Isolation of a new okadaic acid analogue from phytoplankton implicated in diarrhetic shellfish poisoning.
AuthorsDraisci R, Giannetti L, Lucentini L, Marchiafava C, James KJ, Bishop AG, Healy BM, Kelly SS
JournalJ Chromatogr A
PubMed ID9542135
A new analogue of okadaic acid (OA), the toxin mainly responsible for diarrhetic shellfish-poisoning (DSP) phenomena in Europe, has been isolated from toxic phytoplankton (Dinophysis acuta) collected in Irish waters. Fluorimetric LC analyses of the extracts of bulk phytoplankton samples using derivatisation with 9-anthryldiazomethane (ADAM) showed a complex toxin profile, ... More
Direct evidence of transformation of dinophysistoxin-1 to 7-O-acyl-dinophysistoxin-1 (dinophysistoxin-3) in the scallop Patinopecten yessoensis.
AuthorsSuzuki T, Ota H, Yamasaki M
JournalToxicon
PubMed ID9920491
'Non-toxic scallops Patinopecten yessoensis were reared for 5 days with the toxic dinoflagellate Dinophysis fortii sampled from the sea. The total cell number ingested by five scallops during the feeding experiment was approximately 682 x 10(3). Okadaic acid (OA), dinophysistoxin-1 (DTX1) and esterified toxins of OA and DTX1 in D. ... More
Development of a selective clean-up method using immobilized antibody and its application to HPLC and GC/MS determination of a carbacyclin derivative, CS-570, in plasma.
AuthorsNakagawa A, Matsushita Y, Muramatsu S, Tanishima Y, Hirota T, Takasaki W, Kawahara Y, Takahagi H
JournalBiomed Chromatogr
PubMed ID3333726
'Methods for the determination of CS-570, a chemically stable prostacyclin analogue, in plasma were developed by using an immobilized antibody column followed by fluorescence HPLC and GC/MS. The CS-570 antibody, obtained from rabbit plasma by giving CS-570-BSA for a few months, was coupled to Sepharose 4B and used as extraction ... More
High-performance liquid chromatographic separation of fluorescent esters of hepoxilin enantiomers on a chiral stationary phase.
AuthorsDemin P, Reynaud D, Pace-Asciak CR
JournalJ Chromatogr B Biomed Appl
PubMed ID8581135
'Fluorescent anthryl (ADAM) derivatives of hepoxilins have been shown to possess good chromatographic properties affording good sensitivity for the high-performance liquid chromatographic analysis and detection of these compounds and related eicosanoids (12-hydroxyeicosatetraenoic acid) in biological samples. We report herein the separation of all possible stereoisomers of hepoxilins A3 and B3 ... More
Further studies on the analysis of DSP toxin profiles in galician mussels.
AuthorsComesaña Losada M, Leão JM, Gago-Martínez A, Rodríguez Vázquez JA, Quilliam MA
JournalJ Agric Food Chem
PubMed ID10563941
'Further studies on mussel samples from Galicia, Spain, have revealed the presence of okadaic acid (OA), dinophysistoxin 2 (DTX2), and the fatty acid acyl esters of both of these toxins as the "DTX3" complex. Measurements were performed with an improved in situ method for the formation of 9-anthryldiazomethane (ADAM) derivatives ... More
Pectenotoxin-2 seco acid, 7-epi-pectenotoxin-2 seco acid and pectenotoxin-2 in shellfish and plankton from Portugal.
AuthorsVale P, de M Sampayo MA
JournalToxicon
PubMed ID12076652
'Pectenotoxin-2 seco acid (PTX2sa) and 7-epi-pectenotoxin-2 seco acid (7-epi-PTX2sa) were found in Portuguese shellfish both by fluorescence detection after ADAM derivatisation and, liquid chromatography coupled with mass spectrometry detection. Two time-series both with blue mussel (Mytilus edulis) and common cockle (Cerastoderma edule) from Aveiro lagoon illustrate how PTX2sa has a ... More
Screening method for phenoxy acid herbicides in ground water by high-performance liquid chromatography of 9-anthryldiazomethane derivatives and fluorescence detection.
AuthorsSuzuki T, Watanabe S
JournalJ Chromatogr
PubMed ID2037653
'A high-performance liquid chromatographic (HPLC) method for phenoxy acid herbicides using precolumn derivatization with 9-anthryldiazomethane (ADAM) is presented. The phenoxy acid herbicides investigated were (2,4-dichlorophenoxy)acetic acid, (4-chloro-2-methylphenoxy)acetic acid, 2-(4-chloro-2-methylphenoxy)propionic acid and (4-chloro-2-methylphenoxy)butyric acid. These herbicides reacted with ADAM under mild conditions and were converted into the corresponding fluorescent derivatives. The ... More
Improved method for preparation and use of 9-anthryldiazomethane for derivatization of hydroxycarboxylic acids. Application to diarrhetic shellfish poisoning toxins.
AuthorsQuilliam MA, Gago-Martínez A, Rodríguez-Vázquez JA
JournalJ Chromatogr A
PubMed ID9646498
'Application of a method for the "in situ" generation of 9-anthryldiazomethane (ADAM) to the derivatization of the carboxyl function in diarrhetic shellfish poisoning (DSP) toxins revealed the formation of artifact products. Using liquid chromatography-mass spectrometry, it was determined that these artifacts were due to base-catalyzed reactions between the solvent, ethyl ... More
Quantitative determination of a potent lipopolysaccharide antagonist, E5564, in rat and dog plasma by high-performance liquid chromatography with fluorescence detection.
AuthorsKaneko K, Ueda R, Kikuchi K, Sano Y, Yoshimura T
JournalJ Chromatogr B Biomed Sci Appl
PubMed ID10676985
'The assay method was established for the quantification of a potent lipopolysaccharide (LPS) antagonist, E5564, in rat and dog plasma using HPLC. E5564 and the I.S. (an analogue of E5564) were extracted and derivatized with 9-Anthryldiazomethane (ADAM reagent) to be given fluorescence. LC-MS analysis indicated that single molecule of E5564 ... More
Investigation of derivatization reagents for the analysis of diarrhetic shellfish poisoning toxins by liquid chromatography with fluorescence detection.
