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Volume 38, Issue 11
Displaying 1-50 of 63 articles from this issue
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Yasuko KOMATA, Akiko KANAKO, Tadao FUJIE1990 Volume 38 Issue 11 Pages 2907-2910
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe formation of a complex between cycotiamine (CCT), an S-acylated type of thiamine derivative, and a fatty acid (FA) in chloroform has been studied using the solubility method, 1H nuclear magnetic resonance spectroscopy (NMR), and 13C-NMR for the purpose of revealing the moieties of CCT needed for an interaction with FA. The apparent stability constants for an equimolar complex between CCT and myristic acid and for CCT and stearic acid were determined (22.9 and 21.7M-1, at 298K respectively). A similarity of the pattern of interaction in chloroform to that in 1, 2-dichloroethane has been suggested. In the presence of FA, 13C resonance of the carbons adjacent to N-1 in the pyrimidine of CCT were largely shifted upfield. In the presence of FA, the amino proton signal in the pyrimidine of CCT was largely shifted downfield. These results show the necessity of the N-1 nitrogen and the amino group in the pryimidine of CCT for the interaction. In the presence of CCT, the carboxyl carbon resonance of FA shifted upfield.This can be understood to result from the destruction of a dimer of FA by the formation of the complex with CCT.View full abstractDownload PDF (709K) -
Jyoji KURITA, Takeharu YONEDA, Naoki KAKUSAWA, Takashi TSUCHIYA1990 Volume 38 Issue 11 Pages 2911-2918
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermolysis of the 6-aza-3-oxatricyclo[3.2.0.02, 4]heptan-7-ones(8 and 21) and 3, 6-diazatricyclo[3.2.0.02, 4]heptan-7-ones (9 and 22), prepared from the corresponding 2-pyridones (5) via the 2-azabicyclo[2.2.0]hex-5-en-3-ones (7 and 18), resulted in valence isomerization with ring opening to give the novel 1, 4-oxazepin-5-ones (10a-e and 15a-c) and 1, 4-diazepin-5-ones (11a-e and 16a-c), respectively. Treatment of the N-unsubstituted compounds 15 and 16 with triethyloxonium tetrafluoroborate afforded the fully unsaturated 1, 4-oxazepines (23a-c) and 1H-1, 4-diazepines (24a-c), respectively.View full abstractDownload PDF (1252K) -
Haruki SASHIDA, Mamoru KANAME, Takashi TSUCHIYA1990 Volume 38 Issue 11 Pages 2919-2925
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stable N-unsubstituted 1H-1, 4-benzodiazepines (12a-l) having a carbonyl group or its analogue at the 2- or 9-position were prepared from the 4-azidoquinolines (13a-l) by photoreaction in the presence of sodium methoxide.It is known that N-unsubstituetd 1H-1, 4-benzodiazepines having no carbonyl group are too unstable to be isolated.Based on the spectral data, the benzodiazepines (12) isolated are assumed to be stabilized by intramolecular hydrogen bonding between the 1-NH hydrogen and the 2- or 9-carbonyl oxygen, thus allowing their isolation.View full abstractDownload PDF (1051K) -
Masafumi YAMAGISHI, Ken-ichi OZAKI, Hiroshi OHMIZU, Yoshihisa YAMADA, ...1990 Volume 38 Issue 11 Pages 2926-2928
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 1-methylcarbamoylisation (4) with urea in the presence of 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 4-hydroxy-3-methyl-4-ureidocarbonyl-1, 2, 3, 4-tetrahydroquinazolin-2-one (5), which was easily cyclized with 10% HCl to afford a spirohydantoin derivative; 3-methyl-spiro[1, 2, 3, 4-tetrahydroquinazoline-4, 4'-imidazolidine]-2, 2', 5'-trione (6). In a similar manner, 2'-imino-3-methyl-spiro[1, 2, 3, 4-tetrahydroquinazoline-4.4'-imidazolidine]-2, 5'-dione (8) was prepared by the reaction of 4 with guanidine, and 8 was further converted to the spirohydantoin compound 6 by treatment with sodium nitrite in acetic acid.View full abstractDownload PDF (572K) -
Kunizo ARAI, Yuzuru YAMAMOTO1990 Volume 38 Issue 11 Pages 2929-2932
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe biosynthesis of asterriquinones in Aspergillus terreus var. africanus IFO 8835 has been elucidated. Enzymatic activities for the formation of demethyl asterriquinone-D (asterriquinone synthase), prenyltransferase and methyltransferase on asterriquinone were detected in a crude extract of mycelium. Demethyl asterriquinone is biosynthesized from indolepyruvic acid and then methylation of the hydroxyl of group of the quinone moiety occurs.Prenylation proceeds simultaneously at the C-7, C-2 and N-1 positions of the indole moiety.View full abstractDownload PDF (646K) -
Hirotaka SHIBUYA, Keiko KAWASHIMA, Masahiro SAKAGAMI, Hiroyuki KAWANIS ...1990 Volume 38 Issue 11 Pages 2933-2938
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo glycosphingolipids named soya-cerebrosides I and II were isolated from soybean, the seeds of Glycine max MERRILL (Leguminosae), and their chemical structures have been elucidated on the basis of physicochemical evidence and several chemical degradation reactions. By using a newly constructed liquid membrane-type apparatus (W-08) for measurement of ion-transport and ion-binding activities and by employing a method using human erythrocyte membranes for measurement of ion-permeability, it has been found that soya-cerebroside II exhibits ionophoretic activity for Ca2+ion.View full abstractDownload PDF (977K) -
Masami KAWASE, Achintya K. SINHABABU, Ronald T. BORCHARDT1990 Volume 38 Issue 11 Pages 2939-2946
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnalogs of 5, 7-dihydroxytryptamine (5, 7-DHT), namely, 4-fluoro-, 6-fluoro-, and 4, 6-difluoro-5, 7-DHT's (30a-c) were synthesized starting from 4-fluorophenol (7a), 4-fluorobenzyl alcohol (12) and 2, 4-difluorophenol (7b), erspectively.Regiospecific hydroxylation and formylation ortho to fluoro groups, both via aryllithium intermediates, were made possible by the blocking effect of tert-butyldimethylsilyloxy functions and allowed the conversion of the starting materials to the key intermediates, namely, 3, 5-bis(tert-butyldimethylsilyloxy)-2-fluoro-, 4-fluoro- and 2, 4-difluorobenzaldehydes (11a, b and 19, respectively). The latter were converted in one step to the corresponding benzyloxybenzaldehydes, from which indole-2-carboxylates 22a-c were synthesized via azidostyrenes 21a-c, respectively. Decarbonylation of the indole-2-carboxaldehydes(24a-c) produced from 22a-c in two steps gave 2, 3-unsubstituted indoles 25a-c, respectively.Introduction of the aminoethyl side chains on