Cholesteryl ester hydroperoxide formation in myoglobin-catalyzed low density lipoprotein oxidation: concerted antioxidant activity of caffeic and p-coumaric acids with ascorbate.

Abstract:

:Two diet-derived phenolic acids, caffeic and p-coumaric acids, interplayed with ascorbate in the protection of low density lipoproteins (LDL) from oxidation promoted by ferrylmyoglobin. Ferrylmyoglobin, a two-electron oxidation product from the reaction of metmyoglobin and H2O2, was able to oxidize LDL, degrading free cholesterol and cholesteryl esters. Upon exposure to ferrylmyoglobin, LDL became rapidly depleted of cholesteryl arachidonate and linoleate, which turn into the corresponding hydroperoxides. Cholesteryl oleate and cholesterol were, comparatively, more resistant to oxidation. Caffeic (2 microM) and p-coumaric (12 microM) acids efficiently delayed oxidations, as reflected by an increase in the lag times required for linoleate hydroperoxide and 7-ketocholesterol formation as well as for cholesteryl linoleate consumption. At the same concentration, ascorbate, a standard water-soluble antioxidant, was less efficient than the phenolic acids. Additionally, phenolic acids afforded a protection to LDL that, conversely to ascorbate, extends along the time, as inferred from the high levels of cholesteryl linoleate and cholesteryl arachidonate left after 22 hr of oxidation challenging. Significantly, the coincubation of LDL with ascorbate and each of the phenolic acids resulted in a synergistic protection from oxidation. This was inferred from the lag phases of cholesteryl linoleate hydroperoxide (the major peroxide found in LDL) formation in the presence of mixtures of ascorbate with phenolic acids longer than the sum of individual lag phases of ascorbate and the phenolic acids. A similar description could be drawn for the accumulation of a late product of oxidation, 7-ketocholesterol. It is concluded that ferrylmyoglobin induces a typical pattern of LDL lipid peroxidation, the oxidation rate of cholesteryl esters being a function of unsaturation; furthermore, there is a synergistic antioxidant activity of diet-derived phenolic acids with ascorbate in the protection of LDL from oxidation, a finding of putative physiological relevance.

journal_name

Biochem Pharmacol

journal_title

Biochemical pharmacology

authors

Vieira O,Laranjinha J,Madeira V,Almeida L

doi

10.1016/s0006-2952(97)00470-x

subject

Has Abstract

pub_date

1998-02-01 00:00:00

pages

333-40

issue

3

eissn

0006-2952

issn

1873-2968

pii

S0006-2952(97)00470-X

journal_volume

55

pub_type

杂志文章
  • Metabolism-dependent binding of the chlorinated insecticide DDT and its metabolite, DDD, to microsomal protein and lipids.

    abstract::Dichlorodi[U-14C]phenyltrichloroethane ( [14C]DDT), incubated with rat hepatic microsomes and NADPH, produced reactive intermediates which covalently bound to microsomal protein and lipids. In atmospheric oxygen, DDT bound to microsomal protein; however, binding was increased up to approximately 70% by oxygen depletio...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(84)90483-0

    authors: Baker MT,Van Dyke RA

    更新日期:1984-01-15 00:00:00

  • Basement membrane components (matrigel) promote the tumorigenicity of human breast adenocarcinoma MCF7 cells and provide an in vivo model to assess the responsiveness of cells to estrogen.

    abstract::The ability to transplant human tumors into athymic nude mice allows studies of tumor cells in vivo. However, after s.c. injection the incidence of tumor and metastases in nude mice is frequently low. We have studied the tumorigenicity in nude mice of estradiol (E2)-sensitive breast adenocarcinoma MCF7 cells. Matrigel...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(92)90501-9

    authors: Noel A,Simon N,Raus J,Foidart JM

    更新日期:1992-03-17 00:00:00

  • Participation of cyclin D1 deregulation in TNP-470-mediated cytostatic effect: involvement of senescence.

