GENERAL BIOCHEMISTRY (BCH 201)

SECTION: CHEMISTRY OF LIPIDS

Course Outline

 Definition and concept of lipids

 Functions of lipids

 Fatty acids as common components of lipids

 Types of fatty acids

 Properties of lipids

 Chemical reactions of lipids

 Classification of lipids

 Lipid structures in aqueous medium

Definition and concept of lipids

The term lipid originates from the Greek word ‘lipos’ which literally means fat. Lipids are

diverse group of naturally occurring compounds that are generally insoluble in inorganic or polar

solvents such as water but highly soluble in non-polar organic solvents such as benzene,

chloroform and ether. This is because they are hydrocarbons that are mostly made up of nonpolar

carbon–carbon or carbon–hydrogen bonds. They are largely non-polar in nature, hence, highly

hydrophobic (“water fearing”), or insoluble in water. Lipids are made of the

elements Carbon, Hydrogen and Oxygen, but have a much lower proportion of water than other

molecules such as carbohydrate

Lipids principally exist as fats and oils. Fats are usually of animal origin whereas oils are of plant

origin. Fats are lipids which are solid at room temperature while oils are lipids which are liquids

at room temperature. Also fats and oils differ is that fats are rich in saturated fatty acids while

oils have more of unsaturated fatty acids

Lipids are one of the major macromolecules including carbohydrates, proteins and nucleic acids

but unlike the aforementioned (carbohydrates, proteins and nucleic acids), lipids are not regarded

as polymers. This is because they lack a repeating monomeric unit. They are the chief storage

form of energy in most organisms. They provide 6-fold as much energy as equivalent mass of

glycogen. Lipids perform various and different functions in living organisms. They naturally

occur in most plants, animals, microorganisms and are used as cell membrane components,

energy storage molecules, insulation, and hormones etc.

Functions of Lipids

It is established that lipids play extremely important roles in the normal functions of a cell. Not

only do lipids serve as highly reduced storage forms of energy, but they also play an intimate

role in the structure of cell membrane and organellar membranes.  Lipids perform many

functions, such as:

1. Lipids either in dietary, stored or newly synthesized form can serve as efficient source of

energy. For instance, complete oxidation of 1 gram of triacylglycerol (the principal storage form
of lipids) produces 37-38kj of energy whereas I gram of protein or carbohydrate on complete

oxidation will produce 16-17 gram of energy.

2. Lipids serve as thermal insulators in the subcutaneous tissues and around certain organs.They

preserve heat in the body and thus prevent excessive heat loss

3. Lipids function as padding materials to protect certain delicate organs against physical

exertion or injury

4. Lipids facilitate the transport of fat soluble vitamins such as vitamins A, D, E, and K (ADEK)

5. Lipids due to their relatively low density aid buoyancy in aquatic organisms such as wales and

sharks. They help them to easily swim and stay above water.

6. Lipids such as waxes due to their repellant hydrophobic nature are important components of

furs, feathers and other protective layers that help to keep aquatic birds and mammals dry

7. Lipids are also the building blocks of many hormones and are an important constituent of all

cellular membranes.

8. Lipids in form of phospholipid bilayer are the basic structural unit of all biological membranes

9. Some lipids highly specialized functions such as regulation of metabolic processes. For

instance steroid hormones which are composed of steroid lipids help to regulate blood pressure

while eicosanoids (derived lipids) are known to regulate body temperature. Also gangliosides

and cerebrosides which are located on the cell surface membrane participate in cell signal

communication or cellular recognition (function as recognition site).

10. Lipids act as the structural component of the body and provide the hydrophobic barrier that

permits partitioning of the aqueous contents of the cell and subcellular structures.

11. Lipids also act as activators of certain enzymes. For instance, enzymes such as glucose-6-

phosphatase, stearyl CoA desaturase, ω-monooxygenase, and β-hydroxybutyric dehydrogenase

require phosphatidylcholine micelles for activation.

Fatty acids as the basic components of lipids

Fatty acids are the basic components of lipids. They rarely occur as free molecules (unesterified)

in nature but are usually found as components of many complex lipid molecules. They are

esterified or combined with different alcohols and sometimes with other groups to form lipids.

