Lipids: Triglycerides and Fatty Acids

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Questions and Answers

In the context of lipid geometry pertaining to double bonds, which of the following statements most accurately describes the distinction between cis and trans configurations and their implications for the physical state of fats at room temperature?

  • Cis double bonds result in a more linear structure that allows for tighter packing of fatty acids, leading to higher melting points compared to trans double bonds.
  • Trans double bonds are predominantly found in nature, lending to the higher prevalence of solid fats compared to the relative scarcity of naturally occurring cis fats.
  • Trans double bonds introduce kinks in the fatty acid chains, preventing close packing and resulting in higher melting points compared to cis double bonds.
  • Cis double bonds create a bend in the fatty acid chain, hindering close packing and typically resulting in lower melting points compared to saturated fats and trans double bonds. (correct)

The designation 'omega-n' in fatty acid nomenclature directly indicates the number of carbon-carbon double bonds present in the fatty acid molecule.

False (B)

Articulate the biochemical rationale explaining why humans lack the enzymatic capability to introduce double bonds beyond the ninth carbon atom (Δ9 desaturase limitation), when numbering from the carboxyl end of a fatty acid.

Humans lack the Δ12 and Δ15 desaturase enzymes required to insert double bonds beyond carbon 9.

The primary structural distinction between sterols and other lipid classes, such as triglycerides and phospholipids, lies in sterols possessing a characteristic _______ ring system, while other lipids feature a glycerol backbone.

<p>tetracyclic</p> Signup and view all the answers

Match each lipoprotein class with its primary function in lipid metabolism.

<p>Chylomicrons = Transport of dietary triglycerides from intestines to peripheral tissues VLDL (Very Low-Density Lipoproteins) = Transport of triglycerides synthesized in the liver to peripheral tissues LDL (Low-Density Lipoproteins) = Transport of cholesterol from the liver to peripheral tissues HDL (High-Density Lipoproteins) = Transport of cholesterol from peripheral tissues back to the liver for excretion</p> Signup and view all the answers

Considering the metabolic fates of fatty acids, which pathway is primarily responsible for the ATP production from excess triglycerides?

<p>Beta-oxidation (A)</p> Signup and view all the answers

Complete hydrogenation of unsaturated fatty acids results in the formation of trans fats.

<p>False (B)</p> Signup and view all the answers

Explain the mechanism by which plant sterols are effective in reducing blood cholesterol levels.

<p>Plant sterols interfere with cholesterol absorption in the small intestine.</p> Signup and view all the answers

The enzyme _______, situated on the endothelium of blood vessels, is crucial for hydrolyzing triglycerides in lipoproteins, facilitating the uptake of fatty acids into cells.

<p>lipoprotein lipase</p> Signup and view all the answers

Match the fatty acid with its corresponding shorthand nomenclature.

<p>alpha-linolenic acid = 18:3n3 linoleic acid = 18:2n6 oleic acid = 18:1n9 arachidonic acid = 20:4n6</p> Signup and view all the answers

Identify the primary reason that fat replacers, such as olestra, can potentially lead to gastrointestinal side effects.

<p>Inability to be absorbed in the small intestine. (C)</p> Signup and view all the answers

De novo lipogenesis, the synthesis of fatty acids from non-lipid precursors, is primarily regulated by dietary cholesterol intake.

<p>False (B)</p> Signup and view all the answers

Outline the key steps involved in micelle formation and its significance in the context of lipid absorption within the small intestine.

<p>Emulsification by bile, incorporation of lipids, transport across unstirred water layer.</p> Signup and view all the answers

Following their synthesis within enterocytes, long-chain fatty acids are re-esterified into triglycerides and packaged, along with apolipoproteins, phospholipids, and cholesterol, into large lipoprotein particles called _______ for transport into the lymphatic system.

<p>chylomicrons</p> Signup and view all the answers

Match the lipoprotein with its role in cholesterol transport.

