 5636: 5629: 5625: 5621: 5617: 5613: 5609: 5606:(S1): 48–52, 5605: 5601: 5594: 5586: 5582: 5578: 5574: 5570: 5566: 5562: 5558: 5551: 5543: 5539: 5535: 5531: 5524: 5516: 5512: 5507: 5502: 5498: 5494: 5490: 5486: 5482: 5475: 5467: 5463: 5459: 5455: 5451: 5447: 5443: 5439: 5432: 5424: 5420: 5416: 5412: 5408: 5404: 5397: 5389: 5385: 5381: 5377: 5373: 5369: 5362: 5354: 5348: 5344: 5343: 5335: 5333: 5324: 5320: 5316: 5312: 5308: 5304: 5300: 5296: 5289: 5281: 5277: 5273: 5269: 5265: 5261: 5254: 5252: 5243: 5239: 5235: 5231: 5227: 5223: 5216: 5208: 5204: 5199: 5194: 5190: 5186: 5182: 5178: 5174: 5167: 5159: 5155: 5151: 5147: 5143: 5139: 5135: 5131: 5124: 5116: 5112: 5108: 5104: 5100: 5096: 5089: 5081: 5077: 5073: 5069: 5065: 5061: 5057: 5053: 5046: 5030: 5026: 5025:Elmhurst. edu 5022: 5016: 5008: 5004: 4999: 4998:2027.42/30145 4994: 4990: 4986: 4983:(1): 71–133. 4982: 4978: 4971: 4964: 4956: 4952: 4947: 4942: 4938: 4934: 4930: 4926: 4922: 4915: 4907: 4903: 4899: 4895: 4890: 4885: 4881: 4877: 4873: 4869: 4865: 4858: 4850: 4846: 4842: 4838: 4834: 4830: 4826: 4822: 4818: 4814: 4807: 4799: 4795: 4791: 4787: 4783: 4779: 4772: 4764: 4760: 4756: 4752: 4748: 4744: 4737: 4729: 4725: 4721: 4717: 4713: 4709: 4705: 4701: 4698:(6): 065007. 4697: 4693: 4686: 4678: 4674: 4669: 4664: 4660: 4656: 4652: 4645: 4637: 4633: 4629: 4625: 4621: 4617: 4610: 4602: 4598: 4593: 4588: 4584: 4580: 4576: 4569: 4561: 4557: 4552: 4547: 4543: 4537: 4533: 4529: 4525: 4518: 4510: 4506: 4502: 4498: 4491: 4483: 4479: 4475: 4471: 4467: 4463: 4459: 4455: 4448: 4440: 4436: 4431: 4426: 4422: 4418: 4414: 4410: 4406: 4399: 4391: 4387: 4383: 4379: 4375: 4371: 4367: 4363: 4356: 4348: 4344: 4340: 4336: 4332: 4328: 4324: 4320: 4313: 4305: 4301: 4296: 4291: 4287: 4283: 4279: 4275: 4271: 4264: 4256: 4252: 4247: 4242: 4238: 4234: 4230: 4223: 4204: 4200: 4196: 4192: 4188: 4184: 4180: 4176: 4172: 4168: 4164: 4157: 4150: 4142: 4138: 4133: 4128: 4123: 4118: 4114: 4110: 4106: 4099: 4091: 4087: 4082: 4077: 4073: 4069: 4065: 4061: 4057: 4053: 4047: 4039: 4035: 4030: 4025: 4021: 4017: 4013: 4009: 4005: 3998: 3990: 3986: 3981: 3976: 3972: 3968: 3964: 3960: 3956: 3949: 3941: 3937: 3933: 3929: 3925: 3921: 3914: 3906: 3902: 3898: 3894: 3890: 3886: 3882: 3878: 3875:assembling". 3874: 3867: 3861: 3857: 3853: 3847: 3839: 3835: 3831: 3827: 3823: 3819: 3814: 3809: 3805: 3801: 3797: 3793: 3789: 3782: 3774: 3770: 3765: 3760: 3756: 3752: 3748: 3744: 3740: 3733: 3725: 3721: 3716: 3711: 3707: 3703: 3699: 3695: 3691: 3684: 3676: 3672: 3668: 3664: 3660: 3656: 3652: 3648: 3644: 3640: 3633: 3625: 3618: 3614: 3609: 3604: 3599: 3594: 3590: 3586: 3582: 3575: 3573: 3564: 3560: 3556: 3552: 3548: 3544: 3537: 3529: 3525: 3521: 3517: 3513: 3509: 3502: 