Lipids - biyokimya.vetbiyokimya.vet/documents/biyokimya/Lipids.pdf · Lipids Lipid are found in...

LIPIDSSerkan SAYINER, DVM PhD. Assist. Prof.

Near East University, Faculty of Veterinary Medicine

Department of Biochemistry

[email protected]

http://www.biyokimya.vet/en


https://neu.edu.tr/academic/faculties/faculty-of-veterinary-medicine/


mailto:[email protected]

Lipids Lipid are found in nature together with carbohydrates

and proteins. It is a group of organic substances that

carry the greatest importance in quantitative terms.

They are generally water-insoluble and dissolved in

organic solvents such as ether and chloroform.

They can be used by the living beings.

The most important features are their energy source

and their presence in membranes.

They may be esters of fatty acids or esterified.





Lipids have a unique place among organic molecules.

The identities of lipids are based on their physical

properties, not on the presence of specific functional

groups they contain.• For this reason, they are very wide and different, or are found,

and each has various functions.

Lipids contain very high numbers of non-polar C─C

and C─H bonds.

Lipids





In addition, most lipid molecules have several polar

bonds. • These polar bonds were made with various functional groups.

As a result, lipids are;• Nonpolar or weak polar,

• Soluble in organic solvents such as C6H14 and CCl4,

• Biomolecules that are insoluble in polar solvents such as

water.

Lipids have common properties with hydrocarbons in

many ways.

Lipids





1. Lipids are cell membrane components.• The cell membrane surrounds the cell to protect it from

external influences and allows metabolic activity in the cell to

take place.

• Membranes are not a simple structure surrounding the cell, but

contain many important enzymes and transport systems in

their structure.

• Membranes contain many specific receptors on their outer

surface, helping hormones and other substances to effect.

General Function of Lipids





Carbohydrates

Hydrophobic

region

Hydrophilic

region

Choleserol Peripheral protein

Integral protein

Cytoplasm

Nucleus

Cell Membrane Cell





Polar

head

Mem

ran

phosp

holipid

Non-Polar

tail

Polar

head

Hydrophobic

region Libid bilayerİntracellular

enviroment

Extracellular

enviroment

Cell

Membrane

Simple

diffusion

Faciliated

transport

Active

transport

Integral

membrane

protein

Energy

input

needed





2. They are good source of energy (predominantly

triglycerides).• Fat molecules, a good energy store, give more energy than

carbohydrates of the same weight.

• 9 kcal/g of energy is gained with the oxidation of fatty acids.◦ Carbohydrates and proteins give 4 kcal/g of energy.


Adipose tissue





3. Lipids are the source of some important items in organism.

• Lipoproteins

• Bile acids

• Vitamins in fat (A, D, E, K)

• Steroid hormones

4. They are effective in protecting against infections.• Eicosanoids

◦ Prostaglandins, Thromboxans, Prostacyclins, Leukotrienes, Lipoxins, Resolvins, Eoxins






5. They are involved in cellular signaling.• There are lipid messengers.

• They bind to protein structured target receptor or enzyme

(such as kinase, phosphatase) and allows the formation of a

specific response in the cell.

• These messengers are;◦ Sfingolipid secunder messengers (Seramid, sphingosine ...),

◦ Phosphatidylinositol secunder Messenger,

◦ G-protein coupled receptor activators (Prostaglandins,

lysophosphatidic acid ...),

◦ Nuclear receptor activators (Steroid hormones ...).






2. NON-HYDROLYZABLE LIPIDS• They are lipids that can not be

broken down into smaller

molecules when hydrolyzed with

water. The structure of such lipids

is more varied.

1. Steroids

2. Fat-soluble vitamins

3. Eicosanoids

1. HYDROLYZABLE LIPIDS• They are lipids that can be

separated into smaller

molecules when hydrolyzed

with water.

1. Triglycerides

2. Phospholipids

3. Waxes

4. Sphingolipids

Classification of Lipids





MEMBRANE LIPIDS (POLAR)

• Phospholipids◦ Glycerophospholipids

– Glycerol + 2 fatty acids + P +

Alcohol

◦ Sphingophospholipids

– Sphingosine + fatty acid + P +

Choline

• Glycolipids◦ Sphingoglycolipids

– Sphingosine + fatty acid + mono or

oligosaccharide

STORAGE LIPIDS (NEUTRAL)

• Triglycerides◦ Glycerol + 3 fatty acids






UNSAPONIFIED LIPIDS

• Terpenes

• Steroids

• Prostaglandins

• Alcohol and Ketone type

waxes

SAPONIFIED LIPIDS

• Glycerides

• Phosphoglycerides

• Sphingolipids

• Ester type waxes






Complex Lipids• Phospholipids

• Sphingolipids

• Glycolipids

• Lipoproteins

• Sulfolipids

• Aminolipids

Simple Lipids• Fatty acids

• Neutral fats (Triglycerides)

• Waxes

Derived Lipids• Eicosanoids

• Steroids

• Ketone bodies

• Fat-soluble vitamins






3. GLYCERIN-FREE LIPIDSA. Sphingolipids

i. Ceramides

ii. Sphingomyelins

iii. Glycosphingolipids

B. Aliphatic alcohols and waxes

C. Terpenes

D. Steroids

4. Lipids linked to other class compoundsA. Lipoproteins

B. Eicosonoids

C. Lisophosphoglycerides

D. Lipopolysaccharides

1. FATTY ACIDS

2. GLYCERIN CARRIED LIPIDSA. Neutral Oils

i. Mono-, di- and triglycerides

ii. Glycerin ethers

iii. Glycosylglycerols

B. Phosphoglyceridesi. Phosphatides

ii. Diphosphatidylglycerin andPhosphatidylinositol.






Definition, Nomenclature, Numbering, Classification,

Essential Fatty Acids, Physical and Chemical Properties

Fatty Acids





Fatty AcidsThey form the most important class of lipids and are

long-chain organic acids with 4-28 carbon atoms.

It has a hydrocarbon tail and a carboxyl group in its

structure.

In other words «Fatty acids are monocarboxylic

organic acids with hydrocarbon chains»• They are obtained predominantly from the hydrolysis of

triglycerides.

They are insoluble in water and show grease character.





Fatty Acids Fatty acids are not found freely in cells and tissues.

Most of the fatty acids form complexes with other

lipid molecules.• E.g. Triglycerides, phospholipids.

They are enzymatically or chemically hydrolyzed from

the tissues or from where they are.

Free fatty acids are found in the cells at very low levels.





Unesterified forms are called free fatty acid (FFA / non-

esterified fatty acid, NEFA), and this form is

transported in the plasma with the link to the albumin.

About 100 different fatty acids have been identified

from various plants, animals and microorganisms.

The majority of the fatty acids present in the animal are

unbranched, straight-chain derivatives and have a

number of double carbon atoms.

Fatty Acids





Fatty Acids Fatty acids are separated from each other by the

number of carbon atoms in the structure or the double

bond structure and chain lengths they contain.

Almost all of the fatty acids found in nature have

double carbon atoms. 16 and 18 C atoms are mostly

found.• Palmitic acid is a common 16 C fatty acid.

• There are both polar and non-polar parts in the structure.

• The hydrophobic part of a lipid is always bigger.





Palmitic Acid(C16H32O2)

Skeletal structurePolar C─O and O─H bonds

Nonpolar C─C and C─H bonds

Hydrophilic

head

Hydrophobic

hydrocarbon chain





Fatty AcidsThere are two different types of fatty acids.

• Saturated Fatty Acids: Fatty acids which have a long

hydrocarbon tail and contain only single C─C bonds. For

example; Palmitic acid and Stearic acid.◦ This group includes short chain volatile acids (short-chain fatty acids)

obtained as a result of microbial carbohydrate fermentation.

◦ Especially in rumen this event is very important for ruminants.

◦ Acetic acid (C2) is the simplest short-chain or volatil fatty acid

(VFA).

◦ In animals, palmitic acid (C16) is obtained by lipogenesis, from which

other saturated and unsaturated fatty acids are synthesized.





Fatty Acids• Unsaturated Fatty Acids: There are one or more double

bonds (C=C) in the structure.◦ If there is only one double bond in the structure, it is called

monounsatured fatty acid.

◦ If there is more than one double bond, it is called polyunsaturatedfatty acid.

◦ Unsaturated fatty acids are dominant over saturated fatty acids, especially in animals living in cold environments and in highlyorganized plants.

◦ Because of the diversity of the double bonds, they have isomers.

◦ The geometric isomerism (cis- or trans-) is observed according to the orientations of the groups connected to the double bonds.

◦ If the groups are on the same side, it is called cis-configuration. Ifthe groups are on the opposite side, it is called trans-configuration.





Fatty Acids◦ The double bond of oleic acid is in cis-configuration and twisted at

the double bond location, so appearing L-shaped.

◦ Elaidic acid is in trans-configuration and protects the flat form

(straight chain) where double bonds are present.

◦ Most natural long chain unsaturated fatty acids have cis-

configuration. For example Arachidonic acid 4 has double bonds in the

cis-configuration and it is U-shaped.

◦ Some trans-unsaturated fatty acids (e.g. Elaidic acid) are found in

ruminants (due to rumen flora). Moreover, their presence in vegetable

oils, such as margarine, led to their health questioning. – They cause problems like hypercholesterolemia, atherosclerosis, coronary

atherosclerosis and essential fatty acids in metabolism.





Fatty AcidsThe most abundant fatty acids in mammalian living

beings are oleic acid (18:1), palmitic acid (16:0) and

stearic acid. (18:0).• Fatty acids between 14-24 C can be synthesized and stored,

with the most 16-18 C in the mammals.

A saturated fatty acid

No double bonds in long chain structure

An unsaturated fatty acid

There is one cis-double bond in the long chain

structure.

