Biochemistry 1

Vũ Thanh Ngọc, PhD

Department of Applied Chemistry
School of Biotechnology
International University – VNU HCM
[email protected]

Lipids
 Outline

 Functions

 Sources

 Classification

 Structure

 Properties
 What are Lipids?

A very diverse group of compounds

defined by insolubility in H2O

General Biochemistry 1 3
 Functions
• Stored energy
– Fatty acids ~ same low oxidation state (highly
reduced) as hydrocarbon in fossil fuels
– The oxidation reaction of fatty acids are highly
exergonic
• Structural components of plasma membrane
• Enzyme cofactors, electron carriers,
pigment, anchor, chaperones, emulsifying
agent, hormones, intracellular messenger
General Biochemistry 1 4
 Substrates of Catabolism
Contain Reduced Forms of Carbon

Comparison of the state of reduction of carbon atoms

in biomolecules. Chains of –CH2- groups are the most
energy-rich form of reduced carbon in the biosphere.
Carbon dioxide is the final product of catabolism and
the most oxidized form of carbon in the biosphere.
5
Classification of Lipids

sterols

General Biochemistry 1 6
 Classifications
1. Fatty Acids
2. Triacylglycerols
3. Waxes
4. Membrane lipids:
4a. Glycerophospholipids
4b. Galactolipids and Sulfolipids (plants)
4c. Tetraether lipids (archae bacteria)
4d. Sphingolipids
4e. Sterols (only eukaryotes) 7
 1. Fatty acids
• Fatty acids = hydrocarbon chains
(C4 to C36) that end with -COOH

• Saturated fatty acids have un-branched

and all single bond

• Unsaturated fatty acids have ≥1 double

bonds
General Biochemistry 1 8
 Lipid number and Δx Nomenclature

• Chain length : Number of double bonds (Δx)

• x = position of the double bond

• Example:

16:0 = palmitic acid CH3(CH2)14COOH

18:1(Δ9) = Oleic acid CH3(CH2)7CH=CH(CH2)7COOH

General Biochemistry 1 9
 The n-x nomenclature
• A.k.a ω-x or omega-x nomenclature
• Carbonyl carbon = α, next = β, etc.
• The terminal CH3 carbon is ω (or n)
• xth = position of the C=C counting from ω toward Cα
• Example:
– α-Linolenic acid 18:3(Δ9,12,15) = n-3 or ω-3 fatty acid
– Linoleic acid 18:2(Δ9,12) = n-6 or ω-6 fatty acids
– Oleic acid 18:1(Δ9) = n-9 or ω-9 fatty acids

10
Modified fatty acids found in nature
• Microorganism have branched fatty acids:
Tuberculostearic acid
(CH3 groups perturb
local structure similar
to double bonds)
• Some bacteria synthesize cyclic structures:
Cyclopropane, clyclopropene, cyclepentane

11
 Essential Fatty Acids (EFAs)

Essential fatty acids (used to be vitamin F)

= required by mammals for good health but
cannot synthesize
– Note: NOT to be confused w/ essential oil

General Biochemistry 1 12
 Essential Fatty Acids (EFAs)
• Mammals lack ability to introduce C=C bond
beyond Δ9
• 2 EFAs: linoleic acids (ω-6) (LA),
α-linolenic acids (ω-3) (ALA)
• Precursor for eicosanoids

General Biochemistry 1 13
Conditionally essential fatty acids
• ω-3 fatty acids
– Docosahexaenoic acid (DHA)  brain
– Eicosapentaenoic acid (EPA)
• ω-6 fatty acids
– γ-Linoleic acid (GLA)
– Arachidonic acids (AA) not found in plants,
can be synthesized in mammals only from LA
 brain
– Dihomo-gamma-linolenic acid (DGLA)
General Biochemistry 1 14
Conditionally essential fatty acids
In preterm Infant
LA  AA & ALA  DHA is limited
but present in breast milk
 added to infant milk formula

