BIOCHEM FATS Flashcards
►________ are heterogenous group of
compounds related more by their
physical properties rather than by their
chemical properties
Lipids
Lipids are:
► Relatively __________ in water and
► Soluble in _____________ solvents such as ether
and chloroform
insoluble, nonpolar
___________________ fatty acids have
beneficial effects in a number of
chronic diseases
long chain omega 3
►_____________________ act as electrical
insulators along myelinated
nerves
Nonpolar lipids
LIPIDS are transported in the blood
combined with proteins as ______________________
Lipoproteins
►esters of fatty acids with glycerol
►oils are fats in the liquid state
►FATS
►esters of fatty acids with higher
molecular weight monohydric
alcohol
►WAXES
►derivatives of C-20 fatty acids
►EICOSANOIDS
What are SIMPLE LIPIDS
Fats, Lipids, Eicosanoids
►esters of fatty acids containing groups in
addition to alcohol one or more fatty acids.
►COMPLEX LIPIDS
►containing in addition to fatty acids and
alcohol, a phosphoric acid residue
►frequently have nitrogen containing bases and
other substituents
►PHOSPHOLIPIDS
►lipids containing fatty acids,
sphingosine and carbohydrates
►GLYCOLIPIDS (GLYCOSHINGOLIPIDS)
►include bile salts, steroids, hormones,
ketone bodies, lipid-soluble vitamins
and polyprenoids
►DERIVED LIPIDS
►aliphatic carboxylic acids
►Occur in the body mainly as esters of
natural fats and oils
►FATTY ACIDS
►unesterified form as ________________,
a transport form in the plasma
free fatty acids
►Fatty acids occurring in natural fats
usually contain ______ number of
carbon atoms
even
►The chain containing no double bond
saturated
►The chain containing one or more
double bonds
unsaturated
►Saturated fatty acids end in __________
–anoic
►unsaturated fatty acids with double
bonds end in ______________
-enoic
►Carbon atoms are numbered from the
___________________ (C1)
►carbon adjacent to carboxyl carbon
(C2, C3,and C4) 🡪 ______, _______, and _______ carbons respectively
►terminal methyl carbon is known as
_______ carbon
carboxyl carbon, alpha, beta and
gamma, omega
►Use _____ for indicating the number and
position of the double bonds
delta
►Additional double bonds are introduced
only between an existing double bond at
the ________________
position
omega 9, omega 6, and omega 3
►Based on the ___________ as the
first member of the series
►_____ is progressively added between
the terminal CH3 & the COOH groups
CH3COOH, CH2
►carbons of saturated fatty acids form a
_________ pattern at low temperature
zigzag
►higher temperature some bonds ________
causing shortening of the chain
rotate
►thinning of _____________________ with increase in
temperature
biomembranes
►contain one double bond
►MONOUNSATURATED ACIDS:
►contain two or more double bonds
►POLYUNSATURATED ACIDS:
►______________________ occurs in
unsaturated fatty acids because of the
double bond
Geometric Isomerism
acyl chains are on the same
side of double bond
►CIS Isomer
acyl chains are on the opposite side of double bond
►TRANS Isomer
►present in certain foods
►byproduct in the saturation of fatty acids
during hydrogenation
►hardening of natural oil (margarine)
►TRANS Isomer
►compounds derived from eicosapolyenoic
acids (20-carbons) Comprise the:
►Prostanoids
►Leukotreines
►Lipoxins
►Consumption of ___________________________
is detrimental to health and is
associated with increased risk of
cardiovascular diseases and diabetes
mellitus
saturated fatty acids
►Synthesized from products of glucose
oxidation
NON-ESSENTIAL FATTY ACIDS
►Must be obtained from the diet
►No human enzyme system can
introduce a double bond beyond the
ninth carbon atom of fatty acid
►ESSENTIAL FATTY ACIDS
►Sources of Essential Fatty Acids
►Linoleic and Linolenic Acids
►Corn Oil, Peanut Oil, Cottonseed Oil
and Soybeans
►Linoleic Acid
►Linseed Oil and Evening Primrose Oil
►Linolenic Acid
►Melting point of even numbered
carbon FA increases with __________________
and decreases the greater the
_____________________
chain length, unsaturation
►Triacylglycerol containing three
saturated fatty acids of 12 carbons or
more is _______ at body temperature
solid
►_____________________ are liquid even in
below zero degree Celsius
polyunsaturated
OMEGA 3 FATTY ACIDS in plant oils,
►Alpha-linolenic (ALA)
OMEGA 3 FATTY ACIDS in fish oils
Ecosapentaenoic acid (EPA)
OMEGA 3 FATTY ACIDS in fish & algal oils
Docosahexanenoic acid (DHA)
►Main storage form of fatty acids
TRIACYLGLYCEROLS
►Considered as local hormones functioning
through G- protein-linked receptors to elicit
their biochemical effects
EICOSANOIDS
►give rise to Group 1 Prostanoids and Group 3 Leukotrienes
►Linoleic Acids
►give rise to Group 2 Prostanoids, Group 4
Leukotrienes and Lipoxins
►Arachidonic Acid
►give rise to Group 3 Prostanoids and Group 5 Leukotrienes
Eicosapentaenoic Acid (EPA)
►Exists in every mammalian tissue acting as
local hormones
►Potent platelet aggregators
PROSTAGLANDINS
►Have the cyclopentane ring interrupted by
an oxygen atom
►Synthesized by leukocytes
►Causes vasoconstriction and platelet
aggregation
THROMBOXANES
►Produced in leukocytes, mastocytoma
cells, platelets and macrophages through
