Introduction

Definition: water insoluble compounds

Most lipids are fatty acids or ester of fatty acid They are soluble in non-polar solvents such as petroleum ether, benzene, chloroform Energy storage Structure of cell membranes Thermal blanket and cushion Precursors of hormones (steroids and prostaglandins) Fatty acids Neutral lipids Phospholipids and other lipids

Functions

Types:

Fatty acids
Carboxylic acid derivatives of long chain hydrocarbons Nomenclature (somewhat confusing)

Stearate stearic acid C18:0 n-octadecanoic acid

General structure:

CH3

(CH2)n COOH

n = 0 : CH 3COOH n = 1 : propionic acid

n is almost always even

Fatty acids
Common fatty acids

n = 4 butyric acid (butanoic acid) n = 6 caproic acid (hexanoic acid) n = 8 caprylic acid (octanoic acid) n = 10 capric acid (decanoic acid)

Fatty acids
common FAs:
n = 12: lauric acid (n-dodecanoic acid; C12:0)
n = 14: myristic acid (n-tetradecanoic acid; C14:0) n = 16: palmitic acid (n-hexadecanoic acid; C16:0) n = 18; stearic acid (n-octadecanoic acid; C18:0) n = 20; arachidic (eicosanoic acid; C20:0) n= 22; behenic acid n = 24; lignoceric acid n = 26; cerotic acid

Less common fatty acids

H3C

iso isobutyric acid

anteiso

R
H3C

H3 C CH3

odd carbon fatty acid propionic acid

hydroxy fatty acids ricinoleic acid, dihydroxystearic acid, cerebronic acid

cyclic fatty acids hydnocarpic, chaulmoogric

acid

(CH2)12-CO2H

(CH2)10-CO2H

chaulmoogric acid

hydnocarpic acid

H3 C COOH CH3 CH3 CH3 CH3

PHYTANIC ACID A plant derived fatty acid with 16 carbons and branches at C 3, C7, C11 and C15. Present in dairy products and ruminant fats. A peroxisome responsible for the metabolism of phytanic acid is defective in some individuals. This leads to a disease called Refsums disease Refsums disease is characterized by peripheral polyneuropathy, cerebellar ataxia and retinitis pigmentosa

Less common fatty acids

H3C (CH2)10 C C (CH2)4 COOH TARIRIC ACID H2C CH (CH2)4 C C C C (CH2)7 COOH

ERYTHROGENIC ACID

These are alkyne fatty acids

Fatty acids
Fatty acids can be classified either as: saturated or unsaturated according to chain length:

short chain FA: 2-4 carbon atoms medium chain FA: 6 10 carbon atoms long chain FA: 12 26 carbon atoms essential fatty acids vs those that can be biosynthesized in the body: linoleic and linolenic are two examples of essential fatty acid

Unsaturated fatty acids

Monoenoic acid (monounsaturated)
H3C

Double bond is always cis in natural fatty acids. This lowers the melting point due to kink in the chain

HOOC

Unsaturated fatty acids

Dienoic acid: linoleic acid
CH3 (CH2)4 CH=CH CH2 CH=CH (CH2)7 COOH

cis linoleic acid

Unsaturated fatty acids

Various conventions are in use for indicating the number and position of the double bond(s)
18
H3C (CH 2)7 H C

CH( CH 2)7COOH

10 18:1,9 or 9 18:1

H3C

2 3 4

5 6 7 8 9

10

18

CH 2CH 2CH2CH 2CH 2CH 2CH2CH

CH( CH 2)7COOH

17 9, C18:1 or n-9, 18:1

10

Unsaturated fatty acids

Polyenoic acid (polyunsaturated)

COOH CH3

Unsaturated fatty acids

Monoenoic acids (one double bond):