15
Essential Fatty Acids in the Media

• Fatty acids comprises of all ω-3 and ω-6

(only LA and ALA)

• DHA and AA are conditionally essential

fatty acids, NOT essential for healthy adults

General Biochemistry 1 16
Food Sources of essential fatty acids
• Good sources of ω-3 and ω-6: fish, shellfish,
flaxseed, hemp seed, olive oil, soya oil, canola
oil, chia seed, pumpkin, sunflower, leafy
vegetable, walnuts
• Fish: ω-3 (EPA, DHA)
• Vegetarian diet must consume supplements or
algea products

General Biochemistry 1 17
 Best source of EFAs

Best source ω-3 EFA: flaxseed>chia seed>hemp seed

Best source ω-6 EFA: sunflower, starflower seed

General Biochemistry 1 18
 General Chemical Properties
of Fatty acids
• Usually have even number of C & unbranched
(C12-C24)
• Mono-unsaturated fatty acid has 1 double bond,
usually at C9=C10 except Arachidonic acid
• Poly-unsaturated fatty acid has ≥2 double bonds,
usually C12 and C15
• Double bonds are usually separated by –CH2-
group
General Biochemistry 1 19
 Common fatty acids
up to 20 carbons long
Saturated fatty acids
– Lauric acid (12 C)
– Myristic acid (14 C)
– Palmitic acid (16 C)
– Stearic acid (18 C)
– Arachidic acid (20 C)
 Common fatty acids
up to 20 carbons long
Unsaturated fatty acids
– Palmitoleic acid (16:1)
– Oleic acid (18:1)
– Linoleic acid (18:2)
– α-Linolenic acid (18:3)
– γ-Linolenic acid (18:3)
– Arachidonic acid (20:4)
 A little trick
• Ends in “ic” = no double bond, saturated

• Ends in “leic” = 1-2 double bonds

• Ends in “lenic” = 3 double bonds

• Ends in “donic” = 4 double bonds

General Biochemistry 1 22
 Olive Oil Varieties
 Koroneiki olives from
Greece contain 74.4%
oleic acid.
 Chemlali olives from
Tunisia contain only
54.9% oleic acid.
 Conditions of growth &
maturation of the fruit
affect composition.
General Biochemistry 1 24
 Cis- and Trans- fatty acids
• Almost all naturally occurring unsaturated fatty
acid are in cis configuration
• Trans-fatty acid = result of
– fermentation in rumen of dairy animals (dairy
products and meat)
– hydrogenation of fish or vegetable oils.
• High trans-fatty acid in diet   LDL (bad
cholesterol) and  HDL (good cholesterol)

General Biochemistry 1 25
French fries, donuts and cookies
high in trans-fatty acid!!!

General Biochemistry 1 26
 LDL – bad cholesterol
• Human use receptor-mediated
endocytosis to take in cholesterol
• Cholesterol travels in blood in complex
with protein
• Low density lipoproteins (LDLs) in blood
binds to receptors on plasma membranes
and enter cells by endocytosis.
General Biochemistry 1 27
LDL particle endocytosis

General Biochemistry 1 28
 LDL and HDL
• In hypercholesterolemia, the LDL
receptors are missing  LDL cannot enter
cells but circulate and accumulate in blood
 atherosclerosis (build up of lipid deposit
on walls of blood vessels)
 bad cholesterol
• HDL (high density liproprotein) seem to
protect from artery clogging
 good cholesterol
General Biochemistry 1 29
Physical properties of fatty acids

General Biochemistry 1 30
 Solubility
• Nonpolar hydrocarbon chains
 poor solubility in H2O
– Lauric acid (12:0, Mr 200) – 0.063 mg/g
– Glucose (Mr 180) 1,100 mg/g
• The longer the hydrocarbon chain
 the fewer the double bonds
 the lower the solubility
• Short fatty acid is slightly soluble because
of -COOH group General Biochemistry 1 31
 Melting points
• Saturated fatty acid tightly pack together
in linear conformation with val de waals
interactions  high melting point
• Unsaturated fatty acid has a kink (cis
configuration C=C bond)  cannot pack
tightly together
 lower melting points than saturated
fatty acid of same length
General Biochemistry 1 32
Saturated vs. Unsaturated
Fatty Acids

