Linoleic acid-derived 13-hydroxyoctadecadienoic acid is absorbed and incorporated into rat tissues

Zhang, Z.; Emami, Shiva; Hennebelle, Marie; Morgan, Rhianna K.; Lerno, Larry; Slupsky, Carolyn M.; Lein, Pamela J.; Taha, Ameer Y.

doi:10.1016/j.bbalip.2020.158870

Cited by 11 publications

(7 citation statements)

References 58 publications

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“…Despite being a major part of the diet [ 50 ], LA is not found in appreciable levels in the brain (<2% of total fatty acids) because it is mostly (~60%) beta-oxidized upon entry [ 80 ]. Thus, we questioned whether a portion of the LA that enters the brain is converted into OXLAMs, having established that OXLAMs are unlikely to cross the blood brain barrier in adult rats [ 81 ].…”

Section: Bioactive Lipids Mediators Derived From Pufasmentioning

confidence: 99%

Polyunsaturated fatty acids and fatty acid-derived lipid mediators: Recent advances in the understanding of their biosynthesis, structures, and functions

Dyall

Balas

Bazán

et al. 2022

Progress in Lipid Research

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288

163

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Section: Bioactive Lipids Mediators Derived From Pufasmentioning

confidence: 99%

Polyunsaturated fatty acids and fatty acid-derived lipid mediators: Recent advances in the understanding of their biosynthesis, structures, and functions

Dyall

Balas

Bazán

et al. 2022

Progress in Lipid Research

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288

163

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“…13-HOD ( 17 ) was reported to serve as a bioactive lipid mediator that regulates multiple signaling processes in vivo . However, this compound was very difficult to produce by using fatty acid double bond hydratases or P450 monooxygenases.…”

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic Cascade Conversion of Linoleic Acid into a Secondary Fatty Alcohol Using a Combination of 13S-Lipoxygenase, Chemical Reduction, and a Photo-Activated Decarboxylase

Cha

Lee

et al. 2021

ACS Sustainable Chem. Eng.

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Linoleic acid serves as a starting material in the production of various oleochemicals. Here, we have investigated the transformation of linoleic acid into 13S-hydroxy-(9Z,11E)-octadecadienoic acid (13-HOD) (17) and 6S-hydroxy-(7E,9Z)heptadecadiene (6-HHD) (18) by using 13S-lipoxygenase from Pseudomonas aeruginosa (Pa-LOX) and photo-activated decarboxylase from Chlorella variabilis NC64A (Cv-FAP). Remarkably, the recombinant Escherichia coli expressing Pa-LOX was able to produce 13S-hydroperoxy-(9Z,11E)-octadecadienoic acid ( 16) at a maximum rate of 850 μmol/g dry cells/min. This allowed the accumulation of 13-HOD (17) to 161 mM (48 g/L) concentration from 200 mM linoleic acid in the reaction medium within 3.5 h. We have also demonstrated that the fatty acids, including CC bonds in cis-and trans-forms [e.g., 13-HOD (17)], were subjected to photo-activated decarboxylation by Cv-FAP. Ultimately, the secondary fatty alcohol [i.e., 6-HHD ( 18)] was produced from linoleic acid through the chemo/enzymatic cascade transformation, consisting of dioxygenation of linoleic acid by intracellular Pa-LOX and reduction of the hydroperoxy fatty acid (16) by Tris(2-carboxyethyl) phosphine or cysteine. Moreover, the photoactivated decarboxylation of the hydroxy fatty acid (17) by intracellular Cv-FAP achieved a conversion of ca. 74% in a one-pot process. This study will contribute to the valorization of γ-linolenic and arachidonic acid, as well as linoleic acid, which are the substrates of Pa-LOX.

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“…8−10 A recent study in rats showed that deuterated 13-hydroxyoctadecadienoic acid (13-HODE), an oxylipin found in high abundance in oils and bovine milk, 11,12 is absorbed and incorporated into tissues. 13 Ingested oxylipins from thermally oxidized corn oil have recently been shown to alter cerebrum and cerebellum fatty acid composition and to induce liver mitochondrial dysfunction in mice, 14,15 suggesting in vivo bioactivity.…”

Section: Introductionmentioning

confidence: 99%

“…Ingested oxylipins are bioavailable in both humans and rats with absorption efficiencies ranging between 4.5% to 38.7% in humans and 14.8% in rats depending on the type of oxylipin (e.g., hydroperoxide, hydroxy or dihydroxy fatty acid). − A recent study in rats showed that deuterated 13-hydroxyoctadecadienoic acid (13-HODE), an oxylipin found in high abundance in oils and bovine milk, , is absorbed and incorporated into tissues . Ingested oxylipins from thermally oxidized corn oil have recently been shown to alter cerebrum and cerebellum fatty acid composition and to induce liver mitochondrial dysfunction in mice, , suggesting in vivo bioactivity.…”

Section: Introductionmentioning

confidence: 99%

Effects of Potato Processing and Frying on Oxylipin Concentrations

Zhang

Hennebelle

Emami

et al. 2021

ACS Food Sci. Technol.

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Potatoes undergo several processing steps including blanching and par-frying to form frozen French fries, which are typically fried in oil subjected to multiple frying cycles. The present study aimed to comprehensively measure the effects of potato processing (i.e., blanching, par-frying, deep frying and repeated frying cycles) on the concentration of primary oxidized fatty acids known as oxylipins in potatoes and the oil used to fry them. Compared to raw peeled potatoes, blanching decreased linoleic acid (LA)-derived epoxides and diols and increased α-linolenic acid-derived hydroxides. Par-frying and one cycle of deep frying reduced several hydroxylated and ketone metabolites of LA or ALA, and increased LA-derived diols relative to raw potatoes. Repeated frying cycles increased several LA- and ALA-derived oxylipins in oil. Some but not all of these changes were reflected in potato French fries heated in the same oil. It is concluded that distinct oxylipin profiles are observed when oil and potatoes are subjected to different processing conditions.

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Linoleic acid-derived 13-hydroxyoctadecadienoic acid is absorbed and incorporated into rat tissues

Cited by 11 publications

References 58 publications

Polyunsaturated fatty acids and fatty acid-derived lipid mediators: Recent advances in the understanding of their biosynthesis, structures, and functions

Polyunsaturated fatty acids and fatty acid-derived lipid mediators: Recent advances in the understanding of their biosynthesis, structures, and functions

Chemoenzymatic Cascade Conversion of Linoleic Acid into a Secondary Fatty Alcohol Using a Combination of 13S-Lipoxygenase, Chemical Reduction, and a Photo-Activated Decarboxylase

Effects of Potato Processing and Frying on Oxylipin Concentrations

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