C-3 of 25a-c via the corresponding indole-3-acetonitriles, and subsequent debenzylation generated the hydroxytryptamines, which were isolated as their creatinine sulfate salts 30a-c, respectively.Cyclic voltammetric studies indicated that like 5, 7-DHT, 30a-c undergo electrochemical oxidation in 1M H2SO4 via the corresponding P-quinoneimine derivatives 31a-c by an electrochemical-chemical-electrochemical (ECE) process. The voltammetrically detectable products of the ECE process appear to be the corresponding 5-hydroxytryptamine-4, 7-dione (6) derivatives 33a-c. The nature of the interaction of dissolved O2 with 30a-c at pH 7.4 appears to be strikingly different from that of 5, 7-DHT, which undergoes autoxidation at pH 7.4 via the 4-hydroperoxy derivative 4 to the quinone 6. Thus, contrary to expectation and as judged by ultraviolet-visible spectroscopy, 30a undergoes autoxidation via the p-quinoneimine 31a to give the quinone 6 with loss of fluorine ion while 30b gives an unidentified colorless product(s) and 30c does not react with oxygen at pH 7.4.View full abstractDownload PDF (1270K) -
Kenji TAKENUKI, Hiroko ITOH, Akira MATSUDA, Tohru UEDA1990 Volume 38 Issue 11 Pages 2947-2952
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe β-face of a 2'-ketonucleoside is sterically more hindered than the α-face because of the bulky nucleobase on the β-side at the 1'-position. However, on the reaction of 4-ethoxy-1-[3, 5-O-(1, 1, 3, 3-tetraisopropyl-1, 3-disiloxanediyl)-β-D-erythro-2-pentofuranos-2-ulos-1-yl]-2(1H)-pyrimidinone (6d) with methylmagnesium bromide, the β-methyl addition product (8d) was obtained in a considerable amount. It was found that Lewis basicity of the 2-carbonyl oxygen in the pyrimidine moiety, which is influenced inductively by the substituent at the 5-position, governs the stereoselectivity of the methyl addition reaction.View full abstractDownload PDF (976K) -
Masataka SUGIYAMA, Masao KIKUCHI1990 Volume 38 Issue 11 Pages 2953-2955
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new phenylpropanoid glycosides, named osmanthuside B6 (I), osmanthuside D (II) and osmanthuside E (III), were isolated from the leaves of Osmanthus asiaticus NAKAI (Oleaceae). The structures of I, II and III were determined to be β-(p-hydroxyphenyl) ethyl O-α-L-rhamnopyranosyl-(1→3)-6-O-trans-p-coumaroyl-β-D-glucopyranoside, β-(p-hydroxyphenyl) ethyl O-α-L-rhamnopyranosyl-(1→3)-4-O-cis-p-coumaroyl-β-D-glucopyranoside and β-(p-hydroxyphenyl) ethyl 6-O-trans-feruloyl-β-D-glucopyranoside, respectively, on the basis of chemical and spectral data.View full abstractDownload PDF (556K) -
Kazunobu HARANO, Shigeru YAMASHIRO, Keisuke MISAKA, Takuzo HISANO1990 Volume 38 Issue 11 Pages 2956-2959
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyrolytic conversion of S-(2-alkenyl) S-alkyl dithiocarbonates (allylic dithiolcarbonates) to 2-alkenyl alkyl sulfides (allylic sulfides) was catalyzed by phenols bearing electron-attracting substituents. The reaction is pseudo-first-order and the apparent first-order rate constants are proportional not only to the concentration of phenols but also to the hydrogen-bonding capability of phenols. The entropy of activation for the phenol-catalyzed reaction is ca. 8 e.u. smaller than that for the uncatalyzed reaction. The reactivity of S-(1-phenylallyl) S-alkyl dithiocarbonates did not obey Hammett's or Taft's equation. Based on these findings together with the MNDO (modified neglect of diatomic overlap) calculation data, a possible role of phenols in the pyrolytic conversion of allylic dithiolcarbonates to allylic sulfides is discussed.View full abstractDownload PDF (663K) -
Motomasa KOBAYASHI, Jun-ichi TANAKA, Taketo KATORI, Isao KITAGAWA1990 Volume 38 Issue 11 Pages 2960-2966
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFollowing the characterization of swinholide A (1), the major cytotoxic dimeric macrolide, three new congeneric dimeric macrolides, named swinholide B (2), swinholide C (3), and isoswinholide A (10), have been isolated from the Okinawa marine sponge Theonella swinhoei. The structures of these dimeric macrolides have been elucidated on the basis of chemical and physiocochemical evidence. These dimeric macrolides were shown to exhiit potent cytotoxicities toward KB cell lines.View full abstractDownload PDF (989K) -
Jun-ichi TANAKA, Tatsuo HIGA, Motomasa KOBAYASHI, Isao KITAGAWA1990 Volume 38 Issue 11 Pages 2967-2970
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe absolute stereostructure of a potent cytotoxic dimeric macrolide misakinolide A (5)(=bistheonellide A), which was isolated from an Okinawan marine sponge of Theonella sp., was determined by chemical correlation with swinholide A (1). The stereochemistry of misakinolide A was shown to be identical with tha of another cytotoxic dimeric macrolide, swinholide A (1), which was isolated from the Okinawan marine sponge Theonella swinhoei and the stereostructure of which was recently determined.View full abstractDownload PDF (527K) -
Taisuke ITAYA, Tsunehiro HARADA1990 Volume 38 Issue 11 Pages 2971-2976
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDehydration of 5-(cyanomethylamino)-1-methyl-1H-imidazole-4-carboxamide (14a) with a combination of phosphorus oxychloride and triethylamine afforded the nitrile 17a. This compound underwent selective hydration at the cyanamide moiety to furnish the urea 18a followed by cyclization to 3, 9-dimethylisaguaninae (19a) under alkaline conditions. Similar dehydration of the nucleoside analog 14b followed by treatment with 0.1 N aqueous sodium hydroxide led to the first access to 3-methylisoguanosine (19c). Although 3-methylisoguanosine (19c) proved to undergo hydrolysis at the N-glycosidic bond most slowly among the known 3-methyl-9-β-D-ribofuranosylpurines in 0.1 N hydrochloric acid at 25°C, the rate was 650 times faster than that for the unmethylated isoguanosine (3).View full abstractDownload PDF (964K) -
Atsushi NISHIDA, Tatsuo HAMADA, Osamu YONEMITSU1990 Volume 38 Issue 11 Pages 2977-2980
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTosyl esters were hydrolyzed by irradiation with ultraviolet light (>330nm) under photo-sensitized conditions. 1.5-Dimethoxynaphthalene and (4, 8-dimethoxynaphthyl)propionic acid were effective for the transformation in aqueous acetonitrile in the presence of hydrazine. The reaction was successfully applied to the hydrolysis of tosylates of sugars and nucleosides.View full abstractDownload PDF (627K) -