By definition, fatty acids are molecules with long hydrocarbon chain which is hydrophobic and a

terminal carboxylic head which is hydrophilic. They have the general formulae RCOOH which

alternatively can be written as

Where R represents the long hydrocarbon chain and COOH (carboxyl group) serves as the

functional group. Due to the carboxyl group present in fatty acid, they are regarded as carboxylic

acids. Fatty acids can also exist in unesterified form as free fatty acids (FFA). However, the

concentration of the free fatty acids in cell must be kept low. This is because high concentration

of FFA disrupts the cell membrane and cause the cell to lose both its structural and functional

integrity.

The part of a fatty acid that does not include the hydroxyl (OH) group is called an acyl group.

Fatty acids may exist in ionized form (RCOO-) or unionized form (RCOOH). Fatty acids have a
Pka range of 4.5-5.0 and hence, under physiological conditions in water, they usually exist in the

ionized form, meaning that the carboxylic group loses a hydrogen ion (H+) to form a negatively

charged carboxylate group (COO−).

Fatty acids are principally stored as triacylglycerol in the adipose tissues. Most biological fatty

acids contain an even number of carbon atoms because the biosynthetic pathway common to all

organisms involves chemically linking two-carbon units together (however, relatively small

amounts of odd-number fatty acids do occur in some organisms, especially marine or aquatic

organism).

Types of fatty acids

Fatty acids can be classified on different basis. Firstly, on the basis of length or number of

carbon atoms, they can be classified as (i) long chain fatty acids (ii) medium chain fatty acid (iii)

short chain fatty acids. More commonly fatty acids are classified on the basis of the presence or

absence of carbon-carbon double bond (C═C) in the hydrocarbon chain as

(i) Saturated fatty acids (ii) Unsaturated fatty acids

Saturated fatty acids

Saturated fatty acids are fatty acids which do not contain a carbon-carbon double bond in their

hydrocarbon chain. The term saturated indicates that the maximum possible number of hydrogen

atoms is bonded to each carbon in the molecule. Many saturated fatty acids have a trivial or

common name as well as a chemically descriptive systematic name. The systematic names are

based on numbering the carbon atoms, beginning with the acidic carbon. Common examples of

saturated fatty acids are palmitic acid (C16) and stearic acid (C18). Other examples are shown in
the table below gives the names and typical biological sources of the most common saturated

fatty acids.

Common saturated fatty acids

trivial name systematic name number of carbons in typical sources
chain
lauric acid n-dodecanoic acid 12 palm kernel oil, nutmeg
myristic acid n-tetradecanoic acid 14 palm kernel oil, nutmeg
palmitic acid n-hexadecanoic 16 olive oil, animal lipids
acid
stearic acid n-octadecanoic acid 18 cocoa butter, animal lipids
Arachidic acid Eicosanoic acid 20
behenic acid n-docosanoic acid 22 brain tissue, radish oil
lignoceric acid n-tetracosanoic acid 24 brain tissue, carnauba wax

Unsaturated fatty acids
Unsaturated fatty acids are fatty acids that contain one or more carbon-carbon double bonds in
their hydrocarbon chain. The term unsaturated indicates that fewer than the maximum possible
number of hydrogen atoms is bonded to some of the carbon atoms in the molecule. Based on the
number of double bonds present, unsaturated fatty acids may be sub classified into—
monounsaturated or polyunsaturated fatty acids. Monounsaturated fatty acids are unsaturated
fatty acids with one double bond while polyunsaturated fatty acids are unsaturated fatty acids
with two or more double bonds.
Common examples of unsaturated fatty acid are oleic acid, linoleic acid and linolenic acid. Other
common examples of unsaturated fatty acids are shown in the table below.

Common unsaturated fatty acids

common name
systematic name
number of carbons in chain
typical sources
palmitoleic acid
cis-9-hexadecenoic acid
16
marine algae, pine oil
oleic acid
cis-9-octadecenoic acid
18
animal tissues, olive oil

linoleic acid
cis-9-, cis-12-octadecadienoic acid
18
corn oil, animal tissues, bacteria

linolenic acid
cis-9-, cis-12-, cis-15-octadecatrienoic acid
18
animal tissues

arachidonic acid
5,8,11,14-eicosatetraenoic acid
20
liver, brain tissue

Palmitic acid

Linoleic acid (polyunsaturated acid)

Wavy or ziz-zag structures

 Oleic acid

Properties of lipids

 Lipids may be either liquids or non-crystalline solids at room temperature.

