Lipids Chemistry Lecture 3

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Questions and Answers

What is the primary role of glycine or taurine in the biosynthesis of bile acids?

  • They act as precursors for the bile acid molecules.
  • They help conjugate bile acids enhancing their solubility. (correct)
  • They promote the absorption of bile acids in the intestine.
  • They enhance bile acid's reactivity with cholesterol.

Which statement about the structure of cholic acid is correct?

  • It is a non-conjugated bile acid with no polar groups.
  • It has three hydroxyl groups located at positions 3, 7, and 12. (correct)
  • It contains two hydroxyl groups and one carboxyl group.
  • Its structure has an amine group replacing one of the hydroxyl groups.

In what form are conjugated bile acids primarily found in the duodenum?

  • In their deprotonated form, enhancing solubility. (correct)
  • As non-conjugated acids for better emulsification.
  • Fully protonated and water soluble.
  • As solid salts that require heating to dissolve.

What distinguishes sodium cholate from non-conjugated bile acids?

<p>Sodium cholate is a conjugated bile salt containing Na+. (C)</p> Signup and view all the answers

Which of the following accurately describes bile acid conjugation?

<p>Conjugation occurs in liver cells and increases bile acid's water solubility. (B)</p> Signup and view all the answers

What is the primary function of lipoproteins in the body?

<p>To transport lipids between the liver and peripheral tissues (A)</p> Signup and view all the answers

Which lipoprotein is characterized as being the largest and having the lowest density?

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

What type of lipids are predominantly found in low-density lipoproteins (LDL) and high-density lipoproteins (HDL)?

<p>Cholesterol and phospholipid (PL) (D)</p> Signup and view all the answers

What is the role of apoproteins in lipoproteins?

<p>To span the lipoprotein structure and interact with lipid layers (C)</p> Signup and view all the answers

Which lipoprotein has the highest ratio of protein to lipid?

<p>High-density lipoproteins (HDL) (B)</p> Signup and view all the answers

Which component forms the outer layer of a lipoprotein particle?

<p>Phospholipids and unesterified cholesterol (A)</p> Signup and view all the answers

What characteristic makes chylomicrons unique compared to other lipoproteins?

<p>They have the highest lipid content and are the largest (A)</p> Signup and view all the answers

What is one of the main roles of HDL cholesterol in the body?

<p>Increases the rate of reverse cholesterol transport (C)</p> Signup and view all the answers

Which of the following describes the function of acyl-CoA-cholesterol acyl transferase (ACAT)?

<p>Esterifies cholesterol with fatty acids (D)</p> Signup and view all the answers

What is considered an optimal level of LDL cholesterol in adults, according to the guidelines?

<p>Less than 100 mg/dL (D)</p> Signup and view all the answers

Which type of cholesterol is primarily associated with vasculoprotection?

<p>HDL cholesterol (D)</p> Signup and view all the answers

What is the typical fate of cholesterol synthesized in the liver?

<p>It can be esterified, exported or converted into bile acids (D)</p> Signup and view all the answers

Which component is NOT typically associated with steroids?

<p>Fatty acid side chains (C)</p> Signup and view all the answers

For triglycerides, which level is considered optimal?

<p>10-150 (B)</p> Signup and view all the answers

Which of the following statements about steroid structures is true?

<p>They have a four-ring core with multiple substituent groups (D)</p> Signup and view all the answers

What is the desirable total cholesterol level in mg/dL for adults?

<p>Less than 200 mg/dL (C)</p> Signup and view all the answers

What transformation occurs as VLDL degrades in circulation?

<p>VLDL transforms into IDL (C)</p> Signup and view all the answers

What is the primary role of LDL particles in the body?

<p>To provide cholesterol to peripheral tissues (B)</p> Signup and view all the answers

What percentage of LDL is transported back to the liver?

<p>60% (B)</p> Signup and view all the answers

What process is facilitated by HDL particles to benefit the body?

