Chapter 2 - Lipids Flashcards
- How many kcal of energy per gram do lipids provide?
- What do triglycerides provide?
- What do phosphoglycerides, sphingolipids, and steroids have in common?
- What are steroid hormones critical for?
- What are the lipid soluble vitamins?
- What do dietary fats act as?
- As an energy source, lipids provide 9 kcal of energy per gram.
- Triglycerides provide energy storage in adipocytes
- They are all structural components of cell membranes
- Steroid hormones are critical intercellular messengers
- Lipid soluble vitamins are A, E, D, K
- Dietary fats act as a carrier of lipid soluble vitamins into cells of small intestine. (Provide shock absorption and insulation)
Fatty Acids
- What type of chain do fatty acids have?
- What is the range of common chains for fatty acids?
- What are the two types of Fatty Acids?
- What is a essential fatty acid?
- Long straight chain carboxylic acids. NO BRANCHING.
- Most common chains range from 10-20 carbons in length. (Usually even number of carbons in chain including carbonyl carbon)
- Saturated or Unsaturated. Usually no other functional groups.
- Any fatty acid that cannot be synthesized by the body.
Structure of Fatty Acids
- What is Stearic Acid?
- What is Oleic Acid?
- Stearic Acid is a typical SATURATED fatty acid with 18 carbons in the chain. (Straight chain of Carbons, no double bond)
- Oleic Acid is a typical UNSATURATED fatty acid with 18 carbons in the chain. (Bent chain of carbons with a double bond connection)
Saturated and Unsaturated Fatty Acids
- What type of fatty acids have double bonds?
- What configuration are double bonds in?
- How do double bonds affect melting point?
- How does increasing number of carbons affect melting point?
- Between Saturated and Unsaturated fatty acids, which has the higher melting point? Why?
- Only UNSATURATED fatty acids have double bonds. Typically one of more carbon-carbon double bonds in the chain, causing it to be bent.
- Double bond is normally in cis configuration (not conjugated). This does not allow fatty acids to pack as close together.
- Double bonds lower the melting temperature.
- Melting point increases with number of carbons.
- Melting point of saturated fatty acids is higher than an unsaturated with the same amount of carbons. Typically because saturated fatty acids are tightly packed together. Cis double bonds prevent good alignment of molecules in unsaturated fatty acids leading to poor packing.
Eicosanoids
- What is Linoleic Acid?
- What is Arachidonic Acid?
- What are Eicosanoids?
- Linoleic Acid is an essential fatty acid required to make arachidonic acid.
- Arachidonic Acid (which has 20 carbons) is the eicosanoid precursor.
- Eicosaoids are three groups structurally related compounds: Prostaglandins, Leukotrienes, and Thromboxanes
Prostaglandins
- What are prostaglandins? What do they exert?
- How are prostaglandins structured?
- What are prostaglandin names based on?
- How are Thromboxane and Leukotrienes structured?
- Prostaglandins are biological molecules that act like hormones in controlling several physiological functions. They exert their effects on cells that produce them and cells in the immediate vicinity.
- Synthesized from 20-carbon unsaturated fatty acids. These have cyclic compounds including a 5-carbon ring. Prostaglandins are made in most tissues.
- Based on ring substituents and number of side-chain double bonds.
- Thromboxanes have 6 carbon cyclic ring with two oxygens. Leukotrienes have no cyclic ring with attached OH.
Biological Processes Regulated by Eicosanoids
- How do Eicosanoids regulate…
1. Blood clotting
2. Inflammatory response
3. Reproductive system
4. Gastrointestinal tract
5. Kidney functioning
6. Respiration
- Thromboxane A2 stimulates construction of blood vessels and platelet aggregation. Prostacyclin dilates blood vessels and inhibits platelet aggregation.
- Prostaglandins mediate aspect of inflammatory response.
- Stimulation of smooth muscle by PGE2.
- Prostaglandins inhibit gastric secretion. Prostaglandins increase secretion of protective mucus. Inhibition of hormone sensitive lipases.
- Prostaglandins dilate renal blood vessels. Results in increased water and electrolyte excretion
- Leukotrienes promote the construction of bronchi. Prostaglandins promote bronchodilation.
