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Lipids
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Lipids are soluble in nonpolar organic compounds
They have a variety of structures and functions
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Fatty Acids Are Carboxylic Acid with Hydrocarbon Chains
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Polyunsaturated fatty acids have more than one
double bond The double bonds in naturally occurring fatty acids Have the cis configuration Double bonds in naturally occurring unsaturated Fatty acids are separated by one methylene group
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The three OH groups of glycerol are esterified with fatty acids
Triacylglycerols a triacylglycerol a fat or an oil glycerol fatty acids The three OH groups of glycerol are esterified with fatty acids
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Fats are triacylglycerols existing as solid or semisolid
state at room temperature
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Oils are liquid triacylglycerols
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Average composition of fatty acids %
Type Fat, Oil C14 C16 C18 Unsaturated Animal Fats Butter 8-15 25-29 9-12 44-58 Lard 1-2 25-30 6-12 56-68 Beef tallow 2-5 24-34 15-30 31-59 Vegetable Oils Olive 0-1 5-15 1-4 80-94 Peanut - 7-12 2-6 82-91 Corn 7-11 3-4 83-89 Soybean 6-10 2-4 84-91 Marine Oils Whale 5-10 10-20 65-83 Fish 6-8 10-25 1-3 64-83 C14 = myristic acid Unsaturated: Oleic (D1) C16 = palmitic acid Linoleic (D2) C18 = stearic acid Linolenic (D3)
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Phosphoacylglycerols
They are the major components of cell membranes The terminal OH group of glycerol is esterified with phosphoric acid
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The most common phosphoacylglycerols in
membranes have a second phosphate ester linkage Phosphoacylglycerols are classified as phospholipids
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Phosphoacylglycerols form membranes by arranging
themselves into a lipid bilayer Saturated fatty acids decrease membrane fluidity because their hydrocarbon chains can pack closely together. Unsaturated fatty acids have the opposite effect
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Sphingolipids They contain sphingosine instead of glycerol
They are also found in membranes They are the major lipid components in the myelin sheaths of nerve fiber
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Two of the Most Common Kinds of Sphingolipids
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Prostaglandins Prostaglandins are synthesized from arachidonic acid
They are responsible for regulating a variety of physiological responses Name in the format PGX, with X designating the functional groups of the five-membered ring postaglandin skeleton
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Naming Prostaglandins
PGE2 PGE1 PGF2a
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Terpenes Terpenes contain carbon atoms in multiples of five
They are made by joining together 5-carbon isoprene units Oxygen-containing terpenes are sometimes called terpenoids
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The Isoprene Rule
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Squalene, a triterpene, is a precursor of steroid
molecules
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Lycopene and b-carotene are tetraterpenes called
carotenoids
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Terpene Biosynthesis Formation of geranyl pyrophosphate
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Steroids All steroids contain a tetracyclic ring system
Many hormones are steroids Hormones are chemical messengers
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Methyl groups at C-10 and C-13 are called angular
The B, C, and D rings are trans fused Methyl groups at C-10 and C-13 are called angular methyl groups
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The A and B rings are also trans fused in most naturally
occurring steroids Substituents on the same side of the steroid ring system as the angular methyl groups are b-substituents Those on the opposite side of the plane of the ring system are a-substituents
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Classification of Steroids
1. Sterols 2. Bile Acids 3. Hormones Adrenocorticoid hormon Sex hormones 4. Steroid Glycosides 5. Steroid Alkaloids 6. Miscellaneous Steroids Toxines… etc…
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Cholesterol Is a Steroid
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