AuthorsMarr JC, McDowell LM, Quilliam MA
JournalNat Toxins
PubMed ID7866666
'Several derivatization reagents for the conversion of okadaic acid and related DSP toxins to fluorescent derivatives for analysis by liquid chromatography have been examined, viz: 9-anthryldiazomethane (ADAM), 1-pyrenyldiazomethane (PDAM), 4-diazomethyl-7-methoxycoumarin (DMMC), 4-bromomethyl-7-methoxycoumarin (BrMMC), 4-bromomethyl-7,8-benzcoumarin (BrMBC), 4-bromomethyl-7-acetoxycoumarin (BrMAC), and 4-bromomethyl-6,7-dimethoxycoumarin (BrDMC). The ADAM reagent provides the greatest selectivity and sensitivity, but ... More
Reverse-phase high-performance liquid chromatographic assay of phospholipases: application of spectrophotometric detection to rat phospholipase A2 isozymes.
AuthorsTojo H, Ono T, Okamoto M
JournalJ Lipid Res
PubMed ID8509721
'This paper appraises an HPLC method for assaying phospholipase A2 (PLA2). The procedure is based on heptane-isopropanol-H2SO4 extraction of fatty acids released by the enzyme in the presence of margaric acid as an internal standard, and precolumn derivatization with 9-anthryldiazomethane. The derivatives of naturally occurring long-chain fatty acids were accurately ... More
Studies on the detection of okadaic acid in mussels: preliminary comparison of bioassays.
AuthorsMarcaillou-Le Baut C, Amzil Z, Vernoux JP, Pouchus YF, Bohec M, Simon JF
JournalNat Toxins
PubMed ID7866667
'Diarrheic toxins, especially okadaic acid, are detected nearly every year in mussels on French coasts. The monitoring network determines the toxicity of these shellfish by using a mouse test now considered unsatisfactory from an ethical point of view. Two alternative methods have been investigated: the daphnia test, for which there ... More
The repeatability of two HPLC methods and the PP2A assay in the quantification of diarrhetic toxins in blue mussels (Mytilus edulis).
AuthorsRamstad H, Larsen S, Aune T
JournalToxicon
PubMed ID11024492
'Repeatability in the quantification of diarrhetic shellfish toxins was investigated for two fluorometric HPLC methods and a colorimetric PP2A assay, using agreement analysis. Blue mussels (Mytilus edulis) from the Sognefjord on the southwest coast of Norway were sampled during the periods of July to October, 1996, March to November, 1997, ... More
Endogenous alpha-ketol linolenic acid levels in short day-induced cotyledons are closely related to flower induction in Pharbitis nil.
AuthorsSuzuki M, Yamaguchi S, Iida T, Hashimoto I, Teranishi H, Mizoguchi M, Yano F, Todoroki Y, Watanabe N, Yokoyama M
JournalPlant Cell Physiol
PubMed ID12552145
'Alpha-ketol linolenic acid [KODA, 9,10-ketol-octadecadienoic acid, that is 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid] is a signal compound found in Lemna paucicostata after exposure to stress, such as drought, heat or osmotic stress. KODA reacts with catecholamines to generate products that strongly induce flowering, although KODA itself is inactive [Yokoyama et al. (2000) Plant ... More
Prostaglandin production in response to a bacterial infection in true armyworm larvae
AuthorsJurenka RA, Pedibhotla VK, Stanley DW
JournalArch Insect Biochem Physiol
PubMed ID10421896
'Prostaglandin levels were determined by fluorometric HPLC analysis of hemolymph collected from larvae of the true armyworm, Pseudaletia unipuncta, that had been injected with bacteria. Prostaglandins were extracted and derivatized with the fluorogenic compound 9-anthryldiazomethane and detected by fluorescence-HPLC. One of the prostaglandins produced was identified as prostaglandin F(2alpha) based ... More
Quantitative HPLC analysis of acids in Brazilian cachaças and various spirits using fluorescence detection of their 9-anthrylmethyl esters.
AuthorsFerreira Do Nascimento R, Rodrigues Cardoso D, De Keukeleire D, dos Santos Lima-Neto B, Wagner Franco D
JournalJ Agric Food Chem
PubMed ID11312779
'An analytical procedure for the separation and quantification of 17 short-chain, medium-chain, and long-chain acids in cachaças and various spirits has been developed involving C18 solid phase extraction, derivatization with 9-anthryldiazomethane, and reverse phase HPLC using fluorescence detection. The limit of detection was between 5 and 15 fmol, whereas the ... More
Okadaic acid production from the marine benthic dinoflagellate Prorocentrum arenarium Faust (Dinophyceae) isolated from Europa Island coral reef ecosystem (SW Indian Ocean).
AuthorsTen-Hage L, Delaunay N, Pichon V, Couté A, Puiseux-Dao S, Turquet J
JournalToxicon
PubMed ID10708796
'Okadaic acid was isolated from a strain of Prorocentrum arenarium Faust (Prorocentrales, Dinophyceae) collected from Europa Island (40 degrees 22''E, 22 degrees 20''S, SW Indian Ocean). The presence of okadaic acid in the algal extract was suspected after cytotoxicity and phosphatase 2A inhibition testing. It was confirmed by ADAM derivatization, ... More
Determination of carnitine by high-performance liquid chromatography using 9-anthryldiazomethane.
AuthorsYoshida T, Aetake A, Yamaguchi H, Nimura N, Kinoshita T
JournalJ Chromatogr
PubMed ID3215969
'The high-performance liquid chromatographic determination of carnitine chloride was investigated by using 9-anthryldiazomethane (ADAM) as a pre-column derivatization reagent. Carnitine chloride and the internal standard N,N-dimethylglycine reacted with ADAM to give a stable ester derivative in the presence of sodium dodecyl sulphate (SDS) used to mask the basic function. The ... More
Comparison of eicosanoids production between rat polymorphonuclear leukocytes and macrophages: detection by high-performance liquid chromatography with precolumn fluorescence labeling.
AuthorsYamaki K, Oh-ishi S
JournalJpn J Pharmacol
PubMed ID1513077
'We developed a procedure for serial measurement of fluorescent derivatives of eicosanoids in biological samples by HPLC. The 9-anthryldiazomethane (ADAM)-derivatized sample was first fractionated through SEP-PAK silica into fraction 1 (eluate of chloroform:toluene) and fraction 2 (eluate of acetonitrile:methanol). Both fractions were loaded separately onto an ODS column, and eluted ... More
Quantitative determination of prostaglandin levels in human gastric mucosa--analysis by microcolumn high performance liquid chromatography with laser induced fluorescence detection.
