Lipids Flashcards by Mica 🎀

Which of the following is true regarding the physical property of
timnodonic acid?

It is a volatile fatty acid.
b. It is less soluble in fat solvents than long-chain saturated
fatty acids.
c. It has a higher boiling point than arachidic acid.
d. Liquid at room temperature.

d. Liquid at room temperature.

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Which of the following is an omega-7 fatty acid found in plants and
marine sources?

Palmitoleic acid

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Which of these following fatty acids have the highest iodine
number?
a. Timnodonic acid
b. Cervonic acid
c. Alpha-linolenic acid
d. Arachidonic acid

Cervonic acid

:Iodine number depends on the number of double bonds.
Cervonic acid is docosahexaenoic acid. It is the one with the six double
bonds. Timnodonic has five. Alpha-linolenic acid—three; arachidonic
acid—four.

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Which of the following alcohol is found in spermaceti?

Cetyl alcohol

> > Sperma(ceti)

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Elaidic acid is the trans isomer of what fatty acid?

Oleic Acid

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What is the most abundant fatty acid in virgin coconut oil?

Lauric acid

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Which of the following TAG has the highest saponification number?

a. 1,2 dibutyric acid (4-carbon fatty acid)
b. Caproic acid (6-carbon)

1,2 dibutyric acid (4-carbon fatty acid)

Rationale: Molecular weight of the fatty acid is inversely proportional.
In this case, choose TAGs with short chain fatty acids or medium chain
fatty acids will have the highest saponification number.

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What is the predominant TAG found in castor oil?

Triricinoleic acid

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Which of the following is the main source of fat in the
Mediterranean diet?

Olive oil

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Which of the following does not belong to the group?
a. Phosphatidyl choline
b. Phosphatidyl inositol
c. Phosphatidyl ethanolamine
d. Phosphatidyl serine

Phosphatidyl inositol

Rationale: Must analyze the options. All others are nitrogen
containing phosphoglycerides, while phosphatidyl inositol is a sugar
alcohol without nitrogen in its structure

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What second messenger involved in signal transduction can be
obtained when PIP2 (phosphatidylinositol-4,5-bisphosphate) is
cleaved by the second enzyme?

: Phospholipase C

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. This phospholipid is the cause of mitochondrial dysfunction in
Barth’s Syndrome

Diphosphatidyl glycerol
(Common name: cardiolipin)

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Platelet-activating factor is derived from this glycerol phosphatide:
a. Phosphatidyl serine
b. Phosphatidyl ethanolamine
c. Phosphatidyl inositol
d. Phosphatidyl choline

Phosphatidyl choline

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Which of the following sphingolipids does not belong to the group?

Sphingomyelin

Rationale: All other option are glycolipids namely, gangliosides,
sulfatides and globosides. Sphingomyelin, although it is a
sphingolipid, it does not contain sugar, while all the other options
have sugar molecules in them.

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This sphingolipid accumulates in the brain of patients suffering
from metachromatic leukodystrophy?

Galactoserebroside-3-Sulfate
(Common name: Sulfatide)

Rationale: The accumulation of sulfatide is caused by a deficient
enzymatic breakdown of this lipid

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Which of the ff. steroids has no side chain attached to Carbon 17?

Testosterone

Sex Hormones: No side-chain on C17

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side chain attachment of testosterone

c-19

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_______ are carriers of exogenous (dietary)
triacylglycerol in the blood.

Chylomicrons

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Which of the ff. steroid derivatives of cholesterol is involved in
intermediary metabolism of glucose, fatty acids, and the amino acids?

Cortisol

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side chain attachment of estradiol

C-18

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Which of the lipoproteins is involved in the mobilization of
endogenous triglyceride synthesized in the liver?

Pre beta lipoprotein

VERY LOW-DENSITY LIPOPROTEIN (VLDL) - Also called prebeta lipoprotein removes triacylglycerols synthesized in the liver
thereby preventing their accumulation. Prevents the development of
fatty liver by prevention of accumulation of triacylglycerols is
mobilized by VLDL. Carries and serves as a vessel for endogenous
triglycerides in the blood.

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Which of these lipoproteins is involved in the reverse transport of
cholesterol?
a. Chylomicron
b. Very Low-Density Lipoprotein
c. Low Density Lipoprotein
d. High Density Lipoprotein

High Density Lipoprotein

High density lipoprotein or alpha lipoprotein carries
cholesterol to the liver for disposal/excretion as free cholesterol in
bile, which is involved in the reverse transport of cholesterol (good
cholesterol).

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_______ or _______ removes triacylglycerols synthesized in the liver.

Very Low-Density Lipoprotein or pre-beta
lipoprotein

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_______ or ________ carries endogenous
cholesterol in the blood (bad cholesterol).

Low density lipoprotein or beta lipoprotein

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This eicosanoid is an endogenous anti-inflammatory molecule that plays a vital role in reducing excessive tissue injury and inflammation.

Lipoxin

This eicosanoid act as a local hormone (i.e., autocoids) that can either be paracrine or autocrine.

Prostaglandins

This eicosanoid stimulates platelet aggregation, and it is a vasoconstrictor.

Thromboxane

This eicosanoid inhibits platelet aggregation, and it is a vasodilator.

Prostacyclin

These eicosanoids are potent chemical mediators of inflammation

Leukotrienes

Which of the following lipids will give the highest amount of energy upon oxidation? a. 1-stearoyl-2-oleyl-phosphatidyl choline b. 1-palmitoyl-2-arachidonic-3-laurin c. Cholesterol-3-gamma-linolein d. Ceramide oligosaccharide

a. 1-stearoyl-2-oleyl-phosphatidyl choline (It is lecithin with 2 fatty acids.) ANSWER b. 1-palmitoyl-2-arachidonic-3-laurin (It is a triglyceride with 2 long chains and 1 mediumchain lauric acid.) c. Cholesterol-3-gamma-linolein (It is a cholesterol ester.) d. Ceramide oligosaccharide (It is ceramide with only 1 fatty acid.)

