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The SREBP-2 transcription factor is mainly activated by low cellular cholesterol levels. However, other factors may also cause SREBP-2 activation. We have previously demonstrated activation of SREBP-2 by the polyunsaturated fatty acid docosahexaenoic acid (DHA) in SW620 colon cancer cells. Despite activation of SREBP-2, only a few target genes were induced and cholesterol biosynthesis was reduced...
Four new fatty acid esters have been isolated from Feces Trogopterus. Their structures were determined by spectroscopic and chemical methods to be bis(7-hydroxyheptyl) icosanedioate (1), bis(7-hydroxyheptyl) heptadecanedioate (2), bis(7-hydroxyheptyl) decanedioate (3), and bis(7-hydroxyheptyl) octanedioate (4). In the anticoagulative assay, compounds 3 and 4 had significant antithrombin activity.
First studies on the occurrence of nitrated fatty acids in plasma of healthy subjects revealed basal concentrations of 600 nM for free/nonesterified nitro-oleic acid (NO2-OA) as measured by liquid chromatography tandem mass spectrometry (LC–MS/MS). We recently showed by a gas chromatography tandem mass spectrometry (GC–MS/MS) method the physiological occurrence of two isomers, i.e., 9-NO2-OA and 10-NO...
Gangliosides are a large family of glycosphingolipids that are abundant in the brain, and have been shown to affect neuronal plasticity during development, adulthood, and aging. We developed a fast, efficient, and sensitive liquid chromatography–mass spectrometry method to quantify eight different classes of gangliosides (GM1, GM2, GM3, GD3, GD1a, GD1b, GT1b, GQ1b) in the brains of 2-day-old and 80-day-old...
Lipase-catalyzed transesterification of flaxseed oil with cinnamic acid (CA) or ferulic acid (FA) using an immobilized lipase from Candida antarctica (E.C. 3.1.1.3) was conducted to evaluate whether the lipophilized products provided enhanced antioxidant activity in the oil. Lipase-catalyzed transesterification of flaxseed oil with CA or FA produced a variety of lipophilized products (identified using...
Imaging mass spectrometry (IMS) has been developed as a method for determining and visualizing the distribution of proteins and lipids across sections of dissected tissue. Although lipids play an important role in mammal development, their detailed distributions have not been analyzed by conventional methods. In this study, we tried to determine and visualize lysophosphatidylcholine (LysoPtdCho) and...
Rhizochalin [(2R,3R,26R,27R)-2,27-diamino-3-hydroxy-26-[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy]octacosan-11-one], an antimicrobial and cytotoxic marine two-headed sphingolipid-like natural product, isolated from the sponge Rhizochalina incrustata, and some related compounds were studied as anticarcinogenic and proapoptotic agents. The corresponding effects were...
Tocotrienols are powerful chain breaking antioxidant. Moreover, they are now known to exhibit various non-antioxidant properties such as anti-cancer, neuroprotective and hypocholesterolemic functions. This study was undertaken to investigate the anti-inflammatory effects of tocotrienol-rich fraction (TRF) and individual tocotrienol isoforms namely δ-, γ-, and α-tocotrienol on lipopolysaccharide-stimulated...
This study reports on the results of repeated gavages and dietary feeding of lutein dispersed either in phospholipids or fatty acid micelles or vegetable oils and the effects on lutein bioavailability and antioxidant enzymes in rats. For the gavage study, rats (n = 5/group) were intubated with lutein solubilized either in oleic acid (OLA, 18:1n-9) or linoleic acid (LNA, 18:2n-6) or phosphatidylcholine...
As meat is a rich source of the omega-3 fatty acid docosapentaenoic acid (DPA) and Australians consume six times more meat than fish, investigation of the potential health benefit of DPA is warranted. The aims were to compare the effects of seal oil supplementation with fish oil, on measures of plasma lipids and blood pressure in hypertriglyceridaemic subjects. Forty-eight volunteers were recruited...
Preclinical and clinical studies demonstrate that the omega-3 fatty acids docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) as a triacylglycerol (TAG) or an ethyl ester are protective against cardiovascular disease. Both have significant TAG-lowering effects. We developed a concentrated ethyl ester of DHA (MATK-90, 900 mg/g) using microalgae as its source. This study evaluated the effects...
A kinetic study of the prooxidant effect of α-tocopherol was performed. The rates of allylic hydrogen abstraction from various unsaturated fatty acid esters (ethyl stearate 1, ethyl oleate 2, ethyl linoleate 3, ethyl linolenate 4, and ethyl arachidonate 5) by α-tocopheroxyl radical in toluene were determined, using a double-mixing stopped-flow spectrophotometer. The second-order rate constants (k...
Standard methods to quantify the activity of triacylglycerol (TAG) synthesizing enzymes DGAT and PDAT (TAG-SE) require a sensitive but rather arduous laboratory assay based on radio-labeled substrates. Here we describe two straightforward methods to detect TAG production in baker’s yeast Saccharomyces cerevisiae. First we demonstrate that a quadruple knockout yeast strain deficient in storage lipids...
Ezetimibe inhibits cholesterol absorption in the intestine. Sphingomyelin has strong interactions with cholesterol. We investigated the effects of ezetimibe on Sphingomyelinase (SMase) expression in intestine and liver. After feeding rats with ezetimibe (5 mg/kg per day) for 14 days, acid SMase activities in the liver and in the proximal part of small intestine were reduced by 34 and 25%, respectively...
Cyclooxygenase-2 (COX-2) is intimately involved in symptoms of arthritis while dietary n-3 polyunsaturated fatty acids (PUFA) are thought to be beneficial. In these experiments, using both bovine and human in vitro systems that mimic features of arthritis, we show that the n-3 PUFA eicosapentaenoic acid (EPA) is able to reduce mRNA and protein levels of COX-2. Activity, as assessed through prostaglandin...
Statins directly inhibit 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGR) activity, while γ-tocotrienol, an isoform of vitamin E, enhances the degradation and reduces cellular levels of HMGR in various tumor cell lines. Since treatment with statins or γ-tocotrienol alone induced a dose-responsive inhibition, whereas combined treatment with subeffective doses of these agents resulted in a synergistic...
The first total syntheses of the naturally occurring acetylenic fatty acids—6-heptadecynoic acid (59% overall yield) and 6-icosynoic acid (34% overall yield)—was accomplished in four steps. Using the same synthetic sequence the naturally occurring fatty acids (6Z)-heptadecenoic acid (46% overall yield) and (6Z)-icosenoic acid (27% overall yield) were also synthesized. The Δ6 acetylenic fatty acids...
In animals and plants, fatty acids with at least three double bonds can be oxidized to prostaglandin-like compounds via enzymatic and non-enzymatic pathways. The most common fatty acid precursor in mammals is arachidonic acid (C20:4) (AA) which can be converted through the cyclooxygenase pathway to a series of prostaglandins (PG). Non-enzymatic cyclization of arachidonate yields a series of isoprostanes...
Octacosa-10,19-dien-1-ol is a newly synthesized long-chain alcohol, an unsaturated analogue of 1-octacosanol, the major component of policosanol, the purified natural mixture of different higher aliphatic alcohols obtained from sugarcane wax. Our efficient synthetic protocol (five steps with 50% overall yield) is well suited for gram scale preparations and a rapid generation of analogues with different...
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