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Cis Fat Information

An unsaturated fat is a fat or fatty acid in which there is at least one double bond within the fatty acid chain. A fat molecule is monounsaturated if it contains one double bond, and polyunsaturated if it contains more than one double bond. Where double bonds are formed, hydrogen atoms are eliminated. Thus, a saturated fat has no double bonds, has the maximum number of hydrogens bonded to the carbons, and therefore is "saturated" with hydrogen atoms. In cellular metabolism, unsaturated fat molecules contain somewhat less energy (i.e., fewer calories) than an equivalent amount of saturated fat. The greater the degree of unsaturation in a fatty acid (i.e., the more double bonds in the fatty acid) the more vulnerable it is to lipid peroxidation (rancidity). Antioxidants can protect unsaturated fat from lipid peroxidation.

Contents

Chemistry and nutrition

Amounts of fat types in selected foods

Double bonds may be in either a cis or a trans isomer, depending on the geometry of the double bond. In the cis conformation, hydrogen atoms are on the same side of the double bond, whereas, in the trans conformation, they are on opposite sides (see also Trans fat). Saturated fats are popular with manufacturers of processed foods because they are less vulnerable to rancidity and are, in general, more solid at room temperature than unsaturated fats. Unsaturated chains have a lower melting point, hence increasing fluidity of the cell membranes.

Although both monounsaturated and polyunsaturated fats can replace saturated fat in the diet, trans unsaturated fats should be avoided. Replacing saturated fats with unsaturated fats helps to lower levels of total cholesterol and LDL cholesterol in the blood. Trans unsaturated fats are particularly risky because the double bond stereochemistry allows the fat molecules to assume a linear conformation, which leads to efficient packing (i.e., plaque formation). The geometry of the cis double bond introduces a bend in the molecule, thereby precluding stable formations (see specific fatty acid links above for drawings that illustrate this). Natural sources of fatty acids (see above) are rich in the cis isomer.

Although polyunsaturated fats are protective against cardiac arrhythmias, a study of post-menopauseal women with a relatively low fat intake showed that polyunsaturated fat is positively associated with progression of coronary atherosclerosis, whereas monounsaturated fat is not.[1] This probably is an indication of the greater vulnerability of polyunsaturated fats to lipid peroxidation, against which vitamin E has been shown to be protective.[2]

Examples of unsaturated fats are palmitoleic acid, oleic acid, myristoleic acid, linoleic acid, and arachidonic acid. Foods containing unsaturated fats include avocado, nuts, and vegetable oils such as canola and olive oils. Meat products contain both saturated and unsaturated fats.

Although unsaturated fats are conventionally regarded as 'healthier' than saturated fats,[3] the United States Food and Drug Administration (FDA) recommendation stated that the amount of unsaturated fat consumed should not exceed 30% of one's daily caloric intake (or 67 grams given a 2000 Calorie diet). The new dietary guidelines have eliminated this recommendation at the request of the meat and dairy industries. Most foods contain both unsaturated and saturated fats. Marketers advertise only one or the other, depending on which one makes up the majority. Thus, various unsaturated fat vegetable oils, such as olive oils, also contain saturated fat.

Role of dietary fats in insulin resistance

Incidence of Insulin resistance is lowered with diets higher in monounsaturated fats (especially oleic acid), while the opposite is true for diets high in polyunsaturated fats (especially large amounts of arachidonic acid) as well as saturated fats (such as arachidic acid), these ratios can be indexed in the phospholipids of human skeletal muscle and in other issues as well. This relationship between dietary fats and insulin resistance is presumed secondary to the relationship between insulin resistance and inflammation, which is partially modulated by dietary fat ratios (Omega3/6/9) with both omega 3 and 9 thought to be anti-inflammatory, and omega 6 pro-inflammatory (as well as by numerous other dietary components, particularly polyphenols, and by exercise as well, with both of these anti-inflammatory). Although both pro-inflammatory and anti-inflammatory types of fat are biologically necessary, fat dietary ratios in most US diets are skewed towards Omega 6, with subsequent disinhibition of inflammation and potentiation of insulin resistance [4]

Membrane composition as a metabolic pacemaker

Cell membranes of mammals have a higher composition of polyunsaturated fat (DHA, omega-3 fatty acid) and a lower composition of monounsaturated fat than do reptiles. Higher polyunsaturated membrane content gives greater membrane fluidity (and functionality), commensurate with the higher metabolic rate of the warm-blooded species. In fish, however, increasingly cold environments lead to increasingly high cell membrane content of both monounsaturated and polyunsaturated fatty acids, to maintain greater membrane fluidity (and functionality) at the lower temperatures.[5]

