Novel non-methylated furan fatty acids in fish from a zero discharge aquaculture system

Vetter, Walter; Ulms, Kerstin; Wendlinger, Christine; Rijn, Jaap van

doi:10.1016/j.nfs.2015.11.001

Cited by 11 publications

(14 citation statements)

References 23 publications

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“…Helium (purity 99.9990%) was used as the carrier gas at a constant flow rate of 1 mL/min. A 30 m × 0.25 mm inner diameter capillary column coated with 0.25 μm of 5% phenyl and 95% methyl polysiloxane (HP‐5MS UI, Agilent, Waldbronn, Germany) was used in combination with the following GC oven program: After 1 min at 60 °C, the temperature was ramped at 13 °C/min to 180 °C; at 3 °C/min to 250 °C; and finally at 20 °C/min to 300 °C, which was held for 5 min (Vetter et al, ).…”

Section: Methodsmentioning

confidence: 99%

The Furan Fatty Acid 9M5 Acts as a Partial Ligand to Peroxisome Proliferator‐Activated Receptor gamma and Enhances Adipogenesis in 3T3‐L1 Preadipocytes

Lauvai

Becker

Lehnert

et al. 2019

Lipids

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A food that has been praised for its beneficial effects on overall health is fish, particularly its polyunsaturated n-3 fatty acids, including docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA). However, it has recently been suggested that minor fatty acids such as furan fatty acids are needed in combination with DHA and EPA to exert these positive effects of fish and fish oils. Only recently have furan fatty acids become available in quantities that allow the investigation of their biofunctional properties. In this study, the uptake and effect of the furan fatty acid 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid (9M5) as a sole component and in combination with DHA and EPA on adipogenesis were analyzed using the 3T3-L1 cell model. 9M5 is taken up and metabolized into 7M5, 5M5, and 3M5 in 3T3-L1 adipocytes during a 24-h period as shown with gas chromatography with mass spectrometry (GC/MS). Furthermore, 9M5 significantly increased lipid accumulation during the differentiation process of 3T3-L1 preadipocytes into adipocytes. In addition, the combinations of DHA + 9M5 and EPA + DHA + 9M5 also exerted a significant increase compared to control adipocytes. 3T3-L1 cells incubated with 9M5 resulted in an increased protein expression of PPARγ, C/EBPα, FABP4, and adiponectin, although not to the extent that DHA as a sole component or DHA + 9M5 did. Earlier studies have shown that DHA is a natural ligand for PPARγ, thus being a potential alternative to the antidiabetic thiazolidinediones. We show that 9M5 activates a PPARγ-responsive reporter gene and could therefore be a natural ligand for PPARγ.

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Section: Methodsmentioning

confidence: 99%

The Furan Fatty Acid 9M5 Acts as a Partial Ligand to Peroxisome Proliferator‐Activated Receptor gamma and Enhances Adipogenesis in 3T3‐L1 Preadipocytes

Lauvai

Becker

Lehnert

et al. 2019

Lipids

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“…In addition, 3,4-nonmethylated furan fatty acids (N-FuFAs) were scarcely reported to occur in food samples [23]. N-FuFAs were not biosynthesised like D-/M-FuFAs but were described as secondary oxidation products of conjugated linoleic acids (CLAs) in model reactions [24,25].…”

Section: Introductionmentioning

confidence: 99%

“…N-FuFAs were mainly formed during photooxidation in presence of singlet oxygen via a cyclic endoperoxide as an intermediate [25][26][27]. However, N-FuFAs were described in food only once, namely in fish and fish feed from a zero discharge aquaculture [23]. Vetter et al reported that N-FuFAs were present in fish feed [23].…”

Section: Introductionmentioning

confidence: 99%

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Valuable furan fatty acids in soybeans and soy products

