Fish, dark chocolate, and red wine.

Fish oil fatty acids: EPA & DHA.

I’ve read that EPA tends to show slightly better results in outcomes related to mood, whereas DHA tends to be slightly better for cognition.  Not mutually exclusive; probably a lot of overlap.  This meta-analysis by Martins showed EPA fared better than DHA for depressive symptoms (2009); another one here, stressing the high %EPA relative to %DHA necessary for improvements (Sublette et al., 2011).  Whereas the reverse is true for certain cognitive outcomes in this study by Sinn and colleagues (2012).  Very few studies test EPA vs. DHA directly, and their effects on metabolism are relatively similar.  They’re the ball bearings of fatty acids.epa dpa dha

But then there’s this: pre-treatment of hepatocytes with EPA enhances lipid peroxidation and alcohol-induced oxidative stress (Aliche-Djoudi et al., 2011):EPA EtOH

This isn’t *too* surprising because, after all, EPA is more unsaturated than linoleate and linoleate does no favors for the livers of alcohol-fed rodents.  Saturated fats, on the other hand, provide robust protection (eg, Zhong et al., 2013 [cocoa butter & MCTs]).

However, pre-treatment of hepatocytes with DHA had the opposite effect; nearly completely suppressed alcohol-induced damage (Aliche-Djoudi et al., 2013):DHA EtOH

DHA is more unsaturated than EPA.  If the mechanism was related to the degree of unsaturation or peroxidizability, then DHA should’ve fared worse than EPA.  In both cases, the authors chalked it up to lipid rafts.  This could be considered good news for fish lovers, as DHA is naturally higher than EPA in salmon, for example, and to a lesser degree in sardines and oysters.fish

Despite all the differences between EPA & DHA mentioned above, I found this discrepancy odd.  However, one human epi study showed that DHA enhanced the protective effect of EPA in NAFLD (Oya et al., 2010), which, worded another way could indirectly support these findings.

Perhaps this is due to DHA’s peroxisomal bias whereas EPA favors mitochondria? (eg, Willumsen et al., 1993 & Madsen et al., 1999).  DHA is also more likely to end up in phospholipids than EPA; this may impact membrane fluidity… but as to why there’s such a sharp contrast on alcohol-fed rat livers… I don’t know.

to review:
Coconut oil (eg, You et al., 2008 & Lieber et al., 2008).
Dark chocolate to saturate your lipid membranes.
Salmon/DHA? DHA can be retroconverted to EPA in vivo, but how this would play out in the above scenario is unknown (to me). The one human study suggests a net positive effect.
Bonus: Brussels sprouts & asparagus (Ronis et al., 2005).

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  • George

    This paper is interesting because it suggests EPA benefits are mediated by DPA. DHA will also convert to DPA.
    http://www.ncbi.nlm.nih.gov/pubmed/22586114

    Depending how long DHA pretreatment was, it could have protected liver by lowering hepatocyte fat content. Activate PPAR-alpha, remove excess fats, decrease risk of peroxidation?

    • http://www.caloriesproper.com/ William Lagakos

      The pretreatments were rather long, 18 hours (most likely based on convenience), so anything’s possible!

      Also, I’m surprised French’s recommendation doesn’t included saturated fats…
      Cocoa butter and coconut oil work.
      PUFAs don’t. except one, DHA?

      • George

        No, he is recommending, if that’s not too strong a word, fats that are 3% PUFA so tallow, butter, coconut, cocoa are included, olive oil excluded.
        DHA works before drinking.
        There’s a bit about n-3 from phosphatdylcholine here: http://onlinelibrary.wiley.com/doi/10.1002/hep.510280401/pdf

      • johnnyv

        What about choline? Definitely recommend getting a decent amount of it if you are binging on alcohol.
        Also choline is needed to handle the saturated fat that will protect your liver from the alcohol binging.

        • http://www.caloriesproper.com/ William Lagakos

          Most of the rodent diets include choline bitartrate. As for humans: liver, eggs, some green veggies… all good sources of choline.

      • Jack Kruse

        Your missing the key issue……your thinking about DHA reductively by itself and not where and how it acts with the other parts of the membrane. Where is DHA concentration the highest in humans? The synapse. Why. DHA unsaturated bond angles allow for a pi electron cloud. These electrons become very free to move and are excitable in membranes. What protects them in the synapse ? Proteins surrounded by reverse water micelles that iodine embedded in them that protect DHA from oxidation. The synapse is here DHA oxidation potential is highest, yet this is where DHA is highest. Seems crazy when you think about it biologically but it makes perfect sense when you understand the physics of how a cell is organized.

