Eicosanoids

Yesterday's post on my favorite fats had prompted some questions about eicosanoids. I recommend you take a look at this chemistry post as well before we begin.

Eicosanoids are chemical messengers made from fats that contain 20 carbons. This means they are made from three fatty acids.

Eicosapentaenoic acid - This is EPA. This is one of the omega-3 fatty acids found in fish oil and cod liver oil. It has 5 double bonds

Arachidonic acid - This is an omega-6 fatty acid found in meats. It has 4 double bonds.

Dihomo-gamma-linolenic acid- This i an omega-6 acid with 3 double bonds. I am admittedly not particularly familiar with it.


The eicosanoids are one of the most complex systems in the human body. They are important in inflammation, immunity, and the central nervous system. Eicosanoids derived from the omega-6 fatty acids are generally inflammatory. Those derived from the omega-3 fatty acids are generally anti-inflammatory or have no affect on inflammation. The amounts of these eicosanoids in the body are greatly dependent on the amount of fats that they are derived from. Eat lots of omega-6 fatty acids and you'll have lots of omega-6 derived eicosanoids. This will contribute to diseases like high blood pressure, high triglycerides, and imflammatory diseases like arthritis.

There are four families of eicosanoids. They are:
-prostaglandins
-prostacyclins
-leukotrienes
-thromboxanes

So how are these eicosanoids made? They are made by the careful enzymatic oxidation of fats. Anyone who's read Nourishing traditions know that unsaturated fats should not be used for cooking because they will oxidize and can cause cellular damage. This still holds true, and the oxidation of these fats is very carefully controlled by enzymes and kept away from the nuclei of cells. Anti-oxidants can help limit the production of some of the pro-inflammatory eicosanoids There is evidence that the eicosanoid pathways evolved from the bodies attempt to detoxify oxidized fats.

The prostaglandins, prostacyclins, and thromboxanes are known collectively as the prostanoids. They ae responsible for the swelling, redness, pain, and heat associated with imflammation.

The synthesis of the omega-3 and omega-6 acids into eicosanoids involves parallel pathways, The same enzymes act on both. It is the difference in the fatty acid itself that makes the often parallel eicosanoids.

One of the most well known eicosanoid enzymes is also one of the most often used. Cycloocygenase, known more commonly ax COX, is responsible for making the prostanoids. There are three types of the COX enzyme; COX-1, COX-2, and COX-3.
Its the COX-2 enzymes that are most responsible for imflammatory omega-6 derived eicosanoids. One of the COX-1 enzyme's major functions is making eicosanoids to help blood clot.

Traditional NSAIDs such as aspirin inhibit all COX enzymes. This is one reason aspirin has a blood thinning effect as well as relieving pain. It is not selective and inhibits everything.

There are some newer NSAIDs available by prescription that inhibit only the COX-2 enzyme. You have probably already figured out that these are referred to as "COX-2 inhibitors." The problem with COX-2 inhibitors is that they have all sots of cardiovascular side ffects, and increase the risk of all sorts of heart problems. Vioxx was one of these COX-2 inhibitors. It was so dangerous it was taken off the market. Many of Pfizer's COX-2 inhibitors got on the market largely due to fraudulent research. You can read up more on this if you want. My advice is to stay far away from COX-2 inhibitors. These drug's names almost always end in "-coxib." i.e Merck's etoricoxib (Arcoxia), Pfizer’s celecoxib (Celebrex) and valdecoxib (Bextra)

The leukotrienes are the other family of eicosanoids, which more people are hearing about. Their action is implicated in inflammatory diseases such as asthma and rheumatoid arthritis, as well as asthma and allergic rhinitis. There is a drug on the market now called Singulair that is used for asthma and allergies. It works by blocking these leukotrienes.

Remember that when we talk about these broad categories of eicosanoids that its usually the ones derived from the omega-6 fats that are pro-inflammatory, and that the omega-3 ones have no effect on imflammation and may even be anti-inflammatory.

"Well thanks for all the tehnical info Zeke," you're saying, "but so what?"

These eicosanoids are one of the main reasons it is so important to pay attention to your essential fatty acid balance. If you want inflammatory eicosanoids eat more omega-6's, which isn't hard since they're everywhere these days. Soybean oils is almost all omega-6, and sunflower oil is ALL omega-6. Remember that next time you go to grab a bag of Lay's. Even though they are now trans fat free, they are now made with pure sunflower oil. Carbs and omega-6 fatty acids. It's a heart attack in a bag. The craptacular salt they use doesn't help either.

Now this isn't to say that you should cut omega-6 oils completely out of your diet. They are still ESSENTIAL fatty acids. The key is ratio's.

