scholarly journals Some Biogenetic Considerations Regarding the Marine Natural Product (−)-Mucosin

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4147 ◽  
Author(s):  
Jens M. J. Nolsøe ◽  
Marius Aursnes ◽  
Yngve H. Stenstrøm ◽  
Trond V. Hansen
Keyword(s):  
Fatty Acids ◽  
Natural Products ◽  
Arachidonic Acid ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Natural Product ◽  
Polyunsaturated Fatty Acid ◽  
Marine Natural Product ◽  
Structural Pattern ◽  
Different Origin

Recently, the identity of the marine hydrindane natural product (−)-mucosin was revised to the trans-fused structure 6, thereby providing a biogenetic puzzle that remains to be solved. We are now disseminating some of our insights with regard to the possible machinery delivering the established architecture. Aspects with regard to various modes of cyclization in terms of concerted versus stepwise processes are held up against the enzymatic apparatus known to be working on arachidonic acid (8). To provide a contrast to the tentative polyunsaturated fatty acid biogenesis, the structural pattern featured in (−)-mucosin (6) is compared to some marine hydrinane natural products of professed polyketide descent. Our appraisal points to a different origin and strengthens the hypothesis of a polyunsaturated fatty acids (PUFA) as the progenitor of (−)-mucosin (6).

Characterization of ω3 fatty acid desaturases from oomycetes and their application toward eicosapentaenoic acid production in Mortierella alpina

2021 ◽  
Author(s):  
Brian K H Mo ◽  
Akinori Ando ◽  
Ryohei Nakatsuji ◽  
Tomoyo Okuda ◽  
Yuki Takemoto ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Arachidonic Acid ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Eicosapentaenoic Acid ◽  
Polyunsaturated Fatty Acid ◽  
Desaturase Activity ◽  
Mortierella Alpina ◽  
Alternative Sources

Abstract ω3 polyunsaturated fatty acids are currently obtained mainly from fisheries, thus sustainable alternative sources such as oleaginous microorganisms are required. Here we describe the isolation, characterization, and application of three novel ω3 desaturases with ω3 polyunsaturated fatty acid-producing activity at ordinary temperatures (28 °C). First, we selected Pythium sulcatum and Plectospira myriandra after screening for oomycetes with high eicosapentaenoic acid/arachidonic acid ratios and isolated the genes psulω3 and pmd17, respectively, which encode ω3 desaturases. Subsequent characterization showed that PSULω3 exhibited ω3 desaturase activity on both C18 and C20 ω6 polyunsaturated fatty acids while PMD17 exhibited ω3 desaturase activity exclusively on C20 ω6 polyunsaturated fatty acids. Expression of psulω3 and pmd17 in the arachidonic acid-producer Mortierella alpina resulted in transformants that produced eicosapentaenoic acid/total fatty acid values of 38% and 40%, respectively, at ordinary temperatures. These ω3 desaturases should facilitate the construction of sustainable ω3 polyunsaturated fatty acid sources.

Maternal polyunsaturated fatty acids and risk for autism spectrum disorder in the MARBLES high-risk study

Autism ◽  
2020 ◽  
Vol 24 (5) ◽  
pp. 1191-1200 ◽  
Author(s):  
Yunru Huang ◽  
Ana-Maria Iosif ◽  
Robin L Hansen ◽  
Rebecca J Schmidt
Keyword(s):  
Autism Spectrum Disorder ◽  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Polyunsaturated Fatty Acid ◽  
Autism Spectrum ◽  
Spectrum Disorder ◽  
Fatty Acid Intake ◽  
Third Trimester ◽  
Acid Intake

