Impact of free hydroxylated and methyl-branched fatty acids on the organization of lipid membranes

Jenske, Ramona; Lindstrom, F. T.; Gröbner, Gerhard; Vetter, Walter

doi:10.1016/j.chemphyslip.2008.03.010

Cited by 23 publications

(16 citation statements)

References 44 publications

(56 reference statements)

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“…Saccharomyces cerevisiae yeast strains with defective SCS7/FA2H are resistant to the antifungal syringomycin E (30) and the antitumor compound PM02734 (46), suggesting that 2-hydroxylated sphingolipids could influence the physical properties of some plasma membrane microdomains/lipid rafts and their internalization. This is supported by biophysical studies of membranes in reconstituted systems (47,48). In this study, we provide direct evidence that FA2H depletion modulates diffusional mobility of raft-associated lipids and co-localization of GLUT4 with lysosomes, leading to decreased GLUT4 level in a mammalian adipocyte model system.…”

Section: Discussionmentioning

confidence: 68%

Fatty Acid 2-Hydroxylase Mediates Diffusional Mobility of Raft-associated Lipids, GLUT4 Level, and Lipogenesis in 3T3-L1 Adipocytes

Guo

Zhou

Pryse

et al. 2010

Journal of Biological Chemistry

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Straight chain fatty acid ␣-oxidation increases during differentiation of 3T3-L1 adipocytes, leading to a marked accumulation of odd chain length fatty acyl moieties. Potential roles of this pathway in adipocyte differentiation and lipogenesis are unknown. Mammalian fatty acid 2-hydroxylase (FA2H) was recently identified and suggested to catalyze the initial step of straight chain fatty acid ␣-oxidation. Accordingly, we examined whether FA2H modulates adipocyte differentiation and lipogenesis in mature adipocytes. FA2H level markedly increases during differentiation of 3T3-L1 adipocytes, and small interfering RNAs against FA2H inhibit the differentiation process. In mature adipocytes, depletion of FA2H inhibits basal and insulin-stimulated glucose uptake and lipogenesis, which are partially rescued by the enzymatic product of FA2H, 2-hydroxy palmitic acid. Expression of fatty-acid synthase and SCD1 was decreased in FA2H-depleted cells, and levels of GLUT4 and insulin receptor proteins were reduced. 2-Hydroxy fatty acids are enriched in cellular sphingolipids, which are components of membrane rafts. Accelerated diffusional mobility of raft-associated lipids was shown to enhance degradation of GLUT4 and insulin receptor in adipocytes. Consistent with this, depletion of FA2H appeared to increase raft lipid mobility as it significantly accelerated the rates of fluorescence recovery after photobleaching measurements of lipid rafts labeled with Alexa 488-conjugated cholera toxin subunit B. Moreover, the enhanced recovery rates were partially reversed by treatment with 2-hydroxy palmitic acid. In conclusion, our findings document the novel role of FA2H in adipocyte lipogenesis possibly by modulation of raft fluidity and level of GLUT4.In addition to mitochondrial ␤-oxidation, fatty acids (FA) 2 can also be oxidized in peroxisomes, where they can undergo ␤-as well as ␣-oxidation. Peroxisomal ␣-oxidation produces fatty acyl moieties with one less carbon (odd chain length) without generating acetyl-CoA (1). It is well known that peroxisomal ␣-oxidation is important for catabolism of branched-chain FA and also for very long chain FA (2). Its contribution to catabolism of other long chain FA is not known, so its role in whole cell energy homeostasis remains unclear. There is evidence for up-regulation of FA ␣-oxidation during the preadipocyte to adipocyte transition as cells begin accumulating lipids. Using electrospray ionization-mass spectrometry and gas chromatography-coupled mass spectrometry, we and others demonstrated during differentiation of 3T3-L1 cells a marked increase in activity of peroxisomal FA ␣-oxidation, which was reflected in accumulation of odd chain length acyl moieties in major lipid species (3, 4). The underlying mechanisms for this change and the functions of the ␣-oxidation pathway in adipocyte differentiation and lipid metabolism in mature adipocytes have not been explored.Although straight chain FA ␣-oxidation was first reported in 1964 (5), a detailed understanding of the enzymatic pathway is sti...

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Section: Discussionmentioning

confidence: 68%

Fatty Acid 2-Hydroxylase Mediates Diffusional Mobility of Raft-associated Lipids, GLUT4 Level, and Lipogenesis in 3T3-L1 Adipocytes

Guo

Zhou

Pryse

et al. 2010

Journal of Biological Chemistry

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“…62 In addition, a very provocative investigation of the influence of chiral and racemic hydroxyalkanoic acids (with various chain lengths and hydroxyl positions) on the thermodynamic stability of dimyristoylphosphatidylcholine membranes has been conducted. 63 Both studies demonstrate the importance of chirality in affecting the detailed nature of self-assembled structures like the SAFiNs being emphasized here.…”

Section: Kinetic and Thermodynamic Aspects Of Gelation Of D-12hsa And...mentioning

confidence: 58%

Systematic modifications of alkane-based molecular gelators and the consequences to the structures and properties of their gels

Rogers

Weiss

2015

New J. Chem.

