Lipid

From Wikipedia, the free encyclopedia

  (Redirected from Fat (nutrition))

Structures of some common lipids. At the top are oleic acid[1] and cholesterol.[2] The middle structure is
a triglyceride composed of oleoyl, stearoyl, and palmitoyl chains attached to a glycerol backbone. At the bottom is the
common phospholipid, phosphatidylcholine.[3]

Lipids are a broad group of naturally occurring molecules which includes fats, waxes, sterols, fat-

soluble vitamins(such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The
main biological functions of lipids include energy storage, as structural components of cell membranes, and as
important signaling molecules.

Lipids may be broadly defined as hydrophobic or amphiphilic small molecules; the amphiphilic nature of some
lipids allows them to form structures such as vesicles, liposomes, or membranes in an aqueous environment.
Biological lipids originate entirely or in part from two distinct types of biochemical subunits or "building
blocks": ketoacyl andisoprene groups.[4] Using this approach, lipids may be divided into eight categories: fatty
acyls, glycerolipids,glycerophospholipids, sphingolipids, saccharolipids and polyketides (derived from
condensation of ketoacyl subunits); and sterol lipids and prenol lipids (derived from condensation of isoprene
subunits).

Although the term lipid is sometimes used as a synonym for fats, fats are a subgroup of lipids
called triglycerides. Lipids also encompass molecules such as fatty acids and their derivatives
(including tri-, di-, and monoglycerides andphospholipids), as well as other sterol-containing metabolites such
as cholesterol.[5] Although humans and other mammals use various biosynthetic pathways to both break down
and synthesize lipids, some essential lipids cannot be made this way and must be obtained from the diet.

Contents
  [hide]

1 Categories of lipids

o 1.1 Fatty acyls

o 1.2 Glycerolipi

ds

o 1.3 Glyceroph

ospholipids

o 1.4 Sphingolip

ids

o 1.5 Sterol

lipids

o 1.6 Prenol

lipids

o 1.7 Saccharoli

pids

o 1.8 Polyketides

2 Biological functions

o 2.1 Membrane

o 2.2 Energy

storage

o 2.3 Signaling

o 2.4 Other

functions

3 Metabolism

o 3.1 Biosynthes

is

o 3.2 Degradatio

4 Nutrition and health

5 See also

6 References

o 6.1 Bibliograp
 hy

7 External links

[edit]Categories of lipids
[edit]Fatty acyls
Fatty acids, a generic term for describing [[ india ]], their conjugates and derivatives, are a diverse group of
molecules synthesized by chain-elongation of an acetyl-CoA primer with malonyl-CoA ormethylmalonyl-
CoA groups in a process called fatty acid synthesis.[6][7] They are made of a hydrocarbon chain that terminates
with a carboxylic acid group; this arrangement confers the molecule with a polar, hydrophilic end, and a
nonpolar, hydrophobic end that is insoluble 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 to 24 carbons long,[8] may be saturated or unsaturated, and may be
attached to functional groups containingoxygen, halogens, nitrogen and sulfur. Where a double bond exists,
there is the possibility of either a cis or trans geometric isomerism, which significantly affects the
molecule's molecular configuration. Cis-double bonds cause the fatty acid chain to bend, an effect that is more
pronounced the more double bonds there are in a chain. This in turn plays an important role in the structure
and function of cell membranes.[9] Most naturally occurring fatty acids are of the cis configuration, although
the trans form does exist in some natural and partially hydrogenated fats and oils. [10]

Examples of biologically important fatty acids are the eicosanoids, derived primarily from arachidonic
acid and eicosapentaenoic acid, which include prostaglandins, leukotrienes, and thromboxanes. Other major
lipid classes in the fatty acid category are the fatty esters and fatty amides. Fatty esters include important
biochemical intermediates such as wax esters, fatty acid thioester coenzyme Aderivatives, fatty acid
thioester ACP derivatives and fatty acid carnitines. The fatty amides include N-acyl ethanolamines, such as
the cannabinoid neurotransmitter anandamide.[11]

[edit]Glycerolipids

Glycerolipids are composed mainly of mono-, di- and tri-substituted glycerols,[12] the most well-known being the
fatty acid esters of glycerol (triacylglycerols), also known as triglycerides. In these compounds, the three
hydroxyl groups of glycerol are each esterified, usually by different fatty acids. Because they function as a food
store, these lipids comprise the bulk of storage fat in animal tissues. The hydrolysis of the ester bonds of
triacylglycerols and the release of glycerol and fatty acids from adipose tissue is called fat mobilization.[13]

Additional subclasses of glycerolipids are represented by glycosylglycerols, which are characterized by the
presence of one or more sugar residues attached to glycerol via a glycosidic linkage. Examples of structures in
this category are the digalactosyldiacylglycerols found in plant membranes [14] and seminolipid from
mammalian sperm cells.[15]
[edit]Glycerophospholipids

Glycerophospholipids, also referred to as phospholipids, are ubiquitous in nature and are key components of
the lipid bilayer of cells, as well as being involved in metabolism and cell signaling. Neural tissue (including the
brain) contains relatively high amounts of glycerophospholipids, and alterations in their composition has been
implicated in various neurological disorders.[16] Glycerophospholipids may be subdivided into distinct classes,
based on the nature of the polar headgroup at the sn-3 position of the glycerol backbone in eukaryotes and
eubacteria, or the sn-1 position in the case ofarchaebacteria.[17]

Phosphatidylethanolamine[3]

Examples of glycerophospholipids found in biological membranes are phosphatidylcholine (also known as PC,

