Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar...

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Chapter 9 (part 1) Lipids and Membranes

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Transcript of Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar...

Page 1: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Chapter 9 (part 1)

Lipids and Membranes

Page 2: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Lipids

• Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water.

• Can be hydrophobic or amphipathic

Page 3: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Major Lipid Classes

•Acyl-lipids - contain fatty acid groups as main non-polar group

• Isoprenoids – made up of 5 carbon isoprene units

Page 4: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Lipid Subclasses

Page 5: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Function of major acyl-lipids

• Phospholipids – membrane components• Triacylglycerols – storage fats and oils• Waxes – moisture barrier• Eicosanoids – signaling molecules

(prostaglandin)• Sphingomyelins – membrane

component (impt. in mylein sheaths)• Glycospingolipids – cell recognition

(ABO blood group antigen)

Page 6: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Function of major isoprenoid lipids

• Steroids (sterols) – membrane component, hormones

• Lipid Vitamins – Vitamin A, E, K• Carotenoids - photosynthetic accessory

pigments• Chlorophyll – major light harvesting pigment• Plastoquinone/ubiquinone – lipid soluble

electron carriers• Essential oils – menthol

Page 7: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Fatty acids• Amphipathic molecule• Polar carboxyl group• Non-polar hydrocarbon tail• Diverse structures (>100

different types)• Differ in chain length• Differ in degree of

unsaturation• Differ in the position of double

bonds• Can contain oxygenated

groups

Page 8: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Fatty acid nomenclature

• Short hand nomenclature describes total number of carbons, number of double bonds and the position of the double bond(s) in the hydrocarbon tail.

C18:1 9 = oleic acid, 18 carbon fatty acid

with a double bond positioned at the ninth carbon counting from and including the carboxyl carbon (between carbons 9 and 10)

C1

C2C3

C4C5

C6C7

C8C9

C10C11

C12C13

C14C15

C16C17

C18O

HO

Page 9: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Fatty acid nomenclature

• Omega () notation – counts carbons from end of hydrocarbon chain.

• Omega 3 fatty acids advertised as health promoting

• Linoleate = 18:3 9,12,15 and 18:33,6,9

C1

C2C3

C4C5

C6C7

C8C9

C10C11

C12C13

C14CH15

C16C17

C18O

HO

Page 10: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Common saturated fatty acids

common name IUPAC name melting point (Co)

12:0 laurate dodeconoate 44

14:0 myristate tetradeconoate 52

16:0 palmitate hexadeconoate 63

18:0 stearate octadeconoate 70

20:0 arachidate eicosanoate 75

22:0 behenate docosanoate 81

24:0 lignocerate tetracosanate 84

Page 11: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Common unsaturated fatty acids

common name IUPAC namemelting point

(Co)

16:0 palmitate hexadeconoate 63

16:1 9 palmitoleate cis-9-hexadeconoate -0.5

18:0 stearate octadeconoate 70

18:1 9 oleate cis-9- octadeconoate 13

18:2 9,12 linoleate cis-9,12- octadeconoate -9

18:3 9,12,15 linolenate cis-9,12,15- octadeconoate -17

20:0 arachidate eicosanoate 75

20:4 5,8,11,14 arachindonate cis- 5,8,11,14-eicosatetraenoate -49

Page 12: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Physical Properties of Fatty acids

• Saturated chains pack tightly and form more rigid, organized aggregates

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

18:0 18:1 18:3

70o 13o -17o

Page 13: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Melting points of fatty acids affect properties of acyl-

lipids• Membrane fluidity determined by

temperature and the degree of fatty acid unsaturation of phospholipids

• Certain bacteria can modulate fatty acid unsaturation in response to temperature

• Difference between fats and oils • Cocoa butter – perfect melt in your mouth

fat made of triacylglycerol with 18:0-18:1-18:0 fatty acids

• Margarine is hydrogenated vegetable oil. Increase saturation of fatty acids. Introduces trans double bonds (thought to be harmful)

Page 14: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Unusual fatty acids can function analogously to unsaturated fatty

acids

Page 15: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Major acyl-lipids•Phospholipids – membrane components

•Triacylglycerols – storage fats and oils

•Waxes – moisture barrier

•Eicosanoids – signaling molecules (prostaglandin)

•Sphingomyelins – membrane component (impt. in mylein sheaths)

•Glycospingolipids – cell recognition (ABO blood group antigen)

Page 16: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Phospholipids

• Phospholipids are built on glycerol back bone.