<p>Reverse cholesterol transport (A)</p> Signup and view all the answers

How does nascent HDL particle mature?

<p>By accumulating phospholipids and cholesterol from blood vessel linings (D)</p> Signup and view all the answers

What effect does elevated LDL levels have on health?

<p>Leads to the formation of atherosclerotic plaques (B)</p> Signup and view all the answers

What happens to cholesterol from HDL after it reaches the liver?

<p>It can be converted to bile salts or excreted into bile (D)</p> Signup and view all the answers

Which component is NOT a part of nascent HDL structure?

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

Which tissues primarily receive cholesterol from LDL for steroid hormone synthesis?

<p>Adrenocortical and gonadal cells (A)</p> Signup and view all the answers

What effect does high levels of cholesterol in the blood have on the body?

<p>Leads to precipitation and atherosclerosis (C)</p> Signup and view all the answers

What is the role of low density lipoproteins (LDL) in the body?

<p>Transport cholesterol from liver to tissues (D)</p> Signup and view all the answers

Which compound is a precursor to vitamin D3?

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

Which of the following statements about bile acids is accurate?

<p>Bile acids are polar derivatives of cholesterol (B)</p> Signup and view all the answers

How are bile acids primarily found in the body?

<p>Mainly in the bile of mammals (D)</p> Signup and view all the answers

What nutrient deficiency results from insufficient sunlight exposure?

<p>Vitamin D3 (D)</p> Signup and view all the answers

Bile salts are formed by the conjugation of bile acids with which of the following?

<p>Taurine or glycine (B)</p> Signup and view all the answers

What is the estimated daily synthesis of bile salts?

<p>600 mg (A)</p> Signup and view all the answers

Which type of cholesterol is associated with a higher risk of heart attack?

<p>Cholesterol transported by LDL (C)</p> Signup and view all the answers

What structure do all bile acids possess?

<p>A hydroxyl group at carbon number 3 (D)</p> Signup and view all the answers

Flashcards

What are lipoproteins?

Lipoproteins are spherical particles that transport lipids (triacylglycerols and cholesterol) in the body. They are composed of a core of hydrophobic lipids surrounded by a monolayer of phospholipids and free cholesterol, with apoproteins embedded in the outer layer.

What are the 4 main types of lipoproteins?

Chylomicrons, very-low-density lipoproteins (VLDL), low-density lipoproteins (LDL), and high-density lipoproteins (HDL) are the four main types of lipoproteins.

What makes up the outer layer of a lipoprotein?

The outer layer of a lipoprotein consists of a monolayer of phospholipids and free cholesterol, with their charged groups facing outwards towards the water molecules.

What makes up the core of a lipoprotein?

The core of a lipoprotein is composed of hydrophobic lipids, primarily esterified cholesterol and triacylglycerol.

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What are apoproteins and their function?

Apoproteins are proteins embedded in the lipoprotein structure. They span the region between the core and the outer envelope, with some parts exposed at the surface.

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How are lipoproteins classified?

Lipoproteins are classified based on density, which is determined by their ratio of protein to lipid. Chylomicrons are the least dense and largest, while HDL is the densest and smallest.

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What is the main function of each lipoprotein class?

Chylomicrons primarily transport triacylglycerols, while LDL predominantly carries cholesterol. HDL is involved in reverse cholesterol transport, removing excess cholesterol from peripheral tissues and returning it to the liver.

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What is the process of LDL formation?

VLDL particles lose triacylglycerols, transforming into intermediate-density lipoproteins (IDL). Further loss of triacylglycerols leads to the formation of LDL.

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What is the main function of LDL?

The primary function of LDL is to deliver cholesterol to cells throughout the body, especially those needing it for steroid hormone synthesis.

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Where does LDL go after delivering cholesterol?

LDL particles are rich in cholesterol and cholesterol esters. About 60% is returned to the liver, while the remaining 40% goes to tissues like adrenal glands and gonads for steroid hormone production.

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What are the health implications of high LDL levels?