Which one is NOT an ester of fatty acid with a high molecular weight monohydric alcohol? a. Cerumen b. Carnuba wax c. Lanolin Beeswax

Cerumen (Also known as the earwax; not a true wax.) True wax is an ester of fatty acid with a high molecular weight monohydric alcohol.

What is present in sphingomyelin that is not found in glycosphingolipid? a. Sphingosine b. Ceramide c. Fatty Acid d. Phosphate

Phosphate (Sugars are found in glycosphingolipids.)

What is present in ganglioside that is absent in globoside? (Globoside - ceramide oligosaccharides) a. Glucose or galactose b. Sphingosine c. Sialic acid d. Amino sugar

c. Sialic acid (or N-acetylneuraminic acid)

. Which of these fatty acids is truly essential? a. Alpha-linoleic acid b. Gamma-linoleic acid c. Cervonic acid d. Docosahexaenoic acid

Alpha-linoleic acid All other choices are not truly essential.

All of the following are derived lipids, EXCEPT: a. TXA / Thromboxane b. GLA / Gamma-linolenic acid c. PGE / Prostaglandin E d. LTB / Leukotriene B

b. GLA Gamma-linolenic acid - which is an omega 6 fatty acid; it is not a derived lipids compared to others (although some fatty acids are derived lipids, if the given like lipoxine & prostacyclin)

Virgin coconut oil is very rich in this medium-chain fatty acid. a. Caproic acid b. Capric acid c. Caprylic acid d. Lauric acid

d. Lauric acid All the choices are medium-chain fatty acids but the most abundant, almost 90% is Lauric acid.

Which fatty acid when present in TAGs will give the latter a high Acetyl Number? a. Ricinoleic Acid b. Eicosapentaenoic acid c. Palmitoleic acid d. Stearic acid

Ricinoleic Acid (an only fatty acid with a branching point of hydroxyl group) Acetyl number - determines the presence of hydroxylated fatty acids

Which of the following about the physical properties of arachidic acid is correct? a. Solubility in water similar to butyric acid b. Evaporates when left on the air c. Solid at room temperature d. Low boiling point

c. Solid at room temperature a. Solubility in water similar to butyric acid (butyric acid is short-chain with limited solubility) b. Evaporates when left on the air (arachidic acid is non-volatile) c. Solid at room temperature d. Low boiling point Arachidic acid is a long-chain saturated fatty acid. Arachidonic acid is a long-chain unsaturated fatty acid.

Which of these unsaturated fatty acids is a trans isomer? a. Arachidonic acid b. Elaidic acid c. Timnodonic acid d. Oleic acid

b. Elaidic acid (trans isomer of oleic acid)

The Mediterranean diet is rich in this kind of oil? a. Coconut oil b. Canola oil c. Olive oil d. Corn oil

Olive oil (contains oleic acid, a monounsaturated fatty acid)

The action of phospholipase C on this membrane lipid release second messengers of hormones. a. Phophatidyl inositol 4,5-bisphosphate b. Ceramide phosphoryl choline c. 1-palmitoyl-2cervonyl-phosphatidyl serine d. Galactocerebroside 3-sulfate

a. Phophatidyl inositol 4,5-bisphosphate (PIP2, only substrate for phospholipase C in the membrane; end products 1,2 DAG and IP3)

The phospholipid is deficient in the lung surfactant in newborns with acute respiratory distress syndrome. a. Sphingomyelin b. Diphosphatidyl glycerol c. Phosphatidal ethanolamine d. Dipalmitoyllecithin

d. Dipalmitoyllecithin (Dipalmitoyl phosphatidyl choline)

Inversion of the location of this lipid in the cell membrane from the inner leaflet to the outer leaflet is an early sign of programmed cell death. a. Cardiolipin b. Phosphatidyl serine c. Lipositol d. Phosphatidal choline

Phosphatidyl serine

What is present in a plasmalogen that is absent in a phosphatidate? a. Glycerol b. Fatty acid c. High molecular weight alcohol d. Ester bond

d. Ester bond (should be ether linkage)

What sphingolipid accumulates in the kidney of a patient suffering from Fabry disease? a. Sphingomyelin b. Glucocerebroside c. Sulfatide d. Ceramide trihexoside

d. Ceramide trihexoside

Accumulation of ______ in the brain, liver, and spleen causes Niemann-Pick Disease

sphingomyelin

Accumulation of ______ causes Metachromatic Leukodystrophy

sulfatides

Accumulation of ______ in the liver and spleen causes Gaucher disease

glucocerebrosides

GM2 accumulates in the brain of patients with this lysosomal storage disease? a. Generalized gangliosidosis b. Tay Sach-disease c. Gaucher disease d. Krabbe disease

b. Tay Sach-disease

Accumulation of GM1 causes _______

generalized gangliosidosis;

Accumulation of glucocerebroside causes _______

Gaucher disease;

accumulation of galactocerebroside in brain white matter causes

Krabbe disease.

This is a C-24 steroid which facilitates fat digestion and absorption in the small intestines? a. Ergocalciferol b. Chenodeocycholic acid c. Androstenedione d. Calcitriol

b. Chenodeocycholic acid

Active form of vitamin D

Calcitriol

Vitamin D2 a.k.a _________

Ergocalciferol

Which of these lipoproteins is involved in the reverse transport of cholesterol? a. Chylomicron b. Prebeta lipoprotein c. Beta lipoprotein d. Alpha lipoprotein

Alpha lipoprotein (High Density Lipoprotein)

____________ transports dietary cholesterol, other lipids, and fat soluble vitamins obtained from food;

Chylomicron

__________prevents fatty liver;

Prebeta lipoprotein (Very Low Density Lipoprotein)

_________ carries endogenous cholesterol in the blood;

Beta lipoprotein (Low Density Lipoprotein)

________ carries “good cholesterol”.

Alpha lipoprotein (High Density Lipoprotein)

_________stimulated platelet aggregation and is a vasoconstrictor (exact opposite to PGI3)

TXA3 (Thromboxane A3)