Prior research studies suggest that maternal polyunsaturated fatty acids could have protective effects on neurodevelopmental outcomes. The objective of this study was to examine associations between maternal polyunsaturated fatty acid intake during pregnancy and risk for autism spectrum disorder and other non-typical development in a prospective cohort. Eligible women already had a child with autism spectrum disorder and were planning a pregnancy or were pregnant with another child. Children were clinically assessed longitudinally and diagnosed at 36 months. Maternal polyunsaturated fatty acid intake during pregnancy was estimated using food frequency questionnaires. Maternal third-trimester plasma polyunsaturated fatty acid concentration was measured by gas chromatography. In all, 258 mother–child pairs were included. Mothers consuming more total omega-3 in the second half of pregnancy were 40% less likely to have children with autism spectrum disorder (relative risk = 0.6, 95% confidence interval: 0.3–0.98). No significant associations were observed between maternal third-trimester plasma polyunsaturated fatty acid subtype concentrations and risk of autism spectrum disorder. However, higher plasma eicosapentaenoic acid and docosahexaenoic acid concentrations were associated with lower non-typical development risk (relative risk ranging from 0.47 to 0.88). This study provides suggestive evidence of associations between risk of autism spectrum disorder in the children and maternal omega-3 intake in late pregnancy but not with third-trimester plasma polyunsaturated fatty acids. Further research is needed to evaluate these potential relationships. Lay abstract Prior studies suggest that maternal polyunsaturated fatty acids intake during pregnancy may have protective effects on autism spectrum disorder in their children. However, they did not examine detailed timing of maternal polyunsaturated fatty acid intake during pregnancy, nor did they evaluate plasma concentrations. This study investigates whether maternal polyunsaturated fatty acids in defined time windows of pregnancy, assessed by both questionnaires and biomarkers, are associated with risk of autism spectrum disorder and other non-typical development in the children. Food frequency questionnaires were used to estimate maternal polyunsaturated fatty acid intake during the first and second half of pregnancy. Gas chromatography measured maternal plasma polyunsaturated fatty acid concentrations in the third trimester. In all, 258 mother–child pairs from a prospective cohort were included. All mothers already had a child with autism spectrum disorder and were planning a pregnancy or pregnant with another child. Children were clinically assessed longitudinally and diagnosed at 36 months. For polyunsaturated fatty acid intake from questionnaires, we only found mothers consuming more omega-3 in the second half of pregnancy were 40% less likely to have children with autism spectrum disorder. For polyunsaturated fatty acid concentrations in the third-trimester plasma, we did not observe any statistical significance in relation to the risk of autism spectrum disorder. However, our study confirmed associations from previous studies between higher maternal docosahexaenoic acid and eicosapentaenoic acid plasma concentrations in the late pregnancy and reduced risk for non-typical development. This study markedly advanced understandings of whether and when maternal polyunsaturated fatty acid intake influences risk for autism spectrum disorder and sets the stage for prevention at the behavioral and educational level.

scholarly journals Dietary fat and the diabetic state alter insulin binding and the fatty acyl composition of the adipocyte plasma membrane

1988 ◽  
Vol 253 (2) ◽  
pp. 417-424 ◽  
Author(s):  
C J Field ◽  
E A Ryan ◽  
A B Thomson ◽  
M T Clandinin
Keyword(s):  
Fatty Acids ◽  
Arachidonic Acid ◽  
Plasma Membrane ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Insulin Binding ◽  
Fatty Acyl ◽  
Membrane Composition ◽  
Membrane Phospholipids ◽  
Diabetic State

Control and diabetic rats were fed on semi-purified high-fat diets providing a polyunsaturated/saturated fatty acid ratio (P/S) of 1.0 or 0.25, to examine the effect of diet on the fatty acid composition of major phospholipids of the adipocyte plasma membrane. Feeding the high-P/S diet (P/S = 1.0) compared with the low-P/S diet (P/S = 0.25) increased the content of polyunsaturated fatty acids in membrane phospholipids in both control and diabetic animals. The diabetic state decreased the content of polyunsaturated fatty acids, particularly arachidonic acid, in adipocyte membrane phospholipids. The decrease in arachidonic acid in membrane phospholipids of diabetic animals tended to be normalized to within the control values when high-P/S diets were given. For control animals, altered plasma-membrane composition was associated with change in insulin binding, suggesting that change in plasma-membrane composition may have physiological consequences for insulin-stimulated functions in the adipocyte.

scholarly journals Diet Supplementation in ω3 Polyunsaturated Fatty Acid Favors an Anti-Inflammatory Basal Environment in Mouse Adipose Tissue