Stearic AcidOleic Acid

Cis- double bond





Fatty AcidsMammalians can synthesize saturated and

monounsaturated fatty acids.

The most common unsaturated fatty acids in animal lipids are palmitoleic, oleic, linoleic and arachidonicacids.

Oleic acid is the most common fatty acid in nature. Itwas detected that all known natural oils and phospholipids have oleic acid.





Fatty AcidsHowever, nutrients must contain polyunsaturated fatty

acids (PUFAs).• These fatty acids must be taken from nutrients by mammals,

because they can not synthesize and/or synthesize enough to

meet their needs.

Linoleic acid (18:2), which can not be synthesized by

mammals, is found in vegetable oils. Linolenic acid

(18:3) is abundant in fish oils and both are essential

fatty acids.





Saturated fatty acids with a 10 or less C atom are rarely

found among animal lipids.

Bacteria contain simpler saturated fatty acids. However,

mono-saturated fatty acids are also found.

Polyunsaturated fatty acids usually contain a double

number of C atoms.• Those containing a single number of C atoms are rare in living

creatures on land (trace level). But it is found in high amounts

in sea creatures.

Fatty Acids





Each fatty acid has a generic name according to trivial naming (common names). For example Oleic acid, stearic acid etc…

According to IUPAC systematic naming, fatty acids are named according to hydrocarbons having the same number of carbon atoms.

In this system, "-e" suffix of the hydrocarbon arereplaced with the suffix "-oic asit".

Nomenclature of Fatty Acids





For this reason;• Saturated fatty acids terminate with the suffix "-anoic".

◦ A saturated fatty acid of 10 carbons; Decanoic acid = capric acid or

◦ A saturated fatty acid of 18 carbons; Octadecanoic acid = stearic acid.

• Doubly bonded unsaturated fatty acids terminate with

the suffix "-enoic acid".◦ 18 carbons, an unsaturated single double bonded, and a double bond in the

chain between the 9th and 10th carbons; 9, octadecaenoic = oleic acid or

◦ 18 carbons with 3 double bonds and double bonds in positions 9-10, 12-13

and 15-16; 9,12,15 octadecatrienoic = alpha-linolenic acid.

– 9,12,15 octadecatrienoic acid or α-linoleic acid refers to the number of carbon atoms

that double bonds start to show the position of the unsaturated bond, and to the

number of double bonds to indicate the number of double bonds.






Nomenclature of Fatty AcidsThe naming of fatty acids follows the Greek

alphabetical order.

The names α (2nd C), followed by β (3hr C) and γ (4th

C) are given to the carbon atoms after the carboxyl

group (COOH - 1st C).

The farthest C atom (Terminal group, CH3 group) from

the carboxyl group is named ω.• If there are more than one double bond, these double bonds

are not conjugated (-CH=CH-CH=CH-), separated by a

methylene group. For example: -CH=CH-CH2-CH=CH-





ω αβγδ

ω α

β

γ

δ

16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1

16:0

Palmitic Acid(C16H32O2)

Skeletal structure





Nomenclature of Fatty Acids Numbering and display of unsaturated fatty acids can be

done in two ways.1. Starting from the COOH head: There is a double bond

between the 9th and 10th carbon atoms in the majority of the unsaturated fatty acids.

◦ Starting at C 'in COOH, C atoms are numbered.

◦ The carbon atom in which the unsaturated bond is located is designated Δ sign and the atomic number of the C atom to which the bond begins is written as Δ9.

◦ If it contains more than one double bond, the double atom at which the double bonds begin is written by adding a comma (Δ9,12,15).

◦ If it is to be written without specifying Δ, write C atom number followed by «:», double bond number followed by «;» and C atom numbers at which double bonds start (e.g. 18:2;9,12).





Nomenclature of Fatty Acids2. Starting from the Omega-C atom (CH3 terminal end)

◦ Unsaturated fatty acids are sometimes classified as omega-nacids.

◦ C atoms are numbered starting from ω-C or n-C atom.

◦ The C atom number of the first double bond indicates the ωgroup in which the fatty acid is present. (E.g. In Omega-3, first double bond is located at C atom number 3, or written as n-3).

◦ Then with the order; The total number of C's, «:» followed by the number of double bonds, followed by «;» and the number of C atoms at which double bonds start.

◦ As a result, if an unsaturated fatty acid is to be written according to omega classification, first the omega group is specified. Subsequently, the total number of C atoms, the number of double bonds, and the positions where double bonds are present is written (for example: ω6, C18: 2, 6,9 or n-6,18: 2;6,9).





IUPAC Numerical Multiplier


Number Multiplier Number Multiplier Number Multiplier

1 mono- 11 undeca- 21 heneicosa-/henicosa-

2 di- 12 dodeca- 22 docosa-

3 tri- 13 trideca- 23 tricosa-

4 tetra- 14 tetradeca- 24 tetracosa-

5 penta- 15 pentadeca- 25 pentacosa-

6 hexa- 16 hexadeca- 26 hexacosa-

7 hepta- 17 heptadeca- 27 heptacosa-

8 octa- 18 octadeca- 28 octacosa-

9 nona- 19 nonadeca- 29 nonacosa-

10 deca- 20 eicosa-/icosa- 30 triaconta-





CH 3CH 2CH 2CH 2CH 2CH CHCH 2CH CHCH 2CH 2CH 2CH 2CH 2CH 2CH 2COOH1

Name the fatty acid starting from the COOH head.

2

α

3β

4

γ

91218

ω

• 18 Carbon atoms.

• Two double bonds on 9th and 12th carbon atoms.

• Δ9,1218:2 or,

• 18:2;9,12.• Fatty Acid is,

• Linoleic Acid (9,12-octadecadienoic acid)





18

Name the fatty acid starting from the CH3 terminal end.

171615961

ω

• 18 Carbon Atoms.

• Two double bonds on 6th and 9th carbon atoms.

• The first double bond is at 6th C so it is an ω6 or n-6.

• ω6,C18:2;6,9 or,

• n-6,18:2;6,9.• Fatty acid is,

• Linoleic Acid (9,12-octadecadienoic acid), an ω6 fatty acid.

CH 3CH 2CH 2CH 2CH 2CH CHCH 2CH CHCH 2CH 2CH 2CH 2CH 2CH 2CH 2COOH





Linoleic Acid (Unsaturated)





Naming according to COOH head

• Δ6,9,12,1518:4

• 18:4;6,9,12,15

Naming according to CH3 terminal end

• ω3,C18:4;3,6,9,12

• n-3,18:4;3,6,9,12

6,9,12,15-octadecatetraenoic acidt

Stearidonic acid






• Δ5,8,11,14,1720:5

• 20:5;5,8,11,14,17


• ω3,C20:5;3,6,9,12,15

• n-3,20:5;3,6,9,12,15

5,8,11,14,17-eicosapentaenoic acid

Timnodonic Acid






• Δ5,8,11,14 20:4

• 20:4;5,8,11,14


• ω6,C20:4;6,9,12,15

• n-6,20:4;6,9,12,15

5,8,11,14-eicosatetraenoic acid

Arachidonic Acid

5

8

11

14

6

9

12

15

ω

αβ 1

1

20





Draw the fatty acid mentioned above.

all-cis-7,10,13,16,19-docosapentaenoic acid

Clupanodonic Acid





Classification of Fatty Acids

Acetic Acid (2:0)

Propionic Acid (3:0)

Butyric Acid (4:0)

Valeric Acid (5:0)

Caproic Acid (6:0)

Caprilic Acid (8:0)

Capric Acid (10:0)

Lauric Acid (12:0)

Myristic Acid (14:0)

Palmitic Acid (16:0)

Stearic Acid (18:0)

Arachidic Acid (20:0)

Behenic Acid (22:0)

Lignoceric Acid (24:0)

Serotic Acid (26:0)

Montanic Acid (28:0)

SATURATED FATTY ACIDS






Palmitoleic Acid (16:1;9-ω7)

Oleic Acid (18:1;9 (cis)–ω9)

Elaidic Acid (18:1;9 (trans)–ω9)

Vacsenic Acid (18:1;11-ω7)

Linoleic Acid (18:2;9,12–ω6)

γ-Linolenic Acid (18:3;6,9,12–ω6)

α-Linolenic Acid (18:3;9,12,15–ω3)

Arachidonic Acid (20:4;5,8,11,14–ω6)

UNSATURATED FATTY ACIDS

Timnodonic Acid(20:5;5,8,11,14,17 – ω3)

Eruadic Acid (22:1;13 – ω9)

Klupanodonic Acid(22:5;7,10,13,16,19 – ω3)

Cervonic Acid(22:6;4,7,10,13,16,19 – ω3)

Nervonic Acid (24:1;15 –ω9)






ω3

• α-Linolenic Acid (18:3;9,12,15-ω3)

• Timnodonic Acid (20:5;5,8,11,14,17–ω3)

• Klupanodonic Acid (22:5;7,10,13,16,19–ω3)

• Servonic Acid (22:6;4,7,10,13,16,19–ω3)

ω6• Linoleic Acid (18:2;9,12–ω6)

• γ-Linolenic Acid (18:3;6,9,12–ω6)

• Arachidonic Acid (20:4;5,8,11,14–ω6)

OMEGA CLASSIFICATION of Unsaturated Fatty Acids

ω7• Palmitoleic Acid (16:1;9-ω7)

• Vacsenic Acid (18:1;11-ω7)

ω9• Eruadic Acid (22:1;13–ω9)

• Nervonic Acid (24:1;15-ω9)• Oleic Acid (18:1;9 (cis)–ω9)

• Elaidic Acid (18:1;9 (trans)–ω9)






Short-Chain FAs• Asetic acid (2:O)

• Propiyonic acid (3:0)

• Butyric acid (4:0)

• Valeric acid (5:0)

Medium-Chain FAs• Caproic acid (6:0)

• Caprilic acid (8:0)

• Capric acid (10:0

• Laurl acid (12:0)

Long-Chain FAs• Miristoleic acid (14:1)

• Miristic acid (14:0)

• Palmitoleic acid (16:1;9)

• Palmitic acid (16:0)

• Stearic acid (18:0)

• Oleic acid (18:1;9 (cis))

• Linoleic acid (18:2;9,12)

• Linolenic acid (18:3;6,9,12)

• Arachidonic acid (20:4;5,8,11,14)

• Arachidic acid (20:0)

• Lignoceric Acid (24:0)





Short-Chain Fatty AcidsAcetic Acid (2:0)

• It is major final product of symbiotic microbes.