lipoxygenase pathway
►Play a role in asthma, causing
bronchoconstriction
►potent post inflammatory agents
LEUKOTRIENES
►Family of conjugated tetraenes
(four conjugated double bonds)
►Also produced by leukocytes by
lipoxygenase pathway
LIPOXINS (LXs)
►derivatives of Phosphatidic acid
►phosphate esterified with one OH
group of glycerol
►PHOSPHOLIPIDS
►Both _______________________ and
_________________ have two long chain
hydrocarbon tail 🡪 lipid bilayer of cell
membranes
glycerophospholipids, sphingolipids
►Glycerophospholipids containing choline
Phosphatidylcholine (Lecithin)
►most abundant phospholipids of cell
membrane
►important in nervous transmission, as
acetylcholine and as a store of labile
methyl group
Phosphatidylcholine (Lecithin)
►very effective surface-active agent
►major constituent of surfactant
preventing adherence due to surface
tension in lungs alveoli
►absence from premature infants’ lungs 🡪
respiratory distress syndrome
►Dipalmitoyl lecithin
►found in most tissues; cell membranes
►ethanolamine and serine replaces
choline in phosphatidylcholine
Phosphatidylethanolamine (Cephalin)
and Phosphatidylserine
► found only in the mitochondria; essential for
mitochondrial function
Cardiolipin
►important in the metabolism and
interconversion of phospholipids
►Found in oxidized lipoproteins and
implicated in some of their effects in
promoting atherosclerosis
Lysolecithin
►Constitute much as 10–30 % of
phospholipids in brain and heart
Plasmalogens
►found in outer leaflet of cell
membrane lipid bilayer
►abundant in specialized areas
of plasma membrane known
as lipid rafts
Sphingomyelins
►complex glycosphingolipids derived from
glucosylceramide
Gangliosides
►cell-cell recognition and cell communication
►receptors for hormones and bacterial
toxins, such as cholera toxin
Gangliosides
simplest ganglioside found in
tissue
►contain ceramide, one molecule of
glucose, one molecule of galactose and
one molecule of NeuAc
►GM3
more complex; derived from
GM3
►receptor in human intestine for cholera
toxin
►GM1
principal sialic acid found in human tissue
►Neuraminic Acid (NeuAC)
present in the nervous tissue in high
concentration
Gangliosides
best known for
association with atherosclerosis and
heart disease
►Cholesterol
►widely distributed in all cells of the
body, particularly in CNS
►major constituent of plasma
membrane and plasma lipoproteins
►CHOLESTEROL
►C-24 steroid
►Derived from cholesterol by
scission of 3 carbon side chain
►Saturation of delta 5 double bond
of cholesterol
►Hydroxylation of steroid nucleus
►BILE ACIDS
►Formed in liver from cholesterol
►CHOLIC ACID
►CHENODEOXYCHOLIC
ACID
►PRIMARY BILE ACIDS
►With hydroxyl groups at carbons
3, 7 and 12
►CHOLIC ACID
►With OH groups at carbon 3 and 7
►Conjugated with glycine or
taurine forming bile salts
►CHENODEOXYCHOLIC
ACID
► Formed in intestine from primary bile acids through the
action of intestinal bacterial enzymes
►SECONDARY BILE ACIDS
► Synthesized from cholic acid
► Hydroxyl groups at carbons 3 and 12
►DEOXYCHOLIC ACID
► non-absorbable bile acids
► Synthesized from chenodeoxycholic acids
► OH group at carbon 3
► About 400 mg/day is excreted in feces daily
►LITHOCHOLIC ACID
►In humans, formed and secreted by
the:
►Adrenal Cortex, Testis, Ovary,
Placenta
►Cholesterol, common precursor
►STEROID HORMONES
Cortisol is produced by _____________
zona fasciculata
Aldosterone is produced by _____________
zona glomerulosa
►Conversion of progesterone to
aldosterone involves: Hydroxylation of C-11 and & C-21 forming _______________
corticosterone
►Produced by
►Leydig cells of testis, Adrenal cortex,
Ovary, Placenta
►Responsible for development of male
secondary sex characteristics
Testosterone ►C-19 steroid
►Produced by:
►Corpus luteum; Placenta; Adrenal cortex
►Formation of progesterone from
pregnenolone involve
Progesterone
►C-21 steroid
►Synthesized in the:
►Ovary (major); Adrenal cortex; Placenta
►Functions include:
►Stimulate proliferation and differentiation of
vaginal epithelium
►Proliferation & hypertrophy of uterine
mucosa
►Proliferation of breast ducts
Estrogen
►complexes of protein and lipids with
noncovalent bonds
►major transporters of lipid
LIPOPROTEINS
LIPOPROTEINS sphere with ____________________ (phosphatidylcholine) and _________________ forming the outer shell
protein & amphipathic lipid, unesterified cholesterol
LIPOPROTEINS
► __________ segment
directed inward
► _____ segments face
the water outside
► __________________
(triglycerols and esterified cholesterol)
form inside of sphere
nonpolar, polar, nonpolar lipids
►Triacylglycerol that are given a coat
composed of proteins, phospholipids, and
cholesterol esters
►CHYLOMICRONS
►Transport triacylglycerol from the liver to
the tissues
►VERY-LOW DENSITY LIPOPROTEIN
(VLDL)
►initial products of VLDL degradation
►INTERMEDIATE DENSITY
LIPOPROTEIN (IDL)
►not steroid, but are related because they are
synthesized from five carbon isoprene units,
like cholesterol
POLYPRENOIDS
►lipids exposed to oxygen 🡪 Peroxidation
(auto-oxidation)
►deterioration of foods
FREE RADICALS
►control and reduce lipid peroxidation
antioxidants
Role of lipoproteins?