General Biochemistry 1 33
 Fatty acids can be esterified
• Fatty acids are typically esterified at COOH
to esters or amides
 even less soluble than regular fatty acids
• Un-esterified fatty acids are non-covalently
bound to protein carriers

General Biochemistry 1 34
 2. Triacylglycerols
• Simplest lipids = 3 fatty acids ester linked 1 glycerol
Fatty acid of Glycerols
• Other names: triglycerides, fats or neutral fats

General Biochemistry 1 35
 Simple triacylglycerols
• Simple triacylglycerols = all 3 fatty acids
are the same

• Named after the fatty acids

• Example:

– Triacylglycerols of 16:0, 18:0, 18:1

– Tristearin, tripalmitin, triolein

General Biochemistry 1 36
 Mixed triacylglycerols
• 2-3 different fatty acids
 name the position of each fatty acid
• Triacylglycerols have –OH and COOH
groups involved in ester bonds
 very hydrophobic
 oils don’t dissolve in H2O but 2 phases

General Biochemistry 1 37
 Triacylglycerols – sources
• In Eukaryote cells: stored in oily droplets
within cytosol
• In plants: stored in seeds
• In vertebrate animals: stored in adipocytes
(fat cells with large amounts of fat droplets)
• In human: stored in fat tissue of adipocytes
under skin, abdominal cavity, mamary glands
• Lipase = enzyme hydrolyzes triacylglycerols
 release fuels General Biochemistry 1 38
Energy storage in triacylglycerols
over polysaccharides
1. Carbon atoms are more reduced
 > 2x energy as carbohydrates
2. 1 g of Carbohydrates has 2 grams of H2O
 heavier than anhydrated fats
Example:
– A moderately obese person stores 15-20 kg of
triacylglycerol  enough energy for months.
– Glycogen  enough energy for 1 day.  quick
source of energy
 Triacylglycerols can be
insulation and buoyance

• Warm blooded polar animals:

seals, walruses, penguins

• Hibernating animals: bears

General Biochemistry 1 40
Polar Bears Prefer Nonpolar Food
 Sperm Whales use fats
as buoyance
• Sperm whales use storage of fats in their
heads as buoyancy
• The head = 1/3 of body weight,
90% of head is spermaceti oil (3600 kg)
= mixture of triacylglycerols and waxes of
balance of saturated/unsaturated and
necessary chain length
 liquid at 37oC but crystalize at 31oC
General Biochemistry 1 42
 Sperm Whales use fats
as buoyance

• When temperature ↓  crystalize and more

dense  match density of deep water
• When temperature ↑  liquidize  less
dense  float
General Biochemistry 1 43
Sources of triacylglycerols in food
• Vegetable oils (corn, peanut, soybean) &
olive oil = triacylglycerols of mostly
unsaturated fatty acids  liquid at room
temperature
• Animal fats = triacylglycerols of saturated
fatty acids  solid at room temperature
• Margarines = catalytic hydrogenation of
double bond and convert cis to trans-
 solid
General Biochemistry 1 44
Saturated vs. Unsaturated Fat Diet
• Animal oils are high in saturated fats
• Vegetable oils are high in unsaturated fats

General Biochemistry 1 45
Saturated vs. Unsaturated Fat Diet
• High saturated fat diet
 high risk of cardiovascular diseases
(heart attacks and strokes)

• High trans fat

 high LDL, low HDL
 high risk coronary heart disease

General Biochemistry 1 46
Saturated vs. Unsaturated Fat for Frying
Unsaturated fats are thermal oxidized
 shorter chain