16:1, 9 7: palmitoleic acid (cis-9-hexadecenoic acid 18:1, 9 9: oleic acid (cis-9-octadecenoic acid) 18:1, 9 9: elaidic acid (trans-9-octadecenoic acid) 22:1, 13 9: erucic acid (cis-13-docosenoic acid) 24:1, 15 9: nervonic acid (cis-15-tetracosenoic acid)

Unsaturated fatty acids

Trienoic acids (3 double bonds)

18:3;6,9,12 6 : g-linolenic acid (all cis-6,9,12-octadecatrienoic acid) 18:3; 9,12,15 3 : a-linolenic acid (all-cis-9,12,15octadecatrienoic acid) 20:4; 5,8,11,14 6: arachidonic acid (all-cis-5,8,11,14eicosatetraenoic acid)

Tetraenoic acids (4 double bonds)

Unsaturated fatty acids

Pentaenoic acid (5 double bonds)

20:5; 5,8,11,14,17 3: timnodonic acid or EPA (all-cis-5,8,11,14,17-eicosapentaenoic acid)* 22:6; 4,7,10,13,16,19 3: cervonic acid or DHA (all-cis-4,7,10,13,16,19-docosahexaenoic acid)*

Hexaenoic acid (6 double bonds)

Both FAs are found in cold water fish oils

Typical fish oil supplements

Properties of fats and oils

fats are solids or semi solids oils are liquids melting points and boiling points are not usually sharp (most fats/oils are mixtures) when shaken with water, oils tend to emulsify pure fats and oils are colorless and odorless (color and odor is always a result of contaminants) i.e. butter (bacteria give flavor, carotene gives color)

Examples of oils
Olive oil from Oleo europa (olive tree) Corn oil from Zea mays Peanut oil from Arachis hypogaea Cottonseed oil from Gossypium Sesame oil from Sesamum indicum Linseed oil from Linum usitatissimum Sunflower seed oil from Helianthus annuus Rapeseed oil from Brassica rapa Coconut oil from Cocos nucifera

Non-drying, semi-drying and drying oils

based on the ease of autoxidation and polymerization of oils (important in paints and varnishes) the more unsaturation in the oil, the more likely the drying process
Non-drying oils: Castor, olive, peanut, rapeseed oils Semi-drying oils Corn, sesame, cottonseed oils Drying oils Soybean, sunflower, hemp, linseed, tung, oiticica oils

Fatty acid reactions

salt formation
ester formation lipid peroxidation
RCO2H NaOH RCO2-Na + (a soap)

R'OH + RCO 2H

-H20

RCO2R'

R' R H H

O2 R non-enzymatic OOH very reactive R'

Soaps
Process of formation is known as saponification
Types of soaps: Sodium soap ordinary hard soap Potassium soap soft soap (shaving soaps are potassium soaps of coconut and palm oils) Castile soap sodium soap of olive oil Green soap mixture of sodium and potassium linseed oil Transparent soap contains sucrose Floating soap contains air Calcium and magnesium soaps are very poorly water soluble (hard water contains calcium and magnesium salts these insolubilize soaps)

Lipid peroxidation
a non-enzymatic reaction catalyzed by oxygen may occur in tissues or in foods (spoilage) the hydroperoxide formed is very reactive and leads to the formation of free radicals which oxidize protein and/or DNA (causes aging and cancer) principle is also used in drying oils (linseed, tung,

walnut) to form hard films

Hydrogenated fats
hydrogenation leads to either saturated fats and or

trans fatty acids the purpose of hydrogenation is to make the oil/fat more stable to oxygen and temperature variation (increase shelf life) example of hydrogenated fats: Crisco, margarine

Neutral lipids
Glycerides (fats and oils) ;glycerides Glycerol CH OH
2

OH OH OH

OH CH2OH

Ester of glycerol - glycerol mono glycerides, diglycerides and is a prochiral molecule

triglycerides

Waxes simple esters of long chain alcohols

GLYCERIDES
O O OH OH R O O O OH O O MONOGLYCERIDE DIGLYCERIDE R R R O O O TRIGLYCERIDE R O R O

Function: storage of energy in compact form and cushioning

WAXES
simple esters of fatty acids (usually saturated with long

chain monohydric alcohols)

