Lipid Chemistry (ppt) Flashcards

1
Q

It is the fraction of any biological material that is 💡insoluble in water but 💡soluble in one or more solvents of low polarity.

A heterogenous group of compounds that include fatty acids, fats and oils, waxes, steroids, phospholipids & sphingolipids.

A

Lipid

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2
Q

What are the two major functions of lipids?

A
  1. Source of energy

2. Important component of cellular structure

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3
Q

Classification of Lipids:

A
  1. Simple lipids
  2. Complex lipids
  3. Precursor and derived lipids
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4
Q

These are classification of lipids which contains 💡esters of fatty acids with 💡various alcohols

A

Simple lipids

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5
Q

It is a simple lipid which contain 💡esters of fatty acids with 💡glycerol

A

Triacylglycerol (triglycerides)

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6
Q

These are simple lipids which contain 💡esters of fatty acids with 💡higher molecular weight monohydric
alcohols

A

Waxes

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7
Q

These are classification of lipids which contains 💡esters of fatty acids with 💡various alcohols plus an 💡additional functional group.

A

Complex (Compound) Lipids

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8
Q

These are complex lipid where there is a 💡phosphate group present.

A

Phospholipids

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9
Q

These are complex lipid which contain 💡carbohydrates

A

Glycolipids

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10
Q

These are complex lipid which are 💡hybrid molecules of lipids and 💡apoproteins

A

Lipoproteins

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11
Q

General Properties of Lipids

A
  1. Insoluble in water but soluble in one or more solvents of low polarity such as chloroform, acetone, alcohol and benzene
  2. Esters of fatty acid or capable of forming such esters.
  3. Utilizable by the living organism.
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12
Q

General Properties of Fatty Acids

A
  1. Monocarboxylic acids with hydrocarbon residues that are acyclic and unbranched.
  2. Number of carbon atoms is in most cases even.
  3. May or may not contain double bonds
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13
Q

No double bonds

Abundant in animal fats

A

Saturated fatty acids

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14
Q

They have double bonds

Abundant in plant and fish oils

A

Unsaturated fatty acids

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15
Q

They have one double bond

Ex: Palmitoleic acid (16:1) & Oleic acid (18:1)

A

Monounsaturated fatty acids

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16
Q

They have two or more double bonds.

Ex: omega-3 and omega-6 fatty acids

A

Polyunsaturated fatty acids

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17
Q

They are derived from eicosa-(20 C) polyenoic fatty acids.
Ex: Prostanoids & leukotrienes

A

Eicosanoids

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18
Q

Nutritional Classification of Fatty Acids

A
  1. Nonessential fatty acids

2. Essential fatty acids

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19
Q

These are nutritional fatty acids that 💡can be synthesized in our body.

Ex: saturated fatty acids, palmitoleic acid and oleic acid

A

Nonessential fatty acids

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20
Q

These are nutritional fatty acids that 💡cannot be synthesized in our body.

Ex: omega-3 and omega-6 fatty acids

A

Essential fatty acids

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21
Q

These are the truly essential fatty acids

A

Linoleic acid and alpha-linolenic acid

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22
Q

Examples of Omega-3 fatty acids:

A

a) Alpha-linolenic acid (cis-9,12,15 - octadecatrienoic acid)
b) Timnodonic acid (cis-5,8,11,14,17 – eicosapentaenoic acid)
c) Cervonic acid (cis-4,7,10,13,16,19 – docosahexaenoic acid)

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23
Q

Examples of Omega-6 fatty acids:

A

a) Linoleic acid (cis-9,12- octadecadienoic acid)
b) Gamma-linolenic acid (cis-6,9,12 – octadecatrienoic acid)
c) Arachidonic acid (cis-5,8,11,14 – eicosatetraenoic acid)

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24
Q

Alternating single and double bond.

A

Conjugated Double Bond

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25
Q

Optimal ratio of omega 6 to omega 3 PUFA is between:

A

1:1 and 4:1

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26
Q

-

A

Methylene interrrupted double bond

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27
Q

Fatty acid with 💡more than 12 carbon atoms

A

Long-chain fatty acids

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28
Q

Using the 💡symbol delta plus a superscript number, the reference point is the?