 Pure fats and oils are colorless, odorless, and tasteless.

 They are energy-rich organic molecules

 Lipids are insoluble in water

 Lipids are soluble in organic solvents like alcohol, chloroform, acetone, benzene, etc.

 Solid triglycerols (Fats) have high proportions of saturated fatty acids.

 Liquid triglycerols (Oils) have high proportions of unsaturated fatty acids.

 Lipids, especially phospholipids are amphipathic in nature. Lipids generally possess

regions which attract water and regions that repel water. These two regions are known as

hydrophilic and hydrophobic regions respectively. Both regions describe the amphipathic

nature of lipids

Chemical Reactions of lipids

Lipids undergo some chemical reactions which include the following:

1. Hydrolysis of lipids

Hydrolysis refers to the breakdown of lipid molecules particularly in form of triacylglycerol

(triglyceriedes) into the fatty acids and alcohol components. Hydrolysis may involve the use of

alkali (alkaline hydrolysis) or enzyme (enzyme hydrolysis) to facilitate the process. Alkaline

hydrolysis is termed saponification because one of the products of the hydrolysis is soap.

A glycerol molecule is made up of three carbon atoms with a hydroxyl group attached to it and

hydrogen atoms occupying the remaining positions. Fatty acids consist of an acid group at one

end of the molecule and a hydrocarbon chain, which is usually denoted by the letter ‘R’.
2. Saponification:

Saponification is a process by which lipids in form of triglyceriedes react with an alkali (sodium

hydroxide or potassium hydroxide) to produce glycerol and a fatty acid salt known as soap. The

triglycerides used in saponification process are mostly animal fats or vegetable oils. When

sodium hydroxide is used, a hard soap is produced whereas the use of potassium hydroxide

produces a soft soap. Lipids can be characterized by their saponification number (acid value)

which is defined as the amount of potassium hydroxide (KOH) in milligram (mg) required to

completely neutralize one gram of the lipid.

Saponification number is a property of a lipid which measures the average molecular size of the

fatty acids present in the lipid. The higher the saponification number of a lipid, the shorter the

fatty acid present in the lipid

3. Hydrogenation

The carbon-carbon double bonds in unsaturated fatty acids can be hydrogenated by reacting with

hydrogen to produce saturated fatty acids.

4. Halogenation

Unsaturated fatty acids, whether they are free or combined as esters in fats and oils, react with

halogens by addition at the double bond(s). The reaction results in the decolorization of the

halogen solution. The most common form of halogenation is Iodination,. The number of grams

of iodine that combine with 100 gram of lipid (fat) is referred to iodine number. It shows how

unsaturated a lipid is. High iodine number indicates high degree of unsaturation

5. Rancidity:
The term rancidity refers to the process whereby lipids (fats or oils) develop a characteristic taste

and due to exposure to moist air. It occurs as result of hydrolysis and oxidation of the lipids into

aldehydes or ketones. Lipids that are less prone to rancidity are better and preferred nutritionally.

Classification (Types) of lipids

Lipids can be classified according to their hydrolysis products and according to similarities in

their molecular structures. Three major classes are as follows: Simple lipids, Complex lipids and

Derived lipids

1. Simple lipids

Simple lipids are esters of fatty acids and alcohols. The common examples are (a) acylglycerols

which yield fatty acids and glycerol upon hydrolysis and (b) Waxes which yield fatty acids and

long-chain, high molecular weight alcohols upon hydrolysis.

(a) Acylglycerol: Acylglycerols are esters of fatty acids and alcohols and are the most common

examples of simple lipids. Acylglycerols are also known as glycerides. In these lipids, the fatty

acids components are joined to the glycerol backbone through the process of esterification (ester

bond formation). The esterification of fatty acids and glycerol is a condensational process which

involves elimination of water molecules (s). Three molecule of water (3H 2O) is released when

three fatty acid molecule are involved..

