Effects of Non-Methylene-Interrupted Polyunsaturated Fatty Acid, Sciadonic (All-<i>cis</i>-5,11,14-eicosatrienoic Acid) on Lipid Metabolism in Rats

Endo, Yasushi; Tsunokake, Kumiko; Ikeda, Ikuo

doi:10.1271/bbb.80646

Cited by 25 publications

(18 citation statements)

References 16 publications

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“…1a). In addition, Scia can be elongated into 22:3Δ7,13,16 as previously showed in cultured cells 8,9 but in contrast with in vivo experiments 15,16,24 . In the present trial, this bishomo-sciadonic acid was identified by using DMOX derivatives and GC-MS.…”

Section: Resultssupporting

confidence: 54%

“…These authors reported a large fall in the triglyceride concentration in the liver when rats consumed the Torreya oil but without investigating the effect on monoenes from hepatic triglycerides. Endo et al studied thereafter the nutritional effect of Scia purified from Torreya nucifera but the FA was supplied as the ethyl ester in the diet 16 . After a two-week trial, they observed a 50% reduction of the liver triglyceride concentration in rats previously fasted prior to the tissue collection.…”

Section: Discussionmentioning

confidence: 99%

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Sciadonic acid derived from pine nuts as a food component to reduce plasma triglycerides by inhibiting the rat hepatic Δ9-desaturase

Pédrono

Boulier-Monthéan

Boissel

et al. 2020

Sci Rep

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Sciadonic acid (Scia) is a Δ5-olefinic fatty acid that is particularly abundant in edible pine seeds and that exhibits an unusual polymethylene-interrupted structure. Earlier studies suggested that Scia inhibited the in vitro expression and activity of the Stearoyl-CoA Desaturase 1 (SCD1), the hepatic Δ9-desaturase involved in the formation of mono-unsaturated fatty acids. To confirm this hypothesis, rats were given 10% Scia in diets balanced out with n-6 and n-3 fatty acids. In those animals receiving the Scia supplement, monoene synthesis in the liver was reduced, which was partly attributed to the inhibition of SCD1 expression. As a consequence, the presence of Scia induced a 50% decrease in triglycerides in blood plasma due to a reduced level of VLDL-secreted triglycerides from the liver. In non-fasting conditions, results showed that Scia-induced inhibition of SCD1 led to a decrease in the proportions of 16:1n-7 and 18:1n-7 in the liver without impacting on the level of 18:1n-9, suggesting that only triglycerides with neosynthesized monoenes are marked out for release. In conclusion, this in vivo study confirms that Scia highly inhibits SCD1 expression and activity. The work was performed on normotriglyceride rats over six weeks, suggesting promising effects on hyper-triglyceridemic models. Sciadonic acid (Scia) is composed of an aliphatic chain with 20 carbons and 3 unsaturations (20:3Δ5,11,14). It is a Δ5-olefinic acid, a fatty acid (FA) group characterized by the presence of a polymethylene-interrupted double bond at C5, as distinct from the more common malonic structure. In the natural environment, Scia is specifically abundant in conifers, although it is also present in trace amounts with different other olefinic structures in slime molds 1 and certain marine invertebrates 2. Seven Δ5-olefinic acids are commonly found in gymnosperms and their composition profile provides a good marker of the plant phylogeny 3,4. Scia is particularly associated with the suborder Taxares, representing up to 26% of the total FA content in Podocarpus nagi 5. It is ubiquitously found in pine nuts, constituting up to 7% of the total FA in Pinus pinaster 6. As it is present in edible seeds and consumed as a nutrient, studies performed on rodent models have been carried out to determine its functional effect. Scia is incorporated in membranes when supplied to the cells and substitutes for arachidonic acid (20:4n-6) in phospholipids such as phosphatidylinositol 7. Consequently, this unusual FA integrates lipid metabolism resulting in the modulation of physiological functions. Scia supplemented to mammal cells induces synthesis of the uncommon 16:2n-6 (Δ7,10), which is subsequently elongated into linoleic acid (18:2n-6 or Δ9,12) 8,9. Scia then reduces the production of modulators causing inflammation that are derived from arachidonic acid 10-13. In rats fed with a Scia-enriched diet, triglyceride levels are lowered in the blood plasma and the liver 14-16. Previous work performed in vitro on hepatocytes showed that Scia inhibited ...

