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Volume 39, Issue 6
Displaying 1-50 of 68 articles from this issue
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Yasuo OHTSUKA, Takeshi OISHI1991 Volume 39 Issue 6 Pages 1359-1364
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStereocontrolled synthesis of two twelve-membered lactam sulfides 37 and 38 as precurors of 8, 11, 11-trimethyl-3-oxobicyclo[5.3.1]undec-8-enes constituting the A and B rins of taxane-diterpenes was achieved.The keystep involves a Diels-Alder reaction of maleic anhydride and the E-diene 18 for introduction of the requisite cis arrangement of substitutions at the C-1 and C-7 positions.The resulting adduct was converted exclusively into the lactone 21b in five steps : 1) hydrolysis, 2) iodo-lactonization, 3) BH3 reduction, 4) Zn reduction, 5) methylation.The benzyl group of 26 could be selectively removed by heating with Raney Ni(W-2) in EtOH in nearly quantitative yield without hydrogenation of the double bond.View full abstractDownload PDF (987K) -
Yoshisuke TSUDA, Shinzo HSOI, Akira NAKAI, Yuki SAKAI, Tomoko ABE, Yuk ...1991 Volume 39 Issue 6 Pages 1365-1373
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 2, 8-dioxo-1, 7-cycloerythrinans with phenylselenenyl chloride in the presence of BF3·Et2O as a catalyst gave 3-chloro-3-phenylselenenyl derivaties through the 3-phenylselenenyl derivative, which changed into the Δ3-3-phenylselenenyl derivative on further reaction.Both the 3-phenylselenenyl and 3-chloro-3-phenylselenenyl derivatives gave the 3, 3-dimethoxy derivative on treatment with mercury (II) perchlorate (MPC) in methanol, thus providing a new method for introduction of a masked carbonyl group at the α-position to the original carbonyl group.Thus, the reaction of 1 with phenylselenenyl chloride under acidic conditions followed by MPC treatment in methanol and borohydride reduction gave the 2α-hydroxy-3, 3-dimethoxy derivative in 57% yield.This was converted to the conjugated ketone in four steps (72%).The carbomethoxy group of this compound was removed by the CaCl2-dimethyl sulfoxide-3-ethylpentane-3-thiol method to give the enone 4(70-80%) which isomerized to the conjugated ketone 25c(100%).This ws converted to a natural Erythrina alkaloid, (±)-erysotramidine (5), in four steps (31%), and thence to (±)-erosotrine (6).View full abstractDownload PDF (1483K) -
Hitoshi KUBOTA, Ken-ichi NUNAMI, Masafumi YAMAGISHI, Sigeru NISIMOTO, ...1991 Volume 39 Issue 6 Pages 1374-1377
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA diastereoselective syntesis of imidapril (1), which is under clinical study as an antihypertensive drug based on its angiotensin converting enzyme (ACE)-inhibitory activity, was established. N-Alkylation of (2S)-2-amino-4-phenylbutyric acid ester (12) with 3-((2R)-2-methane or toluenesulfonyloxypropionyl)-2-oxoimidazolidine derivative (11) diastereoselectively proceeded in an SN2 fashion to afford tert-butyl (4S)-3-[(2S)-2-[N-[(1S)-1-ethoxycarbonyl)-3-phenylpropyl]amino]propionyl]-1-methyl-2-oxoimidazolidine-4-carboxylate (13), a precursor of 1. Alternatively, benzyl (2S)-2-[N-(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propionate (15), which is the key building block of 13, was synthesized by teh same strategy. This procedure was also applied to the synthesis of enalapril.View full abstractDownload PDF (711K) -
Hiroshi KAYAKIRI, Shigehiro TAKASE, Toshihiro SIBATA, Masashi HASHIMOT ...1991 Volume 39 Issue 6 Pages 1378-1381
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of kifunensine, a new immunomodulator produced by a strain of Kitasatosporia, has been estabilished as 1 on the basis of chemical and physicochemical evidence and X-ray crystallographic analysis. Kifunensine is unique both in its novel structure, containing a 4, 5-dioxoimidazolidine ring included in the bicyclic framework, and in its potent immunomodulating activity. It is a representative of a new class of 1, 5-iminopyranoses.View full abstractDownload PDF (584K) -
Hitoshi MASUDA, Kazuhiro OHTANI, Kenji MIZUTANI, Susumu OGAWA, Ryoji K ...1991 Volume 39 Issue 6 Pages 1382-1384
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe sweet principle of an extract of heartwood of Haematoxylon campechianum was identified s hematoxylin (1), the well-known staining reagent already isolated from this plant. In addition to 1, two new dibenz[b, d]oxocim derivatives (2 and 3) were obtained. The structure of 2, named hematoxylol A, was elucidated as 3, 4, 10, 11-tetra-hydroxy-7, 8-dihydro-6H-dibenz[b, d]oxocin-7-one. The latter compound (3) was purified as a tetramethyl ether (3')named tetra-O-methylhematoxylol B and its structure was assigned as 7-hydroxy-3, 4, 10, 11-tetramethoxy-7, 8-dihydro-6H-dibenz[b, d]oxocin-7-methanol.View full abstractDownload PDF (545K) -
Masanori HONDA, Yoshitaka UEDA, Shigeo SUGIYAMA, Tetsuya KOMORI1991 Volume 39 Issue 6 Pages 1385-1391
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA cerebroside, 1-O-(β-D-galactopyranosyloxy)-(2S, 3S, 4R, 6E)-2-[(R)-2-hydroxytetracosanoylamino]-17-methyl-6-octadecene-3, 4-diol (2), was asymmetrically synthesized from isobutyraldehyde. On the basis of a comparison of the physical data, the absolute structure of a new cerebroside 1b from a Chondropsis sp. sponge is thought to be the same at that of 2.View full abstractDownload PDF (1271K) -
Hiroshi KAYAKIRI, Chiyoshi KASAHARA, Katsuya NAKAMURA, Teruo OKU, Masa ...1991 Volume 39 Issue 6 Pages 1392-1396
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSKifunensine (1), a novel immunomodulat isolated from an actinomycete, was enantiospecifically synthesized from D-mannosamine via a double cyclization of the oxamide-aldehyde precursor with ammonia as a key stop. The absolute stereochemistry of natural kifunensine was confirmed to be the D form.View full abstractDownload PDF (859K) -
Hiroshi KAYAKIRI, Teruo OKU, Masashi HASHIMOTO1991 Volume 39 Issue 6 Pages 1397-1401
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA synthesis of 8-epi-kifunensine (2) in optically active form was achieved starting from D-glucose via a modified double cyclization of the oxamide-hemiacetal precursor 9 with 2, 4-dimethoxybenzylamine as a key step.View full abstractDownload PDF (766K) -
Yoshisuke TSUDA, Yuki SAKAI, Takehiro SANO, Jun TODA1991 Volume 39 Issue 6 Pages 1402-1406