    abstract::Inhibition of angiogenesis is becoming one promising, alternative approach to stop tumor from growth and spreading to distant organs. TNP-470, an analog of fumagillin, possesses potent anti-angiogenic effects with minimal toxicity in animal tumor models and is now in the phase III of human cancer trial. Although TNP-4...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2004.05.020

    authors: Lien WH,Chen CK,Lai LY,Chen YH,Wu MP,Wu LW

    更新日期:2004-08-15 00:00:00

  • Regulation of adenylate cyclase by cannabinoid drugs. Insights based on thermodynamic studies.

    abstract::The abilities of lipophilic cannabinoid drugs to regulate adenylate cyclase activity in neuroblastoma cell membranes were analyzed by thermodynamic studies. Arrhenius plots of hormone-stimulated adenylate cyclase activity exhibited a break point at 20 degrees. The break point was reduced to 14 degrees by benzyl alcoho...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(89)90628-x

    authors: Howlett AC,Scott DK,Wilken GH

    更新日期:1989-10-01 00:00:00

  • Inhibition of phosphatidylinositol 3-kinase-mediated glucose metabolism coincides with resveratrol-induced cell cycle arrest in human diffuse large B-cell lymphomas.

    abstract::An abnormally high rate of aerobic glycolysis is characteristic of many transformed cells. Here we report the polyphenolic compound, resveratrol, inhibited phosphatidylinositol 3-kinase (PI-3K) signaling and glucose metabolism, coinciding with cell-cycle arrest, in germinal center (GC)-like LY1 and LY18 human diffuse ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2006.08.009

    authors: Faber AC,Dufort FJ,Blair D,Wagner D,Roberts MF,Chiles TC

    更新日期:2006-11-15 00:00:00

  • A mechanistic study of proliferation induced by Angelica sinensis in a normal gastric epithelial cell line.

    abstract::It has been reported that an extract from Angelica sinensis mainly consisting of polysaccharides (95%) prevented ethanol- or indomethacin-induced gastric mucosal damage (Cho CH et al. Planta Med 2000;66:348-51). However, it is not known whether Angelica sinensis has a direct stimulatory effect on the healing of gastri...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(01)00625-6

    authors: Ye YN,Liu ES,Shin VY,Koo MW,Li Y,Wei EQ,Matsui H,Cho CH

    更新日期:2001-06-01 00:00:00

  • Pharmacological and biochemical determinants of the antitumour activity of the indoloquinone EO9.

    abstract::EO9 is a novel bioreductive drug which has recently undergone extensive clinical evaluation. Its mechanism of action remains to be clearly defined. Antitumour activity of EO9 has been determined in 2 human colon cancer xenografts (HT-29 and BE) and 2 murine colon adenocarcinomas (MAC 16 and 26) after intratumoural inj...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(97)00265-7

    authors: Cummings J,Spanswick VJ,Gardiner J,Ritchie A,Smyth JF

    更新日期:1998-02-01 00:00:00

  • A novel xenobiotic responsive element regulated by aryl hydrocarbon receptor is involved in the induction of BCRP/ABCG2 in LS174T cells.

    abstract::Induction of the breast cancer resistance protein (BCRP/ABCG2) expression has been found in various tissues and cell-types after exposure to chemicals including 17β-estradiol, rosiglitazone, imatinib, as well as aryl hydrocarbon receptor (AhR) activators such as 2,3,7,8-tetrachlorodibenzodioxin, 3-methylcholanthrene (...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2010.08.016

    authors: Tompkins LM,Li H,Li L,Lynch C,Xie Y,Nakanishi T,Ross DD,Wang H

    更新日期:2010-12-01 00:00:00

  • Sulfated polymannuroguluronate, a novel anti-AIDS drug candidate, inhibits HIV-1 Tat-induced angiogenesis in Kaposi's sarcoma cells.

    abstract::Kaposi's sarcoma (KS), a neoplasm often associated with iatrogenic and acquired immunosuppression, is characterized by prominent angiogenesis. Angiogenic factors released from KS and host cells and HIV viral products-the protein Tat are reported to be involved in angiogenesis. Mounting evidence further suggests that m...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2007.06.012

    authors: Lu CX,Li J,Sun YX,Qi X,Wang QJ,Xin XL,Geng MY

    更新日期:2007-11-01 00:00:00

  • Inhibition of phagocyte chemotaxis by uteroglobin, an inhibitor of blastocyst rejection.