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Section: Resultssupporting

confidence: 54%

Section: Discussionmentioning

confidence: 99%

Sciadonic acid derived from pine nuts as a food component to reduce plasma triglycerides by inhibiting the rat hepatic Δ9-desaturase

Pédrono

Boulier-Monthéan

Boissel

et al. 2020

Sci Rep

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show abstract

“…By increasing the pool of monoenes in hepatocytes, SCD1 contributes to triacylglycerol neosynthesis, in which its availability regulates VLDL assembly and secretion. Its inhibition by Scia consequently reduced the secretion of triacylglycerols by hepatocytes, as previously underlined by in vivo studies . De novo neosynthesis of triacylglycerols is regulated by sterol regulatory element‐binding protein 1c, a hepatic gene transcription factor that stimulates the synthesis of lipogenic enzymes.…”

Section: Discussionmentioning

confidence: 72%

“…The physiological effects of Scia were consequently attributed to this arachidonate substitution. Nevertheless Scia was also shown to lower by itself the level of triacylglycerols in plasma and liver …”

Section: Discussionmentioning

confidence: 98%

The Hypotriglyceridemic Effect of Sciadonic Acid is Mediated by the Inhibition of Δ9‐Desaturase Expression and Activity

Pédrono

Boulier-Monthéan

Boissel

et al. 2018

Molecular Nutrition Food Res

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“…Sciadonic acid 5(Z),11(Z),14(Z)-eicosatrienoic acid, SA), also known as podocarpic acid, is also an NMI PUFA present in lower levels in biota seed oil with similar biological properties to juniperonic acid. However, Endo et al suggested that SA may inhibit the synthesis of arachidonic acid from linoleic acid [32]. SA purification has been attempted via countercurrent chromatography and by open column adsorption chromatography followed by reverse-phase HPLC [6].…”

Section: Introductionmentioning

confidence: 99%

Isolation of Non‐methylene Interrupted or Acetylenic Fatty Acids from Seed Oils Using Semi‐preparative Supercritical Chromatography

Montañés

Tallon

Catchpole

2017

J Americ Oil Chem Soc

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Preparative scale supercritical fluid chromatography was used for isolating and purifying uncommon non‐methylene interrupted or acetylenic polyunsaturated fatty acids ethyl esters from seed oils. Fractionation of Biota orientalis seed oil ethyl esters was performed by supercritical fluid chromatography to obtain juniperonic acid [(5Z,11Z,14Z,17Z)‐eicosa‐5,11,14,17‐tetraenoic acid], a non‐methylene interrupted polyunsaturated fatty acid. Fractionation of sandalwood seed oil ethyl esters yielded ximenynic acid [(E)‐octadec‐11‐en‐9‐ynoic acid], an acetylenic polyunsaturated fatty acid. The effects of CO2 flow rate, column stationary phase and particle size were explored to optimize ximenynic and juniperonic ethyl ester recovery and purity from ethyl ester mixtures using online UV/Vis detection. Particle size, followed by the stationary phase, were found to be the most important parameters to achieving good separation. Under optimized conditions, ximenynic and juniperonic ethyl ester purities greater than 99 and 95%, respectively, were achieved in a one step process without co‐solvent. The isolation and recovery of juniperonic acid from biota seed oil free fatty acids was also attempted. Using free fatty acids as the feed material, the non‐methylene interrupted polyunsaturated sciadonic acid was also able to be separated from other compounds including juniperonic acid under some conditions, and gave an increase in concentration of more than 17 times.

show abstract

Effects of Non-Methylene-Interrupted Polyunsaturated Fatty Acid, Sciadonic (All-cis-5,11,14-eicosatrienoic Acid) on Lipid Metabolism in Rats

Cited by 25 publications

References 16 publications

Sciadonic acid derived from pine nuts as a food component to reduce plasma triglycerides by inhibiting the rat hepatic Δ9-desaturase

Sciadonic acid derived from pine nuts as a food component to reduce plasma triglycerides by inhibiting the rat hepatic Δ9-desaturase

The Hypotriglyceridemic Effect of Sciadonic Acid is Mediated by the Inhibition of Δ9‐Desaturase Expression and Activity

Isolation of Non‐methylene Interrupted or Acetylenic Fatty Acids from Seed Oils Using Semi‐preparative Supercritical Chromatography

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