The detection and identification of 42,43,44,45,46,47,55-heptanor-41-oxoyessotoxin, a new marine toxin from adriatic shellfish, by liquid chromatography-mass spectrometry.

Abstract:

:The diarrhetic shellfish toxin composition in the digestive glands of mussels collected in June 2001 from the Northern Adriatic sea was investigated by high-performance liquid chromatography coupled with electrospray ion trap mass spectrometry. Along with known yessotoxins (1, 3-6), identified by comparison of their retention times and mass spectra with those of appropriate standards, a new marine toxin, 42,43,44,45,46,47,55-heptanor-41-oxoyessotoxin, 7, was detected. MS/MS experiments were used to gain structural information. 7 represents a new addition to the class of yessotoxins.

journal_name

Chem Res Toxicol

authors

Ciminiello P,Dell'Aversano C,Fattorusso E,Forino M,Magno S,Poletti R

doi

10.1021/tx025527z

subject

Has Abstract

pub_date

2002-07-01 00:00:00

pages

979-84

issue

7

eissn

0893-228X

issn

1520-5010

pii

tx025527z

journal_volume

15

pub_type

杂志文章
  • The Multiple Biological Targets of Hops and Bioactive Compounds.

    abstract::Botanical dietary supplements for women's health are increasingly popular. Older women tend to take botanical supplements such as hops as natural alternatives to traditional hormone therapy to relieve menopausal symptoms. Especially extracts from spent hops, the plant material remaining after beer brewing, are enriche...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章,评审

    doi:10.1021/acs.chemrestox.8b00345

    authors: Bolton JL,Dunlap TL,Hajirahimkhan A,Mbachu O,Chen SN,Chadwick L,Nikolic D,van Breemen RB,Pauli GF,Dietz BM

    更新日期:2019-02-18 00:00:00

  • Inhibition of 2,5-hexanedione-induced protein cross-linking by biological thiols: chemical mechanisms and toxicological implications.

    abstract::n-Hexane is metabolized to the gamma-diketone 2,5-hexanedione (2,5-HD), a derivative that covalently binds to lysine residues in neurofilament (NF) protein to yield 2,5-dimethylpyrrole adducts. Studies comparing the pyrrole-forming potential and neurotoxic potency of gamma-diketones have demonstrated that pyrrolylatio...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00047a017

    authors: Zhu M,Spink DC,Yan B,Bank S,DeCaprio AP

    更新日期:1995-07-01 00:00:00

  • Synthesis and mutagenicity of trans-dihydrodiol metabolites of benzo[b]naphtho[2,1-d]thiophene.

    abstract::The syntheses of potentially important metabolites of benzo[b]naphtho[2,1-d]thiophene ([2,1]BNT)--trans-1,2-dihydroxy-1,2-dihydrobenzo[b]naphtho[2,1- d]thiophene ([2,1]BNT-1,2-diol) and trans-3,4-dihydroxy-3,4-dihydrobenzo[b]naphtho[2,1-d]thiophene ([2,1]BNT-3,4-diol)--are described. The syntheses involved preparation...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00014a002

    authors: Misra B,Amin S

    更新日期:1990-03-01 00:00:00

  • Limited reactivity of formyl chloride with glutathione and relevance to metabolism and toxicity of dichloromethane.

    abstract::Formyl chloride has been indirectly implicated as an intermediate in the oxidation of CH(2)Cl(2) and proposed to be a product of the oxidation of some other compounds. Formyl chloride was synthesized and added to aqueous solutions, with CO formed as a product. The presence of glutathione (GSH) did not reduce the yield...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx060087n

    authors: Watanabe K,Guengerich FP

    更新日期:2006-08-01 00:00:00

  • Metabolic Profiles of Tetrabromobisphenol A in Humans Extrapolated from Humanized-Liver Mouse Data Using a Simplified Physiologically Based Pharmacokinetic Model.