    abstract::Uteroglobin, a steroid-dependent secretory protein first discovered in the rabbit uterus during early pregnancy, is a potent phospholipase A2 inhibitor. We found that uteroglobin also inhibited human and rabbit phagocyte chemotaxis in response to formyl peptide attractants in a dose-dependent manner. Half-maximal inhi...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(88)90204-3

    authors: Vasanthakumar G,Manjunath R,Mukherjee AB,Warabi H,Schiffmann E

    更新日期:1988-02-01 00:00:00

  • Allosteric regulation of cloned m1-m5 muscarinic receptor subtypes.

    abstract::Allosteric regulation of [3H]N-methylscopolamine [( 3H]NMS) and [3H]quinuclidinyl benzilate [( 3H]QNB) dissociation from the m1-m5 muscarinic receptor subtypes was examined in transfected CHO-K1 cells. Half-times of dissociation of [3H]NMS from cell membranes (at 23 degrees) ranged from less than 5 min for the m2 subt...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(91)90591-r

    authors: Ellis J,Huyler J,Brann MR

    更新日期:1991-10-24 00:00:00

  • Effect of okadaic acid on immunologic and non-immunologic histamine release in rat mast cells.

    abstract::We have studied the effect of the protein phosphatase (PP) inhibitor, okadaic acid (OKA) on histamine release elicited by immunologic and non-immunologic stimuli in peritoneal and pleural rat mast cells. When cells were stimulated with antigen (egg albumin), OKA strongly inhibited histamine release. This finding sugge...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(94)90194-5

    authors: Estévez MD,Vieytes MR,Louzao MC,Botana LM

    更新日期:1994-02-09 00:00:00

  • Modulation of cell sensitivity to antitumor agents by targeting survival pathways.

    abstract::The advent of drugs targeting tumor-associated prosurvival alterations of cancer cells has changed the interest of antitumor drug development from cytotoxic drugs to target-specific agents. Although single-agent therapy with molecularly targeted agents has shown limited success in tumor growth control, a promising str...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2010.07.030

    authors: Perego P,Cossa G,Zuco V,Zunino F

    更新日期:2010-11-15 00:00:00

  • Reduction of thyroid hormones triggers down-regulation of hepatic CYP2B through nuclear receptors CAR and TR in a rat model of acute stroke.

    abstract::Stroke is a neurological condition and may cause changes in hepatic drug-metabolizing enzymes. Hepatic CYP2B is involved in the metabolism of a variety of centrally active substances. The purpose of this study was to investigate the possible down-regulation mechanism of hepatic CYP2B after acute stroke. Using a rat mo...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2013.12.011

    authors: Bing Y,Zhu S,Jiang K,Dong G,Li J,Yang Z,Yang J,Yue J

    更新日期:2014-02-15 00:00:00

  • Azalanstat (RS-21607), a lanosterol 14 alpha-demethylase inhibitor with cholesterol-lowering activity.

    abstract::Agents that inhibit hepatic cholesterol biosynthesis reduce circulating cholesterol levels in experimental animals and humans, and may be of pharmacological importance in the prevention of atherosclerosis. Azalanstat (RS-21607), a synthetic imidazole, has been shown to inhibit cholesterol synthesis in HepG2 cells, hum...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(95)00152-p

    authors: Burton PM,Swinney DC,Heller R,Dunlap B,Chiou M,Malonzo E,Haller J,Walker KA,Salari A,Murakami S

    更新日期:1995-08-08 00:00:00

  • Characterization of multiple epoxide hydrolase activities in mouse liver nuclear envelope.

    abstract::A nuclear envelope-associated epoxide hydrolase in mouse liver that hydrates trans-stilbene oxide has been identified and characterized. This epoxide hydrolase is distinct from the enzyme in nuclear envelopes that hydrates benzo[a]pyrene 4,5-oxide and other arene oxides. This distinction was demonstrated by the criter...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(86)90422-3

    authors: Guenthner TM

    更新日期:1986-10-01 00:00:00

  • Carbamazepine metabolism to a reactive intermediate by the myeloperoxidase system of activated neutrophils.