Heat, light, metals

(Fe3+ and Cu2+) and
reactive oxygen
species facilitates
radical formation of oil

doi: 10.1111/j.1750-3841.2007.00352.x
47
Saturated vs. Unsaturated Fat for Frying
• Palm oil contains more saturated fats
 withstand high heat & is resistant to oxidation
• Coconut oil high in lauric and myristic acids
(both saturated) & very few unsaturated fatty acids
 suitable for frying
• Olive oil contains high level of monounsaturated
fats (~73%)
 should not be used for frying
(with temperature ≥ 230oC)
48
 Spoiled fats - Rancidfication
Oxidation of double bonds
 aldehydes and carboxylic acids of shorter length
 more volatile
 rancid (old and stale) smell

49
 Saponification
• Acylglycerol (mono-, di-, tri-) can be
hydrolyzed by heating with acid or base
• Alkaline hydrolysis of triacylglycerols
= saponification
• Soap = Metal salt of an acid derived from fats
Divalent ions (Mg2+ and Ca2+) in hard H2O ppt
with RCOO-  detergent

50
 3. Waxes
• Waxes = esters of long-chain saturated
(C14-C36) and unsaturated fatty acids with long
chain alcohols (C16-C30)
• Melting point ~ 60- 100oC

51
Waxes – Sources and Functions
• Plankton (free-floating microorganism):
main storage of energy
• Birds: use wax from preen glands to keep
feather water repellent
• Many tropical plant leaves
(holly, Rhododendrons, poison ivy)
 anti-evaporation of H2O and anti-parasite
• Lanolin (lamb’s wool), beeswax and
spermaceti oil  lotions, ointments, polishes
General Biochemistry 1 52
 4. Membrane lipids
(Amphipathic)
From Amphiphile = Amphis (both) + Philia (love)

General Biochemistry 1 53
 Membrane Lipids

4a. Glycerophospholipids

4b. Galactolipids and sulfolipids

4c. Archaebacteria tetraether lipids

4d. Sphingolipids

4e. Sterols

General Biochemistry 1 54
Lipids form bilayer
plasma membranes

General Biochemistry 1 55
Lipids form bilayer
plasma membranes

General Biochemistry 1 56
Lipids form bilayer
plasma membranes

General Biochemistry 1 57
 4a. Glycerophospholipids
Glycerophospholipids
• 2 fatty acids attached to C1 and C2 of Glycerol
by ester linkage.
• A highly polar group (head group) is attached
through phosphodiester linkage to the 3rd
Carbon.

58
Common Glycerophospholipids

General Biochemistry 1 59
 The sn-Numbering System
Prio-3 Prio-2

Prio-4
Prio-1

The two identical –CH2OH groups on the central

carbon of glycerol may be distinguished by imagining
a slight increase in priority for one of them (by
replacement of an H by a D) as shown. The molecule
may then be named using the (R,S) or Cahn, Ingold,
Prelog naming system.
 4 steps to determine R, S
1. Rank atoms about the C* by atomic number
2. Ensure number 4 is in the back
3. Cross out number 4
4. Trace an arc from 1  2  3
Priority
H
C<N<O<F
P<S<Cl Priority
Br
I
General Biochemistry 1 61
 Chirality of glycerophospholipids
• Glycerol is prochiral (an achiral molecule that
can be converted to chiral in 1 single step)
• Addition of Phosphate group at 3rd Carbon
 C2 becomes chiral
 dilema when using D/L system

General Biochemistry 1 62
Stereospecific numbering – sn system
• pro-S position of a pro-chiral atom = 1-position
• Pro-chiral atom = 2-position
• Sn means –OH group is on the left of Fischer P.
• Sn-1 = phosphate at top C, Sn-3 = phosphate bottom
 Phosphoglycerides = sn-glycerol-3-phosphate

