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Volume 40, Issue 12
Displaying 1-49 of 49 articles from this issue
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Hideko INOUE, Yoshinobu BABA, Tohru MIYAJIMA, Mitsutomo TSUHAKO1992 Volume 40 Issue 12 Pages 3127-3132
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhosphorylation of phenols (phenol, catechol, resorcinol, hydroquinone, cresols, hydroxybenzoic acids, and nitrophenols) with inorganic sodium cyclo-triphosphate hexahydrate (P3m), Na3P3O9·6H2O, was carried out under various reaction conditions (pH, temperature, and molar ratio). (1)The main products of these reations were triphosphate derivatives of phenols produced by phosphorylation of a hydroxyl group. Reaction of catechol with P3m gave a five-membered cyclic phosphate formed by an intramolecular cyclization of a triphosphate derivative. (2)The optimum conditions for phosphorylation were found to be pH 12, and a molar ratio of P3m : phenols=1 : 5. (3)The pKa values of phenols strongly affected the reaction rate and yield. The reactivity of phenols increased with an increase in their pKa values. A hydroxyl group on phenols with a pKa value of more than 8 would be reactive with P3m. (4)The reactivity of ortho-substituted phenols was less than those of meta- and para-substituted phenols, owing to the steric hinderance of ortho-substituents. (5)The mechanism of the reaction in the phosphorylation of phenols with P3m is discussed.View full abstractDownload PDF (917K) -
Jun LI, Shigetoshi KADOTA, Yukio KAWATA, Masao HATTORI, Guo-Jun XU, Ts ...1992 Volume 40 Issue 12 Pages 3133-3137
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new glucosides, bungeiside-A, -B, -C, and -D, were isolated from the roots of Cynanchum bungei DECNE. The structures of the new compounds were determined by chemical and spectroscopic methods, including two-dimensional nuclear magnetic resonance (2D NMR) techniques, especially 1H-detected heteronuclear multiple-bond multiplequantum coherence.View full abstractDownload PDF (821K) -
Kayoko AMIMOTO, Kazuko YOSHIKAWA, Shigenobu ARIHARA1992 Volume 40 Issue 12 Pages 3138-3141
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fresh leaves of Ilex rotunda, were isolated four new saponins named ilexosides XXIX-XXXII, together with the known saponins pedunculoside, ziyu-glycoside I, suavissimoside F1 and chikusetsusaponin IVa. Their structures were established on the basis of spectral and chemical evidence.View full abstractDownload PDF (668K) -
Takeshi ITABASHI, Koohei NOZAWA, Makoto MIYAJI, Shun-ichi UDAGAWA, Sho ...1992 Volume 40 Issue 12 Pages 3142-3144
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new compounds related to azaphilones, designated falconensins A (1), B (2), C (3), and D (4), were isolated from the mycelium of Emericella falconensis, a new ascomycetous fungus isolated from Venezuelan soil. The structures of falconensins A to D (1-4) were confirmed by spectroscopic investigation and chemical correlations. These falconensins are the hydrogenated azaphilones.View full abstractDownload PDF (645K) -
Takehiro SANO, Jun TODA, Motoshi SHODA, Ryuzo YAMAMOTO, Hiromi ANDO, K ...1992 Volume 40 Issue 12 Pages 3145-3156
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA study directed to the total synthesis of β-erythroidine 1, a non-aromatic Erythrina alkaloid, was conducted based on a strategy involving construction of D-furanoerythrinan via Diels-Alder reaction of furodioxopyrroline and the conversion of the resulting furan to the δ-lactone via oxidative fission of the furan ring followed by one-carbon homologation. Oxidation of the furanoerythrinan 17 with N-bromoacetamide followed by treatment with Nafion-H gave the enol γ-lactone 27. Alkaline hydrolysis of 27 followed by methylation with diazomethane gave the keto-ester 31. Alkylation of 31a with dimethylsulfoxonium methylide gave 8-oxo-γ-erythrodine (5). One-carbon homologation of 31a by Yamakawa's method using chloromethyl phenyl sulfoxide resulted in the formation of 8-ozocycloerythroidine (6). Compounds 5 and 6 are structural isomers of natural 8-oxo-β-erthroidine (2).View full abstractDownload PDF (1840K) -
Takashi MICHIDA, Masahiro KYUHARA, Michiko NISHIYAMA, Yukihiro YOSHIMI ...1992 Volume 40 Issue 12 Pages 3157-3162
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS"Picnic-basket" porphyrins of a new type, that have a substituent in the interior of the pocket, were synthesized to study stabilization of the bound oxygen in hemoprotein models. Though these Co(II) porphyrins have enormous equilibrium constants for the formation of base adducts, hydrogen-bonding interaction with coordinated dioxygen is not as effective for stabilization of the metal-dioxygen bond as we had expected. The results suggest that doming of the porphyrin plane plays an important role in the binding of dioxygen.View full abstractDownload PDF (914K) -
Naoki NODA, Shigenori YODA, Toshio KAWASAKI, Kazumoto MIYAHARA1992 Volume 40 Issue 12 Pages 3163-3168
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new ether-soluble resin glycosides (jalapins), simonins I-V, have been isolated from the roots of Ipomoea batatas and characterized on the bases of chemical and spectral data. Simonim I is the first example of resin glycoside with aromatic acid (trans-cinnamic acid) as a component organic acid.View full abstractDownload PDF (928K) -
