Triacylglycerol Triglycerides R-COO-CH 2 R-COO-CH R-COO-CH 2 • Triglycerides found in seeds and animal adipose. • Diglycerides found in plant leaves, one fatty acid is replaced by sugar (galactose).
Jan 05, 2016
Triacylglycerol Triglycerides
R-COO-CH2
R-COO-CH R-COO-CH2
• Triglycerides found in seeds and animal adipose.• Diglycerides found in plant leaves, one fatty acid is replaced by sugar (galactose).
Most Common Fatty Acids in Di- and Triglycerides
Fatty acid Carbon:Double bonds Double bonds
Myristic 14:0
Palmitic 16:0
Palmitoleic 16:1 Cis-9
Stearic 18:0
Oleic 18:1 Cis-9
Linoleic 18:2 Cis-9,12
Linolenic 18:3 Cis-9,12,15
Arachidonic 20:4 Cis-5,8,11,14
Eicosapentaenoic 20:5 Cis-5,8,11,14,17
Docosahexaenoic 22:6 Cis-4,7,10,13,16,19
CH3(CH2)nCOOH
Triglyceride Containing Linoleic AcidOmega-6
Linolenic AcidOmega-3
Fatty Acid Isomers
Lipid Content of Feeds
ForagesFat content is low: 1 to 4% of dry matterHigh proportion of linolenic acid (18:3)Diglycerides in fats of leaves
GrainsFat content variable: 4 to 20% of dry matterHigh proportion of linoleic acid (18:2)Triglycerides in oils of seeds
Lipid Digestion - Rumen
DigalDigly MonogalDigly
Galactose
Propionate Diglyceride
Glycerol
Triglyeride Fatty acids
Saturated FA CaFA Ca++ Feed particles
-galactosidase
-galactosidase
Lipase Anaerovibrio lipolytica
H+
Reductases
Lipase
Fat Digestion
Digestibility influenced by:Dry matter intake
Decreases with greater intakeAmount of fat consumed
Digestibility decreases 2.2% for each 100 g of FA intake (Response is variable)
Degree of saturationDigestibility decreases with increased saturationMaximal digestion with fats having Iodine values greater than 40
1. Minimal degradation of long-chain fatty acids in the rumen
Fatty acids not a source of energy to microbes2. Active hydrogenation of unsaturated fatty acids3. Microbial synthesis of long-chain fatty acids in the rumen (15g/kg nonfat org matter fermented)4. No absorption of long chain fatty acids from the rumen
More fat leaves the rumen than consumed by the animal
Lipids leaving the rumen• 80 to 90% free fatty acids attached to feed particles and microbes• ~10% microbial phospholipids leave the rumen• Small quantity of undigested fats in feed residue
Lipid Metabolism - In the Rumen
• Synthesize C 18:0 and C 16:0 in 2:1 ratio using acetate and glucose (straight-chain even carbon #).• If propionate or valerate used, straight-chain odd carbon fatty acids synthesized.• Branched-chain VFA used to produce branched chain fatty acids.• About 15 to 20% of microbial fatty acids are mono- unsaturated. No polyunsaturated fatty acids are synthesized.• Some incorporation of C 18:2 into microbial lipids.
Microbial Fatty Acid Synthesis
Hydrogenation of Fatty Acids in the Rumen
Polyunsaturated fatty acids (all cis)Isomerase (from bacteria) Needs free carboxyl group
and diene double bond
Shift of one double bond (cis & trans)
Hydrogenation Hydrases (from bacteria,
Hydrogenated fatty acid mostly cellulolytic)
(stearic and palmitate)
Hydrogenation of Fatty Acids in the Rumen
All unsaturated fatty acids can be hydrogenatedMonounsaturated less than polyunsaturated
65 to 96% hydrogenationNumerous isomers are producedBiohydrogenation is greater when high foragediets fedLinoleic acid depresses hydrogenation of FA
Conjugated Linoleic Acid - RumenMost Common Pathway (High Roughage)
Linoleic acid (cis-9, cis-12-18:2)
Conjugated linoleic acid (CLA, cis-9, trans-11-18:2)
Vaccenic acid (Trans-11-18:1)
Stearic acid (18:0)
Cis-9, trans-12 isomerase Butyrivibrio fibrosolvens
CLA Isomers - Rumen (High Concentrate)Low Rumen pH
Linoleic acid (cis-9, cis-12-18:2) Cis-9, trans-10 isomerase
CLA Isomer (trans-10, Cis-12-18:2)
This isomer is inhibitory to milk fat synthesis.