Satomi SAKANOUE, Shinya HARASAWA, Naoki YAMAZAKI, Ryuji YONEDA, Takush ...1990 Volume 38 Issue 11 Pages 2981-2985
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyrolysis of O-2-(1-benzyl-2-pyrrolidinyl and 2-piperidyl)ethyl O-phenyl thionocarbonates (4 and 25) in acetonitrile gave 1-benzyl-4-phenoxyhexahydro-1H-azepine (7) and 1-benzyl-4-phenoxyoctahydroazocine (26) with liberation of COS in 55% and 32% yields, accompanied with 2-(2-phenoxyethyl)pyrrolidine and piperidine (8 and 27), via the azetidinum intermediate (6). On the other hand, O-phenyl O-2-(2-tetrahydrothienyl)ethyl thionocarbonate (32) resulted in the predominant formation of the O, S-rearrangement product (35) in 53% yield.View full abstractDownload PDF (884K) -
Masateru ONO, Masatoshi NISHI, Toshio KAWASAKI, Kazumoto MIYAHARA1990 Volume 38 Issue 11 Pages 2986-2991
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight ether-soluble resin glycosides (jalapins), operculins I-VIII, were isolated from Phizoma Jalapae Braziliensis (the roots of Ipomoea operculata). Among them, the structures of operculins I, II, V, VII and VIII, which have a common glycosidic acid, operculinic acid A, have been determined on the basis of chemical and spectral data. Similar to the jalapins so far isolated from several Convolvulaceae plants, all of them have intramolecular macrocyclic ester structures. They have n-dodecanoic and/or n-decanoic acid as a component organic acid in place of hitherto known isobutyric, 2-methylbutyric, tiglic and nilic acids.View full abstractDownload PDF (784K) -
Hiroyuki SAWANISHI, Shuichi SAITO, Takashi TSUCHIYA1990 Volume 38 Issue 11 Pages 2992-2996
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolysis of the 3-methoxy-4-azidopyridazines (11) in the presence of a base such as methoxide ion and diethylamine resulted in ring-expansion to produce the 1H-1, 2, 5-triazepines (12 and 27), which were too unstable to be isolated, but tautomerized to the stable 4H-isomers (13 and 28) on further treatment with sodium methoxide and were converted to the stable 1-acetyl-1H-1, 2, 5-triazepines (14 and 29) by acetylation with acetyl chloride. The products 12-14 and 27-29 are the first examples of fully unsaturated 1, 2, 5-triazepines and were characterized by means of spectral analyses and some chemical reactions.View full abstractDownload PDF (886K) -
AKira IIDA, Shinya YOSHIMATSU, Masaki SANEKATA, Tetsuro FUJITA1990 Volume 38 Issue 11 Pages 2997-3003
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe antibiotic icosapeptide trichosporin B-V, which was isolated from Trichoderma polysporum, was synthesized by assembling five peptide fragments via the N, N7'-dicyclohexylcarbodimide method. The synthesized peptide was identical with the natural one.View full abstractDownload PDF (1013K) -
Ta-chen LIN, Gen-ichiro NONAKA, Itsuo NISHIOKA, Feng-chi HO1990 Volume 38 Issue 11 Pages 3004-3008
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA chemical examination of mylobalans (the fruits of Terminalia chebula RETZ., Combretaceae) has led to the isolation and characterization of punicalagin (1), terflavin A (2) and a new ellagitannin named terchebulin (3), which possesses a anovel tetraphynylcarboxylic acid (terchebulic acid) moiety. Furthermore, from the leaves of T. chebula, a series of biogenetically related hydrolyzable tannins, terflavins B (7), C (9) and D (10), punicalagin (1) and punicalin (8), have been isolated and structurally elucidated. The concomitant isolation of terflavins A (2) and B (7) provides biogenetic evidence that the tervhebulic acid moiety is derived by an oxidative carbon-oxygen coupling of adjacent flavogallonic acid and gallic acid esters.View full abstractDownload PDF (726K) -
Catherine RUBAT, Pascal COUDERT, Bernard REFOUVELET, Pierre TRONCHE, P ...1990 Volume 38 Issue 11 Pages 3009-3013
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 3-oxo-5-substituted-benzylidene-6-methyl-(4H)-2-pyridazinylacetamides and 2-pyridazynylacetylhydrazides were synthesized and evaluated for anticonvulsant activity against electrically and chemically induced seizures.In the maximal electroshock-induced seizures test, most of the derivatives showed an anticonvulsant effect better than that of sodium valproate, a commonly used anticonvulsant drug.At 100 mg/kg orally, compounds 5a and 5b respectively protected 50 and 60% of the mice against pentylentetrazole-induced seizures. In addition, these two derivatives showed significant anticonvulsant properties at doses that did not produce ataxia or sedation. The title compounds were also tested for their ability to antagonize convulsions induced by bicuculline and strychnine. Their effect on tremors induced by oxotremorine in mice was also evaluated.View full abstractDownload PDF (810K) -
Yuji NOMOTO, Haruki TAKAI, Tadashi HIRATA, Masayuki TERANISHI, Tetsuji ...1990 Volume 38 Issue 11 Pages 3014-3019
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of novel 1-(6, 7-dimethoxy-4-quinazolinyl)piperidines carrying substituted hydantoin and 2-thiohydantoin rings was synthesized and examined for cardiotonic activity in anesthetized dogs. Introduction of isopropyl and sec-butyl group at the 5-position of the hydantoin and thiohydantoin rings led to potent inotropic activity. Effects of insertion of an alkyl chain between the piperidine and the hydantoin rings were also examined. The structural requirements necessary for optimal cardiotonic activity within the series were investigated.View full abstractDownload PDF (753K) -
Itaru YAMAMOTO, Norio MUTO, Kouki MURAKAMI, Sadaharu SUGA, Hisao YAMAG ...1990 Volume 38 Issue 11 Pages 3020-3023
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe definite structure and chemical stability of a new glucoside of L-ascorbic acid (AA) which was enzymatically glucosylated with rat intestinal and rice seed α-glucosidases were reported. The stability of this AA derivative in water under aerobic conditions was proved by its remarkable resistance against enhanced oxidative degradation by heat, Cu2+ ion or ascorbate oxidase, and it was found to have no reducing activity toward radicals. These properties were obviously distinguishable from those of AA. This glucoside was effectively hydrolyzed by α-glucosidases which possessed the ability to synthesize itself, resulting in the liberation of AA activity. The conjugate was composed of equimoles of AA and glucose. Nuclear magnetic resonance spectra, mass spectra, pH profiles of ultraviolet spectra and pKa value of 3.10 supported the coupling of α-glucose to the 2-position of AA.From these results, its structure was assigned 2-O-α-D-glucopyranosyl-L-ascorbic acid, being distinct from 6-O-α-D-glucopyranosyl-L-ascorbic acid formed with Aspergillus niger α-glucosidase. These findings indicate that the 2-O-glucoside formed by regioselective transglucosylation withstands oxidateive degradation even in aqueous solutions and it can be used as an available active AA source for multicomponent liquid products.View full abstractDownload PDF (744K) -