O H3C (CH 2)14 C O CH 2 (CH 2)28-CH 3

fatty acid long chain alcohol

Beeswax also includes some free alcohol and fatty acids Spermaceti contains cetyl palmitate (from whale oil) useful for Pharmaceuticals (creams/ointments; tableting and granulation) Carnauba wax from a palm tree from brazil a hard wax used on cars and boats

Spermaceti source

Carnauba wax source

Bees wax

Waxes
H3C (CH2)14 CH2-OH cetyl alcohol H3C H3C (CH2)24 CH2-OH (CH2)28 CH2-OH hexacosanol triacontanol (myricyl alcohol)

Examples of long chain monohydric alcohols found in waxes

Phospholipids
the major components of cell membranes
phosphoglycerides
O

fatty acids (hydrophobic tail) glycerol

O OO P O O X R'

phosphate

Phospholipids are generally composed of FAs, a nitrogenous base, phosphoric acid and either glycerol, inositol or sphingosine

fatty acids (hydrophobic tail) glycerol

O OO P O O X R'

phosphate

X = H (phosphatidic acid) - precursor to other phospholipids X = CH2-CH2-N+(CH3)3 phosphatidyl choline X = CH2-CH(COO-)NH3+ phosphatidyl serine X = CH2-CH2-NH3+ phosphatidyl ethanolamine

Phosphatidyl inositol

Commonly utilized in cellular signaling

Sphingolipids
Based on sphingosine instead of glycerol
OH OH sphingosine NH 2

HO

long chain hydrocarbon

NH 2 OH

attach fatty acid here attach polar head group here

Sphingomyelin (a ceramide) R HO
O NH OO P O O N(CH3)+ R' usually palmitic acid

phosphatidyl choline (also can be ethanolami

It is a ubiquitous component of animal cell membranes, where it is by far the most abundant sphingolipid. It can comprise as much as 50% of the lipids in certain tissues, though it is usually lower in concentration than phosphatidylcholine

Ether glycerophospholipids
Possess an ether linkage instead of an acyl group at the

C-1 position of glycerol

PAF ( platelet activating factor) A potent mediator in inflammation, allergic response and in shock (also responsible for asthma-like symptom The ether linkage is stable in either acid or base Plasmalogens: cis a,b-unsaturated ethers
The alpha/beta unsaturated ether can be hydrolyzed more easily

Ether glycerophospholipids
O -O P O H2C O CH O C CH 3 O
H

CH 3 O CH 2 CH 2 N CH 3
H2C O CH O C O

CH 3 O CH 2 CH 2 N CH 3 CH 3

CH 3

-O

P O CH 2

CH 2
H

platelet activating factor or PAF

A choline plasmalogen

glycolipids
HO O NH O R' SUGAR polar head is a sugar R

beta link age

There are different types of glycolipids: cerebrosides, gangliosides, lactosylceramides

GLYCOLIPIDS
Cerebrosides

One sugar molecule

Galactocerebroside in neuronal membranes Glucocerebrosides elsewhere in the body

Sulfatides or sulfogalactocerebrosides

A sulfuric acid ester of galactocerebroside Lactosylceramide

Globosides: ceramide oligosaccharides

2 sugars ( eg. lactose)

Gangliosides

Have a more complex oligosaccharide attached Biological functions: cell-cell recognition; receptors for hormones

Gangliosides
complex glycosphingolipids that consist of a ceramide

backbone with 3 or more sugars esterified,one of these being a sialic acid such as N-acetylneuraminic acid common gangliosides: GM1, GM2, GM3, GD1a, GD1b, GT1a, GT1b, Gq1b

Ganglioside nomenclature
letter G refers to the name ganglioside
the subscripts M, D, T and Q indicate mono-, di-, tri,

and quatra(tetra)-sialic-containing gangliosides the numerical subscripts 1, 2, and 3 designate the carbohydrate sequence attached to ceramide

