Furan fatty acids

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Furan fatty acids are a group of fatty acids that contain a furan ring. To this furan ring, an unbranched carboxylic acid and, at another position, an alkyl residue are attached. Natural furan fatty acids are mono- or di-methylated on the furan ring. [1] Furan fatty acids can be found in a variety of plant and animal species.

Contents

Carboxy-substituted furan fatty acids are known as urofuran acids. Urofuran fatty acids are metabolic products of furan fatty acids and can be detected, for example, in human urine. [2]

General structure of furan fatty acids FFA.svg
General structure of furan fatty acids

General structure of furan fatty acids

The most abundant methyl-substituted furan fatty acids
mnR
28CH3
48H
48CH3
210CH3
410H
410CH3
412H
412CH3

Occurrence

Furan fatty acids are found mainly in the liver fat of fish, in crustaceans and horn corals. They can also be found in the liver of cattle and rats, as well as in human blood; either in free form or in triglycerides or esterified to cholesterol. In fish, the concentration of furan fatty acids is particularly high in the liver after hunger periods.

Furan fatty acids can be detected in a variety of organisms and products such as butter and butter oil. [3] It is now assumed that this class of compounds is ubiquitous. [4] [5]

Furan fatty acids in animals are based on the uptake and accumulation of furan fatty acids from plant constituents. [6] In human blood, the total furan fatty acid content is about 50 ng/ml. Per day, a person separates between 0.5 and 3 mg of urofuran acids - the metabolic product of the furans acids. [7] [8] [9] Animals are not able to synthesize furan fatty acids. Larger amounts of furan fatty acids are produced mainly by algae, but also some plants and microorganisms. These serve fish and mammals as food. The furan fatty acids thus absorbed are incorporated into phospholipids and cholesterol esters. [8]

Function and physiological effects

The metabolism of furan fatty acids to urofuranic acids in humans. In rats and cattle, the methyl group of the alkyl group is oxidized. FFA metabolism human.svg
The metabolism of furan fatty acids to urofuranic acids in humans. In rats and cattle, the methyl group of the alkyl group is oxidized.

Furan fatty acids are reactive compounds. They are easily oxidizable by photooxidation, [10] autoxidation, [10] [11] [12] or catalyzed by lipoxygenase-1. [10] [13] [14] Upon the exposure to light, the aroma 3-methyl-2,4-nonanedione (MND) is formed from furan fatty acids in the reaction with singlet oxygen, which has a hay-like odor and is found, for example, in green tea. [15] [16]

Furan fatty acids act as radical scavengers. In the example, two hydroxyl radicals are trapped to form a dioxoenoic fatty acid. FFA scavenger.svg
Furan fatty acids act as radical scavengers. In the example, two hydroxyl radicals are trapped to form a dioxoenoic fatty acid.

Furan fatty acids are very effectively acting as radical scavengers. In this process dioxoenoic fatty acids are formed, which are by themselves very unstable and form thioethers with thiols such as cysteine or glutathione. [17] As potent antioxidants, they specifically trap hydroxyl radicals. [18] It is therefore believed that this is in different biological systems their main function. [19] They also inhibit the singlet oxygen-induced hemolysis of red blood cells (red blood cell disintegration). [20] [21]

Plants and algae produce furan fatty acids during the biosynthesis from polyunsaturated fatty acids (PUFA). These are seemingly used in these organisms as protection against free radicals generated by sunlight. [22] [23]

The biosynthesis of furan fatty acids FFA biosynthesis.svg
The biosynthesis of furan fatty acids

Occasionally it is speculated that the health-promoting properties originally attributed to omega-3 fatty acids may not be based on themself, but on the furan fatty acids also present in the fish. [24] [25] A clinical trial of isolated omega-3 fatty acids such as eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA) in patients who have had a myocardial infarction previously showed no significant difference in cardiovascular effects compared to a placebo. [26]