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 2, 7, 8-trioxoerythrinan derivatives with anhydrous phosphoric acid or Lewis acids gave 3, 7-cycloerythrinan derivaties via an intramolclar aldol condensation. The structures of the products were established by spectroscopic and chemical means. Further treatment of the 3, 7-cycloerythrinans with anhydrous phosphoric acid resulted in skeletal rearrangement to yield 6, 7-dihydro-4-oxo-4H-pyrido[2, 1-a]isoquinolines, whose structures were also determined mainly by spectroscopic means.View full abstractDownload PDF (750K) -
Taisuke ITAYA, Akemi MIZUTANI, Takehiko IIDA1991 Volume 39 Issue 6 Pages 1407-1414
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe phosphonium chloride 6 having an optically active amino acid moiety was synthesized from (S)-serine benzylester tosylate (2b) through a six-step route. The utility of 6 as a reagent for the Witting reaction was exemplified in the olefination with benzaldehyde, affording the (E)-β, γ-unsaturated amino acid derivative 11 as a sole geometrical ispmer. This new method of amino acid homologation was successuflly employed for the first chiral synthesis of wybutine (1c), the minor base isolated from yeast phenylalanine transfer ribonucleic acids : the Wittig reaction between 6 and the tricyclic aldehyde 16 followed successively by methylation and catalytic reduction afforded 1c. Comparison of wybutine with synthetic 1c has unequivocally established that wybutine has an S configuration.View full abstractDownload PDF (1355K) -
Naoki TAKEUTI, Toshio KASAMA, Yoko AIDA, Junji OKI, Izumi MARUYAMA, Ki ...1991 Volume 39 Issue 6 Pages 1415-1421
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn connection with the chemical structure of coumarin 1 (a mixture of acetylangeloylkhellactone and acetyltigloylkhellactone), a compound isolated from Peucedonum japonicum THUNB., we synthesized eight coumarin compounds (3-10) and performed pharmacological studies on these nince compounds, as well as on another coumarin, praeruptorin A (=Pd-Ia) (2), a compound isolated from Peucedaum praeruptorum DUNN. We studied the effects of compounds 1-5 on isolated smooth muscle and of compounds 1-10 on the cardiovascular system. These compounds showed dose-related antagonistic effects on histamine- and Ca2+-induced contractions in smooth muscle and the potencies were in the order 2>1>seselin (3)>xanthyletin (4)=2, 2, 0-trimethyl-2H, 8H-benzo[1, 2-b : 3, 4-b']dipyran-8-one (5). All the compounds except 7-geranyloxy-4-methylcoumarin (10) produced a dose-related increase in vertebral, carotid and femoral blood flow. Compounds 1, 5, and 4-methyl-7-(3-methyl-2-butenyloxy)coumarin (8) caused an increase in blood pressure, but 3 and 4 caused a slight decrease. Compounds 2, 3, 4, 5, and 8 increased heart rate. Jatamansinone (6) and jatamansinol (7) caused only slight changes in blood pressure. All the compounds except 10 increased heart rate. Compound 1 also increased blood flow in teh cerebral cortex. Thus, compound 1 was confirmed to have an inhibitory effect on contraction in isolated smooth muscle and an action increasing arterial blood flow. Among the compounds tested in this study, 3, as well as 6 and 7 synthesized on the basis of 3, showed actions similar to those of Ca2+ blockers and some compounds had papaverine-like activities. These results suggest that the chemical moiety of compound 3 may be the basis for the pharmacological activities of Peucedanum Japonicum THUNB.View full abstractDownload PDF (960K) -
Hiroshi KAWAI, Fumio SAKAMOTO, Masahiro TAGUCHI, Mikiya KITAMURA, Miki ...1991 Volume 39 Issue 6 Pages 1422-1425
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious 4-arylthiomethyl-2-oxo-1, 3-dioxole derivatives IIIa-o were synthesized. Their hydrolysis rates by arylesterase (EC 3.1.1.2) and cholinesterase (EC 3.1.1.8) in human serum were evaluated. Some of them were not hydrolyzed by cholinesterase, but were hydrolyzed easily by arylesterase.Among the substrates, sodium 4-((5-methyl-2-oxo-1, 3-dioxol-4-yl)methylthio)benzenesulfonate (IIIg) was selected for its substrate reactivity toward arylesterase and its good water solubility. In addition, neither aliesterase (EC 3.1.1.1), acetylesterase (EC 3.1.1.6) nor cholesterol esterase (EC 3.1.1.13)hydrolyzed the compound. IIIg is thus concluded to be a specific substrate for arylesterase.Our assay system for serum arylesterase using IIIg can be readily applied to an automatic analyzer in the diagnosis of liver cirrhosis.View full abstractDownload PDF (770K) -
Yoshiharu INAMI, Tatsuya TOMITA, Yukimasa TERADA1991 Volume 39 Issue 6 Pages 1426-1429
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSQuantitative structure-activity relationship analysis has been acoomplished on 24 derivatives of phencyclidine (PCP). By analysis with conceivable parameters effecting the variation of activity, it was shown that a compound with a smaller dipole moment, larger hydrophobicity, and a smaller principal moment of inertia is a stronger ligand of the receptor.By furthe examination of this fact, the direction of the dipole vector of the ligand molecule was demonstrated to be important for the activity. Consequently, an equation, which sufficiently explains the variation of the activity, was derived using the difference in direction of the dipole vector as the only parameter. This is the first quantitative analysis explanning the variation of activity of PCP derivatives.View full abstractDownload PDF (607K) -
Ikuo UEDA, Katsuyuki ISHII, Katsuo SINOZAKI, Masao SEIKI, Minoru HATAN ...1991 Volume 39 Issue 6 Pages 1430-1435
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-[3-{3-(Piperidinomethyl)phenoxy}propyl]butanamides having a 1-methyl-1H-tetrazol-5-ylthio moiety as a pharmacophore and related compounds were prepared and tested for their antisecretory activity against histamine-induced gastric acid secretion in conscious rats with gastric fistulas. Most of the compounds showed antisecretory activity. Among them, N-[3-{3-(piperidinomethyl)phenoxy}propyl]-4-(1-methyl-1H-tetrazol-5-ylthio)butanamide (5f) was found to possess the most potent activity, and a possibility of isosteric replacement of the methoxycarbonyl group with 1-methyl-1H-tetrazol-5-yl group was indicated. The structure-activity relationships are also discussed.View full abstractDownload PDF (1009K) -
Katsumi YAMAMOTO, Yoshikazu SHIINOKI, Jun FURUKAWA, Shoshiro NAKAMURA1991 Volume 39 Issue 6 Pages 1436-1439
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStructures of enactins Ia, Ib1, Ib2 and Va were determined by spectroscopic studies using their bis-2, 4-dinitrophenyl derivatives. Both enactins and neoenactins contain L-serine to form the hydroxamic acid structure. Their physico-chemical and biological properties are closely related. The structures of neoenactin congeners have been previosuly reported and enactins Ia and Va are proved to be 19-hydroxyneoenactin B2 and 14-dihydroneoenactin M1, respectively. Both enactins Ib1 and Ib2 are determined to be 19-hydroxyneoenactin B1 and considered to be diastereoisomers at the 19-position, though their steric structures at this positioin remain to be determined.View full abstractDownload PDF (643K) -