    abstract::Carbamazepine is an anticonvulsant which is associated with a significant incidence of hypersensitivity reactions including agranulocytosis. We have postulated that many drug hypersensitivity reactions, especially agranulocytosis and lupus, are due to reactive metabolites generated by the myeloperoxidase (MPO) (EC 1.1...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(93)90279-6

    authors: Furst SM,Uetrecht JP

    更新日期:1993-03-24 00:00:00

  • Src-family kinase inhibitors block early steps of caveolin-1-enhanced lung metastasis by melanoma cells.

    abstract::In advanced stages of cancer disease, caveolin-1 (CAV1) expression increases and correlates with increased migratory and invasive capacity of the respective tumor cells. Previous findings from our laboratory revealed that specific ECM-integrin interactions and tyrosine-14 phosphorylation of CAV1 are required for CAV1-...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2020.113941

    authors: Ortiz R,Díaz J,Díaz-Valdivia N,Martínez S,Simón L,Contreras P,Lobos-González L,Guerrero S,Leyton L,Quest AFG

    更新日期:2020-07-01 00:00:00

  • Hepatic protein tyrosine phosphatase 1B (PTP1B) deficiency protects against obesity-induced endothelial dysfunction.

    abstract::Growing evidence suggests that hepatic-insulin resistance is sufficient to promote progression to cardiovascular disease. We have shown previously that liver-specific protein-tyrosine-phosphatase 1B (PTP1B) deficiency improves hepatic-insulin sensitivity and whole-body glucose homeostasis. The aim of this study was to...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2014.10.008

    authors: Agouni A,Tual-Chalot S,Chalopin M,Duluc L,Mody N,Martinez MC,Andriantsitohaina R,Delibegović M

    更新日期:2014-12-15 00:00:00

  • Role of conformational alteration in the epidermal growth factor receptor (EGFR) function.

    abstract::This mini-review addresses the effect of glycosylation and phosphorylation on the conformational alterations of the epidermal growth factor receptor (EGFR). Based on studies with full-length and truncated EGFRs, we propose a model to suggest that receptor-receptor self-association, which occurs in the truncated recept...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/s0006-2952(00)00425-1

    authors: Bishayee S

    更新日期:2000-10-15 00:00:00

  • The GABAA receptor-gated ion channel: biochemical and pharmacological studies of structure and function.

    abstract::In the past few years, substantial advances have been made in analyzing the structure and function of the GABA receptor-gated Cl- channel. A major goal is to identify the molecular characteristics of the GABAA receptor that are necessary for maintaining normal GABAergic neurotransmission. Future studies will undoubted...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/0006-2952(88)90684-3

    authors: Schwartz RD

    更新日期:1988-09-15 00:00:00

  • Deficient induction of sulfobromophthalein conjugating activity by phenobarbital in hamster liver.

    abstract::Administration of phenobarbital, a known inducer of glutathione S-transferase activity in rat liver, failed to stimulate sulfobromophthalein (BSP) conjugation by liver cytosol in hamsters. The latter displayed poor ability to conjugate this substrate, despite very high glutathione-conjugating activity with the broad-s...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(87)90540-5

    authors: Foliot A,Touchard D,Myara A,Trivin F,Chauffert M

    更新日期:1987-08-15 00:00:00

  • Pleiotropic effects of selective CDK inhibitors on human normal and cancer cells.

    abstract::Escape from the proper control of the cell cycle by up-regulation of cyclins or aberrant activation of cyclin-dependent kinases (CDKs) as well as by inactivation of cellular inhibitors of CDKs (CKI) leads to malignant transformation. Loss of cellular CKIs in cancers provided a rationale for development of pharmacologi...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2008.07.040

    authors: Wesierska-Gadek J,Hajek SB,Sarg B,Wandl S,Walzi E,Lindner H

    更新日期:2008-12-01 00:00:00

  • Low-affinity uptake of the fluorescent organic cation 4-(4-(dimethylamino)styryl)-N-methylpyridinium iodide (4-Di-1-ASP) in BeWo cells.

