THE LIPIDS

WHAT ARE LIPIDS?

 A family of compounds that includes

– Triglycerides (fats & oils)
 Fats: lipids that are solid at room temperature
 Oils: lipids that are liquid at room temperature
– Phospholipids
– Sterols (cholesterol)

I. A PRIMER ON FATS

A. The Functions of Fat in the Body

 Energy source esp. for muscles
 Serves as an energy reserve
- 1# body fat contains 3500 kcal
- 30-50# of stored fat
 Major component of cell membranes
 Nourishes skin & hair
 Insulates the body from temperature extremes
 Cushion the vital organs to protect them from shock

B. The Functions of Fat in Food

 Provide calories (9 per gram)

 Provide satiety
 Carry fat-soluble vitamins & essential fatty acids
 Contribute aroma & flavor
LIPID TERMINOLOGY

 Triglycerides: the major class of dietary lipids, including fats & oils

– Made up of 3 units known as fatty acids and 1 unit called glycerol (backbone)

– Comprise about 95% of lipids in food and the human body

Triglyceride or triacylglycerol may be:

 Simple – a triester formed from the esterification of glycerol with 3 identical fatty acid
molecules
 Mixed – a trimester formed from the esterification of glycerol with more than one kind of
fatty acid molecule
Most biochemically important triacylglycerols are mixed triacylglycerols

 Phospholipids:

– 2nd of three main classes of lipids

– similar to a triglyceride, but contains phosphorous

 Sterols

– 3rd of three main classes of lipids;

– Cholesterol

 one of the sterols

 manufactured in the body for a variety of purposes

 Fatty acids:

– basic units of fat composed of chains of carbon atoms

– an acid group at one end and hydrogen atoms attached all along their length
 II. A CLOSER VIEW OF FATS

A. Chain Length - number of carbons linked together

 Shorter = more soluble in water

B. Saturated vs. Unsaturated - number of hydrogens the chain is holding

 Maximum = saturated
 Unsaturated = one or more is missing
 Point of unsaturation = site where hydrogen is missing

SAMPLE NOMENCLATURE FOR FATTY ACIDS:

Name - Carbon Length: Number of Double Bonds

(position of double bond)
Butyric acid - 4:0
Palmitic acid - 16:0
Stearic acid – 18:0
Oleic acid - 18:1 (9)
Linoleic acid - 18:2 (9, 12)
Linolenic acid - 18:3 (9, 12, 15)
Arachidonic acid - 20:4 (5, 8, 11, 14)
Eicosapentaenoic acid - 20:5 (5, 8, 11, 14, 17)
Docosahexaenoic acid - 22:6 (4, 7, 10, 13, 16, 19)

 Saturated fatty acid: a fatty acid carrying the maximum possible number of hydrogen atoms

– Animal foods such as meat, poultry and full-fat dairy products

– Tropical oils such as palm and coconut

  Unsaturated fatty acid: a fatty acid with one or more points of unsaturation.

– Found in foods from both plants & animal sources

 Monounsaturated fatty acids (one double bond)

 Polyunsaturated fatty acids (two or more)

 Monounsaturated fatty acid: also called a MUFA; a fatty acid containing one point of unsaturation

– Found mostly in vegetable oils such as olive, canola & peanut

 Polyunsaturated fatty acids: also called a PUFA; a fatty acid in which two or more point of
unsaturation occur

– Found in nuts, vegetable oils such as safflower, sunflower and soybean, and in fatty fish

ESSENTIAL FATTY ACIDS

 The body can synthesize all of the fatty acids it needs from carbohydrates, fat or protein except for:

1. Omega 6 - linoleic and arachidonic acids

2. Omega 3 - linolenic, eicosapentaenoic, and docosahexaenoic acids

Omega-3 and Omega-6

 Essential fatty acids are especially important for making prostaglandins in your
body.
 Prostaglandins are hormone-like substances that regulate many activities in your
body including inflammation, pain, and swelling (some cause swelling and others
relieve it).
 They also play a role in controlling your blood pressure, your heart, your kidneys,
your digestive system, and body temperature.
 They are important for allergic reactions, blood clotting and making other
hormones.
 Omega - 6 versus Omega – 3

 Omega – 6
- Linoleic

 Omega – 3
- Linolenic
- Cold water fish
- Help dissolve blood clots
- Lower blood pressure
- Dilate the arteries

CHARACTERISTICS OF FATS IN FOODS

A. Liquid vs. Solid

 More saturated a fat is, the more solid it is at room temperature

 More unsaturated a fat is, the more liquid it is at room temperature

B. Hydrogenation
 The process of adding hydrogen to unsaturated fat to make it more solid and more resistant to
chemical changes such as spoiling

 Increasing a fat’s saturation can cause a fat to lose its unsaturated health benefits
TRANS-FATTY ACIDS

 Formed when margarine is processed

 Hydrogen molecules are on opposite sides of point of unsaturation

 “Partially hydrogenated vegetable oil”

 Link between trans fatty acids and heart disease

PHYSICAL PROPERTIES OF FATTY ACIDS

MELTING POINTS OF FATTY ACIDS AND THE COMPLEX LIPIDS THAT CONTAIN THEM

Melting points of fatty acids increase with increasing size. Melting points of unsaturated fatty acids
(those with double bonds) are lower than saturated fatty acids of the same size.
 Complex lipids that contain mainly unsaturated fatty acids are liquids at room temperature.

