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 Acid
Omega-6
Linolenic Acid
Omega-3
Fatty Acid Isomers
 Lipid Content of Feeds

Forages
Fat content is low: 1 to 4% of dry matter
High proportion of linolenic acid (18:3)
Diglycerides in fats of leaves
Grains
Fat content variable: 4 to 20% of dry matter
High proportion of linoleic acid (18:2)
Triglycerides in oils of seeds
 Lipid Digestion - Rumen
-galactosidase
DigalDigly MonogalDigly

Galactose -galactosidase

Propionate Diglyceride

Glycerol Lipase Anaerovibrio

lipolytica

Triglyeride Fatty acids

Lipase
H+
Saturated FA Reductases
CaFA Ca++ Feed particles
 Fat Digestion
Digestibility influenced by:
Dry matter intake
Decreases with greater intake
Amount of fat consumed
Digestibility decreases 2.2% for each 100 g of FA
intake (Response is variable)
Degree of saturation
Digestibility decreases with increased saturation
Maximal digestion with fats having Iodine values
greater than 40
 Lipid Metabolism - In the Rumen
1. Minimal degradation of long-chain fatty acids in
the rumen
Fatty acids not a source of energy to microbes
2. Active hydrogenation of unsaturated fatty acids
3. 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
 Microbial Fatty Acid Synthesis

• 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.
 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 hydrogenated

Monounsaturated less than polyunsaturated
65 to 96% hydrogenation
Numerous isomers are produced
Biohydrogenation is greater when high forage
diets fed
Linoleic acid depresses hydrogenation of FA
 Conjugated Linoleic Acid (CLA) - Rumen
Most Common Pathway (High Roughage)

Linoleic acid (cis-9, cis-12-18:2)

Cis-9, trans-12 isomerase
Butyrivibrio fibrosolvens
Conjugated linoleic acid (CLA, cis-9, trans-11-
18:2)
Vaccenic acid (Trans-11-18:1)

Stearic acid (18:0)

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 available
for incorporation into tissue triglycerides.

Reactions from linoleic acid to vaccinic acid

occur at a faster rate than from vaccinic acid
to stearic acid.

Therefore, vaccinic acid accumulates in the

rumen and passes into intestines where it
is absorbed.

Quantities of vaccinic acid leaving the rumen

several 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 in

milk and tissues from ruminants.

Also transforms
Palmitic Palmitoleic
Stearic Oleic
 Potential Value of CLA in
Foods of Ruminant Origin
Anticarcinogenic
Lab animals given chemicals to cause cancer

Reduce atherosclerosis
Direct evidence with rabbits
Indirect evidence with humans

Reduce fat accumulation in the body

Laboratory animals and pigs
Evidence not conclusive with humans
 CLA Content of Foods

CLA isomers cis 9, trans 11

Food mg/g fat %
Beef 4.3 85
Pork 0.6 82
Chicken 0.9 84
Milk 5.5 92
Colby cheese 6.1 92
Corn 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 acids

Experimental milk: 5 to 25 mg CLA/g fatty acids

Less response if high-concentrate diets are fed

 High Concentrations of CLA Isomers
Increase in trans-10, cis-12-18:2 CLA isomer
when 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
Concentrations of Omega-3 and Omega-6 Fatty
Acids with Time Fed Grain - Cattle
9
8
% Total fatty acids

7
6
5
4 Omega-3
3 Omega-6
2
1
0
0 28 56 84 112 140 168 196
Days
Duckett et al., 1993
Ratio of Omega-6:Omega-3 Fatty Acids with
Time Fed Grain - Cattle

80
70
Omega-6/Omega-3

60
50
40
30
20
10
0
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

 cis9 trans11 CLA Concentrations in Milk
from Different Farms in Northeast Iowa
CLA c9, t11

1.40

1.20
Baker
% of total fatty acids

1.00 Bushman

0.80 Cline
Kime
0.60
Langland

0.40

0.20

0.00
Jan Feb Mar Apr May Jun Jul Aug Sep

2003
 Oleic Acid in Milk and Tissues

Oleic acid (18:1) is predominant fatty acid

in ruminant fat.