This eicosanoid inhibits platelet aggregation and is a vasodilator. a. TXA3 b. PGI3 c. LTA3 d. LX3

b. PGI3 (Prostacyclin)

_________ are chemical mediators of inflammation;

LTA3 (Leukotriene A3)

__________ is a endogenous anti-inflammatory molecule that reduces excess tissue injury and chronic inflammation.

LX3 (Lipoxene A3)

A lipid is the fraction of any biological material that is

Insoluble in water Soluble in one or more solvents of low polaritY

Lipids are heterogenous group of compounds that contain:

fatty acids, fats and oils waxes steroids phospholipids sphingolipids

fat = ___ kcal

9 kcal

carbs = ___ kcal

4 kcal

protein= ___ kcal

4 kcal

most abundant membrane lipids

phospholipids

alcohol= ___ kcal

7 kcal

most common membrane lipids

Phospholipids: most abundant Free cholesterol Glycosphingolipids

sugar-containing sphingolipid

Glycosphingolipids

Esters of fatty acids with various alcohols

simple lipids

hydroxyl group (–OH) in substance

alcohols

carboxyl group (–COOH)

fatty acid/ FA

forms between –OH and –COOH

ester bond

two structural alcohol backbone in simple and compound lipids.

glycerol sphingosine

ester of three FA and one glycerol.

TAG/ triacylglycerol TRIGLYCEROL

this is NOT important in mammalian tissues

waxes

Mostly consist of 12-32 carbon atoms

waxes

esters of FA with higher molecular weight monohydric alcohols

waxes

Esters of fatty acids and long-chain alcohols

waxes

cera alba

beeswax

major component of beeswax

myricyl palmitate

Fat base and thickener for ointments and creams

beeswax

Depilating wax

beeswax

anti-inflammatory and healing properties

beeswax

Extracted by centrifuging sheep wool to separate oil from chemicals and debris

lanolin

Protects sheep wool and skin from environment.

lanolin

- Vegetable wax from the fronds of the carnauba palm.

caranuba wax

common component of furniture, leather, car and shoe polishes

caranuba wax

cosmetics, polish for candies and medicinal pills, thickener for solvent and oils, hardener for printing inks

caranuba wax

Was used chiefly in ointments, cosmetic creams, fine wax candles, pomades, and textile finishing; later used for industrial lubricants

spermaceti

can attach side chains or functional groups to the hydroxyl groups

glycerol

Trihydric alcohol (three hydroxyl groups attached to three different carbon atoms)

glycerol

very long molecule

sphingosine

synthesize inside our body from a hydroxyamino acid (serine)

sphingosine

first 3 carbon atoms of sphingosine come from this compound

serine

16 C atoms (long chain saturated fatty acid) where serine was derived from

palmitic acid

serine and palmitic acid: can attach fatty acid to the _____________

nitrogen atom

serine and palmitic acid: can attach hydroxyl sugar or phosphorylated side chain to the _____________

hydroxyl group

esters of fatty acids with various alcohol groups+ functional groups

complex (compound) lipids

there is a phosphate group or a phosphoric acid residue

phospholipids

contain carbohydrates (sugars - glycosphingolipids)

glycolipids

hybrid molecules of lipids and apoproteins

lipoproteins

found on the surface of lipoproteins

apoproteins

examples of eicosanoids

prostacyclin prostaglandins thromboxane lipoxins ecotrin

examples of steroids

cholesterol hormones bile acids

lipid soluble vitamins

ADEK

most important component of lipids in general

fatty acids

Insoluble in water but soluble in one or more solvents of _________ such as ___, _____, _____, and ____. Different phospholipids have different solubility in different solvents

low polarity chloroform, acetone, alcohol, and benzene

class of cortisol

pre-cursor/ derived lipids

class of triacylglycerol

simple lipids

class of glycerophosphatide

compound lipids

fatty acids that are not truly essential

DHA and EPA (eicosapentaenoic acid)

other building blocks of compound lipids

sphingosine and glycerol alcohol

food supplement that enhances nutrition

DHA (docosahexaenoic acid) and timnodonic acid

DHA (22:6) and EPA will be truly essential in the absence of _________

Alpha-linolenic acid (ALA)

it contains only one carboxyl group (monocarboxylic)

palmitic acid

No matter how long the hydrocarbon residue is, the last (leftmost) carbon group contains a _____________________ which is referred to as the __________

methyl group (CH3) omega carbon atom

number of carbon atoms: Arachidonic acid

C-20

________ can also serve as a point of reference when locating double bonds if there are more than one.

methyl group (omega carbon atom)

number of carbon atoms: Stearic acid

C-18)

number of carbon atoms: Tuberculostearic acid

C-19

No double bonds

Saturated fatty acids

Have double bonds (one or more)

unsaturated FA

abundant in animal fats

saturated FA

may be envisaged as based on acetic acid (CH3 – COOH) as the first member of the series in which CH2– is progressively added between the terminal CH3– and –COOH groups

saturated FA

Two most abundant saturated fatty acids in nature

palmitic acid (c-16) stearic acid (c-18)

major end product of carbohydrate fermentation by rumen organisms

acetic (C-2)

in certain fats in small amounts (esp. butter). an end product of carb. fermentation by rumen organisms

butyric (C-4)

valeric (no. of C atoms)

spermaceti,, cinnamon, palm kernel, coconut oils, laurels, butter

lauric (C-12)

caproic (no. of C atoms)

nutmeg, palm kernel, coconut oils, myrtles, butter

myristic (C-14)

examples of PUFA

Omega-3 and Omega-6 fatty acids

common in all animal and plant fats

palmitic (C-16)

stearic (no. of C atoms)

C-18

once you have this you can already synthesize Gamma-linolenic acid (GHA)

linoleic acid

abundant in plants and fish oils

unsaturated FA

Can be synthesized from palmitic acid (have the same number of carbon atoms)

palmitoleic acid (16:1)