Nutrients ◽  
2019 ◽  
Vol 11 (2) ◽  
pp. 438 ◽  
Author(s):  
Cecilia Colson ◽  
Rayane Ghandour ◽  
Océane Dufies ◽  
Samah Rekima ◽  
Agnès Loubat ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Adipose Tissue ◽  
Fatty Acid ◽  
Inflammatory Response ◽  
Polyunsaturated Fatty Acids ◽  
Polyunsaturated Fatty Acid ◽  
Inflammatory Cytokine ◽  
M2 Macrophage ◽  
Anti Inflammatory ◽  
Diet Supplementation

Oxylipins are metabolized from dietary ω3 and ω6 polyunsaturated fatty acids and are involved in an inflammatory response. Adipose tissue inflammatory background is a key factor of metabolic disorders and it is accepted that dietary fatty acids, in terms of quality and quantity, modulate oxylipin synthesis in this tissue. Moreover, it has been reported that diet supplementation in ω3 polyunsaturated fatty acids resolves some inflammatory situations. Thus, it is crucial to assess the influence of dietary polyunsaturated fatty acids on oxylipin synthesis and their impact on adipose tissue inflammation. To this end, mice fed an ω6- or ω3-enriched standard diet (ω6/ω3 ratio of 30 and 3.75, respectively) were analyzed for inflammatory phenotype and adipose tissue oxylipin content. Diet enrichment with an ω3 polyunsaturated fatty acid induced an increase in the oxylipins derived from ω6 linoleic acid, ω3 eicosapentaenoic, and ω3 docosahexaenoic acids in brown and white adipose tissues. Among these, the level of pro-resolving mediator intermediates, as well as anti-inflammatory metabolites, were augmented. Concomitantly, expressions of M2 macrophage markers were increased without affecting inflammatory cytokine contents. In vitro, these metabolites did not activate macrophages but participated in macrophage polarization by inflammatory stimuli. In conclusion, we demonstrated that an ω3-enriched diet, in non-obesogenic non-inflammatory conditions, induced synthesis of oxylipins which were involved in an anti-inflammatory response as well as enhancement of the M2 macrophage molecular signature, without affecting inflammatory cytokine secretion.

scholarly journals Resistance of Biomphalaria alexandrina to Schistosoma mansoni and Bulinus truncatus to Schistosoma haematobium Correlates with Unsaturated Fatty Acid Levels in the Snail Soft Tissue

2020 ◽  
Vol 2020 ◽  
pp. 1-14
Author(s):  
Marian Elias ◽  
Rasha S. Hanafi ◽  
Samia El-Bardicy ◽  
Ebtisam A. Hafez ◽  
Rashika El Ridi
Keyword(s):  
Fatty Acids ◽  
Arachidonic Acid ◽  
Fatty Acid ◽  
Soft Tissue ◽  
Polyunsaturated Fatty Acids ◽  
Schistosoma Mansoni ◽  
Schistosome Infection ◽  
Bulinus Truncatus ◽  
Biomphalaria Alexandrina ◽  
Arachidonic Acids

Only a fraction of the Biomphalaria and Bulinus snail community shows patent infection with schistosomes despite continuous exposure to the parasite, indicating that a substantial proportion of snails may resist infection. Accordingly, exterminating the schistosome intermediate snail hosts in transmission foci in habitats that may extend to kilometres is cost-prohibitive and damaging to the ecological equilibrium and quality of water and may be superfluous. It may be more cost effective with risk less ecological damage to focus on discovering the parameters governing snail susceptibility and resistance to schistosome infection. Therefore, laboratory bred Biomphalaria alexandrina and Bulinus truncatus snails were exposed to miracidia of laboratory-maintained Schistosoma mansoni and S. haematobium, respectively. Snails were examined for presence or lack of infection association with soft tissue and hemolymph content of proteins, cholesterol, and triglycerides, evaluated using standard biochemical techniques and palmitic, oleic, linoleic, and arachidonic acid, assayed by ultraperformance liquid chromatography-tandem mass spectrometry. Successful schistosome infection of B. alexandrina and B. truncatus consistently and reproducibly correlated with snails showing highly significant (up to P < 0.0001 ) decrease in soft tissue and hemolymph content of the monounsaturated fatty acid, oleic acid, and the polyunsaturated fatty acids, linoleic, and arachidonic acids as compared to naïve snails. Snails that resisted twice infection had soft tissue content of oleic, linoleic, and arachidonic acid similar to naïve counterparts. High levels of soft tissue and hemolymph oleic, linoleic, and arachidonic acid content appear to interfere with schistosome development in snails. Diet manipulation directed to eliciting excessive increase of polyunsaturated fatty acids in snails may protect them from infection and interrupt disease transmission in a simple and effective manner.