High levels of LDL in the bloodstream contribute to the formation of atherosclerotic plaques, which can lead to heart disease.

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How are HDL particles synthesized?

HDL particles can be created by the liver and intestines as small molecules with a shell composed of phospholipids, cholesterol, and apoproteins.

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Describe the maturation process of HDL.

Nascent HDL particles accumulate phospholipids and cholesterol from blood vessel walls, growing larger and more globular. This transformation leads to mature HDL.

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What is reverse cholesterol transport?

HDL particles remove excess cholesterol from cells and transport it back to the liver for breakdown or excretion. This process is crucial for maintaining healthy cholesterol levels.

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Why is HDL considered 'good cholesterol'?

HDL is known as 'good cholesterol' because it helps lower blood cholesterol levels by removing excess cholesterol from circulation.

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Explain the role of HDL in cholesterol metabolism.

HDL particles transport cholesterol from peripheral tissues back to the liver, where it can be utilized for bile salt synthesis or excretion.

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Benefits of HDL cholesterol

High levels of HDL in the blood help reduce the risk of heart disease by facilitating the movement of cholesterol away from blood vessels and towards the liver for processing.

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How does HDL prevent cholesterol loss?

HDL cholesterol helps prevent cholesterol from leaving the HDL particle by attaching a fatty acid to it.

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What are the fates of cholesterol synthesized in the liver?

Cholesterol synthesized in the liver can be stored as cholesterol esters within lipid droplets, packaged into lipoproteins for transport to tissues, or converted into bile acids for fat absorption.

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What does ACAT do?

ACAT (Acyl-CoA-cholesterol acyl transferase) is an enzyme that attaches a fatty acid to cholesterol, converting it into a cholesterol ester.

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What are steroids?

Steroids are a class of lipids found in plants and animals. They share a common core structure called the steroid nucleus.

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What is the steroid nucleus composed of?

The steroid nucleus consists of 17 carbon atoms arranged in four fused rings, with two methyl groups.

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What makes a steroid a sterol?

Sterols, like cholesterol, have a hydroxyl group attached to carbon 3 and a side chain attached to carbon 17.

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What are bile acids?

Bile acids are steroids that aid in fat digestion. They are formed from cholesterol in the liver.

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What are steroid hormones?

Steroid hormones regulate various physiological processes.

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What is conjugation of bile acids?

Conjugation is a process where bile acids are modified by attaching either glycine or taurine to their structure. This process increases their water solubility, making them more effective at emulsifying fats in the digestive tract.

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What is vitamin D?

Vitamin D is a steroid involved in calcium absorption and bone health.

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What are bile salts?

Bile salts are the conjugated forms of bile acids that are present in bile. They are more water-soluble than their unconjugated counterparts and are essential for the efficient digestion and absorption of fats.

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Why is conjugation important for bile acid function?

The conjugation of bile acids with glycine or taurine increases their water solubility. This is essential for proper fat digestion and absorption because bile acids need to be dissolved in the aqueous environment of the digestive tract to effectively emulsify fats.

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How do bile acids facilitate fat digestion?

Bile acids are stored in the gallbladder and released into the small intestine. This release is triggered by the presence of fat in the diet. The bile acids emulsify fats, breaking them down into smaller droplets, which allows pancreatic lipase to effectively digest them.

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What is cholesterol?

Cholesterol is a sterol, an important component of animal cell membranes, crucial for maintaining membrane fluidity and structure. It is also a precursor to vital hormones like testosterone, estrogen, and cortisol.

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Why is cholesterol less flexible than other lipids?

Cholesterol's fused ring system makes it less flexible compared to other lipids.

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What happens when cholesterol levels are high in the blood?

High levels of cholesterol in the blood can lead to its accumulation in blood vessel walls, a condition called atherosclerosis. This buildup can restrict blood flow and increase the risk of heart disease.

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How is cholesterol stored and transported in the body?