A

Carboxyl group as C-1

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29
Q

Using the 💡symbol omega plus a number beside it reference point is the?

A

Methyl carbon as C-1

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33
Q

It refer to the type of 💡geometric isomerism that occur in unsaturated fatty acids depending on the 💡orientation of the acyl groups around the 💡axes of double bonds.

A

Cis

Trans

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34
Q

An isomerism formed when the 💡acyl groups are on the 💡same side of the bond; produces a 💡kink

A

Cis Isomerism

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35
Q

An isomerism formed when the 💡acyl groups are on the 💡opposite side.

A

Trans Isomerism

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36
Q

It is a 💡by product of hydrogenation or hardening of natural oils in the manufacture of margarine.

Increased risk of CVD and DM

It raises the levels of TAG and LDL

A

Trans Fatty Acid

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37
Q

Gamma linoleic acid (18:3;6,8,12)

A

1st digit is the number of carbon atoms
2nd digit is the number of double bonds.
Succeeding number after the 2nd bond is the location of the double bonds.

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38
Q

Medium chain fatty acid (rich in Philippines)

Lauric Acid

A

Coconut oil

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39
Q

See anki for the table

A

Physical Properties of Fatty Acids

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40
Q

Deleterious effects of trans fats occur at intakes of:

A

2-7 g/day

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41
Q

Examples of 💡soluble soaps:

A

Sodium & potassium soaps (e.g. sodium oleate)

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42
Q

Examples of 💡insoluble soaps:

A

Calcium & magnesium soaps (e.g. calcium palmitate)

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43
Q

It is a reaction between the 💡carboxyl group of the fatty acid and the 💡hydroxyl group of an alcoholic substance forming an 💡ester compound linked by an 💡ester bond.

A

Esterification

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44
Q

It refers to 💡fatty acid residues.

A

Acyl group

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45
Q

Chemical reactions of fatty acids:

A

Saponification
Esterification
Reactions of double bonds
Oxidation of the double bonds

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46
Q

Only 💡unsaturated fatty acids will give these kind of reactions

A

Reactions of double bonds

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47
Q

Soap formation

A

Saponification reaction

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48
Q

It is a reaction with hydrogen forming 💡saturated fatty acids
It is the principal reaction behind manufacturing of solid shortenings, e.g., margarine

A

Hydrogenation reaction

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49
Q

It is a reaction with 💡halogens like iodine forming 💡iodinated saturated fatty acids
The reaction involved in a chemical test – Iodine number

A

Halogenation reaction

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50
Q

Test to determine the 💡degree of unsaturation

Directly proportional

A

Iodine number

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51
Q

💡In vitro oxidation of double bonds that causes formation of short-chain fatty acid aldehyde producing 💡rancid fat.

A

Rancidification

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52
Q

💡In vivo oxidation of fatty acid that forms ROS (free radicals) that causes the following:

  • destroy the integrity of cell membranes
  • cause cancer
  • aging of tissues
  • implicated in degenerative diseases
A

Lipid Peroxidation (auto-oxidation)

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53
Q

These are compounds that 💡inhibit oxidation

A

Antioxidants

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54
Q

It contains 💡three fatty acids are esterified to 💡one glycerol

  • Primary ester bonds – 1st and 3rd carbon atoms
  • Secondary ester bond – 2nd carbon atom (asymmetric/ chiral)
  • Note: Fatty acid in carbon 2 is usually 💡unsaturated

💡Most abundant naturally occurring lipid
💡Most abundant dietary lipid
💡Chief storage form of energy in our body; stored mostly in 💡adipose tissue
¨Adipose tissue under the skin also serve as 💡insulation against low temperatures
¨💡Neutral fat since it does not have any charge
¨Other neutral fats: monoacylglycerol & diacylglycerol

A

Triacylglycerol (Triglyceride)

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55
Q

Salts of fatty acid

Maybe soluble or insoluble to water

A

Soaps

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56
Q

Classification of Triacylglycerol (TAG)

A
  1. According to number of kinds of fatty acids present

2. According to length of hydrocarbon residues of the fatty acids present in TAG

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57
Q

According to number of kinds of fatty acids present

A
  1. Simple TAG

2. Mixed TAG

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58
Q

All three fatty acids are the same e.g., tripalmitin, triolein, triarachidonin

A

SIMPLE TAG

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59
Q

There are 💡two or three different kinds of fatty acids esterified to glycerol

A

MIXED TAG

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60
Q

The mixed TAG are more__ than simple TAG.