GPCho or lecithin), phosphatidylethanolamine(PE or GPEtn) and phosphatidylserine (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 phosphatidylinositols and phosphatidic acids are either
precursors of, or are themselves, membrane-derived second messengers.[18] 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
(plasmalogen) glycerophospholipids, as well as dialkylether variants in archaebacteria. [19]

[edit]Sphingolipids

Sphingolipids are a complex family of compounds[20] that share a common structural feature, a sphingoid

base backbone that is synthesized de novo from the amino acid serine and a long-chain fatty acyl CoA, then
converted into ceramides, phosphosphingolipids, glycosphingolipids and other compounds. The major
sphingoid base of mammals is commonly referred to as sphingosine. Ceramides (N-acyl-sphingoid bases) are
a major subclass of sphingoid base derivatives with an amide-linked fatty acid. The fatty acids are typically
saturated or mono-unsaturated with chain lengths from 16 to 26 carbon atoms. [21]

Sphingomyelin[3]

The major phosphosphingolipids of mammals are sphingomyelins (ceramide phosphocholines),[22] whereas

insects contain mainly ceramide phosphoethanolamines [23] and fungi have phytoceramide phosphoinositols
and mannose-containing headgroups.[24] The glycosphingolipids are a diverse family of molecules composed of
one or more sugar residues linked via a glycosidic bond to the sphingoid base. Examples of these are the
simple and complex glycosphingolipids such as cerebrosides and gangliosides.Atanu

[edit]Sterol lipids
Sterol lipids, such as cholesterol and its derivatives, are an important component of membrane lipids,[25] along
with the glycerophospholipids and sphingomyelins. The steroids, all derived from the same fused four-ring core
structure, have different biological roles as hormones and signaling molecules. The eighteen-carbon (C18)
steroids include the estrogen family whereas the C19 steroids comprise the androgens such
as testosterone and androsterone. The C21 subclass includes the progestogens as well as
the glucocorticoids and mineralocorticoids.[26] The secosteroids, comprising various forms of vitamin D, are
characterized by cleavage of the B ring of the core structure. [27] Other examples of sterols are the bile acids and
their conjugates,[28] which in mammals are oxidized derivatives of cholesterol and are synthesized in the liver.
The plant equivalents are the phytosterols, such as β-sitosterol, stigmasterol, and brassicasterol; the latter
compound is also used as abiomarker for algal growth.[29] The predominant sterol in fungal cell membranes
is ergosterol.[30]

[edit]Prenol lipids
Prenol lipids are synthesized from the 5-carbon precursors isopentenyl diphosphate and dimethylallyl
diphosphate that are produced mainly via the mevalonic acid (MVA) pathway.[31] The simple isoprenoids (linear
alcohols, diphosphates, etc.) are formed by the successive addition of C5 units, and are classified according to
number of these terpene units. Structures containing greater than 40 carbons are known as
polyterpenes. Carotenoids are important simple isoprenoids that function as antioxidants and as precursors
of vitamin A.[32] Another biologically important class of molecules is exemplified by
the quinones and hydroquinones, which contain an isoprenoid tail attached to a quinonoid core of non-
isoprenoid origin.[33] Vitamin E and vitamin K, as well as the ubiquinones, are examples of this class.
Prokaryotes synthesize polyprenols (called bactoprenols) in which the terminal isoprenoid unit attached to
oxygen remains unsaturated, whereas in animal polyprenols (dolichols) the terminal isoprenoid is reduced.[34]

[edit]Saccharolipids
Structure of the saccharolipid Kdo2-Lipid A.[35]Glucosamine residues in blue, Kdo residues in red, acylchains in black
and phosphate groups in green.

Saccharolipids describe compounds in which fatty acids are linked directly to a sugar backbone, forming
structures that are compatible with membrane bilayers. In the saccharolipids, a monosaccharide substitutes for
the glycerol backbone present in glycerolipids and glycerophospholipids. The most familiar saccharolipids are
the acylated glucosamine precursors of the Lipid A component of thelipopolysaccharides in Gram-negative
bacteria. Typical lipid A molecules are disaccharides of glucosamine, which are derivatized with as many as
seven fatty-acyl chains. The minimal lipopolysaccharide required for growth in E. coli is Kdo2-Lipid A, a hexa-
acylated disaccharide of glucosamine that is glycosylated with two 3-deoxy-D-manno-octulosonic acid (Kdo)
residues.[35]

[edit]Polyketides

Polyketides are synthesized by polymerization of acetyl and propionyl subunits by classic enzymes as well as

iterative and multimodular enzymes that share mechanistic features with the fatty acid synthases. They
comprise a large number of secondary metabolites and natural products from animal, plant, bacterial, fungal
and marine sources, and have great structural diversity. [36][37] Many polyketides are cyclic molecules whose
backbones are often further modified by glycosylation, methylation, hydroxylation, oxidation, and/or other
processes. Many commonly used anti-microbial, anti-parasitic, and anti-cancer agents are polyketides or
polyketide derivatives, such as erythromycins,tetracyclines, avermectins, and antitumor epothilones.[38]

[edit]Biological functions
[edit]Membranes

Eukaryotic cells are compartmentalized into membrane-bound organelles which carry out different biological
functions. The glycerophospholipids are the main structural component of biological membranes, such as the
cellular plasma membrane and the intracellular membranes of organelles; in animal cells the plasma
membrane physically separates the intracellular components from theextracellular environment. The
glycerophospholipids are amphipathic 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 phosphate ester linkage. While glycerophospholipids are the major component of biological membranes,
other non-glyceride lipid components such assphingomyelin and sterols (mainly cholesterol in animal cell
membranes) are also found in biological membranes.[39] In plants and algae, the galactosyldiacylglycerols,
[40]
 and sulfoquinovosyldiacylglycerol,[14] which lack a phosphate group, are important components of
membranes of chloroplasts and related organelles and are the most abundant lipids in photosynthetic tissues,
including those of higher plants, algae and certain bacteria.