Aspirin and Prostaglandins
1. How does Aspirin interact with prostaglandins?
- Aspirin inhibits prostaglandin synthesis by acetylating cyclooxygenase, an enzyme necessary for prostaglandin synthesis.
Glycerides
- What are glycerides? How are they created?
- Where does esterification occur?
- Where does a monoglyceride place a fatty acid chain?
- What do triglycerides serve as?
- What is the ionic charge and polarity of triglycerides?
- Where does a triglyceride place a fatty acid chain?
- Glycerides are lipid esters. They’re created by an alcohol group of glycerol forming an ester with a fatty acids.
- Esterification may occur at one, two, or all three alcohol positions producing : Monoglyceride, Diglyceride, and Triglyceride.
- Monoglyceride place fatty acid chains at one alcohol group of the glycerol.
- Triglycerides serve as energy storage in adipose cells.
- Triglycerides are neutral, nonionic, and nonpoloar
- Triglycerides place fatty acid chains at each alcohol group of the glycerol.
Fats and Oils
- What is the alternate name for triglyceride?
- What are fats a combination of?
- Where do Fats and Oils come from? What are their states at room temperature?
- Triacylglycerol
- Fats are a combination of glycerol and the fatty acids
- Fats come from animals, unless from fish, and are solid at room temperature. Oils mainly come from plants, and are liquid at room temperature.
Chemical Properties
NOTE: Triglycerides have typical ester and alkene chemical properties as they contain these two groups: Fatty Acid Reactions and Glyceride Reactions.
1. What two components consist of Fatty Acid Reactions (and what does each do)?
2. What two components consist of Glyceride Reactions (and what does each do)?
- Esterification: Reaction between the carbonyl of the fatty acid and the hydroxyl of an alcohol. Esterification reacts fatty acids with alcohols to form esters and water.
Hydrogenation: Saturates the double bonds (unsaturated fatty acids can be converted to saturated fatty acids). This is an addition reaction. Hydrogenation is used in the food industry.
- Hydrolysis: produces the fatty acids and glycerol, a reverse of formation. Hydrolysis reverses esterification. (Fatty Acids are produced from esters)
Saponification: Replace H with salt from a strong base (NaOH). Saponification is the base-catalyzed hydrolysis of an ester.
Products of this reaction are: an alcohol, an ionized carboxylic acid salt which is a soap.
– Soaps have a long uncharged hydrocarbon tail. Also have a negatively charged carboxylate group at end. Form micelles that dissolve oil and dirt.
“Hard water Problems”
- What does hard water contain high concentrations of?
- What happens when hard water is used with soaps?
- Hard water has high concentrations of Calcium and Magnesium.
- “Cations in the water form fatty acid salts which precipitate. This interferes with emulsifying action of the soap. Leaves a crusty scum on the surface of sink.
Phosphoglycerides
- What is a phosphoglyceride? What do they contain?
- How are phosphoglycerides created?
- What two domains do phosphoglycerides have? What is it responsible for in cells?
- What happens when phosphoglycerides are suspended in water?
- Any lipid containing phosphorus. Phosphoglycerides (phospacylglycerols) contain glycerol, fatty acid, and phosphoric acid with an amino alcohol.
- Phosphoglycerides are created by replacing an end fatty acid of a triglyceride with a phosphoric acid linked to an amino alcohol.
- Phosphoglycerides have hydrophobic and hydrophilic domains. Responsible for structural components of cell membranes.
- They spontaneously rearrange into ordered structures. Hydrophobic group to center. Hydrophilic group to water.
Types of Phosphoglycerides
- What domain are phospho-amino-alcohols? Where are they used in?
- What are the two types of Phosphoglycerides?
- Phospho-amino-alcohol is highly hydrophilic. They are used in cell membranes, emulsifying, and Michelle-forming agents in the blood.
- The phosphoglycerides made with choline are called Lecithin. Those made with either ethanolamine or serine are called Cephalins.
Nonglyceride Lipids
- What are sphingolipids based on? What 3 characteristics do they contain
- How are nonglycerides similar to phospholipids?
- How do sphingolipids affect cells?
- Sphingolipids are based on sphingosine. These have long chains, contains nitrogen, and has an alcohol.
- Like phospholipids, sphingolipids are amphipathic (Sphingolipids have one polar head group, two no polar fatty acid tail)
- Sphingolipids are structural components of cellular membranes