    abstract::Tetrabromobisphenol A, a brominated flame retardant, is increasingly prevalent worldwide and presents a potential health risk. Adjusted animal biomonitoring equivalents of tetrabromobisphenol A after orally administered doses in humanized-liver mice were scaled up to humans using known species allometric scaling facto...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.0c00358

    authors: Miura T,Uehara S,Shigeta K,Yoshizawa M,Kamiya Y,Murayama N,Shimizu M,Suemizu H,Yamazaki H

    更新日期:2020-11-16 00:00:00

  • 42,43,44,45,46,47,55-Heptanor-41-oxohomoyessotoxin, a new biotoxin from mussels of the northern Adriatic sea.

    abstract::The diarrhetic shellfish toxin composition in the digestive glands of mussels from the northern Adriatic sea was investigated. Along with known yessotoxins, identified by comparison of their chromatographic and spectral properties with those reported in the literature, we isolated a new analogue of yessotoxin, 42,43,4...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx000259v

    authors: Ciminiello P,Fattorusso E,Forino M,Poletti R

    更新日期:2001-05-01 00:00:00

  • Assessing the mechanism of metabolism-dependent valproic acid-induced in vitro cytotoxicity.

    abstract::This study was designed to distinguish and evaluate the contribution of reactive metabolite and reactive oxygen species as the mechanism of metabolism-dependent valproic acid-induced in vitro cytotoxicity. The involvement of reactive oxygen species in the mechanism of in vitro cytotoxicity was examined by the addition...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx9801864

    authors: Tabatabaei AR,Thies RL,Abbott FS

    更新日期:1999-04-01 00:00:00

  • Effects of intracerebroventricular administration of 5-(glutathion-S-yl)-alpha-methyldopamine on brain dopamine, serotonin, and norepinephrine concentrations in male Sprague-Dawley rats.

    abstract::alpha-Methyldopamine (alpha-MeDA) is a metabolite of the serotonergic neurotoxicants 3,4-(+/-)-(methylenedioxy)amphetamine (MDA) and 3,4-(+/-)-(methylenedioxy)methamphetamine (MDMA). alpha-MeDA readily oxidizes, and in the presence of glutathione (GSH) it forms 5-(glutathion-S-yl)-alpha-methyldopamine [5-(glutathion-S...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx9501546

    authors: Miller RT,Lau SS,Monks TJ

    更新日期:1996-03-01 00:00:00

  • Identification and characterization of a reaction product of 2'-deoxyoxanosine with glycine.

    abstract::2'-Deoxyoxanosine (dOxo) is a novel DNA lesion produced from dGuo by reaction with nitrous acid or nitric oxide [Suzuki, T., Yamaoka, R., Nishi, M., Ide, H., and Makino, K. (1996) J. Am. Chem. Soc. 118, 2515-2516]. We investigated the reaction of dOxo with glycine (Gly) under physiological conditions. When 5 mM dOxo w...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx990164x

    authors: Suzuki T,Yamada M,Ide H,Kanaori K,Tajima K,Morii T,Makino K

    更新日期:2000-04-01 00:00:00

  • Interaction of trivalent arsenicals with metallothionein.

    abstract::Arsenic is a human carcinogen, causing skin, bladder, and lung cancers. Although arsenic in drinking water affects millions of people worldwide, the mechanism(s) of action by which arsenic causes cancers is not known. Arsenic probably exerts some toxic effects by binding with proteins. However, few experimental data a...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx034053g

    authors: Jiang G,Gong Z,Li XF,Cullen WR,Le XC

    更新日期:2003-07-01 00:00:00

  • Estrogen carcinogenesis: specific identification of estrogen-modified nucleobase in breast tissue from women.

    abstract::Prolonged exposure to estrogens correlates with an increased risk for breast cancer. One explanation is that estrogen metabolites cause mutations by reacting with DNA, leading to depurination. We describe an extraction procedure and a liquid chromatographic tandem mass spectrometric (LC/MS/MS) assay to detect estrone-...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx8001737

    authors: Zhang Q,Aft RL,Gross ML

    更新日期:2008-08-01 00:00:00

  • Application of capillary liquid chromatography coupled with tandem mass spectrometric methods to the rapid screening of adducts formed by the reaction of N-acetoxy-N-acetyl-2-aminofluorene with calf thymus DNA.