Propiyonic Acid (3:0)• It is the end product of carbohydrate fermentation by

symbiotic microbes. It’s a gluconeogenic fatty acid.

Butyric Acid (4:0)• It is the main end product of carbohydrate fermentation

carried out by simbiotic microbes.

Valeric Acid (5:0)• It is the minor end product of carbohydrate fermentation

carried out by symbiotic microbes.





Caproic Acid (6:0)• It is the minor end product of carbohydrate fermentation

carried out by symbiotic microbes.

Caprilic Acid (8:0)• Also known as octanoic acid.

• It is found in vegetable oils.

Lauric Acid (12:0)• It's found in sperm.

Medium-Chain Fatty Acids





Miristic Acid (14:0) • It is found in vegetable oils.

Palmitic Acid (16:0)• It is found in vegetable and animal oils.

Stearic Acid (18:0)• It is found in vegetable and animal oils.

Arachidic Acid (20:0)• It is found in high amounts in peanut oil.

Behenic Acid (22:0) • It is found in high amounts in the seeds.

Long-Chaind Fatty Acids





Palmitoleic Acid (16:1;9-ω7)• It is found in most lipids.

Oleic Acid (18:1;9 (cis)–ω9)• It is widely found in neutral lipids.

Elaidic Acid (18:1;9 (trans)–ω9)• Ruminant lipids.

Vacsenic Acid (18:1;11-ω7)• It is created by the bacteria.

Linoleic Acid (18:2;9,12–ω6)• It is found in plants and animals.

Unsaturated Fatty Acids





γ-Linolenic Acid (18:3;6,9,12–ω6)• It is found in plants and animals.

• Linoleic acid derivative.

α-Linolenic Acid (18:3;9,12,15–ω3)• It is commonly found in fish fats.

Arachidonic Acid (20:4;5,8,11,14–ω6)• It is also called Eicosatetraenoic acid.

• It is found in animal phospholipids.

Timnodonic Acid (20:5;5,8,11,14,17–ω3)• Also known as Eicosapentaenoic acid.

• It is commonly found in fish fats.






Eruadic Acid (22:1;13 – ω9)• It is found in mustard seed oil.

Clupanodonic Acid (22:5;7,10,13,16,19 – ω3)• It is named as Docosapentaenoic acid.

• It is found in fish fat and in the brain phospholipids.

Cervonic Acid (22:6;4,7,10,13,16,19 – ω3)• It is named as Docosahexaenoic acid.

• It is found in fish fat and in the brain phospholipids.

Nervonic Acid (24:1;15 – ω9)• It is named as Tetracosenoic acid.

• It is found in the cerebrocytes.






They were first detected ~60 years ago.

Because they can not be synthesized by the organism, they are fatty acids which must be taken with nutrients.

Linoleic acid, which is one of the unsaturated fatty acids, is considered to be a true essential fatty acid. It can not be synthesized by mammals.

Linoleic acid is found in the structure of triglycerides and glycerophospholipids by 10-20%.

Essential Fatty Acids





Linoleic acid, arachidonic acid and timnodonic acid

can be synthesized by mammals over linoleic acid.

However, since this synthesis is not at a level that meets

the needs, these fatty acids must also be taken with

foods.

Thus, linoleic acid, linolenic acid, arachidonic acid and

timnodonic acid are essential fatty acids.






Some disorders arise as a result of inadequate intake with food or no intake.• Deficiencies are characterized by skin problems such as

lesions, dryness and a decline in growth.

Essential fatty acids are required for the synthesis of eicosanoids (prostaglandins, prostacyclins, thromboxanes, leukotrienes, lipoxins).• These compounds have hormone-like effects and are present in

trace amounts, but their physiological effects are very important.






Both physical and physiological properties of fatty acids depend on the length of the carbon chain and on the number of double bonds in the molecule (the degree of unsaturation of the fatty acid).

Fatty acids are amphipatic and have both hydrophobic and hydrophilic domains. This binary structure generally plays a key role in the function of biological lipids against water.• Hydrocarbon groups try to combine to form a minimum surface with

the carboxyl groups forming a contact surface around the mass of water.

• The chain length of the hydrocarbon group is determined by superior behavior. Hydrophobic structures are very strong inpalmitic acid.

Physical Properties of Fatty Acids





Fatty acids are not water-soluble, but their Na+ and K+ salts are soluble in water.

The Na+ and K+ salts of fatty acids emulsify oils and water-insoluble fatty substances.• Na and K soaps dissolve in water and they are cleaners. Others are

not soluble in water and are not cleaners. Commercial soaps are Na salt of palmitic, stearic and oleic acid.

Ca+2 or Mg+2 soaps of fatty acids are very difficult to dissolve in water and thus can not emulsify fatty layers. When K soaps are used in hard water (calcareous water) containing Ca and Mg, they do not dissolve in the water and precipitate to the bottom.






The polar head of soap forms a hydrophilic cover around

fatty part and the fat droplets are reduced into smaller

pieces, so the lipid layer is removed.

Bath soaps are a general mixture of fatty acids with

potassium soaps. Sodium or potassium soaps are

amphipathic. Ionized carboxyl head is polar and tail part

is nonpolar.






Physical Properties of Fatty Acids All saturated fatty acids with a carbon number up to 10

are liquid and volatile at ordinary temperature. Fatty acids with a carbon number greater than 10 are solid at body temperature.

As the carbon chains of the fatty acids increase, the fatty acid hardens and the melting point begins to rise.

Unsaturated fatty acids are liquid at room temperature due to double bonds in the structure. Also, as the number of double bonds increases, the melting point begins to fall.• For example: The 18:2 unsaturated fatty acids are liquid at 0° C.

Unsaturated fatty acids have high reactivity due to the double bonds they carry.





In practice, natural acyl glycerols contain fatty acid mixtures which are shaped to fit their functional roles. For example, membrane lipids that must be liquid in

all environmental temperatures contain more unsaturated fatty acids than storage lipids. In tissues encountering cold, eg. Lipids found in pigs or

hibernating animals or on the extremities of animals are more unsaturated. • In other words, living beings living in cold regions have more

unsaturated fatty acids in membrane lipids than living in warm regions. The glycerides, which are rich in saturated fatty acids, are solid.






Almost all of the naturally occurring long chain

unsaturated fatty acids are in the cis- configuration

However, in the case of unsaturated fatty acids, the

isomeric forms of the double bonds are the cis- and

trans- isomers which appear as isomeric forms,

depending on the sequence around the double bond.• For example, oleic acid has a melting point of +13°C and cis.

When oleic acid is treated with nitric acid, the trans-form of

elaidic acid occurs. The melting point of elaidic acid is +45°C.






Doubly bonded fatty acids are oxidized by strong

oxidizing agents such as hydrogen peroxide (H2O2) and

superoxide anion radicals (˙OH, O2˙).

These substances are toxic to the cell.

Accordingly, peroxidation of lipids in the cell membrane

leads to deterioration of membrane protein structure.

Chemical Properties of Fatty Acids





Salts of Fatty Acids• The salts of fatty acids whose carbon number is higher than

6 are called soap.

• The ionic head of soaps form a polar group to bind with water

by hydrogen bonding.

• Non-polar tail are assembled together. So soap molecules that

are dispersed in water form mycelia.

• Na and K soaps dissolve in water and are cleaners. Others are

not soluble in water and are not cleaners.






• Potassium soaps are softer than sodium soaps and melt faster.

The soaps of unsaturated fatty acids are more soluble in water

and alcohol than in saturated ones.

• The soaps sold in the market are the sodium salts of the same

fatty acids. There are sodium carbonate and sodium silicate to

make the water softer.

• Potassium salts of palmitic, stearic or oleic acid are known

as arabic soap (soft soap).






• Calcium soaps of long chain fatty acids are found in the

addition of engine oils.

• Aluminum soaps have been used in the industry since they

have formed a durable gel.

• Cleaners called detergents have been developed. These

substances are usually alkylbenzenesulfonates, a family of

compounds that are similar to soap but are more soluble in

hard water.






Detergent Formation• Detergents are metal (such as Na, K, Ca, Mg) salts of sulfuric

acid esters of higher alcohols which are reduction products of fatty acids.

• Fatty acid first turns into alcohol, which is done with high pressure and heat.

• Detergents can be used more easily in hard water as they form Ca+2 and Mg+2 salts. Cleaning ability is more.

• Since they are sulfuric acid esters, their salts are superior cleaning agents due to their not breaking up in acid solutions.

• Even with acid, they do not break down and cause environmental pollution.






• Since some of the detergents contain K+ , such detergents are

more environmental pollutant.

• Because K+ is a good growth factor for the growth of green

algae living in sweet water (fresh water).

• Along with the mixing of detergents into the surrounding

waters, algae growth in water is increased and therefore the

amount of oxygen in the water decreases.

• Decreasing oxygen in the water will cause aquatic organisms to

die especially fish.






Ester formation.• The carboxyl groups of fatty acids are reversibly associated

with alcohols.

• The esterification is self-slow, but is rapid in the presence of

heat or hydrogen ions.