<p>LDL = Transports cholesterol from the liver to peripheral tissues HDL = Picks up cholesterol from peripheral tissues and returns it to the liver VLDL = Transports endogenously synthesized triglycerides from the liver to peripheral tissues</p> Signup and view all the answers

When considering the impact of dietary fatty acids on cardiovascular health, what is the most accurate interpretation of the research regarding saturated fats, monounsaturated fats (MUFA), and polyunsaturated fats (PUFA) as it relates to LDL cholesterol?

<p>Replacement of saturated fats with MUFA/PUFA can reduce LDL cholesterol, suggesting that the overall fatty acid profile is more critical than individual fatty acids. (D)</p> Signup and view all the answers

The designation 'essential' for a fatty acid implies that the human body can synthesize it de novo, but must do so under specific physiological conditions.

<p>False (B)</p> Signup and view all the answers

Explain how cis and trans fatty acids differ in their chemical structure, and how this structural difference affects their physical properties, such as melting point.

<p>Cis: same side, bent; trans: opposite sides, linear; melting - point higher in trans.</p> Signup and view all the answers

The process of _______ involves the enzymatic modification of essential fatty acids, such as linoleic acid and alpha-linolenic acid, to produce longer-chain, more unsaturated derivatives like arachidonic acid, EPA, and DHA.

<p>desaturation and elongation</p> Signup and view all the answers

Match the sign of essential fatty acid deficiency with the corresponding family (n-6 or n-3).

<p>n-6 deficient = IQ n-3 deficient = Visual acuity</p> Signup and view all the answers

Considering the current recommendations and perceptions regarding dietary fat intake, which statement best reflects the nuanced view on saturated fats and their role in cardiovascular health?

<p>While high intakes of saturated fats are associated with increased LDL cholesterol, the impact on cardiovascular health is complex and depends on the source of saturated fats and the overall dietary pattern. (A)</p> Signup and view all the answers

According to current guidelines, dietary cholesterol, rather than blood cholesterol, is directly linked to increased risk of cardiovascular disease.

<p>False (B)</p> Signup and view all the answers

Describe the role of the lungs in fat metabolism and excretion.

<p>Excrete CO2, a byproduct of fat breakdown.</p> Signup and view all the answers

The liver plays a crucial role in maintaining cholesterol homeostasis by acting as a _______, synthesizing cholesterol de novo and adjusting its production based on dietary intake and bodily needs.

<p>thermostat</p> Signup and view all the answers

Match the term with the definition.

<p>MUFA = Monounsaturated fatty acids. PUFA = Polyunsaturated fatty acids. SAFA = Saturated fatty acids.</p> Signup and view all the answers

Which of the following statements best describes the physiological role of bile in lipid digestion and absorption?

<p>Bile emulsifies fats, increasing their surface area for enzymatic digestion. (B)</p> Signup and view all the answers

The primary function of chylomicrons is to transport lipids from the liver to peripheral tissues.

<p>False (B)</p> Signup and view all the answers

Explain the role of lipoprotein lipase (LPL) in the metabolism of lipoproteins.

<p>Hydrolyzes triglycerides in lipoproteins to release fatty acids.</p> Signup and view all the answers

In the context of essential fatty acid metabolism, _______ and _______ are derivatives of alpha-linolenic acid (ALA) that have been shown to play a significant role in reducing the risk of heart disease through various mechanisms, including reducing triglyceride levels and demonstrating anti-inflammatory effects.

<p>EPA, DHA</p> Signup and view all the answers

Match each food source with its predominant type of fatty acid.

<p>Olive oil = Monounsaturated fatty acids (MUFA) Coconut oil = Saturated fatty acids (SAFA) Flaxseed oil = Omega-3 polyunsaturated fatty acids Corn oil = Omega-6 polyunsaturated fatty acids</p> Signup and view all the answers

When assessing the impact of dietary interventions on blood lipid profiles, which parameter provides the most comprehensive indication of cardiovascular risk?

