logo course lecturer : jasmin Šutković 7 december 2015 organic chemistry – fall 2015 lecture 7...
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Course lecturer :
Jasmin Šutković
7 December 2015
Organic Chemistry – FALL 2015
Lecture 7Lipids
CHAPTER OUTLINE International University of Sarajevo
19.1 Introduction to Lipids19.2 Fatty Acids19.3 Waxes19.4 Triacylglycerols—Fats and Oils19.5 Hydrolysis of Triacylglycerols19.6 Phospholipids19.7 Cell Membranes19.8 FOCUS ON HEALTH & MEDICINE:Cholesterol, the Most ProminentSteroid19.9 Steroid Hormones19.10 FOCUS ON HEALTH & MEDICINE:Fat-Soluble Vitamins19.11 FOCUS ON HEALTH & MEDICINE:Prostaglandins and Leukotrienes
Book chapter 19
Introduction
CHAPTER 19 is the first of four chapters that deal with the chemistry of biomolecules, organic molecules found in biological systems.
Chapter 19 focuses on lipids, biomolecules that contain many carbon–carbon and carbon–hydrogen bonds, making them soluble in organic solvents and insoluble in water
Introduction
Lipids are biomolecules that are soluble in organic solvents and insoluble in water.
They are found in many varieties, so having many functions!
Common lipids include triacylglycerols in vegetable oils, cholesterol in egg yolk, and vitamin E in leafy greens.
The word lipid comes from the Greek word lipos for fat.
Lipids
Basic functions in the body Store and provide energy
– Fats provide 9 kcal per gram
Provide insulation Help manufacture steroids and bile salts Play a role in transporting fat-soluble nutrients
in the blood Used to manufacture major sex hormones Key to the structure of cell membranes
Fatty Acids
Building blocks for triglycerides and phospholipids
A chain of carbon and hydrogen atoms with a carboxyl group at the alpha end and a methyl group at the omega end
Figure 5.1
Fatty Acids
Higher ratio of carbon and hydrogen to oxygen than in carbohydrates and protein 9 kilocalories per gram of fat
20 different fatty acids with varied length, saturation, and shape
Fatty Acids Vary in Length
Short-chain fatty acids Two to four carbons Weak attraction Liquid at room temperature
Medium-chain fatty acids Six to ten carbons
Fatty Acids Vary in Length
Long-chain fatty acids
12 or more carbons Most common type of fatty acid in foods Strong attraction Solid at room temperature
Fatty Acids Vary in Saturation
Saturated All the carbons on the fatty acid are bound to
hydrogen Solid at room temperature Higher melting point
Fatty Acids Vary in Saturation
Unsaturated Some carbons on fatty acid form a double
bond with each other instead of binding to hydrogen• Monounsaturated fatty acids (MUFA)
– Has one double bond
• Polyunsaturated fatty acid (PUFA)– Has two or more double bonds
Liquid at room temperature Lower melting point
Saturated and Unsaturated Fatty Acids Help Shape Foods
Figure 5.3
Fatty Acids Differ in Double-Bond Location
The location of the first double bond in unsaturated fatty acids effect the omega-3 fatty acid and omega-6 fatty acid
Omega-3 fatty acid First double bond is between the third and
fourth carbon from the omega end Example: Alpha-linolenic acid
• One of the two essential fatty acids
Fatty Acids Differ in Double-Bond Location
Omega-6 fatty acid
First double bond is between the sixth and seventh carbon from the omega end
Example: Linoleic acid• One of the two essential fatty acids
The Omega Fatty Acids
Figure 5.4
Figure 5.5
Fatty Acids Vary in Shape
Unsaturated fatty acids form two different shapes
Portion of Figure 5.7
Triglycerides
Three fatty acids connected to a glycerol backbone
Caution:High levels in the blood
are a risk factor for
heart disease
Triglycerides
Most common lipid in both foods and the body Make up about 95% of lipids found in foods Functions
Add texture Makes meats tender Preserves freshness Stores as adipose tissue
for energy
Hydrophilic on one end; hydrophobic on the other Make up the phospholipid bilayer in the cell membrane Synthesized by the liver
Phospholipids
Portion of Figure 5.8
Phospholipids’ Role in Cell Membranes
Figure 5.9
Sterols
More complex than phospholipids or triglycerides Four connecting rings of carbon and hydrogen
Do not provide energy Cholesterol is the best known sterol
Found in every cell in the body Helps with numerous body processes
Phytosterols – major plant sterols
Figure 5.11
Quick Review
Figure 5.12
Quick Review
Triglycerides Found in the body Stored in the adipose tissue Major source of energy
Phospholipids An important part of cell membrane structure Lecithin
• Important to cell membrane
• Used as a food emulsifier
Sterols Do not contain fatty acids Do not provide energy
What Happens to the Lipids You Eat?