    abstract::Capillary liquid chromatography-continuous-flow fast atom bombardment mass spectrometry is applied to the detection of deoxynucleoside adducts of N-acetoxy-N-acetyl-2-aminofluorene. In such a configuration, normal scan and tandem mass spectrometric techniques are shown to provide useful structural information for an N...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00037a013

    authors: Wolf SM,Vouros P

    更新日期:1994-01-01 00:00:00

  • (Carboxyalkyl)pyrroles in human plasma and oxidized low-density lipoproteins.

    abstract::Free-radical oxidation of human plasma low-density lipoprotein (LDL) produces (carboxyalkyl)pyrrole (CAP) epitopes that were detected with enzyme-linked immunosorbent assays using antibodies raised against keyhole limpet hemocyanin (KLH)-bound 2-(omega-carboxyheptyl)-pyrrole (CHP) and 2-(omega-carboxypropyl)pyrrole (C...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx970112c

    authors: Kaur K,Salomon RG,O'Neil J,Hoff HF

    更新日期:1997-12-01 00:00:00

  • Synthesis and characterization of DNA minor groove binding alkylating agents.

    abstract::Derivatives of methyl 3-(1-methyl-5-(1-methyl-5-(propylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)-1H-pyrrol-3-ylamino)-3-oxopropane-1-sulfonate (1), a peptide-based DNA minor groove binding methylating agent, were synthesized and characterized. In all cases, the N-terminus was appended with an O-methyl sulfonate ester, while...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx300437x

    authors: Iyer P,Srinivasan A,Singh SK,Mascara GP,Zayitova S,Sidone B,Fouquerel E,Svilar D,Sobol RW,Bobola MS,Silber JR,Gold B

    更新日期:2013-01-18 00:00:00

  • p,p'-DDE induces apoptosis through the modulation of tumor necrosis factor α in PC12 cells.

    abstract::p,p'-DDE, the main metabolite of DDT, is notorious for its persistent and bioaccumulation. It has detrimental effects on the nervous system, while the mechanism is unclear. We sought to investigate the mechanism of p,p'-DDE-induced neurocytic apoptosis in PC12 cells by cytoflow and screen the potential target gene by ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx4003963

    authors: Wang C,Zhang Q,Qian Y,Zhao M

    更新日期:2014-04-21 00:00:00

  • Hydrolytic Cleavage Products of Globin Adducts in Urine as Possible Biomarkers of Cumulative Dose: Proof of Concept Using Styrene Oxide as a Model Adduct-Forming Compound.

    abstract::A new experimental model was designed to study the fate of globin adducts with styrene 7,8-oxide (SO), a metabolic intermediate of styrene and a model electrophilic compound. Rat erythrocytes were incubated with SO at 7 or 22 °C. Levels of specific amino acid adducts in globin were determined by LC/MS analysis of the ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.5b00518

    authors: Mráz J,Hanzlíková I,Moulisová A,Dušková Š,Hejl K,Bednářová A,Dabrowská L,Linhart I

    更新日期:2016-04-18 00:00:00

  • Lateral Flow Assessment and Unanticipated Toxicity of Kratom.

    abstract::The leaves of the Mitragynine speciosia tree (also known as Kratom) have long been chewed, smoked, or brewed into a tea by people in Southeastern Asian countries, such as Malaysia and Thailand. Just this past year, the plant Kratom gained popularity in the United States as a "legal opioid" and scheduling it as a drug ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.8b00218

    authors: Smith LC,Lin L,Hwang CS,Zhou B,Kubitz DM,Wang H,Janda KD

    更新日期:2019-01-22 00:00:00

  • Glutathione and N-acetylcysteine conjugates of 2-chloroethyl isocyanate. Identification as metabolites of N,N'-bis(2-chloroethyl)-N-nitrosourea in the rat and inhibitory properties toward glutathione reductase in vitro.