Masateru ONO, Takashi UEGUCHI, Hiroko MURATA, Toshio KAWASAKI, Kazumot ...1992 Volume 40 Issue 12 Pages 3169-3173
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFifteen new resin glycosides, marubajalapins I-XV, were isolated from the jalapin fraction of the aerial part (leaves and stems) of Pharbitis purpurea. Among them, the structures of marubajalapins I-VII have been determined on the basis of chemical and spectral data. They are the first examples of jalapins with operculinic acid E obtained previously as a minor glycosidic acid of the crude jalapin from Jalapae Braziliensis.View full abstractDownload PDF (755K) -
Yasuhiko SATO, Hideo NAKAI, Masao WADA, Tomishige MIZOGUCHI, Yasumaru ...1992 Volume 40 Issue 12 Pages 3174-3180
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSApplication of regioselective remote photocyclization of a pair system consisting of a phthalimide group and a methylthio group to a homologous series of N-substituted phthalimides (4 and 5) possessing a terminal sulfide function in the amide side chain was investigated. On irradiation, medium to large membered cyclic peptide-like compunds (6, 7 and 9), up to a thirty-eight membered ring product (6f), were synthesized in moderate yields.View full abstractDownload PDF (992K) -
Akira TAKAHASHI, Takeshi ENDO, Shigeo NOZOE1992 Volume 40 Issue 12 Pages 3181-3184
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRepandiol, a new cytotoxic diepoxide has been isolated from the mushrooms Hydnum repandum and H. repandum var. album. The chemical structure was elucidated as (2R, 3R, 8R, 9R)-4, 6-decadiyne-2, 3 : 8, 9-diepoxy-1, 10-diol on the basis of spectroscopic analysis. The structure was confirmed by the synthesis of optically active repandiol. Repandiol displayed potent cytotoxic activity against various tumor cells.View full abstractDownload PDF (639K) -
Akira TAKAHASHI, Tsutomu AGATSUMA, Mamoru MATSUDA, Tomihisa OHTA, Tets ...1992 Volume 40 Issue 12 Pages 3185-3188
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new cytotoxic substance, designated russuphelin A (1), has been isolated from the mushroom Russula subnigricans HONGO(Basidiomycetes). The structure was elucidated as 2, 6-bis(2, 6-dichloro-4-hydroxyphenyloxy)-1, 4-dimethoxy-benzene on the basis of spectroscopic data and confirmed by total synthesis.View full abstractDownload PDF (588K) -
Tsutomu MORIKAWA, Hirofumi SASAKI, Kazuya MORI, Motoo SHIRO, Takeo TAG ...1992 Volume 40 Issue 12 Pages 3189-3193
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSimmons-Smith reactions of fluoroallyl alcohols and their derivatives with excess Zn-Cu and CH2I2 or Et2Zn and CH2I2 provided fluorocyclopropane derivatives. Diastereoselective cyclopropanation of the fluoroallyl alcohol derivative obtained from (R)-2, 3-O-isopropylidene glyceraldehyde was successfully carried out to give the optically active fluorocyclopropane derivative in high selectivity (>98% de).View full abstractDownload PDF (847K) -
Akira TAKAHASHI, Rie KUDO, Genjiro KUSANO, Shigeo NOZOE1992 Volume 40 Issue 12 Pages 3194-3196
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTerphenyl compounds, tentatively named Bl-I (1), Bl-II (2), Bl-III (3), Bl-IV (4) and Bl-V (5), showing 5-lipoxygenase inhibitory activity have been isolated from the mushroom Boletopsis leucomelas (PERS.) FAYOD. On the basis of physico-chemical and spectral evidence, they were concluded to be a series of cycloleucomeloneleucoacetates.View full abstractDownload PDF (520K) -
Kimio FURUHATA, Haruo OGURA1992 Volume 40 Issue 12 Pages 3197-3200
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Acetyl-and N-glycolyl-2, 7-anhydroneuraminic acid were synthesized from methyl 5-acetamido-3, 5-dideoxy-2-thio-α-D-glycero-D-galacto-2-nonulopyranosonate in high yield. The structures and stereochemistry of these glycosanic sialic acids were elucidated from 1H-NMR spectra and X-ray crystal analysis. The ring systems of N-acetyl- and N-glycolyl-2, 7-anhydroneuraminic acid (1 and 10) were determined to have the same 2C5(D) conformation.View full abstractDownload PDF (716K) -
Tohru SAITO, Miyoko MURAKAMI, Tadaaki INADA, Hiromi HAYASHIBARA, Tozo ...1992 Volume 40 Issue 12 Pages 3201-3205
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn treatment with an excess of imidazole in boiling N, N-dimethylformamide (DMF) for 30 min, 9-ethyl-1-(2-hydroxyethyl)adenine hydrobromide (4a) afforded the corresponding 1-[2-(1H-imidazol-1-yl)ethyl]hypoxanthine derivative (13a) in 52% yield. The 1-(3-hydroxypropyl) homologue (4b) and 1-(2-hydroxyethyl)adenosine perchlorate (4c) reacted similarly with imidazole, giving the corresponding deaminated products (13b and 13c). Treatment of 4a with pyridine or thiophenol in boiling DMF also caused a similar deamination, furnishing the corresponding hypoxanthine derivative (16 or 17) with replacement of the hydroxy group by the nucleophile. The reaction of 4a with sodium ethoxide in boiling EtOH failed to cause deamination but gave the rearranged product (6a) in 95% yield. The free base (15) of 4a did not give the deaminated product (13a) when treated with imidazole in boiling DMF, and 4a alone was stable in boiling DMF for at least 30 min. On the basis of these results, a probable mechanism is proposed for the deamination.View full abstractDownload PDF (807K) -