3494: 3490: 3486: 3482: 3478: 3474: 3467: 3459: 3455: 3451: 3447: 3443: 3439: 3432: 3430: 3428: 3419: 3415: 3411: 3407: 3403: 3399: 3392: 3384: 3378: 3374: 3367: 3359: 3355: 3351: 3347: 3343: 3339: 3332: 3324: 3320: 3316: 3312: 3308: 3304: 3297: 3289: 3285: 3280: 3275: 3271: 3267: 3263: 3256: 3248: 3244: 3239: 3234: 3230: 3226: 3222: 3215: 3207: 3203: 3199: 3195: 3191: 3187: 3180: 3172: 3168: 3164: 3160: 3156: 3152: 3145: 3137: 3131: 3127: 3120: 3113: 3105: 3101: 3097: 3093: 3089: 3085: 3078: 3070: 3066: 3062: 3056: 3052: 3048: 3044: 3037: 3029: 3025: 3021: 3017: 3013: 3009: 3002: 2994: 2990: 2986: 2982: 2978: 2974: 2970: 2966: 2962: 2958: 2951: 2935: 2931: 2925: 2917: 2913: 2909: 2905: 2901: 2897: 2893: 2889: 2882: 2874: 2870: 2866: 2862: 2858: 2854: 2847: 2845: 2836: 2830: 2826: 2825: 2817: 2815: 2806: 2802: 2798: 2794: 2790: 2786: 2779: 2771: 2767: 2763: 2757: 2753: 2749: 2745: 2738: 2730: 2724: 2716: 2712: 2705: 2697: 2693: 2689: 2685: 2681: 2677: 2673: 2669: 2662: 2654: 2648: 2644: 2637: 2635: 2626: 2622: 2618: 2614: 2610: 2606: 2602: 2595: 2587: 2581: 2577: 2573: 2572: 2564: 2556: 2550: 2546: 2539: 2531: 2525: 2521: 2514: 2506: 2505: 2497: 2489: 2485: 2481: 2474: 2466: 2460: 2456: 2455: 2447: 2439: 2435: 2431: 2427: 2423: 2419: 2415: 2408: 2400: 2396: 2395:Biochem. Bull 2392: 2385: 2377: 2371: 2367: 2366: 2358: 2350: 2346: 2339: 2323: 2319: 2315: 2308: 2302: 2297: 2289: 2285: 2278: 2270: 2264: 2260: 2259: 2251: 2243: 2237: 2233: 2232: 2224: 2222: 2220: 2211: 2210: 2202: 2194: 2190: 2186: 2179: 2171: 2165: 2161: 2160: 2152: 2144: 2137: 2133: 2128: 2123: 2118: 2113: 2109: 2105: 2101: 2097: 2090: 2082: 2078: 2073: 2068: 2064: 2060: 2056: 2052: 2048: 2041: 2033: 2029: 2024: 2019: 2014: 2009: 2006:(S1): S9–14. 2005: 2001: 1997: 1990: 1988: 1986: 1984: 1975: 1969: 1965: 1958: 1956: 1954: 1952: 1950: 1948: 1946: 1944: 1942: 1940: 1931: 1925: 1921: 1914: 1910: 1900: 1897: 1895: 1892: 1887: 1884: 1883: 1878: 1875: 1872: 1869: 1867: 1864: 1862: 1861:Emulsion test 1859: 1857: 1854: 1851: 1848: 1847: 1841: 1839: 1835: 1829: 1827: 1823: 1819: 1814: 1812: 1808: 1804: 1800: 1796: 1792: 1788: 1784: 1780: 1776: 1772: 1768: 1764: 1760: 1756: 1755:linoleic acid 1752: 1748: 1744: 1740: 1736: 1726: 1724: 1720: 1708: 1704: 1700: 1696: 1692: 1688: 1684: 1680: 1676: 1672: 1663: 1661: 1657: 1653: 1649: 1645: 1641: 1637: 1633: 1629: 1625: 1621: 1617: 1613: 1611: 1606: 1604: 1600: 1596: 1595:linoleic acid 1592: 1588: 1584: 1580: 1576: 1571: 1569: 1565: 1560: 1556: 1552: 1548: 1544: 1540: 1536: 1526: 1517: 1515: 1510: 1506: 1505:glycosylation 1502: 1501:peptidoglycan 1498: 1494: 1490: 1486: 1482: 1478: 1474: 1470: 1460: 1457: 1453: 1450: 1446: 1442: 1438: 1434: 1430: 1426: 1422: 