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Robert C. Murphy - One of the best experts on this subject based on the ideXlab platform.
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low concentration ozone reacts with plasmalogen Glycerophosphoethanolamine lipids in lung surfactant
Chemical Research in Toxicology, 2010Co-Authors: Kelly M Wynalda, Robert C. MurphyAbstract:Ozone is a common environmental toxicant to which individuals are exposed to on a daily basis. While biochemical end points such as increased mortality, decrements in pulmonary function, and initiation of inflammatory processes are known, little is actually understood regarding the chemical mechanisms underlying changes in pulmonary health, especially for low concentrations of ozone. This study was undertaken to investigate ozone-induced oxidation of endogenous lipids that are potentially exposed to environmental ozone within lung, specifically focusing on plasmalogen glycerophospholipids present in pulmonary surfactant. Sensitive liquid chromatography−mass spectrometry methods were developed to follow oxidation of diacyl and plasmalogen phosphatidylethanolamine (PE) phospholipids and to identify and quantitate products generated by ozonolysis. Using a unilamellar vesicle system containing a 1:1 molar mixture of 1-O-octadec-1′-enyl-2-octadecenoyl-PE and 1,2-dihexadecanoyl-PC, these studies revealed that t...
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Stable isotope labeled 4-(dimethylamino)benzoic acid derivatives of Glycerophosphoethanolamine lipids.
Analytical Chemistry, 2009Co-Authors: Karin A. Zemski Berry, William W. Turner, Michael S. Vannieuwenhze, Robert C. MurphyAbstract:A set of four (D0, D4, D6, and D10) deuterium enriched 4-(dimethylamino)benzoic acid (DMABA) N-hydroxysuccinimide (NHS) ester reagents was developed that react with the primary amine group of Glycerophosphoethanolamine (PE) lipids to create derivatives where all subclasses of DMABA labeled PE are detected by a common precursor ion scan. The positive ion collision induced dissociation data from (D0, D4, D6, and D10)-DMABA labeled PE standards indicated that a precursor ion scan of m/z 191.1, 195.1, 197.1, and 201.1 could be used to selectively detect (D0, D4, D6, and D10)-DMABA modified PE, respectively, in a complex biological mixture. The PE lipids from a time course (0, 30, 60, and 300 min) of 2,2′-azobis-(2-amidinopropane) hydrochloride (AAPH) treatment of liposomes made of RAW 264.7 cell phospholipids were each labeled with the D0-, D4-, D10-, and D6-DMABA NHS ester reagents, respectively. The DMABA derivatives revealed loss of endogenous PE lipids and an increase in oxidized PE lipid throughout the t...
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FcϵRI and Thy-1 domains have unique protein and lipid compositions
Journal of Lipid Research, 2007Co-Authors: Zurab Surviladze, Robert C. Murphy, Kathleen A. Harrison, Bridget S. WilsonAbstract:Receptor activation leads to the dynamic remodeling of the plasma membrane. Previous work using immunoelectron microscopy showed that aggregated high-affinity receptor for immunoglobulin E (FceRI) and aggregated Thy-1, a glycerophosphoinositol (GPI)-anchored protein, have distinct membrane distributions. We now report lipidomics analysis of FceRI- and Thy-1-enriched vesicles obtained by magnetic bead isolation in the absence of detergent. Protein analyses show that FceRI domains are enriched in receptors and associated signaling molecules, whereas Thy-1 domains are devoid of FceRI subunits. Positive and negative ion electrospray mass spectrometry demonstrated that both domains retained a complex mixture of phospholipid classes and molecular species, predominantly glycerophosphocholine, Glycerophosphoethanolamine (GPE), and sphingomyelin as well as glycerophosphoserine and GPI lipids. Analysis of total acyl groups showed that
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Characterization of acrolein-Glycerophosphoethanolamine lipid adducts using electrospray mass spectrometry.
