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Lipids
Lipids
DE S TA S E YO UM (C.PH AR M A CIS T )
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Lipids are broadly defined as any fat-soluble (lipophilic),
naturally-occurring molecule, such as fats, oils, waxes,
cholesterol, 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, acting as structural components of cell
membranes, and participating as important signaling
molecules.
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
and phospholipids), as well as other sterol-containing
metabolites such as cholesterol.
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Classification of lipids
On the basis of the nature of the products obtained on
hydrolysis, Lipids are mainly divided in two types
such as simple Lipids and Compound Lipids.
Besides thus there is one more type called derived
lipids .
Simple lipids :- Lipids which upon Hydrolysis yield
one or more fatty acids and an alcohol.
Compound Lipids :- Lipids which upon Hydrolysis
yield in addition to fatty acids and alcohol , compound
such as phosphoric acid , sugar ,etc
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Derived Lipids:- Lipids which also do not contain any
ester linkage but may be considered to have been derived
from naturally occurring esterified materials .
Most of this has been alcohols of complex nature. eg.
Certain steroids, Certain Vitamins ,and certain plant
pigments .
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Lipids may be broadly defined as hydrophobic or
amphiphilic small molecules that originate
entirely or in part from two distinct types of
biochemical subunits or "building blocks":
ketoacyl and isoprene groups.
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)
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Categories of Lipids
7
1 Fatty acyls
2 Glycerolipids
3 Glycerophospholipids
4 Sphingolipids
5 Saccharolipids
6 Polyketides
7 Sterol lipids
8 Prenol lipids
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8
1. Fatty acyls
Fatty acyls (including fatty acids) are a diverse group of
molecules synthesized by chain-elongation of an acetyl-
CoA primer with malonyl-CoA or methylmalonyl-CoA
groups.
The fatty acyl structure represents the major lipid
building block of complex lipids and therefore is one of
the most fundamental categories of biological lipids.
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Triglycerides
14
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2. Glycerolipids
Glycerolipids are composed mainly of mono-, di- and
tri-substituted glycerols , the most well-known being
the fatty acid esters of glycerol (triacylglycerols), also
known as triglycerides.
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Glycerolipids are complex lipids formed by the
condensation of one, two, or three fatty acid molecules on
glycerol, a small compound with three carbon atoms (either
numerically numbered C1, C2, C3, or, according to the Greek
alphabet, Cα, Cβ, Cα’), with each one bearing a hydroxyl
function OH. Glycerol is a symmetrical molecule and its two
terminal –CH2OH groups (referred to as α and α’) are
stereochemically equivalent. The central carbon C2, which is
not asymmetric, is referred to as β.
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Glycerolipids Synthesis
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Each OH function of glycerol can react with the –COOH group
of a fatty acid, leading to an ester derivative called glyceride.
An ester results from the condensation of a carboxylic acid and
an alcohol.
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Each carbon atom of glycerol can be linked to a fatty acid,
which will then become a chemical group by itself referred to
as “acyl.” If all three carbons of glycerol have reacted with a
fatty acid, we will obtain a triacylglycerol (TAG), also named
triglyceride. Diacylglycerol (DAG, diglycerides) include either
αα’ or αβ derivatives, according to the site of esterification.5
Similarly, the two categories of monoacylglycerol (MAG,
monoglycerides) are α and β. Examples of MAG, DAG, and
TAG (mono-, di-, or triacylglycerol) structures are given in
Fig. 1.12.
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Most membrane glycerolipids are phospholipids. These
membrane components are obtained by the condensation of
an αβ-DAG with phosphoric acid, leading to a molecule called
phosphatidic acid (PA). PA is the precursor of membrane
glycerophospholipids. The most important biochemical
feature of this class of compounds is the nature of the acyl
chain in α and β of glycerol; R1 (in position α) results from the
condensation of a saturated fatty acid, whereas R2 (in position
β) comes from an unsaturated fatty acid. This unique
combination of saturated/unsaturated chains is critical for
proper membrane function
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PA6 is a metabolic intermediate in the
biosynthetic/degradation pathways of more complex
glycerophospholipids. It usually represents less than 1% of
total membrane lipids but plays a critical role in signal
transduction, due to the unique ionization properties of its
phosphate group (see Chapter 3). Membrane
glycerophospholipids are derived from PA by condensation
with an organic alcohol (general formula X-OH).
Phosphatidylcholine (PC), the most abundant membrane
lipid, results from the condensation of choline with PA
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Cardiolipin(Diphosphotidylglycerol
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3. 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 signaling.
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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 signaling.
Glycerophospholipids may be subdivided into distinct classes,
based on the nature of the polar head group at the sn-3 position of
the glycerol backbone in eukaryotes and eubacteria or the sn-1
position in the case of archaebacteria.
