Spectroscopic Examination of Punicic Acid

Ahlers, N. H. E.; Dennison, A. C.; O'Neill, L. A.

doi:10.1038/1731045a0

Cited by 23 publications

(9 citation statements)

References 4 publications

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“…Both PUA and ESA have C 18 H 30 O 2 as their molecular formula. PUA constitutes 64–83 percent of the pomegranate seed oil (PSO) [ 33 ], while ESA is at concentrations of 60–80 percent in tung and bitter gourd seed oils [ 34 ]. The molecular formula of DHA is C 28 H 33 O 2 that can be obtained directly from maternal milk or fish oil [ 35 ].…”

Section: Methodsmentioning

confidence: 99%

Modeling-Enabled Characterization of Novel NLRX1 Ligands

Hontecillas

Abedi

et al. 2015

PLoS ONE

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Nucleotide-binding domain and leucine-rich repeat containing (NLR) family are intracellular sentinels of cytosolic homeostasis that orchestrate immune and inflammatory responses in infectious and immune-mediated diseases. NLRX1 is a mitochondrial-associated NOD-like receptor involved in the modulation of immune and metabolic responses. This study utilizes molecular docking approaches to investigate the structure of NLRX1 and experimentally assesses binding to naturally occurring compounds from several natural product and lipid databases. Screening of compound libraries predicts targeting of NLRX1 by conjugated trienes, polyketides, prenol lipids, sterol lipids, and coenzyme A-containing fatty acids for activating the NLRX1 pathway. The ligands of NLRX1 were identified by docking punicic acid (PUA), eleostearic acid (ESA), and docosahexaenoic acid (DHA) to the C-terminal fragment of the human NLRX1 (cNLRX1). Their binding and that of positive control RNA to cNLRX1 were experimentally determined by surface plasmon resonance (SPR) spectroscopy. In addition, the ligand binding sites of cNLRX1 were predicted in silico and validated experimentally. Target mutagenesis studies demonstrate that mutation of 4 critical residues ASP677, PHE680, PHE681, and GLU684 to alanine resulted in diminished affinity of PUA, ESA, and DHA to NLRX1. Consistent with the regulatory actions of NLRX1 on the NF-κB pathway, treatment of bone marrow derived macrophages (BMDM)s with PUA and DHA suppressed NF-κB activity in a NLRX1 dependent mechanism. In addition, a series of pre-clinical efficacy studies were performed using a mouse model of dextran sodium sulfate (DSS)-induced colitis. Our findings showed that the regulatory function of PUA on colitis is NLRX1 dependent. Thus, we identified novel small molecules that bind to NLRX1 and exert anti-inflammatory actions.

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Section: Methodsmentioning

confidence: 99%

Modeling-Enabled Characterization of Novel NLRX1 Ligands

Hontecillas

Abedi

et al. 2015

PLoS ONE

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“…This may be in part due to the prevalence of these isomers within certain seed oils, etc. (Table 1) [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34], but also due to the extensive range of bioactivities associated with these isomers. Indeed, isomers of CLNA have been associated with anti-adipogenic and anti-carcinogenic properties, along with the modulation of immune function and inflammatory response [13,35].…”

Section: Conjugated α-Linolenic Acids (Clna)mentioning

confidence: 99%

“…Similar to pomegranate seed oil, bitter gourd seed oil and its primary CLNA isomer, known as α-eleostearic acid (c9, t11, t13), have both exhibited anti-carcinogenic properties in studies conducted using colonic (HT-29, Caco-2), mammary (MDA-wt, MDA-ER α7, MCF-7), and human leukemia cells (HL60) [64][65][66][67][68]. In these in vitro studies, exposure to α-eleostearic acid has been associated with increased cellular lipid peroxidation, inhibition of DNA synthesis, Fevillea trilobata oil 30 [17] Momordica balsamina seed oil 50 [18,19] Snake gourd seed oil 40 [20,21] Ecballium elaterium seed oil 22 [20] Milk fat ≤0.03 [22] Canadian milk fat Rapeseed oil 2.50 [23] GMO rapeseed c9, t11,t13 Tung seed oil 67.7 [16] Bitter gourd seed oil 56.2 [16] Snake gourd seed oil 30-50 [24] White mahlab 38.32 [25] Parwal seed oil 30-50 [24] Sugihiratake mushroom NS [26] Edible Japanese mushroom Parinarium species seed oil 22-69 [27,28] Prunus yedoensis seed oil 35 [28] Chrysobalanus icaco seed oil 22 [27] t9, t11, c13 Catalpa seed oil 42.3 [16] t9, t11, t13 Chemosynthesized >97 [29] Larodan Fine Chemicals, Sweden c8, t10, c12 Jacaranda seed oil 31 [30] t8, t10, c12 Pot marigold seed oil 50-62 [16] t8, t10, t12 Pot marigold seed oil 4.7 [31] c9, t11, c15 Lactobacillus plantarum AKU 1009a 67 [32] 6,9,11,15 Strains of Bifidobacterium breve 9-26 [ Chrysobalanus icaco seed oil 10 [27] Sebastiania brasiliensis seed oil 39 [44] Impatiens edgeworthii seed oil 48…”