Chemical Research in Toxicology, 2007Co-Authors: Karin A. Zemski Berry, Robert C. MurphyAbstract:Acrolein is a toxic, highly reactive α,β-unsaturated aldehyde. In the current study, the products of acrolein after reaction with Glycerophosphoethanolamine (GPEtn) lipids have been characterized using electrospray tandem mass spectrometry. The major product formed involves the addition of two acrolein molecules to the primary amine of GPEtn lipids and subsequent aldol condensation to form 1,2-diradyl-sn-glycero-3-phosphoethanol-(3-formyl-4-hydroxy)piperidine (FHP) lipids. Upon sodium borohydride reduction, 1,2-diradyl-sn-glycero-3-phosphoethanol-(3-hydroxymethyl-4-hydroxy)piperidine (HMHP) lipids and 1,2-diradyl-sn-glycero-3-phosphoethanol-(3-hydroxymethyl-3,4-dehydro)piperidine (HMDP) lipids were selectively detected using electrospray tandem mass spectrometry by employing precursors of m/z 256.1 and 238.1 scans, respectively. HMHP lipid and HMDP lipid molecular species were detected upon treatment of HL-60 cells with concentrations of acrolein as low as 10 μM. While the biological implications of these acrolein GPEtn adducts have yet to be established, these structural characterization studies reported herein reveal the facile formation of acrolein GPEtn lipid adducts in vitro, which could influence subsequent biochemical events within the cell.
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electrospray ionization tandem mass spectrometry of Glycerophosphoethanolamine plasmalogen phospholipids
Journal of the American Society for Mass Spectrometry, 2004Co-Authors: Karin Zemski A Berry, Robert C. MurphyAbstract:Collision-induced dissociation (CID) of the [M + H]+ of glycerophospholipids typically results in abundant fragment ions that are related to the polar head group or loss of the polar head group. An exception to this general rule occurs for Glycerophosphoethanolamines (GPEtn), which are a class of phospholipids that can have an acyl, 1-O-alkyl, or 1-O-alk-1′-enyl group as a substituent at the sn-1 position. The CID of the [M + H]+ of diacyl-GPEtn typically results in the expected loss of the phosphoethanolamine head group (141 Da). Therefore, constant neutral loss of 141 Da has been used as a diagnostic tool for the determination of GPEtn species in complex lipid mixtures. One disadvantage in using constant neutral loss of 141 Da in order to determine GPEtn content in lipid mixtures is that plasmalogen GPEtn does not undergo neutral loss of phosphoethanolamine to the same extent as diacyl-GPEtn. The current studies have used positive ion mode electrospray tandem mass spectrometry to study the collision-induced dissociation of various GPEtn plasmalogens present in the phospholipid membranes of human neutrophils. The CID of the [M + H]+ of plasmalogen GPEtn resulted in two prominent fragment ions; one that was characteristic of the sn-1 position and one that was characteristic of the sn-2 position. These two ions were used to detect specific molecular species of GPEtn containing esterified arachidonate (precursors of m/z 361) present in the human neutrophil.
Beiwei Zhu - One of the best experts on this subject based on the ideXlab platform.
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effects of antioxidants of bamboo leaves aob on the oxidative susceptibility of glycerophosphocholine and Glycerophosphoethanolamine in dried scallop argopecten irradians adductor muscle during storage
Lwt - Food Science and Technology, 2020Co-Authors: Hongkai Xie, Fereidoon Shahidi, Da Yong Zhou, Fa-wen Yin, Beiwei Zhu, Mantong Zhao, Min Zhang, Zhongyuan Liu, Xiaoyang LiuAbstract:Abstract Phospholipids (PLs), the main lipid component in marine shellfish, consist mainly of glycerophosphocholine (GPC) and Glycerophosphoethanolamine (GPE). This work compared the oxidative susceptibility of GPC and GPE in dried shellfish during storage and also investigated the effects of natural phenolic antioxidant on such oxidative susceptibility. The content of four representative polyunsaturated fatty acids (C18:3 n-3, C20:4 n-6, C20:5 n-3, and C22:6 n-3) esterified onto GPC or GPE in dried scallop adductor muscle during storage at two temperatures were matched with first-order kinetic models, in order to ascertain the oxidation reaction rate constant (k). The results showed that GPE possessed greater oxidation rate than GPC during storage, and GPC could be more effectively protected by the antioxidants of bamboo leaves (AOB, polar polyphenolic antioxidants) compared with GPE. This study provides a practical method for accurate evaluation of oxidative susceptibility of different PL classes in complex food systems.
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Lipid profiles in different parts of two species of scallops (Chlamys farreri and Patinopecten yessoensis).