Examples of glycerophospholipids found in biological membranes
are phosphatidylcholine (also known as PC or GPCho, and
lecithin),phosphatidylethanolamine (PE or GPEtn) and
phosphatidylserine (PS or GPSer).
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Phospholipids are the second most abundant
group of naturally occurring lipids
they are found almost exclusively in plant and
animal membranes, which typically consist of 40% -
50% phospholipids and 50% - 60% proteins
the most abundant phospholipids are derived from
phosphatidic acid, a molecule in which glycerol is
esterified with two molecules of fatty acid and one
of phosphoric acid
the three most abundant fatty acids in phosphatidic
acids are palmitic acid (16:0), stearic acid (18:0),
and oleic acid (18:1)
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Phospholipids
O
stearic acid CH2 -O-P-O -
O
-
CH O
O
O CH2
palmitic acid O glycerol
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Phospholipids
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Phospholipids
choline
O
+
O P OCH 2 CH2 N(CH 3 ) 3
stearic acid O-
O CH2
O CH
O CH2 glycerol
O
palmitic acid
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In the Western diet, palmitic acid (C16:0) and stearic acid (C18:0)
are the most commonly consumed saturated fatty acids [2]. It is
generally believed that palmitic acid is more cholesterol-raising
than stearic acid.
The key difference between palmitic acid and stearic acid is that
palmitic acid is more cholesterol-raising than stearic acid.
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Phosphotidylethanolamine
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Phosphatidylcholine (PC)
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• Structural Role:
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• Role in transport of lipids from intestines:
• Membrane phospholipids:
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• Insulation:
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Role in PGs and leukotrienes
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Selective inhibition by Aspirin
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• PGI2- Endothelium
• TXA2-Platelets
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Role as second messenger
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Lung surfactant
• Premature baby can suffer from ARDS(Acute Respiratory
Distress Syndrome)
• Following are Lung surfactant
– Dipalmitoyl-lecithin
– Sphingomyelin
• L to S ratio for lung maturity
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Phospholipases are enzymes that hydrolyze specific portions of
phospholipid molecules. Their role in the digestion of exogenous
phospholipids and as the active principle in snake and bee venoms
has long been appreciated.
Classification of Phospholipases
Phospholipases are further classified into different types which are
presented in Tables 2 and 3 (mammalian PLA1/PLA2 and
PLC/PLD, respectively) and Table 4 (plant phospholipases). This
classification is based on their distribution, sequence similarity,
structure characteristics and requirements for optimum activity
in vitro, which is connected to the differential activation of these
enzymes.
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Phospholipases are enzymes that degrade cell membranes to allow
pathogens to escape phagosomes.
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Role of Phospholipase
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Snake bite cause severe haemolysis
The venom contains lecithinase,
hydrolyzes the PUFA converting lecithin into lysolecithin (detergent
like action).
Lysolecithin causes hemolysis of RBCs.
cause anaphylactic shock as well as bleeding tency.
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4. Sphingolipids
Sphingolipids are a complex family of compounds that
share a common structural feature, a sphingoid base
backbone that is synthesized de novo from serine and a
long-chain fatty acyl CoA, then converted into
ceramides, phosphosphingolipids, glycosphingolipids
and other species.
The major sphingoid base of mammals is commonly
referred to as sphingosine.
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Sphingolipids are a type of lipids made up of fatty acid chains
that were first mentioned in 1884 in J.L.W. Thudichum’s A Treatise
on the chemical composition of the brain.
They were named after the Greek mythological creature, the
sphinx, due to the unknown riddle of their function.
Sphingolipids are found in essentially all plants, animals, fungi
and in some prokaryotes and viruses. Specifically, they are found in
membranes and as a major component of lipoproteins.
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Structure
Sphingolipids are amphipathic molecules; they have hydrophobic
and hydrophilic properties.
In the hydrophobic region there is a sphingoid long chain base
(aliphatic chains with attached hydroxyl groups) with a fatty acid
chain attached by amide bond at carbon 2.
In the hydrophilic region, there are phosphate groups, sugar
residues, and/or hydroxyl groups. This amphipathic nature allows for
the diffusion of sphingolipids between membranes and for the
flipping of sphingolipids between membrane leaflets.
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However, sphingolipids are still more likely to accumulate in acidic
environments because of the possible ionization of a free amino
group.[4] There are several classes of sphingolipids: the sphingoid
base and simple derivatives, ceramides, and complex sphingolipids
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Sphingoid base & simple derivatives
Sphingolipids are composed of many backbone “sphingoid
bases” which are synthesized from serine and a long-chain fatty
acyl-CoA. If a backbone has not yet been analyzed, it is referred to
as a sphinosine, after the original name for the fundamental
component of these lipids.