Akito TANAKA, Kiyotaka ITO, Shigetake NISHINO, Yukio MOTOYAMA, Hisashi ...1992 Volume 40 Issue 12 Pages 3206-3213
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5-Alkyl-2-aryl-4-pyridylimidazoles were synthesized and tested in rat ex vivo platelet aggregation studies. Among these compounds, 2-(2-fluorophenyl)-5-methyl-4-(3-pyridyl)imidazole (25) was most potent, and showed 98% inhibition at a dose of 10 mg/kg (p.o.). 25 had inhibitory activity on cyclooxygenase, thromboxane A2 (TXA2) synthetsase, and phosphodiesterase, and also showed inhibited KCl-induced contraction of rat aorta. All compounds have little acute toxicity and appear to be free of adverse effects on the stomach.View full abstractDownload PDF (1005K) -
Shugo ATSUUMI, Masato NAKANO, Yutaka KOIKE, Seiichi TANAKA, Hiroshi FU ...1992 Volume 40 Issue 12 Pages 3214-3221
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis and structure-activity relationships of N-terminus modified renin inhibitors containing the homostatine analogue, (2RS, 4S, 5S)-5-amino-2-ethyl-4-hydroxy-7-methyloctanoic acid, are described. The compounds having a 3-alkyl (or aryl)sulfonylpropionyl residue at the N-terminus are found to be potent inhibitors which contain two amino acids. (2RS, 4S, 5S)-N-Isobutyl-5-[N-[(2S)-3-ethylsulfonyl-2-(1-naphthylmethyl)propionyl]-L-norleucyl]-amino-2-ethyl-4-hydroxy-7-methyloctanamie (20) has an IC50 of 0.5 nM against human plasma renin and the oral bioavailability of 20 is 0.73% in rats. Interaction between renin and the N-terminus of 1 and 20 is discussed in molecular modeling studies.View full abstractDownload PDF (1227K) -
Rosa NENDEZ, Teresa ALEMANY, Javier MARTIN-VILLACORTA1992 Volume 40 Issue 12 Pages 3222-3227
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe catalytic effect of various buffer systems (citrates, acetates, phosphates, borates and carbonates) on the degradation of aztreonam and nocardicin A in aqueous solution was studied at 35°C and a constant ionic strength of 0.5 mol·dm-3 over a pH range of 3.50 to 10.50. The observed degradation rates, obtained by measuring the remaining intact antibiotic, were shown to follow pseudo-first-order kinetics with regard to antibiotic concentrations and to be influenced by general acid and general base catalysis. The changes in the concentration of intact β-lactam antibiotic in the solutions were established by reverse-phase HPLC with UV-detection. In general the buffer systems employed in the kinetic studies showed a very weak catalytic effect on the degradation of aztreonam and nocardicin A. The pH-rate profiles for these antibiotics showed degradation minimums at pH 5.38 and 6.13, respectively. Aztreonam is slightly more reactive with hydrogen ions than nocardicin A and is much more reactive with hydroxide ions. In comparison with other β-lactamic antibiotics, aztreonam and nocardicin A are much more stable in aqueous solution, except for aztreonam in a base solution, wich is just as unstable as penicillins and cephalosporins. The Arrhenius activation energies were determined for aztreonam and nocardicin A at pH's 4.23, 6.59 and 8.60.View full abstractDownload PDF (825K) -
Rosa MENDEZ, Teresa ALEMANY, Javier MARTIN-VILLACORTA1992 Volume 40 Issue 12 Pages 3228-3233
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Zn2+-tris (hydroxymethyl)aminomethane (Tris) system has a great catalytic effect on the hydrolysis and aminolysis of some β-lactam antibiotics. In order to ascertain the mechanism of this catalysis we have analysed the effects of the β-lactam antibiotic structure. First we studied the kinetics of the decomposition of imipenem, SCH 29482, aztreonam and nocardicin A in aqueous solution of Tris at 35.0°C, 0.5 mol·dm-3 ionic strength and in the presence of metal ions (Zn2+, Cd2+, Co2+, Cu2+, Ni2+ and Mn2+). From these studies, we conclude that Tris and metal ions (in separate solutions) exert a great catalytic effect on the hydrolysis of imipenem and SCH 29482. We suggest that in metal ion solutions a 1 : 1 complex is formed between the metal ion and β-lactam antibiotic, which is attacked by hydroxide ions.Studies of the degradation of the antibiotis studied in solutions of Tris and metal ions together indicate that the systems Cd2+-Tris and Zn2+-Tris have a great catalytic effect on the hydrolysis and aminolysis of imipenem and SCH 29482. we suggest that this catalysis takes place via a ternary complex in which the metal ion plays a double role by (a) placing the antibiotic and the Tris in the right position for the reaction and (b) lowering the pKa of the hydroxide group of Tris, which is coordinated with the metal ion, generating a strong nucleophile.View full abstractDownload PDF (809K) -
Fumiyuki KIUCHI, Satomi NISHZAWA, Hiromi KAWANISHI, Sayuri KINOSHITA, ...1992 Volume 40 Issue 12 Pages 3234-3244