PHYSICAL PROPERTIES

 Oils are liquids at room temperature because they contain a large proportion of unsaturated fatty acids.
Both fats and oils are insoluble in water

 Tristearin (a fat) contains only saturated fatty acids (stearic acid) and would be a solid at room
temperature.

TRIGLYCERIDE REACTIONS

 These reactions are identical to those studied in carboxylic acids

 Triglycerides undergo three basic reactions

Triglyceride
+
H O, H H , Ni
2
2

Glycerol NaOH
Fatty Acids More saturated
triglyceride
Glycerol
Fatty Acid Salts

COMPLEX LIPIDS: MEMBRANES

• Some polar complex lipids are structural components of cell membranes.

• Phospholipids are the most common membrane lipids. Many are phosphoacylglycerols (structurally
related to triacylglycerols).

• The most abundant phospholipid is lecithin (phosphatidylcholine).

 • Sphingolipids contain sphingosine, a fatty acid, and one or more other molecules. The two major types
are sphingomyelin and cerebrosides.

PHOSPHOLIPIDS

Fatty Acid
G
l Fatty Acid Phosphoacylglycerols,
y
c like soaps, contain both a
e polar (the head) and a
Phosphoric Acid
r
o nonpolar region (the tail)
l
Amine

 A lipid consisting of a water-soluble head and a fat-soluble tail

 Contain phosphorous
 Component of cell membranes
 Serve as emulsifiers (allow fats and water to mix and travel in and out of cells into watery fluid
on both sides)
 A phospholipid is composed of two fatty acids, a glycerol unit, a phosphate group and a polar
molecule.
 Lecithin is a common phospholipid
- Often used as an emulsifier in foods such as margarine, chocolate & salad
dressings
SOME PHOSPHOGLYCERIDES

SPHINGOLIPIDS

• Based on sphingosine

– Long-chain

– Nitrogen-containing

– Alcohol

• Amphipathic, like phospholipids

– Polar head group

– Two nonpolar fatty acid tail

• Structural component of cellular membranes

• Major categories

– Sphingomyelins

– Glycosphingolipids
SIMPLE LIPIDS: STEROIDS

 Simple lipids (unlike complex lipids such as triacylglycerols) do not contain fatty acids linked
by ester bonds.
 Simple lipids include:
 Steroids
 Prostaglandins
 Leukotrienes

 Steroids are simple lipids that contain the fused-ring system commonly called the steroid
nucleus.

 Cholesterol is the most abundant steroid in animals. Many other steroids are synthesized from it.

CHOLESTEROL – A STEROL

 Found only in animal products

 Also made & used in the body:

– Structure of cell membranes

– Used to make bile for digestion

 Bile: a mixture of compounds, made by the liver, stored in the gallbladder, & secreted
into the small intestine
  Emulsifies lipids to prepare them for enzymatic digestion & helps transport them into the
intestinal wall cells

HORMONES

 Biochemical substance, produced by a ductless gland that has a messenger function.

- Serves as a means of communication between various tissues.

TWO MAJOR CLASSES OF STEROID HORMONES

1. Sex hormones

2. Adrenocorticoid hormones

STEROIDS: HUMAN SEX HORMONES

TWO TYPES OF ADRENOCORTICOID HORMONES

1. Mineralcorticoids – control the balance of Na+ and K+ in the cells and body fluids

2. Glucocorticoids – control glucose metabolism and counteract inflammation

STEROIDS: BILE SALTS

 
Bile salts play a role in digestion. They are synthesized form cholesterol in the liver and stored in
the gallbladder.
 During digestion, bile salts break down (emulsify) nonpolar fat globules, aiding in digestion and
absorption of dietary lipids. Bile salts have one polar and one nonpolar face
PROSTAGLANDINS AND LEUKOTRIENES

 Prostaglandins
 are synthesized from polyunsaturated fatty acids. They have a role in the
physiology of fever and pain. Aspirin interferes with the body’s ability to
synthesize prostaglandins.
 Leukotrienes
 play a role in allergic and inflammation responses. They were originally isolated
from leukocytes.

MEMBRANES AND RELATED STRUCTURES

 Micelles are spherical structures that have a nonpolar, hydrophobic environment in the core, and
a polar, aqueous environment on the surface. The bile salt-lipid complexes formed in the small
intestine are micelles.

BILAYERS AND LIPOSOMES

 Bilayers
 consist of polar lipids that have their nonpolar regions facing together, and their
polar-head groups facing out into the aqueous solution.
 Liposomes
 are spherical structures that are bilayers folded around a core of water.
FLUID MOSAIC MODEL OF MEMBRANES

 Protein and lipid molecules are free to diffuse around in the membrane because only weak,
noncovalent bonding holds them in the membrane.