Bilayers have been found to exhibit high levels of birefringence which can be used to probe the degree of order
(or disruption) within the bilayer using techniques such as dual polarisation interferometry

Self-organization of phospholipids: a sphericalliposome, a micelle and a lipid bilayer.

A biological membrane is a form of lipid bilayer. The formation of lipid bilayers is an energetically preferred
process when the glycerophospholipidsdescribed above are in an aqueous environment. [41] 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 vesicle; depending on
the concentration of the lipid, this biophysical interaction may result in the formation of micelles, liposomes,
or lipid bilayers. Other aggregations are also observed and form part of the polymorphism of amphiphile (lipid)
behavior. Phase behavior is an area of study within biophysics and is the subject of current academic research.
[42][43]
Micelles and bilayers form in the polar medium by a process known as the hydrophobic effect.[44] 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 hydrogen bonds to the lipophilic areas of the amphiphile. So in an aqueous environment, the water
molecules form an ordered "clathrate" cage around the dissolved lipophilic molecule.[45]

[edit]Energy storage
Triacylglycerols, stored in adipose tissue, are a major form of energy storage in animals. The adipocyte, or fat
cell, is designed for continuous synthesis and breakdown of triacylglycerols, with breakdown controlled mainly
by the activation of hormone-sensitive enzyme lipase.[46] The complete oxidation of fatty acids provides high
caloric content, about 9 kcal/g, compared with 4 kcal/g for the breakdown of carbohydrates and proteins.
Migratory birds that must fly long distances without eating use stored energy of triacylglycerols to fuel their
flights.[47]

[edit]Signaling

In recent years, evidence has emerged showing that lipid signaling is a vital part of the cell signaling.[48] Lipid
signaling may occur via activation of G protein-coupled or nuclear receptors, and members of several different
lipid categories have been identified as signaling molecules and cellular messengers.[49] These
include sphingosine-1-phosphate, a sphingolipid derived from ceramide that is a potent messenger molecule
involved in regulating calcium mobilization,[50] cell growth, and apoptosis;[51] diacylglycerol (DAG) and
the phosphatidylinositol phosphates (PIPs), involved in calcium-mediated activation of protein kinase C;
[52]
 theprostaglandins, which are one type of fatty-acid derived eicosanoid involved
in inflammation and immunity;[53] the steroid hormones such as estrogen, testosterone and cortisol, which
modulate a host of functions such as reproduction, metabolism and blood pressure; and the oxysterols such as
25-hydroxy-cholesterol that are liver X receptor agonists.[54]

[edit]Other functions
The "fat-soluble" vitamins (A, D, E and K) – which are isoprene-based lipids – are essential nutrients stored in
the liver and fatty tissues, with a diverse range of functions. Acyl-carnitines are involved in the transport and
metabolism of fatty acids in and out of mitochondria, where they undergo beta oxidation.[55] Polyprenols and
their phosphorylated derivatives also play important transport roles, in this case the transport
of oligosaccharides across membranes. Polyprenol phosphate sugars and polyprenol diphosphate sugars
function in extra-cytoplasmic glycosylation reactions, in extracellular polysaccharide biosynthesis (for
instance, peptidoglycan polymerization in bacteria), and in eukaryotic protein N-glycosylation.[56]
[57]
 Cardiolipins are a subclass of glycerophospholipids containing four acyl chains and three glycerol groups
that are particularly abundant in the inner mitochondrial membrane. [58] They are believed to activate enzymes
involved with oxidative phosphorylation.[59]
[edit]Metabolism

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.

[edit]Biosynthesis

In animals, when there is an oversupply of dietary carbohydrate, the excess carbohydrate is converted to
triacylglycerol. This involves the synthesis of fatty acids from acetyl-CoA and the esterification of fatty acids in
the production of triacylglycerol, a process called lipogenesis.[60] Fatty acids are made by fatty acid
synthases 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, dehydrate it to an alkene group and then
reduce it again to an alkane 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,
[61]
 while in plant plastids and bacteria separate enzymes perform each step in the pathway. [62][63] The fatty acids
may be subsequently converted to triacylglycerols that are packaged in lipoproteins and secreted from the liver.

The synthesis of unsaturated fatty acids involves a desaturation reaction, whereby a double bond is introduced
into the fatty acyl chain. For example, in humans, the desaturation of stearic acid bystearoyl-CoA desaturase-
1 produces oleic acid. The doubly unsaturated fatty acid linoleic acid as well as the triply unsaturated α-
linolenic acid cannot be synthesized in mammalian tissues, and are therefore essential fatty acids and must be
obtained from the diet.[64]

Triacylglycerol synthesis takes place in the endoplasmic reticulum by metabolic pathways in which acyl groups
in fatty acyl-CoAs are transferred to the hydroxyl groups of glycerol-3-phosphate and diacylglycerol. [65]

Terpenes and isoprenoids, including the carotenoids, are made by the assembly and modification

of isoprene units donated from the reactive precursors isopentenyl pyrophosphate and dimethylallyl
pyrophosphate.[66] These precursors can be made in different ways. In animals and archaea, the mevalonate
pathway produces these compounds from acetyl-CoA,[67] while in plants and bacteria thenon-mevalonate
pathway uses pyruvate and glyceraldehyde 3-phosphate as substrates.[66][68] One important reaction that uses
these activated isoprene donors is steroid biosynthesis. Here, the isoprene units are joined together to
make squalene and then folded up and formed into a set of rings to make lanosterol.[69] Lanosterol can then be
converted into other steroids such as cholesteroland ergosterol.[69][70]

[edit]Degradation

Beta oxidation is the metabolic process by which fatty acids are broken down in the mitochondria and/or
in peroxisomes to generate acetyl-CoA. 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 dehydrogenation, hydration,
and oxidation to form a beta-keto acid, which is split by thiolysis. The acetyl-CoA is then ultimately converted
into ATP, CO2, and H2O using the citric acid cycle and theelectron transport chain.