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“…Hydroxy C 18:1 fatty acids decreased the phase transition temperature of the membrane, stabilizing the liquid-crystalline state (28). Under direct comparison, the same unsaturated fatty acid had much less impact on membrane properties (28).…”

Section: Discussionmentioning

confidence: 99%

“…Cells change the fatty acid composition of the plasma membrane in response to altered environmental conditions to maintain a liquid-crystalline state (26,27). Hydroxy C 18:1 fatty acids decreased the phase transition temperature of the membrane, stabilizing the liquid-crystalline state (28). Under direct comparison, the same unsaturated fatty acid had much less impact on membrane properties (28).…”

Section: Discussionmentioning

confidence: 99%

Antifungal Hydroxy Fatty Acids Produced during Sourdough Fermentation: Microbial and Enzymatic Pathways, and Antifungal Activity in Bread

Black

Zannini

Curtis

et al. 2013

Appl Environ Microbiol

144

123

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Lactobacilli convert linoleic acid to hydroxy fatty acids; however, this conversion has not been demonstrated in food fermentations and it remains unknown whether hydroxy fatty acids produced by lactobacilli have antifungal activity. This study aimed to determine whether lactobacilli convert linoleic acid to metabolites with antifungal activity and to assess whether this conversion can be employed to delay fungal growth on bread. Aqueous and organic extracts from seven strains of lactobacilli grown in modified De Man Rogosa Sharpe medium or sourdough were assayed for antifungal activity. Lactobacillus hammesii exhibited increased antifungal activity upon the addition of linoleic acid as a substrate. Bioassay-guided fractionation attributed the antifungal activity of L. hammesii to a monohydroxy C 18:1 fatty acid. Comparison of its antifungal activity to those of other hydroxy fatty acids revealed that the monohydroxy fraction from L. hammesii and coriolic (13-hydroxy-9,11-octadecadienoic) acid were the most active, with MICs of 0.1 to 0.7 g liter ؊1 . Ricinoleic (12-hydroxy-9-octadecenoic) acid was active at a MIC of 2.4 g liter ؊1 . L. hammesii accumulated the monohydroxy C 18:1 fatty acid in sourdough to a concentration of 0.73 ؎ 0.03 g liter ؊1 (mean ؎ standard deviation). Generation of hydroxy fatty acids in sourdough also occurred through enzymatic oxidation of linoleic acid to coriolic acid. The use of 20% sourdough fermented with L. hammesii or the use of 0.15% coriolic acid in bread making increased the mold-free shelf life by 2 to 3 days or from 2 to more than 6 days, respectively. In conclusion, L. hammesii converts linoleic acid in sourdough and the resulting monohydroxy octadecenoic acid exerts antifungal activity in bread. Sourdough bread has an extended mold-free storage life compared to that of conventionally leavened products (1, 2), and metabolites from specific strains of lactobacilli contribute to the prolonged storage life of sourdough bread (3,4,5). While the fermentation microbiota of traditional sourdough is controlled by the fermentation conditions and the choice of raw materials, the industrial production of sourdough often relies on single strains of lactobacilli with defined metabolic properties (6, 7). To date, cyclic dipeptides, phenyllactic acid, acetic and propionic acids, and short-chain hydroxy fatty acids have been identified as antifungal metabolites of sourdough lactobacilli (8, 9, 10). However, these compounds are either not produced in effective quantities in sourdough fermentations or adversely affect the quality of the product when produced in active concentrations. Cyclic dipeptides, such as 2,5-diketopiperazines, are produced in quantities 1,000-fold below the MIC against molds and are accompanied by bitter or metallic flavors if present in higher quantities (11). Similarly, the amount of phenyllactic acid produced in sourdough is 1,000 times less than the required amount for activity (8,12,13). Cooperative metabolism of Lactobacillus buchneri and Lactobacillus diolivora...

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Impact of free hydroxylated and methyl-branched fatty acids on the organization of lipid membranes

Cited by 23 publications

References 44 publications

Fatty Acid 2-Hydroxylase Mediates Diffusional Mobility of Raft-associated Lipids, GLUT4 Level, and Lipogenesis in 3T3-L1 Adipocytes

Fatty Acid 2-Hydroxylase Mediates Diffusional Mobility of Raft-associated Lipids, GLUT4 Level, and Lipogenesis in 3T3-L1 Adipocytes

Systematic modifications of alkane-based molecular gelators and the consequences to the structures and properties of their gels

Antifungal Hydroxy Fatty Acids Produced during Sourdough Fermentation: Microbial and Enzymatic Pathways, and Antifungal Activity in Bread

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