AuthorsGoto H, Sugiyama S, Kawabe Y, Kuroiwa M, Ohara A, Tsukamoto Y, Nakazawa S, Ozawa T
JournalBiochem Int
PubMed ID2369414
'This study was designed to analyze PGs in human gastric mucosa using biopsy specimens at femtomole level by the combination of microcolumn HPLC and He/Cd laser induced fluorescence detection. Biopsy specimens were taken along the greater curvature at the corpus of the stomach, in which no gastric disease was revealed ... More
Quantitative determination of the fatty acid composition of human serum lipids by high-performance liquid chromatography.
AuthorsShimomura Y, Sugiyama S, Takamura T, Kondo T, Ozawa T
JournalJ Chromatogr
PubMed ID3818849
'A high-performance liquid chromatographic method for the analysis of the fatty acid composition of human serum lipids with fluorescence detection was examined. Both free and total fatty acids extracted from serum were derivatized with 9-anthryldiazomethane and were analysed using methanol-water (94.7:5.3) as mobile phase. Twelve kinds of fatty acid were ... More
Variations in the distribution of okadaic acid in organs and biological fluids of mice related to diarrhoeic syndrome.
AuthorsMatias WG, Traore A, Creppy EE
JournalHum Exp Toxicol
PubMed ID10372758
'Okadaic acid (OA) is the main toxin produced by dinoflagellates which can accumulate in the hepatopancreas of mussels and cause diarrhetic shellfish poisoning in consumers. This toxin is also a tumour promoter and a specific potent inhibitor of protein phosphatases 1 and 2A. No specific target organ is known for ... More
Rapid assay of N-butyl-N-(3-carboxypropyl)nitrosamine in rat organs and urine by high-performance liquid chromatography after derivatization.
AuthorsWada S, Funae Y, Imaoka S, Kawamura M, Kinoshita Y, Sugimoto T, Nishio S, Kishimoto T, Maekawa M
JournalJpn J Cancer Res
PubMed ID3922837
'The concentration of N-butyl-N-(3-carboxypropyl)nitrosamine (BCPN), which is the major metabolite of the carcinogen N-butyl-N-(4-hydroxybutyl)nitrosamine (BBN), was measured in the urine, thymus, liver, kidney, and bladder of rats orally administered with BBN. Since BCPN is a carboxylic acid, it forms an ester with 9-anthryldiazomethane (ADAM), which is a fluorescent labeling agent ... More
Physicochemical and immunochemical properties of recombinant human serum albumin from Pichia pastoris.
AuthorsOhtani W, Nawa Y, Takeshima K, Kamuro H, Kobayashi K, Ohmura T
JournalAnal Biochem
PubMed ID9466797
'We analyzed and compared the physicochemical and immunochemical properties of recombinant human serum albumin (rHSA) from Pichia pastoris with those of plasma-derived human serum albumin (pHSA). The second virial coefficient of rHSA, obtained from colloid osmotic pressure measurements at pH 6.7 +/- 0.1 was not significantly different from that of ... More
[A highly sensitive assay method of oxalic acid in human plasma using high performance liquid chromatography with fluorescent labeling reagent]
AuthorsShimizu K, Nagase H, Araki H
JournalYakugaku Zasshi
PubMed ID2754617
'An assay method for the plasma level of oxalic acid (OA) was developed by using high-performance liquid chromatography (HPLC). Low molecular weight carboxylic acids including OA were separated from interfering plasma components by passing through ultrafilter (Centriflow CF 25, Amicon) and a Sep-Pak C18 cartridge (Waters), and OA was extracted ... More
Segregated coupling of phospholipases A2, cyclooxygenases, and terminal prostanoid synthases in different phases of prostanoid biosynthesis in rat peritoneal macrophages.
AuthorsNaraba H, Murakami M, Matsumoto H, Shimbara S, Ueno A, Kudo I, Oh-ishi S
JournalJ Immunol
PubMed ID9510202
'We examined herein the functional linkage of enzymes regulating the initial, intermediate, and terminal steps of PG biosynthesis to provide PGs in rat peritoneal macrophages stimulated with LPS and/or A23187. Quiescent cells stimulated with A23187 produced thromboxane B2 (TXB2) in marked preference to PGE2 within 30 to 60 min (constitutive ... More
Liquid chromatographic determination of monensin in chicken tissues with fluorometric detection and confirmation by gas chromatography-mass spectrometry.
AuthorsTakatsuki K, Suzuki S, Ushizawa I
JournalJ Assoc Off Anal Chem
PubMed ID3722091
'An accurate, sensitive method is described for the determination of monensin residue in chicken tissues by liquid chromatography (LC), in which monensin is derivatized with a fluorescent labeling reagent, 9-anthryldiazomethane (ADAM), to enable fluorometric detection. Samples are extracted with methanol-water (8 + 2), the extract is partitioned between CHCl3 and ... More
Determination of free biotin in plasma by liquid chromatography with fluorimetric detection.
AuthorsHayakawa K, Oizumi J
JournalJ Chromatogr
PubMed ID3558675
9-Diazomethylanthracene as a new fluorescence and ultraviolet label for the spectrometric detection of picomole quantities of fatty acids by high-pressure liquid chromatography.
AuthorsBarker SA, Monti JA, Christian ST, Benington F, Morin RD
JournalAnal Biochem
PubMed ID7435947
9-Anthryldiazomethane-HPLC method for detection of prostaglandins and thromboxane: an application to the measurement of the products of stimulated rabbit platelets.
AuthorsYamaki K, Oh-ishi S
JournalChem Pharm Bull (Tokyo)
PubMed ID3791527
Separation of the 9-anthryldiazomethane derivates of fatty acids by high-performance liquid chromatography on a Fatty Acid Analysis Column. Application to albumin-bound fatty acid analysis.
The latest trends in the labeling of free carboxyl groups for high-performance liquid chromatography are reviewed. The labeling reagents for fluorescence detection are mainly discussed according to their reaction type (or functional group). Attention is also paid to the reagents used for ultraviolet detection and for enantiomeric separation. The reactivity ... More
Automatic high-performance liquid chromatographic method for the determination of diarrhetic shellfish poison.
