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Biomimetic nitration of conjugated linoleic acid: formation and characterization of naturally occurring conjugated nitrodienes.

ABSTRACT: Nitro-conjugated linoleic acids (NO2-cLA), endogenous nitrodiene lipids which act as inflammatory signaling mediators, were isolated and single isomers purified from the biomimetic acidic nitration products of conjugated linoleic acid (CLA). Structures were elucidated by means of detailed NMR and HPLC-MS/MS spectroscopic analysis and the relative double bond configurations assigned. Additional synthetic methods produced useful quantities and similar isomeric distributions of these unusual and reactive compounds for biological studies and isotopic standards, and the potential conversion of nitro-linoleic to nitro-conjugated linoleic acids was explored via a facile base-catalyzed isomerization. This represents one of the few descriptions of naturally occurring conjugated nitro dienes (in particular, 1-nitro 1,3-diene), an unusual and highly reactive motif with few biological examples extant.

SUBMITTER: Woodcock SR

PROVIDER: S-EPMC4061743 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Biomimetic nitration of conjugated linoleic acid: formation and characterization of naturally occurring conjugated nitrodienes.

Woodcock Steven R SR Salvatore Sonia R SR Bonacci Gustavo G Schopfer Francisco J FJ Freeman Bruce A BA

The Journal of organic chemistry 20131219 1

Nitro-conjugated linoleic acids (NO2-cLA), endogenous nitrodiene lipids which act as inflammatory signaling mediators, were isolated and single isomers purified from the biomimetic acidic nitration products of conjugated linoleic acid (CLA). Structures were elucidated by means of detailed NMR and HPLC-MS/MS spectroscopic analysis and the relative double bond configurations assigned. Additional synthetic methods produced useful quantities and similar isomeric distributions of these unusual and re ...[more]

PMID: 24350701

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Project description:Conjugated linoleic acids (CLAs) and conjugated linolenic acids (CLNAs) have gained significant attention due to their anticarcinogenic and lipid/energy metabolism-modulatory effects. However, their concentration in foodstuffs is insufficient for any therapeutic application to be implemented. From a biotechnological standpoint, microbial production of these conjugated fatty acids (CFAs) has been explored as an alternative, and strains of the genera Propionibacterium, Lactobacillus, and Bifidobacterium have shown promising producing capacities. Current screening research works are generally based on direct analytical determination of production capacity (e.g., trial and error), representing an important bottleneck in these studies. This review aims to summarize the available information regarding identified genes and proteins involved in CLA/CLNA production by these groups of bacteria and, consequently, the possible enzymatic reactions behind such metabolic processes. Linoleate isomerase (LAI) was the first enzyme to be described to be involved in the microbiological transformation of linoleic acids (LAs) and linolenic acids (LNAs) into CFA isomers. Thus, the availability of lai gene sequences has allowed the development of genetic screening tools. Nevertheless, several studies have reported that LAIs have significant homology with myosin-cross-reactive antigen (MCRA) proteins, which are involved in the synthesis of hydroxy fatty acids, as shown by hydratase activity. Furthermore, it has been suggested that CLA and/or CLNA production results from a stress response performed by the activation of more than one gene in a multiple-step reaction. Studies on CFA biochemical pathways are essential to understand and characterize the metabolic mechanism behind this process, unraveling all the gene products that may be involved. As some of these bacteria have shown modulation of lipid metabolism in vivo, further research to be focused on this topic may help us to understand the role of the gut microbiota in human health.

Project description:BackgroundUltraviolet B (UVB) has been reported to prevent bone loss by promoting the synthesis of vitamin D. However, UVB can also enhance osteoclastic differentiation, inhibit osteogenic differentiation, and cause oxidative damage. The present study aimed to analyze the osteoprotective effects of UVB and conjugated linoleic acid (CLA) in rats with ovariectomy-induced osteoporosis, and to determine the interactions between UVB and CLA and their effects on bone mesenchymal stem cells (BMSCs) and bone marrow mononuclear cells (BMMCs).MethodsIn vitro, the distance of UVB irradiation and the dose of CLA were selected by immunofluorescence assays and Cytotoxicity assay. BMSCs and BMMCs were detected by immunohistochemical and immunofluorescence assays. In vivo, three-month-old female Sprague-Dawley rats that had undergone ovariectomy were treated with UVB and CLA. After 8 weeks of therapy, the femurs of the rats were examined by micro-computed tomography (CT) and immunohistochemical detection to assess the therapeutic efficacy.ResultsThe least inhibitive UVB distance and dosage of CLA were selected for the in vivo experiments. CLA effectively weakened the osteogenic inhibitory effect of UVB (72 cm), significantly improved the activity of alkaline phosphatase (ALP), promoted the formation of mineralized nodules, and alleviated the oxidative damage induced by UVB. CLA also effectively weakened the osteoclast-promoting effect of UVB (72 cm), inhibited osteoclast formation, and inhibited the inflammatory damage to BMMCs caused by UVB (72 cm) irradiation. Micro-CT results showed that UVB irradiation could promote bone formation in ovariectomized Sprague-Dawley rats, while CLA could significantly promote bone regeneration. Immunofluorescence assays results showed that CLA alleviated UVB-induced oxidative damage to osteoblasts. The ROS detection results demonstrated that CLA effectively alleviated UVB-induced oxidative damage to BMSCs. Furthermore, Immunohistochemical assays showed that UVB and CLA treatment increased bone density, inhibited osteolytic osteolysis, and enhanced osteogenic activity.ConclusionsCLA can effectively weaken osteoclast promotion, osteogenic inhibition, and oxidative damage caused by UVB. Combination treatment of UVB and CLA exerts an osteoprotective effect on ovariectomized osteoporotic rats and stimulates osteogenesis. The molecular mechanism of this interaction requires further investigation.

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Biomimetic nitration of conjugated linoleic acid: formation and characterization of naturally occurring conjugated nitrodienes.

Publications

Biomimetic nitration of conjugated linoleic acid: formation and characterization of naturally occurring conjugated nitrodienes.

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