Trans-10-18:1
Linolenic Acid – Oleic Acid
Linolenic acid (cis-9, cis-12, cis-15-18:3)
(Cis-9, trans-11, cis-15-18:3)
Trans-11, cis-15-18:2
Trans-11-18:1 (vaccenic acid)
Oleic acid cis-9 (18:1) Stearic acid (18:0)
CLA absorbed from the intestines availablefor incorporation into tissue triglycerides.
Reactions from linoleic acid to vaccinic acidoccur at a faster rate than from vaccinic acidto stearic acid.
Therefore, vaccinic acid accumulates in therumen and passes into intestines where itis absorbed.
Quantities of vaccinic acid leaving the rumenseveral fold greater than CLA.
Conversion of Vaccinic Acid to CLA In mammary gland and adipose
Trans-11-18:1 CLA, cis-9, trans-11 18:2
Stearoyl CoA Desaturase‘9-desaturase’
This reaction probably major source of CLA inmilk and tissues from ruminants.
Also transformsPalmitic PalmitoleicStearic Oleic
Potential Value of CLA in Foods of Ruminant Origin
AnticarcinogenicLab animals given chemicals to cause cancer
Reduce atherosclerosisDirect evidence with rabbitsIndirect evidence with humans
Reduce fat accumulation in the bodyLaboratory animals and pigsEvidence not conclusive with humans
CLA Content of Foods
CLA isomers cis 9, trans 11Food mg/g fat %
Beef 4.3 85Pork 0.6 82Chicken 0.9 84Milk 5.5 92Colby cheese 6.1 92Corn oil 0.2 39
Increasing CLA in Foods of Ruminant Origin
• Grazing grass increases CLA concentration in meat and milk from ruminants• Feeding Ca-salts of unsaturated fatty acids• Processing full fat soybeans to release oil
Extrusion, roasting, heating temperature• Feeding fish oil• Feeding high oil corn - minimal effects
Control milk: 3 to 4 mg CLA/g fatty acidsExperimental milk: 5 to 25 mg CLA/g fatty acids
Less response if high-concentrate diets are fed
Increase in trans-10, cis-12-18:2 CLA isomerwhen unsaturated oils fed in high-grain diets
• Low rumen pH seems to increase trans fatty acids in the rumen • Decrease milk fat• Trans fatty acids increase in low fat milk
High Concentrations of CLA Isomers
Concentrations of Omega-3 and Omega-6 Fatty Acids with Time Fed Grain - Cattle
0123456789
% T
ota
l fa
tty
acid
s
0 28 56 84 112 140 168 196
Days
Omega-3
Omega-6
Duckett et al., 1993
Ratio of Omega-6:Omega-3 Fatty Acids with Time Fed Grain - Cattle
0
10
20
30
40
50
60
70
80
Om
ega-
6/O
meg
a-3
0 28 56 84 112 140 168 196
Days
Stearoyl CoA Desaturase (9-Desaturase) in Wagyu and Holstein Steers
Wagyu Holstein
Muscle 3.3 0.8
Adipose 132.1 39.5
Mono Unsat, % 57.3 53.4
Yang et al., 1999
CLA c9, t11
0.00
0.20
0.40
0.60
0.80
1.00
1.20
1.40
2003
% o
f to
tal f
atty
aci
ds
Baker
Bushman
Cline
Kime
Langland
Feb Mar Apr May Jul Aug SepJunJan
cis9 trans11 CLA Concentrations in Milkfrom Different Farms in Northeast Iowa
Oleic Acid in Milk and Tissues
Oleic acid (18:1) is predominant fatty acidin ruminant fat.