Ganglioside nomenclature
Numerical subscripts:

1. Gal-GalNAc-Gal-Glc-ceramide 2. GalNAc-Gal-Glc-ceramide 3. Gal-Glc-ceramide

N-Acetyl-D-galactosamine
CH 2OH OH O OH H H OH H O H NH C CH 3 O H3C C NH CHOH CHOH CH 2OH H H O O H H OH O O CH 2OH

D-galactose
CH 2OH H O H H H OH O

D-glucose
CH 2OH O OH H H H HO H C OH H C O H C NH C C H R O CH 2

D-Galactose

O COO-

OH

N-acetylneuraminidate (sialic acid)

A ganglioside (GM1)

Cardiolipids
O O R2 C O H2C C H2C O H O C O P OH glycerol glycerol O R1 H CH2 C OH CH2 O R4 O C O P OH glycerol O H O CH2 C CH2 O O C R3

A polyglycerol phospholipid; makes up 15% of total lipid-phosphorus content of the myocardium associated with the cell membrane Cardiolipids are antigenic and as such are used in serologic test for syphilis (Wasserman test)

Sulfolipids
also called sulfatides or cerebroside sulfates
contained in brain lipids sulfate esters of cerebrosides present in low levels in liver, lung, kidney, spleen,

skeletal muscle and heart function is not established

Lipid storage diseases

also known as sphingolipidoses genetically acquired due to the deficiency or absence of a catabolic enzyme examples:

Tay Sachs disease Gauchers disease Niemann-Pick disease Fabrys disease

http://www.ninds.nih.gov/disorders/lipid_storage_disease

s/lipid_storage_diseases.htm

Genetic defects in ganglioside metabolism

leads to a buildup of gangliosides (ganglioside GM2) in

nerve cells, killing them

enzyme that hydrolyzes here (beta hexosaminodase) is absent in Tay-Sachs disease Gal NAc Gal Gal Glu NAcNeu

Tay-Sachs disease
a fatal disease which is due to the deficiency of hexosaminidase A activity accumulation of ganglioside GM2 in the brain of infants mental retardation, blindness, inability to swallow a cherry red spot develops on the macula (back of the the eyes) Tay-Sachs children usually die by age 5 and often sooner

Genetic defects in globoside metabolism

Fabrys disease:

Accumulation of ceramide trihexoside in kidneys of patients who are deficient in lysosomal a-galactosidase A sometimes referred to as ceramide trihexosidase Skin rash, kidney failure, pains in the lower extremities Now treated with enzyme replacement therapy: agalsidase beta (Fabrazyme)

Genetic defects in cerebroside metabolism

Krabbes disease:

Also known as globoid leukodystrophy Increased amount of galactocerebroside in the white matter of the brain Caused by a deficiency in the lysosomal enzyme galactocerebrosidase Caused by a deficiency of lysosomal glucocerebrosidase Increase content of glucocerebroside in the spleen and liver Erosion of long bones and pelvis Enzyme replacement therapy is available for the Type I disease (Imiglucerase or Cerezyme) Also miglustat (Zavesca) an oral drug which inhibits the enzyme glucosylceramide synthase, an essential enzyme for the synthesis of most glycosphingolipids

Gauchers disease:

Miglustat (Zavesca)

Genetic defects in ganglioside metabolism

Metachromatic leukodystrophy

accumulation of sulfogalactocerebroside (sulfatide) in the central nervous system of patient having a deficiency of a specific sulfatase mental retardation, nerves stain yellowish-brown with cresyl violet dye (metachromasia) accumulation of ganglioside GM1 deficiency of GM1 ganglioside: b-galactosidase mental retardation, liver enlargement, skeletal involvement

Generalized gangliosidosis

Niemann-Pick disease
principal storage substance: sphingomyelin which

accumulates in reticuloendothelial cells enzyme deficiency: sphingomyelinase liver and spleen enlargement, mental retardation