Hence the Krebs 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. [71] Unsaturated and odd-chain
fatty acids require additional enzymatic steps for degradation.

[edit]Nutrition and health

Most of the lipid found in food is in the form of triacylglycerols, cholesterol and phospholipids. A minimum
amount of dietary fat is necessary to facilitate absorption of fat-soluble vitamins (A, D, E andK)
and carotenoids.[72] Humans and other mammals have a dietary requirement for certain essential fatty acids,
such as linoleic acid (an omega-6 fatty acid) and alpha-linolenic acid (an omega-3 fatty acid) because they
cannot be synthesized from simple precursors in the diet. [64] Both of these fatty acids are 18-
carbon polyunsaturated fatty acids differing in the number and position of the double bonds. Most vegetable
oils are rich in linoleic acid (safflower, sunflower, and corn oils). Alpha-linolenic acid is found in the green
leaves of plants, and in selected seeds, nuts and legumes (particularlyflax, rapeseed, walnut and soy).[73] Fish
oils are particularly rich in the longer-chain omega-3 fatty acids eicosapentaenoic acid (EPA)
and docosahexaenoic acid (DHA).[74] A large number of 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. [75][76] In contrast, it is
now well-established that consumption of trans fats, such as those present in partially hydrogenated vegetable
oils, are a risk factor for cardiovascular disease.[77][78][79]

A few studies have suggested that total dietary fat intake is linked to an increased risk of obesity [80][81] and
diabetes.[82][83] However, a number of very large studies, 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, revealed no such links.[84][85][86] 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 theHarvard School of Public Health, summarizes the current
evidence on the impact 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." [87]

Fat
From Wikipedia, the free encyclopedia
This article is about the type of nutrient in food. For fat in humans and animals, see Adipose tissue. For other
uses, see Fat (disambiguation).

Types of fats in food

 Unsaturated fat
 Monounsaturate
d fat
 Polyunsaturated
fat
 Trans fat
 Cis fat
 Omega fatty
acids:
 ω−3
 ω−6
 ω−9
 Saturated fat
 Interesterified fat
See also

 Fatty acid
 Essential fatty acid

Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble
in water. Chemically, fats are generally triesters of glyceroland fatty acids. Fats may be
either solid or liquid at room temperature, depending on their structure and composition. Although the words
"oils", "fats", and "lipids" are all used to refer to fats, "oils" is usually used to refer to fats that are liquids at
normal room temperature, while "fats" is usually used to refer to fats that are solids at normal room
temperature. "Lipids" is used to refer to both liquid and solid fats, along with other related substances. The
word "oil" is used for any substance that does not mix with water and has a greasy feel, such as petroleum (or
crude oil) and heating oil, regardless of its chemical structure.[1]

Fats form a category of lipid, distinguished from other lipids by their chemical structure and physical properties.
This category of molecules is important for many forms of life, serving both structural and metabolic functions.
They are an important part of the diet of most heterotrophs (including humans). Fats or lipids are broken down
in the body by enzymes called lipases produced in the pancreas.
Examples of edible animal fats are lard (pig fat), fish oil, and butter or ghee. They are obtained from fats in the
milk, meat and under the skin of the animal. Examples of edible plant fats are peanut, soya bean, sunflower,
sesame, coconut, olive, and vegetable oils. Margarine and vegetable shortening, which can be derived from the
above oils, are used mainly for baking. These examples of fats can be categorized into saturated
fats and unsaturated fats.

Contents
 [hide]

1 Chemical structure

o 1.1 Saturated and

unsaturated

o 1.2 Trans fatty acids

2 Importance for living

organisms

3 Adipose tissue

4 See also

5 References

Chemical structure

A triglyceride molecule

There are many different kinds of fats, but each is a variation on the same chemical structure. All fats consist
of fatty acids (chains of carbon andhydrogen atoms, with a carboxylic acid group at one end) bonded to a
backbone structure, often glycerol (a "backbone" of carbon, hydrogen, and oxygen). Chemically, this is
a triester of glycerol, an ester being the molecule formed from the reaction of the carboxylic acid and an organic
alcohol. As a simple visual illustration, if the kinks and angles of these chains were straightened out, the
molecule would have the shape of a capital letter E. The fatty acids would each be a horizontal line; the
glycerol "backbone" would be the vertical line that joins the horizontal lines. Fats therefore have "ester"bonds.

The properties of any specific fat molecule depend on the particular fatty acids that constitute it. Different fatty
acids are composed of different numbers of carbon and hydrogen atoms. The carbon atoms, each bonded to
two neighboring carbon atoms, form a zigzagging chain; the more carbon atoms there are in any fatty acid, the
longer its chain will be. Fatty acids with long chains are more susceptible to intermolecular forces of attraction
(in this case, van der Waals forces), raising its melting point. Long chains also yield more energy per molecule
when metabolized.