Yu MOMOSE, Kanji MEGURO, Hitoshi IKEDA, Chitoshi HATANAKA, Satoru OI, ...1991 Volume 39 Issue 6 Pages 1440-1445
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious analogues of a new antidiabetic agent, pioglitazone (AD-4833, U-72107), were synthesized in order to study in more detail the structure-activity relationships of this class of drug. 5-(4-Pyridylalkylthiobenzyl)-2, 4-thiazolidinediones (I), thia-analogues of pioglitazone, were prepared via Meerwein arylation of teh alkylthioanilines (IV). 5-(4-Pyridylalkoxybenzylidene)-2, 4-thiazolidinediones (IIa) and related heterocyclic analogues (IIb) were synthesized by Knoevenagel condensation of the aldehydes (VIII) with the corresponding azolidinones. Compounds I and II were evaluated for hypoglycemic and hypolipidemic activity in genetically obese and diabetic yellow KK (KKAy) mice. Several 5-[4-[2-(2-pyridyl)ethoxy]-benzylidene]-2, 4-thiazolidinediones (IIa) were equipotent to pioglitazone. However, the thia-analogues (I) and teh benzylideneheterocycles (IIb) had decreased activity. Catalytic hydrogenation of the 5-benzylidene analogue (14) was found to be a convenient new synthetic method for pioglitazone. The configuration of 14 is also discussed.View full abstractDownload PDF (890K) -
Seigo SAWADA, Satoru OKAJIMA, Ritsuo AIYAMA, Ken-ichiro NOKATA, Tomio ...1991 Volume 39 Issue 6 Pages 1446-1454
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNevel 36 derivatives (6), bonding the phenolic hydroxyl group of 7-ethyl-10-hydroxycamptothecin (4) with diamines through a monocarbamate linkage, were synthesized and their antitumor activity was evaluated in vivo. The derivatives were soluble in water as their HC1 salts wiht the E lactone ring intact and exhibited significant antitumor activity. One of the derivatives, 6-27 showed excellent activity against L1210 leukemia and other murine tumors.The structure of its hydrochloride trihydrate (CPT-11) was determined by spectroscopic and crystallographic methods.View full abstractDownload PDF (1305K) -
Kotaro IDAKA, Yasuaki HIRAI, Junzo SHOJI1991 Volume 39 Issue 6 Pages 1455-1461
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSteroid sponins and flavonoids of leavs of Phoenix rupicola T. ANDERSON, P. loureirii KUNTH, P. reclinate N. J. JACQUIN, and Arecastrum romanzoffianum BECCARI have been investigated. Tricin 7-O, β-D-glucopyranoside (I), vitexin (II), methyl proto-Pb (VII), methyl proto-taccaoside (26- O, β-D-glucopyranosyl (25R)-22-O-methyl-furost-5-en-3β, 26-diol 3-O-[α-L-rhamnopyranosyl-(1→2)][α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside, VI), and methyl proto-rupicolaside (26-O, β-D-glucopyranosyl (25R)-22-O-methy-furost-5-en-3β, 26-diol 3-O-[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)][α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside, VIII) from P. rupicola, II, glucoluteolin (III), orientin (IV), isoorientin (V), VII, VIII, and methyl proto-loureiroside (26-O-β-D-glucopyranosyl (25R)-22-O-methyl-furost-5-en-3β, 26-diol 3-O-[β-D-glucopyranosyl-(1→5)-α-L-arabinofu-ranosyl-(1→4)][α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside, IX) from P.loureirii, VII, VIII and methyl proto-reclinatoside (26-O-β-D-glucopyranosyl (25R)-22-O-methyl-furost-5-en-3β, 26-diol 3-O-[α-L-rhamnopyranosyl-(1→5)-α-L-arabinofuranosyl-(1→4)][α-L-rhamnopyranosyl(1→2)]-β-D-glucopyranoside, X) from P. reclinata, III and VII from A. romanzoffianum were isolated are identified. VI, VIII, IX and X were the first isolated and characterized from natural sources.View full abstractDownload PDF (1120K) -
Ken YASUKAWA, Michio TAKIDO, Tetsuro IKEKAWA, Fumitake SHIMADA, Mieko ...1991 Volume 39 Issue 6 Pages 1462-1465
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSForty eight derivatives of berberine-type alkaloids were examined for their inhibition activity against the induction of edema on mouse ear by application of 12-O-tetradecanoylphorbol-13-acetate (TPA). Berberine had an inhibitory effect against TPA-induced ear edema at a grade corresponding to those of quercetin, caffeine and cepharanthine.berberine derivatives had stronger inhibitory activity than palmatine derivatives. 9-N, N-Diphenylcarbamoyl derivatives of both 9-demethylberberine and 9-demethylpalmatine had rather strong activity. These inhibitory activities are about ten times the activity of the respective mother compounds. Furthermore, 9-N-monophenylcarbamoyl derivatives and N, N-diphenylcarbamoyl chloride are found to have no effectView full abstractDownload PDF (660K) -
Yuichi KIKUCHI, Yukinori MIYAICHI, Tsuyoshi TOMIMORI1991 Volume 39 Issue 6 Pages 1466-1472
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix flavonoids, named scutellaprostins A, B, C, D, E and F, were isolated from teh root of Scutellaria prostrata JACQ. ex BENTH. (Labiatae). Their structures were established to be (2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-phenyl-2, 3-dihydro-7H-1, 4-dioxino[2, 3-h]chromene-7-one (I), (2R*, 3*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(4-hydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino[2, 3-h]-chromene-7-one (II), (2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]chromene-7-one (III), (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-phenyl-2, 3-dihydro-6H-1, 4-dioxino-[2, 3-g]chromene-6-one (IV), (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-(4-hydroxyphenyl)-2, 3-dihydro-6H-1, 4-dioxino[2, 3-g]chromene-6-one (V) and (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-(3, 4-dihydroxyphenyl)-2, 3-dihydro-6H-1, 4-dioxino[2, 3-g]chromene-6-one (VI), respectively, by chemical and spectral data. They were synthesized by oxidative coupling of the flavones and coniferyl alcohol in the presence of silver oxide.View full abstractDownload PDF (1189K) -
Toshiyuki TANAKA, Munekazu IINUMA, Kaoru YUKI, Yuko FUJII, Mizuo MIZUN ...1991 Volume 39 Issue 6 Pages 1473-1475
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new β-hydroxychalcones named ponganones I and II were isolated from the root bark of Pongamia pinnata in Japan. The structures were characterized as 7-hydroxy-2', 5'-dimethoxy-[6", 6"-dimethylpyrano(2", 3" : 4', 3')]chalcone for ponganonse I, and 7-hydroxy-2', 5-dimethoxy-3, 4-methylenedioxy-[6", 6"-dimethylpyrano(2", 3" : 4', 3')]chalcone for ponganone II, respectively, by means of spectroscopic analysis.View full abstractDownload PDF (482K) -
