532 - Med Chem Ii - Exam Ii - Lipids & Antihyperlipidemia

Front 1

Roles of fatty acids (2)

Back 1

1) components of more complex membrane lipids & 2) components of stored fat in the form of triacylglycerols

Front 2

Describe the structural features of fatty acids

Back 2

1) even numbers of carbons
2) cis-double bonds only, separated by 1 carbon
3) defined by omega (start numbering form the last carbon)

Front 3

Essential fatty acids (definition and 2 examples)

Back 3

Humans cannot produce them (must get from diet) omega-3 and omega-6

Front 4

Structure of triacylglycerols

Back 4

glycerol + 3 fatty acids

Front 5

Structure of glycerophospholipids

Back 5

Glycerol + 2 fatty acids + PO4-X (polar)

Front 6

What are the two membrane lipids discussed in lecture?

Back 6

Glycerophospholipids and sphingolipids

Front 7

Structure of sphingolipids

Back 7

Sphingosine + non polar side chain+ fatty acid+ PO4+ choline or (mono/oligo) saccharide

Front 8

What is the main function of cholesterol?

Back 8

To modulate the fluidity of membranes by interacting with their complex lipid components

Front 9

How are cholesterol esters different from free cholesterol?

Back 9

1) less polar than free cholesterol and are preferred for transport in plasma and storage & 2) packed into lipid particles

Front 10

Do cholesterol esters contribute to membranes?

Back 10

NOOO

Front 11

Where is the ester of cholesterol esters located?

Back 11

Where the 3B -OH normally is

Front 12

How are cholesterol esters synthesized from cholesterol?

Back 12

1) Cholesterol + phosphatidylcholine, 2) | LCAT (lectithin cholesterol acyltransferase) & 3)Cholesterol Ester + lysophosphatidylcholine

Front 13

Are the BC and CD rings of cholesterol trans or cis fused?

Back 13

TRANS

Front 14

A-I is key apoprotein for which lipoprotein?

Back 14

HDL

Front 15

B-100 is key apoprotein for which lipoprotein?

Back 15

LDL

Front 16

HDL is made mostly of?

Back 16

proteins

Front 17

What is LDL mostly made of?

Back 17

Cholesterol

Front 18

What is VLDL mostly made out of?

Back 18

Triglycerides

Front 19

Chylomicrons are made mostly of?

Back 19

Triglycerides

Front 20

Primary functions of lipoproteins (2)

Back 20

1) Associate highly insoluble lipids with more polar ones like cholesterol and phospholipids, 2) Provide a trafficking mechanism for hydrophobic small molecules

Front 21

Which lipoprotein transports TG from intestines to other tissues?

Back 21

Chylomicrons

Front 22

Do chylomicrons transport TG to kidneys?

Back 22

NO

Front 23

Which lipoprotein transports TG to fat tissues?

Back 23

VLDL

Front 24

Which lipoprotein transports cholesterol to peripheral tissues?

Back 24

LDL

Front 25

Which lipoprotein transports cholesterol to the liver?

Back 25

HDL

Front 26

Which lipoprotein is bound to plasma cholesterol?

Back 26

HDL

Front 27

Are the chylomicrons part of the exogenous or endogenous pathway?

Back 27

EXOGENOUS- because carries TG from intestines.

Front 28

What is the only "nonexchangeable" apoprotein?

Back 28

B-100

Front 29

What is the function of B-100?

Back 29

lipid recognition and binding to LDL particle

Front 30

How does HDL transfer the cholesterol and cholesterol esters into the liver?

Back 30

It binds to scavenger receptor B1 (SR-B1) in hepatocytes

Front 31

Three stages of cholesterol biosynthesis

Back 31

1) Squalene generation from Acyl-CoA, 2) Cyclization of squalene to lanosterol, & 3) Conversion of lanosterol to cholesterol

Front 32

What is the enzyme that converts (S) B-hydroxyl-B-methylglutaryl-CoA to (R)-mevalonic acid?

Back 32

HMG-CoA Reductase

Front 33

What is the function of HMG-CoA reductase?

Back 33

Converts (S) B-hydroxyl-B-methylglutaryl-CoA to (R)-mevalonic acid in Step 1 of cholesterol biosynthesis (squalene production)

Front 34

What are the 4 strategies for controlling hyperlipidemia?

Back 34

1) diet, 2) biosynthesis, 3) bile acid sequestration, 4) lipoprotein catabolism

Front 35

Mechanism of action of fibrates

Back 35

Agonists of PPAR alpha

Front 36

What are the effects of fibrates?

Back 36

Decreases serum TG and VLDL

Front 37

What are phenolic ethers?

Back 37

Fibrates

Front 38

PPAR alpha

Back 38

Peroxisome proliferator activated receptor alpha (fibrates agonize it)

Front 39

Name the two fibrate prodrugs

Back 39

Clofibrate and Fenofibrate

Front 40

What is the mechanism of action of bile acid sequestrants?

Back 40

"positively charged nitrogen atoms sequester bile acid reabsorption, when the body senses lower bile, degrades cholesterol to make more"

Front 41

Effects of bile acid sequestrants

Back 41

Lower serum LDL

Front 42

Properties of bile acid sequestrates (3)

Back 42

1) Anion exchange resins, 2) water insoluble and inert to digestive enzymes, & 3) not absorbed through the GI tract

Front 43

What is Ezetimibe's mechanism of action?

Back 43

Ezetimibe inhibits the sterol influx transporter of the intestine, NPC1L1, preventing the absorption of cholesterol from the diet.

Front 44

Effects of Ezetimibe

Back 44

reduces serum LDL and increases HDL

Front 45

NPC1L1

Back 45

a sterol influx transporter located in the apical membrane of the enterocyte (inhibited by Ezetimibe)

Front 46

Mechanism of action of statins

Back 46

Mimics the product of HMG-CoA reductase to prevent cholesterol biosynthesis (step 1)

Front 47

Fungal metabolite statins (3)

Back 47

Lovastatin, Pravastatin, & Simvastatin

Front 48

Synthetic Statins (4)

Back 48

Fluvastatin, Cerivastatin, Atorvastatin, & Rosuvastatin

Front 49

Which fungal metabolite accumulates faster in peripheral tissues?

Back 49

Pravastatin

Front 50

Why isn't cerivastatin used anymore?

Back 50

It had the highest bioavailability, which also meant it had the highest incidence of side effects, most notably rhabdomyolysis or weakening of skeletal muscle

Front 51

Do the fungal or synthetic metabolites have chiral centers?

Back 51

Fungal- complex in nature

Front 52

Pravachol (aka)

Back 52

Pravastatin

Front 53

Lipitor (aka)

Back 53

Atorvastatin

Front 54

Which class has a decalin?

Back 54

The statins