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BIO462 Biochemistry

Lipid (1)
Lipid (1)

- The Different Classes of Lipids. - Structure and Chemical Properties.

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Lecture outline
Lecture outline

1. The Definition of a Lipid 2. The Chemical Natures of the Lipid Types 3. Biological Membranes

Lecture outcome
Lecture outcome

Upon completion of this session, students should be able to:

i.

define what are lipids.

ii.

describe the chemical natures of the lipid types.

i.e. different classes of lipids, structure and chemical properties.

iii.

understand structure of lipids as biological membranes.

What is a Lipid

Lipids:
Lipids:
  • a heterogeneous class of naturally occurring organic compounds classified together on the basis of common solubility properties:-

    • insoluble in water,

    • but soluble in aprotic organic solvents (i.e. diethyl ether, chloroform, methylene chloride, and acetone)

  • Amphipathic in nature.

  • Lipids include:

    • I. Open Chain forms

    eg. A fatty acid OH O
    eg. A fatty acid
    OH
    O

    (polar head groups and long nonpolar tails)

    Fatty acids, Triacylglycerols, Sphingolipids, Phosphoacylglycerols, Glycolipids,

    Lipid-soluble vitamins,

    Prostaglandins, Leukotrienes, and Thromboxanes

    II.

    Cyclic forms (fused-ring compounds, based on the steroid ring skeleton)

    Cholesterol, Steroid hormones, and Bile acids

    D B C A
    D
    B
    C
    A

    Lipids have a variety of biological

    functions:

    • Structuring cell membranes.

      • The cell membrane constitutes a barrier for the cell and controls the flow of material in and out of the cell.

    • Energy storage.

      • Triglycerides are an efficient form of energy storage that can be mobilized when fuel is needed.

    • Transmission of information in cells (signal transduction).

      • Lipid hormones, like steroids and eicosanoids, also mediate communication between cells.

    • Cellular metabolism.

      • The fat-soluble vitamins A, D, E, and K are required for

    metabolism, usually as coenzymes.

    The basic classes of lipids

    • i. Fatty acids, which are a group of carboxylic acids (organic acids with a terminal carboxyl group, -COOH) that can be used as fuel molecules and serve as components of many other classes of lipids.

    ii.

    Glycerides (or glycerolipids) are lipids with a glycerol backbone; they include monoglycerides, diglycerides, and

    triglycerides, as well as the phosphoglycerides (or

    glycerophospholipids) found in biological membranes.

    iii.

    Nonglycerides, which have a non-glycerol backbone,

    includes waxes, sphingolipids, sterol lipids (such as cholesterol and the steroid hormones), and prenol lipids

    (such as terpenoids), and polyketides.

    iv.

    More complex lipid derivatives, such as sugar-linked lipids (glycolipids) and protein-linked lipids.

    (I) (II) (III) (IV) http://www.biologyexams4u.com/2012/10/classification-of-lipids.html#.Vy4qbNR96t9
    (I)
    (II)
    (III)
    (IV)
    http://www.biologyexams4u.com/2012/10/classification-of-lipids.html#.Vy4qbNR96t9

    An alternative classification system has been proposed (Fahy, et. al., 2005),

    Lipids are divided into the following groups:

    (1) fatty acyls,

    (2) glycerolipids, (3) glycerophospholipids, (4) sphingolipids,

    (5) sterol lipids, (6) prenol lipids, (7) saccharolipids, and

    (8) polyketides.

    Fahy, E., S. Subramaniam, H. A. Brown, C. K. Glass, A. H. Merrill, Jr., R. C. Murphy, C. R. H. Raetz, D.

    W. Russell, Y. Seyama, W. Shaw, T. Shimizu, F. Spener, G. van Meer, M. S. VanNieuwenhze, S. H.

    White, J. L. Witztum, and E. A. Dennis. 2005. A comprehensive classification system for lipids. J. Lipid Res 46:839-862.

    (I) Fatty Acids  Fatty acid: an unbranched-chain carboxylic acid, most commonly of 12 - 20
    (I) Fatty Acids
    Fatty acid: an unbranched-chain carboxylic acid, most commonly of
    12 - 20 carbons, derived from hydrolysis of animal fats, vegetable
    oils, or phosphodiacylglycerols of biological membranes
    In the shorthand notation for fatty acids
    • the number of carbons and the number of double bonds in the chain are shown by two numbers, separated by a colon

    (I) Fatty Acids  Fatty acid: an unbranched-chain carboxylic acid, most commonly of 12 - 20

    Fatty Acids

    Length of fatty acid plays a role in its chemical character

    • Usually contain even numbers of carbons (can contain odd,

    depending on how they are biosynthesized)

    • FA that contain C=C, are unsaturated: If contain only C-C bonds, they are saturated

    Fatty Acids Length of fatty acid plays a role in its chemical character • Usually contain

    Fatty Acids

    • In most unsaturated fatty acids, the cis isomer predominates; the trans isomer is rare

    • Unsaturated fatty acids have lower melting points than their saturated counterparts; the greater the degree of unsaturation, the lower the melting point

    Fatty Acids  In most unsaturated fatty acids, the cis isomer predominates; the trans isomer is
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    (I)
    (II)
    (III)
    (IV)
    http://www.biologyexams4u.com/2012/10/classification-of-lipids.html#.Vy4qbNR96t9

