Chapter 23 Lipids Created By Prof. Gary F. Porter, Ph.D. Copyright © 2014 by John Wiley & Sons, Inc. All rights reserved.

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Chapter 23 Lipids Created By Prof. Gary F. Porter, Ph.D. Copyright © 2014 by John Wiley & Sons, Inc. All rights reserved.

Table of Contents 1.IntroductionIntroduction 2.Fatty Acids and TriacylglycerolsFatty Acids and Triacylglycerols 3.Terpenes and TerpenoidsTerpenes and Terpenoids 4.SteroidsSteroids 5.ProstaglandinsProstaglandins 6.Phospholipids and Cell MembranesPhospholipids and Cell Membranes 7.WaxesWaxes © 2014 by John Wiley & Sons, Inc. All rights reserved.

1. Introduction © 2014 by John Wiley & Sons, Inc. All rights reserved. Definition: Lipids are compounds extracted from living organisms using non-polar solvents. So, lipids include a variety of structural types.

Fatty Acids – are long chain (>14 carbons) carboxylic acids, – have an even number of carbons, – may be saturated (no double bonds), and – may be unsaturated (contain double bonds). All double bonds are cis. Double bonds have weakened intermolecular forces because of a molecular bend. They have lower melting points. 2. Fatty Acids © 2014 by John Wiley & Sons, Inc. All rights reserved.

Triacylglycerol is a triester (a fat or oil) – made of 3 Fatty Acids & Glycerol. – produce monomeric units by hydrolysis. 2. Triacylglycerols © 2014 by John Wiley & Sons, Inc. All rights reserved.

2A. Hydrogenation of Triacylglycerols – Increases M.P. 2. Fatty Acids and Triacylglycerols © 2014 by John Wiley & Sons, Inc. All rights reserved.

2B. Biological Functions of Triacylglycerols include: – long term storage of energy, and – helping us survive starvation conditions. Fat and health – Saturated fats are linked to heart disease. – Too much fat in the diet is a health concern. Physical properties – Fat is a solid. (saturated) – Oil is a liquid. (unsaturated) 2. Fatty Acids and Triacylglycerols © 2014 by John Wiley & Sons, Inc. All rights reserved.

2C. Saponification of Triacylglycerol – Involves the basic hydrolysis of a triacylglycerol. 2. Fatty Acids and Triacylglycerols © 2014 by John Wiley & Sons, Inc. All rights reserved.

Detergent is the anion of a strong acid. keeps multivalent metals solvated. prevents soap scum. 2. Fatty Acids and Triacylglycerols © 2014 by John Wiley & Sons, Inc. All rights reserved.

2F. Reactions of the Carboxyl Group of Fatty Acids 2. Fatty Acids and Triacylglycerols © 2014 by John Wiley & Sons, Inc. All rights reserved.

2E. Reactions of the Alkenyl Chain Group of Unsaturated Fatty Acids 2. Fatty Acids and Triacylglycerols © 2014 by John Wiley & Sons, Inc. All rights reserved.

The monomeric unit – Is isoprene. – Has 5 carbons. Larger molecules from isoprene: 3. Terpenes and Terpenoids © 2014 by John Wiley & Sons, Inc. All rights reserved.

See how to find the terpene monomers in the polymers below. 3. Terpenes and Terpenoids © 2014 by John Wiley & Sons, Inc. All rights reserved.

Practice Problem 23.2 (a)Show the isoprene units in each of the following terpenes. (b)Classify each as a monoterpene, diterpene, sesquiterpene, and so on. 3. Terpenes and Terpenoids © 2014 by John Wiley & Sons, Inc. All rights reserved.

Carotenes – contain two diterpenes Vitamin A - is a precursor of a carotene, and - is a diterpene. 3. Terpenes and Terpenoids © 2014 by John Wiley & Sons, Inc. All rights reserved.

3A. Natural Rubber Vulcanization creates disulfide linkages between chains. 3. Terpenes and Terpenoids © 2014 by John Wiley & Sons, Inc. All rights reserved.

4A. Structure and Systematic Nomenclature Cyclopentophenanthrenes α substitution – Group is trans to C-18 methyl β substitution – Group is cis to C-18 methyl 4. Steroids © 2014 by John Wiley & Sons, Inc. All rights reserved.

4. Steroids © 2014 by John Wiley & Sons, Inc. All rights reserved. 4B. Cholesterol (C27) - Parent compound Derivatives made from cholesterol: Bile acids (C24) Adrenocortical hormones & progesterone (C21) Male sex hormones (C19) Female sex hormones (C18)

4B. Cholesterol Dietary Cholesterol is a mixture of lipids, one of which is cholesterol. HDL – High Density Lipoproteins – travel from tissues to liver, and – are an indicator of good health. LDL – Low Density Lipoproteins – travel from liver to tissues, and – are an indicator of poor health. 4. Steroids © 2014 by John Wiley & Sons, Inc. All rights reserved.

4C. Sex Hormones Estrogens – female hormone Androgens – male hormone Progestins – pregnancy hormone – Suppress ovulation. 4. Steroids © 2014 by John Wiley & Sons, Inc. All rights reserved.

4D. Adrenocortical Hormones – are 28 different Hormones, – are produced in the adrenal cortex located in adrenal glands found on top of the kidneys, and – drive numerous biological regulation activities including the inflammatory response. 4. Steroids © 2014 by John Wiley & Sons, Inc. All rights reserved.

4E.D Vitamins Sunlight is needed to produce Vitamin D 3. VitaminD 3 is needed for health and facilitates the process by which calcium is absorbed to allow proper bone growth. 4. Steroids © 2014 by John Wiley & Sons, Inc. All rights reserved.

Structure: – Includes twenty carbons. – Has a five membered ring. Made from Arachidonic Acid: – Eicosatetraenoic acid 5. Prostaglandins © 2014 by John Wiley & Sons, Inc. All rights reserved.

Phospholipids are structural components of membranes. Phospholipids are most commonly: – Glycerol based or – Sphingosine based. Phosphatidic acid is the parent of glycerol based phospholipids. Ceramide is the parent of sphingosine based phospholipids. 6. Phospholipids and Cell Membranes © 2014 by John Wiley & Sons, Inc. All rights reserved.

Phosphatidic acid has three components: – Glycerol, – 2 Fatty Acids, and – Phosphate. Phosphatides have an additional group bonded to the phosphate. 6. Phospholipids and Cell Membranes h © 2014 by John Wiley & Sons, Inc. All rights reserved.

6A. There are four common phosphatides. Phosphatidyl: ethanolamine, choline, serine and inositol. 6. Phospholipids and Cell Membranes © 2014 by John Wiley & Sons, Inc. All rights reserved.

6. Phospholipids and Cell Membranes © 2014 by John Wiley & Sons, Inc. All rights reserved. 6A. Phosphatide - Is a soap-like molecule.

6B. Derivatives of Sphingosine ( Parent Molecule) – Sphingomyelin is a component of myelin found in nerve cell membranes (sheaths). – Cerebroside is a brain cell membrane component. 6. Phospholipids and Cell Membranes © 2014 by John Wiley & Sons, Inc. All rights reserved.

are esters of long chain fatty acids, act as a water resistant coat, and are found on skin, fur, and feathers. 7. Waxes © 2014 by John Wiley & Sons, Inc. All rights reserved.

Ch  END OF CHAPTER 23 