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Conjugated linoleic acids (CLA) are a family of
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
s of
linoleic acid Linoleic acid (LA) is an organic compound with the formula . 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. Linoleic acid is a polyunsat ...
. In principle, 28 isomers are possible. CLA is found mostly in the
meat Meat is animal Tissue (biology), tissue, often muscle, that is eaten as food. Humans have hunted and farmed other animals for meat since prehistory. The Neolithic Revolution allowed the domestication of vertebrates, including chickens, sheep, ...
and
dairy product Dairy products or milk products are food products made from (or containing) milk. The most common dairy animals are cow, water buffalo, goat, nanny goat, and Sheep, ewe. Dairy products include common grocery store food around the world such as y ...
s derived from
ruminant Ruminants are herbivorous grazing or browsing artiodactyls belonging to the suborder Ruminantia that are able to acquire nutrients from plant-based food by fermenting it in a specialized stomach prior to digestion, principally through microb ...
s. The two C=C double bonds are conjugated (i.e., separated by a single bond) as opposed by "typical"
polyunsaturated fatty acids In biochemistry and nutrition, a polyunsaturated fat is a fat that contains a polyunsaturated fatty acid (abbreviated PUFA), which is a subclass of fatty acid characterized by a backbone with two or more carbon–carbon double bonds. Some polyunsa ...
where double bonds are separated by two single bonds. CLAs are simultaneously both cis-fats and
trans-fats Trans fat is a type of unsaturated fat that occurs in foods. Small amounts of trans fats occur naturally, but large amounts are found in some processed foods made with partially hydrogenated oils. Because consumption of trans fats is associated ...
, as one of the two C=C bonds is ''cis'' and the other ''trans''. CLA is naturally present in milkfat and
beef Beef is the culinary name for meat from cattle (''Bos taurus''). Beef can be prepared in various ways; Cut of beef, cuts are often used for steak, which can be cooked to varying degrees of doneness, while trimmings are often Ground beef, grou ...
, has shown some potentially beneficial effects on rodent models of cardiometabolic disease, and is also available as a dietary supplement.


Biochemistry

CLA describes a variety of isomers of octadecadienoic fatty acids. Commonly, CLAs are studied as some mixture of isomers wherein the isomers c9,t11-CLA (rumenic acid) and t10,c12-CLA were the most abundant. Studies show however that individual isomers have distinct health effects. Conjugated linoleic acid is both a ''trans'' fatty acid and a ''cis'' fatty acid. The ''cis'' bond causes a lower melting point and, ostensibly, also the observed beneficial health effects. Unlike other ''trans'' fatty acids, it may have beneficial effects on human health. CLA is conjugated, and in the United States, ''trans'' linkages in a conjugated system are not counted as ''trans'' fats for the purposes of nutritional regulations and labeling. CLA and some ''trans'' isomers of
oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is cl ...
are produced by microorganisms in the
rumen The rumen, also known as a paunch, is the largest stomach compartment in ruminants. The rumen and the reticulum make up the reticulorumen in ruminant animals. The diverse microbial communities in the rumen allows it to serve as the primary si ...
s of ruminants. Non-ruminants, including humans, produce certain isomers of CLA from ''trans'' isomers of oleic acid, such as vaccenic acid, which is converted to CLA by delta-9-desaturase. In healthy humans, CLA and the related conjugated linolenic acid (CLNA) isomers are bioconverted from
linoleic acid Linoleic acid (LA) is an organic compound with the formula . 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. Linoleic acid is a polyunsat ...
and alpha-linolenic acid, respectively, mainly by '' Bifidobacterium''
bacteria Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micr ...
strains inhabiting the
gastrointestinal tract The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the Digestion, digestive system that leads from the mouth to the anus. The tract is the largest of the body's systems, after the cardiovascula ...
. However, this bioconversion may not occur at any significant level in those with a
digestive disease Gastrointestinal diseases (abbrev. GI diseases or GI illnesses) refer to diseases involving the gastrointestinal tract, namely the esophagus, stomach, small intestine, large intestine and rectum; and the accessory organs of digestion, the liver, ...
, gluten sensitivity, or dysbiosis.


Health effects

CLA is marketed in
dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...
form for its supposed anti-cancer benefit (for which there is a lack of robust evidence or well-accepted mechanism, and very few studies conducted so far) and as a bodybuilding aid. A 2004 review of the evidence said that while CLA seemed beneficial in animal models, there was a lack of good evidence for health benefits in humans despite the many claims made for CLA supplementation. Likewise, there is insufficient evidence that CLA has a useful benefit for overweight or obese people, as it has been found to have no long-term effect on body composition. Although CLA has shown an effect on insulin response in diabetic rats, there is currently no evidence of this effect in humans.


Dietary sources

Food products from grass-fed
ruminant Ruminants are herbivorous grazing or browsing artiodactyls belonging to the suborder Ruminantia that are able to acquire nutrients from plant-based food by fermenting it in a specialized stomach prior to digestion, principally through microb ...
s (e.g. mutton and beef) are good sources of CLA and contain much more of it than those from grain-fed animals. Eggs from chickens that have been fed CLA are also rich in CLA, and CLA in egg yolks has been shown to survive the temperatures encountered during frying. Some
mushroom A mushroom or toadstool is the fleshy, spore-bearing Sporocarp (fungi), fruiting body of a fungus, typically produced above ground on soil or another food source. ''Toadstool'' generally refers to a poisonous mushroom. The standard for the n ...
s, such as ''
Agaricus bisporus ''Agaricus bisporus'', commonly known as the cultivated mushroom, is a basidiomycete mushroom native to grasslands in Eurasia and North America. It is cultivated in more than 70 countries and is one of the most commonly and widely consumed ...
'' and '' Agaricus subrufescens'', are rare non-animal sources of CLA. However, dietary punicic acid—which is abundant in
pomegranate The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punica, Punicoideae, that grows between tall. Rich in symbolic and mythological associations in many cultures, it is thought to have o ...
seeds—is converted to the rumenic acid (which is 9Z11E-CLA) upon absorption in rats, suggesting that non-animal sources can still effectively provide dietary CLA.


History

In 1979 CLAs were found to inhibit chemically-induced cancer in mice and research on its biological activity has continued. In 2008, the United States Food and Drug Administration categorized CLA as
generally recognized as safe Generally recognized as safe (GRAS) is a United States Food and Drug Administration (FDA) designation that a chemical or substance added to food is considered safe by experts under the conditions of its intended use. An ingredient with a GRAS d ...
(GRAS).


See also

* Conjugated fatty acids


References

{{DEFAULTSORT:Conjugated Linoleic Acid Aromatase inhibitors Dietary supplements Fatty acids