Similarly, esterification involving one and two fatty acids produces one and two water molecules

(H2O and 2H2O) respectively. Depending on the number of fatty acids joined or esterified to the

glycerol backbone, there are three types of acylglycerols.

i. Monoacylglycerols (MAG) which is also known as monoglycerides. Monoacylglycerols

have one fatty acid molecule joined or esterified to glycerol either at carbon 1 or 2. The fatty

acid may be saturated or unsaturated

Monoglyceride

ii. Diacylglycerol (DAG) which are also known as diglycerides have two fatty acid molecules

joined or esterified to glycerol at carbon positions 1 and 2. The fatty acids may be the same or

different, saturated or unsaturated

Diglyceride
iii. Triacylglycerols (TAG)

Triacylglycerols which are also known as triglycerides have three fatty acid molecules joined or

esterified to glycerol at carbon positions 1, 2 and 3. The fatty acids may be the same or different,

saturated or unsaturated. They are usually found in adipose tissues. Triacylglycerol is the

principal neutral derivative and the main energy store in animals. Triacylglycerol or triglyceride,

when oxidized produces energy in amount that is twice what carbohydrate or protein produces.

For instance, complete oxidation of 1g of TAG produces 38kj of energy compared to the 17kj of

energy produced by 1g of carbohydrate or protein when oxidized. Thus TAG is an efficient

energy store in animals. Some properties that TAG an efficient energy store include:

 Triacylglycerol is anhydrous and less dense. Hence, large amount of it can be stored in a

a relatively small space.

 Triacylglycerol contain large number of highly reduced carbon atoms which when

oxidized produces large amount of energy and water.

The physical properties of the triacylglycerol are determined by the specific fatty acids

esterified to the glycerol moiety and the actual position the fatty acids occupy.

Structure of Triglycerides
 Triglyceride

 Triglycerides are lipids consisting of one glycerol molecule bonded with three fatty acid

molecules.

 The bonds between the molecules are covalent and are called Ester bonds.

 The bonds are formed through condensation reaction (elimination of water molecule).

 The charges are evenly distributed around the molecule, hence, do not have net charge

and find it difficult to form hydrogen bonds with water molecules, making them insoluble in

water

Formation of triglyceride

(b) Waxes
Waxes are simple lipids or esters of long-chain fatty acid and high molecular weight monohydric

alcohol. Although they are a minor component of biological systems, they are neutral lipids of

physiological importance. Waxes have a weakly polar head group (ester moiety) and a long,

nonpolar tail (hydrophobic chain). They are completely water-insoluble and generally solid at

biological temperatures. The fatty acids found in waxes are usually saturated while the alcohols

may be saturated or unsaturated and may include sterols such as cholesterol.

Their strongly hydrophobic nature allows them to confer water repellent characteristics to animal

skin, to the leaves of plants, bird feathers, and to the cuticles of certain insects. They are also

responsible for the glossy nature of fruits like apples. Waxes also serve as energy-storage

substances in plankton (microscopic aquatic plants and animals) and in higher members of the

aquatic food chain. Plankton apparently uses the biosynthesis of waxes to adjust their buoyant

density and thus their depth in the ocean. Whales and many fishes also store large quantities of

waxes. A very common example of waxes is the Bee wax which is chemically known as

Myricyl palmitate. It is composed of palmitic acid (CH 3(CH2)14COOH) and myricyl alcohol

(C30H61OH)

CH3 (CH2)14COOH + C30H61OH → CH3(CH2)14COO C30H61 + H2O

Palmitic acid myricyl alcohol Myricyl palmitate Water

Waxes are useful in several other areas. The carnauba wax obtained from the fronds of a species

of palm tree in Brazil is a notable hard wax used for high gloss polishes such as in automobile

wax, boat wax, floor wax and shoe wax. Lanolin, a component of wool wax is utilize as a base in

pharmaceutical and cosmetic companies in manufacturing of their products because it is rapidly

assimilated by the human skin

2. Complex or compound lipids

These are esters of fatty acids and alcohol containing an additional group. They are broadly sub-

classified into phospholipids and glycolipids

(a)Phospholipids are complex lipids which contain a phosphate group in addition to fatty acids

and alcohol. Depending the alcohol backbone present (glycerol or sphingosine), phospholipuids

may be glycerophospholipids (glycerol backbone) and sphingophospholipids (sphingosine

backbone).