AuthorsHummert C, Shen JL, Luckas B
JournalJ Chromatogr A
PubMed ID9004963
A rapid HPLC method with fluorescence detection for the determination of okadaic acid (OA) and dinophysistoxin-1 (DTX-1) in mussels and mussel products is presented. For fluorescence labelling of OA and DTX-1, 9-anthryldiazomethane (ADAM) is used. HPLC with a column-switching system is proposed to avoid time-consuming clean-up procedures after derivatization of ... More
Microanalysis of free fatty acids in plasma of experimental animals and humans by high-performance liquid chromatography.
AuthorsHatsumi M, Kimata S, Hirosawa K
JournalJ Chromatogr
PubMed ID3760054
A high-performance liquid chromatographic (HPLC) method was developed for microanalysis of thirteen free fatty acids using 200 microliter of plasma. Fatty acids were derivatized with 9-anthryldiazomethane for HPLC analysis. Use of an ODS minicolumn for pretreatment of plasma gave a more accurate determination of free fatty acids in plasma than ... More
Ultraviolet and fluorescence derivatization reagents for carboxylic acids suitable for high performance liquid chromatography: a review.
AuthorsMukherjee PS, Karnes HT
JournalBiomed Chromatogr
PubMed ID8879524
Pre- and postcolumn derivatization with a suitable chromophore or fluorophore have often been utilized to enhance the sensitivity and selectivity of detection for analytes possessing a carboxyl group. The major classes of UV and fluorescent derivatization reagents include the coumarin analogues, alkyl halides, diazoalkanes, and amines. The derivatization reaction conditions, ... More
Comparison of dinophysistoxin-1 and esterified dinophysistoxin-1 (dinophysistoxin-3) contents in the scallop Patinopecten yessoensis and the mussel Mytilus galloprovincialis.
AuthorsSuzuki T, Mitsuya T
JournalToxicon
PubMed ID11137552
Okadaic acid (OA) homologues in toxic dinoflagellate Dinophysis fortii, scallops Patinopecten yessoensis and mussels Mytilus galloprovincialis collected at the same site in Mutsu Bay, Japan were determined by high-performance liquid chromatography fluorescence detection (HPLC-FLD) as their 9-anthryldiazomethane (ADAM) derivatives. Prominent toxin in the scallops and the mussels was esterified dinophysistoxin-1 ... More
Transplacental passage of [3H]-okadaic acid in pregnant mice measured by radioactivity and high-performance liquid chromatography.
AuthorsMatias WG, Creppy EE
JournalHum Exp Toxicol
PubMed ID8839210
Okadaic acid (OA) is the main toxin produced by dinoflagellates, which can accumulate in the hepatopancreas of mussels and cause diarrhoetic shellfish poisoning in consumers. This toxin is also a tumour promoter and a specific potent inhibitor of protein phosphatases 1 and 2A. The results in this study show for ... More
A high-performance liquid chromatographic method for the determination of polyphosphoinositides in brain.
AuthorsNakamura T, Hatori Y, Yamada K, Ikeda M, Yuzuriha T
JournalAnal Biochem
PubMed ID2547321
A simple high-performance liquid chromatographic method for the determination of endogenous phosphatidylinositol 4-phosphate (PIP) and phosphatidylinositol 4,5-bisphosphate (PIP2) in brain has been developed. PIP and PIP2 were derivatized with 9-anthryldiazomethane to yield (9-anthryl)PIP and di(9-anthryl)-PIP2. The derivatives were separated on a reversed-phase column using isocratic elution and detected with a ... More
High-performance liquid chromatographic analysis of arachidonic acid metabolites by pre-column derivatization using 9-anthryldiazomethane.
AuthorsYamauchi Y, Tomita T, Senda M, Hirai A, Terano T, Tamura Y, Yoshida S
JournalJ Chromatogr
PubMed ID3711183
Arachidonic acid (AA) metabolites produced by washed human platelets and rat macrophages were analyzed by high-performance liquid chromatography (HPLC) using a pre-column derivatization method. The reagent, 9-anthryldiazomethane, used in this study and AA metabolites derivatized by the reagent were purified by gel permeation chromatography (PG-pak C column), prior to normal-phase ... More
Derivatization reactions for neurotransmitters and their automation.
AuthorsBovingdon ME, Webster RA
JournalJ Chromatogr B Biomed Appl
PubMed ID7820275
Many reagents suitable for the derivatization of neurotransmitters are selective for the amino function. Others, however, are selective for the carboxyl-, thiol- and hydroxyl function, and recently, reagents selective for more than one function have been produced. Interest persists in the established reagents, with their well understood behaviour which assists ... More
Determination of free fatty acids in human bile by high-performance liquid chromatography.
AuthorsHori Y, Nakamura K, Yamamoto M, Shimada K, Nakadaira H, Shibuya N, Endoh K, Ogoshi K
JournalAnn Clin Biochem
PubMed ID9547901
We developed a high-performance liquid chromatography (HPLC) method for free fatty acids (FFAs) analysis in bile. In this method, FFAs were extracted from bile in a single step using an Isolute ODS cartridge, derivatized with 9-anthryldiazomethane (ADAM). ADAM was chosen because of its high reactivity with carboxylic acid at room ... More
Highly sensitive determination of imidapril, a new angiotensin I-converting enzyme inhibitor, and its active metabolite in human plasma and urine using high-performance liquid chromatography with fluorescent labelling reagent.
AuthorsTagawa K, Hayashi K, Mizobe M, Noda K
JournalJ Chromatogr
PubMed ID8376543
A method for the simultaneous determination of imidapril and its active metabolite in human plasma and urine has been developed using high-performance liquid chromatography with a fluorescent labelling reagent, 9-anthryldiazomethane. Imidapril and its active metabolite were extracted from human plasma and urine using a solid-phase extraction cartridge (Bond Elut C18). ... More
Liquid chromatographic determination of okadaic acid and dinophysistoxin-1 in shellfish after derivatization with 9-chloromethylanthracene.