        • http://www.caloriesproper.com/ William Lagakos

          “The synapse is here DHA oxidation potential is highest, yet this is where DHA is highest.”
          That’s very interesting, but EPA isn’t all that different from DHA structurally… I was surprised to see such markedly different effects.

          • Jack Kruse

            Since pi electrons are on the neurons surface and the cortex is on top of the brain the interaction of the pi electrons with CSF and collagen in arachnoid surrounding the brain are where this happens. Photoelectric effect is what powers our brain mitochondria and the energy harvested there is transformed when it goes from mitochondria to the collagen water interface in the subdural space. In physics there are 4 possible fates
            Matter interacts with light in four different ways:
            Absorption – the energy in the photon is absorbed by the matter and turned into thermal energy. E.g., Your hand feels warm in front of a fire.
            Reflection – no energy is transferred and the photon “bounces” off in a new (and predictable) direction. E. g. Your bathroom mirror.
            Transmission – no energy is transferred and the photon passes through the matter unchanged.
            Emission – matter gives off light. It can be done in only two different ways, as we will see.
            These processes depends on both the material composition and the wavelength of the photon. The material in the human brain is the construction of the cell membranes (WHY DHA is here) of the neuron and the content of the CSF. These are the critical parts of a neuron. I remind you Bill electrons give all chemistry is specificity.

          • Jack Kruse

            The food we eat completely determines what kind of health we will have because of the way Mother Nature created us.
            Many people in the paleosphere call this area the mind/body connection, but I find this to be a misnomer. The mind is the sum total function of the central nervous system (CNS) and its endocrine secretion is called a thought. That secretion can directly up regulate DNA and RNA activity with gene expression and protein formation. This means that a thought has a tangible action. This ability is found in the biochemistry of the DHA molecule itself.
            Few people realize the possibility is that DHA in vivo plays a more direct role in neuronal signaling, in which some special properties conferred on the membrane by DHA chains exert an influence on membrane electrical phenomena (Bloom et al. 1999) This implies that the DHA molecule itself has some special electrical abilities and can exert quantum effects in vivo. The 6 double bonds in DHA allow for its electron cloud in the molecular structure of DHA to become a very special fatty acid with respect to unique properties. Humans exploit those advantages more than any other mammal on this planet. It has been put forth that some polarization of ?-electron clouds might occur in the DHA structure, and perhaps even be transmitted from one double bond to another, either within a given chain, or between neighboring chains in the membrane. This means that DHA has different properties in the lipid structures of the brain than it does when a researcher studies it in the lab. It implies these effects are lost when fish oil is in a pill form outside of its evolutionary package of shellfish. This is why supplementation falls far short of eating fish

          • Jack Kruse

            When DHA molecules are adjacent to each other in a tissue like the brain the ?-electron clouds actually are closer together in space than they are when the DHA molecule is alone by itself in a pill or in a liquid state. This unique ability allows for DHA in a membrane to be come its own receptor in a membrane to allow for amazing electrical abilities. This is why DHA is so special and has been conserved by evolution in the nervous system of all life forms and not replaced with the more common land based form of PUFA’s like DPA

          • Jack Kruse

            The molecular magic is so impressive, that Roger Penrose has shown how consciousness can be explained by the quantum effects of this one fatty acid. In this molecular arrangement it would allow for gamma coherence of the neural microtubules found in the brain’s substance. This chemistry explains the effects of anesthesia and of consciousness, which have not be well described anywhere else in the biologic sciences. It appears the brain is built upon a special fat that allows for quantum effects to happen routinely. These measurements have actually been made in vivo in NMR experiments and electron tunneling experiments. These tunneling of electrons is also found to happen in mitochondrial electron transport respiratory chains as well. Theseenergy effects get changed to different forms of energy as electrons are force down white matter tracts filled with microtubules where water and collagen have a special arrangement. Penrose and Hammeroff believe this is where conscious arises. I think it happens every where along the neuronal cytoarchitecture. This evidence that these things happen within nanoseconds in the cell membranes of neurons are found in vivo experiments done in medicine daily according to functional MRI data, and EEG strips in all of us that doctors order daily. These abilities are also unique to humans. It’s nothing short of amazing to think evolution can move that fast on a micro level but still not affect the phenotype of the organism in any great macro way. Another paradox of life revealed I guess done by DHA in vivo.

