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Lipid Structure and Function. Pages 27-36 in textbook. Common Physical Properties of Lipids. Soluble in non-polar organic solvents Contain C, H, O Sometimes N & P Includes fats and oils – mostly triglycerides Fat: solid at room temperature Oil: liquid at room temperature

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lipid structure and function

Lipid Structure and Function

Pages 27-36 in textbook

common physical properties of lipids
Common Physical Properties of Lipids
  • Soluble in non-polar organic solvents
  • Contain C, H, O
    • Sometimes N & P
  • Includes fats and oils – mostly triglycerides
    • Fat: solid at room temperature
    • Oil: liquid at room temperature
  • More highly reduced than CHO
    • 2.25x more energy
lipids or glucose for energy
Lipids or Glucose for Energy?

Energy-Containing Nutrients (C and H)

ATP

H+

Electron

Transport

Chain

CO2

O2

H2O

lipids or glucose for energy1

More reduced state (more H bound to C)

 More potential for oxidation

Less reduced state (more O bound to C)

 Less potential for oxidation

Lipids or Glucose for Energy?
energy from lipids
Energy from Lipids
  • Compared to carbohydrates, fatty acids contain more hydrogen molecules per unit of carbon, thus, they are in a more reduced form
  • Carbohydrates are partially oxidized so they contain less potential energy (H+ and e-) per unit of carbon
functions and properties
Functions and Properties
  • Concentrated source of energy (9 kcal/gm)
  • Energy reserve: any excess energy from carbohydrates, proteins and lipids are stored as triglycerides in adipose tissues
  • Provide insulation to the body from cold
    • Maintain body temperature
  • Mechanical insulation
    • Protects vital organs
functions and properties1
Functions and Properties
  • Electrical insulation
    • Protects nerves, help conduct electro-chemical impulses (myelin sheath)
  • Supply essential fatty acids (EFA)
    • Linoleic acid and linolenic acid
  • Formation of cell membranes
    • Phospholipids, a type of fat necessary for the synthesis of every cell membrane (also glycoproteins and glycolipids)
functions and properties2
Functions and Properties
  • Synthesis of prostaglandins from fatty acids
    • Hormone-like compounds that modulates many body processes
      • Immune system, nervous systems, and GI secretions
      • Regulatory functions: lower BP, blood clotting, uterine contractions
  • Help transport fat soluble vitamins
  • Palatability and aroma
    • Flavor and taste for some species!
  • The satiety value – help control appetite
    • Fullness; fats are digested slower
      • Regulated through gastric inhibitory protein (GIP) and cholecystokinin (CCK)
physical traits of fatty acids
Physical Traits of Fatty Acids
  • Form membranes, micelles, liposomes
    • Orient at water:oil interface
    • Contain hydrophobic and hydrophilic groups
    • Lipid bilayer for membranes
    • Micelles formed during digestion
physical traits of fatty acids1
Physical Traits of Fatty Acids
  • Fatty acids form “soaps” with cations
    • Na & K soaps – water soluble
    • Ca & Mg soaps – not water soluble
      • Poorly digested
  • Major issue in feeding fats to ruminants
physical traits of fatty acids2
Physical Traits of Fatty Acids
  • Unsaturated fatty acids oxidize spontaneously in presence of oxygen
    • Auto-oxidation, peroxidation, rancidity
    • Free radicals formed
      • Reduce nutritional value of fats
    • Antioxidants prevent oxidation
      • Vitamins C and E, selenium
fatty acid structure
Fatty Acid Structure

- H

- H

= O

H - C - ( C )n - C - OH

Carboxyl group

- H

- H

Carbon group(s)