AuthorsLawrence JF, Roussel S, Ménard C
JournalJ Chromatogr A
PubMed ID8611946
The reagent 9-chloromethylanthracene was evaluated for derivatization of the diarrhetic shellfish poisons, okadaic acid and dinophysistoxin-1 (DTX-1), to form fluorescent products separable by liquid chromatography. The toxins were reacted with the reagent in acetonitrile in the presence of tetramethylammonium hydroxide for 1 h at 90 degrees C. The products were ... More
Simultaneous determination of 2,4-D and MCPA in canine plasma and urine by HPLC with fluorescence detection using 9-anthryldiazomethane (ADAM).
AuthorsDickow LM, Gerken DF, Sams RA, Ashcraft SM
JournalJ Anal Toxicol
PubMed ID11215998
A method for the simultaneous determination of 2,4-dichlorophenoxyacetic acid (2,4-D) and 2-methyl-4-chlorophenoxyacetic acid (MCPA) in canine plasma and urine has been developed. This method used derivatization of extracted samples with 9-anthrylmethane (ADAM) for analysis by reversed-phase high-performance liquid chromatography with fluorescence detection. Precision and accuracy were within the accepted limits ... More
Specific and rapid assay of urinary oxalic acid using high-performance liquid chromatography.
AuthorsImaoka S, Funae Y, Sugimoto T, Hayahara N, Maekawa M
JournalAnal Biochem
PubMed ID6846821
A high-performance liquid chromatographic (HPLC) method was developed to determine the levels of oxalic acid in the urine. This acid was extracted from urine with tri-n-butyl phosphate and converted into the fluorescent derivative by esterification with 9-anthryldiazomethane (ADAM). The reaction mixture containing the oxalic acid derivative can be directly chromatographed ... More
New preparation method for 9-anthryldiazomethane (ADAM) as a fluorescent labeling reagent for fatty acids and derivatives.
AuthorsYoshida T, Uetake A, Yamaguchi H, Nimura N, Kinoshita T
JournalAnal Biochem
PubMed ID3189804
A preparation method for 9-anthryldiazomethane (ADAM) as a fluorescent labeling reagent for carboxylic acids is described. 9-Anthraldehyde hydrazone is oxidized with an organic oxidant, N-chlorosuccinimide, in an organic solvent such as ethyl acetate to give ADAM, and then the reaction mixture is directly used as the reagent solution for the ... More
Molecular cloning and expression of fatty acid alpha-hydroxylase from Sphingomonas paucimobilis.
AuthorsMatsunaga I, Yokotani N, Gotoh O, Kusunose E, Yamada M, Ichihara K
JournalJ Biol Chem
PubMed ID9295298
Fatty acid alpha-hydroxylase (FAAH) catalyzes the initial reaction in alpha-oxidation of fatty acid to produce 2-hydroxy fatty acid. FAAH activity has been detected in a wide range of organisms from prokaryotes to eukaryotes. Here, we describe cloning of the FAAH gene from Sphingomonas paucimobilis, a sphingolipid- and 2-hydroxymyristic acid-rich bacterium. ... More
Isolation of dinophysistoxin-2 and the high-performance liquid chromatographic analysis of diarrhetic shellfish toxins using derivatisation with 1-bromoacetylpyrene.
AuthorsKelly SS, Bishop AG, Carmody EP, James KJ
JournalJ Chromatogr A
PubMed ID8921593
The rare diarrhetic shellfish toxin, dinophysistoxin-2 (DTX-2), was isolated from the digestive glands of mussels (Mytilus edulis). This was achieved by chromatography on silica and Sephadex LH-20 followed by reversed-phase solid phase extraction and semi-preparative high-performance liquid chromatography (HPLC) with an Ultremex C18 column. Using 1-bromoacetylpyrene (BAP), as a precolumn ... More
Fluorogenic reactions for biomedical chromatography.
AuthorsOhkura Y, Kai M, Nohta H
JournalJ Chromatogr B Biomed Appl
PubMed ID7820282
A number of fluorogenic reactions, which have been used for HPLC detection systems by means of pre- and/or postcolumn derivatization, are surveyed with respect to both sensitivity and selectivity for the determination of biomedically important substances. For the derivatization of the substances, two types of fluorogenic reactions, fluorescence-generating and fluorescence-tagging, ... More
A phospholipase A2 in the supernatant fraction of rat spleen. Its similarity to rat pancreatic phospholipase A2.
AuthorsTojo H, Ono T, Kuramitsu S, Kagamiyama H, Okamoto M
JournalJ Biol Chem
PubMed ID3128547
Rat spleen supernatant contained two forms of calcium-dependent cellular phospholipase A2 which could be separated from each other by TEAE-cellulose chromatography. The phospholipase A2, named PLA2 S-1, present in the major flow-through fraction was purified to homogeneity. The structural and catalytic properties of splenic PLA2 S-1 were systematically compared with ... More
Interference of free fatty acids from the hepatopancreas of mussels with the mouse bioassay for shellfish toxins.
AuthorsSuzuki T, Yoshizawa R, Kawamura T, Yamasaki M
JournalLipids
PubMed ID8784745
Determination of free fatty acids (FFA) in hepatopancreas of mussel, Mytilus coruscus, contaminated by diarrhetic shellfish poisoning (DSP) toxins, was carried out by high-performance liquid chromatography-fluorometry as their 9-anthryldiazomethane derivatives. The FFA in the hepatopancreas of mussels during May 30-June 14 were 443-666 micrograms/g. A marked increase in FFA content ... More
Microidentification of N-terminal-blocked amino acid residues of proteins and peptides.
AuthorsKawakami Y, Ohmori S
JournalAnal Biochem
PubMed ID7978259
Proteins or peptides having an N-terminal-blocked amino acid were successively digested by pronase E, proteinase K, and carboxypeptidase Y. The N-blocked amino acids released from proteins or peptides were derivatized with 9-anthryldiazomethane (ADAM) to the corresponding esters followed by addition of formic acid to remove the remaining ADAM which interfered ... More
A fluorescent microplate assay for diarrheic shellfish toxins.
AuthorsVieytes MR, Fontal OI, Leira F, Baptista de Sousa JM, Botana LM
JournalAnal Biochem
PubMed ID9177752
A fluorescent enzyme inhibition assay for okadaic acid using 4-methylumbelliferyl phosphate and fluorescein diphosphate as substrates for the enzyme phosphatase 2A was developed. In the inhibition assay, performed in a microtiter plate, the PP2A was inhibited by adding okadaic acid and the resulting fluorescence enhancement derived from enzymatic hydrolysis of ... More
Separation and quantitation of long-chain free fatty acids in human serum by high-performance liquid chromatography.
