Presence of cyclopropane fatty acids in foods and estimation of dietary intake in the Italian population

Lolli, Veronica; Dall’Asta, Margherita; Rio, Daniele Del; Palla, Gerardo; Caligiani, Augusta

doi:10.1080/09637486.2018.1540556

Cited by 9 publications

(15 citation statements)

References 22 publications

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“…To the best of our knowledge, no previous research has reported the presence of sterculic acid in animal fat and only the presence of its saturated analogues (i.e., dihydrosterculic and lactobacillic acids) has been documented [ 5 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Determination of Cyclopropenoid Fatty Acids in Ewe Milk Fat by GC-MS after Intravenous Administration of Sterculic Acid

Lolli

Toral

Caligiani

et al. 2020

Foods

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Cyclopropenoid fatty acids (CPEFA), found in oilseeds from Malvaceae and Sterculiaceae, have been shown to interfere with the endogenous synthesis of several bioactive lipids of dairy fat, such as cis-9, trans-11 18:2 and cis-9 18:1, by inhibiting Δ9-desaturase. No previous study has reported the presence of sterculic acid in animal fat and its incorporation in tissues after its administration, due to the lack of a proper methodology. In the present research, a GC-MS method based on cold base derivatization to fatty acids methylesters was developed to determine CPEFA in ewe milk triglycerides, after infusing sterculic acid (0.5 g/day) to six lactating ewes. An alternative derivatization based on silanyzation followed by GC-MS analysis was also tested, showing its possible applicability when CPEFA are present in the form of free fatty acids. Sterculic acid was detected in ewe milk triglycerides, demonstrating its incorporation from the bloodstream into milk by the mammary gland. The mean transfer rate represented 8.0 ± 1.0% of the daily dose. This study provides, for the first time, the presence of sterculic acid in milk fat, supporting the importance of understanding its occurrence in vivo and encouraging further research to determine whether it can be present in foods, such as dairy products, obtained under practical farming conditions.

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Section: Introductionmentioning

confidence: 99%

Determination of Cyclopropenoid Fatty Acids in Ewe Milk Fat by GC-MS after Intravenous Administration of Sterculic Acid

Lolli

Toral

Caligiani

et al. 2020

Foods

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“…It has been postulated that the medium-chain acylcarnitines containing a cyclopropane ring structure are carnitine esters formed during the mitochondrial oxidation of the respective fatty acids (25,27). Bacteria synthesize these fatty acids via cyclopropane fatty acid synthase in their membranes (7) and cyclopropane fatty acids are described in various kind of foods like milk products and bovine meat (16). Antibiotic treatment led to the disappearance of cyclopropanecontaining acylcarnitines in urine and they are also not found in urine of newborns (15).…”

Section: Discussionmentioning

confidence: 99%

“…This acylcarnitine was postulated to be a xenometabolite derivative (27), because the acylgroup contains a cyclopropane ring which has only been described in fatty acids originating from bacteria and plants (4,7). These fatty acids are found in various kind of foods like milk products and bovine meat (16), and may also be produced by gut bacteria (15). In any case, it has been postulated that the xenometabolites are absorbed and delivered via the portal vein and their partial oxidation results in the formation of the respective medium-chain acylcarnitine esters, which can be detected in plasma (27).…”

Section: Introductionmentioning

confidence: 99%

Identification and regulation of the xenometabolite derivatives cis- and trans-3,4-methylene-heptanoylcarnitine in plasma and skeletal muscle of exercising humans