1418: 1414: 1410: 1406: 1402: 1398: 1394: 1390: 1386: 1376: 1374: 1370: 1366: 1362: 1361:carbohydrates 1358: 1347: 1345: 1341: 1336: 1334: 1330: 1326: 1322: 1318: 1314: 1310: 1306: 1302: 1301:concentration 1298: 1294: 1290: 1286: 1285:lipid bilayer 1283: 1275: 1274:lipid bilayer 1271: 1267: 1263: 1262:phospholipids 1258: 1254: 1250: 1248: 1244: 1243:sphingomyelin 1240: 1236: 1232: 1231:extracellular 1228: 1227:intracellular 1224: 1220: 1216: 1212: 1208: 1194: 1192: 1188: 1184: 1183:tetracyclines 1180: 1179:erythromycins 1176: 1172: 1171:antiparasitic 1168: 1167:antimicrobial 1164: 1160: 1159:hydroxylation 1156: 1152: 1151:glycosylation 1148: 1144: 1140: 1136: 1132: 1128: 1118: 1112: 1111: 1106: 1105:disaccharides 1102: 1098: 1094: 1090: 1086: 1082: 1075: 1071: 1067: 1063: 1054: 1045: 1043: 1039: 1035: 1031: 1027: 1023: 1022:hydroquinones 1019: 1015: 1011: 1007: 1003: 999: 995: 991: 987: 980: 975: 966: 964: 960: 956: 952: 948: 944: 940: 936: 932: 928: 924: 920: 916: 911: 909: 905: 901: 897: 893: 889: 885: 881: 877: 873: 867: 860: 855: 846: 844: 840: 836: 832: 828: 823: 821: 817: 813: 809: 805: 804: 799: 792: 791:Sphingomyelin 788: 783: 776:Sphingolipids 773: 771: 767: 763: 759: 755: 751: 747: 743: 739: 734: 732: 728: 724: 720: 716: 712: 708: 707:lipid bilayer 704: 700: 699:phospholipids 693: 689: 684: 674: 672: 668: 664: 659: 657: 653: 649: 648:triglycerides 645: 641: 633: 629: 625: 624:palmitic acid 621: 604: 598:Glycerolipids 595: 593: 589: 585: 581: 577: 573: 568: 564: 560: 556: 552: 548: 544: 539: 537: 533: 528: 524: 520: 519: 514: 510: 509:configuration 506: 503: 499: 495: 491: 487: 483: 479: 475: 470: 466: 462: 458: 454: 450: 446: 442: 438: 434: 426: 422: 415: 408: 407:prostaglandin 404: 396: 391: 381: 379: 369: 367: 362: 360: 356: 352: 348: 344: 340: 336: 332: 327: 325: 320: 315: 313: 312:sphingomyelin 309: 305: 301: 297: 293: 288: 286: 285:William Prout 281: 279: 275: 271: 267: 263: 259: 258:sulfuric acid 255: 251: 247: 243: 238: 236: 232: 228: 224: 220: 210: 208: 204: 200: 196: 192: 188: 187:triglycerides 183: 181: 177: 173: 172:sphingolipids 169: 165: 164:glycerolipids 161: 157: 153: 149: 145: 141: 137: 132: 130: 126: 122: 118: 114: 110: 109:phospholipids 106: 102: 98: 94: 90: 86: 82: 78: 74: 70: 66: 59: 56: 52: 48: 44: 40: 36: 32: 28: 23: 19: 8775: 8457:Galactolysis 8427:Glycogenesis 8232:Fermentation 8204:ATP synthase 7889: 7727:Ether lipids 7628:-serine (PS) 7578: 7517:ATP-binding 7210:delivery of 7195:delivery of 7171: 7129:8-Eicosenoic 7123:Petroselinic 7029: 6903: 6900:Linolelaidic 6838: 6780:Clupanodonic 6738:Palmitidonic 6575:Pentacosylic 6551:Heneicosylic 6515:Pentadecylic 6422: 6381:Secosteroids 6376:Sex steroids 6265:Triheptanoin 6260:Triglyceride 6227:Behenic acid 6217:Stearic acid 6174:Leukotrienes 6164:Prostacyclin 6095: 6066: 6052: 6009:ApolloLipids 6002: 6001: 5983: 5982: 5967:Nomenclature 5966: 5965: 5925:Introductory 5924: 5923: 5901:Biochemistry 5900: 5881:Biochemistry 5880: 5861: 5841: 5833:Bibliography 5817: 5808: 5799: 5770:(1): 39–49. 