Transport of lipids from intestines as __________
Transport of lipids from liver as ______
Transport of lipids from adipose tissue as _____ bound to serum albumin
CHYLOMICRONS, VLDL, FFAs
A risk factor for increased mortality,
hypertension, type 2 diabetes mellitus and
other endocrine dysfunctions
OBESITY
CLASSES OF PLASMA LIPIDS
Cholesterol (____)
Triacylglycerols (____)
Phospholipids (____)
Cholesteryl esters (____)
Free fatty acids, FFAs (____)
14%, 16%, 30%, 36%, 4%
metabolically,
the most active of the plasma lipids
Free fatty acids, FFAs
Found in combination with albumin (a good
solubilizer)
Free fatty acids, FFAs
FREE FATTY ACIDS
________ in plasma in fully fed state → ______ in
starved state. ________ in uncontrolled
diabetes.
Low levels, rises, Increased levels
Removed from blood very quickly
Free fatty acids, FFAs
derived from intestinal absorption of
triacylglycerol (TAG) & other lipids
Chylomicrons
derived
from liver for the export of TAG
Very Low Density Lipoproteins (VLDL)
represents final
stage of VLDL catabolism
Low Density Lipoproteins (LDL)
involved in
cholesterol transport + VLDL and chylomicron
metabolism
High Density Lipoproteins (HDL)
LIPOPROTEINS
Structure
> nonpolar core =
_______________________
> outer layer = ___________________
triacylglycerol + cholesteryl ester, phospholipid + cholesterol
proteins that bind lipids to form lipoproteins
APOLIPOPROTEINS
Thought to have a role in chylomicron metabolism
May act as a regulator of satiety & glucose
homeostasis → potential therapeutic target for
treatment of diabetes and obesity
Apo A-IV
important factor in human neurodegenerative
disease
Apo D
Major apoproteins of HDL →
apo As
Main apoproteins of LDL →
apo B (B-100)
form LDL (“bad cholesterol”),
have beta sheet structure, stick to lipids irreversibly
Apolipoprotein B
form HDL (“good
cholesterol”), have alpha helix structures, stick to
lipids reversibly
apo A & other apolipoproteins
the primary protein in LDL (“bad cholesterol”)
One of the longest single polypeptide chains known
Apolipoprotein B100
Atherogenic
Most likely to enter the wall of the arteries
Apolipoprotein B
Found in chyle (formed by lymphatic system
draining the intestine)
Responsible for transport of all dietary lipids
into the circulation
transports triacylglycerol from liver to the
extrahepatic tissues
CHYLOMICRONS
Both are rapidly catabolized
Chylomicrons & VLDL
Where do fatty acids from chylomicron triacylglycerol go?
___ to adipose, heart & muscle
____ to liver
80%, 20%
Located on the walls of capillaries & anchored to
the endothelium by negatively charged
proteoglycan chains of heparan sulfate
Lipoprotein lipase
The LDL receptor is specific for _______
____ of LDL is degraded in extrahepatic
tissues; ____ degraded in liver
apo B-100, 30%, 70%
is made and secreted by both the liver &
intestine
HDL
storage site for apo C & apo E that are needed in metabolism of chylomicrons & VLDL
MAJOR FUNCTION OF HDL
Liver is the place of facilitation of digestion & absorption of lipids by production of _____
bile
Liver is the place of Conversion of fatty acids to _________________
ketone bodies
VLDL assembly requires _____________________
apo B-100 & TAG
accumulation of lipid, mainly TAG in the liver
Fatty liver
Most common liver disorder worldwide:
nonalcoholic
fatty liver
- protein involved in formation of lipid droplets in adipocytes
Enables storage and breakdown of TAG as needed by the
body
Perilipin
also catalyzed in vivo by heme compounds and
lipoxygenase found in platelets and leukocytes
Lipid Peroxidation
_________ are Associated with increased health risks
Trans fatty acids
Main product of Fatty Acid Oxidation
Acetyl-CoA