    abstract::The antitumor agent N,N'-bis(2-chloroethyl)-N-nitrosourea (BCNU) is known to be unstable in aqueous solution, and to degrade spontaneously to reactive alkylating and carbamoylating intermediates. Whereas the alkylating component is believed to be responsible for the antitumor effects of this drug, it has been speculat...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00033a020

    authors: Davis MR,Kassahun K,Jochheim CM,Brandt KM,Baillie TA

    更新日期:1993-05-01 00:00:00

  • Reactive Sulfur Species-Mediated Activation of the Keap1-Nrf2 Pathway by 1,2-Naphthoquinone through Sulfenic Acids Formation under Oxidative Stress.

    abstract::Sulfhydration by a hydrogen sulfide anion and electrophile thiolation by reactive sulfur species (RSS) such as persulfides/polysulfides (e.g., R-S-SH/R-S-Sn-H(R)) are unique reactions in electrophilic signaling. Using 1,2-dihydroxynaphthalene-4-thioacetate (1,2-NQH2-SAc) as a precursor to 1,2-dihydroxynaphthalene-4-th...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx500416y

    authors: Shinkai Y,Abiko Y,Ida T,Miura T,Kakehashi H,Ishii I,Nishida M,Sawa T,Akaike T,Kumagai Y

    更新日期:2015-05-18 00:00:00

  • The greater reactivity of estradiol-3,4-quinone vs estradiol-2,3-quinone with DNA in the formation of depurinating adducts: implications for tumor-initiating activity.

    abstract::Strong evidence supports the idea that specific metabolites of estrogens, mainly catechol estrogen-3,4-quinones, can react with DNA to become endogenous initiators of breast, prostate, and other human cancers. Oxidation of the catechol estrogen metabolites 4-hydroxyestradiol (4-OHE2) and 2-OHE2 leads to the quinones, ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx050229y

    authors: Zahid M,Kohli E,Saeed M,Rogan E,Cavalieri E

    更新日期:2006-01-01 00:00:00

  • Immunotoxicity induced by acute subtoxic doses of paraquat herbicide: implication of shifting cytokine gene expression toward T-helper (T(H))-17 phenotype.

    abstract::Paraquat (PQ) is a free radical-inducing agent commonly used as an herbicide. This study assesses the acute immunotoxicity of PQ in BALB/c mice and examines its effect on cytokine gene expression profile. It was found that single subtoxic oral doses of 2, 4, and 20 mg/kg significantly inhibited the in vitro mitogen-in...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx300194t

    authors: Hassuneh MR,Albini MA,Talib WH

    更新日期:2012-10-15 00:00:00

  • Synthesis and 32P-postlabeling/high-performance liquid chromatography separation of diastereomeric 1,N2-(1,3-propano)-2'-deoxyguanosine 3'-phosphate adducts formed from 4-hydroxy-2-nonenal.

    abstract::4-Hydroxy-2-nonenal (HNE), a major electrophilic byproduct of lipid peroxidation, is mutagenic and cytotoxic. The two pairs of HNE-derived diastereomeric 1,N2-propanodeoxyguanosine 3'-monophosphate adducts were synthesized from reaction of HNE with 2'-deoxyguanosine 3'-monophosphate. After HPLC separation, these adduc...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx970100r

    authors: Yi P,Zhan D,Samokyszyn VM,Doerge DR,Fu PP

    更新日期:1997-11-01 00:00:00

  • Nucleic acid alkylation by free radical metabolites of ethanol. Formation of 8-(1-hydroxyethyl)guanine and 8-(2-hydroxyethyl)guanine adducts.

    abstract::Alcohol consumption is associated with an increased risk of several types of malignancy by mechanisms that remain to be elucidated. Most of the ingested ethanol is converted to acetaldehyde but the formation of free radical metabolites such as the 1-hydroxyethyl radical has been also demonstrated to occur in vitro and...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx9800351

    authors: Nakao LS,Augusto O

    更新日期:1998-08-01 00:00:00

  • Highly galloylated tannin fractions from witch hazel (Hamamelis virginiana) bark: electron transfer capacity, in vitro antioxidant activity, and effects on skin-related cells.

