Do You Know Vaccenic Acid? And Is Cis or Trans Better?

While exploring the positive effects of various conjugated linoleic acids (CLA), I also found studies on the effect of CLA on the development of cancer and tumors. Results from animal experiments make therapies based on supplementing several percent of CLA appear very interesting. For example, this study of artificially induced cancer (DMBA) in rats shows the effect of adding 0% (A3), 1% (B3), and 2% CLA (C3) to the diet.

The results are very interesting, approximately a 10-fold reduction in both the number and size of tumors. For such a small dietary change, this is quite a large effect. What could be causing it?

The same study also reports that dietary CLA reduces the activity of certain enzymes involved in processing polyunsaturated fats (D6D, delta-6-desaturase). This reduces the conversion of linoleic acid into arachidonic acid and its concentration in membranes. But it also reduces the conversion of the plant omega-3 ALA into the long-chain omega-3s EPA and DHA. As we will show later, reduced activity of the ELOVL5 enzyme could play a key role in this.

We can also look at the composition of the supplemented fat; the CLA fats here replaced part of the oleic acid in the diet.

CLA supplementation also reduces liver weight, thus acting against fatty liver (liver weight).

Let’s continue. Perhaps we do not need to supplement ready-made CLA, but only supplement some substrate from which the body can produce CLA itself.

Yes, such a substrate exists. It is a somewhat strange omega-7 “oleic-like” monounsaturated fatty acid called vaccenic acid, because it also comes from beef fat and meat, that is, from cows (Latin: vacca).

It appears that trans-vaccenic acid (TVA) itself also acts against tumor growth and induces the death of cancer cells. It reduces the sensitivity of GPR43 receptors, which are activated by short-chain fats and suppress the activity of immune T-cells. In this way, TVA acts against the effects of acetate/vinegar; see the previous images and studies. You will find details there.


What does AI tell us about vaccenic acid?

“It is a naturally occurring trans fatty acid and an omega-7 fatty acid. Here are its main characteristics:

Occurrence: It is naturally formed in the digestive tract of ruminants (cows, sheep). Therefore, it is most commonly found in dairy products (milk, butter, cheese) and beef.

Human body: It is the main trans fatty acid present in breast milk.

Health benefits: Unlike industrially produced trans fatty acids, vaccenic acid has a more favorable effect on health. In the body, it is partially converted into so-called conjugated linoleic acid (CLA), which exhibits anti-inflammatory and other health-promoting effects.”


So, if I understand correctly, human cells can produce c9,t11-CLA from vaccenic acid C18n-7t. To clarify, n-7t means the seventh carbon from the end, while t11 means the eleventh carbon from the beginning — therefore the same position on the chain. The enzyme SCD1 desaturates chains at the ninth position, for example converting C18:0 into C18:1n-9c, that is, stearic acid into oleic acid. If applied to TVA, it produces c9,t11-CLA.

Let’s continue further. Human cells alone can also use the enzyme SCD1 to perform desaturation and, through elongation, create vaccenic acid from saturated C16:0 via C16:1n-7c into C18:1n-7c, that is, vaccenic acid. But beware! Here the product is cis-vaccenic acid (CVA). It does not come from milk fat. Up to this point, we have always meant trans-vaccenic acid (TVA).

What can this cis-vaccenic acid (CVA) do?

The authors of this study examined the correlation between insulin resistance, insulin levels, and levels of cis-vaccenic acid (CVA). They created a regression model in which, after detailed analysis, they found a clear inverse relationship between insulin levels and the amount of CVA in the blood phospholipids. This level can be influenced by the activity of the enzymes SCD1 and ELOVL5. The more CVA, the lower the insulin resistance quantified as HOMA-IR.

Do we know what could be causing this? What is the mechanism? Other studies may give us a clue.

It is the optimization of mitochondrial membrane composition, specifically cardiolipin composition. It appears that CVA is the optimal chain for functional cardiolipin and for supporting mitochondrial ATP energy production through oxidative phosphorylation, while reducing the production of superoxide and hydrogen peroxide — that is, suppressing oxidative stress. Suppression of ELOVL5 function (shELOVL5) slows glucose burning and increases the production of ROS free radicals, while activation of ELOVL5 (hELOVL5) activates higher oxygen consumption at lower oxidative stress.

However, in the case of cancer cells, poorer fat burning and lower ATP energy production lead to smaller tumors and the death of cancer cells. Therefore, the conclusions about what is beneficial and what is not are opposite here compared to normal functional cells. In this context, there is an effort to reduce ELOVL5 activity.

Is there any way to increase ELOVL5? Yes, for example by reducing the intake of omega-6 linoleic acid. This helps preserve the activity of elongases and desaturase enzymes. The body defends itself against rising arachidonic acid levels by suppressing the activity of the enzymes that produce it, for example also by suppressing ELOVL5.

Maintaining high activity of the enzymes that process shorter-chain PUFAs into very long-chain polyunsaturated fats is a good strategy and also makes it possible to preserve CVA production through de novo lipogenesis.

But this also has its downsides. CVA supports the survival of cancer cells and supplies them with energy. Therefore, in the case of already active disease, supporting CVA production may not be the best solution.

However, supplementing TVA, which exhibits anti-cancer effects, could be beneficial. What does this mean for us? It is good to have enough dairy fat in the diet containing TVA and CLA fats.


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References:

The Effect of Conjugated Linoleic Acids (CLA) Supplementation on the Activity of Enzymes Participating in the Formation of Arachidonic Acid in Liver Microsomes of Rats—Probable Mechanism of CLA Anticancer Activity

Trans-vaccenic acid inhibits proliferation and induces apoptosis of human nasopharyngeal carcinoma cells via a mitochondrial-mediated apoptosis pathway

Trans-vaccenic acid reprograms CD8+ T cells and anti-tumour immunity

Associations of plasma phospholipid cis-vaccenic acid with insulin resistance markers in non-diabetic men with hyperlipidemia

Cis-vaccenic acid is a key product of stearoyl-CoA desaturase 1 and a critical oncogenic factor in prostate cancer

ELOVL5 Is a Critical and Targetable Fatty Acid Elongase in Prostate Cancer



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