M1 Biochemistry: Fatty Acids & Complex Lipids

Front 1

Back 1

Hint 1

Acetic Acid

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Back 2

Hint 2

propionic (propanoic) acid

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Back 3

Hint 3

butyric acid

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Back 4

Hint 4

lauric (dodecanoic) acid

Front 5

Fatty acids are stored and transported as _________ commonly known as fats (solid) or oils (liquid).

Back 5

glycerol esters

Front 6

A 16- carbon saturated fatty acid is called....
A. Lauric Acid
B. Palmitic Acid
C. Stearic Acid

Back 6

B. Palmitic Acid, or Hexadecanoic Acid

Note: Lauric Acid is dedecanoic and Stearic Acid is octadecanoic

Front 7

Stearic acid is a saturated fatty acid with how many carbons?

Back 7

Stearic acid is also known as octadecanoic acid, and has 18 Cs.

Front 8

Regarding the pathophysiology of saturated fatty acids,a high dietary intake is associated with:

A. decreased LDL, increased HDL, an decreased risk of artheroscleriosis.

B. increased LDL, decreased HDL, increased risk of atherosclerosis.

Back 8

B!

Saturated F.A.s are baaad!

Front 9

Fatty acids can have cis or trans unsaturation. Though naturally unsaturated fatty acids are predominantly what type?

Back 9

Cis

Trans fatty acids have different physical properties.
Trans fatty acids have different biological activities (similar to saturated fatty acids). Trans fatty acids in diet are a problem we are currently facing as a society.

Front 10

Which Fatty Acid is the exception to the general rule that trans fatty acids are bad for you?

Back 10

Conjugated Linoleic Acid

Front 11

The most commonly occurring unsaturated fatty acids in mammals have how many carbons? Name some.

Back 11

Front 12

What is another way to write oleic acid?

(structure, or other notations)

Back 12

Front 13

What is another way to write linoleic acid?

(structurally or notation-wise)

Back 13

Front 14

What is another way to write linolenic acid?

(structurally or notation wise)

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Front 15

Of the three examples mentioned in lecture of the most commonly occurring UNSATURATED F.A.s in mammals, name the one(s) that are essential fatty acids.

Back 15

Only Linoleic and Linolenic Acids!

Front 16

_____________ are highly unsaturated 20-carbon fatty acids.

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Eicosonoic Acids

Front 17

Fish oil is

A. PGE 1 precursor
B. PGE 2 precursor
C. PGE 3 precursor

Back 17

C. PGE3 precursor

Front 18

Arachidonic Acid is

A. an essential 18-carbon fatty acid
B. PGE 2 precursor
C. also known as fish oil

Back 18

B. PGE2 precursor

Hint 18

note: A. refers to linoleic and linolenic acids (all cis-9, 12-octadecenoic acid and all cis-9, 12, 150 octadecenoic acid, respectively)
C. refers to PGE 3 precursor

Front 19

True or False:
Docosahexaenoic acid lowers the risk of CHD and is an important constituent of membranes.

Back 19

True, DHA is important for retina, testis and brain. So fish really is brain food. DHA is also a precursor for transmitter substances called resolvins that are important in signaling pathways and in brain.

Front 20

Which of the following dietary components will help to alleviate the symptoms of essential fatty acid deficiency?

A. Lauric acid
B. Palmitic acid
C. Stearic acid
D. Oleic acid
E. Linoleic acid

Back 20

E. Linoleic Acid

Front 21

How does the following influence melting point for fatty acids?

A. increased carbons
B. increased level of unsaturation
C. increased level of saturation

Back 21

A. increased carbons = increased melting point
B. increased unsaturation = decreased melting point
C. increased saturation = increased melting point

Front 22

Which of the following has the highest melting point?

A. Arachidic acid (20:0)
B. Arachidonic acid
C.Stearic acid
D. Oleic acid
E. Linoleic acid

Back 22

A. Arachidic acid (20:0)

it has the longest carbon chain and is the most saturated!

Front 23

Fatty acids are amphiphiles, forming _______ at alkaline pH.

Back 23

micelles

Front 24

True or False:

The monomolecular solubility of fatty acids is very high at physiological pH.

Back 24

False! Fatty acids are amphiphiles, forming micelles at alkaline pH.

Front 25

List the reactions fatty acids are involved in:
3 involving the carboxyl group and 2 involving double bonds

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carboxyl group: esterfication, amidation, hydrolysis

double bonds: hydrogenation, autooxidation

Front 26

True or False:

Saturated fatty acids are more stable than unsaturated fatty acids.

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True

Front 27

Name some disadvantages of fatty acid hydrogenation.

Back 27

Increased saturated fat content, Altered biological activity (hydrogenation changes biological activity), Cis-trans and positional isomerization (partial hydrogenation only)

Front 28

List undesirable effects of lipid autooxidation for food (2) and in vivo (3).

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In foods:
Toxic products (free radicals, aldehydes)
Unpleasant odors, flavors (aldehydes, organic acids)

In vivo:
Membrane damage
Dysfunctional lipoproteins
Toxic products (aldehydes, polymers)

Front 29

Susceptibility of a fatty acid to autooxidation increases about how much for each double bond?

Back 29

10-fold!

Front 30

True or False:

Hydrogenation of an unsaturated fatty acid increases its stability by making it less susceptible to autooxidation.

Back 30

True! Autooxidation is off double bonds. Hydrogenation rids the double bonds. Thus, it is true.

Front 31

___________________ may occur with many different fatty acid compositions, depending on the source. Their physical properties will depend on the properties (chain length, unsaturation) of their constituent fatty acids. If solid at room temperature, they are called fats; if liquid, they are called oils.