<p>Ratio of total cholesterol to HDL cholesterol. (D)</p> Signup and view all the answers

Plant sterols effectively lower blood cholesterol levels by inhibiting de novo cholesterol synthesis in the liver.

<p>False (B)</p> Signup and view all the answers

Describe the role of the enzyme cholesterol esterase in the digestion of lipids. Particularly, where does it act, and what is the product of its activity?

<p>Small intestine; free cholesterol and a fatty acid.</p> Signup and view all the answers

The presence of _______ double bonds in fatty acids decreases their melting point due to the introduction of kinks in the acyl chain, which interferes with efficient molecular packing.

<p>cis</p> Signup and view all the answers

Match each class of eicosanoids with its primary role:

<p>Leukotrienes = Inflammatory mediators, particularly in asthma and allergic reactions Prostaglandins = Modulation of inflammation, pain, and fever Thromboxanes = Platelet aggregation and vasoconstriction</p> Signup and view all the answers

What is the impact on the designation if canola oil says high oleic?

<p>Lower ALA (D)</p> Signup and view all the answers

The intake of eggs affect blood cholesterol for healthy individuals.

<p>False (B)</p> Signup and view all the answers

Give a reason why short and medium chain fatty acids aren't packaged into chylomicrons.

<p>Easily absorbed</p> Signup and view all the answers

The most valuable export commodity in Canada from oil is ______.

<p>Canola</p> Signup and view all the answers

Flashcards

What are lipids?

Molecules that are insoluble in water, found in our diet and foods.

What are triglycerides?

3 fatty acids linked to a glycerol backbone.

Carbon chain length

Classifies fatty acids by number of carbons.

Degree of saturation

Saturated, monounsaturated, or polyunsaturated

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Saturated fat

Solid at room temperature and lacks double bonds.

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Unsaturated fat

Liquid at room temperature and contains double bonds.

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Cis vs. Trans Geometry

Cis double bonds are on the same side; trans are on opposite sides.

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Dietary fat composition

Complex mix of saturated, monounsaturated, and polyunsaturated fats.

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Omega-3

Alpha-linolenic acid (18:3n3).

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Omega-6

Linoleic acid (18:2n6)

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Hydrogenation

Turning liquid vegetable oil into solid fat.

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Natural Trans Fats

Ruminant fats, includes CLA (18:2c9t11, 18:2t10c12) and vaccenic acid (18:1t11).

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Essential Fatty Acids (EFS)

Cannot be made in the body and must be obtained through diet.

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Two essential fatty acids

Alpha-linolenic acid (ALA, 18:3n3) and linoleic acid (LA, 18:2n6).

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ALA source

Can be used to synthesize EPA and DHA.

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EPA and DHA benefits

Role in reducing heart disease by reducing triglycerides.

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Arachidonic Acid (ARA)

Precursor for eicosanoids (leukotrienes and prostaglandins).

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Essential Fatty Acid Metabolism

Know desaturation, elongation, starting precursors, and final products.

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EPA and DHA sources

Found in fish and seafood, enriched in brain and eyes.

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Fatty acid pathway competition

Pathway shared between n6 and n3 fatty acids, competition possible.

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Mediterranean diet MUFA

Comprised of olive oil, rich in oleic acid (18:1c9 or 18:1n9).

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Phospholipids

Glycerol backbone + 2 fatty acids + phosphate head-group.

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Sources of sterols

Dietary cholesterol: from animals, not plants; plant sterols not absorbed.

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Uses of sterols

Sex hormones, adrenal hormones, Vit D, and bile.

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Cholecystokinin (CKK) and secretin

Both released when food enters duodenum by liver and stored in gallbladder.

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Micelle

Spherical compound made up of bile salts, phospholipids, fatty acids, cholesterol, monoglycerides.

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Short and medium chain fatty acids

Absorbed quickly and transported directly to liver via portal circulation.