Blood groups
determined by various glycolipids on RBCs
A antigens
AcN
Gal Ac N Glu-sphingosine

B antigens
H antigens
Gal

L-Fucose

Gal

NAc-Glu-sphingosine

L-Fucose

Gal

NA c--Glu-sphingosine L-Fucose

(found on type O blood cells)

not recognized by anti-A or anti-B antibodies

Cholesterol and cholesterol esters

H3C CH3 CH3 H OH H H drawn this way R O usually palmitate hydrophillic

hydrophobic O

STEROID NUMBERING SYSTEM

18 12 11 19 1 2 A 3 4 C 13 14 7 6 17 D 15 16

9 10 8 B 5

STEREOCHEMISTRY OF STEROIDS
CH3 H CH3 H H H H H CH3 H H CH3 H H CH3 H CH3

CH3 H HO H

CH3 OH

Cholesterol sources, biosynthesis and degradation

diet: only found in animal fat
biosynthesis: primarily synthesized in the liver from

acetyl-coA; biosynthesis is inhibited by LDL uptake degradation: only occurs in the liver

Cholesterol and cholesterol esters

H H HO H R O H O usually palmitate

H H

The hydroxyl at C-3 is hydrophilic; the rest of the molecule is hydrophobic; also 8 centers of asymmetry

Cholesterol and cholesterol esters

H HO

Functions: -serves as a component of membranes of cells (increases or moderates membrane fluidity -precursor to steroid hormones -storage and transport cholesterol esters

Functions of cholesterol
serves as a component of membranes of cells

(increases or moderates membrane fluidity) precursor to steroid hormones and bile acids storage and transport cholesterol esters

Prostaglandins and other eicosanoids (prostanoids)

local hormones, unstable, key mediators of

inflammation derivatives of prostanoic acid

9 8 COOH 20 11 12 15 prostanoic acid

O O O OO P O O X H2 0 phospholipase A 2 (enzyme that hydrolyzes at the sn-2 position - inhibited indirectly by corticosteroids) O R

COOH CH3

COX is inhibibited by prostaglandin synthase aspirin and other NSAIDs (also k nown as cyclooxygenase)

very unstable bond

COOH

O OH PGH 2

COOH

O OH PGH 2 O HO COOH COOH

HO PGE 2

OH

HO

OH PGF 2a

k ey mediator of inflammation

O R1

O R1

O R1

HO R1

R2 PGA O R1 PGB

R2 PGC

R2 O PGD

R2

HO R1 O R1 O R2 R2 HO PGFa PGG and PGH O R2

R1

HO PGE

R2 HO PGI

R1

O R1 O R1

OH R1

R2 O PGJ O PGK

R2

O TXA

R2

HO

O TXB

R2

SUBSTITUTION PATTERN OF PROSTANOIDS

Prostacyclins, thromboxanes and leukotrienes

PGH2 in platelets is converted to thromboxane A2 (TXA2) a vasoconstrictor which also promotes platelet aggregation
PGH2 in vascular endothelial cells is converted to PGI2, a vasodilator which inhibits platelet aggregation Aspirins irreversible inhibition of platelet COX leads to its anticoagulant effect

Functions of eicosanoids
Prostaglandins particularly PGE1 block gastric production and thus are gastric protection agents Misoprostol (Cytotec) is a stable PGE1 analog that is used to prevent ulceration by long term NSAID treatment PGE1 also has vasodilator effects
Alprostadil (PGE1) used to treat infants with

congenital heart defects Also used in impotance (Muse)

Functions of eicosanoids
PGF2a causes constriction of the uterus Carboprost; Hebamate (15-Me-PGF2a) induces abortions PGE2 is applied locally to help induce labor at term