Yuji ISHIHARA, Yoshihiro KIYOTA, Giichi GOTO1990 Volume 38 Issue 11 Pages 3024-3030
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA variety of isoindolo[2, 1-a]quinoline derivatives as well as the following related heterocycles have been prepared : 11b, 12-dihydro-5H-isoindolo[2, 1-b][2]benzazepine-7, 13-dione (8a), 7, 8, 14, 14a-tetrahydroisoindolo[2, 1-c][3]benzazocine, -5, 13-dione(8b), 6a, 7-dihydroisoquinolino[2, 3-a]quinoline-5, 12-dione(12), 2, 3, 3a, 4-tetrahydropyrrolo[1, 2-a]quinoline-1, 5-dione (14), and pyrido[2', 3' : 3, 4]pyrrolo[1, 2-a]quinoline-5, 11(5H)-dione(17). The key synthetic step involves an intramolecular Friedel-Crafts reaction of acid chlorides such as isoindole-1-acetyl chlorides (4), the acids (3) of which were prepared starting with 2-arylisoindole-1, 3(2H)-diones (2-arylphthalimides)(1). The protective effects of isoindolo[2, 1-a]quinoline derivatives (19 and 20) against N2-induced hypoxia were examined. Among them, 6-(diethylaminomethyl)isoindolo[2, 1-a]quinoline-5, 11(5H)-dione (19b) showed the most potency.View full abstractDownload PDF (1041K) -
Toshinari OH-HARA, Yutaka KAWAZOE, Hiroshi SAKAGAMI1990 Volume 38 Issue 11 Pages 3031-3034
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDiverse biological activities of hot-water and alkali extracts of lignified materials were reviewed and the molecular species involved are discussed. Materials tested included pine cone of Pinus parviflora SIEB. et ZUCC., wood chips of slash pine, Douglas fir, and tallow wood, and two basidiocarps, in addition to their partially degraded preparations and commercial lingnins. As a tentative conclusion, the lignin structure of these extracts mights be responsible for the potent stimulation of granulocytic cell iodination, inhibition of viral infection and/or proliferation in vitro, and inactivation of viral ribonucleic acid (RNA)-dependent RNA polymerase and (adenosine diphosphate-ribose)n glycohydrolase. Other activities displayed by some of these extracts, such as antibacterial and antitumor activities, induction of hemolytic plaque-forming-cells in mice, and stimulation of deoxyribonucleic acid synthesis of isolated splenocytes, remain to be investigated.View full abstractDownload PDF (696K) -
Ikuo UEDA, Katsuyuki ISHII, Katsuo SHINOZAKI, Masao SEIKI, Heihachiro ...1990 Volume 38 Issue 11 Pages 3035-3041
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Phenoxypropylacetamide derivatives were prepared and tested for antiulcer activity. These compounds exhibited both gastric acid antisecretory and cytoprotective properties. Structure-activity studies led to the identification of N-[3-{-(1-piperidinylmethyl)phenoxy}propyl]-2-(2-hydroxyethylthio)acetamide (8), which was selected for further development and clinical evaluation.View full abstractDownload PDF (1000K) -
Hiromu HARADA, Kinji IIZUKA, Tetsuhide KAMIJO, Kenji AKAHANE, Ryoji YA ...1990 Volume 38 Issue 11 Pages 3042-3047
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe experimental details for the synthesis of human renin inhibitors are described. In order to aviod metabolic degradation of the Phe-His (P3-P2) amide bond in transition-state analogs, structurally modified acyl residues (P4-P3) were incorporated into the inhibitors. Compound 1a, which contained 2-(1-naphthylmethyl)-3-(N-phenethylcarbamoyl)propionyl residue (P4-P3) with a retro-inverso amide bond, L-histidine, and norstatine isoamylamide residue (P1-P1') as a transition-state mimic, had potent human renin inhibitory activity, and it lowered blood pressure when administered orally to common marmosets.View full abstractDownload PDF (879K) -
Masatoshi YANATO, Yasuo TAKEUCHI, Ming-rong CHANG, Kuniko HASHIGAKI, T ...1990 Volume 38 Issue 11 Pages 3048-3052
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSome tetracyclic quinolines (9 and 14) with a [2-methoxy-4-[(methylsulfonyl)amino]phenyl]amino side chain were prepared and their deoxyribonucleic acid (DNA) intercalative properties, KB cytotoxicity, antitumor activity (P388 leukemia), and ability to induce topoisomerase II dependent DNA cleavage were investigated. The indoloquinoline derivative 9 exhibited the most potent activity (dose=6.3mg, T/C%=300) in this series. The steric structural features of the chromophores of the compounds previously and newly synthesized were studied by a computer-associated molecular graphics technique. Relationships between the steric structural features of the chromophores and biological activities are also discussed.View full abstractDownload PDF (763K) -
Johji YAMAHARA, Yu Hao LI, Yoshin TAMAI1990 Volume 38 Issue 11 Pages 3053-3054
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of bitter cardamon (the fruit of Alpinia oxphylla), used as a medicine and a condiment, on HCl/ethanol-induced gastric lesions in rats were examined. The acetone extract at 50mg/kg, P.o. significantly inhibited gastric lesions by 57.0%. An analysis of the active constituents in the acetone extract was performed using column chromatography. Nootkatone at 20mg/kg, p.o. significantly inhibited gastric lesion. These results suggest that nootkatone, the sequiterpenoid is an important constituent in stomach medications containing bitter cardamon.View full abstractDownload PDF (404K) -
Yoshihiro MIMAKI, Yutaka SASHIDA1990 Volume 38 Issue 11 Pages 3055-3059
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe fresh bulbs of Lilium brownii var. colchesteri were found to contain five steroidal saponins : 26-O-β-D-glucopyranosylnuatigenin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (6), 26-O-β-D-glucopyranosylnuatigenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (7), brownioside (8), deacylbrownioside (9) and 27-O-(3-hydroxy-3-methylglutaroyl)isonarthogenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-glicopyranosyl-(1→4)]-β-D-glucopyranoside (10); and two steroidal alkaloids : β1-solamargine (11) and solasodine 3-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (12); along with several phenolic constituents. Compounds 7, 10 and 12 are new naturally-occurring compounds.View full abstractDownload PDF (849K) -