A

common

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61
Q

Fatty acid with 💡2 to 4 carbon atoms

A

Short-chain fatty acids

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62
Q

Example of esterification reaction:

A

Triglyceride synthesis

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63
Q

Examples of reaction of double bonds:

A

Hydrogenation reaction

Halogenation reaction

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64
Q

Advantages of TAG as stored fuel:

A
  1. C atoms are more reduced; yields more energy.

2. Hydrophobic unhydrated; does not have to carry extra weight of water.

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65
Q

PHYSICAL Properties of TAG:

Depends on the kind of fatty acids esterified to TAG

A

💡Fats are TAG that are solid at room temp. (Presence of more long chain saturated FA e.g. lard)

💡Oils are TAG that are liquid at room temp. (Presence of more unsaturated FA e.g. cooking oils)

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66
Q
  • 💡Acid (e.g. HCl) or 💡enzyme (lipase) is used as the hydrolyzing agents
  • Products of hydrolysis are 💡free fatty acids & 💡glycerol
  • Fatty acids are insoluble in water
  • Reaction is 💡reversible
A

ORDINARY HYDROLYSIS

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67
Q
  • 💡NaOH or 💡KOH are used as the hydrolyzing agents
  • Products of hydrolysis are 💡Na or 💡K soap and 💡glycerol
  • The soaps are 💡soluble in water
  • Basis of the chemical test – 💡Saponification Number
  • Reaction is 💡irreversible
A

Alkali hydrolysis (saponification reaction)

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68
Q

It determines the 💡degree of unsaturation of a given fat or oil.
💡More double bonds, 💡the higher the iodine number.

A

Iodine number

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69
Q

It determines the 💡average length of the carbon chain or 💡molecular weight of the TAG.
Molecular weight is 💡inversely proportional to the saponification number.

A

Saponification number

70
Q

It measures the 💡volatile fatty acid content of the TAG

💡Short chain TAGs have high RM

A

Reichert Meissl Number

71
Q

Measures the 💡hydroxy fatty acid content of the TAG

Castor oil has high AN because of its high content of 💡ricinoleic acid, a hydroxylated fatty acid.

A

Acetyl number

72
Q

Importance of Phospholipids

A
  1. Most abundant component of cell membranes
  2. Integral component of plasma lipoproteins
  3. Important component of lung surfactant
  4. Solubilizes cholesterol in bile
  5. Involved in blood coagulation
  6. Activator/cofactor of some enzymes
73
Q

Classification of Phospholipids

A

I. Phosphoglyceride or Glycerophosphatide (A. Phosphatidate; B. Plasmalogen)

II. Phosphosphingoside or sphingomyelin

74
Q

Examples of Phosphatidate:

A
1. Lecithin
2 Cephalin
3. Lipositol
4. Cardiolipin
5. Phosphatidyl glycerol
6. Phosphatidyl serine
75
Q
Give the chemical names of the following phosphatidate:
1. Lecithin
2 Cephalin
3. Lipositol
4. Cardiolipin
A
  1. Phosphatidyl choline
    2 Phosphatidyl ethanolamine
  2. Phosphatidyl inositol
  3. Diphosphatidyl glycerol
76
Q

Most of the TAG found in nature are __.

A

Long-chain

77
Q

Medium-chain TAG are easier to (1)__ and (2)__.

A

(1) digest

(2) absorb

78
Q

It is a glycerophosphatidates which is the most abundant 💡membrane phospholipid.

It is 💡insoluble in acetone.

A

Lecithin – Phosphatidyl choline

79
Q

It is the most important component of the 💡lung surfactant which 💡prevents the collapse of the lungs at the end of the expiratory phase of respiration

Deficiency will cause 💡respiratory distress syndrome in newborns

A

Dipalmitoyl phosphatidyl choline

80
Q

It is a glycerophosphatidates which is important component of 💡platelet thromboplastin which is involved in blood coagulation.