Lipids from foods Fat, phospholipids, and sterols
Digested to Free fatty acids, glycerol, and monoglycerides
With the aid of the enzyme lipase
Figure 5.13
Figure 5.13
Figure 5.13
Most Fat Is Digested and Absorbed in the Small Intestine
Lipoproteins Transport Fat Through the Lymph and Blood
Lipoproteins (transporter proteins) Chylomicrons Very low-density lipoproteins (VLDLs) Low-density lipoproteins (LDLs) High-density lipoproteins (HDLs)
Lipoproteins Transport Fat Through the Lymph and Blood
VLDLs, LDLs, and HDLs Globular molecule with a lipid center surrounded
by a plasma membrane Density determines function More protein, higher density
Very low-density lipoproteins (VLDLs) Become LDLs
LDLs: “bad” cholesterol HDLs: “good” cholesterol HDL and LDL levels can be used to determine the
health of arteries
The Roles of VLDL, LDL, and HDL Lipoproteins
Figure 5.18
Uses of Fat and Cholesterol
Source of energy Form body structures Regulate metabolism Enhance absorption of fat-soluble vitamins Provide insulation to help regulate body
temperature Cushion major organs
Fat Is Used as Energy
Fat Provides concentrated source of kilocalories
• 9 kilocalories per gram
Readily available when the body needs energy Body’s main source of energy throughout the
day
Fat Is Used as Energy
Fat Body has an unlimited ability to store excess
energy as fat in adipocytes• Fat cells have the capacity to enlarge as much as
1,000 times their original size• Body has the ability to produce additional fat cells
Fat Is Used as Energy and Helps Absorb Lipid Compounds
Preferred source of energy for the heart, liver, and muscles Cannot sustain life alone Needs glucose
Only glycerol can be used for gluconeogenesis
Several essential nutrients require dietary fat for absorption 20 grams per day are needed to stimulate chylomicrons that
transport fat-soluble vitamins
Fat Helps Insulate and Protect
Fat in subcutaneous tissue Insulates body Maintains body temperature
Fat protects bones and vital organs from trauma Too much fat eliminates the protective benefit
Cholesterol Is Used to Make Bile, Hormones, and Vitamin D
Cholesterol
A structural part of the cell membrane A precursor to vitamin D A precursor to bile acid Precursor for sex hormones such as estrogen and
testosterone
How Much Fat Do We Need Each Day?
Overall intake of fat in the U.S. is higher than it should be
Acceptable Macronutrient Distribution (AMDR) recommendation 20–35% of daily kilocalories should come from
fat
For heart health Consume no more than 10% of total
kilocalories from saturated fat Limit trans fats to < 1%
Essential Fatty Acid Recommendations
Adequate Intake (AI) for the essential fatty acids
Alpha-linolenic acid• Men 1.6 grams/d• Women 1.1 grams/d
Linoleic acid• Men 17 grams/d• Women 12 grams/d
*Currently Americans only consume about 0.1–0.2 grams/d of EPA and DHA
Best Food Sources of Fat
Figure 5.20
Sources of unsaturated fats
Food Sources of Omega-3 Fatty Acids
Figure 5.21
Where’s the Saturated Fat in Foods?