Saturated and unsaturated

A fat's constituent fatty acids may also differ in the number of hydrogen atoms that are bonded to the chain of
carbon atoms. Each carbon atom is typically bonded to two hydrogen atoms. When a fatty acid has this typical
arrangement, it is called "saturated", because the carbon atoms are saturated with hydrogen; meaning they
are bonded to as many hydrogens as possible. In other fats, a carbon atom may instead bond to only one other
hydrogen atom, and have a double bond to a neighboring carbon atom. This results in an "unsaturated" fatty
acid. More specifically, it would be a monounsaturated fatty acid, whereas, a polyunsaturated fatty acid would
be a fatty acid with more than one double bond. Saturated and unsaturated fats differ in their energy content
and melting point. Since an unsaturated fat contains fewer carbon-hydrogen bonds than a saturated fat with the
same number of carbon atoms, unsaturated fats will yield slightly less energy during metabolism than saturated
fats with the same number of carbon atoms. Saturated fats can stack themselves in a closely packed
arrangement, so they can freeze easily and are typically solid at room temperature. But the rigid double bond in
an unsaturated fat fundamentally changes the chemistry of the fat.

Trans fatty acids

There are two ways the double bond may be arranged: the isomer with both parts of the chain on the same
side of the double bond (the cis-isomer), or the isomer with the parts of the chain on opposite sides of the
double bond (the trans-isomer). Most trans-isomer fats (commonly called trans fats) are commercially produced
rather than naturally occurring. The cis-isomer introduces a kink into the molecule that prevents the fats from
stacking efficiently as in the case of fats with saturated chains. This decreases intermolecular forces between
the fat molecules, making it more difficult for unsaturated cis-fats to freeze; they are typically liquid at room
temperature. Trans fats may still stack like saturated fats, and are not as susceptible to metabolization as other
fats.

Trans fats may significantly increase the risk of coronary heart disease.[2]

Importance for living organisms

Vitamins A, D, E, and K are fat-soluble, meaning they can only be digested, absorbed, and transported in
conjunction with fats. Fats are also sources of essential fatty acids, an important dietary requirement.

Fats play a vital role in maintaining healthy skin and hair, insulating body organs against shock, maintaining
body temperature, and promoting healthy cell function.

Fats also serve as energy stores for the body, containing about 37.8 kilojoules (9 Calories) per gram of fat[3].
They are broken down in the body to release glycerol and free fatty acids. The glycerol can be converted
to glucose by the liver and thus used as a source of energy.

Fat also serves as a useful buffer towards a host of diseases. When a particular substance, whether chemical
or biotic—reaches unsafe levels in the bloodstream, the body can effectively dilute—or at least maintain
equilibrium of—the offending substances by storing it in new fat tissue. This helps to protect vital organs, until
such time as the offending substances can be metabolized and/or removed from the body by such means
as excretion, urination, accidental or intentional bloodletting, sebum excretion, and hair growth.

While it is nearly impossible to remove fat completely from the diet, it would be unhealthy to do so. Some fatty
acids are essential nutrients, meaning that they can't be produced in the body from other compounds and need
to be consumed in small amounts. All other fats required by the body are non-essential and can be produced in
the body from other compounds.

Adipose tissue

The obese mouse on the left has large stores of adipose tissue. For comparison, a mouse with a normal amount of adipose
tissue is shown on the right.

Main article:  Adipose tissue

In animals, adipose, or fatty tissue is the body's means of storing metabolic energy over extended periods of
time. Depending on current physiologicalconditions, adipocytes store fat derived from the diet and
liver metabolism or degrade stored fat to supply fatty acids and glycerol to the circulation. These metabolic
activities are regulated by several hormones (i.e., insulin, glucagon and epinephrine). The location of the tissue
determines its metabolic profile: "Visceral fat" is located within the abdominal wall (i.e., beneath the wall of
abdominal muscle) whereas "subcutaneous fat" is located beneath the skin (and includes fat that is located in
the abdominal area beneath the skin but above the abdominal muscle wall). Visceral fat was recently
discovered to be a significant producer of signaling chemicals (i.e., hormones), among which are several which
are involved in inflammatory tissue responses. One of these isresistin which has been linked to obesity, insulin
resistance, and Type 2 diabetes. This latter result is currently controversial, and there have been reputable
studies supporting all sides on the issue.

Unsaturated fat
From Wikipedia, the free encyclopedia

Types of fats in food

 Unsaturated fat
 Monounsaturate
d fat
 Polyunsaturated
fat
 Trans fat
 Cis fat
 Omega fatty
acids:
 ω−3
 ω−6
 ω−9
 Saturated fat
 Interesterified fat
See also

 Fatty acid
 Essential fatty acid

An unsaturated fat is a fat or fatty acid in which there is at least one double bond within the fatty acid chain. A
fat molecule is monounsaturated if it contains one double bond, and polyunsaturated if it contains more than
one double bond. Where double bonds are formed, hydrogen atoms are eliminated. Thus, a saturated fat has
no double bonds, has the maximum number of hydrogens bonded to the carbons, and therefore is "saturated"
with hydrogen atoms. In cellular metabolism, hydrogen-carbon bonds are broken down – or oxidized – to
produce energy, thus an unsaturated fat molecule contains somewhat less energy (i.e., fewer calories) than an
equivalent amount of saturated fat. The greater the degree of unsaturation in a fatty acid (i.e., the more double
bonds in the fatty acid) the more vulnerable it is to lipid peroxidation(rancidity). Antioxidants can protect
unsaturated fat from lipid peroxidation.