Can be synthesized from stearic acid (have the same number of carbon atoms)

oleic acid (18:1)

palmitic acid and stearic acid can be synthesized through the saturation reaction by enzyme ________

saturase

MUFA : Can be synthesized inside the body

oleic acid

Most common precursor of eicosanoids

Arachidonic acid

eicosatetraenoic acid

arachidonic acid

formed via lipoxygenase pathway

leukotrienes and lipoxins

Third group of eicosanoid derivatives

leukotrienes and lipoxins

Characterized by the presence of three or four conjugated double bonds, respectively

leukotrienes and lipoxins

__________ cause bronchoconstriction as well as being potent proinflammatory agents, and play a part in asthma.

Non-essential Fatty acids: examples

Saturated fatty acids, palmitoleic acid, and oleic acid

Our body cannot introduce new double bonds beyond carbon atom ______

number 12

Essential fatty acids

Omega-3 and omega-6 fatty acids

alpha-linolenic acid or

(Omega-3)

Linoleic acid or

omega-6

cis-5,8,11,14,17-eicosapentaenoic acid

Timnodonic acid

cis-9,12,15-octadecatrienoic acid

Alpha-linolenic acid

omega 6: truly essential

linoleic acid

Can be synthesized inside the body as long as you have alpha-linoleic acid

timnodonic acid

Timnodonic acid-more commonly known as __________-

EPA eicosapentaenoic acid

20 carbon atoms with 5 double bonds

timnodonic acid

Usually found as a supplement in milk powder formula for babies.

timnodonic acid

cis-4,7,10,13,16,19-docosahexaenoic acid

Cervonic acid

More commonly known as DHA

Cervonic acid

examples of omega-3 FA

alpha-linoleic acid timnodonic acid cervonic acid

If you have EPA, you can synthesize ____

DHA

omega 3: truly essential

alpha-linoleic acid

cis-9,12 octadecadienoic acid

Linoleic acid

(cis-5,8,11,14-eicosatetraenoic acid

Arachidonic acid

cis-6,9,12-octadecatrienoic acid

Gamma-linolenic acid

Once you have GLA you can already synthesize _________-

Arachidonic acid

The three double bonds are methylene interrupted double bonds.

Arachidonic acid

Anti-inflammatory effects

omega-3

pro-inflammatory

omega-6

Diet rich in ___________ are beneficial for cardiovascular disease, cancer, rheumatoid arthritis & Alzheimer disease

ω3 fatty acids

_______ help decrease triglycerides, reduce blood clotting, and lower the risk of stroke and heart failure.

Omega-3 fatty acids

dietary ratio of ω6 to ω3 PUFA is between _______--

1:1 and 4:1

Reference point is the carboxyl carbon atom as C-1

Using the symbol delta (Δ) plus a superscript number

THREE CONVENTIONAL WAYS OF DESIGNATING THE LOCATION OF DOUBLE BONDS

Using the symbol delta (Δ) plus a superscript number Using the symbol omega (ω) plus a number beside it. Using a series of numbers enclosed in a parenthesis.

It is an alternating single bond and a double bond

conjugated type of double bond

It is a system of naming, designating an unsaturated fatty acid.

Using the symbol omega (ω) plus a number beside it.

If oleic acid is an omega 9 fatty acid what about palmitoleic acid?

omega 7 monounsaturated fatty acid that is found in plants.

__________ are easy to digest and easily absorbed by the small intestine

medium chain triglycerides

example of short chain FA

butyric acid (C-4)

example of long chain FA

caproic acid (C-6), caprylic acid (C-8), capric acid (C-10) & lauric acid (C-12)

All naturally occurring unsaturated fatty acids are _________

long chain

in nearly all fats

Palmitoleic

Hydrogenated and ruminant fats

elaidic

cis-9-Octadecenoic

oleic

examples of long chain FA

myristic FA (c-14) arachidic FA (c-20)

Possibly the most common fatty acid in natural fats, particularly high in olive oil

oleic

cis-9-Hexadecenoic

Palmitoleic

all-cis-9,12- Octadecadienoic

linoleic

trans-9-Octadecenoic

elaidic

Corn, peanut, cottonseed, soy bean, and many plant oils

linoleic

some plants, eg, oil of evening primrose, borage oil, minor FA in animals

y-linolenic

all-cis-6,9,12-octadecatrienoic

y-linolenic

fish oils, algal oils, phospholipids in brain

cervonic

frequently found with linoleic acid but particularly in linseed oil

a-linolenic

all-cis-9,12,15- Octadecatrienoic

a-linolenic

found in animal fats; important component of phospholipids in animals

arachidonic

all-cis-5,8,11,14-eicosatetraenoic

arachidonic

monoenoic acids

palmitoleic (omega-7) oleic (omega-9) elaidic (omega-9)

dienoic aids

linoleic (omega-6)

trienoic acids

y-linolenic (omega-6) a0linolenic

tetraenoic acids

arachidonic (omega-6)

pentaenoic acids

timnodonic (omega-3)

hexaenoic acids

cervonic (omega-3)

all-cis-5,8,11,14,17- Eicosapentaenoic

timnodonic

all-cis-4,7,10,13,16,19-Docosahexaenoic

cervonic

important component of fosh oils, eg, cod, liver, mackerel, menhaden, salmon oils

timnodonic

(saturated and unsaturated) _____ and _______ are not affected by number of double bonds

solubility in H20 volatility

acyl group: cis

same side

The ______ is greatly affected by double bond (saturated and unsaturated)

melting point

example: cis

oleic acid

appearance: cis

v shape

appearance: trans

straight

Naturally occurring unsaturated fatty acids exists nearly all in the _______

cis configuration.

example: trans

elaidic acid=

U shape

arachidonic acid

The removal of unsaturated fatty acids and making all the fatty acids saturated, the phospholipids will become very compact and they will form_______

a gel consistency

The cis isomer will produce a ___/_____, and that will form some sort of an arm’s length distance between 2 adjacent phospholipids.

kink, a bend

acyl group: trans

opposite side

by-product of the saturation of fatty acids

trans FA

trans FA raises the levels of ___

triacylglycerol and LDL (bad cholesterol)

it is associated with increased risk of cardiovascular diseases and diabetes

trans FA

trans FA lowers __

HDL - good cholesterol

Increase in the number of ________ in a fatty acid leads to a variety of possible spatial configurations

cis double bonds

Deleterious effects of trans fats occur at intakes of _______ (_________ in a daily caloric intake of 2,000 kcal diet).

