Function5 classes / types

Lipids

Lipid Function

1. Long-term energy storage (fat)2. Form cell membrane (phospholipids)3. Messaging (hormones)4. Insulation5. Cushioning of Internal Organs

Lipid Function

Why are lipids well suited for long term energy storage?

Contain many high energy bonds between carbon and hydrogen

Contain twice as much energy per gram than carbohydrates (very concentrated)

Thus a much more compact form of storage than carbohydrate

Animals store fats in adipose cells

Types of Lipid

1. Fat: Triglyceride / triacylglycerol2. Phospholipid3. Steroid4. Wax5. Carotenoid

1. Fat Structure

also known as triglyceride or triacylglycerol

Consists of: 1 glycerol

backbone 3 fatty acid chains

Fatty acid

Glycerol Fatty acid

Fatty acid

Fatty acid

Glycerol Fatty acid

Fatty acid

Glycerol Structure

Basic structure: 3 carbon molecule each carbon has a

hydroxyl group attached

the alcohols are sites for condensation reactions

Fatty acid structure

Basic structure: Unbranched chain of

carbons A carboxyl group at one

end Fatty acid chains can

differ from each other in two ways: Length of carbon chain: 4-

24 Saturation (number of

double bonds)- Saturated- Monounsaturated- polyunsaturated

Essential Fatty Acids

The most common fatty acid in living organisms is palmitic acid. Humans can synthesize and use palmitic acid:

CH3(CH2)14CO2H

or

Essential Fatty Acids

Essential fatty acids are those that humans can not synthesis and must ingest.

Humans can not create double bonds in fatty acids beyond C10.

1) alpha-Linolenic Acid (an omega-3 fatty acid)

Essential Fatty Acids

2) Linoleic Acid (an omega-6 fatty acid)

Properties of Fatty acids

Type Saturated UnsaturatedStructure Single

bondsDouble bonds, kink

State at r.t.

Solid liquid

Origin Animals Plants

Examples Butter, lard Olive oil, essential FA (omega-3/6 fish oil)

Property of Saturated Fats

Saturated fats are solid!

Butter sculpture at the CNE 2012

Can you guess who this is?

Forming a triacylglycerol

Condensation reaction between: Hydroxyl on

glycerol Carboxyl on fatty

acidResults in an

ester bond

Triacylglycerol model

2. Phospholipid structure

Glycerol backbone 2 fatty acids

chains phosphate/polar

group

GlycerolFatty acid

Fatty acid

Phosphate/

Polar group

2. Phospholipid structure

Polar head: negatively charged, hydrophilic

Nonpolar tails: fatty acids, hydrophobic

Amphipathic: exhibiting both hydrophilic and hydrophobic properties

tail

Polar Head Groups

Polar Head Groups

Self-assembly of phospholipid

Condition: in water (aqueous)

Self-assembly = spontaneous aggregate

Due to hydrophobic interactions

Micelle: single layer of phospholipid with polar head facing out, nonpolar tails facing inward

http://www.bio.miami.edu/~cmallery/255/255chem/mcb2.20.micelle.jpg

Self-assembly of phospholipid

Phospholipid bilayer have a double layer of phospholipids where the nonpolar tails aggregate forming a hydrophobic core

This is the basic structure of the plasma membrane

http://www.bio.miami.edu/~cmallery/255/255chem/mcb2.20.micelle.jpg

Plasma Membrane

Membranes are made of a bilayer of phospholipids.

hydrophobic tails

hydrophilic heads

hydrophilic heads

Plasma Membrane

Phospholipid Bilayer

3. Steroid

Carbon skeleton, 4 interconnected rings

Three 6C rings, one 5C ringCommon examples:

cholesterol hormones – estrogen, testosterone

Cholesterol Testosterone

Cortisone Aldoesterone

Steroid

4. Wax Structure

Long chain hydrocarbons

Primarily wax esters: a long chain hydrocarbon with an ester group that is not a triglyceride

Could also involve alcohol, aldehyde & ketone groups

http://www.lipidlibrary.co.uk/Lipids/waxes/index.htm

Properties of Wax

Solid at room temperatureBecomes liquid when meltedhas plastic properties: deforms

under pressure without application of heat

thermoplastic is a polymer that turns to a liquid when heated and freezes to a very glassy state when cooled sufficiently

Natural Wax

NaturalAnimal wax: beeswax,

lanolin, shellacVegetable waxes: soy,

jojoba, carnaubaMineral waxes:

petroleum (paraffin) from fossil fuels

SyntheticPolypropylene, Polyethylene

5. Carotenoids

Natural fat-soluble pigment Backbone: 40 carbon molecules with

a polyene chain with alternating single and double bonds

terminated by cyclic end-groups

Polyene structure

Carotenoid: Plant PigmentFound in plants, algae,

photosynthetic bacteriaPigment needed for photosynthesis

in addition to chlorophylle.g. beta-carotene in carrot

http://i03.i.aliimg.com/img/pb/593/581/248/1273569425304_hz-myalibaba-web15.hst.dsl.en.alidc.net_2444.jpg

Carotenoid: use in animals Detecting light: e.g. retinal absorbs light in

retina Serves as antioxidant: double bonds

absorb excess energy from other molecules, protecting cells and tissues from damaging effects of free radicals

Source for vitamin A

http://home.caregroup.org/clinical/altmed/interactions/Images/Nutrients/vitAbetac.gif

What is common to all lipids?

The 5 forms of lipids studied are not built upon any common monomer. What unified these lipids so that they are all classified under the ‘lipid’ category?

In other words, what makes a lipid, a lipid?

HW Question

Why is glycerol not classified as a triose (3C monosaccharide)?

Explain how saturation in a fatty acid chain affects fluidity.

Explain how the length of the fatty acid chain affects fluidity.