Exam #3 Flashcards
Simple Lipids
- ) Fatty Acids
- ) Triacylglycerols, diacylglycerols, and monoacylglycerols
- ) Waxes (esters of fatty acids with higher alcohols)
includes: sterol esters (cholesterol - fatty acid esters) and nonsterol esters (vitamin A esters)
Compound Lipids
1.) Phospholipids
Includes: Phosphatidic acids, Plasmalogens, Sphingomyelins
- ) Glycolipids (CHO containing)
- ) Lipoproteins (lipids associated with protein)
Lipids in Human Nutrition
Fatty Acids
Triacylglycerols
Sterols & Steroids
Phospholipids
Glycolipids
Fatty Acids
Simplest of lipids
Straight hydrocarbon chain
polar hydophilic end (carboxyl group) terminating end
nonpolar hydrophobic end (methyl group) insoluble
important energy nutrient furnishing most of the calories from dietary fat
chains vary from 4 (butyric acid) to 24 carbon atoms
Functional Groups makes 2 things possible:
- ) attach to other things (ie glycerol and protein)
- ) hydrophilic likes water
Most FA have an even number of carbon atoms - this is because building block Actyl CoA (2C)
Odd-numbered FAs do occur naturally to some extent (seafood)
Cis Isomerism
unsaturated
folding back and kinking
U like orientation
most naturally occurring
Hydrogens on adjacent Cs attached by double bond are either both up or both down (same side)
Trans Isomerism
unsaturated
extending molecule into linear shape similar to that of saturated fatty acids
partially hydrogenated fats and oils
margarine and frying oils designed to be solids at room temp
trans= 1H up and 1H down on adjacent carbons (more straight) (opposite sides)
Delta Nomenclature
Ex: 18:2 Δ9,12 linoleic acid
18 = 18 carbons
2 = 2 double bonds
9,12 = carbon atoms at which double bond begins (numbering starts from carboxyl end)
Omega Nomenclature
Ex: 18:2 n-6 linoleic acid
18 = 18 carbon atoms
2 = 2 double bonds
n-6 = loaction of carbon atom of the first double bond (starts counting from the methyl end)
** Takes into account that double bonds in a fatty acid are always separted by 3 carbons**
omega 6 = 2 double bonds
omega 3 = 3 double bonds
Saturated Fatty Acid
SFA
contains no double bonds
packs a lot of lipids in a small space packaged well
Palmitic Acid
saturated fatty acid
16Cs with no double bonds (16:0)
animal and plant fats
CH3-(CH2)14-COOH
Fatty Acid Synthesis: glucose->fat make palmitic acid first
Stearic Acid
saturated - solids at room temp
18C length no double bonds (18:0)
animal fats (beef), and some plant fats
CH3-(CH2)16-COOH
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Monounsaturated
MUFA
possessing one carbon-carbon double bond
Palmitoleic Acid
Monounsaturated fatty acid
16Cs and 1 double bond (16:1Δ9 (n-7))
marine animal oils, small amt of plant and animal fats
CH3-(CH2)5-CH=CH-(CH2)7-COOH
Oleic Acid
unsaturated fatty acid
18Cs and 1 double bond (18:1)
plant and animal fats
CH3-(CH2)7-CH=CH-(CH2)7-COOH
olive oil (usually oils are mixtures oleic is found in a lot of stuff)
Polyunsaturated
PUFA
have two or more carbon-carbon double bonds
may have as many as 6 double bonds
Linoleic Acid
polyunsaturated fatty acid
18Cs 2 double bonds (18:2Δ9,12 (n-6))
corn, safflower, soybean, cottonseed, sunflower seed, and peanut oil
CH3-(CH2)4-CH=CH-CH2-CH=CH-(CH2)7-COOH
essential fatty acid
Be able to draw!
