Posted by Larry Hoover on June 1, 2006, at 7:24:26
In reply to Re: Evening primrose and sore/tender breasts? » Larry Hoover, posted by honeybee on May 31, 2006, at 17:14:19
> Wait, really? Why is it important that one take the GLA not every day? Sorry to derail into narcissistic pondering of my own program, but I've been taking EPO and Fish Oil every day, in about a 1:1 ratio (it's about a gram of each). It's rather annoying for me, too, because I want to be taking lots of fish oil, but it seems to make me nervous. I have no earthly idea why.
I discovered a mistake I made, so I needed to do it over again, anyway. I got messed up on the trivial or common names of these fatty acids (I really do understand how confusing it all sounds....trust me). I did not verify what I wrote, something I usually do. So, I apologize. I will re-write that older message, and let's just substitute this new one for the old one, shall we?
What do chemists mean when they say "trivial name" or "common name"? Aspirin is a common name for a particular substance, but so is acetyl-salicylic acid. Chemists developed a better naming system, called IUPAC. Aspirin (trivial) is called 2-(acetyloxy)benzoic acid (IUPAC). Maybe that's not a great example. How about the common-named selegeline? Its IUPAC name is N-methyl-1-phenyl-N-prop-2-ynyl-propan-2-amine. With a little patience, I could draw a structure for that, just from the IUPAC name. But I'm not going to give up talking about cholesterol, instead of 10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol. Nuh-uh.
Like I say, I got into trouble with the common names of these dang fatty acids. Linoleic acid is not the same thing as linolenic acid. Did you catch that? To make it worse, there are two versions (what chemists call isomers) of linolenic acid. Well, two common versions. There is a third one, too. There are alpha-, beta-, and gamma-linolenic acids. And, some vegetable oils have one or more of those, *and* linoleic acid, in them. It gets confusing. No sh*t, Sherlock.
With the IUPAC nomenclature, I wouldn't have made my mistake. But, to keep my words in accordance with the names you're likely to come across, I'll use both.
Here is the corrected version of what I said earlier:
Gamma-linolenic acid ((Z,Z,Z)-6,9,12-Octadecatrienoic Acid) and linoleic acid ((Z,Z)-9,12-Octadecadienoic Acid) are both omega-6 fats. Usually, where you find GLA, there's also tons of linoleic acid. GLA is just linoleic acid with one more unsaturated bond, but that one is in a different place than where the other 3-times unsaturated fatty acid, alpha-linolenic acid ((Z,Z,Z)-9,12,15-Octadecatrienoic Acid; omega-3, sometimes confusingly just called linolenic acid) has it.
Because they have these bonds in different positions, the stuff the body turns them into (the prostaglandins and leukotrienes and all that) means different things. The bond position reads like Braille to chemo-sensors that are exposed to them. The position of each bond really matters.
So, if GLA goes on to be elongated, but *not* desaturated, becoming the 20-carbon 3-unsaturated fatty acid called dihomogammalinolenic acid ((Z,Z,Z)-8,11,14-Eicosatrienoic Acid). Don't ask me what the hell that is supposed to mean (the dihomo part), but I don't think it has anything to do with sex. The *usual* 20-carbon omega-6 product is called arachidonic acid ((Z,Z,Z,Z)-5,8,11,14-Eicosatetraenoic Acid). It is what all that linoleic acid that is in vegetable oils turns into. We are eating about 30 times the amount of linoleic acid as ever before. It is not good for you. All that LA becomes a heap of arichidonic acid.
Arachidonic acid (AA) is converted to pro-inflammatory chemicals, such as the prostaglandin eicosanoids type 2 (PGE2).
Dihomogammalinolenic acid (DGLA) is converted into anti-inflammatory chemicals, such as PGE1.
Eicosapentaenoic acid (EPA, from fish oil) goes on to form anti-inflammatory chemicals such as PGE3.
By taking enough fish oil to compete with all that linoleic acid everybody is swamped with, you also inhibit the GLA going to the wrong stuff (AA). It all works good, if you take a source of GLA with your fish oil. Just take the GLA once in a while, not every day.
How does that work? Omega-3 fats have a higher affinity (than do omega-6s) for the enzyme known as delta-6 desaturase. It adds a double bond (desaturates) 18-carbon-long fatty acids. Because enzymes are stupid, it also saturates fatty acids that already have this desaturated spot. Fish oil (already desaturated right there) inhibits the enzyme, by binding in the active site and keeping GLA from binding to it. If GLA binds to that enzyme, it "reverts" from its special biochemical identity, and just goes on to form more of that arachidonic inflammatory stuff. So, by "blocking out" the GLA, it has only one option, to go on to become an anti-inflammatory prostaglandin of the PGE1 category. (That is simplified, but it's the best I can do without totally sounding like that other paper.)
If GLA supps didn't work for you, maybe this is why.
If you take GLA oils in fairly large doses, only once in a while, you minimize all the congestion around those essential enzymes that desaturate these polyunsaturated fats, while simultaneously maximizing the yield of beneficial prostaglandins.
Now, there are a few good sources of GLA. Borage oil is much higher in GLA than is evening primrose. The thing is, I think EPO has something extra, quite apart from the GLA, doing some good stuff. A phytoestrogen? A flavonoid? Something we haven't identified, but something good for PMS. Something good, apart from the GLA content, I mean.
Everybody has a unique tolerance for these oils that happen to be very rich in unusual polyunsaturated fatty acids. That goes for flax oil, fish oil (any marine oil, or algal oil), borage, evening primrose and so on. I urge people to take as much as they tolerate. It's all good, so long as you don't make yourself sick, in a novel way, by taking these oils.
I can't take anywhere near as much fish oil as some people report, but others can't manage nearly as much as I do. There is a vast range of tolerability. Do the experiment, by all means, but if the effect is unpleasant, back down until you find one that is. Then, just keep taking the stuff. Try a higher dose later on, to see if your tolerance has increased.
Lar
poster:Larry Hoover
thread:650131
URL: http://www.dr-bob.org/babble/alter/20060601/msgs/651371.html