A

Cephalin – Phosphatidyl ethanolamine

81
Q

Hydrolysis of Triacylglycerols

A
Ordinary hydrolysis
Alkali hydrolysis (saponification reaction)
82
Q

What is the structural differences between glycerophosphatide and sphingomyelin?

A

The structural backbone for glycerophosphatide is 💡glycerol and the parent compound is 💡phosphatidic acid.

The structural backbone for sphingomyelin is 💡sphingosine and the parent compound is 💡ceramide.

83
Q

Phosphorylation of inositol will transform lipositol into __.

These are are precursors of 💡second messengers of hormones; cell signaling.

A

Phosphoinositides

84
Q

It is the 💡simplest glycerophosphatide.

It is the 💡parent compound & basic structure of all phosphatidates

A

Phosphatidic Acid

85
Q

It is a glycerophosphatidates which is formed by attaching 💡another phosphatidic acid to the glycerol side-chain.

It attaches 💡cytochrome C of the ETC to the inner mitochondrial membrane
It is the only phosphatidate with known 💡immunological property

Decreased in this glycerophosphatidates cause 💡mitochondrial dysfunction in aging, heart failure, hypothyroidism and 💡Barth syndrome (cardioskeletal myopathy)

A

Cardiolipin

86
Q

It is a phosphoglyceride wherein the side-chain in 💡carbon 1 of phosphatidic acid and an 💡 α,β-unsaturated high molecular weight alcohol

  • Forms an 💡OH-OH (ether) linkage with C-1
  • Classified as 💡ether lipid
  • Found in cardiac and skeletal muscles, brain & liver
  • Uses the suffix – 💡dal instead of – dyl
A

Plasmalogen

87
Q

It is a condition where 💡spingomyelin accumulates in the brain, liver & spleen due to deficiency of 💡spingomyelinase.

A

Niemann-Pick disease

88
Q

Cephalin is insoluble with?

A

Ethyl and methyl alcohol

89
Q

Ceramide is attach to sphingosine by what linkage?

A

Amide linkage with fatty acid

90
Q

Side-chain attached to ceramide is __ by a phosphoester bond

A

Phosphoryl choline

91
Q

It is a glycerophosphatidates which found in the 💡inner leaflet of the lipid bilayer

Inversion of its location in the membrane is an
💡early sign of apoptosis

Also involved in 💡blood coagulation

A

Phosphatidyl serine – cephalin-like phosphatidate

92
Q

Fatty acid with 💡6 to 12 carbon atoms.

A

Medium-chain fatty acids

93
Q

According to length of hydrocarbon residues of the fatty acids present in TAG:

A
  1. Short-chain TAG e.g. tributyrin
  2. Medium-chain TAG e.g. 1,2-dilauryl-3-caprylin
  3. Long-chain TAG e.g. 1,3-dipalmitoyl-2-linolein
94
Q

It is a glycerophosphatidates where 💡glycerol is the side-chain and is a precursor of 💡cardiolipin

A

Phosphatidyl glycerol

95
Q

They are lipids with an attached 💡carbohydrate or carbohydrate chain.
They are widely distributed in every tissue of the body, particularly in 💡nervous tissue such as brain.

A

Glycolipids

96
Q

Glycolipids are found in the __ of the cell membrane as part of the 💡glycocalyx of the cell surface

A

Outer leaflet

97
Q

O Blood Type

Immunodominant sugar?

A

Glucose

98
Q

A Blood Type

A

N-acetyl galactosamine

99
Q

B Blood Type

A

Galactose

100
Q

💡Simplest among glycolipids because they contain 💡only one sugar - glucose or galactose

A

CEREBROSIDES

101
Q

It is abundant in brain

A

Sphingomyelin

102
Q

All naturally occurring unsaturated fatty acids are __.

A

Long chain

103
Q

It is the predominant simple glycosphingolipid of 💡extraneural tissues, also occurring in the brain in small amounts.

A

GLUCOCEREBROSIDES

104
Q

They are 💡complex glycosphingolipids derived from 💡glucosylceramide that contain in addition one or more molecules of a 💡sialic acid.

A

Gangliosides

105
Q

Krabbe disease enzyme deficiency: ?

