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Never eat these two foods before work
Brain serotonin is regulated by many important mechanisms, not the least of which is via free fatty acids.
However, some fatty acids do this far more than others.
Although this effect reliably occurs in humans and in all mammals tested, a “high-fat diet” is not necessarily serotonergic – although it can be.
A fatty acid’s ability to displace tryptophan is a direct function of the number of carbon atoms it has.
That means that the shorter-chained fatty acids have far less ability to do this than the longer ones.
And the really long ones, about twenty carbons or longer, start binding lipoproteins as well as serum albumin.
“…lipoproteins have a relatively high affinity for fatty acids that contain 20-24 carbon atoms, and they compete effectively with albumin for these very long-chain acids.”
And also, the very long-chained fatty acids can displace estradiol from sex steroid-binding globulin (SHBG) far more effectively than androgens.
And that makes some of those also estrogenic.
Although we do need some brain tryptophan, at least for melatonin synthesis…
Too much brain tryptophan can create enough serotonin to interfere with motivation and cognitive function.
By understanding which fatty acids liberate tryptophan the most (and how much), we can better choose the foods that are most suited to our anticipated mood and productivity level…
For example, peanuts or fish before serious work might be a bad idea…
Tryptophan is unique in that it is the only amino acid that significantly binds to serum albumin (a blood protein that we have throughout our bodies).
Yet scientists have known since the 1950s that fatty acids bind to albumin more strongly.
“Few proteins besides albumin can bind FFA, and none can bind them as tightly or in such large amounts.”
Since fatty acids have reliably been shown to displace tryptophan, they must be competing for the same spot.
It’s true that fatty acids cannot effectively displace most albumin-bound drugs and metabolites, such as thyroid hormone.
However, the fact that they reliably displace tryptophan suggests a purposeful function.
Fatty acids bind so strongly you could say they specifically displace tryptophan, thereby increasing brain uptake and serotonin synthesis.
This ability of certain fatty acids to increase serotonin in this manner seems to have evolved by design…
And this idea is supported by albumin-binding studies and the well-established association between serotonin and eating:
“Examination of individual nutrient intakes revealed that following serotonin, fat intake was more suppressed than either carbohydrate or protein intakes.”
For instance, fenfluramine was once a very popular weight-loss drug that acts by suppressing appetite.
It is a very serotonergic drug that acts to release brain serotonin (and thus prolactin) so reliably that it’s commonly used to estimate it.
Serotonin injections have been shown to decrease eating in animal studies – specifically the intake of fat.
It’s been shown that this effect also occurs upon the administration of procolipase, a natural peptide and coenzyme that works together with lipase to cleave triglycerides into free fatty acids.
Only free fatty acids effectively displace tryptophan from serum albumin, and not triglycerides or sterols.
“In this work, enterostatin has been shown to reduce specifically the consumption of a high-fat diet as opposed to a low-fat diet after central injection of Sprague-Dawley rats.”
(Sprague-Dawley rats are bred for use in medical and nutritional lab research.)
So brain serotonin can perhaps be seen as a physiological regulator of food intake…
…causing a relaxed and pleasant feeling after eating rich foods.
Alternatively, a reduction in serotonin caused by prolonged fasting or food scarcity can induce the motivation to seek more.
Serotonin actively inhibits dopamine and acetylcholine, the two neurotransmitters most associated with physical power and activity.
Yet in modern times, when even homeless people eat like kings (in comparison), a chronic over-activation of the serotonin system through eating is commonplace.
Serotonin inhibits acetylcholine release in the forebrain, thereby reducing the ability to think quickly and sharply.
It is also a universal dopamine antagonist, disabling its tonic inhibition of prolactin release in the pituitary – thereby causing its release.
Serotonin also releases growth hormone.
No doubt this facilitates a tall stature during the formative years…
But the fact that it’s also called “the death hormone” should indicate its role during middle age (Morley, 1999).
And, being similar to prolactin and binding the same receptor, it should be no surprise that growth hormone therapy also induces gynecomastia (man boobs).
Serotonin has many other untoward effects…
But fortunately, the differential binding data of fatty acids to albumin has been published.
This is all surprisingly consistent and suggests to us which fatty acids specifically displace tryptophan the most…
And also which fatty acids we can eat without that post-eating fatigue and dullness:
This binding effect has been demonstrated since the 1950s. That’s when we first had reports of albumin also binding tryptophan (McMenamy, 1958).
Multiple studies conducted in the 1970s then verified the universal nature of the effect, and while using refined methods.
Yet its early discovery highlights the potency of fatty acids in this regard.
(As a general rule, it is the strongest neurotransmitters, hormones, and effects that are the first discovered.)
In fact, fatty acids bind to albumin more strongly than even tryptophan…
Tryptophan has an association constant of only 2 × 103 at pH 7.95 (McMenamy, 1958).
On the other hand, the longer-chained fatty acids bind with magnitudes between 107 and 108.
Of these, it is invariably oleic acid that binds albumin the most strongly:
So fatty acids having either 16 or 18 carbons would liberate tryptophan the most…
Thereby increasing brain serotonin and melatonin…
With oleic acid beating out stearate for the #1 spot.
The short- and medium-chained fatty acids were tested in the 1970s all the way through to caproic acid (Ashbrook, 1972), which has six carbons… And they all have lower affinity constants (Ka ≈ 103).