Hideaki TANIMORI, Akira AKAHORI, Shinsuke SONOI, Tsunehiro KITAGAWA1991 Volume 39 Issue 6 Pages 1476-1479
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new immunoassay for a solid Chinese crude drug was studied. An antiserum specific for Pinellia tuber was elicited in two rabbits. Using the antiserum and powdered Pinellia tuber-coated microtiter plate as the immunological reagents, and β-D-galactosidase-labeled goat anti-rabbit immunoglobulin G (IgG) as the tracer, a new enzyme immunoassay for a solid Pinellia tuber with a working range between 0.1 and 1000 μg/ml was developed.The assay was specific for a solid Pinallia tuber and showed low cross-reaction values on other Chinese crude drugs and the extract of Pinellia tuber. The specificity of the assay was compared with the selected antibody enzyme immunoassay (SAEIA) for the extract of Pinellia tuber recently developed. Both methods untilized the same immunological reagents such as th serum and the enzyme-labeled goat anti-rabbit IgG, and theonly difference between them was the solid-phase antigen used. The assay results of several antigens determined by them were quite different, showing that selective measurements of different antigens, either solid or the extract of Pinellia tuber, were possible using the same antiserum, when the tracing reaction in the immunoassay was adequately selected.View full abstractDownload PDF (642K) -
Toshikatsu TOUKAIRIN, Keijiro UCHINO, Masaya IWAMOTO, Sachie MURAKAMI, ...1991 Volume 39 Issue 6 Pages 1480-1483
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew 5'-nucleotidase inhibitors designated as NPF-88BU-IA, NPF-88BU-IB, NPF-88BU-IIA and NPF-88BU-IIB, respectively, were i solated from the seeds and skin of th wine grape "Koshu". They were purified by solvent extraction, dialysis, and reversed-phase high performance liquid chromatography (HPLC).Their physico-chemical properties revealed these compounds to be polyphenolic substances.The average relative molecular masses of the four were estimated by gel permeation chromatography (GPC) analysis to be 7850, 5950, 11900, and 11300, respectively. They Strongly inhibited 5'-nucletidase activities from snake venom and rat liver membrane, and displayed significant therapeutic activity against Ehrlich ascites carcinoma. They also showed inhibitory effects on the growth of Streptococcus mutans MT8148(c), a primary cariogenic bacterium. Furthermore, these 5'-nucleotidase inhibitors inhibited the glucan formation from sucrose. These results suggest that the 5'-nucleotidase inhibitors can prevent the cause of caries of tooth.View full abstractDownload PDF (621K) -
Machiko MATSUBARA, Hisatora KURODA1991 Volume 39 Issue 6 Pages 1484-1488
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChitin- and chitosan-like substances were isolated from mycelia and conidia of Mycospharella (M.) pinodes, a plant pathogen of peas causing brown spots. The elicitor activities of these substances were compared with those of commercially available crustacean chitin and chitosan or several neutral polysaccharides. Only low activities were detected in the chitin-like substnaces of this microbe and in the authentic chitin commercially obtained. Although the activity was not detectable in chitosan oligomers whose degree of polymerization was less than 6, the acivity which appeared in the chitosan hexamer and the octamer had almost the same activity as the commercially available chitosan. All of the authentic neutral linear polysaccharides tested were inactive. After having applied M. pinode suspension on pea leaves, activities of both chitinase and chitosanase increased quickly. Fluorescein isothiocyanate (FITC)-labelled chitosan was treated with a crude extract of pea leaves, and FITC-oligomers were obtained.View full abstractDownload PDF (734K) -
Shinjiro ODAKE, Toru OKAYAMA, Masami OBATA, Tadanori MORIKAWA, Shunji ...1991 Volume 39 Issue 6 Pages 1489-1494
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo develop a potent and specific collagenas inhibitor, a series of tetrapheptidyl hydroxamic acids were synthesized, based on the previous findings with tripeptidyl derivatives (Chem. Pharm. Bull., 38, 1007-1011, 1990). Among the series of tetrapeptidyl derivatives synthesized, R-Gly-Pro-Leu-Ala-NHOH and R-Gly-Pro-D-Leu-D-Ala-NHOH were found to be highly specific and potent inhibitors against vertebrate collagenase with an IC50 of 10-6M order, where R stands for Boc or acyl group. Analysis of their structure-activity relationships showed a characteristic feature of the substrate-binding site of collagenase as follows : 1) the S1 subsite forms a shallow hydrophobic pocket, although glycine residue corresponds to the subsite of the natural collagen substrate : 2) the S2 substite constitutes a bulky pocket with less requirement for hydrophobicity : 3) the S3 subsitte preferentially accommodates Pro residue : and 4) the accommodation of the P4-P1 substites of peptidyl collagenase inhibitor to the S4-S1 substites is required to form a tight binding of its hydroxamic acid moiety to the zinc ion at the catalytic site of the enzyme. The introduction of an enantiometric dipeptide unit, D-Leu-D-Ala, to the P2-P1 subsites demonstrated an increased binding capacity to the extended S4-S1 subsites of collagenase, thus providing proteinase-resistant inhibitor.View full abstractDownload PDF (979K) -
Ikuo KASHIWAKURA, Yukitoshi HAYASE, Yoshinari TAKAGI1991 Volume 39 Issue 6 Pages 1495-1498
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPorcine kidney extracts (PKE) posses colony-promoting activity (CPA) which stimulates primitive hematopoietic cells in the presence of granulocyte/macrophage colony-stimulating factor (GM-CSF), but PKE itself does not stimulate colony formation on murine bone marrow cells.We have compared the CPA of PKE with that of recombinant cytokines or CSFs such as interleukin-1 alpha (IL-1α), IL-3, IL-6, granulocyte colony-stimulating factor (G-CSF), GM-CSF and macrophage colony-stimulating factor (CSF-1). All of these factors were less potent than PKE.Furthermore, the combinations of IL-1α or PKE with G-CSF, GM-CSF, IL-3 or IL-6 were examined in the presence of one of these factors such as CSF. It is found that PKE acts synergistically with G-CSF, GM-CSF, IL-3 and IL-6, showing enhancement ratios of 10, 2.5, 4.2 and 30, respectively. The combination of IL-1α resulted in poor colony formation in contrast with those of PKE, except for CSF-1.These results suggest that the CPA of the factor(s) in PKE differ from the cytokines and CSFs tested in this study, and is significantly affected by various types of CSF.View full abstractDownload PDF (687K) -