• Two fatty acid groups are attached through ester linkages to carbons one and two of glycerol.

• Unsaturated fatty acid often attached to carbon 2

• A phosphate group is attached to carbon three

• A polar head group is attached to the phosphate (designated as X in figure)

Page 17: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.
Page 18: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Common membrane phospholipids

P

O

OO

O

H

CH2

HCH2C

O O

C C OO

R1 R2

P

O

OO

O

CH2

CH2

HCH2C

O O

C C OO

R1 R2

CH2

NH3

P

O

OO

O

CH2

CH2

HCH2C

O O

C C OO

R1 R2

CH2 COO

NH3

P

O

OO

O

CH2

CH2

HCH2C

O O

C C OO

R1 R2

CH2

NH3C CH3

CH3

Phophtidate Phophatidylethanolamine Phophatidylserine Phophatidylcholine

Page 19: Chapter 9 (part 1) Lipids and Membranes. Lipids Lipids are compounds that are soluble in non-polar organic solvents, but insoluble in water. Can be hydrophobic.

Enzymes used to Dissect Phospholipid Structure

P

O

OO

O

X

CH2

HCH2C

O O

C C OO

R1 R2

phospholipase D

phospholipase C

phospholipase A2phospholipase A1


1 Lipids Lipids are the hydrophobic compounds of C, H and O With much higher ratio of hydrogen to oxygen than carbohydrates Most are insoluble in water.

1 Lipids Lipids are the hydrophobic compounds of C, H and O With much higher ratio of hydrogen to oxygen than carbohydrates Most are insoluble in water.

Lipids are a diverse group of hydrophobic molecules Lipids are the one class of large biological molecules that do not form polymers Lipids are hydrophobic.

Lipids are a diverse group of hydrophobic molecules Lipids are the one class of large biological molecules that do not form polymers Lipids are hydrophobic.

Lipids. Lipids = fats that are mostly energy storing molecules Hydrophobic Two “Monomers” = glycerol and fatty acids Lipids.

Lipids. Lipids = fats that are mostly energy storing molecules Hydrophobic Two “Monomers” = glycerol and fatty acids Lipids.

Chapter 5. Metabolism of Lipids Lipids Insoluble or immiscible Triacylgerols store and supply energy for metabolism. Lipoids: phospholids, glycolipids,

Chapter 5. Metabolism of Lipids Lipids Insoluble or immiscible Triacylgerols store and supply energy for metabolism. Lipoids: phospholids, glycolipids,

LIPIDS. THE LIPID FAMILY ORGANIC COMPOUNDS INSOLUBLE IN WATER INCLUDE: TRIGLYCERIDES PHOSPHOLIPIDS STEROLS.

LIPIDS. THE LIPID FAMILY ORGANIC COMPOUNDS INSOLUBLE IN WATER INCLUDE: TRIGLYCERIDES PHOSPHOLIPIDS STEROLS.

Cell Membranes: Lipids (Ch 10) - Washington State Universityc093).pdfpolar head 2 hydrophobic tails Lipids Lipids are amphipathic A lipid has a hydrophilic polar head and 2 hydrophobic

Cell Membranes: Lipids (Ch 10) - Washington State Universityc093).pdfpolar head 2 hydrophobic tails Lipids Lipids are amphipathic A lipid has a hydrophilic polar head and 2 hydrophobic

Fats and Lipids. Lipids Lipids are varied in structure. –Many are insoluble in water because they lack polar groups. Types of Lipids and their Functions.

Fats and Lipids. Lipids Lipids are varied in structure. –Many are insoluble in water because they lack polar groups. Types of Lipids and their Functions.