Sphingoid bases can vary in alkyl chain length/branching, the
number and position of double bonds, the number and locations of
hydroxyl groups, etc.
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These simple derivatives exist mainly as the backbone of more
complex sphingolipids, but they do exist on their own. They are
mainly used in intra-and extra-cellular signaling.
The exact structure of the sphingolipid determines the function.
For example, in the dermis, there are additional hydroxyl groups at
positions 4 and/or 6 that interact with neighboring molecules to
strengthen the permeability of the skin barrier.
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Ceramides
Ceramides, which are synthesized in the endoplasmic reticulum,
are the simplest sphingolipid after the backbone.
They are fatty acid derivatives of sphingoid bases, linked by amide
bonds. They are usually fully saturated or mono-unsaturated and
consist of 14-26 carbons, but are sometimes longer. There is
sometimes a hydroxyl group on the ω or ω-carbon atom.
Ceramides have high phase transition temperatures of greater than
37°C. This is due to their predominately saturated nature, which
allows for the tight packing of lipids. This also favors the segregation
of ceramides (and more complex sphingolipids) into regions called
membrane
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Ceramides are key to cell signaling processes. They generally
serve as second messengers by regulating cell growth, senescence,
and apoptosis.
The exact function depends on the type of sphingolipid base and
fatty acid. For example, ceramides containing palmitic acid for a fatty
acid chain are generated in response to apoptosis.
Much of the specifics of ceramide function is still under
investigation. Ceramides also serve as a precursor to more complex
sphingolipids.
Ceramides can only exist in membranes but they have a rapid flip
rate between leaflets. This means they cannot leave the organelle they
are created in, but will have access to binding proteins and enzymes
on both sides of the bilayer. As such, ceramides can usually only be
modified by enzymes that exist in the membrane compartment that
the ceramide was produced in
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Complex Sphingolipids
The synthesis of complex sphingolipids occurs in the Golgi
apparatus.
The bulky head groups of these sphingolipids make flipping
between membrane leaflets very unlikely without the aid of flip
passes. This means that without flip passes, sphingolipids are
restricted to the luminal Golgi leaflet/outer leaflet of the plasma
membrane.
The two main type of complex sphingolipids are phospho- and
glycol-sphingolipids.
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Phosphosphingolipids
Phosphosphingolipids are linked by phosphodiester bonds.[5] In
mammals, the major phosphosphingolipids are gomyelins
(ceramide phosphocholines).
In insects, it is ceramide phosphoethanolamines. The major
phosphosphingolipids in fungi are phyto ceramides
phosphoinositols and inositol phosphates.
Aquatic organisms typically have sphingolipids where the
phosphate has been replaced with a phosphono- or arsenate group.
.
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Glycosphingolipids
Glycosphingolipids have one or more carbohydrate groups in a
glycosidic linkage (usually; ceramide phophonositols are an
exception).
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Cellular Signaling
Sphingolipids affect cell signaling by influencing the properties of
receptors directly. The exact pathway for signal transduction varies
depending on the exact function of the sphingolipids but there is a
general pathway.
Receptors are activated by cytokines (i.e. IL1, tumor necrosis
factor-ω), growth factors (i.e. platelet derived growth factor), or
other agonists.
Hydrolysis of membrane sphingolipid to ceramide is induced.
Sphingolipids either serve as a lipid second messenger, or can be
converted to downstream metabolites (i.e. sphingosine, sphingosine
1-phosphate, ceramide 1-phosphate).
Downstream targets (i.e. proteins kinases, phosphoprotein
phosphatases) that control cell behavior are either activated or
inhibited.
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Sometimes, multiple sphingolipids within the same cell have
opposing signaling function. For example, ceraminde and
sphingosine 1-phosphate signal for conflicting functions of cell
growth. One signals for the inhibition of growth, while the other
signals for the stimulation of growth. (Or in other words, the
induction vs. inhibition of apoptosis.)
The cellular pathway taken is determined by a
ceraminde/sphingosine 1-phosophate “rheostat” in deciding between
growth arrest/apoptosis and proliferation/survial.
Because sphingolipids are complex molecules, they can take diverse
input signals and produce multiple coordinated outputs. Signaling
from sphingolipids also alters membrane structure and behavior of
other membrane receptors and/or proteins.
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5. Saccharolipids
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 the
lipopolysaccharides in Gram-negative bacteria.
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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 Escherichia coli is Kdo2-
Lipid A, a hexa-acylated disaccharide of glucosamine (LipidA) that
is glycosylated with two 3-deoxy-D-manno-octulosonic acid (Kdo)
residues.