The exact pathological effects of furan fatty acids have not yet been clarified in detail and are the subject of current research. In addition to the antioxidant effect, anti-tumor (against malignant tumors) and antithrombotic effects (anti-thrombosis) are also suspected. [27] In 2002, xenohormonal properties were observed for the two furan fatty acids 9,(12)-oxy-10,13-dihydroxystearic acid and 10,(13)-oxy-9,12-dihydroxystearic acid. In vitro experiments on MCF-7 cells (breast cancer cells with estrogen receptor) revealed mitogenic properties as well as an influence on estrus. In the latter case, the transition to metestrus was initiated. [28] [29] In vivo, a reduction in mating willingness was observed after intake of furan fatty acids on female color rats. [30] However, neither estrogen nor anti-estrogenic activity has been demonstrated. [28] [29] [31] Chickens were found to have no adverse effects on feeding, fertility, egg weight, eggshell thickness, and other reproductive parameters after the intake of furan fatty acids. [31]

History

Furan fatty acids were first detected in 1966 by L. J. Morris and colleagues as part of an oil derived from seeds of Exocarpus cupressiformis (a sandalwood-type plant). [32] Years later, other analysis methods showed that the furan fatty acid 9,12-epoxyoctadeca-9,11-dienoic acid was in fact not contained in the oil of Exocarpus cupressiformis as described by Morris. Instead, it was formed during the sample preparation used by Morries and colleagues for the argentation chromatography by oxidation of hydroxyfatty acids, in a base-catalyzed transesterification. [33] In 1974, furan fatty acids were first identified in pike (Esox lucius) by Robert L. Glass and colleagues using coupled gas chromatography–mass spectrometry (GC-MS). [5] [34]

Literature

Related Research Articles

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<span class="mw-page-title-main">Arachidonic acid</span> Fatty acid used metabolically in many organisms

Arachidonic acid is a polyunsaturated omega-6 fatty acid 20:4(ω-6), or 20:4(5,8,11,14). It is structurally related to the saturated arachidic acid found in cupuaçu butter. Its name derives from the Neo-Latin word arachis (peanut), but peanut oil does not contain any arachidonic acid.

<span class="mw-page-title-main">Eicosanoid</span> Class of compounds

Eicosanoids are signaling molecules made by the enzymatic or non-enzymatic oxidation of arachidonic acid or other polyunsaturated fatty acids (PUFAs) that are, similar to arachidonic acid, around 20 carbon units in length. Eicosanoids are a sub-category of oxylipins, i.e. oxidized fatty acids of diverse carbon units in length, and are distinguished from other oxylipins by their overwhelming importance as cell signaling molecules. Eicosanoids function in diverse physiological systems and pathological processes such as: mounting or inhibiting inflammation, allergy, fever and other immune responses; regulating the abortion of pregnancy and normal childbirth; contributing to the perception of pain; regulating cell growth; controlling blood pressure; and modulating the regional flow of blood to tissues. In performing these roles, eicosanoids most often act as autocrine signaling agents to impact their cells of origin or as paracrine signaling agents to impact cells in the proximity of their cells of origin. Eicosanoids may also act as endocrine agents to control the function of distant cells.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH
2)
7CH=CHCH
2CH=CH(CH
2)
4CH
3. Both alkene groups are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.

<span class="mw-page-title-main">Lipid peroxidation</span> Reaction(s) leading to production of (phospho)lipid peroxides

Lipid peroxidation is the chain of reactions of oxidative degradation of lipids. It is the process in which free radicals "steal" electrons from the lipids in cell membranes, resulting in cell damage. This process proceeds by a free radical chain reaction mechanism. It most often affects polyunsaturated fatty acids, because they contain multiple double bonds in between which lie methylene bridges (-CH2-) that possess especially reactive hydrogen atoms. As with any radical reaction, the reaction consists of three major steps: initiation, propagation, and termination. The chemical products of this oxidation are known as lipid peroxides or lipid oxidation products (LOPs).

<span class="mw-page-title-main">4-Hydroxynonenal</span> Chemical compound

4-Hydroxynonenal, or 4-hydroxy-2-nonenal or 4-HNE or HNE,, is an α,β-unsaturated hydroxyalkenal that is produced by lipid peroxidation in cells. 4-HNE is the primary α,β-unsaturated hydroxyalkenal formed in this process. It is a colorless oil. It is found throughout animal tissues, and in higher quantities during oxidative stress due to the increase in the lipid peroxidation chain reaction, due to the increase in stress events. 4-HNE has been hypothesized to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular adhesion.