          • Jack Kruse

            We also know today, that epigenetic modifications usually involves activation of NF kappa beta at some point in the biochemical pathways of life. Therefore we must, consider inhibitors to NF kappa beta. We also now know that DHA can change macrophages from inflammatory ro antinflammatory signalers. Look up the M1 and M2 conversion of macrophages anywhere in the body. DHA is the trigger and no other vascular or brain PUFA is. We now know that DHA is one of those inhibitors of NF kappa beta when it is married to iodine. This implies a diet ( not any supplement) high in DHA not only is required for a complex nervous system but it also predicts excellent longevity because of its intranuclear effects on the main “911 controller” of the cytokine storms that cause inflammation and neolithic disease. These findings are nothing short of amazing, and help explain why brain DHA levels correspond directly to leptin levels and of mankind’s underlying hormone balance on labs.

          • Jack Kruse

            Now how does DHA link to temp? You mentioned fluidity yourself earlier. Maybe you are beginning to see why cold temperatures are critical in brain injuries. Cold = more O2 delivery because cold water (CSF) is more dense and sinks to the bottom of CSF where the neocortex is. What is on the neocortex? memebranes loaded with DHA.

          • Jack Kruse

            A word abou thow you and I differ on viewing temperature: Why is Temperature a Big Player in the Brain and our Environment?
            The higher the temperature, the faster the atoms/ molecules in the object are (T ~ v2), thus more energetic collisions occur.
            More energetic collisions cause more sudden accelerations/decelerations of the electrons in the matter (see why DHA would be in our surface neurons now?), thus light with shorter wavelength carries a higher energy. This is why” blue light” from any source at any time frame turns off the energy currents at darkness that control the brain circadian cycles for sleep. It is physics 101.
            What are these implications?
            1. Higher Temperature = faster atoms
            2. Faster atoms = more frequent and energetic collisions
            3. more frequent and energetic collisions = more sudden electron accelerations/decel
            4. more sudden electron accelerations/decel = higher photon energy
            5. Higher photon energy = bluer light (E=hc/?)
            Making sense to you now why DHA is so highly conserved for a mammal brain?
            Do not confuse “heat” and “temperature” as most biologists and chemists do! Temperature refers to the degree of motion of the particles in a material [i.e. the speed with which the particles move (T~kinetic energy~v2)]. Heat refers to the amount of energy stored in a body as motion among its particles and depends on density as well as temperature. Heat is infrared energy and water absorbs this type of energy ideally. Now you see why CSF surrounds the brain. It is the ultimate electric adaptor for all forms of electromagnetic spectrum of energies. These energies are delivered directly to the pi electron cloud of DHA to animate life and activate the white matter. We can see this activation with diffusion MRI. What is the first effect? The neuron swells and it causes a neuromechanical change in the DHA laden cell membrane.

          • Jack Kruse

            See Denis Le Bihan work on diffusion weighted MRI activation of neurons. http://www.meteoreservice.com/dlb.htm When this mecahnical change happens…………this stretches the arachnoid made of collagen which is embedded in all CSF surrounding the brain. Here electron current from water and DHA pi electron clouds become a new form energy. Think the second law of thermodynamics, and this photoelectrical energy becomes neuromechanical energy which is sent to all tissues with a collagen skeleton. This is why collagen is the number one protein in animals and why it is always found next to some fluid with water as its main component.

          • Jack Kruse

            The three main sources of energy in the universe funnels to three natural fundamental physical things: they are the photoelectric effect, water chemistry and the native electromagnetic forces. The key to understanding how life works in humans is understanding that these three factors come together to structure matter in a certain way allows life to act like a collective phenomena.
            In other words, the three laws of nature come together and begin to act in unison to do the things life is observed to do. It is where 1 + 1 = 4. This is why no one can fathom how DHA acts within the brain, nor how the brain does what it does based upon what is published in a biology textbook. That reason is simple: you need to think like a quantum physicist to understand how the brain does what it does. How a cell and tissue is organized is based upon physics not biology. A biologist could never fathom some of these mechanisms because it is not part of their educational domain. If it is not part of their “vernacular,” so they just ignore it or deride it. Well, have a look at photosynthesis. They did not expect that either.
            Physics has already proven beyond a shadow of a doubt these mechanisms exist in nature. Biology just has no clue they are at work under their noses. The problem for biologists is that the subatomic world has been experimentally proven to a far greater degree than anything printed in biology anywhere. Moreover, QED has been proven to be very accurate by being experimentally proven correct every time one tries it out. Biology can not claim the same record. QED has been shown to act everywhere in nature, while in biology, they continue to argue about metabolism of macronutrients for 100 years, and these arguments have gotten us more ill

          • http://www.caloriesproper.com/ William Lagakos

            GPR120 is probably involved here; KO mice don’t experience the anti-diabetic effects of fish oils, and their macrophages exhibit a robust M1 phenotype that is unaffected by DHA.

