PINOLENIC ACID

Pinolenic acid (often misspelled as pinoleic acid) is a fatty acid contained in Siberian Pine nuts, Korean Pine nuts and the seeds of other pines (Pinus species). 
The highest percentage of pinolenic acid is found in Siberian pine nuts and the oil produced from them.

CAS Number: 16833-54-8
IUPAC Name: (5Z,9Z,12Z)-Octadeca-5,9,12-trienoic acid
Chemical Formula: C18H30O2

Other names: 16833-54-8, (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid, 5Z,9Z,12Z-octadecatrienoic acid, cis,cis,cis-5,9,12-Octadecatrienoic acid, B810C93MD7, 5,9,12-Octadecatrienoic acid, (5Z,9Z,12Z)-, DTXSID00895852, DTXCID801325350, Pinolenic acid [MI], C18:3n-6,9,13, UNII-B810C93MD7, orb1694449, SCHEMBL1021463, CHEBI:86136, HXQHFNIKBKZGRP-URPRIDOGSA-N, HMS3650G16, LMFA01030344, MSK164627, (5Z,9Z,12Z)-octadecatrienoic acid, AKOS040754743, all-cis-octadeca-5,9,12-trienoic acid, (z,z,z)-5,9,12-octadecatrienoic acid, 1ST164627, 5,9,12-OCTADECATRIENOIC ACID, CIS, HY-119546, CS-0068703, SR-01000946285, SR-01000946285-1, Q63408763

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 of gamma-linolenic acid (GLA). GLA is an ω-6 essential fatty acid (EFA) but pinolenic acid is not. 
However, like the EFAs, it forms biologically active metabolites in the presence of cyclooxygenase or lipoxygenase. 
These metabolites can partially relieve some of the symptoms of EFA deficiency.

Physiology
Recent research has shown its potential use in weight loss by curbing appetite.
Pinolenic acid causes the triggering of two hunger suppressants—cholecystokinin and glucagon-like peptide-1 (GLP-1). 
Pinolenic acid may have LDL-lowering properties by enhancing hepatic LDL uptake.

Pinolenic acid is an octadecatrienoic acid having three double bonds located at positions 5, 9 and 12 (the all-cis-isomer). 
It has a role as a plant metabolite and an antineoplastic agent.

Pinolenic acid is a natural product found in Teucrium cubense and Pinus koraiensis with data available.
Pinolenic Acid is found in pine nuts in commercial samples that results in pine nut syndrome.

Pinolenic acid is a polyunsaturated fatty acid found in Korean pine (Pinus orientalis) and maritime pine (Pinus pinaster) seed oils. Both oils have been found to have lipid-lowering properties. 
A diet containing maritime pine seed oil (MPSO) lowered HDL and ApoA1 levels in transgenic mice expressing human ApoA1. 

MPSO was found to diminish cholesterol efflux in vitro.1 Korean pine seed oil supplements may help in obesity by reduction of appetite. 
People taking this oil had an increase in the satiety hormones CCK and GLP-1 and a reduced desire to eat.
The activity of the oil is attributed to pinolenic acid. 
Pinolenic acid is not converted to arachidonic acid metabolically and can reduce arachidonic acid levels in the phosphatidylinositol fraction of HepG2 cells from 15.9% to 7.0%.

Pinolenic acid (PLA) is a polyunsaturated fatty acid of plant origin. 
PLA has been successfully enriched according to a two-step process involving lipase-catalysed esterification and urea complexation. 
For the first step, the fatty acids present in pine nut oil were selectively esterified with lauryl alcohol using Candida rugosa lipase. 

Under the optimum conditions of 0.1% enzyme loading, 10% additional water, and 15°C, PLA was enriched up to 43mol% from an initial value of 13mol% in the pine nut oil. 
For the second step, the PLA-enriched fraction from the first step was subjected to a urea complexation process. 
In this way, PLA enrichments with purities greater than 95mol% were obtained at urea to fatty acid ratios greater than 3:1 (wt/wt), and 100% pure PLA was produced at a urea to fatty acid ratio of 5:1 with an 8.7mol% yield.

Pinolenic acid, omega 6, extracted from pinus koraiensis nut oil, has function of lowering cholesterol, treating obesity and diabetes,etc.

Pinolenic Acid is a polyunsaturated fatty acid found in maritime pine (Pinus pinaster) and Korean pine (Pinus orientalis) seed oils, where both oils have lipid-lowering properties. 
Pinolenic acid is an isomer of gamma-linolenic acid and forms biologically acitve metabolites in the presence of cyclooxygenase or lipoxygenase. 
A diet containing maritime pine seed oil (MPSO) lowered HDL and ApoA1 levels in transgenic mice expressing human ApoA1. 

MPSO was found to diminish cholesterol efflux in vitro. 
Korean pine seed oil supplements may help in obesity by reduction of appetite. 
The activity of the oil is attributed to pinolenic acid. 
Pinolenic acid may have LDL-lowering properties by enhancing hepatic LDL uptake.

Pinolenic acid is a polyunsaturated fatty acid found in Korean pine (Pinus orientalis) and maritime pine (Pinus pinaster) seed oils. 
Both oils have been found to have lipid-lowering properties. 
A diet containing maritime pine seed oil (MPSO) lowered HDL and ApoA1 levels in transgenic mice expressing human ApoA1. 
MPSO was found to diminish cholesterol efflux in vitro. 

Korean pine seed oil supplements may help in obesity by reduction of appetite. 
People taking this oil had an increase in the satiety hormones CCK and GLP-1 and a reduced desire to eat. 
The activity of the oil is attributed to pinolenic acid. 
Pinolenic acid is not converted to arachidonic acid metabolically and can reduce arachidonic acid levels in the phosphatidylinositol fraction of HepG2 cells from 15.9% to 7.0%.