    abstract::Witch hazel ( Hammamelis virginiana) bark is a rich source of both condensed and hydrolizable oligomeric tannins. From a polyphenolic extract soluble in both ethyl acetate and water, we have generated fractions rich in pyrogallol-containing polyphenols (proanthocyanidins, gallotannins, and gallates). The mixtures were...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx700425n

    authors: Touriño S,Lizárraga D,Carreras A,Lorenzo S,Ugartondo V,Mitjans M,Vinardell MP,Juliá L,Cascante M,Torres JL

    更新日期:2008-03-01 00:00:00

  • Connecting the chemical and biological properties of nitric oxide.

    abstract::Nitric oxide (NO(•); nitrogen monoxide) is known to be a critical regulator of cell and tissue function through mechanisms that utilize its unique physicochemical properties as a small and uncharged free radical with limited reactivity. Here, the basic chemistry and biochemistry of NO(•) are summarized through the des...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章,评审

    doi:10.1021/tx300042g

    authors: Toledo JC Jr,Augusto O

    更新日期:2012-05-21 00:00:00

  • Mapping Chemical Respiratory Sensitization: How Useful Are Our Current Computational Tools?

    abstract::Chemical respiratory sensitization is an immunological process that manifests clinically mostly as occupational asthma and is responsible for 1 in 6 cases of adult asthma, although this may be an underestimate of the prevalence, as it is under-diagnosed. Occupational asthma results in unemployment for roughly one-thir...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.0c00320

    authors: Golden E,Maertens M,Hartung T,Maertens A

    更新日期:2020-12-15 00:00:00

  • Human serum albumin-benzo[a]pyrene anti-diol epoxide adduct structure elucidation by fluorescence line narrowing spectroscopy.

    abstract::Cryogenic (4-10 K) laser-induced vibrationless ground state and vibronic excited state fluorescence emission spectra of the adducts resulting from reaction in vitro of human serum albumin and the carcinogen (+-)-r-7,t-8-dihydroxy-c-9,c-10-epoxy-7,8,9,10- tetrahydrobenzo[a]-pyrene were recorded in order to determine th...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00025a012

    authors: Day BW,Doxtader MM,Rich RH,Skipper PL,Singh K,Dasari RR,Tannenbaum SR

    更新日期:1992-01-01 00:00:00

  • The major metabolite of equilin, 4-hydroxyequilin, autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone.

    abstract::The risk factors for women developing breast and endometrial cancers are all associated with a lifetime of estrogen exposure. Estrogen replacement therapy in particular has been correlated with a slight increased cancer risk. Previously, we showed that equilenin, a minor component of Premarin (Wyeth-Ayerst), was metab...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx980217v

    authors: Zhang F,Chen Y,Pisha E,Shen L,Xiong Y,van Breemen RB,Bolton JL

    更新日期:1999-02-01 00:00:00

  • Ethical guidelines to publication of chemical research. American Chemical Society.

    abstract::The guidelines embodied in this document were revised by the editors of the Publication Division of the American Chemical Society in January 1994 and endorsed by the Society Committee on Publications. ...

    journal_title:Chemical research in toxicology

    pub_type: 指南,杂志文章

    doi:

    authors:

    更新日期:1994-07-01 00:00:00

  • Endocrine disruption screening by protein and gene expression of vitellogenin in freshly isolated and cryopreserved rainbow trout hepatocytes.

    abstract::Xenobiotics may activate the estrogen receptor, resulting in alteration of normal endocrine functions in animals and humans. Consequently, this necessitates development of assay end points capable of identifying estrogenic xenobiotics. In the present study, we screened the potential estrogenicity of chemicals via thei...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx5002089

    authors: Markell LK,Mingoia RT,Peterson HM,Yao J,Waters SM,Finn JP,Nabb DL,Han X

    更新日期:2014-08-18 00:00:00