Food Chemistry, 2017Co-Authors: Da Yong Zhou, Jiang-hua Zhang, Liang Song, Qi Zhao, Fa-wen Yin, Lei Qin, Beiwei ZhuAbstract:Different classes of lipids and phospholipids (PL) as well as fatty acid (FA) compositions, and glycerophospholipid (GP) molecular species in edible parts (adductor muscles) and by-products (gonads and mantles) of scallops Patinopecten yessoensis and Chlamys farreri were characterized. The lipids contained high levels of polyunsaturated FA (PUFA) (20.44-58.81% of total FAs) and PL (54.99-78.26% of total lipids). Among PL, phosphatidylcholine (41.39-51.86 mol%) was dominant. More than 230 GP species belonging to glycerophosphocholine, Glycerophosphoethanolamine, glycerophosphoserine, glycerophosphoinositol, lysoglycerophosphocholine, lysoGlycerophosphoethanolamine and lysoglycerophosphoinositol were characterized. Individual GP molecular species in different body parts of scallops were also partially quantified. Most of the dominant GP species contained PUFA, especially eicosapentaenoic acid (EPA, 20:5n-3) and docosahexaenoic acid (DHA, 22:6n-3). Considering the high level of PUFA enriched GP, edible parts and by-products (gonads and mantles) of scallops Patinopecten yessoensis and Chlamys farreri provide great potential as health-promoting food for human consumption.
Da Yong Zhou - One of the best experts on this subject based on the ideXlab platform.
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effects of antioxidants of bamboo leaves aob on the oxidative susceptibility of glycerophosphocholine and Glycerophosphoethanolamine in dried scallop argopecten irradians adductor muscle during storage
Lwt - Food Science and Technology, 2020Co-Authors: Hongkai Xie, Fereidoon Shahidi, Da Yong Zhou, Fa-wen Yin, Beiwei Zhu, Mantong Zhao, Min Zhang, Zhongyuan Liu, Xiaoyang LiuAbstract:Abstract Phospholipids (PLs), the main lipid component in marine shellfish, consist mainly of glycerophosphocholine (GPC) and Glycerophosphoethanolamine (GPE). This work compared the oxidative susceptibility of GPC and GPE in dried shellfish during storage and also investigated the effects of natural phenolic antioxidant on such oxidative susceptibility. The content of four representative polyunsaturated fatty acids (C18:3 n-3, C20:4 n-6, C20:5 n-3, and C22:6 n-3) esterified onto GPC or GPE in dried scallop adductor muscle during storage at two temperatures were matched with first-order kinetic models, in order to ascertain the oxidation reaction rate constant (k). The results showed that GPE possessed greater oxidation rate than GPC during storage, and GPC could be more effectively protected by the antioxidants of bamboo leaves (AOB, polar polyphenolic antioxidants) compared with GPE. This study provides a practical method for accurate evaluation of oxidative susceptibility of different PL classes in complex food systems.
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Characterization of Glycerophospholipid Molecular Species in Two Species of Arcidaes (Scapharca subcrenata and Scapharca broughtonii)
Journal of Aquatic Food Product Technology, 2019Co-Authors: Zi-xuan Wu, Kanyasiri Rakariyatham, Qi Zhao, Jing Zhang, Da Yong ZhouAbstract:In this study, the molecular species of glycerophosphocholine (GPCho), Glycerophosphoethanolamine (GPEtn), glycerophosphoserine (GPSer), glycerophosphatidylinositol (GPIns), lysoglycerophosphocholine (LGPCho), and lysoGlycerophosphoethanolamine (LGPEtn) from arcidaes Scapharca subcrenata and Scapharca broughtonii were characterized using direct infusion-tandem mass (shotgun) method for the first time. At least 201 and 303 glycerophospholipid (GP) molecular species were characterized, respectively. Most of the predominant GP molecular species contained polyunsaturated fatty acids (PUFA), mainly eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Meanwhile, the arcidae lipids contained a high proportion of polar lipids (81.57–86.72% of total lipids). Among PL, phosphatidylcholine (30.53–32.04 mol%) and phosphatidylethanolamine (21.48–26.71 mol%) were dominant.
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Lipid profiles in different parts of two species of scallops (Chlamys farreri and Patinopecten yessoensis).
