lipid update

7/29/2019 Lipid Update

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By :drg. Prasetyo Adi, MS


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OBJECTIVES :

Students can understand :

1. Classification of lipids

2. The importance and source of lipids

3. Chemical and physical properties of lipids


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LIPIDS ???

Large molecules made up of elements -Carbon, Hydrogen, Oxygen

relatively insoluble in water, but soluble in

nonpolar solvents such as ether, aceton,benzene, chloroform and carbon tetrachloride (CCl4)

Non volatile, odorless, tasteless, butwhen its allowed to stand out in the open

air for a long time rancid


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LIPIDS FUNCTIONS

Energy storage

Constituent of membrane structure

Hormone synthesis

Thermal insulator

Electrical insulatormyelin sheath

The solvent of fat-soluble vitamins


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Basic structure

Fats are esters made up of an alcohol part and an acid part

In fats the alcohol part is always glycerol

The acid part of fats :

straight-chain carboxylic acids

have an even number of carbon atoms

R C OR

O

Acid part Alcohol part


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Basic structure :

Fatty acids

H2C

CH

H2C O

O

O C

C

C

O

O

O

R3

R2

R1

Triglyceride (triacylglycerol)


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RLipids : Alkyl and Carboxyl groups

Alkyl is a hydrophobic group, which insolublein water a non polar part

Carboxyl is a hydrophilic group, water soluble a polar part

Hydrophobicity ofR groups depend on :

number of carbon atoms, branched or not,have double bonds or not


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Fatty Acids

Long chain hydrocarbons with one carboxyl groupat the end of chain, which may be saturated orunsaturated

Types of Fatty acids :Saturated FA : no double bond

Unsaturated FA : one or more double bonds


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Saturated FA based on the length of thestraight chain of C, with the number of carbonatoms are odd or even, and there are branched ornot.

A. The C straight chain with an even number of C atoms :

Butyric ac, Kaproic ac, Kaprylic ac, Lauric ac, Myristic ac,Palmytic ac and Stearic ac.

B. The C straight chain with an odd number of C atoms :

Pentadecanoic ac, Heptadecanoic ac, Valeric ac,Heptanoic ac, Nonanoic ac

C. The C branched chain of fatty acids :

COOH

COOH

As.Pristanat

As.Phitanat


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Systematic names of unsaturated fatty acids

Based on the position and number of double

bonds

1. D numbering system :

The terminal carboxyl carbon is designated

carbon 1, and the double bond is given the number

of C atom on the carboxyl side of the double bond.

Dp n : y p= position of double bond from terminalcarboxyl group

n= number of C atoms

y= number of double bonds

2.w

numbering system :The terminal methyl carbon is designated

carbon 1, and the double bond is given the number

of C atom on the carboxyl side of the double bond.

wp,Cn : y p= position of double bond from

terminal methyl group


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3 : linolenic acid :

CH3-CH2-(CH=CH-CH2)3-(CH2)6-COOH

6 :

1. Linoleic acid :

CH3-(CH2)4-(CH=CH-CH2)2-(CH2)6-COOH

2. Linolenic acid :

-(CH=CH-CH2)3(CH2)3COOH

3. Arachidonic acid :

-(CH=CH-CH2)4(CH2)2COOH


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Chemical properties of fatty acids

C C IBr C C

i

-

Br-

C C

Br

I

+

2HC C

H

C

H H

C

H

C

H

B-

2HC HC C

H

C

H

C

H2H+

Carboxyl groups methylation

Addition of halogen (unsaturated FA)

Double bond transformation


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Oxydation

3. Aldehyde group determines for rancidity

1. When fats and oils are allowed to standout in the open oxidation by the airand turn some molecules intoaldehydes rancid, with bad tastesand odors2. Because of microorganism occurence,oxydation reaction do faster at roomtemperature


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Hydrolysis

1. Hydrolysis of triglycerides

shortchain fatty acids which have badodor.