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Storage of fat

Excess triglycerides stored in adipose tissue and muscle.

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Lipoprotein lipase

Acts on chylomicrons to release fatty acids for cellular reuptake.

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VLDL Function

Very low-density lipoprotein

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LDL Function

Low density lipoprotein

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HDL Function

High density lipoprotein

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Function of lipids

Cell membrane integrity, cell fluidity, and flexibility.

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DRI for fatty acids

Recommended to minimize saturated and trans (industrial) fats to lower heart disease risk.

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Lipids and cardiovascular disease

CVD: refers to coronary heart disease (CHD) and stroke.

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Statins

Cholesterol lowering drugs

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Read Siri-Tarino et al

Take home: saturated fat is not associated with heart disease, it 'was' the MUFA/PUFA that was missing from the diet

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Healthy fats

Take home: Saturated fats are good (not in excess), need more focus on getting MUFA and PUFA (healthy fats)

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What bout fat replacers?

Used to lower fat content

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Breakdown excess triglycerides

Products also water and CO2

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Study Notes

  • Lipids are water-insoluble molecules
  • Dietary fats are lipids consumed through food.
  • Three main lipid types: triglycerides, phospholipids, and sterols
  • Typical consumption: 70-100g triglycerides, 1g phospholipids, and 1g cholesterol daily

Triglycerides

  • Triglycerides consist of 3 fatty acids linked to a glycerol backbone
  • Fatty acids are classified by carbon chain length and degree of saturation
  • Carbon chain lengths are short (less than 6 carbons), medium (6-12 carbons, absorbed directly), or long (14 or more carbons)
  • Saturation levels include saturated or unsaturated (mono or poly)
  • Geometry of fatty acids is determined by saturation (cis or trans)

Fatty Acid Geometry

  • Saturated fats are solid, while unsaturated fats are liquid at room temperature
  • Geometry is determined by cis or trans double bonds
  • Most double bonds are cis
  • Two naming conventions exist: from carboxyl end using alpha carbon, or from methyl end using omega ('n')

Omega Fatty Acids

  • Omega-3 is alpha-linolenic acid (18:3n3)
  • Omega-6 is linoleic acid (18:2n6)
  • Omega-9 is oleic acid (18:1n9)

Dietary Fat Sources

  • Dietary fat is a mixture of saturated, monounsaturated, and polyunsaturated fats (SAFA/MUFA/PUFA)
  • Sources include avocado, butter, margarine, palm oil, egg yolk, ghee, olive oil, lard, vegetable oil, corn oil, grapeseed oil, peanut oil, sesame oil, fish oil, and coconut, sunflower.
  • Canola oil is a valuable Canadian export due to plant breeding efforts, with reduced erucic acid.
  • Canola oil is high in MUFA and alpha-linolenic acid, with newer varieties being high MUFA and low ALA

Trans Fats and Hydrogenation

  • Technology to solidify liquid vegetable oil is now prohibited for production/sale in Canada.
  • Partial hydrogenation converts unsaturated fats into a mixture of monounsaturated and saturated fats
  • Full hydrogenation converts unsaturated fats to saturated fats.
  • Trans fats were developed to replace saturated fats.
  • Trans fats are detrimental to heart health.

Trans Fats Regulations

  • Generally regarded as safe, GRAS status has been revoked by Canada and the US
  • Alternatives to trans fats are being produced, but health effects are unknown

Trans Fats - Natural Sources

  • Ruminant fats contain conjugated linoleic acid (CLA) and vaccenic acid
  • CLA and Vaccenic acid are found in dairy/beef fat - milk, cheese, beef
  • Vaccenic acid has anti-cancer effects
  • Tonalin (muscle-building properties) is effective in chicken, pig and rodents