Examples of drugs derived from prostaglandins

Leukotrienes
Leukotrienes are derived from arachidonic acid via the enzyme 5-lipoxygenase which converts arachidonic acid to 5-HPETE (5-hydroperoxyeicosatetranoic acid) and subsequently by dehydration to LTA4

OH COOH H C5H11 H S Cys gGlu LEUKOTRIENE F 4 (LTF4) C5H11

OH COOH S Cys gGlu LEUKOTRIENE C 4 (LTC 4) Gly

peptidoleukotrienes

Leukotrienes
Leukotrienes are synthesized in neutrophils, monocytes, macrophages, mast cells and keratinocytes. Also in lung, spleen, brain and heart. A mixture of LTC4, LTD4 and LTE4 was previously known as the slow-reacting substance of anaphylaxis

OH OH COOH COOH H H C5H11 S Cys LEUKOTRIENE E

4

C5H11

S Cys Gly

(LTE4)

LEUKOTRIENE D 4 (LTD 4)

peptidoleukotrienes

Leukotrienes
Non-peptidoleuktrienes: LTA4 is formed by dehydration of 5-HPETE, and LTB4 by hydrolysis of the epoxide of LTA4

O COOH C5H11 HO LEUKOTRIENE A

4

(LTA4) C5H11 OH

COOH

LEKOTRIENE B 4 (LTB4)

Biological activities of leukotrienes

1. LTB4 2. LTC4 3. LTD4 4. LTE4 - potent chemoattractent - mediator of hyperalgesia - growth factor for keratinocytes - constricts lung smooth muscle - promotes capillary leakage 1000 X histamine - constricts smooth muscle; lung - airway hyperactivity - vasoconstriction - 1000 x less potent than LTD4 (except in asthmatics)

Leukotriene receptor antagonists

Zafirlukast (Accolate)

Montelukast (Singulair)

Lipid-linked proteins
Lipid-linked proteins (different from lipoproteins) lipoproteins that have lipids covalently attached to them these proteins are peripheral membrane proteins

Lipid-linked proteins
3 types are most common: Prenylated proteins

Farnesylated proteins (C15 isoprene unit) Geranylgeranylated proteins (C20 isoprene unit) Myristoylated proteins (C14) Palmitoylated proteins (C16)

Fatty acylated proteins

Lipid-linked proteins
glycosylphosphatidylinositol-linked proteins (GPI-

linked proteins)
occur in all eukaryotes, but are particularly abundant in

parasitic protozoa located only on the exterior surface of the plasma membrane

Fatty acylated proteins

Prenylated proteins

GPI-linked proteins

Lipoproteins
particles found in plasma that transport lipids including cholesterol lipoprotein classes

chylomicrons: take lipids from small intestine through lymph cells very low density lipoproteins (VLDL) intermediate density lipoproteins (IDL) low density lipoproteins (LDL) high density lipoproteins (HDL) Terpenes

Lipoprotein class
HDL

Density (g/mL)
1.063-1.21

Diameter (nm)
5 15

Protein % Phosphol of dry wt ipid %

33 29

Triacylglycerol % of dry wt
8

LDL

1.019 1.063 1.006-1.019

18 28

25

21

IDL

25 - 50

18

22

31

VLDL

0.95 1.006

30 - 80

10

18

50

chylomicrons

< 0.95

100 - 500

1-2

84

Composition and properties of human lipoproteins

most proteins have densities of about 1.3 1.4 g/mL and lipid aggregates usually have densities of about 0.8 g/mL

Lipoprotein structure

LDL molecule

The apolipoproteins
major components of lipoproteins often referred to as aproteins classified by alphabetical designation (A thru E) the use of roman numeral suffix describes the order in which the apolipoprotein emerge froma chromatographic column responsible for recognition of particle by receptors

HELICAL WHEEL PROJECTION OF A PORTION OF APOLIPOPROTEIN A-I

LIPOPROTEINS
spherical particles with a hydrophobic core (TG and

esterified cholesterol) apolipoproteins on the surface

large: apoB (b-48 and B-100) atherogenic smaller: apoA-I, apoC-II, apoE

classified on the basis of density and electrophoretic

mobility (VLDL; LDL; IDL;HDL; Lp(a)