TRANSPORT ACROSS MEMBRANES


Membranes are selectively permeable barriers that restrict the movement of many ions and
molecules. Nonpolar molecules cross by simple diffusion.
 In facilitated diffusion, proteins act as polar channels that allow ions or polar molecules to pass
through the membrane without the expenditure of cellular energy.
ACTIVE TRANSPORT

• Some movements across a membrane are “uphill,” or against the concentration gradient

• This process is active transport

– Requires energy

– Consider Na+-K+ ATPase

– Uses ATP hydrolysis to maintain the Na+-K+ gradient needed in the cell
WAXES: PROTECTIVE COATING LIPIDS

- Esters of an alcohol other than glycerol (long chain alcohol, sterol, hydroxycarotenoids, vitamin
A) and a long chain fatty acid (wax esters).

WAXES

 A polar lipids forming a protective coating (cutin in the cuticle) on plant leaves and fruits
- in animals (wax of honeybee, cuticular lipids of insects, spermaceti of the sperm whale,
skin lipids, uropygial glands of birds, depot fat of planktonic crustacea), algae, fungi and
bacteria.
 Wax esters are saponified by hot alkaline solutions and give a fatty acid and an alcohol.
 They are soluble in aromatic solvents, chloroform, ethers, esters and ketones.
USES

 Carnauba wax- a hard wax whose uses involve high finishes: automobile wax, boat wax, floor
wax, and shoe wax
 Lanolin – a mixture of waxes obtained from sheep wool, used as gloss base for skin creams and
ointments intended to enhance retention of water (softens the skin)
 Wax is a pliable, water-repelling substance used particularly in protecting surfaces and
producing polished surfaces
 Mineral wax(paraffin) –mixture of long chain alkanes obtained from the processing of
petroleum

LIPOPROTEINS IN BLOOD

• Lipoproteins are complexes of lipids and proteins.

• Lipoproteins transport lipids in blood.

• Low-density lipoproteins (LDLs) transport cholesterol and other lipids from the liver to the cells of the
body.

• High-density lipoproteins (HDLs) transport cholesterol from body cells back to the liver.

• High ratios of LDL to HDL have been correlated with cardiovascular disease.

• For this reason, LDL is sometimes referred to as bad cholesterol and HDL as good cholesterol.
LOWERING BLOOD CHOLESTEROL LEVELS

 Eat no more than 30% of calories from fat

 Eat no more than 8-10% of calories from saturated fat
 Eat no more than 10% of calories from PUFAs
 MUFAs should make up 10-15% of total calories
 Limit daily cholesterol intake to no more than 300 milligrams
FAT IN THE DIET

A. Food Guide Pyramid

 3 groups traditionally account for nine-tenths of the fat in the U.S. diet
 Fats, oils & sweets group
 Meat, poultry, fish, dry beans, eggs & nut group
 Milk, yogurt & cheese group
 Most of the fat in our diets comes from animal products

B. Fat Substitutes

 Carbohydrate-based
 Help retain moisture to maintain the juiciness or creaminess that is lost with fat reduction
 Carrageenan, fruit purees, gelatin, gums, starches & products made from fiber
  Protein-based
 Proteins are cooked & blended to form tiny round particles that trap water to maintain the
mouth feel of fat
 Whey protein concentrate (Dairy-Lo), or milk & egg white protein (Simplesse)
 Fat-based
 Are either only partially digestible or completely undigestible to prevent absorption of fat
 Caprenin (substitute for cocoa butter in candy), Salatrim (found in low fat baking chips),
and olestra (often found in fat free potato chips)

C. At the Grocery Store

 Read labels to determine both the amounts & types of fat contained in foods

D. In the Kitchen

 Use canola & olive oil for baking & cooking

 Prepare lean cuts of meat
 Bake, broil & steam instead of frying
 Use low-fat or fat-free dairy products & dressings
 Season with herbs & spices rather than with fats
 Incorporate plant-based protein sources such as soy & legumes

E. At the Table

 Eat more fresh fruits & vegetables

 Use jam instead of butter
 Limit use of high-fat condiments including mayo, butter & sour cream or use low-fat varieties
 Use mostly monounsaturated vegetable oils such as olive or canola
 Eat fewer high-fat desserts

F. Recipe Modification
 Egg whites
 Fat-free evaporated milk
 Fat-free sour cream
 Fruit purees
 Fat-free cream cheese
 Oils

G. Diet & Heart Disease

Risk Factors
 High cholesterol
 High blood pressure
 Smoking
 Diabetes
 Lack of exercise
 Stress
 Obesity
 Unhealthy diet
 Age
 Gender
 Genetics

 Ways to Reduce Risk

 Limit intake of cholesterol & saturated fat
 Quit smoking
 Maintain a healthy weight
 Eat high fiber foods
 Increase physical activity
 Increase fruit & vegetable consumption
 Limit alcohol consumption