Hiroshi HOMMA, Tsutomu SASAKI, Michio MATSUI1991 Volume 39 Issue 6 Pages 1499-1503
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSome properties of androsterone (AD)-sulfating sulfotransferase (ST) present in female rat livers were characterized. Based on the substrate speciticities of the enzyme preparation obtained by anion exchange chromatography and 3'-phosphoadenosine 5'-phosphate (PAP)-agarose affinity chromatography, AD-ST was supposed to be among isoenzymes of hydroxysteroid STs. The identity of the AD-ST with the isoenzymes of hydroxysteroid ST, however, remains unclear at present. The enzyme preparation revealed a wide range of native molecular weight with a major Mr of some 600000. The AD-ST did not appear to have a homogeneous isoelectric point, because the enzmatic activity was spread over a wide range of the pH gradient, centering around pH 6.6 on chromatofocusing. On sodium dodecyl sulfate-polyacrylamide gel electrophoresis, the AD-ST showed a subunit with Mr of 30000, which was similar to the hydroxysteroid STs purified previously. Under denaturing conditions the subunit was demonstrated to be composed of three protein species containing distinct pI values (pI 6.1, 6.7 and 7.2). The AD-ST was thus supposed to be an oligomer with high molecular weight, in which the subunits of different pI values are assembled in various association numbers.View full abstractDownload PDF (1093K) -
Keiko SAKAI, Harumi OKUYAM1991 Volume 39 Issue 6 Pages 1504-1506
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-Linolenic acid (18 : 3n-3) is known to autoxidize several fold faster than linoleic acid (18 : 2n-6). Feeding a high α-linolenate or a high linoleate diet to rats resulted in significant changes in the n-3/n-6 ratios of 20 and 22 carbon highly unsaturated fatty acids in erythrocytes. However, the rates of hemolysis observed in N2- or O2-atmosphere were similar between the two dietary groups. No significant amounts of conjugated dienes were detected and no measurable changes in the fatty acid compositions were observed during the incubations, indicating that the hemolysis occurred without involving significant lipid peroxidation. When stimulated with a free radical initiator, [2, 2'-azobis-(2-amidinopropane)dihydrochloride] (AAPH), hemolysis occurred more rapidly, conjugated dienes formed and unsaturated/saturated ratios of phospholipid fatty acids decreased. However, no satistically significant difference was observed in these parameter of the two dietary groups. These results indicate that hemolysis occurs without involving lipid peroxidation but is accelerated by free radicals through lipid peroxidation, and that the difference in autoxidizabilities of α-linolenate and linoleate is not reflected in the rates of hemolysis and autoxidation in rat erythrocytes.View full abstractDownload PDF (602K) -
Toshiaki MIURA, Taketo OGISO1991 Volume 39 Issue 6 Pages 1507-1509
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLipid peroxidation of erythrocyte membrane was caused by phorbol myristate acetate (PMA)-stimulated polymorphonuclear leukocytes (PMN) in the presence of ferritin. PMN themselves were not peroxidized. A lag period was observed before the start of the peroxidation reaction. In contrast, ferritin iron was continuously released by PMA-stimulated PMN, suggesting that accumulation of free iron in the reaction system was importnat for processing of the peroxidation reaction. Superoxide dismutase, catalase, hydroxy radical scavengers and an iron chelator, diethylenetriaminepenta-acetic acid, inhibited the lipid peroxidation, indicating that the lipid peroxidation is initiated by a hydroxyl radical generated from the interaction of H2O2 with ferrous iron released from ferritin.View full abstractDownload PDF (566K) -
Yuko OHTA, Kazuhiko TAKAHASHI, Kohfuku KOHDA, Yutaka KAWAZOE1991 Volume 39 Issue 6 Pages 1510-1512
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral fluoroethyl derivatives of alkanesulfonates and N-nitrosourea were tested for cytotoxicity and mutagenicity in E. coli K12 AB1157. Cytotoxicity was potentiated by fluorine substitution in the alkyl moiety of the ethylating angents. Mutagenicity was storngly suppressed by fluorine substitution in the alkanesulfonates, but not in the N-nitrosourea.The capacity to induce the SOS repair network was suppressed, as was mutagenicity, in alkanesulfonates, but not in N-nitrosourea. The potentiating effect of fluorine on the cytotoxicity of alkanesulfonates seems to be due to an as yet unknown killing mechanism. An appreciable suppressive effect on the mutagenicity and the SOS induction is worth notice for the biological role of fluorine substitution in alkylating agents.View full abstractDownload PDF (609K) -
Yoshiro KOBAYASHI, Joost J. OPPENHEIM, Kouji MATSUSHIMA1991 Volume 39 Issue 6 Pages 1513-1517
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBoth pre-interleukin 1α and β (pre IL 1αand β) are proteolytically processed into extracellular mature forms of IL 1α and β. Since pre IL 1α and is shown to be biologically active, there may be other reasons for the proteolytic processing of IL 1α and presumably, for IL 1β also. In order to examine the possibility that structural stabilization may be associated with the proteolytic processing of pre IL 1α and β, we investigated the structural featuers of pre IL 1α and β by the combination of limited proteolysis and immunoprecipitation with antibodies to the NH2-terminal halves or COOH-terminal halves of pre IL 1α or β. Both trypsin and V8 protease digested the NH2-terminal halves of pre IL 1α and β more easily than the COOH-terminal halves of pre IL α and β, yielding structurally stabilized "mature" forms of IL 1. Both trypsin and V8 protease yielded a fragment similar in size to mature IL 1α from pre IL 1α. In contrast, trypsin digested pre IL 1β into fragments smaller in size tham mature IL 1β, while V8 protease yielded a fragment similar in size to mature IL 1β. Furthermore, mature IL 1β, once processed and released from cells, was resistant to trypsim. Since the COOH-terminal half of pre IL 1β is more susceptible to protease digestion than the extracellular mature form of IL 1β, which consists of the same COOH-half, the proteolytic processing of pre IL 1β appears to yield mature IL 1β with a more protease-resistant stable tertiary structure.View full abstractDownload PDF (1746K) -