Methyl group

fatty acids
Fatty Acids
  • With a few exceptions, natural fatty acids:
    • Contain an even number of carbon atoms
    • Arranged in an unbranched line
    • Have a carboxyl group (-COOH) at one end
    • Have a methyl group (CH3) at the other end
fatty acid chain length
Fatty Acid Chain Length
  • Short chain: 2 to 6 C (volatile fatty acids)
  • Medium chain: 8 – 12 C
  • Long chain: 14 – 24 C
  • As chain length increases, melting point increases
  • Fatty acids synthesized by plants and animals have an even number of carbons
    • Mostly long chain
    • 16C to 18C fatty acids are most prevalent
fatty acid saturation
Fatty Acid Saturation
  • Saturated - no double bonds
  • Unsaturated – contain double bonds
    • Monounsaturated – one double bond
    • Polyunsaturated - >1 double bond
    • The double bond is a point of unsaturation
  • As number of double bonds increases, melting point decreases
saturated fats
Saturated Fats
  • All the chemical bonds between the carbon are single bonds C-C-C-
  • No double bonds
  • No space for more H atoms; fully “saturated”
  • Solid at room temperature
    • Butter, shortening, lard, coconut oil, palm oil, and fully hydrogenated vegetable oils
    • Poultry skin, whole milk
mono unsaturated fatty acids
Mono-Unsaturated Fatty Acids
  • Only one double bond
    • Therefore, two H atoms can be added
  • Liquid at room temperature
    • Olive oil, canola oil, peanut oil
    • Other sources: avocado, almonds, cashews, pecans and sesame seeds (tahini paste)
poly unsaturated fatty acids
Poly-Unsaturated Fatty Acids
  • Two or more double bonds
  • Include omega-3 and omega-6 fatty acids (essential fatty acids)
    • Linolenic acid: omega 3 fatty acid
    • Linoleic acid: omega 6 fatty acid
  • Richest sources of poly-unsaturated fatty acids include:
    • Vegetable oils
      • Corn, sunflower, safflower, cotton seed oils
saturation
Saturation
  • Unsaturated fatty acids
    • Converted to saturated fatty acids by rumen microbes
    • More susceptible to rancidity
      • Oxidation of double bonds produces peroxides and free radicals, which can cause damage to other compounds
  • Antioxidants
    • Vitamins E, C
    • Carotenoids
      • Such as beta-carotene, lycopene
    • Selenium
hydrogenation of fatty acids
Hydrogenation of Fatty Acids
  • To protect fats from becoming rancid, poly-unsaturated fatty acids may be hydrogenated
    • Increases saturation and stability - more resistant to oxidation
    • Unsaturated fats entering rumen are naturally hydrogenated (“bio”-hydrogenated)
    • Transforms the H-H configuration from cis to trans configuration
      • Trans configuration alters biological availability
      • Trans configuration alters biological effects
review of fatty acid nomenclature
Review of Fatty Acid Nomenclature
  • Chain length
    • Most fatty acids have an equal number of carbons
      • Fish oil is rich in odd-numbered FAs
  • Double bonds
    • Number
    • Location from methyl or carboxyl end
    • Degree of “saturation”
fatty acid nomenclature
Fatty-acid Nomenclature
  • Named according to chain length
    • C18
fatty acid nomenclature1
Fatty-acid Nomenclature
  • Named according to the number of double bonds
    • C18:0

Common name:

Stearic acid

fatty acid nomenclature2
Fatty-acid Nomenclature
  • Named according to the number of double bonds
    • C18:1

Common name:

Oleic acid

fatty acid nomenclature3
Fatty-acid Nomenclature
  • Named according to the number of double bonds
    • C18:2

Common name:

Linoleic acid

fatty acid nomenclature4
Fatty-acid Nomenclature
  • Named according to the number of double bonds
    • C18:3

Common name:

Linolenic acid

fatty acid nomenclature5
Fatty-acid Nomenclature
  • Named according to the location of the first double bond from the non-carboxyl end (count from the methyl end)
    • Omega system (e.g., omega 3, 3)
    • n–system (e.g., n–3)
fatty acid nomenclature6
Fatty-acid Nomenclature

Omega 9 or n–9 fatty acid

Omega 6 or n–6 fatty acid

Omega 3 or n–3 fatty acid

fatty acid synthesis issues
Fatty Acid Synthesis Issues

Ω-3

Ω-6

Ω-9

C-C-C=C-C-C=C-C-C=C-C-C-C-C-C-C-C-COOH

  • Animals can synthesize a fatty acid with a double bond in the omega 9 position but not at either 3 or 6 positions
    • Omega-3 and omega-6 fatty acids must be derived from diet
  • Cold water fish accumulate high levels of omega 3 fatty acids from their diet
omega system and essential fatty acids
Omega System and Essential Fatty Acids
  • Linoleic acid is an omega-6 fatty acid
  • Linolenic and arachidonic acids are omega-3 fatty acids
    • Linoleic and linolenic acids are essential fatty acids
    • Arachidonic acid can be synthesized from linoleic acid, so not essential
      • Exception is cats (of course)
fatty acid nomenclature7
Fatty-acid Nomenclature
  • Named according to location of H’s
    • Cis or trans fatty acids
fatty acid nomenclature8

H

H

H

H

2

2

2

H

C

C

C

C

C

3

C

C

C

C

H

H

H

H

2

2

2

2

Fatty-acid Nomenclature
isomers
Geometrical isomers due to double bond

Cis

occurs naturally

bend in acyl chain

Trans

Not as common

Found in hydrogenated oils

Results from bacterial synthesis

In fats in ruminants!!

Straight acyl chains

Chain branching

Straight

Synthesized by mammals and plants

Branched

Synthesized by bacteria

Isomers
melting points
Melting Points
  • Affected by chain length
    • Longer chain = higher melting temp

Fatty acid:C12:0 C14:0 C16:0 C18:0 C20:0

Melting point:44°C 58°C 63°C 72°C 77°C

Which fatty acids are liquid at room temperature?