Features of Double Bond• Hydrogenation: It is the saturation of the ethylene bond (-

CH=CH-) in the structure of unsaturated fatty acids with

hydrogen. For example: When oleic acid is hydrogenated,

stearic acid is formed, meaning the unsaturated fatty acid is

converted to saturated fatty acid.






• Addition a halogen to double bond: They are saturated by

adding halogen to the double bonds. This process takes place

in the presence of catalysts such as Br, Pt, Ni, F, Cl, I and Cu at

high pressure.

• Oxidation: Oxidation of ethylene bonds.◦ KMNO4 is used as the oxidant in the oxidation of fatty acids. Since the

oxidation process is very complex, many intermediate metabolites

may form during oxidation.

◦ Ozonoide is an any of a class of unstable cyclic compounds formed by

the addition of ozone to a carbon–carbon double bond.

• These reactions are used to determine which carbon atoms are

joind to double bongin in an any unsaturated fatty acids.






• Peroxidation: Peroxidation of polyunsaturated fatty acids,

which is formed in vivo and is called lipid peroxidation, is a

chain reaction.

◦ During the reaction, very reactive free radicals are formed

which contain unpaired electrons.

◦ Free radicals enter into wide-ranging reactions in living

organisms.

◦ However, the defense system (antioxidative system) in the

organism prevents or controls the harmful effects of these

compounds.






Glycerin

Neutral Lipids (Mono-, di- and triglycerides, Glycerin ethers, Glycosylglycerols)

Phosphoglycerides (Phosphatides, Diphosphatidylglycerin and Phosphatidylinositols)

Lipids carrying Glycerin





Glycerin Also known as glycerol. It is a trivalent polyol with a

sweet, thick, colorless, odorless and liquid character.

It forms the backbone of glycerolipids.• Glycerin may be miscible with water and ethyl alcohol in any case

and will not dissolve in ether, chloroform and benzene.

• If it is oxidized with hydrogen peroxide under the catalytic action

of iron salts in a slightly alkaline medium, a mixture of

glyceraldehyde and dihydroxyacetone occurs.

• Due to its water-absorbing and moisturizing properties, it is a

desirable ingredient in cosmetic and pharmaceutical products. It is

used in the production of some explosive substances (nitroglycerin).

• It is easily ingested by animals.





Glycerol(1,2,3-propanetriol)

Dihydroxyacetone Glyceraldehyde

1

2

3

1

2

3

sn-1

sn-2

sn-3

Chirality?





Neutral lipids are esters of fatty acids with glycerol.

They form the most common class of lipids.

Among the vegetable oils; olive, cottonseed, linseed,

coconut, peanut, soybean and poppy oils are the most

important and common.

It is found in all animal tissues in more or less amounts.

Neutral Lipids





Lipid storages have three important functions.1. They are substitute nutrients.

2. They serve as insulators against heat loss from the body.

3. They serve as cushions to protect the internal organs from

external impacts.

Classification;• Mono-, di- and triglycerides

◦ Fats (animal) and Oils (herbal)

• Glycerin ethers

• Glycosyl glycerines

Neutral Lipids





When an alcohol group of glycerin is esterified with a

one mole fatty acid, monoglyceride occurs.

When two alcohol groups of glycerin is esterified with a

two mole fatty acids, diglyceride occurs.

When three alcohol groups of glycerin is esterified with

three mole fatty acids, triglyceride occurs.

Mono-, di- and triglycerides





Triglycerols (Triacylglycerol) or triglycerides

(Triacylglycerines) are triesters which are formed by

esterification of 3 fatty acids and glycerol.

In general, the structure of the fat is triglyceride. Often

triglycerides are used for fats.• The lipids in animal and vegetable oils are mostly

triglycerides.

• These are a concentrated metabolic energy source of 9 kcal/g.






Glycerol Triglyceride

(Ester groups are shown

with red color)

Diagram of

Triglyceride

Gly

cero

l

Fatty Acids

R group contains 11-10

C atoms.

Fatty Acid

Fatty Acid

Fatty Acid





Palmitic Acid

Oleic Acid

α-Linolenic Acid

Gly

cero

l

C55H98O6

Triacylglycerol (TAG-TG)(1-palmitoil-2-oleil-3-α-linolenoil-glycerol/POL)





Both animal fats and vegetable oils, if necessary, are highly

complex esters of fatty acids with glycerin. These esters are

called glyceride.

The fatty acids in glycerides can also be the same or

different.• If all three of the esterified fatty acids are the same, simple

(homogeneous) glycerides form. For example, if three moles of

stearic acid is bound to a glycerol, it is called stearin/tristearin. If

3 moles of oleic acid is bound, it is called olein.

• When fatty acids esterified to glycerol to form glyceride are

different from each other, mixed (heterogeneous) glycerides

occur.






Physical Properties of Triglycerides

The fatty acids in the triglycerides may be saturated

and/or unsaturated. Animal fats and vegetable oils are

triglycerides with different physical properties.

Animal fats have a high melting point. They are solid at

room temperature.

Vegetable oils have a low melting point. They are liquid

at room temperature.





To understand that a triglyceride is a fat or an oil, fatty

acids in its structure must be taken care.

As the number of double bonds in the fatty acid chain

increases, the melting point of triglyceride decreases.

While animal fats are composed of low double bond

fatty acids, vegetable fats are composed of high double

bond fatty acids.






Solid fats have saturated fatty acids in relatively high proportions and are generally of animal origin.• Pork oil, butter and whale shell high in saturated fat.

• Without double bonds, the three side chains of saturated lipid extend parallel to each other and have a high melting point.

Liquid oils have a higher percentage of unsaturated fatty acids and are usually of vegetable origin.• Fats extracted from corn, soybean oil and olives contain more

unsaturated lipids.

• Unsaturated lipids, a cis- double bond, forms a bend in the side chain and makes it more difficult to pack efficiently in solid form. This leads to a lower melting point.







Melting points are higher than the melting point of the

fatty acid they carry.

Short chain fatty acids are soluble in both water and

organic solvents. Long chain fatty acids do not dissolve

in water, but dissolves in organic solvents.

Except for the lipids of hydroxy-fatty acids, other lipids

dissolve in boiling petroleum ether.






The specific gravity of oils and fats is lower than water.

Pure glycerides are colorless, odorless, tasteless. If a

glyceride has color, odor and taste, it is derived from

foreign substances mixed with glycerides.

The yellow color of the butter comes from the presence

of herbal pigments called carotene and xanthophylls.

Unsaturated fatty acids of liquid oils can be solidified by

saturating with hydrogen. Structures that are solidified

by hydrogenation are called margarine.





Hydrolysis• Triglycerides are hydrolyzed by boiling with acids or bases

under normal pressure or with water under high pressure or

by catalytic action of certain enzymes; lipase.

• The formation of unpleasant odor and taste in oils known as

aggravation is partly due to the release of fatty acids.

• Hydrolysis of triglycerides yields 1 mole of glycerol and 3 mole

of fatty acid.

Chemical Properties of Triglycerides





Hydrolysis cleaves the three single bonds between the carbonyl carbons

and the oxygen atoms of the esters. Since tristearin contains three

identical R groups on the carbonyl carbons, three molecules of a single

fatty acid, stearic acid, are formed.

The three

bonds drawn

in red are

broken in

hydrolysis.

Glycerol

Stearic acid

Tristearin





Glycerol

Stearic acid

Palmitic acid

Palmitoleic acid





Saponification• Soap is prepared by the basic hydrolysis (saponification) of a

triacylglycerol. Heating an animal fat or vegetable oil with

aqueous base hydrolyzes the three esters to form glycerol

and sodium salts of three fatty acids.

• Saponification Value: It is expressed by potassium hydroxide

(KOH) in mg required to saponify one (1) gram of fat.◦ The saponification value is regarded as an index showing the average

molecular weight of fatty acids.

◦ Some soaps, especially Na and K soaps, are easily soluble in water

because the dissolution of the carboxylic groups is quicker.






Sodium stearate is the sodium salt of stearic acid, an

18-carbon saturated fatty acid.

Sodium stearate ionic endpolar head long hydrocarbon chain

nonpolar tail





TrioleinGlycerol

Sodium oleat

soap






Separation of fatty acids• It is the phenomenon of separating fatty acids in an fat or oil.

• This reaction makes it possible to remove fatty acids in an oil

or fat in free form.

Hydrogenation• Unsaturated bonds in fats are saturated with hydrogen.

• The unsaturated bonds of fatty acids in the oils are saturated

with hydrogen to yield margarines.






Halogenation• The unsaturated bonds of fatty acids are saturated with

halogens such as Cl, Br, I.

• Iodine Value: It is the mass of iodine in grams that is consumed by 100 grams of a fatty acid.

• The iodine value is an indication of the relative unsaturation of oils.

Oxidation• It occurs when O3 or O2 is added to the double bonds of the

double acids of unsaturated fatty acid. The aggravation of the oil is partly due to the hydrolysis and the partial oxidation.





Chemical Properties of TriglyceridesAcetylation

• Fats or oils which carry fatty acids with free hydroxyl groups

are acetylated with acetic anhydride.

• Acetyl Number: A measure of free hydroxyl groups in fats or

oils determined by the amount of potassium hydroxide used

to neutralize the acetic acid formed by saponification of

acetylated fat or oil.

• The acetyl number gives the average amount of oxy-acids in

the fat or oil.





Chemical Properties of TriglyceridesRancidification

• It is the process which causes a substance to become rancid, that is, having a rank, unpleasant smell or taste.

• Acid Value◦ It is the mass of potassium hydroxide (KOH) in milligrams that is

required to neutralize one gram of free fatty acid. It is regarded as an index of rancidity caused by free fatty acids.

• Reichert Value (Reichert-Meissl-Wollny Value)◦ It is an indicator of how much volatile fatty acid can be extracted

from fat through saponification. It is equal to the number of milliliters of 0.1 normal hydroxide solution necessary for the neutralization of the water-soluble volatile fatty acids distilled and filtered from 5 grams of a given saponified fat.