Cholesterol is converted into cholesteryl esters by attaching a fatty acid to its C-3 hydroxyl group. This form is used for storage and transport in the blood.

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How is vitamin D3 produced and what is its role?

7-dehydrocholesterol, a precursor to vitamin D3, is stored under the skin and converted to cholecalciferol (vitamin D3) by exposure to sunlight. Vitamin D3 plays a role in calcium absorption and bone health.

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What is the role of LDL in cholesterol transport?

Low-density lipoproteins (LDL) transport cholesterol from the liver to the tissues, often referred to as 'bad cholesterol' due to its association with a higher risk of heart disease.

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What is the role of HDL in cholesterol transport?

High-density lipoproteins (HDL) transport cholesterol from the blood back to the liver, where it can be metabolized. HDL is often called 'good cholesterol' due to its association with a lower risk of heart disease.

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What are bile acids and what is their function?

Bile acids, synthesized from cholesterol in the liver, are hydroxylated steroids essential for fat digestion. These amphipathic molecules aid in emulsifying fats, making them easier to digest and absorb.

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How are bile salts formed and what is their importance?

Bile acids are conjugated with taurine or glycine residues to form bile salts, which contribute to their amphipathic nature and enhance their digestive function.

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How are bile acids classified and what is their significance?

A diverse range of bile acids are synthesized and classified into primary, secondary, conjugated, and non-conjugated types based on their structural differences. Bile acids are essential for lipid metabolism and overall digestive health.

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Study Notes

Lipids Chemistry Lecture 3

  • Plasma Lipoproteins:
    • Lipoproteins transport lipids (triacylglycerols and cholesterol) from the small intestine or liver to peripheral tissues, then back to the liver.
    • Lipoproteins vary in the ratio of proteins to lipids and the specific apoproteins and lipids they contain.
    • Lipoprotein particles include chylomicrons, very-low-density lipoproteins (VLDL), low-density lipoproteins (LDL), and high-density lipoproteins (HDL).

Lipoprotein Structure

  • Lipoproteins are spherical complexes of lipids and specific proteins (apoproteins).
  • Outer coat:
    • Apoproteins
    • Phospholipids (PL)
    • Unesterified cholesterol
  • Inner core:
    • Triacylglycerol (TAG)
    • Cholesteryl ester (CE)

Size and Density of Lipoproteins

  • Lipoprotein size and protein-to-lipid ratio determine density, measured by density gradient centrifugation.
  • Chylomicrons (CM) are the largest and least dense, containing the most lipid and least protein.
  • VLDL and LDL are successively denser, with higher protein-to-lipid ratios.
  • HDL particles are the densest.
  • TAG is the main lipid in chylomicrons and VLDL, while cholesterol and phospholipids are predominant in LDL and HDL.

Composition of Lipoproteins

  • The table shows the percentage composition of proteins and lipids in different lipoprotein classes (chylomicrons, VLDL, LDL, and HDL).

Apoproteins

  • Apoproteins, or apolipoproteins, are the protein components of lipoproteins.
  • Nine major apoprotein species (A, B, C, D, and E) and various sub-species exist.
  • Apoproteins have specific amino acid sequences, chain lengths, and different physiological/biochemical properties.
    • They maintain lipoprotein structure integrity.
    • They act as enzyme cofactors or inhibitors (e.g., apo C-II for lipoprotein lipase).
    • They act as ligands for interaction with lipoprotein receptors in tissues (e.g., apo B-100 and apo E for the LDL receptor).

Chylomicrons

  • Function: transport dietary lipids from the intestine to peripheral tissues.
  • Synthesis: Intestinal mucosal cells synthesize chylomicrons, which are secreted into the lymph and then blood.
  • Fate: Lipoprotein lipase (LPL) in capillary walls of adipose and muscle tissue digests the triacylglycerols in chylomicrons, releasing fatty acids for use by tissues (primarily muscle, heart, and adipose tissue).
  • Chylomicrons shrink and become enriched in cholesterol and proteins as they circulate.