2-7 g/day 20 to 60 kcal

ideal daily intake of trans fat

2g/day

soap formation

saponification

salts of fatty acids

soap

a fat with disagreeable odor

rancid fat

soluble soaps

sodium and potassium soaps

Reaction between the carboxyl group of the fatty acid and the hydroxyl group of an alcoholic substance f

esterification

insoluble soaps

magnesium and calcium soaps ex. magnesium palpitate

____ are called neutral fat.

Triglycerides or triacylglycerol

ex. of free radical

superoxide anions

Principal reaction behind manufacturing of solid shortenings, eg., margarine (can be used as sandwich spreads)

hydrogenation

reactions only for unsaturated bonds

hydrogenation halogenation

Due to the formation of short-chain fatty acids aldehyde

rancidification

it determines the degree of unsaturation of a given fat or oil

iodine number

ex. of non free radical

hydrogen peroxide (most abundant)

- Cause cancer - Implicated in degenerative diseases (RA, Alzheimer’s) - Preaging of tissues

oxidation

lipid peroxidation or

auto-oxidation

Generates reactive oxygen species (ROS)

lipid peroxidation

Good money-making part of the pharmaceutical industry

antioxidants

- The lipid radical is stabilized in different resonance structures by delocalization of the free electron

Initiation phase

The lipid radical reacts with molecular oxygen to form a lipid peroxyl radical which propagates the reaction by means of a radical chain reaction.

Propagation phase

The most important fat digesting enzymev

pancreatic amylase

Two lipid radicals react with one another to form a stable bond. Also, from lipid hydroperoxyl radicals, a variety of degradation products like malondialdehyde, 4- hydroxy-2-alkenals or 2- alkenals are formed.

Termination phase

Three fatty acids are esterified to one glycerol

TRIACYLGLYCEROL (TRIGLYCERIDE)

ex. of neutral fat

glyceral

Can easily hydrolyze the primary ester bonds

pancreatic amylase

Fatty acids attached on Carbon 1 (w/ 1 FA)

monoacylglycerol

most abundant type of triacylglycerol

L - triacylglycerol

Another Fatty Acid attached on carbon 2 (w/ 2 FA)

diacylglycerol

most abundant source of ATP

oxidative phosphorylation

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

mixed tag

ester linkages: 1st and 3rd carbon atoms

primary ester bonds

Fatty acid in ________ is usually unsaturated

carbon 2

ester linkages: 2nd carbon atom

secondary ester bond

Most of the end products in lipid digestion or triglyceride digestion is a _________ wherein the fatty acid is in Carbon 2.

Monoacylglycerol

contains only short chain FA

SHORT-CHAIN TAG

most abundant dietary lipid

triacylglycerol

most abundant naturally occurring lipid

TRIACYLGLYCEROL

mostly stores in adipose tissue

triacylglycerol

MEDIUM CHAIN EXAMPLES

1,2-dilauroyl 1-3-caprylin

abundant in polyunsaturated fats, primarily oleic acid and some alpha-linolenic acid.

soybean oil

ADVANTAGES OF TAG AS STORED METABOLIC FUEL

- carbon atoms are more reduced - hydrophobic, unhydrated

simple tag examples

- tripalmitin (3 palmitic acid) - triolein (3 linoleic acid) - triarachidonin (3 serbonic acid)

classification of TAG: all three FA are the SAME kind

simple tag

_____ TAGs are easier to absorb.

Medium-chain

More common than Simple TAG

mixed tag

ex: 1-palmitoyl-2-linoleoyl-3 butyrin

mixed tag

Most of the TAGs found in nature are __________

long-chain

Most of the time, __________ are used to hydrolyze triglycerides

ENZYMES (lipase)

ex: 1,3-distearoyl-2-olein

mixed tag

CONTAINS 6-12 CARBON ATOMS

MEDIUM-CHAIN TAG

TYPE OF TAG: 1,3-DIPALMITOYL-2-LINOLEIN

LONG-CHAIN

SHORT CHAIN TAG EXAMPLES

TRIBUTYRIN - BUTYRIC ACID CONTAINS FOUR CARBON ATOMS

rich in medium-chain triglyceride (MCTs), primarily lauric acid

coconut oil

composed of mainly long-chain saturated fatty acids, particularly palmitic acid.

palm oil

TAGs that are solid at room temperature

FATS

used for cooking, may also contain small amount of unsaturated fatty acids

Lard

contains a significant amount of polyunsaturated fats, notably linoleic acid.

corn oil

contains long-chain omega-3 fatty acids like eicosapentanoic acid (EPA) and docosahexanoic acid (DHA)

Fish Oil

high in monounsaturated fats

Canola Oil

only happens in the lab

alkali hydrolysis

predominantly comprises monounsaturated fats, mainly oleic acid.

Olive Oil

free FA are _______ in water

insoluble

Cut or cleave the ester bond that connects the fatty acid to the hydroxyl group.

ORDINARY HYDROLYSIS

ordinary hydrolysis: Uses ACID or ENZYME as the hydrolyzing agents

HCL and lipase

ordinary hydrolysis: Once absorbed, it will go into the blood and tissues will take it up for.

metabolism

ordinary hydrolysis: Once free fatty acids are released, it's either combined with ________/_________ in the diet or it is absorbed right away by the intestinal cells.

sodium or calcium

products of ordinary hydrolysis

3 fatty acids and 1 glycerol

reaction is reversible

ordinary hydrolysis

alkali hydrolysis or

saponification reaction

alkali hydrolysis: ________/______are used as hydrolyzing agents which are very corrosive chemicals.

