chapter 12. part i. lipids - personal.tcu.edupersonal.tcu.edu/yryu/50133/lipids.pdfcarboxylic acids...
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Chapter 12.
Part I. Lipids
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Functions of lipids
• Building blocks of membranes• Energy storage• Hormones• Mediators of signal transduction
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Lipid classification
• Fatty acids• Triacylglycerols• Glycerophospholipids• Sphingolipids• Steroids• Other lipids
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Fatty acidsCarboxylic acids with long-chain hydrocarbon side groups
• Saturated• Unsaturated - double bonds are usually in the cis configuration;
30° bend in the hydrocarbon chain
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18:0 18:1 (∆9) 18:2 (∆9,12) 18:3 (∆9,12,15)
ω-3 fatty acidω-6 fatty acid
ω1
2
34
56
1ω
23
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Structural features of storage and membrane lipids
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Triacylglycerols (Triglycerides)• Triesters of glycerol and fatty acids• Fats or oils• Energy storage and thermal insulation
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Trans fats
Strong contributing factor of coronary heart disease
(↑LDL, ↓HDL)
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Major food sources for trans fat for American adults
FDA “Trans Fatty Acids in Nutrition Labeling, Nutrient Content Claims, and Health Claims” (July 11, 2003)
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Adipocytes (Fat cells)• Synthesis and storage of fats• Secretion of protein hormones in related to the glucose
homeostasis (adiponectin, leptin, resistin etc)
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Glycerophospholipids
• Amphiphilic• Major lipid
components of biological membranes
• Signal transduction
tail
head
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Phospholipids are hydrolyzed by phospholipases
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Sphingolipids
Sphingosine
• Glycolipids• Abundant in brain and nerve membranes• Cell-cell recognition
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Steroids
CholesterolSteroid core structure
Cholesteryl esters
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Functions of steroids
• Component of membranes– cholesterol
• Bile acids (helping digestion of dietary fats)– Cholic acid and glycocholic acid
• Hormones– estrogens– androgens– progestins– glucocorticoids– mineralocorticoids
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Cholesterol
• Membrane component• Precursor of steroid
hormones• Precursor of bile salts
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Steroid hormones
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Bile acids
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Phytosterols
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Vitamin D
Inactive
Enzymatic hydroxylation
This active form promotes the intestinal absorption of dietary Ca2+, thereby increases serum [Ca2+] and subsequently the deposition of Ca2+ in bones and teeth
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Other fat-soluble vitamins
(Photoreceptor in the eye)(Electron transfer in mitochondria)
(Blood clotting)
(Antioxidant of membrane proteins and lipids)
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Isoprenoids (=terpenoids)
(citrus fruits) (vitamin A precursor)
(plant hormone)
(precursor of plant and animal steroids)
(antioxidant)
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Eicosanoids
• Derived from arachidonic acid (C20)• Prostaglandins, thromboxanes and
Leukotrienes• Regulate pain, fever, blood pressure,
blood coagulation, and reproduction• Produced and act locally at low
concentrations (10-12 to 10-14M)• Short lifetimes (seconds to minutes)
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(Cyclooxygenase, COX)
Arachidonate pathway
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COX Enzymes
• COX-1– Constitutive, expressed in most tissues– Cell maintenance and housekeeping– Synthesis of prostaglandins responsible for
protection of the stomach lining• COX-2
– Induced by inflammatory stimuli such as injury or disease
– Synthesis of prostaglandins responsible for pain and inflammation
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Non-steroidal anti-inflammatory drugs (NSAIDs)
Selective inhibitor of Cox-2
Inhibitors of Cox-1 and Cox-2
(Tylenol)
(Advil, Motrin)
Little anti-inflammatory effect