Pinolenic acid (often misspelled as pinoleic acid) is a

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, ...

contained in

Siberian Pine ''Pinus sibirica'', or Siberian pine, in the family Pinaceae is a species of pine tree that occurs in Siberia from 58°E in the Ural Mountains east to 126°E in the Stanovoy Range in southern Sakha Republic, and from Igarka at 68°N in the lower ...

nuts,

Korean Pine ''Pinus koraiensis'' is a species of pine known commonly as the Korean pine. It is native to eastern Asia: Korea, northeastern China, Mongolia, the temperate rainforests of the Russian Far East, and central Japan. In the north of its range, it g ...

nuts and the

seed A seed is an embryonic plant enclosed in a protective outer covering, along with a food reserve. The formation of the seed is a part of the process of reproduction in seed plants, the spermatophytes, including the gymnosperm and angiospe ...

s of other pines (''

Pinus A pine is any conifer tree or shrub in the genus ''Pinus'' () of the family Pinaceae. ''Pinus'' is the sole genus in the subfamily Pinoideae. The World Flora Online created by the Royal Botanic Gardens, Kew and Missouri Botanical Garden ...

'' species). The highest percentage of pinolenic acid is found in Siberian

pine nut Pine nuts, also called piñón (), pinoli (), pignoli or chilgoza (), are the edible seeds of pines (family Pinaceae, genus ''Pinus''). According to the Food and Agriculture Organization, only 29 species provide edible nuts, while 20 are trad ...

s and the

oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...

produced from them.

Chemistry and biochemistry

Pinolenic acid is formally designated as ''all-cis-5,9,12-18:3''. Some sources also use the term columbinic acid for this substance. But ''columbinic acid'' sometimes designates an E-Z isomer (''trans'',''cis'',''cis'' ''delta''-5,9,12/18:3) in the biologic literature. Pinolenic acid is an

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 ...

of gamma-linolenic acid (GLA). GLA is an ω-6

essential fatty acid 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. Only two fatty acids are known to be essential for humans: alpha-linolenic ac ...

(EFA) but pinolenic acid is not. However, like the EFAs, it forms biologically active

metabolites In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, ...

in the presence of

cyclooxygenase Cyclooxygenase (COX), officially known as prostaglandin-endoperoxide synthase (PTGS), is an enzyme (specifically, a family of isozymes, ) that is responsible for formation of prostanoids, including thromboxane and prostaglandins such as pr ...

lipoxygenase Lipoxygenases () are a family of (non-heme) iron-containing enzymes most of which catalyze the dioxygenation of polyunsaturated fatty acids in lipids containing a cis,cis-1,4- pentadiene into cell signaling agents that serve diverse roles as aut ...

. These metabolites can partially relieve some of the symptoms of EFA deficiency.

Physiology

Recent research has shown its potential use in

weight loss Weight loss, in the context of medicine, health, or physical fitness, refers to a reduction of the total body mass, by a mean loss of fluid, body fat ( adipose tissue), or lean mass (namely bone mineral deposits, muscle, tendon, and other co ...

by curbing appetite. Pinolenic acid causes the triggering of two hunger suppressants—

cholecystokinin Cholecystokinin (CCK or CCK-PZ; from Greek ''chole'', "bile"; ''cysto'', "sac"; ''kinin'', "move"; hence, ''move the bile-sac (gallbladder)'') is a peptide hormone of the gastrointestinal system responsible for stimulating the digestion of fat and ...

and

glucagon-like peptide-1 Glucagon-like peptide-1 (GLP-1) is a 30- or 31-amino-acid-long peptide hormone deriving from the tissue-specific posttranslational processing of the proglucagon peptide. It is produced and secreted by intestinal enteroendocrine L-cells and cert ...

(GLP-1). Pinolenic acid may have

LDL Low-density lipoprotein (LDL) is one of the five major groups of lipoprotein that transport all fat molecules around the body in extracellular water. These groups, from least dense to most dense, are chylomicrons (aka ULDL by the overall densit ...

-lowering properties by enhancing hepatic

uptake.

References

{{Fatty acids Fatty acids Alkenoic acids