Cholesterol – a biomolecule Bad cholesterol

Cholesterol – a biomolecule
Bad cholesterol – a strange tale
Good cholesterol - indeed
Thomas B. Kuhn: University of Alaska, Cereon Biotechnology LLC
This document is protected by copyright
© Dr. Thomas B. Kuhn
All rights reserved
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Cholesterol:
the good, the bad, and the ugly
Bad Cholesterol
Good Cholesterol
Ugly Cholesterol
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Cholesterol:
its just a molecule
Cholesterol
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Cholesterol – a biomolecule
Bad cholesterol – a strange tale
Good cholesterol - indeed
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Cholesterol – a biomolecule
ž  What
is cholesterol?
ž  Where are the origins of cholesterol?
ž  Who transports cholesterol?
ž  What role(s) has cholesterol?
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What is Cholesterol?
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Cholesterol is a Lipid
Cholesterol is synthesized by
all cells
Cholesterol is taken up from
extracellular sources (food)
Cholesterol is vital for
membrane integrity
Cholesterol is a precursor for
a plethora of biomolecules
25% of all Cholesterol is in the
brain !
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What is Cholesterol?
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Cholesterol is synthesized by our body
Cholesterol is ingested through food sources
Cholesterol has 27 carbon atoms
All carbon atoms are derived from isoprene (C5 unit)
Isoprene is generated from acetate
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Origins of Cholesterol: Biosynthesis
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4 major steps
4 major intermediates
Acetate - the starting unit, most
common metabolite
Mevalonate – key precursor to
generate isoprene
Isoprene – curcial building block for
many biomolecules
Squalene – principal carbon
skeleton for all sterol-like compounds
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Mevalonate
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2 Acetates are fused to a
ketone body
Additional condensation of an
acetate generates β-hydroxy-βmethylglutarate
Reduction of β-hydroxy-βmethylglutarate by HMG-CoA
reductase,
HMG-CoA reductase is the key
regulatory site of cholesterol
synthesis
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Squalene
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Consecutive condensation of isoprene (5 carbons)
Geranyl (2 isoprenes, 10 carbons or 2x 5 carbons)
Farnesyl (3 isoprenes, 15 carbons or 3 x 5 carbons)
Squalene (2 farnesyl, 30 carbons = 2 x 15 carbons)
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Cholesterol
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Origins of Cholesterol: Cellular Uptake
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Regulation of Cholesterol Origins
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HMG-CoA reductase – classic
feedback inhibition
Sufficient Cholesterol signals
cholesterol esters, blocks up
take, and blocks synthesis
Transcriptional via the Sterol
regulatory element-binding
proteins (SREBPs)
Opposing effect of insulin and
glucagon
Cross talk to blood sugar
levels
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Regulation of Cholesterol Origins
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Uptake of cholesterol is measured by sterol-sensing protein
Binding of cholesterol to sterol sensing protein initiates degradation
of HMG-CoA reductase
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Cholesterol Transport
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Cholesterol Transport
Liver
VLDL
Blood Serum
LDL
Tissue
Lipid
t1/2= 2-4 d
removal
HDL
Tissue
Synthesis of steriods, bile acids etc
LDL binds LDL receptor –
internalized – delivery of cholesterol
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Cholesterol Transport - Lipoproteins
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Cholesterol like other lipids virtually
water insoluble
Plasma lipoproteins are carriers
Apoprotein (ApoB-100) in complex
with lipids
Lipoprotein complexes vary in density
reflecting distinct functions
Major Apolipoproteins are B and E
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HDL vs LDL
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Roles of Cholesterol
ž  Precursor
of many biomolecules
ž  Major component of cell membranes
ž  Impacts cell membrane fluidity
ž  Organizes cell membranes
ž  Chaperone for protein function
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Isoprenoid Metabolism
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Steroid Hormones
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Cholesterol is the starting material for the synthesis of all
steroid hormones
Cholesterol is converted to progesterone
Progesterone serves as precursor for other steroid
hormones.
Progesterone
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Testosterone
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Glucocorticoid Hormones
—  Synthesized in the adrenal cortex.
—  Regulate metabolism of carbohydrates.
—  Decrease inflammation and mediate stress
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Bile Salts
Bile salts are oxidation products of cholesterol.
—  Synthesized in the liver, stored in the
gallbladder, and secreted into the intestine
where they emulsify dietary fats and aid in their
absorption and digestion.