Müller

Hogg

Vetter

2020

Eur Food Res Technol

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Furan fatty acids (FuFAs) are valuable minor compounds in our food with excellent antioxidant properties. Naturally occurring FuFAs are characterised by a central furan moiety with one or two methyl groups in β-/β'-position of the heterocycle (monomethyl-or M-FuFAs and dimethyl-or D-FuFAs). Comparably high concentrations of D-/M-FuFAs were reported in soybeans, but soy is often consumed as a processed product, such as full-fat soy flour and flakes, soy drink, tofu and texturised soy protein (TSP). Due to the chemical lability of D-/M-FuFAs, e.g. in the presence of light or oxygen, a degradation during the processing is possible. For this purpose, freshly harvested soybeans (n = 4) and differently processed soybean products (n = 22) were analysed on FuFAs. Three FuFAs, i.e. 11-(3,4-dimethyl-5-pentylfuran-2-yl)-undecanoic acid (11D5), 9-(3,4-dimethyl-5-pentylfuran-2-yl)-nonanoic acid (9D5), and 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid (9M5), were identified and quantified in all fresh soybeans and most of the processed soy products (n = 20). A trend towards lower D-/M-FuFA contents in higher processed products was observable. Lower FuFA concentrations were usually accompanied with a decrease of the share of the less stable D-FuFAs (9D5, 11D5) in favour of the M-FuFA 9M5. Furthermore, one or two 3,4-nonmethylated furan fatty acids (N-FuFAs), i.e. 8-(5-hexylfuran-2-yl)-octanoic acid (8F6) and partly 7-(5-heptylfuran-2-yl)-heptanoic acid (7F7), were detected in all processed products, but not in the freshly harvested soybeans. Our results indicate that D-/M-/N-FuFAs may serve as suitable markers for both, careful manufacturing processes and adequate storage conditions of soy products.

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“…There is significant potential to produce natural or modified fatty acids through synthetic biology or cellular engineering, given the range of known acyl chains and the number of gene products predicted to produce or modify these compounds across the phylogeny. We are studying the biosynthetic pathway for an unusual yet important fatty acid, a 19-carbon monomethylated furan fatty acid, 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid, alternatively named 10,13-epoxy-11-methyl-octadecadienoic acid (9M5-FuFA) ( 13 , 14 ).…”

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confidence: 99%

A bacterial biosynthetic pathway for methylated furan fatty acids

Lemke

Olson

Morse

et al. 2020

Journal of Biological Chemistry

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Fatty acids play many important roles in cells and also in industrial processes. Furan fatty acids (FuFAs) are present in the lipids of some plant, fish, and microbial species and appear to function as second messengers in pathways that protect cells from membrane-damaging agents. We report here the results of chemical, genetic, and synthetic biology experiments to decipher the biosynthesis of the monomethylated FuFA, methyl 9-(3-methyl-5-pentylfuran-2-yl) nonanoate (9M5-FuFA), and its dimethyl counterpart, methyl 9-(3,4-dimethyl-5-pentylfuran-2-yl) nonanoate (9D5-FuFA), in two α-proteobacteria. Each of the steps in FuFA biosynthesis occurs on pre-existing phospholipid fatty acid chains, and we identified pathway intermediates and the gene products that catalyze 9M5-FuFA and 9D5-FuFA synthesis in Rhodobacter sphaeroides 2.4.1 and Rhodopseudomonas palustris CGA009. One previously unknown pathway intermediate was a methylated diunsaturated fatty acid, (10E,12E)-11-methyloctadeca-10,12-dienoic acid (11Me-10t,12t-18:2), produced from (11E)-methyloctadeca-11-enoic acid (11Me-12t-18:1) by a newly identified fatty acid desaturase, UfaD. We also show that molecular oxygen (O2) is the source of the oxygen atom in the furan ring of 9M5-FuFA, and our findings predict that an O2-derived oxygen atom is incorporated into 9M5-FuFA via a protein, UfaO, that uses the 11Me-10t,12t-18:2 fatty acid phospholipid chain as a substrate. We discovered that R. palustris also contains a SAM-dependent methylase, FufM, that produces 9D5-FuFA from 9M5-FuFA. These results uncover the biochemical sequence of intermediates in a bacterial pathway for 9M5-FuFA and 9D5-FuFA biosynthesis and suggest the existence of homologs of the enzymes identified here that could function in FuFA biosynthesis in other organisms.

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Novel non-methylated furan fatty acids in fish from a zero discharge aquaculture system

Cited by 11 publications

References 23 publications

The Furan Fatty Acid 9M5 Acts as a Partial Ligand to Peroxisome Proliferator‐Activated Receptor gamma and Enhances Adipogenesis in 3T3‐L1 Preadipocytes

The Furan Fatty Acid 9M5 Acts as a Partial Ligand to Peroxisome Proliferator‐Activated Receptor gamma and Enhances Adipogenesis in 3T3‐L1 Preadipocytes

Valuable furan fatty acids in soybeans and soy products

A bacterial biosynthetic pathway for methylated furan fatty acids

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