In the name of Gad. عناوین مطالب 1- اهمیت لیپیدها 2- طبقه بندی لیپیدها 3- اسیدهای چرب 4- اسیدهای چرب غیر اشباع 5-

In the name of Gad

مطالب عناوین1- لیپیدها اهمیت

لیپیدها -2 بندی طبقه3- چرب اسیدهای

اشباع -4 غیر چرب اسیدهای5- سیس و ترانس چرب اسیدهای

6- چرب اسیدهای انواع7- چرب اسیدهای خواص

الکلها-89- گلیسرولها آسیل تری

گلیسرول -10 آسیل فسفووپالسمالوژن -11 لیپین کاردیو

فسفولیپازها-12

13- ،مومها ترپنهااسفنگولیپیدها-14

استروئیدها-15سلولی -16 غشاءها

ها -17 پروستاگالندین18- ها پروتئین لیپو

Lipids آلی حاللهای در بیشتر و دارند آب در کمتری حاللیت لیپیدها

. میشوند .. حل بنزن اتر، مانند حل( قطبی دو مولکولهای .amphipathicلیپیدها هستند( . شوند می محسوب سلولی غشاهای اصلی جزئ لیپیدها. شوند می محسوب انرژی از غنی مبنع گرم .....1 لیپیدها

Kcal 9 چربی در محلول ویتامینهای انتقال در D, A, E, Kِ (Vit)لیپیدهالیپیدها . دارند سرما برابر در حفاظتی نقش امواج انتقال به درکمک عصبی سلولهای غشائ در لیپیدها

. دارند نقش عصبی

Formation of an ester:

O O

R'OH + HO-C-R" R'-O-C-R'' + H2O

اسید چربیالکل

Classification of Lipids:

Lipids are classified into Three great classes: Those that only contain fatty acids + ROH = (simple lipids);-Lipids : fatty acids + Glycerol =TG- Waxes : fatty acids+ Long alcole Those that contain fatty acids + ROH+ another Substance

(complex lipids).- phospholipids-Glycolipids -Lipoprotien-Sphingolipids Steroids

Fatty AcidsFatty acids = carboxyl group + a long hydrocarbon chain

Saturated fatty acids are single bonds in all carbon-carbon bonds;Unstaurated fatty acids contain one or more double bonds in

hydrocarbon chains;Fatty acids can be named in three ways. See above figure and

table 6.1- Number of carbon + Enoic انوئیک-Number of carbon + Anoicآنوئیک

CCH2

H2C

CH2

H2C

CH

H2C

CH2

H2C

CH2

H2C

CH2

H2C

O

HO

CH2

H2C

CH3

16:0 =Palmitic Acid=Hexadecanoic acid

O

OH O

OH

18:1 =Oleic acid=9-Octadecenoic acid

9

18:1 اولئیک اسید ω 9

Classification of FA:

Saturated FA Unsaturated FACarboxyl

group

Hyrocarbon group

Saturated chains pack tightly and form more rigid, organized aggregates (i.e., membranes(;

Unsaturated chains bend and pack in a less ordered way, with greater potential for motion.

Trans & Cis form of USFA

cis form of oleic acid

trans form of oleic acid

چشم شبکیه سلولهای غشائ

W9,

w6

w3

w9

w6

Common Fatty Acids

Saturated fatty acids:

Unsaturated fatty acids: Octadecadienoic acid

Octadecatrienoic acid

Eicosatetraenoic acid

Structural Consequences of Unsaturation

Other Fatty Acids:Cyclic fatty acid

آراشیدیک آسید پروستانوئیک اسید

است حلقوی چرب اسید شولمگریک .اسیداست دار شاخه چرب اسید فیتانیک . اسید

Properties of Fatty Acids: Melting Point -SFA number of carbon ..... MP-USFA number of double bound …. MP

Saponification Number of COOH Number of saponification

(mg KOH ……1gr FAT)

بوتیریک کربنه 4اسیدلیگنوسریک کربنه 24اسید

Properties of Fatty Acids: Hydrogenation

USFA + H2 SFA Binding with O2 O2 + USFA -Epoxide ((اپوکسید-ketoHydroxide( هیدروکسید (کتو-En –Diol (اندیول)-Proxide(پرواکسید) Binding With I2

I2 + USFA ( ( یدی عدد Indies of iodine…..(gr of I2 ….100 gr fat)یا

Alcohols : 1-Glycerol

C holestero l

H O

3-Estrols

2-Sphingosine

H2CHC

OH

CH

N+ CH

C

CH2

CH3

H

H3

OH

( )12

sphingosine

OH

Formation of an ester:

O O

R'OH + HO-C-R" R'-O-C-R'' + H2O

اسید چربیالکل

فنانترن پنتانو سیکلو حلقه

Triglycerols (triglycerides) Triglycerols consist of a glycerol esterified with three

fatty acids If all fatty acid chains are the same, the molecule is

called triacylglycerol (e.g., tristearin)

Lecture 15. Lipids 13Lecture 15. Lipids 13

•TG is most important ofStorage lipids in fat tissueAnd non polar.

Phosphoacylglycerols

a polar head group (X): serine, choline, ethanolamine, glycerol, or inositol.