NaOH KOH

Degree of unsaturation of a given fat or oil.

iodine number

iodine number of saturated FA

T OR F IODINE NUMBER IS ↓ PUFA

T OR F ↑ double bonds = ↑ iodine number

products of alkali hydrolysis

sodium/potassium soaps glycerol

example of soaps

sodium palmitate potassium oleate

______ have low molecular weight and high saponification number

short chain fatty acids

T OR F SAPONIFICATION ↑ Molecular weight = ↓ Saponification number

Volatile fatty acid content of the TAG

REICHERT MEISSL NUMBER

Average length of the carbon chain or molecular weight of the TAG.

SAPONIFICATION NUMBER

Volatile fatty acids have ______ carbon atoms (e.g. Butyric Acid)

2-4

Measures the hydroxy fatty acid content of the TAG

ACETYL NUMBER

Castor oil - has a high acetyl number due to high content of _________ used to cleanse the bowel before doing colonoscopy

ricinoleic acid

most abundant phospholipid in lung surfactant; a specific lecithin/phosphatidylcholine

DIPALMITOYLPHOSPHATIDYLCHOLINE

Measures short-chain TAGs

REICHERT MEISSL NUMBER

___________ has a high acetyl number because of its high content of ricinoleic acid, a hydroxylated fatty acid

Castor oil

Fatty acids are ________ and ______

unbranched AND and acyclic

There is an hydroxyl group (-OH) attached to the hydrocarbon residues

ACETYL NUMBER

2 substances that have the ability to solubilize cholesterol in bile -

BILE ACID AND PHOSPHOLIPIDS

Major component of lung surfactant

PHOSPHOLIPIDS

Most abundant component of cell membranes

PHOSPHOLIPIDS

a digestive juice that is produced by the liver and stored in the gallbladder

BILES

reaction is irreversible

alkali hydrolysis

PREFIX FOR PLASMOGEN

PHOSPHATIDAL

PARENT GROUP OF PHOSPHATIDATE

PHOSPHATIDIC ACID

TRIVIAL NAME OF phosphatidyl choline

LECITHIN

TRIVIAL NAME OF phosphatidyl ethanolamine

CEPHALIN

PREFIX FOR PHOSPHATIDATE

PHOSPHATIDLY

MOST ABUNDANT PHOSPHOLIPIDS

PHOSPHOGLYCERIDE/ GLYCEROPHOSPHATIDE

PHOSPHOLIPIDS: substance that promotes blood clotting/coagulation

THROMBOPLASTIN

TRIVIAL NAME OF diphosphatidyl glycerol

CARDIOLIPIN

TRIVIAL NAME OF phosphatidyl inositol

LIPOSITOL

MOST ABUNDANT MEMBRANE PHOSPHOLIPID

LECITHIN

Precursor of cardiolipin

PHOSPHATIDYL GLYCEROL

KINK IS PRODUCED BY ______

cis isomer of the unsaturated double bond of fatty acid.

deficiency will cause respiratory distress syndrome in newborns (such as dyspnea)

dipalmitoyl phosphatidyl choline

insoluble in ethyl and methyl alcohol

CEPHALIN

FUNCTIONAL GROUP OF SPHINGOSINE

SERINE

SIMPLEST GLYCEROPHOSPHATIDE

PHOSPHATIDIC ACID

INSOLUBLE IN ACETONE

LECITHIN

cephalin-like phospatidate

HOSPHATIDYL SERINE

inversion of its location in the membrane is an early sign of apoptosis or program cell death

PHOSPHATIDYL SERINE

important component of platelet thromboplastin

CEPHALIN

hydroxyl groups of inositol will become phosphorylated by the enzyme __

KINASES

3 NITROGEN CONTAINING PHOSPHOLIPIDS3 NITROGEN CONTAINING PHOSPHOLIPIDS

Lecithin * Cephalin * Phosphatidyl serine

found in the inner leaflet of the lipid bilayer facing the cytoplasm >> THE REST FOUND IN OUTER LEAFLET

PHOSPHATIDYL SERINE

Is the most important phosphoinositide found in the cell membrane

Phosphatidyl inositol 4,5-bisphosphate (PIP2)

what makes INOSITOL different from lecithin, cephalin & phosphatidyl serine

IT'S A SUGAR ALCOHOL

___ are precursors of second messengers of hormones;

Phosphoinositides

Only phosphatidate with known immunological property

CARDIOLIPIN - aka diphosphatidyl glycerol

rare X-linked recessive disorder characterized by cardiolipin abnormalities

BARTH SYNDROME

phosphorylation of inositol will transform lipositol into ___

phosphoinositides

involved in blood coagulation

PHOSPHATIDYL SERINE CEPHALIN

a phosphoglyceride wherein the sidechain in carbon 1 of phosphatidic acid is an α,β-high molecular weight alcohol.

PLASMOGEN

he underlying cause of BTHS has been definitively traced to mutations in the ____.

TAZ gene

Phosphoglycerides containing only one fatty acid

LYSOPHOSPHOLIPID

Intermediate in phosphoglyceride metabolism

LYSOPHOSPHOLIPID

___ is the carrier of bad cholesterol indicated in atherosclerosis

LDL

____ is the build-up of fats and cholesterol in the walls of the artery.

atherosclerosis

ound in oxidized Low Density Lipoprotein (LDL) which is implicated in atherosclerosis.

LYSOPHOSPHOLIPID

PLASMOGEN LINKAGE

OH-OH (ether) linkage with C-1

PLASMOGEN CLASSIFICATION

ETHER LIPID

Found in cardiac and skeletal muscles, brain, and liver

PLASMOGEN

It causes a dramatic inflammation of air passage resulting in asthma-like symptoms.

platelet-activating factor

_________ is a potent phospholipid mediator that was first described by its ability to cause platelet aggregation and dilation of blood vessels. Now it is also known as a potent mediator of inflammation, allergic responses, and shock.