AuthorsKargas G, Rudy T, Spennetta T, Takayama K, Querishi N, Shrago E
JournalJ Chromatogr
PubMed ID2361977
A rapid, simple and highly sensitive reversed-phase high-performance liquid chromatographic method is described for the separation and quantitation of fatty acids in human serum using a very reactive fluorescent labeling reagent, 9-anthryldiazomethane. Quantitative esterification proceeds at room temperature without heat or catalysis. Baseline separation of nineteen select fatty acids from ... More
Liquid chromatographic determination of multiresidue fluorescent derivatives of ionophore compounds, monensin, salinomycin, narasin, and lasalocid, in beef liver tissue.
AuthorsMartinez EE, Shimoda W
JournalJ Assoc Off Anal Chem
PubMed ID3745090
A liquid chromatographic (LC) method with fluorometric detection was developed to quantitatively determine residue levels of monensin, salinomycin, narasin, and lasalocid in beef liver tissue. The ionophores are extracted from the tissue, purified by both alumina and Sephadex LH-20 column chromatography, and then derivatized. Lasalocid was directly esterified with 9-anthryldiazomethane ... More
Effect of 13-hydroperoxyoctadecadienoic acid on the supply of arachidonic acid for prostaglandin synthesis from arachidonoyl-CoA mediated by the cytosolic or microsomal acyl-CoA hydrolase in rabbit kidney medulla.
AuthorsSakuma S, Fujimoto Y, Yoshimura M, Saeki K, Mukai A, Akimoto M, Fujita T
JournalIUBMB Life
PubMed ID10637771
The effects of 13-hydroperoxyoctadecadienoic acid (13-HPODE) on the cytosolic or microsomal acyl-CoA hydrolase (ACH) activity in rabbit kidney medulla and on the ACH-mediated prostaglandin (PG) formation from arachidonoyl-CoA (AA-CoA) were examined. 13-HPODE (10, 20, and 50 microM) had no effect on the cytosolic ACH activity but significantly inhibited the activity ... More
Diarrhetic shellfish toxins: improvement of sample clean-up for HPLC determination.
AuthorsStabell OB, Hormazabal V, Steffenak I, Pedersen K
JournalToxicon
PubMed ID2028473
Okadaic acid and dinophysistoxin-1, the principal toxic components in diarrhetic shellfish poisoning, may be detected by high-performance liquid chromatography and fluorometric measurement as 9-anthrylmethyl esters. However, "greasy" samples may occur and the fluorescent reagent 9-anthryldiazomethane may decompose during storage, resulting in impurities that may seriously interfere with quantitative determination. Ultrasonic ... More
Determination of the amounts of free arachidonic acid in resident and activated rabbit alveolar macrophages by fluorometric high performance liquid chromatography.
AuthorsNakagawa Y, Waku K
JournalLipids
PubMed ID3928997
An improved method of high performance liquid chromatography (HPLC) has been developed for the separation and quantitation of low levels of free fatty acids as they occur in mammalian tissues. The fatty acid analysis is based on the esterification of the carboxylic group with 9-anthryldiazomethane (ADAM). HPLC separation and fluorescence ... More
Phorbol myristate acetate-stimulated release of cyclooxygenase products in rat pleural cells: derivatization of prostaglandins with 9-anthryldiazomethane for fluorometric determination by high performance liquid chromatography.
AuthorsKiyomiya K, Yamaki K, Nimura N, Kinoshita T, Oh-ishi S
JournalProstaglandins
PubMed ID3081970
White cells were collected from the wash of rat pleural cavity after exsanguination. The incubation mixture of the pleural cells with 1 microM phorbol myristate acetate (PMA) was extracted with acidified ethanol and purified with a Sep-pak C18. The resultant fraction containing prostaglandins (PG) and thromboxane (TX) was allowed to ... More
Fluorescent HPLC assay for 20-HETE and other P-450 metabolites of arachidonic acid.
AuthorsMaier KG, Henderson L, Narayanan J, Alonso-Galicia M, Falck JR, Roman RJ
JournalAm J Physiol Heart Circ Physiol
PubMed ID10924088
This study describes a fluorescent HPLC assay for measuring 20-hydroxyeicosatetraenoic acid (20-HETE) and other cytochrome P-450 metabolites of arachidonic acid in urine, tissue, and interstitial fluid. An internal standard, 20-hydroxyeicosa-6(Z),15(Z)-dienoic acid, was added to samples, and the lipids were extracted and labeled with 2-(2,3-naphthalimino)ethyl trifluoromethanesulfonate. P-450 metabolites were separated on ... More
Arachidonic acid as a messenger for the expression of long-term potentiation.
AuthorsNishizaki T, Nomura T, Matsuoka T, Tsujishita Y
JournalBiochem Biophys Res Commun
PubMed ID9918858
Arachidonic acid is suggested to play a role in the expression of long-term potentiation (LTP), a synaptic analog of memory and learning. However, it is unknown whether this free fatty acid is actually released during LTP or not. To address this question, we assayed arachidonic acid with an HPLC system ... More
Phospholipase A2 is not responsible for lysophosphatidylcholine-induced damage in cardiomyocytes.
AuthorsChen M, Xiao CY, Hashizume H, Abiko Y
JournalAm J Physiol
PubMed ID9815086
Lysophosphatidylcholine (LPC) is known to increase the intracellular concentration of Ca2+ ([Ca2+]i), leading to cell damage. In the present study we examined whether LPC activates phospholipase A2 (PLA2) and whether the activation of PLA2 is responsible for the LPC-induced cell damage in isolated rat cardiomyocytes. LPC (15 microM) produced an ... More
Lisofylline prevents leak, but not neutrophil accumulation, in lungs of rats given IL-1 intratracheally.