Stearic acid Oleic acid Delta-9 desaturase
Delta-9 desaturase found in ruminant adiposeand mammary gland
Fatty Acid Concentrations% by Wt
FA Alf Grass Corn SB Bac Pro Beef Mut14:0 0.9 1.1 0 0.1 3.9 1.5 3.7 2.616:0 33.9 16.9 10.9 10.3 31.0 37.8 24.2 23.018:0 3.8 2.0 1.8 3.8 15.0 13.5 13.5 25.8
16:1 1.2 2.5 0 0.2 4.0 6.8 6.0 1.918:1 3.0 3.4 24.1 22.8 6.0 11.5 43.7 37.918:2 24.0 13.2 58.0 51.0 2.7 6.3 2.6 2.218:3 31.0 61.3 0.7 6.8 1.0 4.7
Postruminal Fat Digestion and Absorption
• Fatty acids from the rumen mostly saturated• No absorption of fatty acids from the rumen• Fatty acids attached to feed particles, Ca and microbes dissociate in the acid environment of the abomasum• pH of duodenum and jejunum remains acidic in ruminants
- Affects solubility of fatty acids in aqueous environment• Fatty acid emulsification and micelle formation in the small intestine is essential for efficient absorption• Fatty acids absorbed predominantly from the jejunum into lymph
Intestine Liver PancreasFree fatty acids
Bile salts Micelle Phospholipases
Lecithin LysolecithinPhospholipids Fatty acids
Epithelial cellTriglycerides Lymph
Fatty acids Chylomicronsx
Fatty Acid Absorption
Bile of ruminants contains predominantly taurine-conjugated bile acidsrather than glycine conjugate. The taurine conjugate is more effectiveat acid pH
In digestion and metabolism of fats:No energy lost as methaneNo energy lost in the urine
So: Digestible energy = metabolizable energy Energy value of fat determined by digestibility
Digestibility of supplemental fats is variable
Use of metabolizable energy from fat is about80% or ME x 0.80 = Net Energy
Gross EnergyTallow - 9.2 Mcal/kg Free fatty acids - 9.39 Mcal/kgCa salts of free fatty acids - 8.03 Mcal/kg
Energy Value of Fats
Effects of Fats on Rumen Fermentation
Effects of adding fat to ruminant dietsReduced feed intakeReduced fiber digestionReduced milk fatIncrease propionate/acetate ratio
• Polyunsaturated fats more inhibitory than saturated fats• Feeding oil seeds of polyunsaturated fats less inhibitory• Up to 3% of diet as tallow or yellow grease can be fed without major effects
Mechanism of Inhibition
Lipids coat feed particlesInterfere with microbial attachmentInterfere with attachment of enzymesComplex Ca
Direct antimicrobial effectsCytotoxic effects on cell membranes
Interfere with energy metabolismFree carboxyl group needed
Triglycerides less toxic than free fatty acidsCa salts of fatty acids less toxic
Metabolic Pathways in Ruminant Adipose
Adipose Cell TriglyceridesGlycerol-3-P
Free fatty acidsGlycerol
NADPHAcetate Glucose
GlucoseGlycerol NEFA VLDL AcetateBlood triglycerides Lipoprotein lipase
Adding Fat to Ruminant Diets
Ruminant feeds normally contain low levelsof fats or oils - usually 2 to 4%.