Contents
 [hide]

1 Chemistry and nutrition

2 Role of dietary fats in insulin resistance

3 Membrane composition as a metabolic

pacemaker

4 Component in different foods

5 References

6 See also

[edit]Chemistry and nutrition

Amounts of fat types in selected foods

Double bonds may be in either a cis or a trans isomer, depending on the geometry of the double bond. In
the cis conformation, hydrogen atoms are on the same side of the double bond, whereas, in
the trans conformation, they are on opposite sides (see also Trans fat). Saturated fats are popular with
manufacturers of processed foodsbecause they are less vulnerable to rancidity and are, in general, more solid
at room temperature than unsaturated fats. Unsaturated chains have a lower melting point, hence increasing
fluidity of the cell membranes.

Although both monounsaturated and polyunsaturated fats can replace saturated fat in the diet, trans
unsaturated fats should be avoided. Replacing saturated fats with unsaturated fats helps to lower levels of
total cholesterol and LDL cholesterol in the blood[citation needed]. Trans unsaturated fats are particularly risky
because the double bond stereochemistry allows the fat molecules to assume a linear conformation, which
leads to efficient packing (i.e., plaque formation). The geometry of the cis double bond introduces a bend in the
molecule, thereby precluding stable formations (see specific fatty acid links above for drawings that illustrate
this). Natural sources of fatty acids (see above) are rich in the cis isomer.

Although polyunsaturated fats are protective against cardiac arrhythmias, a study of post-menopauseal women

with a relatively low fat intake showed that polyunsaturated fat is positively associated with progression
of coronary atherosclerosis, whereas monounsaturated fat is not.[1] This probably is an indication of the greater
vulnerability of polyunsaturated fats to lipid peroxidation, against which vitamin E has been shown to be
protective.[2]

Examples of unsaturated fats are palmitoleic acid, oleic acid, myristoleic acid, linoleic acid, and arachidonic

acid. Foods containing unsaturated fats includeavocado, nuts, and vegetable oils such as canola and olive
oils. Meat products contain both saturated and unsaturated fats.

Although unsaturated fats are healthier than saturated fats, [3] the United States Food and Drug
Administration (FDA) recommendation stated that the amount of unsaturated fat consumed should not exceed
30% of one's daily caloric intake (or 67 grams given a 2000 Calorie diet). The new dietary guidelines have
eliminated this recommendation at the request of the meat and dairy industries. Most foods contain both
unsaturated and saturated fats. Marketers advertise only one or the other, depending on which one makes up
the majority. Thus, various unsaturated fat vegetable oils, such as olive oils, also contain saturated fat.

[edit]Role of dietary fats in insulin resistance

Insulin resistance correlates positively with monounsaturated fat (especially oleic acid) and negatively with
polyunsaturated fat (especially arachidonic acid) in the phospholipids of human skeletal muscle.[4]

[edit]Membrane composition as a metabolic pacemaker

Cell membranes of mammals have a higher composition of polyunsaturated fat (DHA, omega-3 fatty acid) and
a lower composition of monounsaturated fat than do reptiles. Higher polyunsaturated membrane content gives
greater membrane fluidity (and functionality), commensurate with the higher metabolic rate of the warm-
blooded species. In fish, however, increasingly cold environments lead to increasingly high cell membrane
content of both monounsaturated and polyunsaturated fatty acids, to maintain greater membrane fluidity (and
functionality) at the lower temperatures.[5]

Saturated fat
From Wikipedia, the free encyclopedia

Types of fats in food

 Unsaturated fat
  Monounsaturated
fat
 Polyunsaturated
fat
 Trans fat
 Cis fat
 Omega fatty
acids:
 ω−3
 ω−6
 ω−9
 Saturated fat
 Interesterified fat
See also

 Fatty acid
 Essential fatty acid

Saturated fat is fat that consists of triglycerides containing only saturated fatty acid radicals. There are many kinds of naturally

occurring saturated fatty acids, which differ by the number of carbon atoms, ranging from 3 carbons (propionic acid) to 36

(Hexatriacontanoic acid). Saturated fatty acids have no double bonds between thecarbon atoms of the fatty acid chain and are thus

fully saturated with hydrogen atoms.

Fat that occurs naturally in tissue contains varying proportions of saturated and unsaturated fat. Examples of foods containing a

high proportion of saturated fat includedairy products (especially cream and cheese but also butter and ghee); animal fats such

as suet, tallow, lard and fatty meat; coconut oil, cottonseed oil, palm kernel oil,chocolate, and some prepared foods.[1]

Serum saturated fatty acid is generally higher in smokers, alcohol drinkers and obese people. [2]

Contents
 [hide]

1 Fat profiles

2 Examples of saturated fatty acids

3 Stable deepfry and baking medium

4 Association with diseases

o 4.1 Cardiovascular diseases

o 4.2 Cancer
  4.2.1 Breast cancer

 4.2.2 Prostate

cancer

 4.2.3 Small intestine

cancer

5 Dietary recommendations

6 Confounding factors

7 Molecular description

8 See also

9 References

[edit]Fat profiles

While nutrition labels usually combine them, the saturated fatty acids appear in different proportions among food

groups. Lauric and myristic acid radicals are most commonly found in "tropical" oils (e.g. palm kernel, coconut) and dairy products.

The saturated fat in meat, eggs, chocolate, and nuts is primarily the triglycerides of palmitic and stearic acid.

