Question Lipids 3

Phospholipids, Essential Fatty Acids, LC-PUFA/Eicosanoids, Lipid peroxidation/Antioxidants Omega-3 fatty acids are A. A form of trans fatty acid B. Converted in the body to arachidonic acid C. Synthesized de novo in the liver and small intestine D. Found in certain PUFA-rich oils and coldwater fish E. B and D only

Functions of Phospholipids
Component of cell membrane Emulsifier
Bile acids Lecithins Improves food products

Emulsifiers

Found in wheat germ, peanuts, yolks, soy beans, organ meat

Fig. 02.29

Essential Fatty Acids

Polyunsaturated fatty acids that must be consumed in the diet since we cannot synthesize One key step missing cannot add a double bond closer than 9 carbons from omega end of the molecule Can add double bonds closer to alpha end of molecule Consume precursors and add double bonds closer to alpha end and make longer

Signs and Symptoms of Essential Fatty Acids Deficiency

Flaky, itchy skin Diarrhea Infections Retarded growth and wound healing

Essential Fatty Acid- Omega-6 (linoleic acid)

H H H H H H H H H H H H H O

H-C--C--C--C-- C--C =C--C--C=C--C--C--C--C--C--C--C--C-OH

H H H H H H H H H H H H H H H H H

omega end alpha end 1st double bond is located on the 6th carbon from the omega end

Essential Fatty Acid- Omega-3 (alphalinolenic acid)

H H H H H H H H H H H H H H H HH O
H-C--C--C=C--C--C =C--C--C=C--C--C--C--C--C--C--C--C-OH

H H

H H H H H H H

omega end alpha end 1st double bond is located on the 3rd carbon from the omega end

Essential Fatty Acids

Diet Sources Soybean, linseed, borage oils, others Omega-3 Series alpha-Linolenic acid 18:3n-3 Omega 6 Series Linoleic acid 18:2n-6 Diet Sources Most oils including soybean & safflower oils, chicken

Arachidonic Acid
AA serves as a precursor for a variety of lipidsoluble compounds that function as localized hormones. The compounds collectively known as eicosanoids Play a role in most physiological processes
Examples Blood flow regulation, body temperature regulation, the birthing process, immune function, signaling in the brain

Adding Carbons and double bonds occurs in liver and a few other tissues!! EPA 20:5n-3 (eicosapentaenoic acid

Fish and fish oils

Arachidonic Acid 20:4n-6

Meat, eggs, some fish

DHA 22:6 n-3 (docosahexaenoic acid)

Eicosanoids Overproduction
Although important to many normal physiological processes Eicosanoid overproduction by immune cells, etc. causes inflammation Inflammation is implicated in number of diseases arthritis, asthma, heart disease, even some cancers High amounts of AA in our cell membranes is proposed by some to contribute to greater production of eicosanoids more inflammation Higher dietary intake of omega-6 FA and less of omega-3 FA proposed to contribute to this Consuming more omega-3 fatty acids can have an anti-inflammatory effect

Fig. 17.23

EPA competes and decreases product formation

Health-related Effects
Arachidonic acid (Omega-6 )
Increases blood clotting Increases inflammatory responses
LNA

DHA, EPA (Omega-3)

Decrease blood clotting Reduce heart attack Decrease inflammation Other: Lower triglycerides, rheumatoid arthritis, behavioral disorders
LNA

Sources of Safe Fish

The toxins, mercury and PCBs, can accumulate in fish. Look for safe sources
http://www.epa.gov/waterscience/fishadvice/a dvice.html http://www.cfsan.fda.gov/~dms/admehg3.html http://www.mercuryaction.org/fish/

LC-PUFA Easily Oxidized

Arrangement of two double bonds with a C in between (1,4-pentadiene) susceptible to oxidation Leads to rancidity in food stinky fish Can cause oxidative stress in living organisms Prevented by antioxidants!!

Prevention of Rancidity
Hydrogenation decreases the # of double bonds Addition of antioxidants prevent oxidation
vitamin E, also vitamin C FDA approved synthetic antioxidants BHA and BHT Phytochemicals fruits (blueberries, strawberries, pomegranates), green tea, red wine, dark chocolate Hypertension

Many Foods Advertise Presence of Antioxidants

Dark Chocolate Comparison

Comparison of Chocolates Per Piece kcal total fat sat fat sugars Ghirardelli squares 55 4 3 4 Hershey's extra dark 53 4 2 4 Dove Rich Dark Chocolate 37 2 1 3 Hershey's Rich Dark Kisses 26 1 1 2