5767: 5763: 5756: 5724: 5720: 5713: 5688: 5684: 5678: 5648:(1): 40–47. 5645: 5641: 5635: 5603: 5599: 5593: 5560: 5556: 5550: 5533: 5529: 5523: 5488: 5484: 5474: 5444:(1): 11–20. 5441: 5437: 5431: 5406: 5402: 5396: 5371: 5367: 5361: 5341: 5298: 5294: 5288: 5263: 5259: 5225: 5221: 5215: 5180: 5176: 5166: 5133: 5129: 5123: 5098: 5094: 5088: 5055: 5051: 5045: 5033:. Retrieved 5029:the original 5024: 5015: 4980: 4976: 4963: 4928: 4924: 4914: 4871: 4868:FEBS Letters 4867: 4857: 4816: 4812: 4806: 4781: 4777: 4771: 4746: 4742: 4736: 4695: 4691: 4685: 4658: 4654: 4644: 4619: 4615: 4609: 4592:10.2741/2756 4582: 4578: 4568: 4523: 4517: 4500: 4496: 4490: 4457: 4453: 4447: 4412: 4408: 4398: 4365: 4361: 4355: 4322: 4318: 4312: 4277: 4273: 4263: 4236: 4232: 4222: 4210:. Retrieved 4203:the original 4166: 4162: 4149: 4112: 4108: 4098: 4063: 4059: 4046: 4011: 4007: 3997: 3962: 3958: 3948: 3923: 3919: 3913: 3880: 3876: 3872: 3866: 3851: 3846: 3795: 3791: 3781: 3746: 3742: 3732: 3697: 3693: 3683: 3642: 3638: 3632: 3588: 3584: 3546: 3542: 3536: 3511: 3507: 3501: 3476: 3472: 3466: 3441: 3437: 3401: 3397: 3391: 3372: 3366: 3341: 3337: 3331: 3306: 3302: 3296: 3269: 3265: 3255: 3238:10.2741/2923 3228: 3224: 3214: 3189: 3185: 3179: 3157:(1): 25–45. 3154: 3150: 3144: 3125: 3112: 3087: 3083: 3077: 3042: 3036: 3011: 3007: 3001: 2960: 2956: 2950: 2938:. Retrieved 2933: 2924: 2891: 2887: 2881: 2856: 2852: 2824:Biochemistry 2823: 2788: 2784: 2778: 2743: 2737: 2723: 2714: 2704: 2671: 2667: 2661: 2642: 2608: 2604: 2594: 2570: 2563: 2544: 2538: 2519: 2513: 2503: 2496: 2487: 2483: 2473: 2453: 2446: 2421: 2417: 2407: 2398: 2394: 2384: 2364: 2357: 2349:Phil. Trans. 2348: 2338: 2326:. Retrieved 2322:the original 2317: 2307: 2300: 2296: 2287: 2283: 2277: 2257: 2250: 2230: 2208: 2201: 2192: 2188: 2178: 2158: 2151: 2107: 2103: 2096:Koenderink G 2089: 2054: 2050: 2040: 2003: 1999: 1964:Biochemistry 1963: 1919: 1913: 1856:Simple lipid 1830: 1815: 1732: 1717:O using the 1681:to generate 1675:mitochondria 1669: 1614: 1607: 1583:stearic acid 1579:desaturation 1572: 1568:lipoproteins 1532: 1529:Biosynthesis 1523: 1509:Cardiolipins 1466: 1437:testosterone 1425:inflammation 1382: 1353: 1337: 1279: 1251: 1205: 1124: 1109: 1093:Lipid A 1079: 1038:bactoprenols 1010:antioxidants 984: 978: 959:secosteroids 947:progestogens 943:androsterone 939:testosterone 913:Sterols are 912: 888:stigmasterol 884:β-sitosterol 880:phytosterols 869: 843:gangliosides 839:cerebrosides 824: 802: 795: 782:Sphingolipid 735: 726: 718: 696: 660: 637: 563:thromboxanes 559:leukotrienes 540: 535: 531: 526: 522: 516: 512: 501: 497: 467:end that is 435:primer with 430: 375: 363: 358: 354: 350: 346: 342: 334: 330: 328: 326:, sterols). 