Glycerophospholipids are phospholipids with glycerol as their alcohol backbone. They are also

known as phosphoglycerides and normally contain two fatty acid molecules attached through

ester bonds to C1 and C2 of the glycerol molecule. A phosphate molecule is attached to the

hydroxyl group of C3 and a nitrogen-containing polar compound (such as choline, ethanoamine,

serine, glycerol and inositol) is attached to the phosphate molecule.

 or

R3 or X= Nitrogen-containing polar compound

Specific examples of phosphoglycerides include

1. phosphatidylcholine (Choline--CH2CH2N+(CH3)3

Phosphatidylcholine is commonly known as lecithin and acts as a store of choline which

combines with acetyl molecule to form acetylcholine, a compound which is important in

transmission of chemical signals through the synapse or synaptic gap in nerve impulse

transmission.
2.Phosphatidylethanoamine (Ethanoamine--CH2CH2N+H3)

Phosphatidylethanoamine also known as cephaline is the major phospholipid in E.coli

1. Phosphatidylglycerol (Glycerol--CH2CHOHCH2OH)

Phosphatidylglycerol are the most abundant class of lipids and are very common in the

plasma membrane
4. Phosphatidylinositol

Phosphatidylinositol is a precursor of second messengers, For instance, phosphatidylinositol 1, 4,

5 biphosphate is an essential component of the cell membrane. When stimulated by a hormone

messenger or agonist, it cleaves into diaclyglycerol and inositol 1, 4, 5 triphosphate which act as

second messengers in signal transduction

2. Phosphatidylserine (Serine—CH2CHCOOHNH3+)

Phosphatidylserine is the major phospholipid in most membranes

6. Diphosphatidylglycerol

These are also known as cardilipins

Cardiolipin

The simplest glycerophospholipid is a phosphatidate or phosphatidic acid (containing H atom in

place of a nitrogen-containing polar compound. It is the precursor for other phosphatidates or

phosphoglycerides

Phosphaticdic acid

Plasmalogens

There are other forms of glycerophospholipids known as plasmalogens. The plasminogens are a

class of glycerophospholipids which contain a vinyl-ether and an ester bond at

the C1 and C2 positions, respectively, in the glycerol backbone. They constitute 10 % of the total
mass of phospholipids in humans, mainly as membrane structure components. They differ from

other phosphoglycerides or phosphatidates discussed above in that the fatty acid moiety liked to

C1 of the glycerol molecule is through vinyl ether bond and not ester bond. They are mist

abundant in brain and muscle membranes

X= Choline or ethanoamine

They usually contain choline or ethanolamine group and are abundant in the brain

Sphingophospholipids

Sphingophospholipids are a class of phospholipids that have sphingosine as their alcohol

component or backbone instead of glycerol. Sphingosine is an amino alcohol with 18 carbon

atoms. It has hydroxyl groups attached to the first (C 1) and third carbon (C3), an amino group is

attached to C2 and a double bond between C4 and C5

The sphingomyelins are the most common examples of glycosphingolipids. They are formed

form a ceramide. A ceramide is formed by attaching a fatty acid to amino group (NH 2) of

sphingosine through amide bond. Sphingomyelin is then completely formed by attaching a

phosphate group to the hydroxyl group of carbon 1 (C 1), and a choline molecule is then attached

to the phosphate group.

 Sphingomyelin

(b) Glycolipids

Glycolipids are a class of complex lipids that contain carbohydrate molecule in addition to their

fatty acids and alcohol components. Glycolipids are essential in providing stability of the plasma

membrane. Furthermore, they are also associated with cell to cell interactions, e.g. cell adhesion

to form a tissue. They also facilitate cellular recognition, which is important in immunologic

functions. Human blood types (A, B, AB, O) are based on the glycolipids on the surface

of erythrocytes. The oligosaccharide component of the glycolipid determines the blood group

antigen. For example, blood type A has N-acetylgalactosamine, blood type B has a galactose.

Blood type AB has both antigens whereas blood type O lacks these antigens.

Glycolipids may be glyceroglycolipids or sphingoglycolipid  depending on the alcohol group

present (glycerol or sphingosine). This is why they yield fatty acids, sphingosine or glycerol, and

a carbohydrate upon hydrolysis. Common examples of glycolipids are cerebrosides and

gangliosides
Glyceroglycolipids

Glyceroglycolipids are a class of glycolipids composed of a carbohydrate component, glycerol

backbone and at least one fatty acid. Examples includes galactolpids and sulpholipids

Glycosphingolipids

Glycosphingolipids or phingoglycolipids are a class of glycolipids composed of a carbohydrate

and a sphingolipid linked together by a glycosidic bond. Thus, hydrolysis of the

glycosphingolipid yields sugar, fatty acid, and sphingosine (or dihydrospingosine). They occur

largely in the outer face of plasmamembrane. They have head groups with one or more sugar

units connected directly to the hydroxyl group at C 2 of the ceramide moiety. They do not contain

phosphate Glycosphingolipids are part of the cell membrane and are involved in cell-cell

interactions. Common examples of glycosphingolipids are  cerebrosides, and gangliosides.