Isao KOUNO, Kaori MORI, Shoko OKAMOTO, Sadao SATO1990 Volume 38 Issue 11 Pages 3060-3063
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new sesquiterpene lactones, named anislactone A and B, were isolated from the pericarps of Illicium anisatum.The structure of anislactone A was established by X-ray crystallographic analysis. Anislactone B was the isomer of anislactone A, and its structure was determined by spectral data compared with those of anislactone A. They were considered to be the biological derivatives from anisatin of its derivative.View full abstractDownload PDF (657K) -
Hideaki TANIMORI, Takako MAEDA, Akira AKAHORI, Shinsuke SONOI, Seizo K ...1990 Volume 38 Issue 11 Pages 3064-3068
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA newly selected antibody enzyme immunoassay (SAEIA) for aqueous hoelen extract was developed. Hoelen fragments were immunized and an antiserum specific for hoelen was elicited in rabbits. An aqueous extract of hoelen was converted to a solid-phase antigen using microtiter plates. The efficiency for immobilization of hoelen extract to three types of microtiter plates was compared and carbo-plate was chosen as the solid-phase antigen support. A new assay method for a hoelen extract, with a working range between 3 ng and 30 μg, was developed applying the novel assay principle of SAEIA. The selective binding of the antibodies specific for hoelen extract, contained in the anti-hoelen serum, to the solid-phase antigen, was detected using β-D-galactosidase labeled anti-rabbit immunoglobulin G as a tracer. Specificity of the SAEIA to the hoelen extract was also demonstrated. The contents of hoelen extract in three Chinese traditional medicines were successfully analyzed applying the SAEIA method.View full abstractDownload PDF (768K) -
Noriko SHIMIZU, Masashi TOMODA, Mieko KANARI, Ryoko GONDA, Akemi SATOH ...1990 Volume 38 Issue 11 Pages 3069-3071
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA neutral polysaccharide, named glycyrrhizan UC, was isolated from the root of Glycyrrhiza uralensis FISCHER.It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 69000.Glycyrrhizan UC is composed of L-arabinose : D-galactose : D-glucose : L-rhamnose in the molar ratio of 10 : 30 27 : 1.Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies indicated its structural feature as an arabino-3, 6-galacto-glucan type polysaccharide.View full abstractDownload PDF (627K) -
Kohfuku KOHDA, Takashi NAKAGAWA, Yutaka KAWAZOE1990 Volume 38 Issue 11 Pages 3072-3075
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of calf thymus deoxyribonucleic acid (DNA) with the horseradish peroxidase-H2O2 system resulted in effecient formation of 8-hydroxydeoxyguanosine (8-OH-dG) residues. It was concluded that singlet oxygen was the reactive species involved, based on experiments using active oxygen scavengers and D2O. For 8-OH-dG formation, a higher-ordered polynucleotide structure seems to be required : double stranded DNA was a better substrate for the reactive species than single stranded DNA, and monomeric deoxyguanosine underwent C8-hydroxylation to a lesser extent.View full abstractDownload PDF (610K) -
Mitsuteru NUMAZAWA, Ayako MUTSUMI, Hiroki KIGAWA1990 Volume 38 Issue 11 Pages 3076-3080
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAndrost-4-ene-3, 6-dione derivatives 2-4 and 3α-methoxy-4-en-6-one steroid 7 were prepared and tested for their ability to inhibit aromatase in human placental microsomes. The 16α-bromide 2, the 16α-alcohol 3, and the 3α-methoxide 7 of this series were effective competitive inhibitors of aromatase with apparent Ki's of 150nM, 1.18 μM, and 70 nM.Compound 2 caused a time-dependent, biphasic loss of aromatase activity in the presence of reduced nicotinamide adenine dinucleotide phosphate (NADPH) while compound 7 caused a time-dependent, pseudo-first order inactivation of the activity, with kinact' of 0.417 and 0.036 min-1 for compounds 2 and 7. NADPH and oxygen were required for the time-dependent inactivation and the substrate, androst-4-ene-3, 17-dione, prevented it in each case.View full abstractDownload PDF (715K) -
Haruki KAZAMA, Noriko TABATA, Kazuko OHGI, Masachika IRIE1990 Volume 38 Issue 11 Pages 3081-3085
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA nuclease (3'-nucleotidase) similar to P1 nuclease from Penicillum citrinum was purified from a commercial digestive from a Penicillum sp. The activity of the nuclease (PA) was separated to three fractions by diethylaminoethyl-Toyopearl 650M column chromatography, in total yield of 10%. The apparent molecular weight of these three nucleases, PA1, PA2 and PA3 was 35000, 33000, and 32000, respectively. All of them were homogeneous so far as checked by sodium dodecyl sulfate slab gel electrophoresis. The three uncleases differed in carbohydrate content, but their aminoacid composition was practically the same, and very similar to that of P1 nucleaes. The molecular weight of nuclease PA3, the major component of nuclease PA, was approximately 27000 after digestion by endoglycosidase F. The N-terminal and C-terminal amino acid sequences of nuclease PA3 were determined by Edman degradation and carboxypeptidase(s) digestion, respectively.The nuclease PA3 was inactivated in the presence of 10 mM ethylenediamine tetraacetic acid (EDTA) and 65% of its native enzyme activity restored by the addition of 20 mM ZnCl2. The pH-dependent photooxidative inactivation of nuclease PA3 was accelerated by removal of Zn ion by EDTA or trishydroxymethyl aminomethane, indicating the possible chelation of Zn2+ with some histidine residues.View full abstractDownload PDF (879K) -
Toshinobu SEKI, Chieko TOEDA, Takeo KAWAGUCHI, Kazuhiko JUNI, Kenji SU ...1990 Volume 38 Issue 11 Pages 3086-3089