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Chemical structure of lipid A as found in E. Coli
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6. Polyketides
Polyketides are synthesized by polymerization of acetyl and
propionyl subunits by classic enzymes as well as interative and
multimodular enzymes that share mechanistic features with the
fatty acid synthesis.
They comprise a very large number of secondary metabolites
and natural products from animal, plant, bacterial, fungal and
marine sources, and have great structural diversity.
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, tetracylines, avermectins, and antitumor
epothilones.
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7. Sterol lipids
Sterol lipids, such as cholesterol and its derivatives are an
important component of membrane lipids,along with the
glycerophospholipids and sphingomyelins.
The steroids, which also contain the same fused four-ring core
structure, have different biological roles as hormones and
signaling molecules.
The 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. The secosteroids,
comprising various forms of vitamin D, are characterized by
cleavage of the B ring of the core structure.
Other examples of sterols are the bile acids and their
conjugates,which in mammals are oxidized derivatives of
cholesterol and are synthesized in the liver.
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Sterol is an organic compound with formula C17H28O, whose
molecule is derived from that of gonane by replacement of a
hydrogen atom in position 3 by a hydroxyl group. It is therefore an
alcohol of gonane. More generally, any compounds that contain the
gonane structure, additional functional groups, and/or modified ring
systems derived from gonane are called steroids. Therefore, sterols
are a subgroup of the steroids. They occur naturally in most
eukaryotes, including plants, animals, and fungi, and can also be
produced by some bacteria (however likely with different functions).
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8. 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.
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 anti-oxidants and as precursors of vitamin A.
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.
Vitamin E and vitamin K, as well as the ubiquinones, are
examples of this class.
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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.
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Prenol
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Isopentenyl diphosphate
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Signaling
In recent years, evidence has emerged showing that lipid signaling
is a vital part of the cell signaling.
Lipid signaling may occur via activation of GPCR's or nuclear
receptors, and members of several different lipid categories have
been identified as signaling molecules and cellular messengers.
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Signaling ……
These include sphingosine-1-phosphate, a sphingolipid
derived from ceramide that is a potent messenger molecule
involved in regulating calcium mobilization, cell growth,
apoptosis; diacylglycerol(DAG) and the
phosphatidylinositol phosphates (PIPs), involved in
calcium-mediated activation of protein kinase C; the
prostaglandins, which are one type of fatty-acid derived
eicosanoid involved in inflammation and immunity; 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 (LXR) agonists.
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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.
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
prokaryotes.
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Characterization of Physicochemical Properties
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Basically, the sample is placed into an NMR instrument and a radio
frequency pulse is applied to it.
This induces a NMR signal in the sample, whose decay rate
depends on whether the lipid is solid or liquid.
The signal from the solid fat decays much more rapidly than the
signal from the liquid oil and therefore it is possible to distinguish
between these two components.
Techniques based on differential scanning calorimetry are also
commonly used to monitor changes in SFC.
These techniques measure the heat evolved or absorbed by a lipid
when it crystallizes or melts.
By making these measurements over a range of temperatures it is
possible to determine the melting point, the total amount of lipid
involved in the transition and the SFC-temperature profile.
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Melting point
In many situations, it is not necessary to know the SFC over the
whole temperature range, instead, only information about the
temperature at which melting starts or ends is required.
A pure triacylglycerol has a single melting point that occurs at a
specific temperature.
Nevertheless, foods lipids contain a wide variety of different
triacylglycerols, each with their own unique melting point, and so
they melt over a wide range of temperatures.
Thus the "melting point" of a food lipid can be defined in a
number of different ways, each corresponding to a different amount
of solid fat remaining.
Some of the most commonly used "melting points" are:
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• Clear point. A small amount of fat is placed in a
capillary tube and heated at a controlled rate. The
temperature at which the fat completely melts and
becomes transparent is called the "clear point".
• Slip point. A small amount of fat is placed in a capillary
tube and heated at a controlled rate. The temperature at
which the fat just starts to move downwards due to its
weight is called the "slip point".
• Wiley melting point. A disc of fat is suspended in an
alcohol-water mixture of similar density and is then heated
at a controlled rate. The temperature at which the disc
changes shape to a sphere is called the "Wiley melting
point".
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Cloud point
This gives a measure of the temperature at which
crystallization begins in a liquid oil.
A fat sample is heated to a temperature where all the crystals
are known to have melted (e.g., 130oC).
The sample is then cooled at a controlled rate and the
temperature at which the liquid just goes cloudy is determined.
This temperature is known as the cloud point, and is the
temperature where crystals begin to form and scatter light.
It is often of practical importance to have an oil which does
not crystallize when stored at 0oC for prolonged periods.
A simple test to determine the ability of lipids to withstand
cold temperatures without forming crystals, is to ascertain
whether or not a sample goes cloudy when stored for 5 hours at
0oC.