Yutaka NISHIOKA, Syojiro KYOTANI, Masahiko KUSUNOSE, Hisashi MIMOTO, T ...1991 Volume 39 Issue 6 Pages 1518-1521
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCisplatic (CDDP) has attracted attentions as a chemotherapeutic agent for the treatment of uterine endometrial carcinoma but causes serious side effects, including renal toxicity.CDDP suppositories containing NaCl at different concentrations were prepared to enhanced the efficacy and to reduce the side effects of CDDP.The release characteristics, melting point and viscosity of the suppositories were first studied. The rate of CDDP release increased as the NaCl concentration increased : it was 12% 12h after administration of suppositories containing no NaCl, but 32% with 0.2% NaCl. The melting point was raised by addition of NaCl : 35.5°C without NaCl and 36.5°C with 0.2% NaCl. Addition of 0.2% NaCl doubled the viscosity. Chinically, the suppository containing 0.06% NaCl was given to 3 patients with endometrial carcinoma twice a week for 3 weeks to examine serum CDDP levels and endometrial absorption. Patients with endometrial carcinoma showed different peak plasma platinum (Pt) levels which were as low as 0.12, 0.06 and 0.22 μg Pt/ml with similar patterns of change in the level. Radiographic analysis revealed many Pt particles in sections of necrosed endometia after 21d of the treatment. No side effects of CDDP were found in biochemical testing or subjective symptoms.View full abstractDownload PDF (844K) -
Hiroshi KUKUCHI, Hitoshi YAMAUCHI, Sadao HIROTA1991 Volume 39 Issue 6 Pages 1522-1527
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA spray-drying method for the mass production of liposomes was developed : lipids were dissolved in a volatile organic solvent such as chloroform in which, in some cases, a core material such as mannitol was additionally suspended, and the organic solution or suspension was then spray-dried. Addition of core material particles or the use of hydrogenated lecithins increased the recovery of the lipid mixture prepared by spray-drying. Since the obtained spray-dried product was very amorphous, it could be easily hydrated with an aqueous solution, and lipid vesicles (lisopomes) were spontaneously formed by agitating. These spray-dried (SD) liposomes were characterized in comparison with the traditional liposomes known as Bangham's liposomes.Incorporation of cholesterol into the SD-liposomal membrane was confirmed by differential scanning calorimetry and gel filtraiton chromatography. Incorporation of charged lipids was confirmed by the zeta potential of liposomes.The size distribution of the unextruded SD-liposomes was similar to that of Bangham's liposomes, and a more homogeneous size distribution could be obtained by the extrusion technique. When glucose and dextran were used as water-soluble model drugs, the encapsulation efficiency was 15-65% depending on the total lipid concentration. Increasing the practical surface area of the lipid mixture using a core material was considered to cause a noticeably high encapsulation efficiency of dextran into the SD-liosomes.This spray-drying method was found to be useful and valuable for the mass production of liposomes.View full abstractDownload PDF (983K) -
Hirofumi TAKEUCHI, Hideo SASAKI, Toshiyuki NIWA, Tomoaki HINO, Yoshiak ...1991 Volume 39 Issue 6 Pages 1528-1531
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVitamin E acetate (VEA) was transformed into powdered form by a spray-drying technique and the water dispersible or drug releasing property of the dried particle was evaluated. The powdered VEA was prepared by spray-drying emulsified VEA with colloidal silica (Aerosil 200) and a disintegrant such as low-substituted-hydroxypropylcellulose (L-HPC). VEA in the spray-dried particle was chemically stable in storage longer than three years. On being dispersed in water with gentle shaking, the spray-dried particle released a large number of VEA droplets into the water, which formed a stable emulsion without additional stirring processes. This VEA releasing was mainly due to water uptake and swelling of the disintegrant formulated into the particle. The drug releasing property of the spray-dried particle significantly varied with the type of additives formulated, i.e., surfactant and disintegrant. The constituent ratio of the excipients (Aerosil 200 to disintegrant) influenced not only the VEA releasing but also the flowing property of the spray-dried particle. Based on these findings, an optimum formulation for the powdered VEA with both good drug releasing and flowing properties was established.View full abstractDownload PDF (1137K) -
Yoshinobu NAKAI, Keiji YAMAMOTO, Toshio OGUCHI, Etsuo YONEMOCHI, Takeh ...1991 Volume 39 Issue 6 Pages 1532-1535
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe inclusion compound of heptakis-(2, 6-di-O-methyl)-β-cyclodextrin (DMβCD) with benzoic acid was prepared by heating the ground mixture in a sealed container. The formation of teh inclusion compound was investigated quantitatively as a functions of heating temperature, heating time, and grinding time. Differential scanning calorimetry (DSC) measurements were made of the ground mixture at different grinding times. From teh DSC measurements, it was found that the temperature of crystallization of an amorphous ground mixture increased with an increase in grinding time. When the ground mixture was heated in a sealed container, the combining molar ratio of benzoic acid to DMβCD increased as the heating temperature increased. The experimental results indicated that the inclusion compound was obtained more effectively by heating the ground mixture rather than by heating the physical mixture.View full abstractDownload PDF (621K) -
Hiroshi ISHIHARA, Toshifumi HARA, Yukihiko ARAMAKI, Seishi TSUCHIYA, K ...1991 Volume 39 Issue 6 Pages 1536-1539
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction of recombinant human interferon-γ (IFN) with egg phosphatidylcholine liposomes was studied. IFN which binds to liposomes was dependent on the liposomal charge and pH, and a preferential binding was observed in negatively charged liposomes at pH 7.4-10. Electron-microscopic observation showed that the increased liposomal turbidity induced by IFN was due to liposomal aggregation, and the increased turbidity could be decreased by the addition of NaCl. Thus, ionic binding may participate in this interaction. But, when the incubation time was longer, the liposomal aggregation was not decreased by the addition of NaCl, and the leakage of the entrapped marker, calcein, was observed. Electron-microscopic analysis showed that this leakage resulted from the morphological change of liposomes. From these findings, ionic binding may participate in the interaction between IFN and liposomes and then develope a morphological change in negatively charged liposomes under the neutral pH condition.View full abstractDownload PDF (936K) -