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe nematocidal activity of amides and amines having a long alkyl chain against the second-stage larva of dog roundworm, Toxocara canis, was examined. Long chain acyl amides with samller substituents on the nitrogen showed stronger activity and the activity of cyclic amine amides was stronger than that of acyclic ones. In a series of homologous amides, the activity was dependent on the alkyl chain length : it reached a maximum at an optimal chain length and decreased in both shorter and longer homologues. The relationship between the activity and hydrophobicity of the homologues was analysed by the use of the bilinear model. The hydrophobicity of a compound, which gives a maximal activity, was similar for all neutral amides, but amides which have an additional amine group in the molecule had different values. Tertiary amines and their salts having a long alkyl chain also showed nematocidal activities comparable to those of the corresponding amides. The salts killed the larva at concentrations lower than their critical micell concentration, suggesting that they behave as a single molecule for the nematocidal action.View full abstractDownload PDF (1472K) -
Fumio SUZUKI, Takeshi KURODA, Hiroaki HAYASHI, Yoshisuke NAKASATO, Har ...1992 Volume 40 Issue 12 Pages 3245-3252
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of novel 3-substituted imidazo[4, 5-c]quinolin-4(5H)-ones (2a-w) was prepared by the reaction of imidazo[4, 5-c]quinolin-4(5H)-ones (6) with several electrophiles under basic conditions. The bronchodilatory activity of these compounds was evaluated on the basis of their protective effects against antigen-induced contraction (the Schultz-Dale reaction) of guinea-pig trachea (in vitro) and antigen inhalation-induced bronchospasm in passively sensitized guinea-pigs (in vivo). Although correlations between in vitro and in vivo activities were not clear, short alkyl chains such as the methyl and ethyl groups at the 3-position were important for potent activity, especially in vivo. Substituents at the 5-position were more tolerant of the activity than those at the 3-position. 5-Ethyl-3-methyl-3H-imidazo[4, 5-c]quinolin-4(5H)-one (21) exhibits the most potent bronchodilatory activity among our tested compounds and is at least 5-fold more active than theophylline in vivo.View full abstractDownload PDF (1042K) -
Koichi KAWASAKI, Katsuhiko HIRASE, Masanori MIYANO, Toshiki TSUJI, Mas ...1992 Volume 40 Issue 12 Pages 3253-3260
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Terminal tetrapeptide analogs of fibrin α-chain were synthesized by the solution method using a new active ester, the ester of the oxime of p-nitroacetophenone, and by the solid-phase method. Their inhibitory effects on fibrinogen/thrombin clotting were examined. Of the synthetic peptides, amide analogs of Gly-Pro-Arg-Pro exhibited a more potent inhibitory effect.View full abstractDownload PDF (1608K) -
Setsuo SAITO, Koki ICHINOSE, Yuka SASAKI, Shigeya SUMITA1992 Volume 40 Issue 12 Pages 3261-3268
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of β-and α-pyranose with PCl5 gave products regioselectively chlorinated. The reactions of 1, 2, 3, 4, 6-penta-O-acetyl-β-D-glucopyranose (5) and -β-D-galactopyranose (6) with PCl5 in CCl4 and that of methyl 2, 3, 4-tri-O-acetyl-β-D-glucuranatopyranose (7) with PCl5 in toluene gave 2-O-trichloroacetyl-β-D-pyranosyl chlorides 4, 12 and 14, respectively, as major products, and α-D-pyranosyl chlorides 11, 13 and 15, respectively, as minor products. On the other hand, the reactions of compounds 8 and 9 which were α-anomers of 5 and 6, respectively, with PCl5 gave as major products transformed acetyl groups at C-6 to -C(Cl)=CCl2 or -C(Cl)2-CCl3 group (16 and 17 from 8 and 18 from 9). The same reaction of 10, which was α-anomer of 7, gave α-chloride 15 as major product. The glycosidation of sugar derivative 4 with sarsasapogenin 23 gave β-glycoside 24 (29.1%) and α-glycosides 25 (46.9%), and that of 12 with 23 gave β-glycoside 26 (24.0%) and α-glycoside 27 (40.8%). The improvement of the yields of β-glycosides 24 and 26 (66.9 and 62.1% for 24 and 26, respecitvely) in the glycosidations were accomplished by the employment of α-bromides 28 and 29 obtained from 4 and 6, respectively. The glycosidations of monoglycosides 30 and 31 obtained by the treatment 24 and 26, respectively, with ammonia-saturated ether with sugar acetate bromides 32 and 34 gave diglycoside derivatives 35 and 33, respectively.View full abstractDownload PDF (1127K) -
Junei KINJO, Kaoru ARAKI, Katsura FUKUI, Hiroyuki HIGUCHI, Tuyoshi IKE ...1992 Volume 40 Issue 12 Pages 3269-3273
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix new triterpenoid glycosides called julibrosides A1-A4, B1 and C1 were isolated from Albizziae Cortex, the dried stem bark of Albizzia julibrissin DURAZZ. Their structures were determined based on spectral and chemical evidence. Julibrosides B1 and C1 had new sapogenols, designated julibrogenin B and C, respectively, while julibrosides A3 included N-acetyl-D-glucosamine as a sugar component.View full abstractDownload PDF (824K) -
Munehisa ARISAWA, Hua BAI, Shoji SHIMIZU, Saburo KOSHIMURA, Motohiro T ...1992 Volume 40 Issue 12 Pages 3274-3276