The proper ration of omega-6 to omega three is believed to be somewhere between 4:1 and 1:1. Studies have shown that the Eskimos ate extremely high fat diets with rations of 1:30 without ill effects. It seems that an excess of omega-6 is bad, but that if the ration is swung the other way with high omega-3's there is no observed ill effect. The typical American eats a ration of 10:1 up to a 30:1 ratio. This is the exact opposite of what the Eskimos ate/eat and we have health as terrible as their's isn't. For your reference, here is a list of some common oils and their fatty acid ratio's shown as the ratio of omega-6 to omega-3

flax 1:3
canola 2:1
olive 3–13:1 (be aware that olive oil can vary from a great ratio to a bad radio. Always read the label.)
walnut 4:1
soybean 7:1
corn oil 46:1
sunflower 1:0 (no omega-3)
cottonseed 1:0 (almost no omega−3)
peanut 1:0 (no omega−3)
grapeseed oil 1:0 (almost no omega−3)

For more reading I suggest the works of Udo Erasmus and Mary G. Enig. Also the wikipedia article on eicosanoids is very good.

This article is part of Fight Back Fridays at Food Renegade. Check it out! Its a great blog.

Flax Seed Cereal and Wheat Germ Oil for A-Fib

The organic chemistry lesson is going to become a weekly thing, so look out for that on Mondays. (I want to do it everyday, but I can't spend three hours on one blog post every day)




Today I'm here to talk about flax seeds and cold pressed wheat germ oil.

I'm 23 years old. I'm a young man about to get his bachelor's degree in environmental chemistry. I have atrial fibrillation.

Its a heart condition where the heart muscle's electrical timing gets thrown off and the chambers don't pump in quite the right order. I've only had one major attack, but for about a year before that, and ever since I would occasionally feel one heartbeat every now and then that wasn't right, then my heart would beat normally.

As anyone who has had A-fib can probably tell you, when you have it, it feels like your heart is trying to do a cartwheel inside your chest. It usually isn't painful like a heart attack, but It can be. I've never experienced pain from it.

I took my a-fib attack as a sign from God to stop eating so much crap. I'd known about NT and traditional diets for awhile but was too lazy to do it. I now had a little motivation.

Sine starting a traditional diet I've lost some weight. (I'm 'morbidly obese' which is why I had a-fib in the first place). It has been slow though because I still eat too many carbs. (I love me some rice.)

Well I haven't had an a-fib incident in quite some time, not even a single beat out of step. Its all thanks to proper fat and vitamin consumption. Before this, even though I wasn't in a-fib, I could feel my heart beating in my chest, like I just had a tiny tiny bit of wannabe a-fib. I haven't even had that.

To me flax seeds are a miracle food. About ten minutes after my first bowl of flax cereal my heart was beating perfectly normal. I couldn't even feel it. For a few second I was afraid that it had stopped! I forgot that this was normal and you aren't supposed to feel your heartbeat. I had been taking fish oil for somet ime, and it helped, but nothing knocked out the a-fib like flax.

Flax is high in mediumish chain Omega-3 (N-3) fatty acids. In fact it's oil is mostly Alpha-linoleic acid. It turns out that omega-3 oils fight inflammation, and a-fib is an inflammatory condition.

Omega-3 oils fight inflammation because of eicosanoids. Eicosanoids are chemical messengers made from fats. Omega-3 oils and omega-6 oils both go through the same chemical pathways to become these eicodanoids. Every omega-3 eicosanoid has a corresponding omega-6 eicosanoid. The difference is in their effect on the body. Omega-6 eicosanoids CAUSE inflammation. When you get bit by a mosquito and have a nistamine reaction, these omega-6 eicosanoids are released and cause the bite to swell and get warn and to turn red. Omega-3 eicosanoids have the opposite effects. They reduce inflammation and swelling, and restore things to normal.

You may have seen commercials fo a drug called Singulair that blocks 'leukotrienes.' Leukotrienes are one type of eicosanoid. The omega-6 leukotrienes are largely responsible for the actual effects of the histamine reaction. Instead of popping pills for your allergies, try restoring your fatty acid balance. I know it has helped mine. To do this you can take fish oil or cod liver oil (extra vitamins in cod liver oil), and flax seed oil. I use ground flax seeds and warm water to make an extremely low carb breakfast cereal. It can be a bit slimy due to all the soluble fiber, but I find it quite tasty with a little butter and salt.

The other thing I've added to my diet that has helped is cold pressed wheat germ oil. This is one of natures best sources of vitamin E. Cold pressed palm oil is also high in vitamin E.

Wheat germ oil contains not only all the tocopherols in the proper balance, but the tocotrienols as well, which are almost always forgotten about. I forget who did the study, but many of the early studies that showed vitamin E was good for your heart were done with wheat germ oil. Many vitamin E studies today are done with synthetic vitamin E and even the unnatural and harmful esterified form of vitamin E. Yuck!

I take a spoonful of cold pressed wheat germ oil with my fish oil every day. It tastes strongly of wheat germ, so I was it down with water pretty quick, but its a small price to pay to prevent heart failure, don't you think?