Saturated fat profile of common foods; Esterified fatty acids as percentage of total fat [3]

Food Lauric acid Myristic acid Palmitic acid Stearic acid

Coconut oil 47% 18% 9% 3%
Butter 3% 11% 29% 13%
Ground beef 0% 4% 26% 15%
Dark chocolate 0% 0% 34% 43%
Salmon 0% 1% 29% 3%
Eggs 0% 0.3% 27% 10%
Cashews 2% 1% 10% 7%
Soybean oil 0% 0% 11% 4%

Fat composition in different foods (click at right to hide or show) [show]

[edit]Examples of saturated fatty acids

Main article: List of saturated fatty acids

Some common examples of fatty acids:

 Butyric acid with 4 carbon atoms (contained in butter)

 Lauric acid with 12 carbon atoms (contained in coconut oil, palm oil, and breast milk)

 Myristic acid with 14 carbon atoms (contained in cow's milk and dairy products)

 Palmitic acid with 16 carbon atoms (contained in palm oil and meat)

 Stearic acid with 18 carbon atoms (also contained in meat and cocoa butter)

[edit]Stable deepfry and baking medium

It has been suggested that this article or section be merged into Polyunsaturated
fat. (Discuss)

Deepfry oils and baking fats that are high in saturated fats, like palm oil, tallow or lard, can withstand extreme heat (of 180-200

degrees Celsius) and are resistant to oxidation. A 2001 parallel review of 20-year dietary fat studies in the United Kingdom, the

United States of America and Spain concluded that polyunsaturated oils like soya, canola, sunflower and corn degrade easily to

toxic compounds and trans fat when heated up. Prolonged consumption of trans fat-laden oxidized oils can lead to atherosclerosis,

inflammatory joint disease and development of birth defects. The scientists also questioned global health authorities’ wilful

recommendation of large amounts of polyunsaturated fats into the human diet without accompanying measures to ensure the

protection of these fatty acids against heat- and oxidative-degradation.[7]

[edit]Association with diseases

[edit]Cardiovascular diseases
In 2010, a meta-analysis of prospective cohort studies including 348,000 subjects found no statistically significant relationship

between cardiovascular disease and dietary saturated fat.[8][9] However, the authors noted that randomized controlled clinical trials in

which saturated fat was replaced with polyunsaturated fat observed a reduction in heart disease, and that the ratio between

polyunsaturated fat and saturated fat may be a key factor. [8] In 2009, a systematic review of prospective cohort studies or

randomized trials concluded that there was "insufficient evidence of association" between intake of saturated fatty acids and

coronary heart disease, and pointed to strong evidence for protective factors such as vegetables and a Mediterranean diet and

harmful factors such as trans fats and foods with a high glycemic index.[10]

An evaluation of data from Harvard Nurses' Health Study found that "diets lower in carbohydrate and higher in protein and fat are

not associated with increased risk of coronary heart disease in women. When vegetable sources of fat and protein are chosen,

these diets may moderately reduce the risk of coronary heart disease." [11]

Mayo Clinic highlighted oils that are high in saturated fats include coconut, palm oil and palm kernel oil. Those of lower amounts of

saturated fats, and higher levels of unsaturated (preferably monounsaturated) fats like olive oil, peanut oil, canola oil, avocados,

safflower, corn, sunflower, soy and cottonseed oils are generally healthier. [12] However, high intake of saturated dairy fat does not

appear to increase the risk of cardiovascular disease[13] and Pacific island populations who obtain 30-60% of their total caloric intake

from fully saturated coconut fat have almost non-existent rates of cardiovascular disease. [14]

[edit]Cancer

[edit]Breast cancer

Further information: Epidemiology and etiology of breast cancer#Specific dietary fatty acids

A study published in 2001 found higher levels of monounsaturated fatty acids (especially oleic acid) in the erythrocyte membranes of

postmenopausal women who developed breast cancer.[15] However, another study showed a direct relation between very high

consumption of omega-6 polyunsaturated fats and breast cancer in postmenopausal women. [16]

[edit]Prostate cancer

Further information: Prostate cancer#Oils and fatty acids

Some researchers have indicated that serum myristic acid[17][18] and palmitic acid[18] and dietary myristic[19] and palmitic[19] saturated

fatty acids and serum palmitic combined with alpha-tocopherolsupplementation[17] are associated with increased risk of prostate

cancer in a dose-dependent manner. These associations may, however, reflect differences in intake or metabolism of these fatty

acids between the precancer cases and controls, rather than being an actual cause.[18]

[edit]Small intestine cancer

A prospective study of data from the NIH-AARP Diet and Health Study positively correlated saturated fat intake with cancer of the

small intestine.[20]

[edit]Dietary recommendations

A 2004 statement released by the Centers for Disease Control (CDC) determined that "Americans need to continue working to

reduce saturated fat intake…"[21] Additionally, reviews by the American Heart Association led the Association to recommend

reducing saturated fat intake to less than 7% of total calories according to its 2006 recommendations. [22][23] This concurs with similar

conclusions made by the World Health Organization (WHO) and the US Department of Health and Human Services, both of which

determined that reduction in saturated fat consumption would positively affect health and reduce the prevalence of heart disease. [24]
[25][26]

The World Health Organization (WHO) has concluded that saturated fats negatively affect cholesterol profiles, predisposing

individuals to heart disease, and recommends avoiding saturated fats in order to reduce the risk of a cardiovascular disease. [27][28]

Dr German and Dr Dillard of University of California and Nestle Research Center in Switzerland, in their 2004 review, pointed out

that "no lower safe limit of specific saturated fatty acid intakes has been identified". No randomized clinical trials of low-fat diets or

low-saturated fat diets of sufficient duration have been carried out. The influence of varying saturated fatty acid intakes against a

background of different individual lifestyles and genetic backgrounds should be the focus in future studies. [29]

[edit]Confounding factors
The relevance of particular information in (or previously in) this article or section
is disputed.

