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Lipids

Introduction

What nature tucks into our tummy cells during periods of abundant eating, are large ester molecules with long hydrocarbon chains.

Introduction
These members of the lipid family, and the systems are good storehouses of chemical energy. The outer membranes of every cell of the body are also made of such molecules, plus membrane-bound proteins and cholesterol.

What are Lipids?


from Greek lipos, fat Family of substances that are insoluble in water but soluble in non polar solvents and solvents of low polarity. Lipids are better defined in terms of a property and not in terms of their structure.

Classification by Function

Three major roles in human biochemistry


They store energy within fat cells; They are parts of membranes that separate compartments of aqueous solutions from each other; They serve as chemical messengers.

Storage
An important use of lipids. Animals (including humans) find it more economical to use fats instead. Though we store some carbohydrates (glycogen) for quick energy source, energy stored in the form of fats has greater importance.

Storage

The burning of fats produces more than twice as much energy as burning of an equal weight of carbohydrates.

Membrane Components
The lack of water solubility of lipids is an important property because our body chemistry is so heavily based in water. Serves as insoluble compounds for the membranes that separate compartments containing aqueous solutions.

Messengers
Also serve as chemical messengers Primary messengers

Such as steroid hormones, deliver signals from one part of the body to another part

Secondary messengers
Such as prostaglandins and thromboxanes, mediate the hormonal response

Properties
Substance must be insoluble in water Must be soluble in nonpolar solvents such as ether, chloroform, acetone, benzene, methanol Must be found in biological systems

Classification
Fats and waxes Complex lipids Sphingolipids Steroids Prostaglandins, thromboxanes and leukotrienes

Fatty acids
Long chain aliphatic carboxylic acid Saturated aliphatic fatty acids have higher melting point due to London forces or hydrophobic interactions with each other Double bonds in the unsaturated fatty acids are in the cis conformation Functions are regulatory molecules, energy sources or structural materials

Classification

Triaglycerols
Esters of fatty acids with glycerol

Glycerolphospholipids
Esters of glycerol with fatty acids and phosphate derivatives

Waxes
Esters of a fatty acid with long chain alcohol

Classification

Sphingolipids
Esters of fatty acids with sphingosine

Steroids
Polycyclic aliphatics

Prostaglandins and Leukotrienes


Oxidized derivatives of C-20 fatty acids

Fatty Acids, Waxes, and Oils


Are long chain carboxylic acids (usually even number of carbons) It can be saturated or unsaturated Saturated

Only aliphatic carbons

Unsaturated
Contain C=C double bonds generally all cis-conformations.

Fatty Acids, Waxes, and Oils


Multiple sites of unsaturation are polyunsaturated fatty acids Single sites of unsaturation are monounsaturated fatty acids Linoleic and linolenic are essential fatty acids in the human diet

Arachidonic acid can be synthesized from linolenic acid)

Animal Fats and Vegetable Oils: Triglycerides


Animal fats and plant oils are triglycerides These are triesters of glycerol and long-chain carboxylic acids called fatty acids.

glycerol

Triglycerides

Triglycerides
Also called triacylglycerols Most common lipid materials Complex mixtures Hydrophobic character of triglycerides is caused by the long hydrocarbon chains The ester groups, although polar, are buried in a nonpolar environment, which makes it insoluble in water.

Properties
With some exceptions, generally solids at room temperature (animal fats) and liquid for plants or fish fats. Fat a mixture of triglycerides containing a high proportion of longchain saturated fatty acids

Properties
Liquid fats are often called oils. Oil A mixture of triglycerides containing a high proportion of longchain, unsaturated fatty acids or shortchain, saturated fatty acids Oils can be mono or polyunsaturated fatty acids

More unsaturation leads to lower melting point.

Properties
Function as storage of energy Contains glycerides as its major component Glycerides are storage form of fats in cells and functions as insulating substances to keep organism warm when temperature of environment decreases

Properties

Location of double bonds determine the omega number

Properties

Properties
The degree of unsaturation characterizes the: Firmness Stability Oxidation Antioxidants

Glyceryl Ethers
Rare lipids found mostly in neoplasms or cancer cells Main feature: ether linkage between a fatty acid and a glycerol

Biological Waxes
Are esters of long-chain saturated and unsaturated fatty acids (14 to 36 carbon atoms) and with alcohols (16 to 30 carbon atoms) Serves as energy storage and waterimpermeable coatings

Biological Waxes
In marine organism that constitute planktons, waxes are the chief storage from of metabolic fuel. Certain skin glands of vertebrates secrete waxes to protect the hair and skin Keep them pliable, lubricated and waterproof

Reactions of Waxes and Triglycerides


Hydrogenation of Unsaturated C=C double bonds Hydrolysis of Ester bonds

Hydrogenation
Problem on formation of trans C=C double bonds Suspected as a problem underlying cardiovascular diseases

Hydrolysis of Ester Bonds


Generally catalyzed by KOH or NaOH Produces soap by heating with base Saponification process Na+ or K+ salts of the fatty acid

Hydrolysis of Ester Bonds

Salts of fatty acids are amphophthic have hydropillic and hydrophobic portions on the same molecule (form MICELLES property making soap a good solvent for oils in aqeuous soultions

Membrane Lipids
Phospholipids Sphingolipids Glycolipids

Phospholipids
Glycerophospholipids or phosphoglycerides Glycerol plus two fatty acyl ester bond

third position on glycerol is linked to phosphate which in turn esterified to another small molecule

Structure

Phospholipids
Function is to comprise the membrane of cells and intracellular organelles It forms a bilayer membrane structure

Sphingolipids
Esters of phosphate and small molecules with sphingosine Sphingomyelin (containing choline) is a major constitutent of the membranes of the myelin sheath surrounding the nerve fibers

Glycolipids

Sphingosine
are lipids containing carbohydrate instead of phosphate ester

Cerebrosides or Gangliosides
Important cell surface components of nerve receptors

Structures of Cell Membranes

Structures of Cell Membranes


Proteins imbedded Proteins attached Contains cholesterol (somes cells) increases fluidity Glycolipids and glycoproteins generally on outer surface of plasma membrane Membrane proteins are attached to or imbedded in the p-lipid bilayer

Cholesterol and Other Steroids

Steroids
lipids based on the tetracyclic ring structure

Sterols (Steroidal Alcohols) Prostaglandins and Leukotrienes Thromboxanes Pheromones Terpenes Eicosanoids

Cholesterol
Most abundant animal sterol Esterified cholesterol is ester with a long chain fatty acid Primarily found in membranes increasing fluidity of the membrane Source of biosynthesis of other cell material including bile acids and steroid hormones

Steroid hormones

Sex hormones
Testosterone Androsterone Estrone Estradiol Progesterone

Adrenal Cortical Hormones


Aldosterone Hydrocortisone conrtisone

Prostaglandins
C-20 carboxylic acids synthesized from arachadonic acid Function as intercellular signals (like hormones but not long range)

Thromboxanes
Causes platelet coagulation Produced by thrombocytes

Pheromones

Usually low molecular weight lipids which are volatile

Terpenes
Includes fat-soluble vitamins Common structural unit: isoprene unit

Eicosanoids
Derivatives of arachidonic acid Responsible for many physiological effects Some used in treatment of hypertension, relief of asthma, induction of abortion and prevention of conception.