VLDL

  • Function: transport lipids from the liver to peripheral tissues.
  • Origin: Produced in the liver, synthesis of triacylglycerols often from excess dietary glucose.
  • Formation of LDL: VLDL lose triacylglycerols as they circulate, transforming to IDL and eventually into LDL.

LDL

  • Function: deliver cholesterol to peripheral tissues.
  • Composition: Rich in cholesterol and cholesterol esters.
  • Fate: 60% of LDL is transported back to liver; the remaining 40% supplies cholesterol to extrahepatic tissues (like adrenocortical and gonadal cells) for steroid hormone synthesis.
  • Elevated LDL levels contribute to atherosclerosis plaque formation.

HDL

  • Function: remove cholesterol from peripheral tissues and return it to the liver (reverse cholesterol transport).
  • Formation: Nascent HDL is synthesized by the liver and intestine.
  • Maturation: HDL matures by accumulating cholesterol and phospholipids from cells lining blood vessels, transforming into a more globular shape.
  • Cholesterol transport: HDL accepts free cholesterol from peripheral tissues, converting it to cholesterol esters, transporting some to VLDL/IDL/LDL and returning to the liver; the rest is transferred directly in the HDL molecule.
    • HDL helps to lower blood cholesterol levels.

Reverse Cholesterol Transport

  • A major HDL function is reverse cholesterol transport, removing cholesterol from cells and returning it to the liver.
  • This process is crucial for reducing cellular cholesterol levels, particularly in vascular tissue.
  • Esterification of cholesterol within HDL prevents it from leaving.
  • High HDL levels are considered vasculoprotective.

Cholesterol

  • Desired values (NIH US):
    • LDL cholesterol optimal less than 100 mg/dL, borderline high 130-159 mg/dL
    • HDL cholesterol greater than 40-60 mg/dL
    • Total cholesterol desirable less than 200 mg/dL, borderline high 200-239 mg/dL
    • Triglycerides 10-150 mg/dL
    • VLDL 2-38 mg/dL
  • Cholesterol synthesis in the liver:
      1. Esterification with fatty acids forming cholesterol esters.
      1. Export to peripheral tissues via lipoproteins.
      1. Conversion to bile acids for fat digestion.

Steroids

  • Steroids are a group of plant and animal lipids that share a similar tetracyclic structure.
  • Steroid nucleus: Composed of 17 carbon atoms and two methyl groups (C18, C19).
  • Steroids include sterols, bile acids & salts, steroid hormones and vitamin D.
  • Sterols: Hydroxyl group at C-3, aliphatic side chain at C-17.
  • Cholesterol: A solid alcohol with 27 carbon atoms and a steroid nucleus.
  • Properties include: amphipathic, major component of cell membranes, precursor to other steroids.

Bile Acids

  • Bile acids are hydroxylated steroids synthesized from cholesterol by peroxisomal enzymes within liver cells.
  • Bile acids are conjugated to taurine or glycine to form bile salts.
  • Classification:
    • Primary (cholic and chenodeoxycholic acid)
    • Secondary (deoxycholic and lithocholic acid)
  • Functions:
    • Emulsify fats for digestion & absorption.
    • Prevent cholesterol precipitation in bile.
    • Major excretory pathway for cholesterol.
    • Act as signaling molecules affecting lipid and glucose metabolism.

Steroid Hormones

  • Diverse class of hormones with varying structures based on the steroid nucleus.
  • Categories include mineralocorticoids, glucocorticoids, sex hormones (male and female).
  • Production sites include adrenal cortex and gonads (testes or ovaries).
  • Role in regulating critical bodily functions and processes.

Clinical Correlation

  • Low-density lipoprotein (LDL) transports cholesterol to tissues (bad cholesterol).
  • High-density lipoprotein (HDL) transports cholesterol from tissues to liver (good cholesterol).
  • High LDL and low HDL are associated with elevated cardiovascular risk.

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