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSZidovudine (azidothymidine, AZT), a potent antiviral agent acting on acquired immunodeficiency syndrome virus, was examined with regard to permeation through rat and human skin. A steady state plasma concentration of AZT after transdermal application in rats estimated from both pharmacokinetics data after i.v. administration and penetration rate through excised rat skin from 10% oleic acid (OA) aqueous solution shows penetration about 85 tims higher compared to that from 10% OA would be needed for therapeutic efficacy. A mixed-solvent system consisted of 5% Sefsol-318[○!R] (S-318), 10% OA, 10% N-methyl-2-pyrrolidone (MP), 20% propylene glycol (PG) and water showed promising characteristics as a vehicle in terms of permeability of AZT through excised rat skin. The maximum flux of 0.41 μmol/cm2/h was observed in excised human skin after application of a gel formulation including S-318, OA, MP and PG. The result suggests a possible use of the gel formulation to gain an effective plasma concentration in humans.View full abstractDownload PDF (612K) -
Shiro YOSHIOKA, Yukio OKANO, Yuzo MIZUKAMI, Yoshinori NOZAWA1990 Volume 38 Issue 11 Pages 3090-3093
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSystematic analyses of the interaction between liposomes and cells were examined. Liposomes were found to affect the growth of mouse NIH 3T3 cells depending upon their size, net charge, and cholesterol content. Among the charged compounds, stearylamine was the most inhibitory and showed complete inhibition of cell growth at 100 μM. The cholesteraol-rich and small unilamellar vesicles were more suppressive compared to the cholesterol-poor and multilamellar ones, respectively. The binding assay of liposomes to the cells showed a positive correlation between liposome binding and the extent of growth inhibition. Suppression of liposome uptake by inhibitors of the cytoskeletal system and energy metabolism were suggestive of an endocytotic mechanism for the cellular uptake of liposomes. The growth inhibitory effect seemed secondary to the intracellular uptake of liposomes, and peroxidation of incorporated lipids would lead to cellular damage. Therefore, it is highly recommended that potential growth inhibitory effects associated with the particular composition and other properties of liposomes should be carefully assessed in any human studies, especially for long-term use.View full abstractDownload PDF (759K) -
Tadakazu TOKUMURA, Tomohide TANAKA, Atsushi SASAKI, Yutaka TSUCHIYA, K ...1990 Volume 38 Issue 11 Pages 3094-3098
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stability and some physicochemical properties of a novel hexapeptide, (Me)Arg-Lys-Pro-Trp-tert-Leu-Leu-OEt (I), with neurotensin activity, were investigated. The degradation of I in aqueous solution was observed as a pseudo-first order reaction. By determining the degradation rate of I at various pH values, it was found that I was most stable at around pH 4. The activation energies of the degradation in aqueous solutions at pH 2.2, 6.1, 7.0 and 8.0 were 16.3, 22.2, 23.9 and 24.2kcal/mol, respectively.The enzymatic hydrolysis of I was studied in vitro with a porcine liver esterase at 37°C. The degradation of I in this system was observed as a pseudo-first order reaction. The degradation rate of I in the presence of the esterase was about 10000 times larger than the rate in a buffer solution.I in the solid state was stable under 65°C and labilized by strong light and/or high humidity. The pKa1, pLa2 and pKa3 of I were 7.1, 10.0 and 11.3, respectively. The partition coefficients between n-octanol and the buffer solution at pH values ranging from 2 to 11 were measured. The partition coefficient increased with the increase of the pH value.But the value at pH 7.0 was 2.10×10-2. which was very low. The solubility of I in aqueous solution was more than 10 mg/ml. From the results of the powder X-ray differaction pattern, I in the solid state was found to be amorphous.The dissolution rates in the 1st and 2nd fluid of JPXI at 37°C and 100 rpm were 19.4 and 9.0 mg/cm2·min, respectively.View full abstractDownload PDF (691K) -
Yasushi ARANO, Masashi YABUKI, Tugunari YAHATA, Kazuko HORIUCHI, Akira ...1990 Volume 38 Issue 11 Pages 3099-3101
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSModification of the chelate ring structure of technetium-99m(99mTc) dithiosemicarbazone (DTS) chelate was carried out in pursuit of a more stable and lipophilic compound. A new DTS chelating molecule, pentane-2, 4-dione bis(N-methylthiosemicarbazone) (PETS), with a 5-6-5 membered chelate ring stracture, was synthesized and labeled with 99mTc. PETS generated two 99mTc compounds as major products. Both had much higher stability and lipophilicity than a 5-5-5 membered 99mTc DTS compound, as well as great stability in plasma. Both 99mTc-PETS compounds were rapidly extracted by the brain and heart when injected into mice. Thus, the modified chelate ring structure afforded a preferable characteristics to DTS chelate as for the chelating site for technetium radiopharmaceuticals.View full abstractDownload PDF (607K) -
Toshihisa YOTSUYANAGI, Naoko OHTA, Norihiro TANAKA, Ken IKEDA1990 Volume 38 Issue 11 Pages 3102-3106
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe complex formation between gallium(III) and adriamycin (ADR) was investigated in 0.1 M KNO3 at 25°C.With excess concentration of Ga(III) compared to ADR, Ga(III) was found to be coordinated with ADR in the low pH region below about 4.0. The spectrophotometric titration data supported the hypothesis that one proton is released as a result of complexatin between Ga(III) and ADR via a 1 : 1 stoichiometry, and a phenolix oxygen on the ADR is involved. The stability constant of the complex was obtained by two different spectrophotometric methods. First, the absorbance development and pH changes reflecting the release of a proton due to complexation were monitored and the stability constant was estimated using the method of Hildebrand-Reilley.Secondly, ADR was titrated with increaing Ga(III) at constant pH 3.0 and analyzed by the Benesi-Hildebrand method. We took into consideration gallium hydrolysis in the calculation. The stability constants, 1.24×108 and 3.06×108M-1 obtained by the two different methods, showed good agreement within an order-of-magnitude range.View full abstractDownload PDF (755K) -
Yorinobu YONEZAWA, Itaru SHINOHARA, AKinobu OTSUKA, Hisakazu SUNADA1990 Volume 38 Issue 11 Pages 3107-3111
