Conjugated Linoleic Acid
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Conjugated linoleic acids (CLA) are a family of
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...
s of
linoleic acid Linoleic acid (LA) is an organic compound with the formula COOH(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups are cis-trans isomerism, ''cis''. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 ''cis''-9,12. A linoleate is a salt (chem ...
. In principle, 28 isomers are possible. CLA is found mostly in the
meat Meat is animal flesh that is eaten as food. Humans have hunted, farmed, and scavenged animals for meat since prehistoric times. The establishment of settlements in the Neolithic Revolution allowed the domestication of animals such as chic ...
and
dairy product Dairy products or milk products, also known as lacticinia, are food products made from (or containing) milk. The most common dairy animals are cow, water buffalo, nanny goat, and ewe. Dairy products include common grocery store food items in th ...
s derived from
ruminant Ruminants (suborder Ruminantia) are ungulate, hoofed herbivorous grazing or browsing mammals that are able to acquire nutrients from plant-based food by Enteric fermentation, fermenting it in a specialized stomach prior to digestion, principally ...
s. The two C=C double bonds are conjugated (i.e., separated by a single bond). CLAs can be either cis-fats or trans-fats. CLA is marketed as a dietary supplement on the basis of its supposed health benefits.


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. In chemical terms, oleic acid is classified as a monounsaturated omega ...
are produced by microorganisms in the
rumen The rumen, also known as a paunch, is the largest stomach compartment in ruminants and the larger part of the reticulorumen, which is the first chamber in the alimentary canal of ruminant animals. The rumen's microbial favoring environment al ...
s of ruminants. Non-ruminants, including humans, produce certain isomers of CLA from ''trans'' isomers of oleic acid, such as
vaccenic acid 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 tr ...
, 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 COOH(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups are cis-trans isomerism, ''cis''. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 ''cis''-9,12. A linoleate is a salt (chem ...
and
alpha-linolenic acid ''alpha''-Linolenic acid (ALA), also known as α-Linolenic acid (from Greek ''alpha'' meaning "first" and ''linon'' meaning flax), is an ''n''−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, wa ...
, respectively, mainly by ''
Bifidobacterium ''Bifidobacterium'' is a genus of gram-positive, nonmotile, often branched anaerobic bacteria. They are ubiquitous inhabitants of the gastrointestinal tract though strains have been isolated from the vagina and mouth ('' B. dentium'') of mammal ...
''
bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...
strains inhabiting the
gastrointestinal tract The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organ (biology), organs of the digestive syste ...
. 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 oesophagus, stomach, small intestine, large intestine and rectum, and the accessory organs of digestion, the liver, ...
,
gluten sensitivity Non-celiac gluten sensitivity (NCGS) or gluten sensitivity is "a clinical entity induced by the ingestion of gluten leading to intestinal and/or extraintestinal symptoms that improve once the gluten-containing foodstuff is removed from the diet, a ...
, or dysbiosis.


Health effects

CLA is marketed in
dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...
form for its supposed anti-cancer benefit (for which there is no strong evidence or known mechanism, and very few studies conducted so far) and as a bodybuilding aid. A 2004 review of the evidence said that while CLA seemed to benefit animals, there was a lack of good evidence of human health benefits despite the many claims made for it. Likewise, there is insufficient evidence that CLA has a useful benefit for overweight or obese people as it has no long-term effect on body composition. Although CLA has shown an effect on insulin response in diabetic rats, there is no evidence of this effect in humans.


Dietary sources

Food products from grass-fed
ruminant Ruminants (suborder Ruminantia) are ungulate, hoofed herbivorous grazing or browsing mammals that are able to acquire nutrients from plant-based food by Enteric fermentation, fermenting it in a specialized stomach prior to digestion, principally ...
s (e.g. mutton and beef) are good sources of CLA and contain much more of it than those from grain-fed animals.
Eggs Humans and human ancestors have scavenged and eaten animal eggs for millions of years. Humans in Southeast Asia had domesticated chickens and harvested their eggs for food by 1,500 BCE. The most widely consumed eggs are those of fowl, especial ...
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 fruiting body of a fungus, typically produced above ground, on soil, or on its food source. ''Toadstool'' generally denotes one poisonous to humans. The standard for the name "mushroom" is t ...
s, such as ''
Agaricus bisporus ''Agaricus bisporus'' is an edible basidiomycete mushroom native to grasslands in Eurasia and North America. It has two color states while immature – white and brown – both of which have various names, with additional names for the mature ...
'' and ''
Agaricus subrufescens ''Agaricus subrufescens'' (syn. ''Agaricus blazei'', ''Agaricus brasiliensis'' or ''Agaricus rufotegulis'') is a species of mushroom, commonly known as almond mushroom, mushroom of the sun, God's mushroom, mushroom of life, royal sun agaricus, '' ...
'', are rare non-animal sources of CLA. However, dietary
punicic acid Punicic acid (also called trichosanic acid) is a polyunsaturated fatty acid, 18:3 ''cis''-9, ''trans''-11, ''cis''-13. It is named for the pomegranate, (''Punica granatum''), and is obtained from pomegranate seed oil. It has also been found in th ...
—which is abundant in
pomegranate The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punicoideae, that grows between tall. The pomegranate was originally described throughout the Mediterranean Basin, Mediterranean re ...
seeds—is converted to the CLA rumenic acid 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 (GRAS).


See also

*
Conjugated fatty acid Conjugated fatty acids is jargon for polyunsaturated fatty acids containing at least one pair of conjugated double bonds. An example of a conjugated fatty acid is the rumenic acid, found in the meat and milk of ruminants. Most unsaturated fatty ...
s


References

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