Which fatty acids are solid at room temperature?

chain length
Chain Length
  • In most fats with a mixture of fatty acids, the chain length of the majority of fatty acids will determine the “hardness” of the fat
    • <10 carbons = liquid
    • Between 10 and 20 carbons = ???
    • >20 carbons = solid
melting points1
Melting Points
  • Affected by number of double bonds
    • More saturated = higher melting temp

Fatty acid:C18:0 C18:1 C18:2 C18:3

Melting point:72°C 16°C –5°C –11°C

Which fatty acid is liquid at room temperature?

Which fatty acids are solid at room temperature?

essential fatty acids
Essential Fatty Acids
  • Must be in diet
    • Tissues can not synthesize
    • Linoleic acid (18:2)
      • Omega-6-FA
    • Linolenic acid (18:3)
      • Omega-3-FA
    • Arachidonic (20:4)
      • Not found in plants!
      • Can be synthesized from C18:2 (linoleic acid) in most mammals (except in cat)
        • Essential nutrient in the diet of cats
functions of essential fatty acids
Functions of Essential Fatty Acids
  • A component of the phospholipids in cell membranes
  • Precursor for prostaglandins: arachidonic acid
  • Important metabolic regulator
    • Contraction of smooth muscle
    • Aggregation of platelets
    • Inflammation
arachidonic acid
Arachidonic Acid
  • Prostaglandins
    • Thrombocyclin
    • Prostacyclin
    • Leukotrenes
    • Neurotransmitters
    • Cychrome P450
  • Synthesized in liver
    • elongates linoleic acid (C18:2)
essential fatty acids1
Essential Fatty Acids
  • Since dietary poly-unsaturated fatty acids are hydrogenated to saturated fatty acids in the rumen by the microbes, how do ruminants meet their essential fatty acid requirement?
    • By-pass (rumen protected) lipids
    • Microbial lipid synthesis
      • Microbes don’t utilize lipids for energy, but they do synthesize them for their cell membranes
essential fatty acids2
Essential Fatty Acids
  • Deficiency of essential fatty acid intakes:
    • Growth retardation
    • Problems with reproduction
    • Skin lesions
    • Kidney and liver disorders
simple lipids
Simple Lipids
  • Neutral fats and oils
    • Monoacyl glycerols (monoglycerides)
    • Diacyl glycerols (diglycerides)
      • Diglycerides found in plant leaves
        • One fatty acid is replaced by a sugar (galactose)
    • Triacyl glycerols (triglycerides)
      • Triglycerides found in seeds and

animal adipose tissue

  • Triacyl glycerols (triglycerides)
    • Lipid storage form
      • Where in the body? Adipocytes!!
    • Most lipids consumed are triglycerides
triglycerides
Triglycerides
  • Most common structure in dietary lipids
  • Composed of one glycerol molecule and three fatty acids connected by an ester bond (bond between an alcohol and and organic acid)
    • Fatty acids may be same or mixed

Fatty Acid

Fatty Acid

Glycerol

Fatty Acid

triglyceride structure
Triglyceride Structure
  • Fatty acid composition of triglyceride varies according to function
    • Membrane lipids must be fluid at all temperatures
      • Contain more unsaturated fatty acids
    • Lipids in tissues subjected to cooling (e.g., hibernators or tissues in extremities)
      • Contain more unsaturated FAs
    • Butterfat (milk fat) is fairly fluid in spite of containing mostly saturated FAs
      • Why? Chain length!!
complex lipids phospholipids
Complex Lipids - Phospholipids
  • Two primary types:
    • Glycerophosphatides
      • Core structure is glycerol
      • Part of cell membranes, chylomicrons, lipoproteins
    • Sphingophosphatides
      • Core structure is sphingosine
      • Part of sphingomyelin
complex lipids phospholipids1
Complex Lipids - Phospholipids
  • Glycerophosphatides resemble triglyceride in structure except one of the fatty acids is replaced by a compound containing a phosphate group, or occasionally, nitrogen
  • Most prevalent is lecithin
phospholipids
Phospholipids
  • Significant use in feed industry as emulsifiers
    • Lipids form emulsion in water
  • Phospholipid sources:
    • Liver, egg yolk,
    • Soybeans, wheat germ
    • Peanuts
complex lipids glycolipids
Complex Lipids - Glycolipids
  • Carbohydrate component in structure
  • Cerebrosides & gangliosides
    • Medullary sheaths of nerves; white matter of brain
derived lipids
Derived Lipids
  • Prostaglandins
    • Synthesized from arachidonic acid
      • Several metabolic functions
  • Steroids
    • Cholesterol, ergosterol, bile acids
  • Terpenes
    • Made by plants
      • Carotenoids, xanthophylls
sterols
Sterols
  • Compounds with multi-ring structure
  • Insoluble in water
  • Present both in plant and animal foods
  • Major sterol is cholesterol
    • However, cholesterol is found only in animal products (manufactured in liver)
      • High content in organ meats and egg yolk
common sterol compounds
Common Sterol Compounds

Vitamin D3(cholecalciferol)

Cholesterol(a sterol)

Testosterone(a steroid hormone)

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