PAF platelet-activating factor

membrane lipids that predominate in plant cell

galactolipids sulfolipids

linkage of galactolipids

1,3 DAG (Diacylglycerol) by an Oxygen- glycosidic bond.

linkage of sulfolipids

1,2 DAG (Diacylglycerol) by a glycosidic linkage.

second major group of phospholipids

sphingomyelin

charge: sulfolipids

negative

parent compound of sphingomyelin

ceramide

spingomyelin: structural backbone

sphingosine

sphingosine: linkage

amide linkage with fatty acid

sphingomyelin: Side chain attached to ceramide is esterified to phosphoryl choline by ____ , in order to form sphingomyelin

phosphoester bond

These are human metabolic storage disorders, which are characterized by accumulation of harmful quantities of glycosphingolipids and phosphosphingolipids.

sphingolipidoses

Found in the outer leaflet of the cell membrane as part of the glycocalyx (or extracellular matrix) of the cell surface of animal cells

GLYCOSPHINGOLIPIDS

If you attach ____ to the H antigen, you will be blood type A.

N-acetyl-galactosamine

side chain of sphingomyelin

phosphoryl choline

If you attach ___ to the H antigen, you will be type B.

galactose

* Three building block components of sphingolipids:

1 mol of fa 1 mole of sphingosine 1 polar head group >> phosphoryl choline or sugar

example of sphingolipidoses

niemann pick disease

what is embedded in the red blood cell membrane?

CERAMIDE

GLYCOSPINGOLIPIDS FUNCTIONS

- INTERCELLULAR COMM, AND CONTACT - IN ORGAN AND TISSUE SPPECIFICITY - RECEPTORS FOR BACTERIAL TOXIN - AS ABO BLOOD GROUP SUBSTANCES

simplest glycolipid

cerebroside

Accumulates in the liver and spleen of patients suffering from Gaucher disease

glucocerebroside/glucosylceramide

In the O antigen in your red blood cell, the immunodominant sugar is ___

FUCOSE

Are lysosomal storage diseases with defects in the catabolic pathway for sphingolipids.

sphingolipidoses

Is the biosynthetic pathway defective also in sphingolipidoses?

Abundant in the white matter

SULFATIDE (GALACTOCEREBROSIDE 3-SULFATE)

The most common fatty acid in amide bond with sphingosine is the ________ found in the brain

cerebronic acid (C24)

found outside the nervous system

glucocerebroside/glucosylceramide

cerebroside contains ___ sugar

bond: sphingosine-glucose

glycosidic

bond: sphingosine-fatty acid

amide bond

abundant in the kidney; accumulates in patients with Fabry disease

ceramide trihexoside

accumulates in generalized gangliosides

GM1

composition of ganglioside

ceramide sialic acid or NANA (N-acetylneuraminic acid) amino sugars hexoses

parent ring of steroids

cyclopentanoperhydrophenanthrene

Accumulates in the white matter of the brain of patients suffering from Krabbe disease

galactocerebroside

Is cerebronic acid saturated or unsaturated?

Cerebronic acid is a long-chain saturated fatty acid with 24 carbon atoms

Major sulfolipid of the brain

SULFATIDE (GALACTOCEREBROSIDE 3-SULFATE)

steroids: 2 ___ are located at the angles or diffused rings.

ambular methyl groups

galactose, glucose, galactose

trihexoside

Ceramide is attached to two to ten sugar units

GLOBOSIDE (CERAMIDE OLIGOSACCHARIDES)

component of erythrocyte membrane

lactosylceramide

accumulates in Tay Sach’s disease

GM2

How do you classify steroid?

According to the number of Carbon atoms in the R group attached to the Carbon 17 of ring B

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

bile acids

Principal gangliosides

GM1 (mono), GD1 (di), GT1 (tri)

GANGLIOSIDES NAMING Subscript capital letters – means the number of___

sialic acid.

steroids with 27 to 29 carbon atoms are

sterols

OH group is unesterified

free cholesterol

contain 2 carbons in the side-chain (C-21).

Progesterone and Adrenocortical hormones:

breaks down ester bonds in cholesterol

cholesterol esterase

Contain 8 to 10 carbons in the side chain

steroids

vitamin D3 AKA

cholecalciferol

No side-chain on C17

sex hormones

functions of cholesterol

component of cell membrane precursors of Vit D3, bile acids and ALL steroid hormones

Biologically active form of cholesterol

free cholesterol

Hydroxyl group (OH) is esterified to unsaturated fatty acid.

cholesterol ester

_____ is very important in regulating the fluidity of cell membrane because it interspersed with the phospholipids of the bilayer, creating separating among the lipids

cholesterol

Prevents the development of fatty liver by prevention of accumulation of triacyglycerols is mobilized by VLDL.

VLDL/ PRE BETA

basis for quantitative determination of cholesterol in the blood

Lieberman-Burchard Reaction

represent the largest family of natural products in the living world

polyprenoids

biogenic compounds that derive from the assemblage and modification of five-carbon isoprene units.

polyprenoids

widely present in membranes and are involved in the N-glycosylation of proteins.

dolichol

lipoprotein shape

spherical

polar or non polar: free cholesterol

polar

composed of a 1,4-benzoquinone moiety linked to a polyprenyl chain

ubiquinones

There apoproteins are just sitting on top of one another which is why they are transferable from one lipoproteine to the other (Not tightly bound)

peripheral apoprotein ex: apoprotein C

play a critical role in the electron transport within the inner membrane of mitochondria

ubiquinones

These are deeply embedded, so they are not easily transferrable. Additional examples are, B 48 and B 100.

peripheral apoproteins

location of free alcohol in lipoprotein

outer layer

Removes triacylglycerols synthesized in the liver thereby preventing their accumulation.