    (II) Triacylglycerols

    

    Triacylglycerol (triglyceride): an ester of glycerol with three fatty acids

    • natural soaps are prepared by boiling triglycerides (animal fats or vegetable oils) with NaOH, in a reaction called saponification (Latin, sapo, soap)

    Soaps

    • Soaps form water-insoluble salts when used in water

    containing Ca(II), Mg(II), and Fe(III) ions (hard water)

    Soaps  Soaps form water-insoluble salts when used in water containing Ca(II), Mg(II), and Fe(III) ions
    Soaps  Soaps form water-insoluble salts when used in water containing Ca(II), Mg(II), and Fe(III) ions
    • Reactions with acids/bases as catalysts

    • Salts formed by saponification

    Soaps  Soaps form water-insoluble salts when used in water containing Ca(II), Mg(II), and Fe(III) ions

    Phosphoacylglycerols (Phospholipids)

     When one alcohol group of glycerol is esterified by a phosphoric acid rather than by
    When one alcohol group of glycerol is esterified by a
    phosphoric acid rather than by a carboxylic acid,
    phosphatidic acid produced
    Phosphoacylglycerols (phosphoglycerides) are the
    second most abundant group of naturally occurring

    lipids, and they are found in plant and animal

    membranes

    Phosphoacylglycerols (Phospholipids)  When one alcohol group of glycerol is esterified by a phosphoric acid rather

    Phosphoacylglycerols (Phospholipids)

    Phosphoacylglycerols (Phospholipids)

    (III) Nonglycerides Lipids

    • have a non-glycerol backbone,

    • includes

    i.

    waxes,

    ii.

    sphingolipids,

    iii.

    sterol lipids (such as cholesterol and the steroid

    iv.

    hormones), prenol lipids (such as terpenoids),

    Waxes

    • A complex mixture of esters of long-chain carboxylic acids and alcohols

    • Found as protective coatings for leaves of many plants

    • Animals skin and fur are wax-coated

    • Highly insoluble

    • An example of a wax.

    Oleoyl alcohol is esterified to stearic acid in this case

    from a long-chain alcohol

    from a fatty acid (found in carnauba wax)
    from a fatty acid
    (found in carnauba wax)

    Sphingolipids

    • Contain sphingosine, a long-chain amino alcohol sphingosine

    • Sphingosine is an 18-carbon amino alcohol

    • Found in plants and animals

    • Abundant in nervous system

    • Bares structural similarity to phospholipids

    Sphingolipids  Contain sphingosine , a long-chain amino alcohol sphingosine  Sphingosine is an 18-carbon amino
    Sphingolipids Ceramides • The simplest compounds of this class. • Consist of one fatty acid linked

    Sphingolipids

    Ceramides

    The simplest compounds of this class.

    Consist of one fatty acid linked to the amino group of sphingosine by amide bond Glycosphingolipids are ceramides with one or more sugars in beta-glycosidic linkage at the 1-hydroxyl group

    Spingomyelins

    Similar structure to phosphoacylglycerol

    Amphipathic

    Occur in cell membranes in the nervous system

    Glycolipids

    
    Glycolipids  Glycolipid: a compound in which a carbohydrate is bound to an -OH of the

    Glycolipid: a compound in which a carbohydrate is

    bound to an -OH of the lipid

    In most cases, sugar is

    either glucose or galactose

    • many glycolipids are derived from ceramides

    Glycolipids with complex carbohydrate moiety that

    contains more than 3

    sugars are known as

    gangliosides

    Glycolipids  Glycolipid: a compound in which a carbohydrate is bound to an -OH of the

    Important Gangliosides

    Steroids

    • A group of lipids that have fused-ring structure of 3 six- membered rings, and 1 five-membered ring.

    • The steroid of most interest in our discussion of biological membranes is cholesterol.

      • the most common steroid in animals and precursor for all other steroids in animals

    • Precursor of other steroids and vitamin D3

    • Play role in the development of atherosclerosis lipid deposit blocks blood vessels.

    • Steroid hormones serve many functions in animals - including salt balance, metabolic function and sexual function

    Structures of

    some steroids

    (1) The fused-ring structure of steroids. (2) Cholesterol. (3) Some steroid sex hormones.

    Structures of some steroids (1) The fused-ring structure of steroids. (2) Cholesterol. (3) Some steroid sex

    Lipoproteins

    Biological Membranes

    • Every cell has a cell membrane (plasma membrane)

    • Eukaryotic cells also have membrane-enclosed organelles (nuclei, mitochondria…etc)

    • Molecular basis of membrane structure is in lipid component(s):

      • polar head groups are in contact with the aqueous environment

      • nonpolar tails are buried within the bilayer

      • the major force driving the formation of lipid bilayers is

    hydrophobic interaction

    • the arrangement of hydrocarbon tails in the interior can be rigid (if rich in saturated fatty acids) or fluid (if rich in unsaturated fatty acids)

    Lipid Bilayers

    • The polar surface of the bilayer contains charged groups

    • The hydrophobic tails lie in the

    interior of the bilayer

    Lipid Bilayers  The polar surface of the bilayer contains charged groups  The hydrophobic tails