2. To prevent oxydation and hydrolysisreaction of fats by giving anantioxidant or another compounds.


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Hydrogenation

Double bonds can be reduced to single bonds bytreatment with hydrogen (H2) and a catalyst.

Iodine Number Test

A test for degree of unsaturated in fats and oils The test consists of adding a halogen to a sample

The iodine number is defined as the number of grams ofiodine that adds to 100 grams of samples

-- C = C -- + I2 -- C CI I I I

I II I


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Lauric Miristic Palmi

tic

Stea

ric

Oleic Linole

ic

Linole

nic

Othe

r

Iodine

number

Animal Fat

Beef tallowButter

Lard

Human

Vegetable OilCoconut

Corn

CottonseedLinseed

Olive

Palm

Peanut

Safflower

SoybeanSunflower

--2,5

--

45,5--

----

--

--

--

0,2--

6,311,1

1,3

2,7

181,4

1,4--

--

1,4

--

6,8

0,1

--

27,42928,324

10,5

10,2

23,46,3

6,9

40,18,3

9,5

5,6

14,19,2

11,9

8,4

2,3

3

1,12,5

2,3

5,5

3,1

2,42,2

49,626,747,546,9

7,5

49,6

22,919

84,4

42,7

5618,6

28,925,1

2,53,6

6,0

10,2

--

34.3

47,824,1

4,6

10,3

26,070,1

52,366,2

----

--

--

--

--

--47,4

--

--

--

3,4

3,6--

0,117,95,0

7,8

16,31,5

3,40,7

1,8

--

6,6

1,1

2,7--

5036

59

68

10

123

10617981

54

93

145

130126


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Physical properties of fats

Fats that come from animals are generally solids

at room temperature

Fats that come from plants or fish are usually

liquids at room temperature oils The structural difference :

- Solid fats contain mainly saturated FA- Liquid fats unsaturated FA

T i l Gl l (TG)


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Triacyl Glycerol (TG)

Glycerol is an alcohol compound with threehydroxyl groups can form esters with 1,2or 3 of same or different fatty acids

, , and configuration at crystallic formgives properties of different melting point.The most stabil configuration is .


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Classifications

1. Simple lipids :

- Fats

- Waxes

2. Complex lipids :

- Phospholipids

- Glycolipids (glycosphingolipids)- Other complex lipids :fosfolipids, aminolipids,lipoproteins

3. Precursors and derived lipids :

- fatty acids- glycerol

- steroids

- keton bodies

1 Si le li id


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1. Simple lipids:= Esters of fatty acids with various alcohols.

- Fats: Esters of fatty acids with glycerol.

Oils are fats in the liquid state.

- Waxes: Esters of fatty acids with higher molecular weightmonohydric alcohols.

2. Complex lipids :

= Esters of fatty acids containing groups in addition to an alcohol

and a fatty acid.

- Phospholipids: Lipids containing, in addition to fatty acids and an

alcohol, a phosphoric acid residue.

glycerophospholipids the alcohol is glycerolsphingophospholipids the alcohol is sphingosine.

- Glycolipids (glycosphingolipids) : Lipids containing a fatty acid,

sphingosine, and carbohydrate.


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3. Derived lipids.

= Lipids derived from simple lipids and complex lipids

These include : fatty acids, glycerol, steroids, otheralcohols, fatty aldehydes, ketone bodies, hydrocarbons,lipid-soluble vitamins, and hormones.


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COMPLEX LIPIDS :

1. Phospholipid contain : A. An Alcohol

B. Fatty acids

C. A Phosphate group

A. PHOSPHOGLYCERIDES

= Triesters of glycerol-3-phosphate in which

Two ofOH groups are esterified by fatty acids, the 3rd

OH group is esterified by phosphate group, which is also

connected to another alcohol.