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α-linolenic acid
Polyunsaturated fatty acid
18Cs 3 double bonds (18:3Δ9,12,15 (n-3))
linseed, soybean, and other seed oils
CH3-CH2-CH=CH-CH2-CH=CH-CH2-CH=CH-(CH2)7-COOH
or
CH3-(CH2-CH=CH)3-(CH2)7-COOH
essential fatty acid
Fatty Acid Length
fatty acids with 14 or more carbon atoms are most important nutritionally and functionally
The following account for 90% of US diet:
palmitic acid (16:0)
stearic acid (18:0)
oleic acid (18:1)
linoleic acid (18:2)
In milk fat and coconut oil: butyric acid (4:0) and lauric acid (12:0)
Melting Point
more saturation = higher melting point
longer chain - higher melting point
MP high for saturated fat bc double bond gives space between structure so heat can escape not as tightly packed
Trans FA
partially hydrogenated fat (margerine; shortening)
problem: creates unnatural double bond
Foods: cookies, cakes, mostly baked goods
accumulate in the body (too straight)
Essential Fatty Acids
linoleic (18:2 n-6)
α-linolenic acid (18:3 n-3) not common
prevents blood coagulation, lowers cholesterol, contains immunities, and hormone like regulations
essential bc humans lack enzymes called Δ12 and Δ15 desaturases, which incorporate double bonds at these positions (found only in plants)
humans can’t form double bonds beyond the Δ9 carbon in chain
FA elongation by enzymatic addition of 2 carbons @ carboxyl end of chain
EFA can make other FAs
Linoleic acid (18:2 n-6) -> γ-linolenic acid (18:3 n-6) -> Eicosatienoic acid (20:3 n-6) (intermediate) -> Arachidonic acid (20:4 n-6)
n-3 Fatty Acids (omega 3s)
nutritional interest
hypolipidemic and antithrombotic effects
α-linolenic acid (18:3 n-3) vegetable oils
Docosahexaenoic acid DHA (22:6 n-3) fish oils
Eicosapentaenoic acid EPA (20:5 n-3) precursor of physiological important eicosanoids
fish oils particularly good source (lower lipid in blood and anti-blood clotting)
Triacylglycerols (TAG)
Structure
3 fatty acids and a glycerol attached by ester bonds results in a lose of a water molecule
FA maybe all same (simple TG)
FA maybe different (mixed TG)
mostly stored body fat (highly concentrated energy)
95% of dietary fat
the 3 Carbons of glycerol each are disguishable by enzymes with specificity for one particular carbon
these 3 Carbons are number 1,2,3
C-2 has hydroxyl group to the left
TAG are fat or oil at room temp
SCFA or UFA liquid/oil
SFAs of longer chain length solid (high MP)
What makes fat solid? lack of double bonds and length (longer needs more heat)
Energy (free fatty acids during starvation)
FA released in free form from TAGs in adipocytes by hormone sensitive lipase (HSL)
FFA are transported by albumin to other tissues for oxidation
Sterols and Steroids
class of lipids characterized by a four-ring core structure (steroid)
monohydroxy alcohols of steroidal structure
Cholesterol (most common)
sources: meat, egg yolk, and dairy products
exists in free form or hydroxyl group is esterified to FA
free form is absorbable
cholesteryl ester is not absorbed its too large
Chol is essential component of cell membranes (nerve tissue)
Chol serves as precursor for:
bile acids, steroid sex hormones (estrogen, progesterone), adrenocortical hormones, vit D of animal tissues
bile salts important bc emulsifies fat needs hydrophobic and hydophilic
each differ in arrangement of DBs, presenxe of carbonyl or hydroxyl groups, nature of side chain at C-17
all these structural modifications are mediated by enzymes
Not Essential - does have good functions
Sterols and phospholipids only make up 5% of dietary lipids when combined
Phospholipids
contain phosphate
possess one or more FAs
2 Types:
- ) Glycerophosphatides - core structure is glycerol (3C)
- ) Sphingophosphatides - core structure is the amino alcohol sphingosine (palmitic acid + serine = 18C)
More polar than TAGs and Sterols (attract water molecules) on surface of chylomicrons
are polar - bc of this hydrophilic property are on the surface of blood-borne lipid particles such as chylomicrons which stablizes the particles in aqueous material
Serve as regulators of passage of water and fat-soluble materials across membrane
Important:
- memory structures
- emulsifiers
- myelin nerve protection
- enzymes 2nd messages and anchors
Glycerophosphatides
FAs at C-1 (saturated) and C-2 (unsaturacted) of glycerol (nonpolar)
phosphoric acid at C-3 of glycerol (polar)
serve as structural support to the membrane and source of physiologically active compounds
phosphatidic acid from a number of derivatives:
- phosphatidylcholine** (lecithin)** - most common, is in egg yolk, good emulsifier melts in mouth makes smooth texture in chocolate
- phosphatidylethanolamine**
- phosphatidylserine**
- phosphatidylinositol** -
A. anchoring membrane PTNs when PTNs are covalently attached to lipids. (observed in cells treated with PI-specific phospholipase C caused hydrolyzing of ester bond connecting glycerol to phosphate
B. also active in intracellular signaling they act as 2nd messengers in hormone stimulation (insulin) (cause release of Ca -\> Ca depend enzymes)
Sphingolipids
not as common
found in cell membrane
emulsifer
myelin sheath - nervous tissue
- sphingomyelins
Glycolipids
2 Types:
- cerebrosides
- gangliosides
have CHO component in structure
occur in medullary sheaths of nerves and in brain tissue
shingosine backbone and don’t contain phosphate