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLog-normal particle-size-distributed systems were expressed as a generalized equation and the relative diameter which gave the maximum relative weight was expressed as a function of the standard deviation of log-normal particle-size distribution. Generalized distribution curves independent of the mean particle size were then obtained. Several mixed model systems were prepared with sieved N-propyl p-hydroxybenzoate crystalline particles following the generalized distribution curves. The dissolution of model systems were coducted under sink and nonsink conditions, and the dissolution processes were simulated on the basis of cube root law equations. After the validity of the simulation method was confirmed, the method was applied to estimate the apparent mean diameters which partially define the isotropic dissolution processes of log-normal particle-size-disributed systems. The apparent mean diameter was then expressed as a function of the standard deviation of log-normal particle-size distribution.View full abstractDownload PDF (814K) -
Ichimaro YAMADA, Tomoko GODA, Miwako KAWATA, Takako SHIOTUKI, Kenji OG ...1990 Volume 38 Issue 11 Pages 3112-3115
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe relationship between gastric acidity and the bioavailability of two kinds of sustained-release indomethacin (IM) formulations was investigated in gastric acidity-controlled beagle dogs, and compared with that of rapid-release IM formulations.All test dosage forms were more rapidly dissolved in simulated intestinal fluid than in simulated gastric fluid.Gastric acidity did not affect the bioavailability of IM from the rapid-release formulation. However, the bioavailability of IM from the two kinds of sustained-release formulations were markedly influenced by gastric acidity. The rates of IM bioavailability from both of the sustained-release formulations were faster under low acidity conditions than under high acidity conditions (p<0.01). In addition, Tmax and mean residence time (MRT) were approximately the same for the rapid-release and sustained-release formulations under low acidity conditions.These results suggest that the IM sustained-release formulations showed a rapid-release profile under low acidity conditions.View full abstractDownload PDF (658K) -
Katsu NAKAMORI, Ikuo KOYAMA, Tomomi NAKAMURA, Tsuguchika YOSHIDA, Masa ...1990 Volume 38 Issue 11 Pages 3116-3119
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of taurine in protecting biomembrane attacked by hypochlorous acid (HOCl) was examinded using canine erythrocytes which had been pre-treated with HOCl. In the treatment, most of the HOCl was consumed as a result of its reaction with a number of electrophilic substances, such as free amino groups (-NH2) in the membrane, whereas hemoglobin inside the cells was not oxidized. The lysis of HOCl-treated erythrocytes was dependent on the concentration of HOCl and on the incubation time at 37°C. Taurine inhibited the lysis at 37°C in a dose dependent manner. During the incubation of HOCl-treated erythrocytes with taurine, an appreciable amount of monochlorotaurine (TauNHCl) was detected in the supernate. This suggests that taurine might remove the oxidized chlorine from HOCl-treated erythrocytes, resulting in the production of TauNHCl. The effect of taurine on the removal of Cl+ moiety was further examined using Sepharose gel with free amino groups. Taurine removed Cl+ moiety from HOCl-treated Sepharose gel, and the yield of TauNHCl depended on the concentration of taurine and the incubation time. These results indicate that taurine might inhibit the hemolysis by scavenging the oxidized chlorine moiety from the HOCl-treated erythrocytes.Inhibition of the HOCl-induced hemolysis was also observed with other amino acids. The concentrations of taurine, α-alanine, β-alanine and glycine required for 50% inhibition of the lysis were 18, 30, 34, and 40 mM, respectively; thus taurine was the most effective inhibitor of all the amino acids. These results clearly indicate that taurine could be effective in inhibiting the biomembrane damage caused by HOCl.View full abstractDownload PDF (643K) -
Keijiro TERASHITA, Satoru WATANO, Kei MIYANAMI1990 Volume 38 Issue 11 Pages 3120-3123
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA granulation experiment was conducted with a high speed type granulator. Power consumption was measured during the experiment and, in accordance with data, frequency analysis was performed to quantitatively determine the granulation process. The method for frequency analysis was the computation of fluctuatin (standard deviation) of power consumption and FFT (fast Fourier transform) analysis.As a result, the granulation end point was determined and the mechanism was made clear by the use of fluctuation (standard deviation) of power consumption and intensity of spectrum obtained by FFT analysis. With these efforts, establishment of a self-control system of granulation has been made possible.View full abstractDownload PDF (632K) -
Toshihisa YOTSUYANAGI, Isamu YOSHIOKA, Naoki SEGI, Ken IKEDA1990 Volume 38 Issue 11 Pages 3124-3126
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of monovalent metal ions (K+ and Na+) and propranolol (pKa=9.45, a model cationic drug) on the calcium association in calcium-induced alginate gel beads and on the size changes of the beads were investigated. While calcium ions are an essential component for the gelation of alginate, the associated calcium was discharged by coexisting ionic substances such as the species above without the beads being disintegrated in water and buffers at pHs less than 4.0. The following became evident : (1)the accosiated calcium was completely discharged at pH 1.0 resulting in contractin of the bead body to about half, (2) at pH 4.0 about 75% of the calcium was lost and the bead volume was greatly reduced as the drug loading increased, (3) the calcium-discharge action was comparable among the above sucstances, (4) however, the monovalent metal ions brought about expansion of the beads while the drug resulted in contraction of the neads, depending on the bulk concentraion of the drug.View full abstractDownload PDF (597K) -
Shoji KOJIMA, Toshiro INOUE, Morio KIYOZUMI, Hideaki SHIMADA1990 Volume 38 Issue 11 Pages 3127-3129