316: 289: 282: 250:butyric acid 248:by treating 239: 230: 226: 222: 216: 197:-containing 184: 133: 105:diglycerides 64: 63: 55:phospholipid 37:composed of 35:triglyceride 18: 8583:lipogenesis 8445:Fructolysis 8259:Lactic acid 8052:sphingosine 7961:ganglioside 7949:Ganglioside 7922:Cerebroside 7894:glycolipids 7788:Metabolites 7770:Sphingosine 7756:Cardiolipin 7736:Plasmalogen 7201:Chylomicron 7185:Lipoprotein 7176:lipoprotein 6977:Palmitoleic 6946:Arachidonic 6910:γ-Linolenic 6817:Myristoleic 6756:α-Parinaric 6750:Stearidonic 6744:α-Linolenic 6696:Decadienoic 6635:Ceroplastic 6599:Nonacosylic 6539:Nonadecylic 6427:fatty acids 6366:Cholesterol 6325:Cardiolipin 6285:Trilinolein 6275:Tripalmitin 6270:Trimyristin 6255:Diglyceride 6202:Lauric acid 6197:Capric acid 6184:Fatty acids 6169:Thromboxane 6146:Eicosanoids 5266:: 585–621. 5136:: 109–136. 5101:: 791–831. 4784:(1): 1–37. 4460:(1): 5–16. 3792:Soft Matter 3608:10919/74310 3309:: 137–174. 3014:(1): 1–29. 2940:31 December 1751:carotenoids 1679:peroxisomes 1666:Degradation 1624:carotenoids 1620:isoprenoids 1577:involves a 1543:lipogenesis 1344:abiogenesis 1235:amphipathic 1191:epothilones 1187:avermectins 1155:methylation 1147:polyketides 1121:Polyketides 1089:glucosamine 1062:Glucosamine 1034:ubiquinones 1006:Carotenoids 872:cholesterol 859:cholesterol 816:sphingosine 770:plasmalogen 671:sperm cells 588:cannabinoid 543:eicosanoids 480:containing 474:unsaturated 465:hydrophobic 461:hydrophilic 437:malonyl-CoA 425:leukotriene 384:Fatty acyls 308:cerebroside 274:fatty acids 270:tripalmitin 203:cholesterol 199:metabolites 191:fatty acids 180:polyketides 160:fatty acyls 140:amphiphilic 136:hydrophobic 27:cholesterol 8845:Categories 8406:Glycolysis 8339:metabolism 8337:Nucleotide 8327:Urea cycle 8308:Amino acid 8297:Catabolism 8240:Glycolysis 8183:Glycolysis 8166:metabolism 8126:catabolism 8122:Metabolism 7840:Citicoline 6587:Carboceric 6569:Lignoceric 6563:Tricosylic 6503:Tridecylic 6479:Pelargonic 6280:Tristearin 6242:Glycerides 6067:Saturation 5990:LIPID MAPS 5035:10 October 5021:"Steroids" 4052:Wiggins PM 3715:10197/8333 2351:: 355–388. 