○ Abundant galactocerebroside in the 💡white matter of the brain

○ Destroys the protective coating 💡(myelin) of nerve cells in the brain and throughout the nervous system

A

Galactocerebrosidase (GALC)

106
Q

Also known as ‘Glycolipids’.

A

GLYCOSPHINGOLIPIDS

107
Q

Metachromatic leukodystrophy disease enzyme deficiency: ?

○ Accumulation of galactosylceramide-3-O-sulfate (sulfatide) in the 💡central and peripheral nervous systems.

A

Arylsulfatase A (ARSA)

108
Q

Gaucher disease enzyme deficiency: ?

○ Glucocerebrosides accumulate in the liver and spleen of patients

A

Glucocerebrosidase

109
Q

CEREBROSIDES Examples:

A
  1. GLUCOCEREBROSIDES

2. GALACTOCEREBROSIDES

110
Q

GLUCOCEREBROSIDES

A

GLUCOSYLCERAMIDE

111
Q

Fabry disease enzyme deficiency: ?

○ Accumulation of 💡ceramide trihexoside (globotriaosylceramide)

A

Alpha-galactosidase A (a-Gal A)

112
Q

● 💡Major sulfolipid of the brain
● Abundant in the 💡white matter
● 3rd carbon atom of Galactose will be sulfated → 💡Galactose 3-SO4

A

SULFATIDE

113
Q

GALACTOCEREBROSIDES

A

Galactosylceramide

114
Q

Galactose attached to the ceramide

A

GALACTOCEREBROSIDES

115
Q

💡Most complex among glycolipids

Ceramide + Sialic Acid or N-acetylneuraminic acid (NANA) + N-acetylglucosamine or N-acetylgalactosamine + D-glucose or D-galactose

A

GANGLIOSIDES

116
Q

Oligosaccharide + Ceramide =

A

Globoside

117
Q

When two or more sugars are attached to ceramide, __ is directly attached to ceramide and the succeeding sugar is attached to preceding sugar

A

Only one sugar

118
Q

It is a receptor for 💡cholera toxin in the intestines

A

GM1

119
Q

Accumulation of GM1

A

Generalized gangliosidosis

120
Q

GLOBOSIDE Examples:

A

Lactosylceramide

Ceramide trihexoside

121
Q

GANGLIOSIDES is found principally in the?

A

Brain (concentrated in the ganglion cells)

122
Q

Principal gangliosides:

A

GM1, GD1, & GT1

123
Q

It is the 💡most common sterol in the membranes of animal cells

A

Cholesterol

124
Q

Contain 💡8 to 10 carbons in the side-chain 💡(C-27, C-28 and C-29 steroids)

A

STEROLS

125
Q

Have 💡5 carbons in the side-chain that terminates in a carboxyl group 💡(C-24 steroids)

A

BILE ACIDS

126
Q

Contain 💡2 carbons in the side-chain 💡(C-21)

A

PROGESTERONE AND ADRENOCORTICAL

127
Q

It is a 💡precursor for all steroid hormones

A

Progesterone

128
Q

Tay Sach’s disease enzyme deficiency: ?

○ Accumulation of GM2

A

Hexosaminidase A

129
Q

No side-chain on 💡C-17

A

SEX HORMONES

130
Q

Side-chain on 💡C-19

A

Testosterone

131
Q

Side-chain on 💡C-18

A

Estradiol

132
Q

Hydroxyl group (-OH) is 💡unesterified

A

Free cholesterol

133
Q

Hydroxyl group is 💡esterified to unsaturated fatty acid

💡Storage form of cholesterol in tissue

💡Precursor of a large number of equally important steroids

A

Cholesterol ester

134
Q

● Parent compound of all steroids

● Parent ring-structure

A

CYCLOPENTANOPERHYDROPHENANTHRENE RING

135
Q

Dominant cholesterol in 💡blood

A

Cholesterol ester

136
Q

Dominant cholesterol in 💡bile

A

Free cholesterol

137
Q

Primary Bile Acids Examples:

A

Cholic acid

Chenodeoxycholic Acid

138
Q

How do steroids differ from one another?

A

Dependent on the number of carbon atoms in the R group attached to the Carbon 17

○ Convenient way of classifying steroids

139
Q

Vitamin D3

A

Cholecalciferol (hormone form of calcitriol)

140
Q

An enzyme that will cleave the ester bond, releasing the free cholesterol and fatty acid.