Katsuaki KATO, Kazuo NAKAYAMA, Masahiro MIZOTA, Ichitomo MIWA, jun OKU ...1991 Volume 39 Issue 6 Pages 1540-1545
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSProperties and efficacies of novel aldose reductase (AR) inhibitors, M16209 (1-(3-bromobenzo[b]furan-2-ylsulfonyl)hydantoin) and M16287 (1-(3-chlorobenzo[b]furan-2-ylsulfonyl)hydantoin), were examined in vitro and in vivo, compared with known AR inhibitors, ONO-2235 and sorbinil. These four compounds inhibited partially purified aldose reductases from various origins, and the potencies of M16209 and M16287 were on the whole similar to ONO-2235, and were greater than that of sorbinil. The IC<50> values of the four AR inhibitors did not substantially depend on the substrate used. Kinetic studies of inhibition of partially purified bovine lens (BLAR) revealed taht M16209, M16287 and sorbinil were uncompetitive with glyceraldehyde and noncompetitive with nicotineamide adenine dinucleotide phosphate (NADPH), whereas ONO-2235 was noncompetitive with both glyceraldehyde and NADPH. Aldose reductase became less sensitive to the four inhibitors as enzyme purification progressed, although the susceptibility to inhibition was partially reversed by incubation with dithiothreitol. In addition, the four compounds slightly affected those enzymes of carbohydrate and glutathione metabolism which were tested. M16209 and M16287 prevented sorbitol accumulation in isolated rat tissues as potently as ONO-2235 and sorbinil. M16209 and M16287 were effective in the prevention of galactosemic cataracts and amelioration of diabetic neuropathy with almost the same potency, while ONO-2235 was effective only in neuropathy, and sorbinil was effective in galactosemic cataracts and diabetic neuropathy with a different potency. These results indicate that M16209 and M16287 are potent aldose reductase inhibitors, which could be applicable to treatment for diabetic complications.View full abstractDownload PDF (1132K) -
Isao KOHDA, Masakazu IWAI, Masahiro WATANABE, Yoshio ARAKAWA, Chikara ...1991 Volume 39 Issue 6 Pages 1546-1550
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe analogues of 2-(E-n or Z-n-decenoylamino)ethyl carbamoylmethyl sulfide, including the modifications of sulfide portion, double bond in decenoyl chain and alkyl sulfide moiety, were synthesized and their inhibitory effects on stress-induced ulceration in rats were compared.Replacing the sulfura atom by methylene group or oxygen atom reduced the effect of potency. Saturation of the double bond in the decenoyl chain tended to reduce the anti-ulcerogenic activity in rats. There was no relationship between the position of double bond in decenoyl chain and the pharmacological activity. On the other hand, compounds with E-configuration showed stronger anti-ulcer activity than the corresponding Z-type of compounds. Among 9 kinds of S substituted alkyl groups for carbamoylmethyl, 2-(E-2-decenoylamino)ethyl 2-cyclohexylethyl sulfide showed the most potent anti-ulcerogenic activity in rats and also showed the lowest acute toxicity in mice.View full abstractDownload PDF (861K) -
Nzunzu LAMI, Shigetoshi KADOTA, Tohru KIKUCHI, Yasunori MOMOSE1991 Volume 39 Issue 6 Pages 1551-1555
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo known lignans, liriodendrin and syringaresinol mono-β-D-glucoside, have been isolated from the methanol extract of the roots of Boerhaavia diffusa L. (Nyctaginaceae), and the former compound was found to exhibit a significant calcium (Ca2+) channel antagonistic effect in frog heart single cells using the whole-cell voltage clamp method.Reexamination of the carbon-13 nuclear magnetic resonance (13C-NMR) spectra of these compounds was also carried out by the use of two-dimensional NMR techniques including a 1H-detected heteronuclear multiple bond connectivity (HMBC) experiment, and it was found that the previous signal assignments for C-1' and C-4' have to be revised.View full abstractDownload PDF (778K) -
Motosuke YAMANAKA, Kazutoshi MIYAKE, Shinji SUDA, Hideto OHHARA, Toshi ...1991 Volume 39 Issue 6 Pages 1556-1567
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 1, 2-dihydro-5-imidazo[1, 2-α]pyridinyl-2(1H)-pyridonones was synthesized and evaluated for positive inotropic activity. 1, 2-Dihydro-5-imidazo[1, 2-α]pyridin-6-yl-6-methyl-2-oxo-3-pyridinecarbonitrile (11a) hydrochloride monohydrate (E-1020) was found to be a potent and selective inhibitor of phosphodiesterase III and a long-acting, potent, orally active positive inotropic agent. Additional imidazo[1, 2-α]pyridin-2-yl (3a), -3-yl (16), -7-yl (20) and -8-yl (24a) compounds were also prepared. Altering the pyridine substitution from the 2-position to the 6-position produced a 2-fold increse in the i.v. cardiotonic potency (ED50) from 52 to 23 μg/kg, while substitution at the 3-, 7- or 8-position reduced potency. In the 2-positional isomers, introduction of halogen groups enhanced the activity and 3-chloro-1, 2-dihydro-5-(6-fluoroimidazo[1, 2-α]pyridin-2-yl)-6-methyl-2(1H)-pyridinone (3u) was the most potent (i.v. ED50 11 μg/kg) in this series. E-1020 is presently under development for the treatment of congestive heart failure.View full abstractDownload PDF (1616K) -
Yoshiaki SHIRATAKI, Mami NOGUCHI, Ichiro YOKOE, Tsuyoshi TOMIMORI, Man ...1991 Volume 39 Issue 6 Pages 1568-1572
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new prenylflavanones, sophoraflavanones H, I and J, with resveratrol residues, were isolated from the roots of Sophora moorcroftiana (Leguminosae).The structures were determined by spectroscopic methods. Therefore, these were new types of natural products which, when combined with flavanones and stilbenes, were named flavonostilbenes.View full abstractDownload PDF (766K) -
Shoko YOKOYAMA, Fumio UEDA, Akiko KANEKO, Tadao FUJIE1991 Volume 39 Issue 6 Pages 1573-1575