Essential Fatty Acids

  • Essential fatty acids are obtained through diet as the body cannot produce them
  • Humans cannot insert double bonds past the 9th carbon
  • 2 EFA include Alpha-linolenic acid (ALA, 18:3n3) and Linoleic acid (LA, 18:2n6)
  • ALA is found in vegetables, soy, flaxseed, walnuts, avocados
  • ALA can be used to synthesize eicosapentaenoic acid (EPA, 20:5n3) and docosahexaenoic acid (DHA, 22:6n3)

EPA and DHA

  • EPA and DHA reduce heart disease by reducing triglycerides.
  • EPA and DHA has some evidence for anti-inflammatory effects
  • LA can be converted to arachidonic acid (AA or ARA, 20:4n6)
  • ARA is a precursor for eicosanoids
  • LA may reduce LDL-c and total cholesterol

Essential Fatty Acid Deficiency

  • Key components to know are desaturation, elongation, starting precursors, and final products.
  • 20:4n6 found in animal fats
  • 20:5n3 (EPA) / 22:6n3 (DHA) are found in fish and seafood
  • DHA is enriched in the eyes and brain, especially during the last trimester
  • Multiple pathways allow for a variety of end products, inefficiencies exist with less than 1% conversion
  • Mammals have low conversion rates but are higher in chickens and rats/mice.

EFAD Effects

  • Deficiency is rare due to the high availability of plant oils containing LA and ALA
  • Pathways are shared between n6 and n3 fatty acids, competition is possible
  • There is more n6 than n3 in the Canadian American diet (10:1 to 20:1 ratio)

MUFA

  • Key component of the mediterranean diet
  • The mediterranean diet is comprised of olive oil, rich in oleic acid (18:1c9 or 18:1n9).
  • Canola oil was high in oleic to begin with, but now even higher (at the expense of ALA, 18:3n3)
  • Produce de novo from stearic acid, 18:0 via desaturation to make 18:9
  • Some evidence that some MUFA produce de novo has unique biological properties

Lipokines

  • Some evidence that some MUFA produce de novo has unique biological properties
  • Le. 16:1c9, lipokine, sensitizes muscle action of insulin
  • Lipokines are made from 16:0 (palmitic acid); 16:1 from diet is different from de novo synthesis

Phospholipids

  • Phospholipids consist glycerol backbone + 2 fatty acids + phosphate head-group
  • Phospholipids are soluble in water
  • Phospholipids play a role in fat transport
  • Phospholipids are the main part of cell membranes and aid in digestion of dietary fat

Lecithin

  • In the liver, lecithin (choline) combines with bile salts to make bile

Sterols

  • Sterols are characterized by a 4 ring structure
  • Sterols sources include dietary cholesterol from animals, NOT plants.
  • Sterols from plant (cholesterol) are not absorbed.

Cholesterol Synthesis

  • De novo synthesis is ~1g/day, requirement ~1g/day
  • The liver acts as a thermostat to maintain cholesterol homeostasis
  • Blood cholesterol is more important than dietary cholesterol
  • Uses include sex hormones, adrenal hormones, Vit D and bile
  • Approved health claim for plant sterols: reduce blood cholesterol, linked to heart disease

Fat Digestion

  • Fat digestion begins in the small intestine
  • Cholecystokinin (CKK) and secretin are released when food enters the duodenum by the liver and is stored in the gallbladder
  • Bile is required for emulsification of fat into small droplets

Fat Enzymes

  • Pancreatic enzyme: breakdown of fat into 2 fatty acids and a monoglyceride
  • Cholesterol esterase: breakdown of cholesterol to free cholesterol and 1 fatty acid
  • Phospholipase: breakdown of phospholipids into 1 fatty acid and lysophospholipid

Micelle

  • Fat is absorbed as micelle, a spherical compound of bile salts, phospholipids, fatty acids, cholesterol, monoglycerides
  • Micelles transport lipid into enterocytes for absorption
  • Within enterocytes, lipids are resynthesized into intact triglycerides and packed as a lipoprotein, specifically a chylomicron
  • Chylomicrons transport lipids in circulation to tissues after a meal