2328:1 December 1906:References 1877:Lipidomics 1818:trans fats 1697:to form a 1683:acetyl-CoA 1660:lanosterol 1591:oleic acid 1535:acetyl-CoA 1520:Metabolism 1445:oxysterols 1325:biophysics 1317:amphiphile 1211:organelles 1207:Eukaryotic 1175:anticancer 1060:-lipid A. 981:-geraniol) 908:ergosterol 882:, such as 876:bile acids 723:eukaryotes 711:metabolism 628:oleic acid 592:anandamide 576:coenzyme A 572:wax esters 433:acetyl-CoA 390:Fatty acid 378:Lipid MAPS 372:Categories 266:tristearin 246:tributyrin 31:oleic acid 8741:Additives 8579:lipolysis 8386:anabolism 8130:anabolism 8033:sulfatide 7995:globoside 6995:Paullinic 6940:Sciadonic 6922:Pinolenic 6702:Lauroleic 6617:Lacceroic 6545:Arachidic 6491:Undecylic 6443:Propionic 6435:Saturated 6121:Trans fat 6051:Types of 5996:LipidBank 5984:Databases 5670:260372605 5228:: 47–65. 3905:232761961 3838:235708094 3822:1744-683X 2490:: 96–109. 2312:Leray C. 1803:Fish oils 1779:sunflower 1775:safflower 1709:(ATP), CO 1703:thiolysis 1695:oxidation 1691:hydration 1589:produces 1553:it to an 1551:dehydrate 1456:flippases 1379:Signaling 1369:adipocyte 1340:protocell 1333:clathrate 1309:liposomes 1239:phosphate 1163:oxidation 1131:propionyl 1074:phosphate 1042:dolichols 1030:vitamin K 1026:Vitamin E 1014:vitamin A 963:vitamin D 935:androgens 896:biomarker 812:ceramides 644:triesters 640:glycerols 469:insoluble 364:In 1947, 329:The word 300:Thudichum 296:lecithins 283:In 1827, 217:In 1815, 127:, and in 113:signaling 47:palmitoyl 8791:Vitamins 8786:Proteins 8751:Coloring 8502:Nonhuman 8487:O-linked 8482:N-linked 8274:Specific 8060:Ceramide 7914:Ceramide 7804:Inositol 7772:backbone 7704:PI(4,5)P 7696:PI(3,5)P 7688:PI(3,4)P 7593:backbone 7591:Glycerol 7098:Gadoleic 7079:Sapienic 7048:Nervonic 6983:Vaccenic 6916:Calendic 6894:Linoleic 6690:Decenoic 6684:Octenoic 6605:Melissic 6593:Montanic 6527:Margaric 6521:Palmitic 6509:Myristic 6473:Caprylic 6467:Enanthic 6358:Steroids 6348:Ceramide 6290:Triolein 6114:Geometry 5784:16391215 5741:16467233 5705:18753397 5662:15968579 5628:34030743 5620:18307699 5600:Obes Rev 5585:24998042 5577:18377789 5542:18427401 5515:18996687 5466:20742062 5458:19326716 5423:19328262 5388:19022225 5242:15012203 5207:16621811 5158:46348092 5150:15012259 5115:15952903 5072:15726818 4955:19237595 4906:21937549 4898:15811335 4841:11269317 4728:23782770 4720:24305041 4677:19035881 4636:18691060 4601:17981624 4560:18751921 4509:18951299 4474:17327576 4439:21505029 4390:15134755 4347:31357937 4339:18256869 4304:21743455 4255:17878492 4212:15 March 4199:10959497 4191:11296516 4141:15867152 4038:17051225 3989:18216768 3897:33793221 3873:in vitro 3830:34212942 3773:18387369 3724:18473889 3675:44858908 3667:15031493 3617:16479018 3563:16019076 3493:17349800 3458:12735695 3418:17161336 3323:12543708 3288:12648773 3247:18508430 3069:17954212 3028:10878232 2993:26822092 2908:15467400 2873:17599463 2805:14654091 2770:18751909 2688:17263298 2507:. 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