Sobhi

Zhao

Plomgaard

et al. 2020

American Journal of Physiology-Endocrinology and Metabolism

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Little is known about xenometabolites in human metabolism, particularly under exercising conditions. Previously, an exercise-modifiable, likely xenometabolite derivative, cis-3,4-methylene-heptanoylcarnitine, was reported in human plasma. Here, we identified trans-3,4-methylene-heptanoylcarnitine, and its cis-isomer, in plasma and skeletal muscle by liquid chromatography-mass spectrometry. We analyzed the regulation by exercise and the arterial-to-venous differences of these cyclopropane ring-containing carnitine esters over the hepatosplanchnic bed and the exercising leg in plasma samples obtained in three separate studies from young, lean and healthy males. Compared with other medium-chain acylcarnitines, the plasma concentrations of the 3,4-methylene-heptanoylcarnitine isomers only marginally increased with exercise. Both isomers showed a more than twofold increase in the skeletal muscle tissue of the exercising leg; this may have been due to the net effect of fatty acid oxidation in the exercising muscle and uptake from blood. The latter idea is supported by a more than twofold increased net uptake in the exercising leg only. Both isomers showed a constant release from the hepatosplanchnic bed, with an increased release of the trans-isomer after exercise. The isomers differ in their plasma concentration, with a four times higher concentration of the cis-isomer regardless of the exercise state. This is the first approach studying kinetics and fluxes of xenolipid isomers from tissues under exercise conditions, supporting the hypothesis that hepatic metabolism of cyclopropane ring-containing fatty acids is one source of these acylcarnitines in plasma. The data also provide clear evidence for an exercise-dependent regulation of xenometabolites, opening perspectives for future studies about the physiological role of this largely unknown class of metabolites.

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“…Cyclic fatty acids are an unusual class of minor fatty acids that are generally produced by bacteria and less frequently by plants. Cyclopropane fatty acids, such as dihydrosterculic (9,10-methylene-octadecanoic acid) and lactobacillic (11,12-methyleneoctadecanoic acid) acid, and ω-cyclohexyl fatty acids, such as 11-cyclohexylundecanoic and 13-cyclohexyltridecanoic acid, have been identified as minor components in the lipid profile of lactic acid bacteria and rumen microorganisms, respectively, and have been recently detected in foods of animal origin [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Occurrence of Cis-11,12-Methylene-Hexadecanoic Acid in the Red Alga Solieria pacifica (Yamada) Yoshida

et al. 2021

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Fatty acids in marine algae have attracted the attention of natural chemists because of their biological activity. The fatty acid compositions of the Solieriaceae families (Rhodophyceae, Gaigartinales) provide interesting information that unusual cyclic fatty acids have been occasionally found. A survey was conducted to profile the characteristic fatty acid composition of the red alga Solieria pacifica (Yamada) Yoshida using gas chromatography-mass spectrometry (GC-MS), infrared spectroscopy (IR), and proton nuclear magnetic resonance spectroscopy (1H-NMR). In S. pacifica, two cyclopentyl fatty acids, 11-cyclopentylundecanoic acid (7.0%), and 13-cyclopentyltridecanoic acid (4.9%), and a cyclopropane fatty acid, cis-11,12-methylene-hexadecanoic acid (7.9%) contributed significantly to the overall fatty acid profile. In particular, this cyclopropane fatty acid has been primarily found in bacteria, rumen microorganisms or foods of animal origin, and has not previously been found in any other algae. In addition, this alga contains a significant amount of the monoenoic acid cis-11-hexadecenoic acid (9.0%). Therefore, cis-11,12-methylene-hexadecanoic acid in S. pacifica was likely produced by methylene addition to cis-11-hexadecenoic acid.

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Presence of cyclopropane fatty acids in foods and estimation of dietary intake in the Italian population

Cited by 9 publications

References 22 publications

Determination of Cyclopropenoid Fatty Acids in Ewe Milk Fat by GC-MS after Intravenous Administration of Sterculic Acid

Determination of Cyclopropenoid Fatty Acids in Ewe Milk Fat by GC-MS after Intravenous Administration of Sterculic Acid

Identification and regulation of the xenometabolite derivatives cis- and trans-3,4-methylene-heptanoylcarnitine in plasma and skeletal muscle of exercising humans

Occurrence of Cis-11,12-Methylene-Hexadecanoic Acid in the Red Alga Solieria pacifica (Yamada) Yoshida

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