Chemical Properties of TriglyceridesCauses of rancidification;1. Hydrolytic rancidity refers to the odor that develops when

triglycerides are hydrolyzed and free fatty acids are released.

2. Oxidative rancidity is associated with the degradation by

oxygen in the air. Via a free radical process, the double bonds

of an unsaturated fatty acid can undergo cleavage, releasing

volatile aldehydes and ketones. Oxidation primarily occurs

with unsaturated fats.

3. Microbial rancidity refers to a process in which

microorganisms, such as bacteria or molds, use their enzymes

such as lipases to break down fat.





Glycerin Ethers: They are lipids in which one or more

of the carbon atoms on glycerol is bonded to an alkyl

chain via an ether linkage, as opposed to the usual

ester linkage. It is found in animal tissues (shark and

whale fat).

Glycosylglycerols: A class of glycolipids structurally

analogous to phospholipids; they are the major

glycolipids of plants and microorganisms but are rare in

animals. Contain high levels of linoleic acid.

Neutral Lipids





Phospholipids: They are lipids containing a phosphate

group in its molecular structure together with fatty

acids and alcohols. There are 2 classes.

• Phosphoglycerides (Glycerophospholipids): Glycerides which

carry phosphoric acid esterified with glycerin/gycerol

(glycerophospholipids).

• Sphingophospholipids: Glycerides which carry phosphoric acid

esterified with sphingosine alcohol.

Phospholipids





Phospholipids are both structurally and functionally

important.• They are the basic building blocks of cell membranes.

• They are important components of lipoproteins.

• They function in intracellular signal transduction pathways like

lipid signaling (LPA, S1P, PAF, PIP ...).

• They are involved in blood coagulation (phosphotidylserine).

• They are found in the bile secretion (phosphatidylcholine).

• They are involved in the structure of the pulmonary

surfactants (phospholipoprotein).

Phospholipids





Phosphoglycerides are much more than sphingolipids and form a family with different structures.

Fatty acid is present at the C1 and C2 positions of glycerol. Usually;• The fatty acid in C1 is saturated,

• Fatty acid in C2 is an unsaturated fatty acid.

• The most common fatty acids are palmitic, stearic, oleic, linoleic and arachidonic acids.

In the C3 position, the phosphate ester is present, which is esterified with the hydroxy group of the İnositol or with the hydroxy group of one of the 3 nitrogenous bases; Choline, Serine or Ethanolamine.

Phosphoglycerides (Glycerophospholipids)





They are common in all animal and plant cells.

They are mostly found in eggs, brain, liver, kidney,

pancreas, lung and heart.

They are separated from other lipids by their dissolution

in acetone.

They are separated into 3 groups as Phosphotides,

Diphosphatidylglycerol (Cardiolipin) and

Phosphoinositides.

Phosphoglycerides (Glycerophospholipids)





Phosphatides are widely found in nature.Their glycerin is esterified with only 2 fatty acids.The 3rd -OH group of glycerin is a phosphodiester

moiety. This phosphodiester is attached to an alkyl group (R) derived from a low molecular weight alcohol.They are glycerophosphate derivatives and often

carry a nitrogenous base. This group contains lecithin, cephalin, phosphatidylserine, plasmalogens andplatelet-activating factor (PAF).

Phosphatides





Phosphatides Lecithin (Phosphatidylcholine)

• Glycerophosphate derivatives. It's a nitrogenous base.

• Except for the choline, the remainder is called phosphatidic

acid.

• Lecithin is therefore also called phosphatidylcholine.

• The fatty acids in the structure may be saturated or

unsaturated.

1 mole Glycerine + 2 moles Fatty acids + 1 mole H3PO4 + 1 mole Choline

LECITHIN





Phosphatides• Choline are also considered as vitamin.

• Inadequacy leads to some disorders such as fatty liver and

hemorrhage in kidneys.

• The phosphorylase A enzyme can partially hydrolyze lecithin.

This enzyme can be found in snake venom, hornet venom and

some microorganisms.◦ When hydrolyzed with phosphorylase A, 1 mole of fatty acid is

removed and the remaining part is called lysolecithin or

lysophosphatidylcholine. This molecule has a strong hemolytic effect.

• They are insoluble in water, but have a great deal of water.

Perhaps it is one of the most important elements of

protoplasm.





PhosphatidesCephalin (Phosphatidylethanolamine)

• They are similar with lecithin.

• The only difference between them is the presence of

ethanolamine (colamine) instead of choline.

1 mole Glycerine + 2 moles Fatty acids + 1 mole H3PO4

+1 mole Ethanolamine

CEPHALIN





Phosphatides• Fatty acids in the structure are usually one saturated and an

unsaturated.

• In lecithins, two fatty acids can be saturated or unsaturated.

This is a difference between the two.

• It is found in all body tissues, especially in the brain.

• Especially they are located in the structure of cellular

membranes.

• Cephalin is less soluble in alcohol than lecithin.





Lecithin Cephaline

EthanolamineCholine





PhosphatidesPhosphatidylserine

• They are similar to lecithin.

• The only difference between them is that serine is found

instead of choline, which is esterified with phosphoric acid.

• It is located on the structure of cell membranes.

• Cells function in signal pathways and coagulation.

1 mole Glycerine + 2 moles Fatty acids+ 1 mole H3PO4 + 1 mole Serine

PHOSPHATIDYLSERINE





PhosphatidesPlasmalogens

• When hydrolyzed, they give a mixture of high molecularaldehydes and esters of α- or β-glycerophosphoric acid with colamine or choline. It is an ether phospholipid.

• It is mostly found in brain-nerve cells (myelin) and muscle (cardiac) tissues.◦ It has been determined that it is present in excess amount in the

plasma membrane of cancer cells. It is thought to be involved in metastasis.

1 mole Glycerol + 1 mole High Fatty acid aldehyde (palmitaldehyde or

stearylaldehyde) + 1 mole Fatty acid + 1 mole H3PO4 + 1 mole Colamine/Choline

PLAZMALOJEN





PhosphatidesPlatelet-Activating Factor (PAF)

• It is an ether phospholipid. In the structure there is an ether-linked to long alkyl chain at the C1 position and an ester-linked to acetyl residue at the C2 position. It is synthesized by leukocytes.

• In many tissues, they have various effects. Ex. Platelet aggregation and relaxation of vascular smooth muscles. It acts in the inflammation and immune system.

1 mole Glycerol + 1 mole Fatty acid alkyl group (16C) + 1 mole Acetyl residue

+ 1 mole H3PO4 + 1 mole Choline

PAF





Two phosphatidic acid moieties connect with a glycerol backbone in the center to form a dimeric structure. It is found in all plants and animals.

• It is found on bacterial membranes and on the inner mitochondrial membrane of mammals. It is the only known antigenic phospholipid molecule.

It was first isolated from the heart muscle.Helps the formation of quaternary structure of proteins. It acts as a proton trapping agent for oxidative

phosphorylation.

Diphosphatidylglycerine (Cardiolipin)





The structure contains a group of inositol instead of

nitrogenous bases.• Inositol is a polyol and sugar alcohol (glucose).

• Inositol is involved in the myo-İnositol structure, myo-

conformer.

Phosphatidylinositols form a minor component on the

cytosolic side of eukaryotic cell membranes. But their

functions are great.

Phosphorylated forms of phosphatidylinositol are

called phosphoinositides.

Phosphatidylinositols





Phosphainositide;• 1 mole glycerin + 1 mole myo-İnositol + 2 moles of fatty

acids + 1-3 phosphoric acid.

• They are widely found in nature.

• They are involved in lipid signaling, cell stimulation and

membrane trafficking.◦ Phosphatidylinositol-3-phosphate, Phosphatidylinositol-4-phosphate,

Phosphatidylinositol-5-phosphate

◦ Phosphatidylinositol-3,4-biphosphate, Phosphatidylinositol-3,5-

biphosphate, Phosphatidylinositol-4,5-biphosphate

◦ Phosphatidylinositol-3,4,5-triphosphate

Phosphotidylinositols





Sphingolipids (Ceramides, Sphingomyelins, Glycosphingolipids [Cerebrosides,

Sulfatides, Globosides/Ceramide Oligosaccharides, Gangliosides]),

Aliphatic Alcohols and Waxes, Terpenes, Steroids

Glycerin-Free Lipids





The first group of Glycerin-free lipids are sphingolipids.

Sphingolipids carry sphingosine (18-carbon alcohol)

instead of glycerin.• They were discovered in brain extracts in the 1870s and were

named after the mythological Sphinx because of their

enigmatic nature

Sphingolipids are important structural components in

the membranes of animal and plant cells.• There is a lot in the brain and nerve tissue but store in trace

amount.

Sphingolipids





The sphingosine is an alcohol having 18 C atom, a

double bond and an amino group, so it’s also an amino

alcohol.

These compounds are regarded as derivatives of the

sphingosine base (4-sphingenine) or

dihydrosphingosine (sfinganine).• Fatty acids are linked by forming amide bond with amine

groups of sphingosine.

• Different sphingolipids come into being by binding different

substances to OH group of sphingosine.

Sphingolipids





Glycerol Sphingosine





Ceramides• They are N-acyl derivatives of sphingosine.

• Ceramides (Cer) are composed of sphingosine, which is an amide

linked to a fatty acyl chain (linked with amino group of

sphingosine), varying in length from 14 to 26 carbon atoms.◦ Synthesized in endoplasmic reticulum.

◦ There are two nonpolar tails in ceramides which are characteristic in all

sphingolipids.

◦ Ceramides form the basic structure of all sphingolipids.

• When they are hydrolyzed they give 1 mole of sphingosine and 1

mole of fatty acid.

• They are abundant in animal and plant tissues.

