Conjugated fatty acid

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Chemical structure of the conjugated fatty acid rumenic acid, an isomer of conjugated linoleic acid Rumenic acid.svg
Chemical structure of the conjugated fatty acid rumenic acid, an isomer of conjugated linoleic acid

Conjugated fatty acids is jargon for polyunsaturated fatty acids containing at least one pair of conjugated double bonds. [1] An example of a conjugated fatty acid is the rumenic acid, found in the meat and milk of ruminants. Most unsaturated fatty acids that are doubly unsaturated do not feature conjugation, e.g., linoleic acid and linoelaidic acid.

Some conjugated fatty acids may confer health benefits ranging from the prevention of hypertension to protection against certain forms of cancer, although more research is needed to confirm such effects. [2] Clinical studies and animal models have shown that conjugated fatty acids confer physiological benefits such as the regulation of the synthesis and breakdown of lipids, reduction of inflammation, and antioxidant properties. [3]

Conjugated fatty acids include isomers of linoleic acid. [4] Conjugated analogues linoleic acids are the most investigated conjugated fatty acids. [5]

Some conjugated fatty acids feature trans alkenes. For instance, the rumenic acid (cis-9, trans-11) is a conjugated trans fatty acid.

Studies have suggested that conjugated linoleic acids, an isomer of conjugated fatty acids, can modulate inflammatory responses in the body. [6] However, CLA’s anti-inflammatory properties correlate to isomer dependence. [7] For instance, (cis-9, trans-11) CLA has been shown to have a decreased inflammatory effect on adipose tissues of mice with obesity-causing genes, while (trans-10, cis-12) CLA reduces obesity in mice without affecting insulin resistance or adipose tissue inflammation. [7]

See also

Related Research Articles

<span class="mw-page-title-main">Fat</span> Esters of fatty acid or triglycerides

In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food.

Essential fatty acids, or EFAs, are fatty acids that humans and other animals must ingest because the body requires them for good health but cannot synthesize them.

<i>alpha</i>-Linolenic acid Chemical compound

alpha-Linolenic acid (ALA), also known as α-Linolenic acid, is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

An unsaturated fat is a fat or fatty acid in which there is at least one double bond within the fatty acid chain. A fatty acid chain is monounsaturated if it contains one double bond, and polyunsaturated if it contains more than one double bond.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH
2
)
7
CH=CHCH
2
CH=CH(CH
2
)
4
CH
3
. Both alkene groups are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.

<span class="mw-page-title-main">Conjugated linoleic acid</span>

Conjugated linoleic acids (CLA) are a family of isomers of linoleic acid. In principle, 28 isomers are possible. CLA is found mostly in the meat and dairy products derived from ruminants. The two C=C double bonds are conjugated. CLAs can be either cis-fats or trans-fats.

In biochemistry and nutrition, polyunsaturated fatty acids are fatty acids that contain more than one double bond in their backbone. This class includes many important compounds, such as essential fatty acids and those that give drying oils their characteristic property.

A fatty acid desaturase is an enzyme that removes two hydrogen atoms from a fatty acid, creating a carbon/carbon double bond. These desaturases are classified as:

Vaccenic acid is a naturally occurring trans fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food.

<span class="mw-page-title-main">Hepoxilin</span> Chemical compound

Hepoxilins (Hx) are a set of epoxyalcohol metabolites of polyunsaturated fatty acids (PUFA), i.e. they possess both an epoxide and an alcohol residue. HxA3, HxB3, and their non-enzymatically formed isomers are nonclassic eicosanoid derived from acid the (PUFA), arachidonic acid. A second group of less well studied hepoxilins, HxA4, HxB4, and their non-enzymatically formed isomers are nonclassical eicosanoids derived from the PUFA, eicosapentaenoic acid. Recently, 14,15-HxA3 and 14,15-HxB3 have been defined as arachidonic acid derivatives that are produced by a different metabolic pathway than HxA3, HxB3, HxA4, or HxB4 and differ from the aforementioned hepoxilins in the positions of their hydroxyl and epoxide residues. Finally, hepoxilin-like products of two other PUFAs, docosahexaenoic acid and linoleic acid, have been described. All of these epoxyalcohol metabolites are at least somewhat unstable and are readily enzymatically or non-enzymatically to their corresponding trihydroxy counterparts, the trioxilins (TrX). HxA3 and HxB3, in particular, are being rapidly metabolized to TrXA3, TrXB3, and TrXC3. Hepoxilins have various biological activities in animal models and/or cultured mammalian tissues and cells. The TrX metabolites of HxA3 and HxB3 have less or no activity in most of the systems studied but in some systems retain the activity of their precursor hepoxilins. Based on these studies, it has been proposed that the hepoxilins and trioxilins function in human physiology and pathology by, for example, promoting inflammation responses and dilating arteries to regulate regional blood flow and blood pressure.

Calendic acid is an unsaturated fatty acid, named for the pot marigold, from which it is obtained. It is chemically similar to the conjugated linoleic acids; laboratory work suggests it may have similar in vitro bioactivities.

<span class="mw-page-title-main">Rumenic acid</span> Chemical compound

Rumenic acid, also known as bovinic acid, is a conjugated linoleic acid (CLA) found in the fat of ruminants and in dairy products. It is an omega-7 trans fatty acid. Its lipid shorthand name is cis-9, trans-11 18:2 acid. The name was proposed by Kramer et al. in 1998. It can be considered as the principal dietary form, accounting for as much as 85-90% of the total CLA content in dairy products.