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe heats of dissolution (ΔHd) of thiamine disulfide (TDS)-fatty acids (FA) complexes, (FA)6 (TDS), were measured at 310.15 K in ethanol using a calorimetric technique, where the FA are tetradecanoic acid (C14), pentadecanoic acid (C15), hexadecanoic acid (C16), heptadecanoic acid (C17) and octadecanoic acid (C18). The values of ΔHd were 432.8, 475.0, 493.3, 541.0 and 558.5 kJ mol-1 for (C14)6(TDS), (C15)6(TDS), (C16)6(TDS), (C16)6(TDS), (C17)6(TDS) and (C18)6(TDS), respectively. The values of ΔHd of (FA)6(TDS) increased by increasing the carbon numbers (n) of the constituent fatty acids. However, the plots of ΔHd of (FA)6(TDS) against n showed a zig-zag pattern which indicates an upward convex at an odd-numbered position, while the plots of ΔHd of FA against n indicate a single line pattern.The differences between ΔHd of (FA)6(TDS) and ΔHd of (6FA+TDS) were 23-37 kJ mol-1 for even-numbered FA and 33-41 kJ mol-1 for odd-numbered FA, indicating a stronger binding force for (FA)6(TDS) formed from odd-numbered FA than those formed from even-numbered FA. Furthermore, the estimated values for the binding force between FA and TDS are very small, leading to a conclusion that (FA)6(TDS) is a clathrate (or an inclusion compound) formed by van der Waals forces and hydrophobic interactions between FA and TDS.View full abstractDownload PDF (564K) -
Fumiko ABE, Tatsuo YAMAUCHI, Shiryo YAGA, Kazuo MINATO1991 Volume 39 Issue 6 Pages 1576-1577
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNine pyrrolizidine alkaloids includig three new compounds, were isolated from Parsonsia laevigate collected in Okinawa Island. No courtship pheromone with a dihydropyrrolizine framework was detectable in hair-pencil of Idea leuconoe, whose worms feed on the leaves of Parsonsia laevigata.View full abstractDownload PDF (467K) -
Zahid Hussain CHOHAN1991 Volume 39 Issue 6 Pages 1578-1580
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCobalt(II) and nickel(II) complexes of the antibacterial drug Ceclor have been synthesized and characterized on the basis of their elemental analysis, molar conductance, magnetic moment and electonric and infrared spectral data.These complex have been, then subjected to screening for their antibacterial properties against bacterial species such as Streptococcus pyogenes, Streptococcus pneumoniae, Staphylococcus aureus and Escherichia coli. In comparison to uncomplexed Ceclor, the metal complexes have been shown to be more antibacterial.View full abstractDownload PDF (498K) -
Syuji TSUKIYAMA, Atsushi HASHIMOTO, Souta KATAYAMA, Toru NISHIKAWA, Ak ...1991 Volume 39 Issue 6 Pages 1581-1584
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDerivatives with fluoromethyl and hydroxymethyl groups on the cyclohexyl ring of 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP), a noncompetitive antagonist of N-methyl-D-aspatrate (NMDA) receptor, were tested in a radioligand binding assay to evaluate their ability to inhibit [3H]TCP binding by rat brain homogenates. The potencies of these compounds as antagonists of NMDA and L-glutamate responses were also compared using a rat cortical slice preparation.One of the analogs, cis-2-hydroxymethyl-r-1-(N-piperidyl)-1-(2-thienyl)cyclohexane (5) was found to show a high affinity (IC50=16 nM) for the phencyclidine (PCP) binding sites, very close to that of TCP, and to be 38-fold more potent in binding than its trans isomer. Fluoromethyl and hydroxymethyl substitutions at C4 position of the cyclohexyl ring of TCP clearly reduced the affinity by at least one order of magnitude relative to TCP.View full abstractDownload PDF (695K) -
Yoshiki MINO1991 Volume 39 Issue 6 Pages 1585-1587
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new method for plant identification is proposed in which each ferredoxin (Fd) is isolated from small amounts of fresh leaves of five species of genus Datura and the tryptic digest of each S-carboxymethlated Fd is subsequently compared by peptide mapping using reversed-phase high-performance liquid chromatography (HPLC). This method makes it possible to analyze five samples in 4 or 5 d. The results obtained for th five plants indicate the HPLC patterns which reflect amino acid sequences of Fd to possibly be correlated to their morphological similarity.View full abstractDownload PDF (580K) -
Hiroshi KOHDA, Seiji TANAKA, Yasutoshi YAMAOKA, Hiromasa IZUMI, Mariko ...1991 Volume 39 Issue 6 Pages 1588-1590
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel saponin named chikusetsusaponin VI was isolated from the rhizome of Panax pseudo-ginseng var. angustatus HARA and its structure was determined as 20(S)-protopanaxadiol 3-O-β-D-glucopyranosyl(1→2)-[β-D-xylopyranosyl-(1→6)]-β-D-glucopyranosido-20-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside.View full abstractDownload PDF (503K) -
Kazushi SHINGU, Nobuhiro MARUBAYASHI, Ikuhiko UEDA, Shoji YAHARA, Tosh ...1991 Volume 39 Issue 6 Pages 1591-1593
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new withanolide, physagulin C was isolated from the methanolic extract of the fresh leaves and stems of Physalis angulata L. (Solanaceae) and the structure was determined to be (20S, 22R)-15α-acetoxy-5β(6), 16β(17)-diepoxy-4β, 14β-dihydroxy-1-oxo-witha-2, 24-trienolide by spectroscopic means and X-ray analysis.View full abstractDownload PDF (447K) -
Products from Nileprost, 5-Cyano-16-methylprostacyclin, and its β-Cyclodextrin Complex under HeatingMichiaki YONEDA, Yasushi OHKAWA1991 Volume 39 Issue 6 Pages 1594-1597
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSProducts from nileprost (NP) and its β-cyclodextrin (CD) complex under heating was investigated. Stability of NP under thermal conditions was improved by complexation. The product from the complex is an ester between the carboxyl group of NP and the hydroxyl group of CD, and the NP moiety is fixed at the interior of the cavity of the CD moiety. Main products from NP are also esters between two molecules.View full abstractDownload PDF (519K) -
Sadaki FUJIMOTO, Susumu ISHIMITSU, Satoru HIRAYAMA, Naoko KAWAKAMI, Ak ...1991 Volume 39 Issue 6 Pages 1598-1600
Published: June 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen phenylalanine was incubated with myeloperoxidase (MPO) and hydrogen peroxide (H2O2), p-tyrosine, m-tyrosine and o-tyrosine were identified as hydroxylated products. With inactivated MPO, no significant amount of tyrosines was formed. Tyrosine formation was dependent on reaction time and the MPO concentration. The addition of Cl- at lower concentration to the MPO-H2O2 system resulted in increase of tyrosine formation, though Cl- at higher concentration reduced the formation. The tyrosine formation by both MPO-H2O2 and MPO-H2O2-Cl- systems was significantly prevented by hydroxy radical scavengers such as mannitol, benzoate and foormate. Superoxide dismutase was also an effective inhibitor of tyrosine formation from phenylalanine by MPO-H2O2 system.View full abstractDownload PDF (567K)