Section: Anti-carcinogenic Propertiesmentioning

confidence: 99%

Sources and Bioactive Properties of Conjugated Dietary Fatty Acids

Hennessy

Ross

Fitzgerald

et al. 2016

Lipids

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The group of conjugated fatty acids known as conjugated linoleic acid (CLA) isomers have been extensively studied with regard to their bioactive potential in treating some of the most prominent human health malignancies. However, CLA isomers are not the only group of potentially bioactive conjugated fatty acids currently undergoing study. In this regard, isomers of conjugated α-linolenic acid, conjugated nonadecadienoic acid and conjugated eicosapentaenoic acid, to name but a few, have undergone experimental assessment. These studies have indicated many of these conjugated fatty acid isomers commonly possess anti-carcinogenic, anti-adipogenic, anti-inflammatory and immune modulating properties, a number of which will be discussed in this review. The mechanisms through which these bioactivities are mediated have not yet been fully elucidated. However, existing evidence indicates that these fatty acids may play a role in modulating the expression of several oncogenes, cell cycle regulators, and genes associated with energy metabolism. Despite such bioactive potential, interest in these conjugated fatty acids has remained low relative to the CLA isomers. This may be partly attributed to the relatively recent emergence of these fatty acids as bioactives, but also due to a lack of awareness regarding sources from which they can be produced. In this review, we will also highlight the common sources of these conjugated fatty acids, including plants, algae, microbes and chemosynthesis.

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“…Conjugated fatty acids such as linoleic and linolenic acid have recently attracted significant attention because of their health benefits in a variety of models of metabolic and chronic inflammatory diseases (6)(7)(8)(9). PUA is a conjugated fatty acid which constitutes 64-83% of the PSO and found at high concentrations in the seed of pomegranate, naturally (10)(11)(12)(13). It was shown that PUA can suppress colon cancer in rats and reduce skin carcinogenesis in mice (14,15).…”

Section: ıNtroductıonmentioning

confidence: 99%

Punicic Acid Induces Endothelium-Dependent Vasorelaxation in Rat Thoracic Aortic Rings

Yılmaz¹,

Usta²,

Taşatargil³

et al. 2015

Akd Med J

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Objective: The aim of the present study was to investigate the possible mechanism by which pomegranate seed oil causes vasodilatation in isolated thoracic aorta rings form the rat. Material and Methods: The isolated rat arteries were cut into rings and placed in tissue chambers filled with Krebs solution. results: Pomegranate seed oil produced a concentration-dependent relaxation in rings with endothelium. However, it didn't cause any relaxant effect in the absence of endothelium. L-NAME and ODQ produced a significant inhibition in the rings with endothelium. Subsequent addition of L-arginine reversed the inhibitory effects of L-NAME. However, the relaxant effect of PSO did not change with tetraethylammonium, 4-aminopyridine and glibenclamide, in rings either with or without endothelium. Additionally, the relaxant effect of PSO was not affected by indomethacin, propranolol, losartan or captopril incubation. In another set of experiments rats were anaesthetised and surgically equipped with intraperitoneal radio-transmitters to record blood pressure in vivo. PSO caused a slight decrease in systolic and diastolic blood pressure along with mildly decreased heart rate. conclusion: These comprehensive findings clearly indicate that vasorelaxation is induced by PSO via modulation of nitric oxide-guanylyl cyclase pathway.

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Spectroscopic Examination of Punicic Acid

Cited by 23 publications

References 4 publications

Modeling-Enabled Characterization of Novel NLRX1 Ligands

Modeling-Enabled Characterization of Novel NLRX1 Ligands

Sources and Bioactive Properties of Conjugated Dietary Fatty Acids

Punicic Acid Induces Endothelium-Dependent Vasorelaxation in Rat Thoracic Aortic Rings

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