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA cytotoxic principle was newly isolated from Chrysosplenium grayanum MAXIM. (Saxifragaceae) and identified as β-peltoboykinolic acid (1) on the basis of spectral data. Cytotoxicity of compound 1 was tested against various human cancer cell lines in vitro, and antitumor effect of this compound was demonstrated on Meth·A mouse fibrosarcoma. The experiment of combined treatment with compound 1, mitomycin C, and OK-432 resulted in enhancing the antitumor effect against B16-BL6 mouse melanoma in C57BL/6 mice.View full abstractDownload PDF (573K) -
Yasunori YAOITA, Kimiko NAGATA, Noriko SUZUKI, Masao KIKUCHI1992 Volume 40 Issue 12 Pages 3277-3279
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new eremophilenolides, 6β-angeloyloxy-3β-hydroxyeremophil-7(11)-en-12, 8β-olide (1), 3β-hydroxy-6β-tigloyloxyeremophil-7-(11)-en-12, 8β-olide (2) and 3β, 6β-diangeloyloxyeremophil-7(11)-en-12, 8β-olide (3), were isolated from the dried rhizomes of Petasites japonicus MAXIM. (Compositae) with four known sesquiterpenoids. The structures of these compounds were elucidated on the basis of spectroscopic evidence.View full abstractDownload PDF (578K) -
Toshihiro AKIHISA, Wilhelmus C. M. C. KOKKE, Jeanette A. KRAUSE, Drake ...1992 Volume 40 Issue 12 Pages 3280-3283
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new triterpene isolated from the seeds of Trichosanthes kirilowii (Cucurbitaceae) was proposed to be 5-dehydrokarounidiol [D : C-friedo-oleana-5, 7, 9(11)-triene-3α, 29-diol, its 3-O-benzoate, and 7-oxo-D : C-friedo-olean-8-ene-3α, 29-diol, hasd previously been isolated from the same source. The structure was confirmed by X-ray analysis of the corresponding diacetate. This is the first report of a naturally occurring triterpene possessing a Δ5, 7, 9(11)-conjugated triene system.View full abstractDownload PDF (643K) -
Fumiyo KUSU, Xian-Duan LI, Kiyoko TAKAMURA1992 Volume 40 Issue 12 Pages 3284-3286
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHigh-performance liquid chromatography (HPLC) with electrochemical detection was used to determine synephrine (SYN) and N-methyltyramine (NMT) in Zhishi (Kijitsu ?? ?? ) and Zhike (Kikoku ?? ?? ). This electrochemical detection method has not only specific selectivity but also very high sensitivity, thus facilitating the determination of SYN and NMT from pulverized Zhishi and Zhike damples. Zhishi and Zhike derived from Citrus aurantium produced in different districts in China were analysed. This method was found useful for evaluating the quality of a crude drug such as Citrus aurantium.View full abstractDownload PDF (502K) -
Hitoshi NAKAYAMA, Shigeki YAMAMOTO, Yasumaru HATANAKA, Tetsuaki HACHIS ...1992 Volume 40 Issue 12 Pages 3287-3291
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCarbohydrate chains on the large peptide of the voltage-sensitive sodium channel from Electrophorus electricus electroplax have been partially characterized by the lectin-blotting technique combined with digestion using three glucosidases : neuraminidase, engo-β-N-acetylglucosaminidase H, and peptide : N-glycosidase F. The results show that both N-linked oligosaccharides and O-linked (mucin-type) oligosaccharides are present. In N-linked oligosaccharides, the results suggest the presence of complex-and hybrid-type oligosaccharides which contain bisecting N-acetylglucos-amine(s), as well as the complex-type oligosaccharides with the α-Fuc-GlcNAc-(Asn) residue(s). In O-linked oligosac-charides, they must carry Galβ1→3GalNAc- moieties which contain NeuNAc residues in the terminal.View full abstractDownload PDF (985K) -
Kiyohito YAGI, Tadashi SETO, Masakazu TERAKADO, Fusako UMEDA, Takefumi ...1992 Volume 40 Issue 12 Pages 3292-3296
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe nucleotide sequences of membrane-bound hydrogenase small (hupS) and large (hupL) subunit genes of hydrogen bacterium Alcaligenes hydrogenophilus were determined. The hupS and hupL genes encoded polypeptides of 363 and 619 amino acids, respectively. The hupS was located upstream of hupL with 35 bp of intergenic region. The consensus ribosome-binding sequrnces were identified upstream of the start codons of hupS and hupL. Amino acid sequence of hupS is very similar to that of Rhodobacter capsulatus, Bradyrhizobium japonicum, and Azotovacter vinelandii at amino acid lvevels of 82%, 77%, and 81%, respectively. Similarly, amino acid sequence of HupL is similar to that of R. capsulatus, B. japonicum, and A. vinelandii at amino acid levels of 63%, 65%, and 68%, respectively. Northern hybridization analysis showed that hupS and hupL were co-transcribed, and addition of fructose to the culture medium remarkably decreased the amount of mRNA transcribed from hupS and hupL.View full abstractDownload PDF (1139K) -
Hiroyuki KANEKI, Mitsuya TANAKA1992 Volume 40 Issue 12 Pages 3297-3302