Food Chemistry, 2017Co-Authors: Da Yong Zhou, Jiang-hua Zhang, Liang Song, Qi Zhao, Fa-wen Yin, Lei Qin, Beiwei ZhuAbstract:Different classes of lipids and phospholipids (PL) as well as fatty acid (FA) compositions, and glycerophospholipid (GP) molecular species in edible parts (adductor muscles) and by-products (gonads and mantles) of scallops Patinopecten yessoensis and Chlamys farreri were characterized. The lipids contained high levels of polyunsaturated FA (PUFA) (20.44-58.81% of total FAs) and PL (54.99-78.26% of total lipids). Among PL, phosphatidylcholine (41.39-51.86 mol%) was dominant. More than 230 GP species belonging to glycerophosphocholine, Glycerophosphoethanolamine, glycerophosphoserine, glycerophosphoinositol, lysoglycerophosphocholine, lysoGlycerophosphoethanolamine and lysoglycerophosphoinositol were characterized. Individual GP molecular species in different body parts of scallops were also partially quantified. Most of the dominant GP species contained PUFA, especially eicosapentaenoic acid (EPA, 20:5n-3) and docosahexaenoic acid (DHA, 22:6n-3). Considering the high level of PUFA enriched GP, edible parts and by-products (gonads and mantles) of scallops Patinopecten yessoensis and Chlamys farreri provide great potential as health-promoting food for human consumption.
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Characterization of lipids in three species of sea urchin
Food Chemistry, 2017Co-Authors: Xin Zhou, Jiang-hua Zhang, Xiao-pei Hu, Ting Lu, Da Yong Zhou, Qi Zhao, Fereidoon ShahidiAbstract:Abstract Sea urchin gonad has been regarded as a “healthy” food. Although previous studies have suggested that sea urchin gonad might serve as a potential rich source of long chain omega-3 polyunsaturated fatty acids (n-3 LC-PUFA) enriched phospholipid (PL), the molecular species profile of its PL has rarely been reported. In this study, about 200 molecular species of glycerophospholipid (GP), including glycerophosphocholine, Glycerophosphoethanolamine, glycerophosphoserine, glycerophosphoinositol, lysoglycerophosphocholine and lysoGlycerophosphoethanolamine, in gonads from three species of sea urchin (Glyptocidaris crenularis, Strongylocentrotus intermedius and Strongylocentrotus nudus) were characterized using tandem mass spectrometry. Most of the predominant GP molecular species contained PUFA, especially eicosapentaenoic acid (EPA). Meanwhile, the sea urchin lipids contained a high proportion of PL (39.45–50.30% of total lipids) and PUFA (34.47–46.56% of total FA). Among PL, phosphatidylcholine (67.88–72.58 mol%) was dominant. Considering the high level of PUFA enriched GP, sea urchin gonads provide great potential as health-promoting food for human consumption.
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Characterization of glycerophospholipid molecular species in six species of edible clams by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry
Food Chemistry, 2016Co-Authors: Da Yong Zhou, Xiao-pei Hu, Jian-run Zhang, Liang Song, Qi Zhao, Fereidoon ShahidiAbstract:The molecular species of glycerophosphocholine (GPCho), Glycerophosphoethanolamine (GPEtn), glycerophosphoserine (GPSer), lysoglycerophosphocholine (LGPCho) and lysoGlycerophosphoethanolamine (LGPEtn) from six species of edible clams were characterized by using high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. At least 435, 453, 468, 443, 427 and 444 glycerophospholipid (GP) molecular species were characterized, respectively, from Cyclina sinensis, Mactra chinensis Philippi, Mactra veneriformis Reeve, Meretrix meretrix, Ruditapes philippinarum and Saxidomus purpurata. Most of the predominant GP molecular species in clam contained polyunsaturated fatty acids (PUFA), mainly eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), indicating that clam is a potential resource of GP enriched PUFA. According to the amount of the major molecular species containing EPA and DHA, Cyclina sinensis was the best fit species for GPCho, Mactra veneriformis Reeve was the best fit species for GPEtn, Mactra chinensis Philippi was the best fit species for GPSer and LGPEtn, and Saxidomus purpurata was the best fit species for LGPCho.