<span class="mw-page-title-main">Docosahexaenoic acid</span> Chemical compound

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<span class="mw-page-title-main">Lipoxygenase</span>

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<span class="mw-page-title-main">Pinolenic acid</span> Chemical compound

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<span class="mw-page-title-main">ALOX15</span> Lipoxygenase found in humans

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<span class="mw-page-title-main">ALOX12B</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">ALOXE3</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">12-Hydroxyeicosatetraenoic acid</span> Chemical compound

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<span class="mw-page-title-main">15-Hydroxyeicosatetraenoic acid</span> Chemical compound

15-Hydroxyeicosatetraenoic acid (also termed 15-HETE, 15(S)-HETE, and 15S-HETE) is an eicosanoid, i.e. a metabolite of arachidonic acid. Various cell types metabolize arachidonic acid to 15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HpETE). This initial hydroperoxide product is extremely short-lived in cells: if not otherwise metabolized, it is rapidly reduced to 15(S)-HETE. Both of these metabolites, depending on the cell type which forms them, can be further metabolized to 15-oxo-eicosatetraenoic acid (15-oxo-ETE), 5S,15S-dihydroxy-eicosatetraenoic acid (5(S),15(S)-diHETE), 5-oxo-15(S)-hydroxyeicosatetraenoic acid (5-oxo-15(S)-HETE, a subset of specialized pro-resolving mediators viz., the lipoxins, a class of pro-inflammatory mediators, the eoxins, and other products that have less well-defined activities and functions. Thus, 15(S)-HETE and 15(S)-HpETE, in addition to having intrinsic biological activities, are key precursors to numerous biologically active derivatives.

<span class="mw-page-title-main">Divinylether fatty acids</span>

Divinylether fatty acids contain a fatty acid chemically combined with a doubly unsaturated carbon chain linked by an oxygen atom (ether). Fatty acid hydroperoxides generated by plant lipoxygenases from linoleic and linolenic acids are known to serve as substrates for a divinyl ether synthase which produces divinyl ether fatty acids. Up to date divinyl ethers were detected only within the plant kingdom.

<span class="mw-page-title-main">13-Hydroxyoctadecadienoic acid</span> Chemical compound

13-Hydroxyoctadecadienoic acid (13-HODE) is the commonly used term for 13(S)-hydroxy-9Z,11E-octadecadienoic acid (13(S)-HODE). The production of 13(S)-HODE is often accompanied by the production of its stereoisomer, 13(R)-hydroxy-9Z,11E-octadecadienoic acid (13(R)-HODE). The adjacent figure gives the structure for the (S) stereoisomer of 13-HODE. Two other naturally occurring 13-HODEs that may accompany the production of 13(S)-HODE are its cis-trans (i.e., 9E,11E) isomers viz., 13(S)-hydroxy-9E,11E-octadecadienoic acid (13(S)-EE-HODE) and 13(R)-hydroxy-9E,11E-octadecadienoic acid (13(R)-EE-HODE). Studies credit 13(S)-HODE with a range of clinically relevant bioactivities; recent studies have assigned activities to 13(R)-HODE that differ from those of 13(S)-HODE; and other studies have proposed that one or more of these HODEs mediate physiological and pathological responses, are markers of various human diseases, and/or contribute to the progression of certain diseases in humans. Since, however, many studies on the identification, quantification, and actions of 13(S)-HODE in cells and tissues have employed methods that did not distinguish between these isomers, 13-HODE is used here when the actual isomer studied is unclear.

<span class="mw-page-title-main">Rodolfo Brenner</span> Argentine biochemist

Rodolfo Roberto Brenner was an Argentine emeritus professor of chemistry. He was the founder and director of the Institute of Biochemical Research of La Plata and the co-founder of the Argentine Society for Biochemical Research.

References

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  28. 1 2 Markaverich, BM; Alejandro, MA; Markaverich, D; Zitzow, L; Casajuna, N; Camarao, N; Hill, J; Bhirdo, K; Faith, R; Turk, J; Crowley, JR (2002). "Identification of an endocrine disrupting agent from corn with mitogenic activity". Biochem Biophys Res Commun. 291 (3): 692–700. doi:10.1006/bbrc.2002.6499. PMID   11855846.
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