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRhizopus delemar C-lipase (E) binds 1, 1, 1-trichloro-2, 2-bis(4-chlorophenyl)ethane (D or DDT) to form stable 1 : 1, 2 : 1 and 9 : 1 DDT-lipase complexes as follows.[table]Competitive binding experiments with a mixture of E and ED and that of E and E'D2 yielded κ1 : κ2 : κ4=80 : 1 : 400. The κ2 value was estimated to be 1.6×108 M-1s-1 by following the decrease in [ED] at a low concentration of reactants, ED and DDT, where the reaction was terminated at a given time by scavenging DDT with the addition of excess E'D2. The κ3 value, 0.021s-1, was determined by follwoing the formation of E'D2 from ED2 in the presence of ED. E'D2 was estimated by converting E'D2 rapidly into E*D9 by adding an adequate amount of DDT (ED2 cannont bind DDT), and the excess free DDT was depleted by the pre-existing ED to stop E*D9 formation from newly born E'D2.The continuous slow addition of a limited amount of DDT to ED made the rate of the second order reaction, ED to ED2, comparable to the rate of the slow first order reaction, ED2 to E'D2, thereby favoring the formation of E*D9. The estimation of κ2 and κ3 from the variation in the final population of each DDT-lipase species as a function of the rate of ligand addition was described.View full abstractDownload PDF (931K) -
Kazuyoshi SAGARA, Yuko NAGAMATSU, Ichimaro YAMADA, Miwako KAWATA, Hiro ...1992 Volume 40 Issue 12 Pages 3303-3306
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe gastrointestinal (GI) physiology of beagle dogs was regulated with a combined-treatment of intramuscular pentagastrin (10 μg/kg×2) and intravenous atropine sulfate (0.02 mg/kg×1). Here, the gastric acidity, the gastric emptying time and the small intestinal transit time in the regulated-dogs were respectively around pH 2, 0.7h and 4h, approximating those in healthy humans. The superiority of the regulated-dogs over the intact dogs was confirmed in comparative bioavailability studies by using two classes of commercial preparations. Both the conventional tablet and the sustained-release capsule of diclofenac sodium exhibited simple and similar average plasma concentration-time curves of free diclofenac in the intact dogs, while the latter preparation is reported to reveal a bimodal plasma curve of the drug in healthy humans. The regulated-dogs, however, permitted a bimodal average plasma pattern of the drug for the capsules due to an approximation of the GI physiology between humans and these classes of the dogs. The combined-treatment of beagle dogs with pentagastrin and atropine sulfate seems to supply a useful animal model in predicting the absorption characteristics of the sustained-release preparations and poor water-soluble drugs.View full abstractDownload PDF (775K) -
Masahiro OKUDA, Mikihisa TAKANO, Masato YASUHARA, Ryohei HORI1992 Volume 40 Issue 12 Pages 3307-3310
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism of a gentamicin-induced decrease in apical membrane enzyme activities was investigated in LLC-PK1 cells. Increasing activities of apical membrane enzymes (alkaline phosphatase, aminopeptidase, and γ-glutamyltransferase) were mrkedly suppressed by gentamicin during growth in culture. On the other hand, a lesser effect was observed when the activities of these enzymes were decreasing or relatively constant. Gentamicin treatment decreased the maximal enzyme activities of alkaline phosphatase and aminopeptidasem indicating that the number of active enzyme molecules in the apical membrane was decreased by gentamicim. [3H]Leucine incorporation in LLC-PK1 cells was inhibited by gentamicin in a dose-dependent manner, followed by a reduction of total protein. In addition, a well-known protein synthesis inhibitor, cycloheximide, also decreased the apical enzyme activities. These results suggest that the inhibition of protein synthesis by gentamicin is a possible cause of the decreased activities of apical membrane enzymes in LLC-PK1 cells. The inhibition of protein synthesis may be related to the nephrotoxicity induced by aminoglycoside antibiotics.View full abstractDownload PDF (770K) -
Yasuko KOMATA, Akiko KANEKO, Tadao FUJIE1992 Volume 40 Issue 12 Pages 3311-3313
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe solubility change of thiamine disulfide (TDS) in 1, 2-dichloroethane by the addition of fatty acid (FA), fatty alcohol or fatty acid methyl ester was determined by phase solubility analysis at 25°C. The solubility of TDS increased linearly with added concentrations of stearic acid, palmitic acid or myristic acid, but the diagram did not exhibit a plateau due to the appearance of a solid complex. The dependency of the FA slope values on the number of carbon atoms in FA was very little. The solubility of TDS also incerased linearly with added concentrations of stearyl alcohol, while the value for the slope was smaller than FA. On the other hand, the solubility of TDS decreased by the addition of stearic acid methyl ester. The results agreed well with those for the solubilization of cycotiamine, a thiamine derivative, by FA and FA analogs in 1, 2-dichloroethane.View full abstractDownload PDF (497K) -
Nobuo OKABE, Misa HOKAZE1992 Volume 40 Issue 12 Pages 3314-3315
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThyroid hormone, thyroxine (T4) binding properties of glycosylated bovine serum albumin (G-BSA), and intact BSA were studied by the fluorescence method. The apparent binding constants for intact BSA were 0.8 (0.16)×106M-1 at pH 5.0 and 2.18 (0.06)×106M-1 at pH 9.5 at 25°C. T4 binding for G-BSA was independent of pH and the apparent binding constant was 1.4×106M-1. Thermodynamic parameters were also evaluated from the Van't Hoff plots of the apparent binding constants at pH 7.4 and 8.5. At both pH's, the free energy, enthalpy and entropy changes were almost the same for both G-BSA and BSA.View full abstractDownload PDF (378K) -