General Biochemistry 1 63
Naming of Glycerophospholipids
• Name = phosphatidyl + head group (X)
– Eg: phosphatidylcholine,
phosphatidylethanolamine
• Phosphate group = negatively charged
• Polar alcohol = Negative, neutral or positive
• 2 fatty acids can be of a wide variety
– C1 ~ saturated fatty acid C16-C18
– C2 ~ unsaturated fatty acid C18-C20
General Biochemistry 1 64
 Phospholipids with
ether-linked fatty acids
• Ether lipids = glycerophospholipids with 1
of 2 acyl chains (saturated or unsaturated
Δ1 ) is attached to glycerol by ether linkage
• Example:
Plasmalogen (vertebrate heart tissue)

General Biochemistry 1 65
4b. Galactolipids and sulfolipids
• Found in thylakoid
membranes of Chloroplast,
make up of 70-80% of total
membrane lipids of vascular
plant  most abundant
membrane lipid on Earth
• 1 or 2 galactose residues
are O-glycosidic linked to
1,2-diacylglycerol
• Plants probably replace
sugar and sulfonated sugar
for phosphate as it is scarce
in soil
General Biochemistry 1 66
4c. Archaebacteria tetraether lipids
• Glycerol dialkyl glycerol tetraethers
(GDGTs) = 32 carbon branched
hydrocarbons linked at each end to glycerol
• Ether linkage (-O-) instead of ester linkage
(-O-CO-)
• C* is in R configuration instead of S like other
kingdom

General Biochemistry 1 67
 4d. Sphingolipids
• Does NOT contain glycerol
• Contains
– Sphingosine or its derivatives
– 1 long chain fatty acid = amide
– 1 polar head group linked by glycosidic
linkage or phosphodiester linkage

General Biochemistry 1 68
 Classification of Sphingolipids
• Ceramide = fatty acid is amide linked to NH2 on
C2 = structural parent of all sphingolipids
• Sphingolipids = derivatives of Ceramides
• 3 subclasses:
– Sphingomyelins
– Glycosphingolipids (cereboside and globoside)
– Gangliosides

General Biochemistry 1 69
Some sphingolipid head groups

General Biochemistry 1 70
 Sphingomyelins
• Sphingomyelins = ceramide + phosphocholine or
phosphoethanolamine
• Sphingomyelins in plasma membrane, myelin of
axons of neurons
• Sphingomyelins resembles phosphatidylcholines
3D structure and general properties

General Biochemistry 1 71
Similarity with Phosphatidylcholine

General Biochemistry 1 72
Classification of Lipids

sterols

General Biochemistry 1 73
 Glycosphingolipids
• Glycosphingolipids’ head groups = ≥1 sugars
connected directly to –OH at C1 of ceramide
• Cerebroside = 1 sugar linked to ceramide.
If sugar = galactose in neural tissue plasma
membrane, glucose in non-neural tissue plama
membrane
• Globoside = has ≥2 sugars (D-glucose, D-
galactose, N-acetyl-D-galactosamine)
• Cereboside and globosides = neutral glycolipids
General Biochemistry 1 74
Glycosphingolipids

General Biochemistry 1 75
 Gangliosides
• Gangliosides’ head groups = oligosaccharides
AND ≥1 N-acetylneuraminic acid (Neu5Ac or
sialic acid)
• Sialic acid = a glucuronic acid COO- at C6,
pyruvate at C1 and N-acetylamine at C2
• GM (M= mono), GD, GT, GQ has 1, 2, 3, 4 sialic
acid residues respectively

General Biochemistry 1 76
 Sphingolipids at Cell Surfaces
are sites of biological recognition
• Sphingolipid's biological role at the point of
discovery was as mysterious as the Sphinx.

