LIPIDS

 Structurally dissimilar (heterogenous) biomolecules

 Common feature: Insoluble in water and soluble in nonpolar solvents
 
 Classification of lipids
 
Hydrolyzable Lipids Non-hydrolyzable Lipids
Simple (Storage 1. Ster
 Triglyc ols
erides 2. Fat
 Waxes soluble vitamins
3. Terp
enoids
4. Eicos
anoids
Complex (Membrane  
 Phosph
olipids
 Sphing
olipids
Membrane lipids
 Bilayer is asymmetric
 Noncovalent interactions = free movement of proteins and lipids
 
 Fatty Acids
1. Short to long chain carboxylic acids (≥4C)

2. May be saturated or unsaturated

Saturated FA
 Contains single bonds only
 Good stacking =increased IMFA =increased MP
 Solids at room temp
Unsaturated FA
 Contains one or more double bonds
 Less stacking because of kinks = decreased MP
Some common Saturated Fatty Acid
No. of Systematic name Common name
Carbons
6 Hexanoic acid Caproic acid
8 Octanoic acid Caprylic acid
10 Decanoic acid Capric acid
12 Dodecanoic acid Lauric acid
14 Tetradecanoic acid Myristic acid
16 Hexadecanoic acid Palmitic acid
18 Octadecanoic acid Stearic acid
20 Eicosanoic acid Arachidic acid
Nomenclature
a. Simplified (delta) nomenclature - chain length:#double bonds (location, A)
b. Omega (w) nomenclature — position of double bonds relative to the last carbon (farthest from
COOH)

 
Some common unsaturated fatty acids
No. of Systematic Name Common Name
Carbons
  10-Undecenoic acid Undecyclenic acid
  9-Hexadecenoic acid Palmitoleic acid
  9-Octadecenoic acid Oleic acid
  9,12- Octadecadienoic acid Linoleic acid
  9,12,15-Octadecatrienoic acid Linolenic acid
  5,8,11,14- Eicosatetraenoic acid Arachidonic acid
  5,8,11,14,17- Eicosapentenoic acid (EPA Timnodonic acid
  4,7,10,13,16,19- Docosahexaenoic acid(DHA Cervonic acid

 Hydrolyzable Lipids
 
Phospholipids
o Similar in structure with TAGs but with one FA replaced with phosphate
 o Parent compound: PHOSPHATIDIC ACID
o Example of Phospholipids
 

 
Name Polar Accessory Head Use
Group
Phosphatidic acid -H (no accessory group  Parent
compound
Phosphatidylcholine Choline  Aka:Lecithin
 Major
component of CM
Phosphatidylethanolamine Ethanolamine  Aka: Cephalin
 Minor role in
blood clotting
Phosphatidylserine Serine  Precursor of
p.choline and p.ethanolamine
 Role in
apoptosis
Diphosphatidylgylycerol Phosphatidyl glycerol  Aka:
Cardiolipin
 Component of
motochondrial membrane and
nontreponemal tests
Phosphatidylinositol-4,5- Inositol-4,5-bisPO4  Involved in G-
bisPO4 protein signalling
 
 Sphingolipids and Glycolipids
o Composed of the backbone sphingosine (an aminoalcohol) bonded to a in an/amid linkage
o Parent compound: CERAMIDE
 

 
Name Polar Accessory Head Group Use
Ceramide -H (None Parent compund
Shingomyelin Phosphatidylcholine Sphingophospholipid in myelin sheath
Cerebroside Monosaccharide (Glc or Gal Neutral Glycolipids
Globoside Oligosaccharide Component of CM of neural tissues
Ganglioside Complex oligosaccharide Charged acidic glycolipid
(N-acetylneuraminic or Sialic acid Also found in nervous tissues
 
Waxes
o Esters of long-chain (C14 to C36) saturated and unsaturated fatty acids with long-chain (C16 to
C30) alcohols
o Uses: water repellent and energy stores in some animals
EXAMPLES:
o Carnauba wax
o Beeswax
o Spermaceti
o Jojoba oil
o Lanolin

o Non-hydrolyzable Lipids
 
Sterols
o Structurally contain the cyclopentanoperhydrophenanthrene (CPPP) nucleus
o Uses: regulates the fluidity of cell membrane, precursor of bile acids andchormones
 EXAM P LES:
o Cholesterol (animals)
o Phytosterol (plants) — e.g. stigmasterol, beta sitosterol
o Ergosterol (fungi)
 
Terpenoids / Isoprenoids
o Composed of 5 carbon called ISOPRENE UNITS
 

 
 
No. of Name Examples
Carbons
10 (2 isop. Monoterpene Most volatile oils (eg: geraniol, citral, mentho
15 (3 isop. Sesquiterpene Artemisin
20 (4 isop Diterpene Zingiberol, paclitaxel
30 (6 isop Triterpene Squalene
40 (8 isop. Tetraterpene Retinol, lycopene
 
Fat-soluble Vitamins
 
Vitamin Name Uses
A Retinoids Important in vision and epithelial cell growth
D Cholecalciferol Enhances Ca2 absorption of intestines and mobilizes bine mineral
E Tocopherol Antioxidant
K Phytonadione Blood clotting
     
 
Vitamin A
Beta-carotene — pro vitamin A
Retinoids:
o Retinal (active)
o Retinol (transport form)
o Retinoic acid (cell growth and differentiation)
Deficiency:
o Xerophthalmia
o Nyctalopia
Vitamin D
Vitamin D
o Vitamin D3(Cholecalclferoi)
o 25-OH Vitamin D (Caicifedlol)
o 1,25-diOH Vitamin D (Caicltriol) - most active
Deficiency:
o Rickets
o Osteomalacia
Vitamin E
Tocopherols —biologic antioxidants
Terminates free-radical peroxidation
Deficiency
o In lab animals: scaly skin, muscle wasting and sterility
o In humans: not established
Vitamin K
Vitamin K
o Vitamin K1 — green leafy vegetables
o Vitamin K2 - formed by GI flora
o Vitamin K3 - synthetic
Deficiency
o Blood clotting disorders
o In neonates: Hemorrhagic disease of the newborn
 
Eicosanoids
o Formed from C20 polyunsaturated FAs
 
 o Qualitative Tests
Test Use Reagent Visible Results
Acrolein For glycerol Heating the sample Acrid/burnt odor of acrolein
(propenal
Ammonium For phosphate Ammonium molybdate Yellow ppt
molydate
Osmic acid For fats and fixed Osmium tetroxide Black ppt
oils
Salkowski For cholesterol H2SO4 Red color
Lieberman- For cholesterol H2SO4 acetic Emerald green
Burchard anhydride