VLDL PRE BETA LIPOPROTEIN

VLDL OR

PRE BETA LIPOPROTEIN

lipoproteins: Lipid core has two most hydrophobic lipids present in our body ___ , ____

triacylglycerol cholesteryl ester

On the surface, it has protein molecules called apolipoproteins (apoproteins)

lipoproteins

Carrier of “bad cholesterol”

LDL/ BETA

HDL: has two layers of phospholipids

lipoproteins

Carrier of exogenous (dietary) triacylglycerol in the blood.

chylomicrons

can act as an acid or base

Amphoteric

Transports dietary cholesterol, other lipids and fat soluble vitamins obtained from foods

chylomicrons

Outer layer: at least one layer phospholipid layer

lipoprotein

polar and non polar groups in the same structure

Amphipathic

Formed principally in the liver.

LDL/BETA

BETA LIPOPROTEIN AKA

LDL

source of cholesteryl ester that becomes deposited in the atherosclerosis plaques.

LDL CHOLESTEROL

AKA ALPHA LIPOPROTEIN

HDL

Carries and serves as a vessel for endogenous triglycerides in the blood.

VLDL/ PRE BETA

Carrier of “good cholesterol”

HDL / ALPHA

Carries endogenous cholesterol in the blood

LDL/ BETA

Carries endogenous cholesterols synthesized in the extrahepatic tissues (e.g., adrenal glands, gonads, testis) and bring them to the liver for disposal or excretion.

HDL/ ALPHA

Contain the highest amount of phospholipids.

HDL / ALPHA

SUBCATEGORIES OF EICOSANOIDS

PROSTANOIDS LEUKOTRIENES LIPOXINS

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

PROSTAGLANDINS

prostaglandins is Synthesized by cyclization of C-20 polyenoic fatty acid (e.g., arachidonic acid) and eicosapentaenoic acid (EPA) through the action____

cyclooxygenase enzyme.

EXAMPLES OF PROSTANOIDS

PROSTAGLANDINS TRHROMBOXANE PROSTACYCLIN

Act as a local hormone (i.e., autocoids) that can either be paracrine or autocrine

prostaglandins

Have important physiologic and pharmacologic roles in the body

prostaglandins

a potent vasodilator and specifically maintains patency of the ductus arteriosus in the fetus and newborn

PGE1

has a KETO group in position 9

PGE

______ are colloidal suspensions that are formed when a critical concentration of these lipids is present in an aqueous medium

MICELLES

has a HYDROXYL group in this position (C9)

PGF

VASOCONSTRICTOR

THROMBOXANES

Formed in the platelets ARA and EPA

THROMBOXANES

The enzyme ________ converts ARA and EPA to TXA2 and TXA3, respectively.

cyclooxygenase

STIMULATES PLATELET AGGREGATION

THROMBOXANES

Produced by blood vessel endothelium from ARA and EPA

PROSTACYCLIN

Formed in leukocytes, platelets, macrophages, and other inflammatory cells

LEUKOTRIENES

derived from arachidonic acid (ARA)

TXA2 PGI2

Endogenous anti-inflammatory molecule that plays a vital role in reducing excessive tissue injury and chronic inflammation

LIPOXINS

derived from eicosapentanoic acid (EPA)

TXA3 PGI3

Characterized by the presence of 3 to 5 double bonds

LEUKOTIENES

Formed by the enzyme 5-lipooxyegenase

LEUKOTRIENES

__ can also encase hydrophobic or amphiphilic drugs in the center to release them at an appropriate location.

MICELLES

acronym for lipoxygenase interaction product, a bioactive autacoid metabolite of arachidonic acid made by various cell types

LIPOXINS

It helps absorb monoglycerides (MG) and fatty acids from lipid digestion.

MICELLES

Potent chemical mediators of inflammation

LEUKOTRIENES

When paired with tissue-specific antibodies, liposomes can transport medications to specific tissues in the blood, such as in cancer treatment.

LIPOSOMES

_____ are lipid bilayer spheres surrounding a portion of the aqueous media.

LIPOSOMES

also used for gene transfer into vascular cells and as carriers for topical and transdermal drugs and cosmetic delivery

LIPOSOMES

have a limited ability to encapsulate oils compared to emulsions

LIPOSOMES

. They may be made by sonicating amphipathic lipids in water

LIPOSOMES

are larger particles often formed from nonpolar lipids in an aqueous media

EMULSIONS

large lipid globules are reduced into smaller lipid globules

EMULSIFICATION

What do you use for oxidation?

MOLECULAR OXYGEN, OZONE IN LAB

EXAMPLE OF MONOHYDRIC ALCOHOL

MYRICYL ALCOHOL

DIET RICH IN _____ ARE BENEFICIAL FOR CARDIOVASCULAR DISEASE, CANCER, RHEUMATOID ARTHRITIS AND ALZHIEMER DISEASE

omega-3 FA

___ are used to control and reduce lipid peroxidation, both by humans in their activities and in nature

antioxidants

reduce the rate of chain initiation in lipid peroxidation

preventive antioxidants

interfere with chain propagation in lipid peroxidation

chain-breaking antioxidant

Peroxidation is also catalyzed in vivo by heme compounds and by ____ found in platelets and leukocytes

lipoxygenases

other products of auto-oxidation

oxysterols isoprostanes

A free radical (X*) reacts with a polyunsaturated fatty acid forming the first fatty acid radical (R*1)

INITIATION

The unstable fatty acid radical R*1 reacts with oxygen to produce a peroxyl radical (R1OO*)

PROPAGATION

when two radicals react to form a non-radical product

TERMINATION

_______ is a chain reaction in which free radicals formed in the initiation stage in turn generate more (propagation), and thus it has potentially devastating effects.

LIPID PEROXIDATION

SOURCE OF FREE RADICALS

LIPID PEROXIDATION

molecules that have unpaired valence electrons, making them highly reactive.

FREE RADICALS

ANTIOXIDANTS USED AS FOOD ADDITIVES

-Propyl gallate -butylated hydroxyanisole (BHA) -butylated hydroxytoluene (BHT)

EXAMPLE OF PREVENTIVE ANTIOXIDANT

CATALASE GLUTATHIONE PEROXIDASE