• Only a few sphingolipids’ function have been

discovered thus far

General Biochemistry 1 77
Gangliosides – determinant
of human blood types

General Biochemistry 1 78
 Lysosomes
Phospholipids and Sphingolipids are
degraded in lysosomes

General Biochemistry 1 79
Abnormal accumulation
of membrane lipids

80
Terpenes and their biological relevance
Terpenes are a class of lipids formed from
combinations of isoprene units
• “Isoprene” is 2-methyl-1,3-butadiene
(natural rubber = poly-cis-isoprenes)
• Monoterpenes consist of 2 isoprene units
• Sesquiterpenes consist of 3 isoprenes
• A diterpene consists of 4 isoprene units
• All steroids (including cholesterol and the steroid
hormones) are terpene-based molecules
Terpenes and their biological relevance
Note the two possible linkage modes:
•“head-to-tail”
•“tail-to-tail”

Figure 8.12 The structure of isoprene (2-methyl-1,3-butadiene)

and the structure of head-to-tail and tail-to-tail linkages.
Isoprene itself can be formed by distillation of natural rubber, a
linear head-to-tail polymer of isoprene units.
Terpenes and their biological relevance

Many monoterpenes are readily recognized by their

characteristic flavors or odors (limonene in lemons;
citronellal in roses and perfumes; menthol used in cough drops).
Terpenes and their biological relevance

The diterpenes include

retinal (the visual pigment
in rhodopsin), and phytol
(found in chlorophyll).
Gibberellic acid is a plant
hormone.
Terpenes and their biological relevance

The triterpene
lanosterol is a
constituent of
wool fat and is
also a precursor
to cholesterol and
the other steroids.

Lycopene is a
carotenoid found
in ripe fruit,
especially
tomatoes.
 4e. Sterols
• Steroids are polyprenyl (isoprene-based)
• Sterols = steroid nucleus + a hydroxyl
group + nonpolar hydrocarbon side chain
• Steroid nucleus = 3 six carbon rings + 1
five carbon ring fused together
 planar and relatively rigid

General Biochemistry 1 86
 4e. Sterols
• O at C3 (OH = sterols)
• CH3 group at C10 or C13
• Alkyl (8-10 C) at C17
• C at C10,13 and alkyl on the same side of
the nucleus  β-orientation
• Opposite = α

General Biochemistry 1 87
 Cholesterol
• Cholesterol = 1 steroid nucleus + OH at
C3 and 16 Carbon alkyl side chain at C17
• Cholesterol is most common animal
steroid and precursor for all other animal
steroids

General Biochemistry 1 88
Cholesterol and bile acid

General Biochemistry 1 89
 Sterols functions
• Examples of sterols: Cholesterol, stigmasterol
(plants), ergosterol (fungi)
• Sterols serve as:
– membrane constituents
– Precursor to steroid hormones
– Emulsifying detergent (bile acid)
• Only eukaryotes synthesize sterols, bacteria
cannot, but some incorporate them to their
membranes General Biochemistry 1 90
Lipids form bilayer plasma membranes

General Biochemistry 1 91
 Membrane structures
• Saturated fatty acids can form ordered,
rigid arrays
• Unsaturated fatty acids form flexible,
fluid aggregates

General Biochemistry 1 92
Vitamin D3 is made from sterols

General Biochemistry 1 93
Lipids as Signals, cofactors
& pigments

General Biochemistry 1 94
Lipids as Signals, cofactors and pigments

• Signals: hormones, growth factors

• Cofactors: enzyme cofactors, transfer sugar

• Pigment: vitamin A, D, E, K

General Biochemistry 1 95
 Phosphatidylinositols:
intracellular signal
• Phosphatidylinositols is phosphorylated to
Phosphatidylinositol 4,5-bisphosphate (PIP2)
in the inner face of plasma membrane
• It can
– Binding site for cytoskeletal proteins
– Proteins involved in exocytosis
– Mediator of signals from intracellular
messenger to outer membranes
General Biochemistry 1 96
Phosphatidylinositol pathway
1. Remove the phospholipid
head group: phospholipase C
hydrolyzes the bond between
glycerol and PIP2  2
products

2. Products 1: inositol 1,4,5-

trisphosphate (IP3) 
release Ca2+ from
endoplasmic reticulum (ER)

3. Products 2: diacylglycerol +
Ca2+ flux  activates protein
kinase C

General Biochemistry 1 97
 Inositol phospholipids:
points of nucleation
Proteins with PH and PX domains bind
phosphatidylinositols  initiate formation of
multienzyme complexes