Sphingolipids





* There are two -OH groups at the 1st and 3rd carbon atoms.

* In particular, -OH at the 1st C atom is involved in the formation

of sphingomyelins and glycosphingolipids.

* Fatty acids in the structure are characteristic of very long

chains. Ex. Nervonic acid in brain tissue (24: 1, 15).

Sphingolipids

R: Region of fatty acid binding or Alkyl group

of fatty acid.

Sphingosine Alcohol





The Importance of Ceramides• They have been implicated in a variety of physiological functions

including apoptosis, cell growth, cell differentiation, aging, cell migration and cell adhesion.

• It is the main component of the stratum corneum in the epidermis.◦ They provide waterproofing with cholesterol and saturated fatty acids.

◦ It forms a barrier for microorganisms.

◦ Prevents excessive water loss by evaporation.

◦ With aging, the amount of ceramide and cholesterol in the stratum corneum is reduced.

• It is thought that ceramide or its metabolites play a role in the emergence of pathological conditions such as cancer, neurodegeneration, diabetes mellitus (insulin resistance), microbial pathogenesis, obesity (leptin resistance) and inflammation.

Sphingolipids





Sphingomyelins• They are phosphocholine or phosphoethanolamine

derivatives of ceramides. However, their general

characteristics are similar to those of phosphatidylcholines.◦ Endoplasmic reticulum, intestine and plasma membrane are

involved in synthesis.

• When hydrolyzed they give;◦ 1 mole of sphingosine alcohol, 1 mole of fatty acid, 1 mole of

choline and 1 mole of phosphoric acid.

◦ They are also phospholipids because they contain phosphoric acid.

Also classified as sphingophospholipids.

Sphingolipids





Examples of Sphingomyelins

The phosphodiester group is located at the terminal carbon





• Sphingomyelins are found especially in the membranes (e.g.

erythrocytes) and in the myelin sheath surrounding certain

nerve cells. ◦ The myelin sheath plays a vital role in normal nerve stimulation. For

example, in MS, impaired myelin sheath causes neurological problems.

• The fatty acids in the sphingomyelins structure vary

depending on where the sphingomyelin is found.◦ In the central nervous system, sphingomyelin contains stearic acid,

lignoseric acid and nervonic acid; in the spleen sphingomyelin contains

palmitic acid and lignoceric acid.

◦ Sphingomyelins often contain lignoceric acid as fatty acid.

Sphingolipids





Glycosphingolipids• They are carbohydrate derivatives of ceramides.

• They do not carry phosphoric acid and choline in their structure. Instead, they carry hexoses such as galactose,glucose and their N-acetyl derivatives.

• Depending on the accumulation of glycosphingolipids metabolic disorders occur.

• They are divided into 4 classes according to carbohydratesthey carry.◦ Cerebrosides

◦ Sulphatides

◦ Globosides (Ceramide oligosaccharides)

◦ Gangliosides

Sphingolipids





Sphingolipids• Cerebrosides

◦ When hydrolyzed they give 1

mole sphingosine + 1 mole

fatty acid + 1 mole galactose

or glucose. Mostly galactose.

◦ The carbohydrates are linked to

the C1 position of the

sphingosine.

◦ Galactocerebrosids are found abundantly in neuronal membranes in

the myelin sheaths of the brain and nerves.

◦ Glycoserbrosides are found mostly in extraneuronal membranes and

function as intermediates in the synthesis of complex glycolipids.





Sphingolipids◦ Cerebrosides are differentiated according to fatty acid carrying. They

carry fatty acids containing 24 C atoms. – The structure is similar to sphingomyelins. They contain carbohydrates instead of

phosphocholine.

◦ For example, if fatty acid is;– Lignoceric acid, it is called kerasin,

– Cerebronic acid, it is called cerebron (phrenosin),

– Nervonic acid, it is called nervon,

– Hydroxynervonic acid, it is called hydroxinervon.

◦ Cerebroside synthesis for the development of the nervous system

in the young is possible with the presence of carbohydrates,

especially galactose. For this reason, it is obvious how important it is

to take lactose.





• Sulphatides◦ They are sulfated galactocerebrosides.

◦ They are formed by the attachment of a sulfate residue to the 3rd carbon atom of galactose found in cerebrosides.

◦ Sulphatides are multifunctional molecules.

◦ As a cell membrane component; they have functions such as proteintrafficking, cell aggregation and adhesion, neural plasticity andmemory.

◦ It is involved in the nervous system, immune system, insulin secretion, blood clotting, viral and bacterial infections.

◦ Abnormal metabolism of sulphatides is also seen in many known metabolic diseases and is thought to be related to these pathologies.– E.g. Alzheimer's Disease, Parkinson's Disease, Diabetes mellitus.

Sphingolipids





Sulphatide

Sphingosine

Fatty acid

Galactose

Sulphate





Sphingolipids

• Globosides (Ceramide Oligosaccharides)◦ Ceramide oligosaccharides are sphingolipids that contain multiple serially

linked sugar units.

– Generally, D-glucose (GIc), D-galactose (Gal) or N-acetyl-D-galactosamine (GalNAc).

– Cerebrosides and globocytes are also called neutral glycolipids. They are neutral at pH 7.

◦ They are named according to the number of ceramide-linked sugar units, such

as Ceramide disaccharides, ceramide trisaccharide.

◦ They are important components of erythrocyte membranes and determine the

differentiation of blood groups.

– Human blood groups are the determinants of A, B and O, sugar groups in some glycolipids.

◦ Cytolipin H: Sphingosine + Fatty Acid + Lactose

– Cytolipin H is a ceramide disaccharide with immunological effect.

◦ Cytolipin K: Sphingosine + Fatty Acid + Lactose + N-acetyl galactosamine

– Cytolipin K is a ceramide trisaccharide derived from the kidney, which is very similar to

the globoside substance found in the human erythrocyte.





Reference: Nelson ve Cox, 2012





Sphingolipids• Ganglioside

◦ Complex sphingolipids containing a large number of sugar unitslinked to ceramide.

◦ In addition to the hexose found in the cerebrosides, gangliosidescontain several more carbohydrates.

◦ The carbohydrate may be at least one mole of N-acetyl galactosamineor N-acetylglucosamine and at least 1 mole of N-acetylneuraminic acid(sialic acid).

◦ When hydrolyzed they give 1 mole sphingosine + 1 mole fatty acid+ 1 mole hexose + 1 mole N-acetyl galactosamine/glycosamine + 1 mole N-acetylneuraminic acid (NANA-sialic acid).

◦ Depending on the type and number of carbohydrates and/orcarbohydrate derivatives they contain (especially NANA), there aredifferent types of gangliosides.





Sphingolipids◦ They are found abundantly in the nerves and spleen.

◦ They are effective in the delivery of nerve impulse, taking part in the

construction of receptors (hormones) in cell membranes.

◦ They have functions in Cell-to-cell communication.

◦ They are located at the end of the nerve and bind to the

neurotransmitter molecules, acting as impulse chemical transmissions

in the passage of one nerve from one nerve.

◦ They are also related to carcinogenesis; cell growth and

differentiation. – Tumoral cells produce different type of gangliosides, thus cells can be

differentiated.





Sphingolipids• In addition to contributing to the structural integrity of the

membranes, glycosphingolipids are associated with many

cellular functions at the cell surface level.◦ They provide antigenic chemical markers for cells.

◦ They act as chemical markers that describe the various stages of cell

differentiation.

◦ They regulate the normal growth pattern of the cells.

◦ Cells are allowed to react with other bioactive substances such as

bacterial toxins (GM1 ligands), glycoprotein-forming hormones,

interferons, and viruses.





Sphingosine

Sphingosine Ceramide Sphingomyelin Sphingomyelin Cerebroside Ganglioside

PhosphacholinePhosphaethanolamin

One sugar residue Oligosaccharide residue

Sialic acid





Aliphatic Alcohols and WaxesAliphatic alcohols can be obtained in significant amounts

from many lipid sources. • The reason for this is that they are esterified with fatty acids.

Waxes are the simplest hydrolysable lipids. Waxes are

esters (RCOOR') formed from a fatty acid (RCOOH) and

a high molecular weight alcohol (R'OH).

The length of these acids and alcohols may be C16-C30.





The general formula of waxes is purely simple esters of

the general formula (R-CO-O-R).

Many plant and animal bodies are covered with wax

layers.

Wax layers prevent water from penetrating from one

side and from the other side. They are highly

hydrophobic molecules.

Both plants and animals bring natural waxes to the

field.

Aliphatic Alcohols and Waxes





Thay melt at wide temperature range (35-100°C) and

insoluble in water. They are very soluble in organic

solvents.

Most common alcohols found in waxes are Lauryl

alcohol, cetyl alcohol, seryl alcohol and myristyl

alcohol.

Most common fatty acids found in waxes are myristic

acid, palmitic acid, serotic acid and melissic acid.






Aliphatic Alcohols and WaxesWaxes are common in nature.

• They are found in the secretions of insects,

• They are found in the skin, hair and fur of animals as a protective layer

• They are found on the leaves of plants, fruits and shells.

Important Waxes;• Bee Wax (Beeswax – Cera alba) In the bee's secretion

• Carnauba Wax In plants

• Spermaceti Wax Whale

• Lanolin Wool





Beeswax• It is a mixture of ester which formed by palmitic acid and C26-

C34 fatty alcohols.• Beeswax, a complex mixture of over 200 different compounds,

contains the wax myricyl palmitate as its major component.• It melts at 62-65 ° C.• It is used in shoe polish, candle and wax paper making.

Carnauba Wax• Carnauba wax, a wax that coats the leaves of the Brazilian palm

tree, is used for hard, high-gloss finishes for floors, boats, and automobiles. Its main composition is ester myricyl cerotat.