Selective esterification to produce microalgal biodiesel and enrich polyunsaturated fatty acid using zeolite as a catalyst

RSC Advances ◽  
2015 ◽  
Vol 5 (103) ◽  
pp. 84894-84900 ◽  
Author(s):  
Tao Dong ◽  
Xiaochen Yu ◽  
Chao Miao ◽  
Barbara Rasco ◽  
Manuel Garcia-Pérez ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Polyunsaturated Fatty Acid ◽  
Integrated Process ◽  
Selective Catalyst ◽  
Selective Esterification ◽  
Microalgal Biodiesel

A novel integrated process to produce microalgal biodiesel and simultaneously enrich high-value polyunsaturated fatty acids (PUFA) using selective catalyst.

Polyunsaturated fatty acid-specific elongation enzymes

2000 ◽  
Vol 28 (6) ◽  
pp. 658-660 ◽  
Author(s):  
T. Das ◽  
J. M. Thurmond ◽  
E. Bobik ◽  
A. E. Leonard ◽  
J. M. Parker-Barnes ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Caenorhabditis Elegans ◽  
Polyunsaturated Fatty Acids ◽  
Polyunsaturated Fatty Acid ◽  
Mortierella Alpina ◽  
Novel Gene ◽  
Encoded Proteins ◽  
Specific Elongation

We have isolated a novel gene (GLELO) from Mortierella alpina and its homologue (CEELO1) from Caenorhabditis elegans and demonstrate the involvement of their encoded proteins in the elongation of C18 polyunsaturated fatty acids.

scholarly journals Differential effects of n-3 and n-6 polyunsaturated fatty acids on BRCA1 and BRCA2 gene expression in breast cell lines

2002 ◽  
Vol 87 (4) ◽  
pp. 281-289 ◽  
Author(s):  
Dominique J. Bernard-Gallon ◽  
Cécile Vissac-Sabatier ◽  
David Antoine-Vincent ◽  
Pascale G. Rio ◽  
Jean-Claude Maurizis ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Cell Lines ◽  
Polyunsaturated Fatty Acid ◽  
Breast Tumour ◽  
Current Evidence ◽  
Tumour Suppressor Genes ◽  
Dependent Manner ◽  
Breast Cell Lines

Current evidence strongly supports a role for the breast tumour suppressor genes, BRCA1 and BRCA2, in both normal development and carcinogenesis. In vitro observations reported that BRCA1 and BRCA2 are expressed in a cell cycle-dependent manner. Interestingly, differences in the actions of n-3 and n-6 polyunsaturated fatty acids have been observed: while the n-3 polyunsaturated fatty acids have been described to reduce pathological cell growth, the n-6 polyunsaturated fatty acids have been found to induce tumour proliferation. Here, we examined the expression of BRCA1 and BRCA2 in breast cell lines after treatment with polyunsaturated fatty acids. Real-time quantitative polymerase chain reaction determinations conclusively demonstrated increases in BRCA1 and BRCA2 mRNA expressions in MCF7 and MDA-MB 231 tumour cell lines after treatment with n-3 polyunsaturated fatty acids (eicosapentaenoic acid and docosahexaenoic acid), but no variation was noticed with the n-6 polyunsaturated fatty acid (arachidonic acid). On the other hand, no variation of the expression of BRCA1 and BRCA2 mRNA was detected in MCF10a normal breast cell line treated by polyunsaturated fatty acids. The level of BRCA1 and BRCA2 proteins quantified by affinity chromatography remained unchanged in tumour (MCF7, MDA-MB 231) and normal (MCF10a) breast cell lines. We suggest the presence of a possible transcriptional or post-transcriptional regulation of BRCA1 and BRCA2 after n-3 polyunsaturated fatty acid treatment in breast tumour cells.

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