Patrycja DYNAROWICZ, Wojciech JAWIEN1992 Volume 40 Issue 12 Pages 3316-3318
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThis paper presents a method for determination of the parameter β related to the molecular interaction between two surface active compounds in the mixture. The co-adsorption of phenol para-derivatives, which are well known in medicine and pharmacy as commonly used antiseptic drugs, was investigated. The surface properties of p-methylphenol, p-chlorophenol and p-bromophenol, as well as their mixtures, studies on the basis of surface tension measurements, have been related to their pharmacological action.View full abstractDownload PDF (523K) -
Toshihiko OZAWA, Akira HANAKI1992 Volume 40 Issue 12 Pages 3319-3320
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of Cu(II) ion with quinone, 5, 15-di-(3, 5-di-tert-butyl-4-hydroxyphenyl)-10, 20-di-(3, 5-du-tert-butyl-4-quinomethen)porpho-10, 20-dimethene (2) were investigated using UV/vis and electron spin resonance (ESR) spectroscopic methods.Formation of tetrakis(3, 5-di-tert-butyl-4-hydroxyphenyl)porphyrinatocopper(II) [Cu(II)TtBHPP, 4] from the reaction of Cu(II) ion with 2 was determined by UV/vis and ESR measurements. However, the direct reaction product, Cu(II)-quinone complex (3), was not detected. These results suggest that 3 which may be formed at the initial reaction step between Cu(II) ion and 2 is gradually reduced by excess Cu(II) ion to yield 4. The reaction scheme between Cu(II) ion and the quinone is discussed.View full abstractDownload PDF (401K) -
Masahiro KAJIWARA, Ken-ichiro HARA, Minoru MIZUTANI, Masao KONDO1992 Volume 40 Issue 12 Pages 3321-3323
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCultured broth of Saccharopolyspora erythraea shows a strong red fluorescence. The main fluorescent component was identified as uroporphyrin I by FAB-MS and 1H-NMR. This was confirmed by a feeding experiment using [5-13C]aminolevulinic acid.View full abstractDownload PDF (452K) -
Masaru KIDO, Teruyoshi ICHIHARA, Hideaki OTSUKA, Yoshio TAKEDA1992 Volume 40 Issue 12 Pages 3324-3326
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe conformation and the absolute stereochemistry of macrocalyxoformin D (=longirabdiol) was determined based on nuclear magnetic resonance spectroscopy, X-ray crystallographic analysis and circular dichroism spectroscopy.View full abstractDownload PDF (551K) -
Shigeru ITO, Kentaro YAMAGUCHI, Yasuo KOMODA1992 Volume 40 Issue 12 Pages 3327-3329
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of the dinitrated product from the reaction of the 1(2H)-phthalazinone (1a) with acetyl nitrate was confirmed definitively by X-ray crystallography. The structure (1d) proposed previously was revised as 2-nitro-1(2H)-phthalazinone (1c).View full abstractDownload PDF (585K) -
Baoliang CUI, Junko INOUE, Takashi TAKESHITA, Junei KINJO, Toshihiro N ...1992 Volume 40 Issue 12 Pages 3330-3333
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the seeds of Astragalus sinicus L. (Leguminosae), seven triterpene glycosides were isolated and identified as soyasaponin I-III methyl esters (1-3) which were treated with CH2N2 during the separation procedure, soyasaponin IV (4), soyasapogenol B 3-O-β-D-glucuronopyranoside (5), 3-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranostyl(1→2)-β-D-glucuronopyranosyl 3β, 22β, 24-trihydroxy-11-oxoolean-12-ene (6), whose sapogenol (8) was obtained by enzymatic hydrolysis using glycyrrhizinic acid hydrolase, unambiguously characterized and designated as complogenin, and 3-O-α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl complogenin (7).View full abstractDownload PDF (661K) -
Daikichi HORIGUCHI, Yoshiki KATAYAMA, Kazumi SASAMOTO, Hideyuki TERASA ...1992 Volume 40 Issue 12 Pages 3334-3337
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new macrocyclic ligand for Eu3+, 24, 30-diphenyl-8, 19-(1, 21 : 4, 6 : 10, 12 : 15, 17-tetraetheno-8, 9, 19, 20-tetrahydro-7H, 18H-dibenzo[b, k][1, 4, 7, 10, 13, 16]hexaazacyclooctadecine)diacetic acid (1), was synthesized and its fluorescence characteristics were examined, particulary to compare with 4, 7-bis(chlorosulfophenyl)-1, 10-phenanthroline-2, 9-dicarboxylic acid (BCPDA) that has proved to be useful as a label in time-resolved fluoroimmunoassays. The complex of macrocycle 1 with Eu3+ was found to have a higher fluorescence intensity as well as a longer fluorescence lifetime than that of BCPDA.View full abstractDownload PDF (678K) -
Nobuyuki KOGA, Ayako SHIN'YAMA, Chuzo ISHIDA, Nobumitsu HANIOKA, Hidet ...1992 Volume 40 Issue 12 Pages 3338-3339
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMetabolism in vivo of 2, 4, 3', 4'-tetrachlorobiphenyl (TCB) was further studied using male Wistar rats. When the extract of feces of rats given TCB with chloroform was methylated and applied to gas chromatography (GC)-mass spectrometry (MS), a new metabolite was detected. The structure of this new metabplite was 4-hydroxy-2, 5, 3', 4'-TCB based on both its retention time in GC and comparison of the mass spectrum with that o the synthetic sample. 4-Hydroxy-2, 5, 3', 4'-TCB was assumed to be formed via a 4, 5-oxide intermediate followed by NIH-shift of a chlorine atom at 4-position.View full abstractDownload PDF (410K) -