A

Cholesterol esterase

141
Q

It is the 💡first and principal regulatory step in the biosynthesis of bile acids

A

7α-hydroxylation of cholesterol

142
Q

It is a 💡microsomal cytochrome P450 enzyme designated CYP7A1 that 💡catalyzed 7α-hydroxylation of cholesterol

A

Cholesterol 7-hydroxylase

143
Q

Synthesized in the small intestines

A

Primary Bile Acids

144
Q

Intermediate metabolite in biosynthesis of other steroid hormones

Maintain pregnancy during the first trimester

Involved in menstrual cycle

Drug for threatened abortion

Component of oral contraceptives

A

PROGESTERONE

145
Q

Secondary Bile Acids Examples:

A

Deoxycholic acid

Lithocholic acid

146
Q

Regulate intermediary metabolism

Immunosuppressive and anti-inflammatory action

Play an important role in stress response

A

CORTISOL

147
Q

Synthesized in the liver

A

Secondary Bile Acids

148
Q

FUNCTIONS OF BILE ACIDS

A
  1. Aid fat digestion and absorption
  2. Facilitate absorption of fat-soluble vitamins (A,D,E,K)
  3. Help in solubilization of cholesterol in bile
149
Q

It is formed from testosterone through action of the enzyme 💡5`-reductase.

A

Dihydrotestosterone

150
Q

Carrier of 💡exogenous (dietary) triacylglycerol in the blood

Synthesized in the 💡small intestine

A

CHYLOMICRON

151
Q

Regulates water and sodium metabolism

Involved in blood pressure regulation

Promotes tubular reabsorption of the kidney

A

ALDOSTERONE

152
Q

Normal male sexual development of the embryo

Develops and maintain male secondary sexual characteristics starting from puberty

Important for male fertility

A

TESTOSTERONE

153
Q

● Carries 💡endogenous cholesterol in the blood
● Carrier of 💡“bad cholesterol”
● Source of cholesterol esters that are deposited in blood vessel walls
● Could lead to 💡atherosclerosis

A

LOW DENSITY LIPOPROTEIN

154
Q

Normal female sexual development of the embryo

Develops of female secondary sexual characteristics

A

ESTRADIOL

155
Q

Carries 💡endogenous cholesterol from 💡extrahepatic tissues to the liver

Carrier of 💡“good cholesterol”

Contain the 💡highest amount of phospholipid

A

HIGH DENSITY LIPOPROTEIN

156
Q

VERY LOW DENSITY LIPOPROTEIN
● Removes triacylglycerol synthesized in the liver
● Prevents the development of fatty liver
● Carries endogenous triglycerides in the blood
● It did not come from the diet and synthesized in the liver

A

Pre-beta lipoprotein

157
Q

Synthesized by 💡cyclization of C-20 polyenoic fatty acid (e.g. arachidonic acid) through the action of 💡cyclooxygenase enzyme

💡Two double bonds are lost in the reaction

A

PROSTAGLANDINS/PROSTANOIDS

158
Q

● Formed in the 💡platelets from ARA and EPA
● 💡Stimulates platelet aggregation
● 💡Vasoconstrictor

A

THROMBOXANE

159
Q

TX from arachidonic acid

A

TXA2

160
Q

● Produced by 💡blood vessel endothelium from ARA and EPA
● 💡Inhibits of platelet aggregation
● 💡Vasodilator
● 💡Relaxing smooth muscle

A

PROSTACYCLIN

161
Q

● Formed by the enzyme 💡5-lipoxygenase
● Characterized by presence of 💡3 to 5 double bonds
● Potent chemical mediators of 💡inflammation

A

LEUKOTRIENES

162
Q

HIGH DENSITY LIPOPROTEIN

A

Alpha lipoprotein

163
Q

TX from arachidonic acid

A

TXA2

164
Q

Lipoxygenase vs COX

A

COX loss of 2 double bonds

LOX no double bonds are lost

165
Q

Autacoids Examples:

A

Histamine and serotonin (5-hydroxytryptamine)

166
Q

TX from eicosapentaenoic acid

A

TXA3