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe protective effect of N-benzyl-D-glucamine dithiocarbamate (BGD) against gastrointestinal and bone marrow toxicities produced by cis-diamminedichloroplatinum (DDP) injection in rats was studied. Rats were injected i.p. with BGD (2mmol/kg) immediately after i.v. injection of DDP (20μmol/kg). A scanning electron micrograph of the jejunum after DDP treatment showed damage in the villi, and that BGD protected the DDP-induced jejunal damage. BGD treatment also had a protective effect against DDP-induced diarrhea. BGD significantly reversed the reduction in maltase and sucrase activities of jejunal mucosa of rats treated with DDP. Platinum (Pt) concentrations in the gastrointestine as well as in the kidney and liver after DDP injection decreased following BGD treatment. The reduction of leukocytes following DDP injection returned to control values after BGD treatment. Biliary and urinary excretions of Pt after DDP injection was remarkably increased by BGD treatment. The results of this study indicated that the injection of BGD to rats treated with DDP can effectively remove Pt from the body through biliary and urinary excretions, resulting in protection of the gastrointestinal and bone marrow toxicities induced by DDP treatment.View full abstractDownload PDF (1021K) -
Toshiya HONDA, Morio KIYOZUMI, Shoji KOJIMA1990 Volume 38 Issue 11 Pages 3130-3135
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPulmonary toxicity of naphthalene (NAP), 2-methylnaphthalene(2-MN), 2-isopropylnaphthalene (2-IPN) and 2, 6-diisopropylnaphthalene (2, 6-DIPN) was studied in mice. Twenty four h after the intraperitoneal (i.p.) administration of NAP (200mg/kg (1.6mmol)) or 2-MN (400mg/kg (2.8mmol)), pulmonary damage was detected. Prior treatment with diethyl maleate resulted in enhancement of NAP and 2-MN-induced bronchiolar damage. In contrast to the effects of NAP and 2-MN, injections of 2-IPN (3000mg (17.6mmol)/kg) and 2, 6-DIPN (3000mg (14.2mmol)/kg) did not cause detectable pulmonary damage. Injections of NAP and 2-MN caused considerable depletion of pulmonary reduced glutathione (GSH), while injections of 2-IPN and 2, 6-DIPN caused only a slight depletion. There were general decreases in the binding of the compounds to lung slices with increasing number of carbons of the alkyl substituent. Pretreatment with a cytohrome P-450 inducer (β-naphthoflavone) increased the binding of NAP, 2-MN, and 2-IPN to lung slices.Treatments with NAP, 2-MN, 2-IPN and 2, 6-DIPN did not affect the lipid peroxidation or phospholipid contents in the lung.These results suggest that the difference in pulmonary toxicity among NAP, 2-MN, 2-IPN, and 2, 6-DIPN may be dependent on the ability of these compounds to irreversibly bind to lung tissue.View full abstractDownload PDF (2195K) -
Shoji KOJIMA, Minoru KAWAGOE, Morio KIYOZUMI, Hideaki SHIMADA1990 Volume 38 Issue 11 Pages 3136-3139
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Benzyl-D-glucamine dithiocarbamate (BGD), N-p-hydroxymethylbenzyl-D-glucamine dithiocarbamate (HBGD), and N-p-carboxybenzyl-D-glucamine dithiocarbamate (CBGD) were compared for their relative efficacies in the dustribution and excretion of cadmium in mice exposed to cadmium. Mice were injected intraperitoneally with 109CdCl2 (1 mg of Cd/kg and 2 μCi of109Cd/one animal). Three days later, they were injected with chelating agents (400 μmol/kg) every other day for 2 weeks. After injections of BGD and HBGD, cadmium was excreted mainly in the feces through the bile, and the fecal excretion of cadmium by HBGD was significantly higher than that by BGD or CBGD. These chelating agents increased the urinary excretion of cadmium to a small extent. The hepatic cadmium content was decreased only after HBGD injection. Also, the injection of HBGD caused a much greater decrease in renal cadmium content than did BGD or CBGD. These chelating agents did not result in the redistribution of cadmium to the brain, testes, or heart. The growth of mice was only slightly retarded by injections of these chelating agents. The results of this study indicate that the injection of HBGD to mice pretreated with cadmium can remove cadmium from the body, mainly through fecal excretion, without redistribution of cadmium to other tissues such as the brain, testes, and heart, more effectively than BGD or CBGD.View full abstractDownload PDF (667K) -
Takefumi MATSUKURA, Tamiko TAKAHASHI, Yasuhiro NISHIMURA, Takuzo OHTAN ...1990 Volume 38 Issue 11 Pages 3140-3146
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel crystalline Zn(II) complex of L-carnosine was prepared and evaluated for inhibitory activity against gastric ulceration in rats. The complex was found to be much more active than various other Zn(II) compounds. It was characterized by means of infrared (IR) spectroscopy, solid-state carbon-13 (13C) and nitrogen-15 (15N) 1H-cross-polarization (CP) magic angle spinning (MAS) nuclear magnetic resonance (NMR) spectroscopy and X-ray photoelectron spectroscopy (XPS). The spectroscopic data indicated that L-carnosine coordinates to Zn(II) as a quadridentate ligand. A comparison of the 13C-NMR signals of the imidazole carbons of the complex with those of several histidine derivatives revealed that a tautomeric change of imidazole moiety had occurred upon complexation.The binding mode of the complex was considered to be analogous to that of the corresponding Cu(II) complex.View full abstractDownload PDF (974K) -
Shigehiro KATAOKA, Nobuyuki YAMAJI, Motohiko KATO, Tomie KAWADA, Shoic ...1990 Volume 38 Issue 11 Pages 3147-3154
Published: November 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of novel N6, N6-dialkyl adenosine 3', 5'-cyclic phosphates (N6, N6-dialkyl cAMPs) was synthesized from 2'-O-p-toluenesulfonyl cAMP (2'-O-tosyl cAMP, 2) and tested for inotropic and chronotropic activities in vitro.Treatment of 2 with excess alkyl halides and sodium hydride followed by detosylation with aqueous NaOH readily gave N6, N6-dialkyl cAMPs (3) in good yields. Various N6, N6-dialkyl cAMPs having different alkyl groups at the N6-position (9-12) were prepared by alkylatin followed by detosylation of N6-alkyl-2'-O-tosyl cAMPs (4) which were obtained by the reductive alkylation of 2 with aldehydes in the presenve of sodium cyanoborohydride in acetic acid or tosylation of N6-methyl cAMP. The mechanism of the detosylation is briefly discussed. Among the N6, N6-dialkylated derivatives, N6, N6-dipentyl (3f) and N6-ethyl-N6-heptyl (10e) derivatives were found to exhibit a potent positive inotropic effect and a weak positive chronotropic effect. The structure-activity relationships for the position and the length of alkyl residue are discussed.View full abstractDownload PDF (1385K)