John Turk - One of the best experts on this subject based on the ideXlab platform.
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electrospray ionization with low energy collisionally activated dissociation tandem mass spectrometry of glycerophospholipids mechanisms of fragmentation and structural characterization
Journal of Chromatography B, 2009Co-Authors: Fongfu Hsu, John TurkAbstract:This review describes the use of low-energy collisionally activated dissociation (CAD) with both tandem quadrupole and ion-trap mass spectrometry toward structural characterization of glycerophospholipids (GPLs), including classes of glycerophosphocholine, Glycerophosphoethanolamine, glycerophosphoserine, glycerophosphoglycerol glycerophosphoinositol and glycerophosphatidic acid, as well as their lyso-, plasmanyl-, and plasmenylphospholipid subclasses. The mechanisms underlying the fragmentation processes leading to structural characterization of GPLs in various ion forms desorbed by electrospray ionization in the positive-ion and negative-ion modes are also discussed. The tandem mass spectrometric approaches afford the identification of the polar head group, the fatty acid substituents and the location of the radyl groups on the glycerol backbone of all the GPLs.
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Characterization of phosphatidylethanolamine as a lithiated adduct by triple quadrupole tandem mass spectrometry with electrospray ionization.
Journal of Mass Spectrometry, 2000Co-Authors: Fongfu Hsu, John TurkAbstract:Structural characterization of the Glycerophosphoethanolamine (GPE) molecule as a lithiated adduct ion by collisionally activated dissociation (CAD) tandem mass spectrometry with electrospray ionization is described. Abundant fragment ions reflecting polar head group and fatty acid constituents were observed in the product ion spectrum of GPE, which permits an unambiguous structural determination, including the regiospecificity of fatty acyl substituents. The pathways leading to the formation of fragment ions are proposed. The suggested mechanisms are supported by the tandem mass spectra of various deuterated analogs and source CAD of GPE followed by CAD tandem mass spectrometry. Identification of GPE molecular species and specific GPE subclasses in a biological mixture by tandem mass spectrometry with various constant neutral loss scannings is also described. Copyright © 2000 John Wiley & Sons, Ltd.
Hiroshi Morioka - One of the best experts on this subject based on the ideXlab platform.
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Siladenoserinols A–L: New Sulfonated Serinol Derivatives from a Tunicate as Inhibitors of p53–Hdm2 Interaction
2013Co-Authors: Yuichi Nakamura, Hikaru Kato, Tadateru Nishikawa, Noriyuki Iwasaki, Yoshiaki Suwa, Henki Rotinsulu, Fije Losung, Wilmar Maarisit, Remy E. P. Mangindaan, Hiroshi MoriokaAbstract:Siladenoserinols A–L were isolated from a tunicate as inhibitors of p53–Hdm2 interaction, a promising target for cancer chemotherapy. Their structures including the absolute configurations were elucidated to be new sulfonated serinol derivatives, each of which contains a 6,8-dioxabicyclo[3.2.1]octane unit and either glycerophosphocholine or Glycerophosphoethanolamine moiety. They inhibited p53–Hdm2 interaction with IC50 values of 2.0–55 μM. Among them, siladenoserinol A and B exhibited the strongest inhibition with an IC50 value of 2.0 μM
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Siladenoserinols A-L: new sulfonated serinol derivatives from a tunicate as inhibitors of p53-Hdm2 interaction.
Organic Letters, 2012Co-Authors: Yuichi Nakamura, Hikaru Kato, Tadateru Nishikawa, Noriyuki Iwasaki, Yoshiaki Suwa, Henki Rotinsulu, Fije Losung, Wilmar Maarisit, Remy E. P. Mangindaan, Hiroshi MoriokaAbstract:Siladenoserinols A–L were isolated from a tunicate as inhibitors of p53–Hdm2 interaction, a promising target for cancer chemotherapy. Their structures including the absolute configurations were elucidated to be new sulfonated serinol derivatives, each of which contains a 6,8-dioxabicyclo[3.2.1]octane unit and either glycerophosphocholine or Glycerophosphoethanolamine moiety. They inhibited p53–Hdm2 interaction with IC50 values of 2.0–55 μM. Among them, siladenoserinol A and B exhibited the strongest inhibition with an IC50 value of 2.0 μM.