The information may have been removed or included by an editor as a result.

Please see discussion on the talk page considering whether its inclusion is warranted.(March 2008)

See also: Lipid hypothesis

An association between serum levels of fatty acids and disease does not in itself establish causality. [30][31]
 The formation of exogenous (outside the body) advanced glycation endproducts (AGEs) and oxidation products

generated during cooking may be a confounding factor that some studies may not have controlled for. It has been suggested

that, "given the prominence of this type of food in the human diet, the deleterious effects of high-(saturated)fat foods may be in

part due to the high content in glycotoxins, above and beyond those due to oxidized fatty acid derivatives." The glycotoxins, as

he called them, are more commonly called AGEs.[32]

 Studies of dietary customs of certain ethnic groups may be confounded by other cultural customs. For example, Fulani of

northern Nigeria get around 25% of energy from saturated fat, yet their lipid profile is indicative of a low risk of cardiovascular

disease. However, this finding may be due to their high activity level and their low total energy intake. [33]

 Saturated fat intakes may be monitored more closely than were total fat intakes, therefore ignoring the possibility that

simply a larger fat intake may lead to a higher risk of coronary diseases. It also suggests that other parameters may be

overlooked, such as carbohydrates intakes.[34]

[edit]Molecular description

Two-dimensional representation of the saturated fatty acid myristic acid

A space-filling model of the saturated fatty acid myristic acid

Monounsaturated fat
From Wikipedia, the free encyclopedia

Please help improve this article by expanding it. Further information might be

found on the talk page. (January 2007)

Types of fats in food

 Unsaturated fat
 Monounsaturated
 fat
 Polyunsaturated
fat
 Trans fat
 Cis fat
 Omega fatty acids:
 ω−3
 ω−6
 ω−9
 Saturated fat
 Interesterified fat
See also

 Fatty acid
 Essential fatty acid

For discussion how dietary fats affect cardiovascular health, see Diet and heart disease.

In biochemistry and nutrition, monounsaturated fats or MUFA (MonoUnsaturated Fatty Acid) are fatty

acids that have a single double bond in the fatty acid chain and all of the remainder of
the carbon atoms in the chain are single-bonded. By contrast, polyunsaturated fatty acids have more than
one double bond.

Fatty acids are long-chained molecules having a methyl group at one end and a carboxylic acid group at

the other end. Fatty acid viscosity (thickness) and melting temperature increases with decreasing number
of double bonds. Therefore, monounsaturated fatty acids have a higher melting point than
polyunsaturated fatty acids (more double bonds) and a lower melting point than saturated fatty acids (no
double bonds). Monounsaturated fatty acids are liquids at room temperature and semisolid or solid when
refrigerated.

Contents
 [hide]

1 Molecular description: oleic

acid

2 Relation to health

3 Natural sources

4 See also
 5 References

6 External links

[edit]Molecular description: oleic acid

Common monounsaturated fatty acids are palmitoleic acid (16:1 n−7), cis-vaccenic acid (18:1 n−7)

and oleic acid (18:1 n−9). Palmitoleic acid has 16 carbon atoms with the first double bond occurring 7
carbon atoms away from the methyl group (and 9 carbons from the carboxyl end). It can be lengthened to
the 18-carbon cis-vaccenic acid. Oleic acid has 18 carbon atoms with the first double bond occurring 9
carbon atoms away from the carboxylic acid group. The illustrations below show a molecule of oleic acid
in Lewis formula and as a space-filling model.

 
[edit]Relation to health

Although polyunsaturated fats protect against cardiovascular disease by providing

more membrane fluidity than monounsaturated fats, they are more vulnerable to lipid
peroxidation (rancidity). On the other hand, some monounsaturated fatty acids (in the same way as
saturated fats) promote insulin resistance, whereas polyunsaturated fatty acids are protective against
insulin resistance.[1][2] In contrast to this, the large scale KANWU study found that neither dietary
monounsaturated or supplemented polyunsaturated fats (in the form of fish oil) affected insulin sensitivity
while increased consumption of saturated fat significantly decreased insulin sensitivity. [3]

Foods containing monounsaturated fats reduce low-density lipoprotein (LDL) cholesterol, while possibly

increasing high-density lipoprotein (HDL) cholesterol.[4] However, their true ability to raise HDL is still in
debate.

Levels of oleic and monounsaturated fatty acids in red blood cell membranes were positively associated
with breast cancer risk. The saturation index (SI) of the same membranes was inversely associated with
breast cancer risk. Monounsaturated fats and low SI in erythrocyte membranes are predictors of
postmenopausal breast cancer. Both of these variables depend on the activity of the enzyme 9-d delta 9
desaturase.[5]

In children, consumption of monounsaturated oils is associated with healthier serum lipid profiles. [6]

[edit]Natural sources
Monounsaturated fats are found along with saturated fat in natural foods such as red meat, whole milk
products, nuts and high fat fruits such as olives and avocados. Olive oil is about 75% monounsaturated
fat while tea seed oil is commonly over 80% monounsaturated fat and Canola oil is about 58%
monounsaturated fat. Tallow (beef fat) is about 50% monounsaturated fat and lard is about 40%
monounsaturated fat. Other sources include macadamia nut oil, grapeseed oil, groundnut oil (peanut
oil), sesame oil, corn oil, popcorn, whole grain wheat, cereal, oatmeal, safflower oil,sunflower oil, tea-oil
Camellia, and avocado oil.

Fat composition in different foods (click at right to hide or show) [show]

[edit]See also

 High density lipoprotein

 Saturated fat

 Unsaturated fat

 Polyunsaturated fat