• It melts at 80-87°C.• It is used to make duplicate paper (shoe polish, ground polish),

varnish, wax and waxy paper.






Whale Wax (Spermaceti wax)• Spermaceti wax isolated from the heads of sperm whales, is largely

cetyl palmitate, an ester; palmitic acid + cetyl alcohol• It melts at 42-45°C.• It is mostly used in ointments and cosmetics.

Lanolin (Wool wax)• It is a fatty acid ester of lanosterol. Contains free and esterified

cholesterol.• It forms a protective layer over the woolen fleece.• It has a very complex structure (long chain esters, hydroxy esters,

diesters, lanolin alcohols, and lanolin acids).• Lanolin has a very large amount of water retaining ability. For this

reason it is used for the preparation of ointments and various cosmetic products.






Aliphatic Alcohols and Waxes Places where waxes are used:

• Bee wax (beeswax) is used in honeycomb construction.

• Lanolin is used in the preparation of various ointments and creams, in the preparation of cosmetics.

• The oil layers on the hair, face and leaves are also composed of waxes.

• Spermaceti waxes are used in making candles.

• Carnauba wax is used in shoe polish, floor polish, varnish and candle making.

• The planktons in the seas also store significant amounts of waxesand use them as an energy source.

• The waxes secreted from the gland found in the tail parts of some birds indicate that the fur does not get wet from the water.





Terpenes are lipids composed of repeating five-carbon

units called isoprene units. An isoprene unit has five

carbons: four in a row, with a one-carbon branch on a

middle carbon.• There are double bonds in the molecule and these bonds are

conjugated.◦ Thus, they have high reaction ability.

• The polymerization of molecules of the same material with one

another is called polymerization.

• The isoprene molecules must dehydrate before being polymerized.

• When the dehydrated 5 C isoprene molecules are polymerized,

compounds called terpenes form.

Terpenes





(C5H8)n

Isoprene Unit Isoprene Unit





Most terpenes are hydrocarbons, others are alcohol,

ether, aldehyde, ketone and acid.

Many terpenes smell good.

It can be separated from other herbal substances by

lightly heating and by distillation.

Some of the terpenes are used in perfumes, sweeteners

and in medicine.

Lycopene, Carotene, Vitamin A and Squalene are some

of the most important biological terpenes.

Terpenes





The most important group of terpenes is carotenoids(tetraterpenoids).• They are in different colors; ranging from light yellow to red violet.

• Some of them are acyclic, that is, they have no ring, they have a chain structure, and some have hydroaromatic rings on both ends of the chain.

Carotinoids carrying hydroaromatic rings are called carotenes (carotins).• Carotenoids are substances that give yellow color to many natural

oils.

Because of carrying double bonds, they easily and rapidly oxidized by oxygen and ultraviolet rays.

Terpenes





Terpenes Carotinoids in aliphatic form

• Lycopene: It is tetraterpene assembled from eight isoprene unitsand is insoluble in water. It is a bright red carotenoid pigment found in tomatoes and other red fruits.

• Squalene: It is triterpene assembled from six isoprene units. All plants and animals produce squalene as a biochemical intermediate. It is a natural and vital part of the synthesis of all plant and animal sterols, including cholesterol, steroid hormones, and vitamin D in the human body.

Carotinoids with Alcohol group in Aliphatic Structure• Phytol: Phytol is an acyclic diterpene alcohol that can be used as a

precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. It consist of 4 isoprene units. It is a constituent of chlorophyll.





Terpenes Carotinoids in the aliphatic structure with a carboxyl

group• α-Crocetin: It consists of 4 isoprene units. There are two carboxyl

groups at each end of the chain. It is the substance that gives the yellow color of bile.

Carotinoids with hydroaromatic rings• The substances in the building are called as carotenes. The

hydroaromatic rings are located at both ends of the four isopreneunits.

• Hydroaromatic rings are called ionone rings and there are threetype; α-ionone, β-ionone and pseudoionone rings.◦ α-ionone and β-ionone rings are closed and carry one single bond. The place

of C=C is different.◦ The pseudoionone ring is open and two double bonds are carried.◦ There are 3 types of carotene in the nature. α-, β- and γ-carotene.





α-Ionone Ring β-Ionone Ring Pseudoionone Ring





Terpenes Carotinoids with hydroaromatic rings, Carotenes;

• α-Carotene: It consists of α-ionone + 4 isoprene unit + β-iononering. It is a precursor (inactive form) to one mole vitamin A.

• β-Carotene: It consists of β-ionone + 4 isoprene unit + β-iononering. It is a precursor (inactive form) to two mole vitamin A.

• γ-carotene: β-ionone + 4 isoprene unit + pseudoionone ring. It is a precursor (inactive form) to one mole vitamin A.

Carotenes are found especially in green plants. The yellow and orange colored fruits are rich in β-carotene, such as carrot, mangoes, pumpkin and papayas.





Isoprene Unit Isoprene Unit

β-Carotene

β-Ionone

Ring

β-Ionone

Ring





Interconversion of Retinoids

β-Carotene

Retinal

(Vitamin A1)

11-cis-Retinal

Retinol

(Vitamin A)

Retinoic Acid

(Retin A)

Retinal

isomerase

Retinal

reductase





Carotinoids with an alcohol group in hydroaromatic

structure• Xanthophylls: It is a Dihydroxy α-carotene.

◦ Both ionone rings carry hydroxyl groups.

◦ Gives color to chicken fat, egg yolk and chicks' feathers.

• Cryptoxanthin: One of the ionon rings has OH group. It is a

monohydroxy β-carotene.◦ It is found in corn grains and red pepper.

◦ Since it has β-ionic ring, 1 molecule Vitamin A can be synthesized.

Terpenes





They are very common in animals and plants.

Since they have a lot of physiological activities, they are always remarkable compounds.

All steroids always carry the sterane ring (cyclopentanoperhydrophenanthrene ring).

The numbering and lettering of the steran ring is very important. Because these carbons come in and out of groups and different type steroids occurs.

Steroids





Sterane ring(cyclopentanoperhydrophenanthrene ring)

A B

C D

• The phenanthrene ring consists of 3

benzene rings.

• If this ring is saturated with

hydrogen, the double bond opens

and the perhydrofenanthrene ring

occurs.

• If a cyclopentane ring is added to

the perhydrofenanthrene ring,

cyclopentanoperhydrophenanthrene

(sterane) ring is formed.





In the formation of different steroids, the side chain

attached to 17th C atom is mostly changed.• New steroids are formed by changing the side chain.

• Steroids are derivatives of the sterane ring which carry some

functional groups such as carbon side chain, alcohol, aldehyde,

ketone and double bond.

Biologically important molekules that carry the

sterane ring are;

Steroids

• Sterols

• Bile acids

• Sex hormones

• Adrenal cortex hormones

• Vitamin D group substances





Sterols

• They carry a sterane ring and a side chain. All sterols

contain an alcoholic hydroxyl group in the 3rd

carbon atoms. There are 3 subgroups.

1. Zoosterols

2. Mycosterols

3. Phytosterols

Steroids





1. Zoosterols• It is found only in animal tissues and the most important

member is cholesterol.

• Cholesterol is found in all animal tissues, in the membranes of many animal cells, in the lipoproteins of blood plasma, and is synthesized in the liver.◦ It is found mostly in the brain, nervous tissue, adrenal glands and

egg yolk.

• They are not found in plants.

• It has an antihemolytic effect. Because of this property, it is effective against hemolytic effects of bacterial toxins, snake venom, bile salts and other hemolytic substances.

Steroids





Cholesterol Sterane ring in cholesterol;

• 1 mole OH group on the 3rd

carbon atom,

• A double bond between

carbons 5 and 6,

• Methyl groups on 10th and

13th carbon atoms,

• Carbon 17 carries a side

chain of 8 carbons.





• Properties of cholesterol;◦ It is found only in animal tissues, not in plants.

◦ It is tasteless and odorless.

◦ Oxidized if exposed to air and light.

◦ When oxidized, 7-hydrocholesterol is formed, which is the precursor

of Vitamin D3.

◦ It is the precursor of the adrenal cortex hormones, the sex hormones,

and the precursor of cholic acid (one of the bile acids).

• Cholesterol is present in tissues in two ways; Free Cholesterol

and Ester Cholesterol.

• The amount of cholesterol in the tissues is in wide range.

Steroids





• The dried form of brain white matter contains 14% cholesterol.

• Cholesterol has an important role in the lipid metabolism, the

transport of lipids.

• It is the precursor in the synthesis of bile acids, sexual

hormones and other steroids.

• In lipid metabolism disorders and aging, cholesterol fatty acid

esters are deposited in the vascular walls and adhere to the

arteries.

• It is accepted that 90% of the existing cholesterol in the body

is used in the synthesis of bile acids and 10% in steroid

hormones.

Steroids





• The chemical properties of cholesterol come from the group of

seconder alcohols and the double bond they carry. They can

esterify with fatty acids at the 3rd C atom which carries OH

group. These esters are common in blood and tissues.◦ Again, this hydroxyl group is ketonized with oxidants, such as

cholestenone.

• Another molecule of Zoosterols is the abundant amount of

lanosterol in the sheep wool.◦ Lanosterol is similar in structure to cholesterol. There is a double

bond in the side chain. Carbon-4 has two molecules of methyl groups.

There are not double bond between 5-6 Cs but there are double bond

between 8-9 Cs.

Steroids





2. Mycosterols• They are sterols found in yeast and fungi.

• The most important member is the ergosterol. It turns into ergocalciferol under UV light. This is Vitamin D2.

• Ergocalciferol is not found in animal tissue, but it is indicated that it can be used instead of cholecalciferol.

3. Phytosterols• They are vegetable sterols and there are two important

members. Stigmasterol and sitosterol. Stigmasterol is the procursor of progesterone. Sitosterol is especially abundant in grain grains.