Apoproteins of human lipoproteins

A-1 (28,300)- principal protein in HDL

90 120 mg% in plasma 30 50 mg %

A-2 (8,700) occurs as dimer mainly in HDL

B-48 (240,000) found only in chylomicron <5 mg % B-100 (500,000) principal protein in LDL

80 100 mg %

Apoproteins of human lipoproteins

C-1 (7,000) found in chylomicron, VLDL, HDL

4 7 mg % 3 8 mg % 8 15 mg % 8 10 mg % 3 6 mg %

C-2 (8,800) - found in chylomicron, VLDL, HDL

C-3 (8,800) - found in chylomicron, VLDL, IDL, HDL

D (32,500) - found in HDL

E (34,100) - found in chylomicron, VLDL, IDL HDL

Major lipoprotein classes

chylomicrons density <<1.006 diameter 80 - 500 nm dietary triglycerides apoB-48, apoA-I, apoA-II, apoA-IV, apoC-II/C-III, apoE remains at origin in electrophoretic field

Major lipoprotein classes

VLDL density >1.006 diameter 30 - 80nm endogenous triglycerides apoB-100, apoE, apoC-II/C-III prebeta in electrophoresis

Major lipoprotein classes

IDL (intermediate density lipoproteins) density: 1.006 - 1.019 diameter: 25 - 35nm cholesteryl esters and triglycerides apoB-100, apoE, apoC-II/C-III slow pre-beta

Major lipoprotein classes

HDL (high density lipoproteins) density: 1.063-1.210 diameter: 5-12nm cholesteryl esters and phospholipids apoA-I, apoA-II, apoC-II/C-III alpha (electrophoresis)

Major lipoprotein classes

LDL (low density lipoproteins) density: 1.019 - 1.063 diameter: 18-25nm cholesteryl esters apoB-100 beta (electrophoresis) < 130 LDL cholesterol is desirable, 130-159 is borderline high and >160 is high

Photograph of an arterial plaque

The LDL receptor

characterized by Michael Brown and Joseph Goldstein (Nobel prize winners in 1985) based on work on familial hypercholesterolemia receptor also called B/E receptor because of its ability to recognize particles containing both apos B and E activity occurs mainly in the liver receptor recognizes apo E more readily than apo B100

Representation of the LDL receptor

Terpenes
simple lipids, but lack fatty acid component
formed by the combination of 2 or more molecules of 2-methyl-1,3-butadiene (isoprene) monoterpene (C-10) made up of 2 isoprene units sesquiterpene (C-15) made up of 3 isoprene units diterpene (C-20) made up of 4 isoprene units

Monoterpenes
CHO OH

limonene

citronellal

menthol

camphene

Monoterpenes are readily recognized by their characterisitic flavors and odors ( limonene in lemons, citronellal in roses and geraniums, pinene in turpentine and menthol from peppermint

Sesquiterpenes

HO

bisabolene

eudesmol

Diterpenes
OH H CH 2OH HO C O H CH 3 COOH O

phytol

gibberelic acid

H3C

CH 3

CH 3

CH 3

CH 3

All-trans-retinal

Triterpenes

HO H

squalene

lanosterol

Triterpenes are C-30 compounds are addition products of 2 sesquiterpenes; Both squalene and lanosterol are precursors of cholesterol and other steroids

Other terpenes
tetraterpenes (C-40) are not as common as mono, di, and triterpenes
include the carotenoids such as beta-carotene

(precursor of vitamin A) and lycopene found in tomatoes usually colorful compounds due to highly conjugated system

polyisoprenoids or polyprenols consist of numerous isoprene adducts (8 22)

examples include dolichol phosphate, undecaprenyl

alcohol (bactoprenol) and the side chains of vitamins K, vitamin E and coenzyme Q