<span class="mw-page-title-main">Punicic acid</span> Chemical compound

Punicic acid is a polyunsaturated fatty acid, 18:3 cis-9, trans-11, cis-13. It is named for the pomegranate,, and is obtained from pomegranate seed oil. It has also been found in the seed oils of snake gourd.

Linolelaidic acid is an omega-6 trans fatty acid (TFA) and is a cis–trans isomer of linoleic acid. It is found in partially hydrogenated vegetable oils. It is a white viscous liquid.

<span class="mw-page-title-main">Mead acid</span> Chemical compound

Mead acid is an omega-9 fatty acid, first characterized by James F. Mead. As with some other omega-9 polyunsaturated fatty acids, animals can make Mead acid de novo. Its elevated presence in the blood is an indication of essential fatty acid deficiency. Mead acid is found in large quantities in cartilage.

<span class="mw-page-title-main">Stearoyl-CoA 9-desaturase</span> Class of enzymes

Stearoyl-CoA desaturase (Δ-9-desaturase) is an endoplasmic reticulum enzyme that catalyzes the rate-limiting step in the formation of monounsaturated fatty acids (MUFAs), specifically oleate and palmitoleate from stearoyl-CoA and palmitoyl-CoA. Oleate and palmitoleate are major components of membrane phospholipids, cholesterol esters and alkyl-diacylglycerol. In humans, the enzyme is encoded by the SCD gene.

<i>alpha</i>-Parinaric acid Chemical compound

α-Parinaric acid is a conjugated polyunsaturated fatty acid. Discovered by Tsujimoto and Koyanagi in 1933, it contains 18 carbon atoms and 4 conjugated double bonds. The repeating single bond-double bond structure of α-parinaric acid distinguishes it structurally and chemically from the usual "methylene-interrupted" arrangement of polyunsaturated fatty acids that have double-bonds and single bonds separated by a methylene unit (−CH2−). Because of the fluorescent properties conferred by the alternating double bonds, α-parinaric acid is commonly used as a molecular probe in the study of biomembranes.

<span class="mw-page-title-main">Coronaric acid</span> Chemical compound

Coronaric acid (isoleukotoxin) is a mono-unsaturated, epoxide derivative of the di-saturated fatty acid, linoleic acid (i.e. 9(Z),12(Z) octadecadienoic acid). It is a mixture of the two optically active isomers of 12(Z) 9,10-epoxy-octadecenoic acid. This mixture is also termed 9,10-epoxy-12Z-octadecenoic acid or 9(10)-EpOME and when formed by or studied in mammalians, isoleukotoxin.

<span class="mw-page-title-main">Epoxyeicosatetraenoic acid</span> Chemical compound

Epoxyeicosatetraenoic acids are a set of biologically active epoxides that various cell types make by metabolizing the omega 3 fatty acid, eicosapentaenoic acid (EPA), with certain cytochrome P450 epoxygenases. These epoxygenases can metabolize EPA to as many as 10 epoxides that differ in the site and/or stereoisomer of the epoxide formed; however, the formed EEQs, while differing in potency, often have similar bioactivities and are commonly considered together.

<span class="mw-page-title-main">Trans fat</span> Type of unsaturated fat

Trans fat, also called trans-unsaturated fatty acids, or trans fatty acids, is a type of unsaturated fat that occurs in foods. Trace concentrations of trans fats occur naturally, but large amounts are found in some processed foods. Since consumption of trans fats is unhealthy, artificial trans fats are highly regulated or banned in many nations. However, they are still widely consumed in developing nations, resulting in hundreds of thousands of deaths each year. Serious interest has been given to determining their sources, to better avoid them.

References

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  2. Nagao, K; Yanagita, T (2005). "Conjugated fatty acids in food and their health benefits". Journal of Bioscience and Bioengineering. 100 (2): 152–7. doi:10.1263/jbb.100.152. PMID   16198256.
  3. Gong, Mengyue; Hu, Yulin; Wei, Wei; Jin, Qingzhe; Wang, Xingguo (2019-12-01). "Production of conjugated fatty acids: A review of recent advances". Biotechnology Advances. 37 (8): 107454. doi:10.1016/j.biotechadv.2019.107454. ISSN   0734-9750. PMID   31639444. S2CID   204849936.
  4. Hennessy, Alan A.; Ross, Paul R.; Fitzgerald, Gerald F.; Stanton, Catherine (April 2016). "Sources and Bioactive Properties of Conjugated Dietary Fatty Acids". Lipids. 51 (4): 377–397. doi:10.1007/s11745-016-4135-z. ISSN   0024-4201. PMID   26968402. S2CID   3941392.
  5. Gong, Mengyue; Hu, Yulin; Wei, Wei; Jin, Qingzhe; Wang, Xingguo (2019-12-01). "Production of conjugated fatty acids: A review of recent advances". Biotechnology Advances. 37 (8): 107454. doi:10.1016/j.biotechadv.2019.107454. ISSN   0734-9750. PMID   31639444. S2CID   204849936.
  6. Park, Yeonhwa (January 2009). "Conjugated linoleic acid (CLA): Good or bad trans fat?". Journal of Food Composition and Analysis. 22: S4–S12. doi:10.1016/j.jfca.2008.12.002.
  7. 1 2 Yuan, Gaofeng; Chen, Xiaoe; Li, Duo (2015-02-25). "Modulation of Peroxisome Proliferator-Activated Receptor gamma (PPAR γ) by Conjugated Fatty Acid in Obesity and Inflammatory Bowel Disease". Journal of Agricultural and Food Chemistry. 63 (7): 1883–1895. doi:10.1021/jf505050c. ISSN   0021-8561. PMID   25634802.