Hydrogen

Ethanolamine

Choline

Serine

Inositol

Phosphatidic acid

Phosphatidylethanolamine

Phosphatidylcholine

Phosphatidylserine

Phosphatidylinositol

x

Cardiolipin & Plasmalogen

دی فسفاتيدل گليسرول

پالسمالوژن=آلدئید چرب+مونوآسیل گلیسرول پیوند وینیل اتر

کارديولیپین=فسفاتیدات +فسفاتیدات+گلیسرول

Phospholipases

B

Waxes Waxes are esters of long-chain alcohols with long-chain

fatty acids; Waxes are water-insoluble due to the weakly polar nature of the ester group.

Lecture 15. Lipids 18Lecture 15. Lipids 18

با چرب اسید استرهستند بلند زنجیره با الکلهای

Terpenes Terpenes are a class of lipids from two or

more molecules of 2-methyl-1,2-butadiene, or isoprene;

Example of a terpene molecule:

All sterols (including cholesterol) and steroid hormones are terpene-based molecules

Lecture 15. Lipids 19Lecture 15. Lipids 19

CHO

all-trans-retinal

The amino group of sphingosine can form an amide bond with a fatty acid carboxyl, to yield a ceramide.

Ceramides usually include a polar head group,

H2CHC

OH

CH

N+ CH

C

CH2

CH3

H

H3

OH

( )12

sphingosine

H2CHC

OH

CH

NH CH

C

CH2

CH3

H

OH

( )12

C

R

O

ceramide

Sphingolipids are derivatives of the lipid sphingosine, which has a long hydrocarbon tail, and a polar domain that includes an

amino group.

R-OH +

Sphingolipids:

Sphingomyelins

H2CHC

O

CH

NH CH

C

CH2

CH3

H

OH

( )12

C

R

O

PO O

O

H2C

H2CN+

CH3

H3C

CH3

Sphingomyelin

phosphocholine

sphingosine

fatty acid

FA + Spingosine ceramide ((سرامید

Ceramide + phosphocholine Sphingomyelin(اسفنگومیلین)

H2CHC

OH

CH

NH CH

C

CH2

CH3

H

OH

( )12

C

R

O

ceramide

cerebroside with -galactose head group

H2CHC CH

NH CH

C

CH2

CH3

OH

C

R

O

OH O

H H

H

OHH

OH

CH2OH

HO

H

( )12

Ceramide + monosaccharide

Cerebrosides(سربروزید(Ceramide + monosaccharide + sialic acid Gangliosides(GM((گانگلیوزید(

Ceramide + monosaccharide +sulfate Sulfatides (سولفاتید)

Sphingoglycolipids

Hydrogen

Phosphocholine

Glucose

Oligosaccharide

Ceramide

Sphingomyelin

glucosylcerebroside

Gangliosides

Cholesterol is largely hydrophobic.

But it has one polar group, a hydroxyl, making it amphipathic.

C holestero lH O

Cholesterol, an important constituent of cell membranes, has a rigid ring system and a short branched hydrocarbon tail.

Steroid:

Cholesterol

inserts into bilayer membranes with its OH oriented toward the aqueous phase & its hydrophobic ring system adjacent to fatty acid chains of phospholipids. The hydroxyl group of cholesterol forms hydrogen bonds with polar phospholipid head groups.However interaction with the relatively rigid cholesterol decreases the mobility of hydrocarbon tails of phospholipids.

Steroid:

Phospholipid

Membrane Phospholipids

Example of steroids

کولیک اسیدکولیک کنوداکسی اسید

Prostaglandins:

:TXرگها صاف عظله انقباض

پالکتی تجمع

Prostaglandins inhibitors

indomethacin ibuprofen

Dexamethasone

دهند - می افزایش را پالکتی تجمع- غشائ از یونها عبور تنظیم

التهاب-- وعضله کلسیم متابولیسم تنظیم

- معده از موسین ترشح

Lipid transport in the circulation

Lipids are insoluble in plasma. In order to be transported they are combined with specific proteins to form lipoproteins:

Non polar lipids in core )TAG and cholesterol esters(

Proteins )apoproteins(

Cholesterol

Apoproteins are only weakly associated with a particular lipoprotein and are easily transferred to another lipoprotein of a different class. Apoproteins have various functions including: • Structural role  • Binding sites for receptors  • Activators or co-enzymes for enzymes involved with lipid metabolism 

HO

HO

O

R

HOHO

O

R

HOHOO

R

Lipoproteins

LDL & VLDLHDL

Assembled in intestinal mucosal cells. They enter the lymphatic system and enter the

blood via the thoracic duct. They contain mostly TAG. Nascent chylomicrons contain apoprotein B48

but pick up others apoproteins from high density lipoproteins (HDL) once they enter the circulation.

Chylomicrons

Cholesterol ester

Apoprotein

TAG )86%(

Cholesterol

phospholipid

Function is to transport dietary TAG to the adipose tissues where it can be stored as fat or to muscles where the constituent fatty acids can be used for energy.

The five classes of lipoprotein(all contain characteristic amounts TAG, cholesterol, cholesterol esters, phospholipids and apoproteins)

ClassDiameter

(nm) Source and functionMajor

apoliproteins

Chylomicrons(CM)

500 Intestine. Transport of dietary TAG

A, B48, C(I,II,III) E

Very low density lipoproteins

(VLDL)

43 Liver. Transport of endogenously

synthesised TAG

B100, C(I,II,III) , E

Low density lipoproteins

(LDL)

22 Formed in circulation by partial breakdown

of IDL. Delivers cholesterol to

peripheral tissues

B100

High density lipoproteins

(HDL)

8 Liver. Removes “used” cholesterol from

tissues and takes it to liver. Donates

apolipoproteins to CM and VLDL

A, C(I,II,III), D, E

Incr

easi

ng

den

sity