Why add fat?Increase energy density in the diet
Fat 2.5 times more energyIncrease milk production or gain(Benefits should be greater than costs)
Secondary benefits:Improve diet and pellet characteristics
Reduces dustLubricate feed processing equipment
Pellet mills, mixers, etc
Adding Fat to Ruminant Diets
Need to add proper level and kind of fatHow much fat is in basal dietKind of fatty acids in basal dietLevel of production
Potential limitationsHydrogenated fats less digestibleUnsaturated fatty acids depress fiber digestionDecreased feed intakeProduce trans fatty acids and reduce milk fat
Usually limit the quantity of added fat to lessthan 5% of total diet of ruminants
Types of Fat Fed to Ruminants
Rumen inert (Protected) Ca salts of fatty acids, hydrogenated fats
Have little if any effects on fiber digestion in the rumen
Sold commercially in dry form Easy to mix Expensive source of fat
UnprotectedAnimal fats (tallow, grease, etc)
More difficult to mix - Cold weather - Melt fatsMost commonly used as feed
Plant oils (soybean, corn, etc)Unsaturated fatty acids depress fiber digestionUsually cost prohibitive
Whole oil seedsSoybeans, cotton seeds, high-oil cornOils are not as readily availableLess effect on rumen fermentationEasiest for smaller producers to feed
Finishing Steers - Rolled Barley
% Added fat
0 4 8
Feed DM, kg/d 6.19 6.18 6.42
ADG, kg/d 0.83 0.92 1.02
Feed/gain 7.51 6.80 6.30
Back fat, cm 1.17 1.23 1.33
Marbling 4.09 4.21 4.35
305 kg steers fed 88% concentrate dietBlended fats: yellow grease and animal + vegetable
Finishing Steers - Rolled Barley
% Added fat0 4 8
DM intake, kg/d 5.28 5.30 5.28Rum dig starch, % 90.3 90.3 90.4Rum dig ADF, % 27.3 19.0 6.7SI dig, starch, % 77.3 80.6 78.7SI dig, ADF, % 13.7 16.5 23.0TT dig, starch, % 99.4 99.3 99.2TT dig, ADF, % 45.5 41.1 37.4
Steers fed 88% concentrate dietBlended fats: yellow grease and animal + vegetable
Finishing Steers - Rolled Corn
--- 0 Fat--- --4% Tallow--
Monensin 0 + 0 +
Feed DM, kg/d 9.86 10.04 9.95 9.06
ADG, kg/d 1.38 1.52 1.48 1.32
Gain/feed 0.139 0.151 0.149 0.145
Back fat, cm 1.22 1.37 1.37 1.22
Marbling 5.75 5.50 5.22 5.03
350 kg steers fed 93% concentrate diet
Adding Fat to Lactation Diets
Factors affecting response to supplemental fat:Basal diet
Digestibility of corn silage affected more thanother roughages
Stage of lactationEnergy balance
Greater response when cow needs energyComposition of added fat
Unsaturated - saturated fatty acidsAvailability of fat in the rumen
Amount of supplemental fatResponse is curvilinear
Lactation Diets
Supplement during peak lactationFrom 7 - 8 weeks to 11 - 15 weeks
Amount to feedMilk production reaches maximal efficiencywhen fatty acids contribute 16% of ME
Equates to about 600 to 700 g ofsupplemental fat per dayWill support about 3.5 kg increase in milk
Total dietary fat should not exceed 6 to 7% of dietary DM
Lactation Diets
Full fat oil seedsAvailable oil increased with processing
Extruding - heatUsually minimal effects on rumen fermentation
Unprotected fatsTallow - saturated fatty acids
Add up to amount that will not affectrumen fermentation
Protected fatsUse if addition of unprotected fat doesnot meet the energy needs
More expensive
Adding Fat - Lactation
Choice white grease, %
0 2 4
DMI, kg/d 26.3 24.4 23.8
Milk, kg/d 42.3 41.5 38.1
Fat, % 3.30 2.93 2.85
Fat, kg/d 1.39 1.21 1.08
50% corn silage
Adding Fat - Lactation
21% ADF 28% ADF
Added fat 0 6 0 6
DMI, kg/d 24.4 21.7 23.7 21.5
Milk, kg/d 37.5 38.9 34.7 38.0
Fat, % 3.4 2.9 3.5 3.2
Fat, kg/d 1.3 1.1 1.2 1.2
Corn silage, alfalfa hay & cottonseed hullsChoice white grease
Adding Fat - Lactation
21% ADF 28% ADF
Added fat 0 6 0 6
VFA, mM 90.1 84.2 89.8 80.8
Acetate, % 61.8 58.2 66.3 64.0
Propionate, % 21.3 25.4 17.7 20.2
Butyrate, % 11.8 10.0 11.4 10.2
Corn silage, alfalfa hay & cottonseed hullsChoice white grease
Effects of Supplemental Fat on Reproduction
VariablesAnimal: Body condition score, age (parity), nutrients available
Type of fat: Digestibility, fatty acid composition, quantity of fat
Research is inconclusive on response to added fat, unlesscontrol animals are energy deficient
ResponseMetabolic hormones – Insulin, growth hormone, IGFsCholesterol – Progesterone concentrationsLH secretion and follicular developmentProstaglandin synthesis –PGF2