Lipids. Defintion of lipids: hydrophobic small molecules slightly soluble in organic solvent (e.g. chloroform or methyl alcohol)

Lipids. Defintion of lipids: hydrophobic small molecules slightly soluble in organic solvent (e.g. chloroform or methyl alcohol)

The Lipids. Introduction to Lipids Lipids – water insoluble component of cells Hydrophobic Hydrophobic Made of the elements: Made of the elements: CarbonCarbon.

The Lipids. Introduction to Lipids Lipids – water insoluble component of cells Hydrophobic Hydrophobic Made of the elements: Made of the elements: CarbonCarbon.

Lipids Water insoluble (hydrophobic) Non-polymeric structure Energy storage, membrane constituent, hormone signaling Migrate over-water 2,400 miles.

Lipids Water insoluble (hydrophobic) Non-polymeric structure Energy storage, membrane constituent, hormone signaling Migrate over-water 2,400 miles.

Chap. 6: Lipids Properties of Lipids Non-polar: water insoluble Energy density = Monomers: fatty acids & glycerol.

Chap. 6: Lipids Properties of Lipids Non-polar: water insoluble Energy density = Monomers: fatty acids & glycerol.

Chapter 9 - Lipids and Membranes Lipids are essential components of all living organisms Lipids are water insoluble organic compounds They are hydrophobic.

Chapter 9 - Lipids and Membranes Lipids are essential components of all living organisms Lipids are water insoluble organic compounds They are hydrophobic.

Lipids Lipids are water insoluble, oily or greasy organic compounds soluble in non-polar organic solvents. Chemically, lipids are defined as the esters.

Lipids Lipids are water insoluble, oily or greasy organic compounds soluble in non-polar organic solvents. Chemically, lipids are defined as the esters.

Defined on the basis of solubility. Lipids are heterogeneous group of water insoluble (hydrophobic) organic molecules, they are chemically diverse compound.

Defined on the basis of solubility. Lipids are heterogeneous group of water insoluble (hydrophobic) organic molecules, they are chemically diverse compound.

Chapter 5 lipids metabolism LIPIDS Water-insoluble substances that can be extracted from cells by nonpolar organic solvents Characteristics of fat Hydrophobic.

Chapter 5 lipids metabolism LIPIDS Water-insoluble substances that can be extracted from cells by nonpolar organic solvents Characteristics of fat Hydrophobic.

Lipids: Nature’s Flavor Enhancers. Lipids… a category of organic compounds that are insoluble in water and have a greasy feel.

Lipids: Nature’s Flavor Enhancers. Lipids… a category of organic compounds that are insoluble in water and have a greasy feel.

Lipid metabolism Pavla Balínová. Lipids Lipids dissolve well in organic solvents but they are insoluble in water. Biological roles of lipids: ● lipids.

Lipid metabolism Pavla Balínová. Lipids Lipids dissolve well in organic solvents but they are insoluble in water. Biological roles of lipids: ● lipids.

Lipids - academic.mu.eduacademic.mu.edu/bisc/siebenlistk/HCOPlipids.pdf · Lipids are the non-polar, hydrophobic, water insoluble components of the cell. Lipids are soluble in non-polar

Lipids - academic.mu.eduacademic.mu.edu/bisc/siebenlistk/HCOPlipids.pdf · Lipids are the non-polar, hydrophobic, water insoluble components of the cell. Lipids are soluble in non-polar

Lipids Lipids are non-polar (hydrophobic) organic compounds, insoluble in water, soluble in organic solvents (ether, acetone, carbontetrachloride).

Lipids Lipids are non-polar (hydrophobic) organic compounds, insoluble in water, soluble in organic solvents (ether, acetone, carbontetrachloride).

Metabolism of Dietary Lipids Definition: Lipids are heterogeneous gp of water-insoluble (hydrophobic) organic molecules stored as triacylglycerol in adipose.

Metabolism of Dietary Lipids Definition: Lipids are heterogeneous gp of water-insoluble (hydrophobic) organic molecules stored as triacylglycerol in adipose.