H3 C
HO
C H3
H3 C
HO
OH
O
H3 C
HO
C H3
NH
C O O-
H3 C
HO
Glycocholate
(from glycine)
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NH
S O3 2 -
OH
Taurocholate
(from taurine)
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Vitamin D, A, E, and K
Vit K
Vit A
Vit D
Vit E
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Ubiquinone
Ubiquinone is an essential electron transporter of
cellular respiration
—  Enables switch from 2 to 1 e- transport onto
oxygen.
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Biological Membranes
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Complex lipids including cholesterol form the membranes around
cells and subcellular structures
Compartmentalization of biological processes
Membranes are flexible, self-sealing, selectively permeable
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Biological Membranes are heterogeneous
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Biological Membranes - Fluidity
(b) Fluid state
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Cholesterol and Membranes
Found in varying amounts throughout the membrane
ž  Stiffen and Strengthen membranes due to its sterol group
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Lipid Rafts - rigid platforms
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Lipid Rafts: Communication Portals
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Cholesterol – a chaperone
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Cholesterol – a chaperone
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Cholesterol – a chaperone
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Cholesterol – Alzheimer’s Disease
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Cholesterol is
necessary for the
proper function of
Amyloid precursor
protein (APP)
Alzheimer’s disease –
alterations in lipid
metabolism
Alzheimer’s disease –
alteration in lipid raft
organization
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?
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Cholesterol – HIV infection
gp41 mediates
binding of HIV virus
to cell membranes
ž  Cholesterol
interaction with gp41
is necessary for
virus entry
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The Official Message
National Heart, Lung, and Blood Institute - Mission Statement
ž  provides global leadership for a research, training, and education
program to promote the prevention and treatment of heart, lung,
and blood diseases and enhance the health of all individuals so
that they can live longer and more fulfilling lives.
ž  stimulates basic discoveries about the causes of disease
ž  enables the translation of basic discoveries into clinical practice
ž  fosters training and mentoring of emerging scientists and
physicians
ž  communicates research advances to the public
ž  to help reduce the burden of heart, lung, and blood diseases
worldwide.
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The official messages
ž  NHLBI
ž  WebMD
(specifically recommended by
my health insurance)
ž  American Heart Association
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Cholesterol Guidelines
ž 
The National Cholesterol Education Program
(NCEP) is a program managed by the NHLB
institute (NIH) with the goal to reduce increase
Cardiovascular Disease (CVD) to due elevated
cholesterol in the US since 1985
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The assigned goal of the NCEP committee is to meet
on a recurring basis, review ongoing scientific
research about CVD and make simplified,
consensus, committee recommendations to be
promoted by NIH and AHA to physicians and public
to reduce CVD death
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How is Cholesterol Measured
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Blood analysis (fasting or non fasting)
Measurement of total cholesterol, LDL, HDL, and
triglycerides (mg/dL or mg/100 ml)
Total Cholesterol
Total LDL
Less than 200mg/dL - Desirable
200-239 mg/dL - Borderline high
240mg/dL and above – High
Less than 100mg/dL - Optimal
100-129mg/dL - Near optimal
130-159 mg/dL - Borderline high
160-189 mg/dL - High
190 mg/dL and above - Very High
Triglycerides
Total HDL
normal < 150 mg/dL
Borderline - 150-199 mg/dL
High - 200-499 mg/dL
Risk > 500 mg/dL
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Less than 40 mg/dL - major risk
40—59 mg/dL - better
over 60 mg/dL protective
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Cholesterol Guidelines
88% of NCEP members
are directly paid
by the pharmaceutical
industry
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Facts about LDL and HDL
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Most of the cholesterol is carried by LDL true
Normal plasma levels are 175 mg/100 mL false (!!!!)
LDL receptors necessary for LDL uptake
true
LDL receptors number controlled by intracellular
cholesterol levels
true
Familial hypercholesterolemia – low LDL receptors
thus high plasma cholesterol (>680 mg)
true
High plasma cholesterol causes premature
atherosclerosis and heart attacks
false!!!!!
high LDL-low HDL ratio = a warning
true/false
serum Chol à Chol synthesis
true
Chol in diet directly affects Chol in blood
false
statin drugs inhibit Chol synthesis
true
(HMG-CoA reductase)
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Cholesterol - Summary
Cholesterol is vital for hormone production
ž  Cholesterol is vital for digestion (bile acids)
ž  Cholesterol is vital for membrane
organization
ž  Cholesterol is vital for the brain
(neurotransmitter receptors)
ž  There is little if any scientific basis that
cholesterol causes heart disease
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