When glucose
level in blood is
high  pancreas
secrets insulin

98
 Phosphatidylinositols:
intracellular signal
• Ceramide and Sphingomyelin are potent
regulators of protein kinases, cell division,
differentiation, migration, apoptosis
• Sphingosine can be phosphorylated
sphingosine-1-phosphate (S1P) inside cells.
• S1P may either exert a variety of intracellular
effects or may be excreted from the cell, where it
can bind to membrane receptor proteins, either
on adjacent cells or on the cell from which it
was released.
General Biochemistry 1 99
Sphingolipids can be modified or broken
down to produce chemical signals
 Sphingolipids can be modified or
broken down to produce chemical signals

Figure 8.20
 Eicosanoids
Eicosanoids = paracrine hormones,
derivatives of arachidonic acid
(20:4(Δ5,8,11,14)) (“eikosi” = twenty)

102
 3 classes of Eicosanoids
Prostaglandins (PG) = 5 carbon ring
cyclized from arachidonic acid (prostate
glands) regulates sysntheis of cAMP, wide
range of regulation, contract smooth muscle,
affect blood flow, produce fever,
inflammation and pain, responsiveness to
hormones

103
 3 classes of Eicosanoids
Thromboxanes = 6 member ring (inclg
ether) (platelets)  formation of blood clots
and ↓ blood flow to blood clots.

General Biochemistry 1 104

 3 classes of Eicosanoids
Leukotrienes: 3 conjugated double bonds
(leukocytes)  contraction of muscle lining
the airways to the lung

General Biochemistry 1 105

 Drugs targeting eicosanoid
• Nonsteroidal anti-inflammatory drugs
(NSAIDs) inhibits prostaglandin H2 synthase
(Cyclooxygenase or COX) that catalyzes
conversion of arachidonate to prostaglandins
and thromboxanes
• Antiasthmatic drugs: Overproduction of
leukotriene causes asthmatic attacks
 prednisone

106
Eicosanoids

107
 Steroid Hormones
• Steroids = oxidized derivatives of sterols, has
sterol nucleus but lacks alkyl chain
 more polar
• Steroid hormones travel through blood, binds to
specific receptor and changes gene expression
and metabolism
• Major groups:
– sex hormones: testosterone, estradiol,
– Hormones produced by adrenal cortex:
cortisol, aldosterone 108
Some steroid hormones

General Biochemistry 1 109

Plants use Phosphatidylinositols, Steroids,
Eicosanoid-like compounds in signalling
• Vascular plants use PIP2 and phospholipase
to release IP3 to regulate intracellular Ca2+
• Brassinolide (similar to steroids) is potent
growth regulator
• Jasmonate (similar to eicosanoids) derived from
18:3(Δ9,12,15)
 trigger plant’s defense response to insect-
inflicted damage. Methyl ester of jasmonate
gives fragrance of jasmine oil in perfume
industry
General Biochemistry 1 110
Plant hormones

General Biochemistry 1 111

 Plant Sterols and Stanols:
Natural Cholesterol Fighters
Dietary guidelines for optimal health call for reducing
cholesterol intake. Eating plant sterols and stanols can
play a role. These cholesterol mimics bind to
cholesterol receptors on intestinal cells and block
absorption of cholesterol itself. (Plant sterols and
stanols are not themselves absorbed.)

(Note: Stanols are fully reduced sterols.)

 Plant Sterols and Stanols:
Natural Cholesterol Fighters
Raisio Group, a Finnish company, has developed
Benecol, a stanol ester spread (available in many
U.S. supermarkets) that can lower LDL cholesterol by
up to 14% if consumed daily (see graph on next slide)
 Plant Sterols and Stanols:
Natural Cholesterol Fighters

Serum cholesterol
before and after
consumption of
Benecol.
Green circles: 0 g/day
Red squares: 2.6 g/day
Blue triangles: 1.8 g/day
 Summary

 Functions

 Sources

 Classification

 Structure

 Properties