Short and Medium Chain Fatty Acids

  • Absorbed easily and are transported directly to the liver via portal circulation
  • Are not packaged into chylomicrons, they are a ready source of energy for growing infants
  • Aka MCTs (medium chain triglycerides)
  • Breast milk is high in MCTs

Fat Storage and transportation

  • Excess triglycerides stored in adipose tissue and muscle
  • Lipoprotein lipase at the cellular level acts on chylomicrons to release fatty acids for cellular reuptake
  • In addition to chylomicrons that transport fat after a meal, there are other lipoproteins

Lipoproteins

  • Chylomicrons: transport dietary lipids
  • Very low-density lipoprotein (VLDL): mostly triglycerides from liver
  • Low density lipoprotein (LDL): mostly cholesterol, responsible for forward cholesterol transport (out to peripheral tissues)
  • High density lipoprotein (HDL): mostly apoproteins, reverse cholesterol transport (back to central body and waste)
  • good cholesterol

Lipid information

  • See fig 5,10 for details
  • See fig 5,10
  • LDL-c, aka bad cholesterol, HDL-c aka good cholesterol

Function of Lipids

  • Lipids provide energy, 9 kcal/g, source of 30-70% of energy used at rest by muscle/organs
  • Glycogen stores can only last 1-2 days, therefore fat is an essential long-term source of energy
  • Lipids aid in both absorption (aka part of micelles) and transport of fat soluble vitamins (A, D, E, and K)
  • Essential for Cell membrane integrity, cell fluidity, and flexibility
  • Transmission of nerve impulses
  • Protection of organs
  • Insulation of the body
  • Provides flavour, texture to food
  • Lipids Make us feel satiated

Fat Intake

  • AMDR: 20-35%
  • Active people need more energy from carbs; therefore, lower fat intake to 20-25% of energy

DRI for Fatty Acids

  • There is no DRI for saturated fat
  • Recommended to minimize saturated and trans (industrial) fats to lower heart disease risk
  • Less than 10% of energy from saturated fat
  • Reduce trans to absolute minimum
  • DRI for linoleic acid (18:2n6): AMDR of 5-10% of energy
  • DRI for alpha linolenic acid (18:3n3): AMDR of 0.6-1.2% of energy
  • No DRI for EPA/DHA, not essential
  • No DRI for cholesterol, made de novo in the liver
  • no DRI for MUFA

Types of Fats

  • Visible: fats we add to foods
  • Invisible: hidden within foods, occur naturally or added during processing
  • CVD: refers to coronary heart disease (CHD) and stroke
  • CHD and stroke are the second and third leading causes of death in Canada
  • High blood cholesterol, not dietary cholesterol linked to heart disease, is linked to heart disease

Target Blood Levels

  • Total cholesterol <5.2mmol/L
  • LDL-c <3.5, HDL >1.0 for men and 1.33 for women
  • Triglyceride <1.5

Treatment for High Cholesterol

  • American heart association recommends statins (cholesterol lowering drugs) for anyone at risk based on the highest quality drug trials (no diet studies)

Evidence for Diet

  • Evidence suggests we were partly right: Its not what is present, but what is missing. the High unsaturated fat (PUFA better than MUFA) reduces LDL-c.
  • forgot about/ignored role of MUFA/PUFA

Saturated Fats

  • Take home: Saturated fat is not associated with heart disease, it was the MUFA/PUFA that was missing from the diet
  • Saturated fats are good (not in excess), need more focus on getting MUFA and PUFA (healthy fats)
  • le. canola oil, fish oil

What about Fat Replacers

  • Replacers are used to lower fat content
  • Found in chips, cakes, cookies
  • le. olestra (not currently in CAD market)
  • Generally safe to consume at low levels, but may cause GI side effects

Losing Fat

  • Breakdown excess triglycerides by beta-oxidation making ATP
  • Break down products into water and CO2
  • The lungs are the primary excretory organ for fat

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