Others include globosides, and glycophosphosphingolipids.

Cerebrosides

Cerebrosides are the simplest glycosphingolipids which are composed of a monosaccharide

(galactose or glucose) or an oligosaccharide linked glycosidically to the terminal OH group of

ceramide. They have a sphingosine core and are found in the cell membranes of the neurons and

the muscle cells. Hydrolysis of a cerebroside yields sphingosine, sugar unit (e.g. galactose or

glucose), and fatty acid. The carbohydrate constituent of the cerebroside extends on the outside

of the cell membrane. It, thus, plays a part in cell to cell interactions and cell recognition. Based

on the carbohydrate constituent, the cerebrosides may be classified as galactocerebroside or

glucocerebroside.
Galactocerebroside

Galactocerebroside (also called galactosylceramide) is a cerebroside in which the carbohydrate

constituent is galactose. It is found usually in neural tissues and the main glycosphingolipid in

the brain. Galactocerebroside that is sulfated is referred to as sulfatide. Sulfatides play a role in

immune response and nervous system signaling

Glucocerebroside

Glucocerebroside (also known as glucosylceramide) is a cerebroside in which the carbohydrate

constituent is glucose. The latter is often found in non-neural tissues. In skin, it plays a part in

enabling water permeability barrier function of the skin.

Gangliosides

Gangliosides are a class of glycosphingolipid  composed of ceramide and oligosaccharide, with

one or more sialic acids (e.g. n-acetylneuraminic acid, NeuNAc) linked to the sugar chain. They

are the most complex glycosphingolipids NeuNAc constitutes the head groups of gangliosides. It

as a surface marker that helps in cellular recognition and cell-to-cell communication.

Ganglioside
3. Derived lipids:

Derived lipids are hydrolysis product of simple and compound. They include fatty acid, glycerol,

sphingosine and steroid derivatives et

Lipid structures in aqueous medium

Lipids are capable of forming various structures in aqueous medium. Such structures include
phosphplipid bilayer, liposomes and micelles

Phosphplipid bilayer
The phospholipid bilayer is a thin polar membrane made of two layers of lipid molecules. These
membranes are flat sheets that form a continuous barrier around all cells. They form the basic
structural unit of all biological membrane. The phosphate heads extends into the aqueous
medium while the hydrophobic tails move away from the aqueous compartments to form the
hydrophobic core.
Liposomes
Liposomes are spherical-shaped vesicle of one or more lipid bilayers that encloses a discrete
aqueous compartment. They are generally used as vehicles for drug or gene delivery. The unique
ability of liposomes to entrap both lipophilic and hydrophilic compounds enables a diverse range
of drugs to be encapsulated by these vesicles. Hydrophobic molecules are inserted into the
bilayer membrane, and hydrophilic molecules can be entrapped in the aqueous center

Micelles
Micelles are closed lipid monolayers with a fatty acid core and polar surface, or polar core with
fatty acids on the surface (inverted micelle). Micelles are lipid molecules that arrange themselves
in a spherical form in aqueous solutions. The formation of a micelle is a response to the
amphipathic nature of fatty acids, meaning that they contain both hydrophilic regions (polar head
groups) as well as hydrophobic regions (the long hydrophobic chain). Micelles contain polar
head groups that usually form the outside as the surface of micelles. They face to the water
because they are polar. The hydrophobic tails are inside and away from the water since they are
nonpolar. Fatty acids from micelles usually have a single hydrocarbon chain as opposed to two
hydrocarbon tails. This allows them to conform into a spherical shape for lesser steric hindrance
within a fatty acid. Fatty acids from Glycolipids and phospholipids, on the other hand, have two
hydrophobic chains that are too bulky to fit into the spherical shape as micelles do. Thus, they
preferred to form glycolipids and phospholipids as "lipid bilayers",