AuthorsHybertson BM, Bursten SL, Leff JA, Lee YM, Jepson EK, Dewitt CR, Zagorski J, Cho HG, Repine JE
JournalJ Appl Physiol
PubMed ID9029220
Interleukin-1 (IL-1) is increased in lung lavages from patients with the acute respiratory distress syndrome, and administering IL-1 intratracheally causes neutrophil accumulation and a neutrophil-dependent oxidative leak in lungs of rats. In the present study, we found that rats pretreated intraperitoneally with lisofylline [(R)-1-(5-hydroxyhexyl)-3, 7-dimethylxanthine (LSF)], an inhibitor of lysophosphatidic ... More
Extractive derivatization of the 12-lipoxygenase products, hepoxilins, and related compounds into fluorescent anthryl esters for their complete high-performance liquid chromatography profiling in biological systems.
AuthorsDemin P, Reynaud D, Pace-Asciak CR
JournalAnal Biochem
PubMed ID7793626
Facile methods for the detection of intact hepoxilins, monohydroxy-epoxide derivatives of arachidonic acid formed through the 12-lipoxygenase pathway, are unavailable because (i) an absence in these compounds of an appropriate chromophore for sensitive detection by uv exists, (ii) these compounds are sensitive to the acidic workup leading to varying degrees ... More
Stimulation of prostaglandin E2 synthesis in cloned osteoblastic cells of mouse (MC3T3-E1) by epidermal growth factor.
AuthorsYokota K, Kusaka M, Ohshima T, Yamamoto S, Kurihara N, Yoshino T, Kumegawa M
JournalJ Biol Chem
PubMed ID3096986
Prostaglandin (PG) E2, known as a bone-resorption factor, was released as a predominant arachidonate metabolite in the culture medium of an osteoblastic cell line cloned from mouse calvaria (MC3T3-E1). Epidermal growth factor (EGF) (10 ng/ml) prominently enhanced endogenous PGE2 synthesis, requiring the simultaneous presence of unidentified factor(s) contained in bovine ... More
Clofibrate-inducible rat hepatic P450s IVA1 and IVA3 catalyze the omega- and (omega-1)-hydroxylation of fatty acids and the omega-hydroxylation of prostaglandins E1 and F2 alpha.
Cytochromes P450IVA1 and IVA3 display 72% amino acid sequence similarity and are expressed in livers of rats treated with the hypolipidemic drug clofibrate. The catalytic activities of IVA1 and IVA3 were examined by cDNA-directed expression using vaccinia virus. cDNA-expressed IVA1 and IVA3 had relative Mrs of 51,500 and 52,000, respectively, ... More
Tumor necrosis factor-induced release of endogenous fatty acids analyzed by a highly sensitive high-performance liquid chromatography method.
AuthorsBrekke OL, Sagen E, Bjerve KS
JournalJ Lipid Res
PubMed ID9323601
A highly sensitive method to determine agonist-induced release of endogenous fatty acids from cells in culture was developed using high-performance liquid chromatography and fluorescence detection. Fatty acids were selectively derivatized with 1-pyrenyldiazomethane and separated on a LC18 reversed phase column using an acetonitrile-water gradient. The detection limit was approx. 20 ... More
Analysis of membrane phospholipid peroxidation by isocratic high-performance liquid chromatography with ultraviolet detection.
AuthorsMawatari S, Murakami K
JournalAnal Biochem
PubMed ID9784195
A new high-performance liquid chromatography (HPLC) for separation of phospholipid classes with ultraviolet (UV) detection at 210 nm was applied to study of peroxidation of the human erythrocyte membranes induced by soybean lipoxygenase. Phospholipid hydroperoxide production of each phospholipid was monitored at the same time by UV at 234 nm. ... More
Phycotoxins in seafood--toxicological and chromatographic aspects.
AuthorsLuckas B
JournalJ Chromatogr
PubMed ID1494019
Two typical clinical types of algae-related seafood poisoning have attracted medical and scientific attention: paralytic shellfish poisoning (PSP) and diarrhetic shellfish poisoning (DSP). Therefore, it became necessary to establish methods for the evaluation of possible hazards caused by contamination of seafood with these phycotoxins. Bioassays with mice or rats are ... More
Existence of acyl-CoA hydrolase-mediated pathway supplying arachidonic acid for prostaglandin synthesis in microsomes from rabbit kidney medulla.
AuthorsSakuma S, Fujimoto Y, Sawada T, Saeki K, Akimoto M, Fujita T
JournalProstaglandins Other Lipid Mediat
PubMed ID10410378
We have previously shown that acyl-coenzyme A (CoA) hydrolase that hydrolyzes arachidonoyl-CoA (AA-CoA) to arachidonic acid (AA) and CoA is present in the cytosol of rabbit kidney medulla and that this enzyme can supply AA for prostaglandin (PG) synthesis in this region. In the present study, the existence of the ... More
Detection of okadaic acid esters in the hexane extracts of Spanish mussels.
AuthorsFernández ML, Míguez A, Cacho E, Martínez A
JournalToxicon
PubMed ID8730931
Two types of low polar derivatives of OA and dinophysitoxins have been reported in shellfish or in phytoplankton: 7-0-acyl esters containing a fatty acyl group attached through the 7-OH group and diol esters in which the carboxylic group of the toxins has been esterified. These compounds cannot be directly detected ... More
Purification and properties of a phospholipase A2/lipase preferring phosphatidic acid, bis(monoacylglycerol) phosphate, and monoacylglycerol from rat testis.
AuthorsIto M, Tchoua U, Okamoto M, Tojo H
JournalJ Biol Chem
PubMed ID12223468
Phospholipase A(2) (PLA(2)) was purified to homogeneity from the supernatant fraction of rat testis homogenate. The purified 63-kDa enzyme did not require Ca(2+) ions for activity and exhibited both phosphatidic acid-preferring PLA(2) and monoacylglycerol lipase activities with a modest specificity toward unsaturated acyl chains. Anionic detergents enhanced these activities. Serine-modifying ... More
Column-switching high-performance liquid chromatographic method for the determination of SK&F 106203 in human plasma after fluorescence derivatization with 9-anthryldiazomethane.
A sensitive and selective high-performance liquid chromatographic method was developed for the determination of SK&F 106203 3-(2-carboxyethylthio)-3-[2-(8-phenyloctyl)phenyl]propanoic acid, a potent peptidoleukotriene end organ receptor antagonist, in human plasma. The method involves isolation of SK&F 106203 and the internal standard (SK&F 104736) from plasma samples by liquid-liquid extraction prior to derivatization ... More
Potent modification of low density lipoprotein by group X secretory phospholipase A2 is linked to macrophage foam cell formation.