Stearic acid Oleic acid

Delta-9 desaturase

Delta-9 desaturase found in ruminant adipose

and mammary gland
 Fatty Acid Concentrations
% by Wt

FA Alf Grass Corn SB Bac Pro Beef Mut

14:0 0.9 1.1 0 0.1 3.9 1.5 3.7 2.6
16:0 33.9 16.9 10.9 10.3 31.0 37.8 24.2 23.0
18:0 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 1.9

18:1 3.0 3.4 24.1 22.8 6.0 11.5 43.7 37.9
18:2 24.0 13.2 58.0 51.0 2.7 6.3 2.6 2.2
18:3 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
 Fatty Acid Absorption

Epithelial cell
Triglycerides Lymph

Fatty acids Chylomicrons

x

Intestine Liver Pancreas

Free fatty acids
Bile salts Micelle
Phospholipases
Lecithin Lysolecithin
Phospholipids Fatty acids

Bile of ruminants contains predominantly taurine-conjugated bile acids

rather than glycine conjugate. The taurine conjugate is more effective
at acid pH
 Energy Value of Fats
In digestion and metabolism of fats:
No energy lost as methane
No 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 about
80% or ME x 0.80 = Net Energy
Gross Energy
Tallow - 9.2 Mcal/kg Free fatty acids - 9.39 Mcal/kg
Ca salts of free fatty acids - 8.03 Mcal/kg
Effects of Fats on Rumen Fermentation
Effects of adding fat to ruminant diets
Reduced feed intake
Reduced fiber digestion
Reduced milk fat
Increase 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 particles
Interfere with microbial attachment
Interfere with attachment of enzymes
Complex Ca
Direct antimicrobial effects
Cytotoxic effects on cell membranes
Interfere with energy metabolism
Free carboxyl group needed
Triglycerides less toxic than free fatty acids
Ca salts of fatty acids less toxic
 Metabolic Pathways in Ruminant Adipose

Adipose Cell Triglycerides

Glycerol-3-P

Free fatty acids

Glycerol
NADPH
Acetate Glucose

Glucose
Glycerol NEFA VLDL Acetate
Blood triglycerides Lipoprotein lipase
 Adding Fat to Ruminant Diets

Ruminant feeds normally contain low levels

of fats or oils - usually 2 to 4%.
Why add fat?
Increase energy density in the diet
Fat 2.5 times more energy
Increase milk production or gain
(Benefits should be greater than costs)
Secondary benefits:
Improve diet and pellet characteristics
Reduces dust
Lubricate feed processing equipment
Pellet mills, mixers, etc
 Adding Fat to Ruminant Diets

Need to add proper level and kind of fat

How much fat is in basal diet
Kind of fatty acids in basal diet
Level of production
Potential limitations
Hydrogenated fats less digestible
Unsaturated fatty acids depress fiber digestion
Decreased feed intake
Produce trans fatty acids and reduce milk fat
Usually limit the quantity of added fat to less
than 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
Unprotected
Animal fats (tallow, grease, etc)
More difficult to mix - Cold weather - Melt fats
Most commonly used as feed
Plant oils (soybean, corn, etc)
Unsaturated fatty acids depress fiber digestion
Usually cost prohibitive
Whole oil seeds
Soybeans, cotton seeds, high-oil corn
Oils are not as readily available
Less effect on rumen fermentation
Easiest 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 diet
Blended fats: yellow grease and animal + vegetable
 Finishing Steers - Rolled Barley
% Added fat
0 4 8
DM intake, kg/d 5.28 5.30 5.28
Rum dig starch, % 90.3 90.3 90.4
Rum dig ADF, % 27.3 19.0 6.7
SI dig, starch, % 77.3 80.6 78.7
SI dig, ADF, % 13.7 16.5 23.0
TT dig, starch, % 99.4 99.3 99.2
TT dig, ADF, % 45.5 41.1 37.4
Steers fed 88% concentrate diet
Blended fats: yellow grease and animal + vegetable
 Finishing Steers - Rolled Corn

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 than
other roughages
Stage of lactation
Energy balance
Greater response when cow needs energy
Composition of added fat
Unsaturated - saturated fatty acids
Availability of fat in the rumen
Amount of supplemental fat
Response is curvilinear
 Lactation Diets
Supplement during peak lactation
From 7 - 8 weeks to 11 - 15 weeks
Amount to feed
Milk production reaches maximal efficiency
when fatty acids contribute 16% of ME
Equates to about 600 to 700 g of
supplemental fat per day
Will 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 seeds
Available oil increased with processing
Extruding - heat
Usually minimal effects on rumen fermentation
Unprotected fats
Tallow - saturated fatty acids
Add up to amount that will not affect
rumen fermentation
Protected fats
Use if addition of unprotected fat does
not 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 hulls
Choice 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 hulls
Choice white grease
 Effects of Supplemental Fat on Reproduction

Variables
Animal: 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, unless

control animals are energy deficient

Response
Metabolic hormones – Insulin, growth hormone, IGFs
Cholesterol – Progesterone concentrations
LH secretion and follicular development
Prostaglandin synthesis –PGF2