    abstract::Understanding the mechanisms of transport processes in the placenta can improve the safety and efficacy of drug delivery during pregnancy. Functional studies of organic cation transporters (OCTs) are usually carried out using radioactivity, and a fluorescent marker would add flexibility to experimental methods. As a p...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2006.11.020

    authors: Rytting E,Bryan J,Southard M,Audus KL

    更新日期:2007-03-15 00:00:00

  • Tissue distribution of captopril, reducible captopril conjugates and S-methylcaptopril in the rat.

    abstract::The tissue distribution of captopril, an antihypertensive drug possessing a free sulfhydryl group, and its sulfur-conjugated metabolites was studied in rats by gas chromatography-mass spectrometry at 15, 30 and 60 min following a single 10 mg/kg oral dose of captopril. It was found that tissue accumulation of captopri...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(83)90328-3

    authors: Drummer OH,Worland PJ,Jarrott B

    更新日期:1983-05-15 00:00:00

  • Comparison of the hepatic mixed function oxidase system of young, adult, and old non-human primates (Macaca nemestrina).

    abstract::The influence of age on the mixed function oxidase system from a non-human primate was studied. Microsomes were isolated from the livers of female Macaca nemestrina ranging from 2 to 21 years of age. No significant age-related change was observed in either the cytochrome P-450 content or the NADPH cytochrome c reducta...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(85)90025-5

    authors: Sutter MA,Wood WG,Williamson LS,Strong R,Pickham K,Richardson A

    更新日期:1985-08-15 00:00:00

  • Fatty acid-induced alterations in transport systems of the small intestinal brush-border membrane.

    abstract::We have investigated the effects of fatty acids on the Na+-H+ exchanger and other carrier-mediated transport systems in intestinal brush-border membrane vesicles. The Na+-H+ exchanger (i.e. H+ gradient-dependent, dimethylamiloride-sensitive Na+ uptake) was strongly inhibited by fatty acids and the inhibition was conce...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(88)90800-3

    authors: Tiruppathi C,Miyamoto Y,Ganapathy V,Leibach FH

    更新日期:1988-04-01 00:00:00

  • Evidence for separate effects of U73122 on phospholipase C and calcium channels in human platelets.

    abstract::U73122 ((1-[6-(( 17beta-3-methoxyestra-1,3,5(10)-trien-17-yl)amino)exyl]-1H-p yrrole-2,5-dione)) is generally used as a selective inhibitor of phospholipase C (PLC) and the related rise in cytosolic Ca2+. Recently, by using hepatocytes, it was suggested that its action sites are different for PLC activation and increa...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(98)00146-4

    authors: Pulcinelli FM,Gresele P,Bonuglia M,Gazzaniga PP

    更新日期:1998-12-01 00:00:00

  • Electron paramagnetic resonance spectrometry evidence for bioreduction of tirapazamine to oxidising free radicals under anaerobic conditions.

    abstract::Tirapazamine (SR 4233) is a bioreductive antitumour drug in Phase III clinical trial which is activated in hypoxic tumour regions to generate a cytotoxic species. Electron paramagnetic resonance (EPR) spectrometry was used to investigate directly the formation of free radicals as the result of tirapazamine reduction b...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(00)00487-1

    authors: Patterson LH,Taiwo FA

    更新日期:2000-12-15 00:00:00

  • Endopeptidase-24.11 cleaves a chemotactic factor from alpha-calcitonin gene-related peptide.

    abstract::The sequence of rat alpha-calcitonin gene-related peptide (CGRP-alpha) contains the tetrapeptide eosinophil granulocyte chemotactic factor Val32-Gly-Ser-Glu35. Peptide fragments formed following hydrolysis of rat CGRP-alpha in vitro by endopeptidase-24.11 were identified. The tetrapeptide fragment was generated follow...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(92)90706-o

    authors: Davies D,Medeiros MS,Keen J,Turner AJ,Haynes LW

    更新日期:1992-04-15 00:00:00