Linoleic acid is still undoubtedly the worst fatty acid for other reasons…
But it would be expected to be a less effective tryptophan-releasing agent than oleic acid.
The omega-3 fatty acid of eighteen carbons (alpha-linolenic acid) was not tested in this study – or, ostensibly, in any other.
Alpha-linolenic acid is the precursor for DHA so it is arguably the only “essential” fatty acid (barring direct DHA consumption from fish).
Yet, despite the necessity of this in trace amounts, it would still be expected to be every bit as serotonergic as the other 18-carbon lipids.
The very long-chained membrane lipids EPA and DHA are recycled so efficiently that we only need trace amounts of them…
Actually we only need as much EPA and DHA as we can get from grass-fed beef and cheese…
(or perhaps from chia seeds used about as sparingly as poppy seeds are used on bagels).
Despite stearic acid having only about half the potency as oleic acid, even this is likely to be misleading in vivo.
(In vivo = in living lab subjects as opposed to on glass slides.)
Saturated fatty acids of approximately this length tend more to go towards the liver.
In the liver, they are assimilated into lipoproteins in triglyceride form.
On the other hand, unsaturated and monounsaturated fatty acids tend to immediately form chylomicrons.
Chylomicron is a small fat globule composed of protein and lipid (fat)…in the blood and lymphatic fluid…
They transport fat from the intestine to fat tissues and the liver.
So these fatty acids reach the plasma more rapidly.
On account of their bent shape and increased water-solubility, unsaturated fatty acids are more liable to form spontaneous micelles and chylomicrons.
(Micelle = an aggregate of molecules in a colloidal solution such as those formed by detergents.)
This gives unsaturated fatty acids a higher blood presence in free form – and a more rapid response than stearate.
Oleic acid is actually the most common fatty acid (and a monounsaturated one) consistently shown to be the most serotonergic.
It is also the one most expected to be serotonergic for another reason entirely:
Oleic acid is the precursor for oleamide.
Oleamide has been shown to potentiate serotonin receptors more potently than any other fatty acid amide…
It increases serotonin’s response fivefold – and in nanomolar concentrations.
By comparison, the amide of stearic acid (stearamide) has one third of the potency of oleamide on 5-HT1 and absolutely no effect on 5-HT2.
(5-HT1 and 5-HT2 are serotonin receptors.)
Olive oil could rightly be re-labeled “pro-serotonin oil” as it contains up to 83% oleic acid.
Olive oil is probably serotonergic enough to have been responsible for the fall of the Roman Empire…
…rather than cups made of lead, as has often been surmised.
The general trend in relative potency is: oleic > stearic > linoleic.
This was verified many times over in the early- and mid-1970s…
And enough science on that issue had accumulated to negate the necessity of more.
The more accurate studies – notably those using albumin stripped of pre-bound fatty acids – indicate that stearate has only 58% of the potency of oleate at binding site #1:
Stearate also has 56% of the potency at binding site #2, 66% of the potency at binding site #3, 27% at binding site #4, and 41% at binding site #5.
And, based on the normal physiological concentration of fatty acids and that of albumin, you’d think the high affinity to site would be mostly occupied anyway – on any diet.
This makes the lower affinity ones more relevant – because they’re more subject to change.
“The normal level of these fatty acids in humans is of the order of 5 × 10−4 mole per liter of plasma.”
There is also indication that this displacement occurs in vivo:
In one study, researchers fed a group of rats fed on bacon and corn and found they had more free tryptophan and brain serotonin than control rats (Hutson, 1976)…
In another study, a low-fat diet in baboons (more similar to us than rats) led to reduced serotonin activity.
So this is something to keep in mind when eating fatty acids from food – and especially those in pressed oils:
Fruit oils such as olive and palm have relatively high levels of free fatty acids.
That’s because lipase is released during the processing…
This contributes to increased lipolysis and free fatty acid content.
And as is often the case, coconut oil is exonerated from having the negative properties of many other oils…
That’s because it is a tropical nut having fatty acids too short to effectively compete with tryptophan.
Eighty-one percent of the fatty acids in coconuts are 14 carbons long or less.
Humans evolved in the tropics eating the short-chained fatty acids made by equatorial plants.
And those are relatively inert as a class.
Yeah, oleic acid doesn’t spontaneously peroxidize in water as most polyunsaturated fatty acids do… So it doesn’t contribute to lipofuscin.
But it certainly is the most serotonergic fatty acid.
“It thus appears that albumin is particularly well constructed to serve as a transport vehicle for fatty acids and that the albumin-fatty acid complex must be thought of as an entity with considerable biological significance.”
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- Curzon, G. "The effect of fatty acids on the binding of tryptophan to plasma protein." Nature (1973)
- Spector, Arthur. "Fatty acid binding to plasma albumin." Journal of lipid research (1975)
- Goodman, DeWitt. "The interaction of human serum albumin with long-chain fatty acid anions." Journal of the American Chemical Society (1958)
- Hutson, P. H. "Control of brain tryptophan concentration in rats on a high fat diet." Nature (1976)
- Muldoon, Matthew. "Effects of a low-fat diet on brain serotonergic responsivity in cynomolgus monkeys." Biological psychiatry (1992)
- Omega-3 Fatty Acids
- General Features of Fatty Acid Structure