Steroids





Bile Acids• Bile acids are the substances that carry the Sterane ring. They

contan 24 Carbon atoms.

• It is synthesized by humans and animals using cholesterol as a

precursor. ◦ Research has shown that 85% of the body's injected cholesterol is

turned into bile acids by the liver.

• The last three carbon atoms in the side chain of cholesterol

are broken down by oxidation and the carboxyl group forms

and the bile acids occur.

• Bile acids are mainly synthesized by the liver.

Steroids





• Bile acids are oxy derivatives of cholanic acid.◦ Cholic Acid ---------------------------3,7,12-Trihydroxycholanic Acid

◦ Deoxycholic Acid -----------------------3,12-dihydroxycholanic Acid

◦ Lithocholic Acid --------------------------------3-Hydroxycolanic Acid

◦ Hyodeoxycholic acid----------------------3,6-dihydroxycolanic Acid

◦ Chenodeoxycholic Acid ----------------3,7-Dihydroxycholanic Acid

• The most commonly found bile acids are cholic acid and

chenodeoxycholic acid.

• Bile acids are not free. They are all conjugated. It is called

conjugated bile acids and is coupled with glycine and taurine

via carboxyl groups.

Steroids





• Main properties and functions of bile acids◦ It has emulsifying properties to reduce surface tension.

◦ They play an important role in the absorption of fatty acids from the

small intestine.

◦ By reducing surface tension, enzymes such as lipase can make better

effect on lipids.

◦ Because of these properties, salts of bile acids facilitate absorption of

water-insoluble cholesterol, fats, fat soluble vitamins and

phosphatides.

◦ About 5-10 grams of bile passes into the intestines.

◦ A portion of the biles found in bowel is absorbed and transfered to the

liver via vena porta and then passes through the intestines again. This

is called enterohepatic circulation.

Steroids





Lipoproteins, Eicosanoids, Lysophosphoglycerides, Lipopolysaccharides

Lipids linked to other

class compounds





Lipoproteins play an important role in the transport of

phospholipids, cholesterol and triglycerides in the

plasma.

Some lipids combine with specific proteins to form

lipoproteins.

Blood plasma lipoproteins are classified according to the

particles of lipids and their concentrations which they

contain.

There are mainly 4 groups (+1 intermediate)

lipoprotein, which contain 50-90% lipid.

Lipoproteins





Chylomicrons (CM): Triacylglycerols are carried to the tissues.

Very Low Density Lipoproteins (VLDL): They contain

triacylglycerols synthesized in the liver.

Intermediate Density Lipoproteins (IDL): Intermediate

lipoproteins.

Low Density Lipoproteins (LDL): They allow the transport of

cholesterol from liver to tissues , and the lipoprotein that

contains the most cholesterol in the body.

High Density Lipoproteins (HDL): Proteins and phospholipids are

present in excess in the structure. It allows cholesterol to be

transported from the various tissues to the liver.

Lipoproteins





Source: Engelgink, 2014





LipoproteinsThe proteins involved in the structure of lipoproteins

are called apolipoproteins or apoproteins.

These are classified as Apo-A, Apo-B, Apo-C and Apo-E.

They have also sub-fractions.

The protein components of lipoproteins organize the

entry and exit of particulate lipids into specific locations.





Lipoprotein Structure

Source: Engelgink, 2014 Source: Uni.Wisconsin





http://www4.uwsp.edu/chemistry/tzamis/ch260/lipoprotein.jpg

Eicosanoids Eicosanoids, are a group of biologically active

molecules which derived from arachidonic acid (20C atom).

They are molecules that are found in very low concentrations in the cell, yet have very strong effects.

Prostanoids (Prostaglandins, Thromboxanes,Prostacylcins), Leukotrienes and Lipoxins are examples.





EicosanoidsThey have a similar effect to hormones. But like

hormones, they are not synthesized and sent to the

target tissues via blood.

Depending on the external stimuli, they are synthesized

as needed and act on the tissues they synthesize.

They are not stored in the cell.

Eicosanoids are effective in events such as

reproduction, inflammatory events, wound, fever,

induction of blood clotting, and regulation of blood

pressure.





Prostaglandins (PG)• They are a subclass of eicosanoids and of the prostanoid

class of fatty acid derivatives.

• Prostaglandins have types such as PGA with acid character, PGB with basic character, PGE extracted with ether, PGF extracted with phosphate buffer. Subtypes of each type are also defined.◦ The capital letters A, B, D, E, F, G, H, I in the prostaglandin symbol

indicate the ring type of the molecule.

◦ The small letter in the prostaglandin symbol after the capital letter and written in alta shows the number of unsaturated bonds in the molecule.

◦ For the F series, the α Greek letter is used to indicate the state of the -OH group at C9.

Eicosanoids





• Prostaglandins mediate autocrine and paracrine regulatory

functions.

• Prostaglandins have numerous functions. Some of them give

the impression of the opposite of each other.

• Prostaglandins affect a wide range of cell and tissue functions.

Different types of prostaglandin types on a cell, tissue or

system may have different effects; Gastrointestinal, Pain,

Fire, Vascular, Respiration, Reproduction.◦ PGF2α is released by stimulation of the uterine oxytocin, causing the

corpus luteum to lyse.

◦ PGF2α and PGD2 act as constructors in the smooth muscles of the

trachea and bronchi, while PGE2 and PGI2 act as relaxants.

Eicosanoids





Prostacyclins (PGI2)• Prostacyclin is the primary prostaglandin synthesized by vascular

endothelium.

• Prostasicline is a vasodilator. The vein relaxes the smooth muscle.

• Prostasicline prevents platelet aggregation and adhesion to the endothelium surface.

Thromboxans• It is an eicosanoid associated with the prostaglandins, containing an

ether group in the six-membered ring.

• Thromboxanes consist of arachidonic acid in platelets; are effective in the formation of blood clots and in reducing blood flow instead of clot.

Eicosanoids





Leukotrienes• They are eicosanoids that contaion three conjugated double

bonds and not a ring structure in molecular structures.

• Leukotrienes can cause contractions in the muscles of the

airways of the lungs, resulting in asthma attack; The cysteinyl

types of leukotrienes are known as the slow-reacting substance

of anaphylaxis (SRS-A).

• Leukotrienes cause local vasodilatation, increase permeability

of the capillaries, enhance the effects of chemical mediators

and ultimately cause pain and discomfort. In other words, they

facilitate chemotaxis, inflammation and allergic reactions.

Eicosanoids





• There are four types1. Cysteinyl Leukotrienes (LTC4, LTD4, LTE4, LTF4)

2. LTB4

3. LTG4

4. LTB5

• LTC4 and LTD4 cause smooth muscle contraction and are 1000

times more effective than histamine in narrowing the lung

airways.

• At the same time, they increase fluid infiltration from small

blood vessels and constrict coronary arteries.

• LTB4 attracts neutrophils and eosinophils instead of

inflammation.

Eicosanoids





Lipoxins (LX)• Lipoxins are trihydroxy derivatives of arachidonic acid .

• Two types have been identified; Lipoxin A4 (LXA4) and B4

(LXB4).

• Although lipoxins are synthesized in very small quantities, they

are powerful inflammatory mediators and play an important

role in the resolution of inflammation.◦ By inhibiting infiltration of the polymorphonuclear leukocyte (PMN)

into the inflammatory zone, vasculary permeabilisation returns to

normal levels. It enhances non-inflammatory migration of

mononuclear cells and accelerates resolution by allowing apoptotic

PMNs to accumulate in macrophages.

Eicosanoids





Lisophosphoglycerides• They are found in the membrane and the cell. They occur by

the hydrolytic removal of one of the two fatty acids of the

glycerophospholipids. They serve as intermediate metabolites.

Lipopolysaccharides• They are found on the outer membranes of Gram-negative

bacteria. It is the main building component.

• Also known as lipoglycans and endotoxins.

• In animals,they cause strong immun reactions.

Others





Görsel Kaynak: WikiMedia





https://commons.wikimedia.org/wiki/File:Cell_membrane_detailed_diagram_en.svg



Altınışık M. Ders Notları. İnternet Erişim:

http://www.mustafaaltinisik.org.uk/89-1-08.pdf

Ası. T. 1999. Tablolarla Biyokimya, Cilt 1

Engelking LR. 2014. Textbook of Veterinary Physiological Chemistry. 3rd

edn. Academic Press.

Fidancı UR. Ders Notları. İnternet Erişim:

http://80.251.40.59/veterinary.ankara.edu.tr/fidanci/

King M. İnterner Erişim: http://themedicalbiochemistrypage.org/#nogo

Smith JG (2010). Organic Chemistry, 3rd Edition, McGraw-Hill.

Smith JG (2012). General, Organic, & Biological Chemistry 2nd Edition,

McGraw-Hill.

Sözbilir Bayşu N, Bayşu N. 2008. Biyokimya. Güneş Tıp Kitapevleri, Ankara

References





http://www.mustafaaltinisik.org.uk/89-1-08.pdf

http://80.251.40.59/veterinary.ankara.edu.tr/fidanci/

http://themedicalbiochemistrypage.org/#nogo

Question 1

Answer: a

1. ................ are monocarboxylic organic acids with

hydrocarbon chains.

a. Fatty acids

b. Terpenes

c. Bile acids

d. Hydrocloric Acid

e. Phosphoric Acid





Question 2

Answer: c

2. Which of the following is an essential fatty acid?

a. Palmitic Acid

b. Stearic Acid

c. Linoleic Acid

d. Lignoceric Acid

e. Myristic Acid





Question 3

Answer: d

3. Which of the following terpenes is the precursor of

Vitamin A?

a. Xanthophyll

b. Cryptoxanthin

c. α-crocetin

d. β-carotene

e. Lycopene





Your questions?





Next title;

Amino Acids, Peptides

and Proteins





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