2 Types of Phospholipids :


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H2C

HC

H2C

O

O

O

C

C

P

O

(CH2)16O

(CH2)7

CH3

C

H

C

H

C

H2

C

H

C

H

(CH2)4 CH3O

O

O

CH2C N(CH3)3+

-

LESITIN

Classification of phosphoglycerides :

1. Phosphatidylcholine (lechitin)

2. Phosphatidyletanolamine (cephalin)3. Phosphatidylserine (cephalin)4. Phosphatidylinositol5. Cardiolipin


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B. Sphingolipids

Present in nearly all human tissues, which the greatestconcentration is in CNSwhite matter, the coating of nerve axon(myelin)

All sphingolipids are derived from sphingosine

H3C(H2C)12HC

HC

HC

HC

OH

CH2

OHNH2Sphingosin


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H2C C

H

C

H

H

C

H

C

OH

C

H2

NH

C O

R

O P

O

O

OCH2CH2 N(NH3)3CH312

-

+

Sphingomyelin

2. GLYCOLIPIDS

= Complex lipids that contain carbohydrate

Among the glycolipids are cerebrosides, which areceramide mono-or oligosaccharide.

STEROIDS


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STEROIDS

= compound containg this ring system :

3 cyclohexane rings (A,B,C ) connected inthe same way as in phenanthrene, andafused cyclopentane ring.

1 cyclopentane

(D)

A B

C D1

2

3

4

5

10

6

7

8

9

11

12

13

1415

16

17

STEROID

CHOLESTEROL


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CHOLESTEROL.

- The most abundant steroid in human body

-Serve as membrane component (plasma membrane oferythrocyte and in the myelinated nerve cells)

- Serve as raw materials for other steroids (the sex andadrenocorticoid hormones)

A B

C D

CH3

H3C CH3

CH3

CH3

HO

KHOLESTEROL


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Cholesterol

Exists both in the free form and esterified with

fatty acids Free cholesterol gall stone Cholesterol in the body is in a dynamic state

the serum cholesterol level controls the amount

of cholesterol synthesized by liver

Cholesterol is transported from the liver to the

periferal tissues by lipoproteins (HDL, LDL, VLDL)

High serum cholesterol level associates with suchdiseases as atherosclerosis

STEROID HORMONES


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STEROID HORMONES

Synthesized from cholesterol :

The aliphatic side chain on the D ring is shortened bythe removal of a six-carbon unit, and the secondaryalcohol group on C-3 is oxidized to a ketone

PROGESTERONE

The starting compound

ADRENOCORTICODHORMONES

SEXHORMONES

ADRENALGLANDS

MINERALOCORTICOIDS GLUCOCORTICODS


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H3C CH3CH2OHKHOLESTEROL


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A

CH3

HO

C

B

D

CH3CH3

A

CH3

O

C

CH3

C O

CH3

B

D

A

CH3

O

CH3

C O

HOOH

C

B

D

A

CH3

O

C

CH3

OH

B

D

A

CH3

O

CH3

C O

CH2OH

OOH

C

B

D

KORTISON

HO

CH3

OH

B

C D

A

A

CH3

O

CHC O

CH2OH

HO

O

C

B

D

ALDOSTERON

PROGESTERON

KORTISOL

TESTOSTERON

ESTRADIOL


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Soaps


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Soaps

Soaps are produced from triglyceride

hydrolysis in an alkaline medium

Soaps clean because each soap moleculehas a hydrophilic head (-COO-) and a

hydrophobic tail ( a long chain alkaline-likeportion).

The hydrophilic head dissolevs in thewater, the hydrophobic end dissolves in the

dirt cause an emulsifying action


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The function :1. To separate cells from external

environment

2. To provide selective transport fornutrients and waste products

MEMBRANES


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EICOSANOIDS


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EICOSANOIDS

Products of the metabolism of the 20-carbon-

polyunsaturated fatty acid arachidonic acid 3 groups :

1. Prostaglandins

2. Thromboxanes3. Leukotrienes


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Reading tasks :

The Myelin sheath and MultipleSclerosis

Prostaglandins, thromboxanes, andLeukotriens

Atherosclerosis

Gall stone

THANKS FOR YOUR


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