          • Jack Kruse

            PUFA omega 3’s are difficult to understand from PUFA 6 chemistry for many biochemists because how they work is based upon quantum principles in the CNS using their pi electron clouds with iodine and the water in CSF. GPR 120 has been shown to mediate the anti inflammatory and insulin sensitizing effects of O3 PUFA’s. The strict lack of GPR 120 actually reduces lipid metabolism and can lead to obesity or in some cases eating disorders via its effects on leptin and the nrf2 pathway. In the human neuro-immune system (MHC1) omega 3 PUFA’s are converted by macrophage’s to an intermediate compound called 13S and 14 S epoxy-maresin. Maresins are produced by macrophages from DHA and they exert potent pro-resolvin and tissue homeostatic actions on the MHC1 proteins. Here you see the link to immune activation. These alter their action. Resolvins are compounds that are made by the human body from the omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). They are produced by the COX-2 pathway especially in the presence of aspirin. This happens to be why aspirin is helpful in heart disease. No other reason. The aspirin effect is greater in men than women because men absorb more EMF than women to do electrify there DNA and protein water micelles. Experimental evidence indicates that resolvins reduce cellular inflammation by inhibiting the production and transportation of inflammatory cells and chemicals to the sites of inflammation. Maresin’s promote the conversion of macrophages from M1 phenotype to M2 phenotype that specifically does not stimulate inflammation in the human body.

            1. http://www.ncbi.nlm.nih.gov/pubmed/21601924

            2. http://www.ncbi.nlm.nih.gov/pubmed/23504711

          • Jack Kruse

            where not here……i was typing slower than my thoughts.

        • George

          Seaweeds are high in iodide and bromide because these are antioxidants – http://prospect.rsc.org/blogs/cw/2008/05/08/seaweed-use-iodine-as-an-antioxidant/

  • maria

    Hi. I’m new to this blog and I don’t know how I didn’t found it before it’s one of the best regarding low carb diets/keto – Valuable information. Thank you for that.

    This is a little bit off topic but I’m 20 years old and I have Hashimoto’s since I was 14. What’s your take on using coconut oil everyday? Is it ok or only temporary purposes?
    Sorry if there’s any mistake, I’m portuguese.

    • http://www.caloriesproper.com/ William Lagakos

      Hi Maria,

      Thanks!

      From everything I’ve seen (and understand about fats & lipid metabolism), there’s nothing bad about coconut oil; it’s “healthy.” But honestly, I don’t know very much about the efficacy of coconut oil in treating Hashimoto’s. My only advice would be to have this discussion with your doctor. I suspect you’ll hear it’s not the recommended course of therapy, but it might be worth a try.

  • mk07

    I would be very grateful if you could take a bit of your time to answer some of my questions.

    1. What’s your opinion on what Paul Jaminet said about glucose
    deficiency, and low carb riks such as scurvy? He recommends a minimum of
    100g of carbs because of those issues. I would like to have your
    opinion on this.

    2. A friend of fime ended up in the ER a couple of nights ago after a
    booze night out. The doctor said she was hypoglycemic because of the
    alcohol intake and that alcohol causes hypoglycemia in everyone. I wasn’t aware of
    this. Is this true? I had severe reactive hypoglycemia (in the 40’s incluing during the whole night) that I’m trying to manage by following a paleo diet – it’s working – so I’m interested in knowing whether or not I can include alcohol every now and then.

    3. I need to lose 15kg and I know hormones play a huge role in weight loss (specially in women). Since I have hashimoto’s, do you think having Low T3 due to low carb is ok or what numbers should I aim?

    I’m from Spain apologies for my writting

    • http://www.caloriesproper.com/ William Lagakos

      Low carb diets don’t usually cause hypoglycemia, but rather can be pretty a effective treatment for some people. Ymmv.

      Alcohol can impair gluconeogenesis, although I think this is only a problem if you’re fasting.

      I recently wrote an article about thyroid biology. I’m not sure how your Hashimoto’s would play into it, but there might be some useful information: http://caloriesproper.com/?p=4231