Back 31

Triacylglycerols (aka triglycerides)

Front 32

What is this and what is its biological importance?

Back 32

A ganglioside. Their biological importance includes: giving specific character of the cell surface (blood group markers, differentiation markers, cell-cell interactions, pit receptors). Know that it has a lot of sialic acids.

Front 33

What is this and what is its biological significance?

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This is a cholesterol structure. Relationship to atherosclerosis and CHD, membrane constituent, precursor to bile acids, steroid hormones and vitamin D, Oxysterols are key participants in signaling pathways (LXR).

Front 34

This is the major route for removal of cholesterol from the body.

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The liver oxidizes about 500 mg/day of cholesterol to bile acids. This is the major route for removal of cholesterol from the body.

Front 35

_____________ are biologically active metabolites of cholesterol synthesized in gonads and adrenals.

A. Steroid hormones
B. Bile Acids
C. Gangliosides

Back 35

A. Steroid hormones

The mass of cholesterol converted to androgens, estrogens, glucocorticoids and mineralocorticoids is very small in comparison to bile acid synthesis.

Front 36

_____________ are metabolites of cholesterol that function as biological detergents in fat digestion.

A. Steroid hormones
B. Bile acids
C. Gangliosides

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B. Bile Acids


The liver oxidizes about 500 mg/day of cholesterol to bile acids. This is the major route for removal of cholesterol from the body.

Front 37

What are metabolites of cholesterol? Which one is produced more?

Back 37

Bile acid and Steroid hormones.

The mass of cholesterol converted to androgens, estrogens, glucocorticoids and mineralocorticoids is very small in comparison to bile acid synthesis.

Front 38

The major route for removal of cholesterol from the body is:

A. Steroid hormone synthesis
B. Sloughing of skin cells
C. Bile acid synthesis
D. Secretion from the kidneys

Back 38

C. Bile acid synthesis

Front 39

Regarding nomenclature for modified carboxyl group, how do you name:

A. a protonated 18C saturated fatty acid chain?
B. and what about if it were ionized?

Back 39

An 18 C saturated fatty acid that is protonated is STEAR[IC] acid and if that's ionized it is called STEAR[ATE].

Front 40

How would you name a derivatized fatty acid , say if a methyl group was added to the carboxcylic end of a 16C fatty acid chain?

Back 40

methyl palmitate


(the formula is X- [acid]-ate)

Front 41

How would you name anothe rcompound derivatized with fatty acid such as a glycerol with an oleaic acid at the 1 position?

Back 41

1-oleoylglcerol

(the other way to name this would be glyceryl-1-oleate)

Front 42

Reagrding glycerol-based lipids, physical properties depend on component fatty acids (chain length and unasturation). In general, solid fats will have a [ higher / lower ] content of saturated or trans unsaturated fatty acids.

Back 42

higher


(either shorter chain or unsaturation may lower melting point)

Front 43

What general glycerol-based lipid is this a picture of? Then name this compound.

Back 43

This is a phosphoglyceride , 1-palmitoyl-2-oleoylphosphatidic acid

Front 44

Name this!

Back 44

1-palmitoyl-2linoleoylphosphatidylethanolamine

Front 45

Name this

Back 45

1-palmitoyl-2-linoleoylphosphatidylcholine


aka phosphatidylcholine

Front 46

Name this

Back 46

1-palmitoyl-2-linoleoylphosphatidylserine


aka phosphatidylserine

Front 47

Name this

Back 47

1-palmitoyl-2-linoleoylphosphatidylinositol


aka phosphatidylinositol

Front 48

Label the the phospholipase cutting points.

Back 48

Front 49

What are each of these called?

Back 49

top: sphingosine
middle: ceramide
bottom: sphingomyelin

Front 50

What is this a picture of?

Back 50

Ganglioside

(remeber, this has a lot of sialic acid)

Front 51

What is this?

Back 51

cholesterol

Front 52

Which complex lipid's major physiological importance includes:
major storage form of energy in mammals and plant seeds as well as important intracellular second messengers?

A. Acylglycerols
B. Cholesterols
C. Gangliosides
D. Phosphoglycerides
E. Sphingomyelin

Back 52

A. Acylglycerols

Front 53

Which complex lipid's major physiological importance includes:
major structural component of membranes, lipoproteins, and intracellular lipid storage droplets, as well as components of signaling pathways?

A. Acylglycerols
B. Cholesterols
C. Gangliosides
D. Phosphoglycerides
E. Sphingomyelin

Back 53

D. Phosphoglycerides

Front 54

Which complex lipid's major physiological importance includes:
membrane constituent (w similar chemical/physical properties as choline and serine phosphoglycerides) as well as a direct relationship in the ratio of this to cholesterol in a membrane, particularly "lipid rafts"?

A. Acylglycerols
B. Cholesterols
C. Gangliosides
D. Phosphoglycerides
E. Sphingomyelin

Back 54

E. Sphingomyelin

Front 55

Which complex lipid's major physiological importance includes:
membrane constituent responsible for general negative charge and specific cell surface characteristics? (Thus also involved in receptor-ligand interaction, cell recognition, and blood group determination.)

A. Acylglycerols
B. Cholesterols
C. Gangliosides
D. Phosphoglycerides
E. Sphingomyelin

Back 55

C. Gangliosides

Front 56

Which complex lipid's major physiological importance includes:
produces metabolites bile acid and steroid hormones, is a constituent of cellular membranes in mammals, and elevated this in blood is a major risk factor for CHD and atherosclerosis?

A. Acylglycerols
B. Cholesterols
C. Gangliosides
D. Phosphoglycerides
E. Sphingomyelin

Back 56

B. Cholesterols