Kazumi DANJO, Yasuhiko MIYAGAWA, Yukio KITAMURA, Akinobu OTSUKA1992 Volume 40 Issue 12 Pages 3340-3342
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn vitro release tests were investigated in single-layered and double-layered film systems. Sodium guaiazurene-3-sulfonate (GAS) was chosen as the drug for local use. Hydroxypropylcellulose (HPC), hydroxypropylmethyl-cellulose phthalate (HPMCP) and polyvinylacetaldiethylaminoacetate (AEA) were used to make films, and the tests were done with films made of various ratios of these two polymers.The drug rekease from the HPC single-layered films was independent of pH, and showed a zero order release. The apparent release rate constants, ka of the double-layered film varied according to the nature of the polymers and the drug as well as with the pH of the testing solutions.The results suggest the possibility of sustained release from double-layered films.View full abstractDownload PDF (484K) -
Keiko SUGITO, Hiroyasu OGATA, Hajime GOTO, Nahoko KANIWA, Hideo TAKAHA ...1992 Volume 40 Issue 12 Pages 3343-3345
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe gastric emptying rates of three enteric micro-capsule preparations with mean diameters of 1.1 mm and less (1.1, 0.5 and 0.1 mm) were compared. The gastric emptying rate was evaluated by determining the pharmacokinetic parameters of pyridoxic acid, including Vmax (peak excretion rate) and Tmax (time to reach peak excretion rate) after oral administration of micro-capsules containing pyridoxal phosphate as a marker drug to five healthy subjects. When given under fasting conditions, the gastric emptying rates of these prepartions, according to Tmax, differed significantly; the preparations with smaller particle sizes were emptied from the stomach at a faster rate than those with larger particle sizes. However, under non-fasting conditions the gastric emptying rates were virtually the same, regardless of particle size, and all the preparations were emptied from the stomach at a much slower rate than when administered under fasting conditions.View full abstractDownload PDF (619K) -
Makoto OTSUKA, Yoshihisa MATSUDA, Tadashi KOKUBO, Satoru YOSHIHARA, Ta ...1992 Volume 40 Issue 12 Pages 3346-3348
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel device containing cephalexin as a model drug using a self-setting bioactive cement basing on CaOSiO2-P2O5 glass was investigated. Glass powders contained 5% cephalexin powder hardened within 5 min after being mixed with a phosphate buffer. After hardening, in vitro drug release from homogeneous or heterogeneous drug-loaded cement pellets in a simulated body fluid at pH 7.25 and 37°C continued for more than 2 weeks.View full abstractDownload PDF (395K) -
Naoki HAGA, Tomohiko OHWADA, Iwao OKAMOTO, Koichi SHUDO1992 Volume 40 Issue 12 Pages 3349-3351
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEpoxidation and dihydroxylation of the olefin moiety of 2-substituted dibenzobicyclo[2.2.2] octatrienes were investigated. These reactions exhibited substituent effect : 2-nitodibenzo bicyclo[2.2.2]octatriene gave predominantly the syn-epoxide and the syn-diol, with a diastereomeric excess of 54% to 76%. respectively. On the other hand, the 2-methoxy substrate showed only a small preference in the reactions, giving a slight excess of the antiproducts. This effect can be interpreted in terms of the perturbation of the occupied π orbital of the ethylene moiety arising from the mixing of the π orbitals (in particular, the HOMO) of convex-substituted dihydroxyanthracene, wherein the σ type overlaps are involved in a manner similar to the longicyclic conjugation.View full abstractDownload PDF (505K) -
Masayuki TOSHIKAWA, Emiko UCHIDA, Nobuyasu CHATANI, Hiromi KOBAYASHI, ...1992 Volume 40 Issue 12 Pages 3352-3354
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew antiallergic and antimicrobial dihydroisocoumarins, thunberginols C, D, and E, were isolated from Hydrangeae Dulcis Folium, the fermented and dried leves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, together with new dihydroisocoumarin glycosides, thunberginol G 3'-O-glucoside and (-)-hydrangenol 4'-O-glucoside. Their chemical structures have been determined on the basis of chemical and physicochemical evidence. Thunberginols C, D, E, G, and (-)-hydrangenol 4'-O-glucoside showed antiallergic activity in the in vitro bioassay using the Schults-Dale reaction in sensitized guinea pig bronchial muscle, and they also exhibited antimicrobial activity against oral bacteria.View full abstractDownload PDF (562K) -
Meselhy R. MESELHY, Shigetoshi KADOTA, Yasunori MOMOSE, Masao HATTORI, ...1992 Volume 40 Issue 12 Pages 3355-3357
Published: December 25, 1992
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTinctormine (1a), N-containing quinochalcone glycoside, has been isolated from safflower and its structure has been determined by means of 2-D NMR spectroscopy including HMBC; 1a was proved to be a potent Ca2+ antagonist.View full abstractDownload PDF (513K)
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