AuthorsHanasaki K, Yamada K, Yamamoto S, Ishimoto Y, Saiga A, Ono T, Ikeda M, Notoya M, Kamitani S, Arita H
JournalJ Biol Chem
PubMed ID12021277
The deposition of cholesterol ester within foam cells of the artery wall is fundamental to the pathogenesis of atherosclerosis. Modifications of low density lipoprotein (LDL), such as oxidation, are prerequisite events for the formation of foam cells. We demonstrate here that group X secretory phospholipase A2 (sPLA2-X) may be involved ... More
Determination of S-carboxymethyl-L-cysteine and some of its metabolites in urine and serum by high-performance liquid chromatography using fluorescent pre-column labelling.
AuthorsStaffeldt B, Brockmöller J, Roots I
JournalJ Chromatogr
PubMed ID1810942
Pre-column labelling techniques are described for the determination of S-carboxymethyl-L-cysteine (CMC) and its metabolites in urine and plasma samples by high-performance liquid chromatography (HPLC) without prior extraction. All substances containing an amino group were converted into fluorescent fluorenylmethyl derivatives with 9-fluorenylmethyloxycarbonyl chloride (FMOC). Deaminated or N-acetylated carbocysteine metabolites were coupled ... More
Catalytic properties of rice alpha-oxygenase. A comparison with mammalian prostaglandin H synthases.
AuthorsKoeduka T, Matsui K, Akakabe Y, Kajiwara T
JournalJ Biol Chem
PubMed ID11909851
Long-chain fatty acids can be metabolized to C(n)(-1) aldehydes by alpha-oxidation in plants. The reaction mechanism of the enzyme has not been elucidated. In this study, a complete nucleotide sequence of fatty acid alpha-oxygenase gene in rice plants (Oryza sativa) was isolated. The deduced amino acid sequence showed some similarity ... More
Effect of docosahexaenoic acid on the generation of platelet-activating factor by eosinophilic leukemia cells, Eol-1.
AuthorsShikano M, Masuzawa Y, Yazawa K
JournalJ Immunol
PubMed ID8468486
Human eosinophilic leukemia (Eol-1) cells were examined for their ability to generate platelet-activating factor (1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine) (PAF) and the effect of supplementation of docosa-hexaenoic acid (C22:6n-3) (DHA) on the PAF synthesis was explored in relation to the fatty acid composition of phospholipids and the liberation of arachidonic acid (C20:4n-6 AA). Although ... More
Hepoxilin A3 formation in the rat pineal gland selectively utilizes (12S)-hydroperoxyeicosatetraenoic acid (HPETE), but not (12R)-HPETE.
AuthorsReynaud D, Demin P, Pace-Asciak CR
JournalJ Biol Chem
PubMed ID7929046
Hepoxilins A3 and B3 have previously been shown to be formed from 12-hydroperoxyeicosatetraenoic acid (12-HPETE) through a heat-insensitive ferriheme catalysis as indicated by experiments with hemin or hemoglobin, typical of nonenzymatic rearrangement (Pace-Asciak, C. R. (1984) Biochim. Biophys. Acta 793, 485-488; Pace-Asciak, C. R. (1984) J. Biol. Chem. 259, 8332-8337). ... More
Purified group X secretory phospholipase A(2) induced prominent release of arachidonic acid from human myeloid leukemia cells.
AuthorsHanasaki K, Ono T, Saiga A, Morioka Y, Ikeda M, Kawamoto K, Higashino K, Nakano K, Yamada K, Ishizaki J, Arita H
JournalJ Biol Chem
PubMed ID10567392
Group X secretory phospholipase A(2) (sPLA(2)-X) possesses several structural features characteristic of both group IB and IIA sPLA(2)s (sPLA(2)-IB and -IIA) and is postulated to be involved in inflammatory responses owing to its restricted expression in the spleen and thymus. Here, we report the purification of human recombinant COOH-terminal His-tagged ... More
Metabolism of fatty acids and their incorporation into phospholipids of the mitochondria and endoplasmic reticulum in isolated hepatocytes determined by isolation of fluorescence derivatives.
AuthorsJakobsson A, Ericsson J, Dallner G
JournalBiochim Biophys Acta
PubMed ID2223867
Isolated hepatocytes were incubated in the presence of [14C]palmitic, [14C]linoleic or [14C]linolenic acid and the time-courses of incorporation of radioactivity into phosphatidylcholine and phosphatidylethanolamine of microsomes and mitochondria were followed. For this purpose a procedure was developed for HPLC separation of 9-diazomethylanthracene (ADAM) derivatives of fatty acids. When [14C]palmitic acid ... More
Purification and characterization of a catalytic domain of rat intestinal phospholipase B/lipase associated with brush border membranes.
AuthorsTojo H, Ichida T, Okamoto M
JournalJ Biol Chem
PubMed ID9442064
A brush border membrane-associated phospholipase B/lipase was solubilized from the distal two-thirds of rat small intestine by autolysis during storage at -35 degrees C over 1 month, and then the enzyme was purified to homogeneity and characterized enzymatically and structurally. The purified enzyme exhibited broad substrate specificity including esterase, phospholipase ... More
A new family of thromboxane receptor antagonists with secondary thromboxane synthase inhibition.
AuthorsPace-Asciak CR, Reynaud D, Demin P, Aslam R, Sun A
JournalJ Pharmacol Exp Ther
PubMed ID11961065
We report herein a novel class of thromboxane receptor (TP receptor) antagonists modeled on unstable natural lipids that we identified several years ago, the hepoxilins. These antagonists have been rendered chemically and biologically more stable than the natural compounds through structural modification by chemical synthesis. We demonstrate that the analogs ... More
The rat leukocyte-type 12-lipoxygenase exhibits an intrinsic hepoxilin A3 synthase activity.
Hepoxilins are biologically relevant eicosanoids formed via the 12-lipoxygenase pathway of the arachidonic acid cascade. Although these eicosanoids exhibit a myriad of biological activities, their biosynthetic mechanism has not been investigated in detail. We examined the arachidonic acid metabolism of RINm5F rat insulinoma cells and found that they constitutively express ... More