Component in different foods

Fat composition in different foods (click at right to hide or show) · ·
Food Saturated Monounsaturated Polyunsaturated
As weight percent (%) of total fat
Cooking oils
Canola oil 7 59 29
Corn oil 13 24 59
Olive oil 13 74 8
Sunflower oil 10.3[6] 19.5[6] 65.7[6]
Soybean oil 15 24 58
Coconut oil 92 6 2
Dairy Products
Cheese,regular 64 29 3
Cheese,light 60 30 0
Milk, whole 62 28 4
Milk, 2% 62 30 0
Ice cream, gourmet 62 29 4
Ice cream, light 62 29 4
Meats
Beef 33 38 5
Ground sirloin 38 44 4
Pork chop 35 44 8
Ham 35 49 16
Chicken breast 29 34 21
Chicken 34 23 30
Turkey breast 30 20 30
Turkey drumstick 32 22 30
Fish,orange roughy 23 15 46
Salmon 28 33 28
Hot dog, beef 42 48 5
Hot dog, turkey 28 40 22
Burger, fast food 36 44 6
Cheeseburger, fast food 43 40 7
Breaded chicken sandwich 20 39 32
Grilled chicken sandwich 26 42 20
Sausage, Polish 37 46 11
Sausage, turkey 28 40 22
Pizza, sausage 41 32 20
Pizza, cheese 60 28 5
Nuts
Almonds dry roasted 9 65 21
Cashews dry roasted 20 59 17
Macadamia dry roasted 15 79 2
Peanuts dry roasted 14 50 31
Pecans dry roasted 8 62 25
Flaxseeds, ground 8 23 65
Sesame seeds 14 38 44
Soybeans 14 22 57
Sunflower seeds 11 19 66
Walnuts dry roasted 9 23 63
Sweets and baked goods
Candy, chocolate bar 59 33 3
Candy, fruit chews 14 44 38
Cookie, oatmeal raisin 22 47 27
Cookie, chocolate chip 35 42 18
Cake, yellow 60 25 10
Pastry, Danish 50 31 14
Fats added during cooking or at the table
Butter, stick 63 29 3
Butter, whipped 62 29 4
Margarine, stick 18 39 39
Margarine, tub 16 33 49
Margarine, light tub 19 46 33
Lard 39 45 11
Shortening 25 45 26
Chicken fat 30 45 21
Beef fat 41 43 3
Dressing, blue cheese 16 54 25
Dressing, light Italian 14 24 58
Other
Egg yolk fat 36[7] 44[7] 16[7]
Unless else specified in boxes, then reference is: [8]

References

  1. ^ Dariush Mozaffarian; Rimm, EB; Herrington, DM (1 November 2004). "Dietary fats, carbohydrate, and progression of coronary atherosclerosis in postmenopausal women". American Journal of Clinical Nutrition 80 (5): 1175–1184. PMC 1270002. PMID 15531663. http://www.ajcn.org/cgi/content/full/80/5/1175.
  2. ^ B Leibovitz; Hu, ML; Tappel, AL (1990). "Dietary supplements of vitamin E, beta-carotene, coenzyme Q10 and selenium protect tissues against lipid peroxidation in rat tissue slices". The Journal of Nutrition 120 (1): 97–104. PMID 2303916.
  3. ^ BBC Health, retrieved June 6, 2007.]
  4. ^ LH Storlien; Baur, LA; Kriketos, AD; Pan, DA; Cooney, GJ; Jenkins, AB; Calvert, GD; Campbell, LV (1996). "Dietary fats and insulin action". Diabetologica 39 (6): 621–631. doi:10.1007/BF00418533. PMID 8781757.
  5. ^ AJ Hulbert (2003). "Life, death and membrane bilayers". The Journal of Experimental Biology 206 (Pt 14): 2303–2311. doi:10.1242/jeb.00399. PMID 12796449. http://jeb.biologists.org/cgi/content/full/206/14/2303.
  6. ^ a b c .nutritiondata.com --> Oil, vegetable, sunflower Retrieved on September 27, 2010
  7. ^ a b c .nutritiondata.com --> Egg, yolk, raw, fresh Retrieved on August 24, 2009
  8. ^ Feinberg School > Nutrition > Nutrition Fact Sheet: Lipids Northwestern University. Retrieved on August 24, 2009

See also

· · Types of lipids
General Saturated fat · Unsaturated fat · Monounsaturated fat · Polyunsaturated fat
Geometry Trans fat · Omega-3 fatty acid · Omega-6 fatty acid · Omega-9 fatty acid
Fatty acids Lauric acid · Palmitic acid · Myristic acid · Stearic acid · Caprylic acid
Phospholipids Phosphatidylserine · Phosphatidylinositol · Phosphatidyl ethanolamine · Cardiolipin · Dipalmitoylphosphatidylcholine
Cholesterol/steroids Corticosteroids · Sex steroids
Sphingolipids Ceramide
Eicosanoids Arachidonic acid · Prostaglandin · Prostacyclin · Thromboxane · Leukotriene
biochemical : (, , ) · (/, , , , ) · / · / · /

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