Figure 5.22
• Accumulate in the arteries
Fat and Cholest
erol
• Blood flow is impeded
Arteries narrow
• Not enough oxygen to the heart
• CHEST PAIN
Decrease oxygen
and nutrients
What Is Heart Disease and What Factors Increase Risk?
Cardiovascular disease is the number-one killer of adults in the world…
Atherosclerosis
Figure 5.24
For a healthy life do….
For optimal long-term health a diet should include a proper balance of all nutrients including fat
There are different types of lipids, some essential and others not required from foods
Goal Consume mostly unsaturated fats Limit amount of saturated and trans fats
A plant-based diet plentiful in whole grains, fruits, and vegetables, with some low-fat dairy and lean meats, poultry, fish, and vegetable oil will be high in fiber and lower in saturated fats, trans fats, and dietary cholesterol
Types of lipids
Lipids can be categorized as hydrolyzable or nonhydrolyzable.
Two types of fatty acids :
Saturated fatty acids have no double bonds in their long hydrocarbon chains.
Unsaturated fatty acids have one or more double bonds in their long hydrocarbon chains. Generally, double bonds in naturally occurring fatty acids are cis.
WAXES
Waxes are the simplest hydrolyzable lipids.
Waxes are esters (RCOOR') formed from a fatty acid (RCOOH) and a high molecular weight alcohol (R'OH).
Because of their long nonpolar carbon chains, waxes are very hydrophobic.
They form a protective coating on the feathers of birds to make them water repellent, and on leaves to prevent water evaporation.
Lanolin is a wax thatcoats the wool fibers of sheep.
Beeswax, a complex mixture of over 200 different compounds, contains the wax myricyl palmitate as its major component
TRIACYLGLYCEROLS—FATS AND OILS
Animal fats and vegetable oils, the most abundant lipids, are composed of triacylglycerols
Triacylglycerols, or triglycerides, are triesters formed from glycerol and three molecules of fatty acids.
PHOSPHOLIPIDS
Phospholipids are lipids that contain a phosphorus atom. Two common types of phospholipids are phosphoacylglycerols
and sphingomyelins. Both classes are found almost exclusively in the cell membranes of
plants and animals .
Phosphoacylglycerols
Phosphoacylglycerols (or phosphoglycerides) are the second most abundant type of lipid.
They form the principal lipid component of most cell membranes.
SPHINGOMYELINS
Sphingomyelins, the second major class of phospholipids, differ in two important ways from the triacylglycerols and the phosphoacylglycerols.
1. Sphingomyelins do not contain a glycerol backbone. Instead, sphingomyelins are derived from sphingosine.
2. Sphingomyelins do not contain an ester. Instead, their single fatty acid is bonded to the carbon backbone by an amide bond.
Cholesterol – most abudant steroid
Steroids are lipids whose carbon skeletons contain three six-membered rings and one five membered ring.
Fat soluble vitamins
The fat-soluble vitamins are lipids.
The four fat-soluble vitamins—A, D, E, and K—are found in fruits and vegetables, fi sh, liver, and dairy products. Although fat-soluble vitamins must be obtained from the diet, they do not have to be ingested every day.
Excess vitamins are stored in adipose cells, and then used when needed.
Table 19.5 summarizes the dietary sources and recommended daily intake of the fatsoluble vitamins.
Few topics for the coming projects…
Saturates and unsaturated fats in our food Biofuels Cell membrane structure Transport across the cell membrane Cholesterol and Lipoproteins Steroid hormones Asthma – steroids and leukotriens?
Short guidelines…
Power point presentation 4% 8 to 15 slides
Written Paper 4% 10 pages (double space: Introduction, main
body and conclusion, don’t forget reference and citations)
Answering of my and your colleagues questions 2%
Presentation week: 4 i 6th January 2016
Readings
Chapter 19 – pages : 569 -610
14th Dec.2014 Quiz II :Only lectures 6, 7 and 8 !
Read the book and dont forget to start to think about your projects- select a topic by 21th December or I will find it for You…