All issues
Volume 39, Issue 10
Displaying 1-50 of 67 articles from this issue
-
Tokihiro NIIYA, Miho YUKAWA, Hiroki MORISHITA, Hirohito IKEDA, Yoshino ...1991 Volume 39 Issue 10 Pages 2475-2482
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present report describes sudies on the reaction mechanisms of an α-proton abstraction from acetone (MMK), methyl ethyl ketone (MEK), methyl isopropyl ketone (MIPK) and methyl tert-butyl ketone (MTBK) using CH3ONa in CH3OD solution. The activation energies for the deuterium exchange reaction of active methyl group of the ketones MMK, MEK, MIPK and MTBK were 11.87, 12.14, 12.29 and 13.14 kcal·mol-1, respectively. The deprotonation reaction mechanisms of the methyl alkyl ketones with methoxide anion were studied by ab initio molecular orbital method. Optimized geometries and energies of all complexes consisting of two molecules were calculated by 6-31+G basis set. The correlation between the activation energies and the differences in calculated energies of the transition state (ETS) and the H-bonded encounter complex I (E1) was fairly good. It is shown that the mechanisms of the deprotonation reactions can be explained with a simple model consisting of a methyl alkyl ketone and a methoxide anion.View full abstractDownload PDF (1059K) -
Hiromi IYO, Hitoshi UEDA, Yoshihide USAMI, Yayoi KAFUKU, Mitsunobu DOI ...1991 Volume 39 Issue 10 Pages 2483-2486
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a model study to investigate the sequence dependence of a peptide for the interaction with nucleic acid base, four kinds of tryptophan-containing dipeptides [Trp-Glu, Glu-Trp, Trp-Gly and Gly-Trp] were synthesized, and their abilities in forming the complexes with guanine base were examined by fluorescence and proton nuclear magnetic resonance (1H-NMR) methods. The fluorescence titration of each dipeptide with 7-methylguanosine-5'-phosphate (m7GMP) indicated that although the stacking interaction dominates the binding in each peptide, the carboxyl side chain of Glu plays an additional role in the binding with the base. The effect of Glu residue and its sequence dependence for the interaction was more clearly demonstrated by the 1H-NMR titration. Since the association constants determined from the downfield shift of the guanine NH2 resonance exhibited the same tendency as those from the upfield shift of the guanine N7-methyl protons [Trp-Glu > Trp-Gly >Glu-Trp > Gly-Trp], the close cooperation between the hydrogen bond and stacking interactions was suggested to be important for the tight binding of the peptides to the guanine base. Further, it was suggested that the peptide which contains an aromatic amino acid at the N-terminal side and an acidic one at the C-terminal side has an advantage in forming such a complex.View full abstractDownload PDF (724K) -
Yayoi KAFUKU, Yukari MATSUI, Junko OHTANI, Yoshihide USAMI, Hitoshi UE ...1991 Volume 39 Issue 10 Pages 2487-2490
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of a series of peptides designed to have binding ability selective for each of the nucleic acid bases, five tripeptides consisting of N-acetyl-Trp-X-Trp-NHCH3 (X=Gly, Asn, Asp, Gln and Glu) were synthesized, and their abilities to from complexes with four different nucleotides were examined by the fluorescence and phase distribution methods. The association constants obtained indicated that, depending on the sort of X residue, the peptides showed a variation in their interaction with guanosine monophosphate (GMP), while no noticeable selectivity was observed for other nucleotides adenosine monophosphate (AMP), uridine monophosphate (UMP) and cytidine monophosphate (CMP). The binding mode of N-acetyl-Trp-Asp-Trp-NHCH3 for the guanine base was further investigated using the proton nuclear magnetic resonance (1H-NMR) method. The mode was suggested to involve intimate cooperation of (1) the hydrogen bond formation between the carboxyl group of the Asp side chain and the guanine C2-amino group, and (2) the stacking interaction of the base with two terminal Trp residues of the peptide. Such interaction was strengthened by the protonation of the guanine base. A tentative binding mode is proposed based no these results.View full abstractDownload PDF (720K) -
Hiroaki TAKAYANAGI, Yuko TOUBAI, Motoaki GOTO, Shin-ichi YAMAGUCHI, Ha ...1991 Volume 39 Issue 10 Pages 2491-2493
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe crystal structure of the benzene : picric acid complex has been elucidated by X-ray crystal analysis. Benzene and picric acid molecules are stacked alternately along the a-axis, making their molecular planes parallel to each other. Two crystallographically independent benzene : picric acid complexes exist in an asymmetric unit.View full abstractDownload PDF (556K) -
Tatsuya TAKAGI, Tomoko KATAYAMA, Mika TANI, Ryodo TOKURA, Akihiro NODA ...1991 Volume 39 Issue 10 Pages 2494-2497
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe substituent constants for sigma-inductive effect, called iota of σx, were reproduced by calculation using the Takano-Hosoya-Iwata electron number (THIEN). The differences in electron numbers at a distance of R from a central atom were most effective in reproducing the sigma-inductive subsituent constants, when R was set equal to 132.5 pm. On the other hand, averaged molecular electrostatic potentials reproduced well the substituent constants for electronic field effects, called σI or σF. These results indicate that the electronic substituent constants can be determined nonempirically by calculation based on quantum chemistry.View full abstractDownload PDF (667K) -
Masahiro KATO, Kazuo SASAHARA, Kiyoshige OCHI, Hiroyuki AKITA, Takeshi ...1991 Volume 39 Issue 10 Pages 2498-2501
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(±)-N-Isonicotinoyl-2-amino-5-chlorobenzhydrol (1) is a rice plant growth regulator which shortens the second leaf sheaths. One of the enantiomers, (S)-1, was obtained by microbiological asymmetric reduction of 2-amino-5-chlorobenzophenone using Rhodosporidium toruloides followed by isonicotinoylation. Several substituted benzhydrol derivatives were also prepared by use of the same biological method and converted to N-isonicotinoyl compounds. The growth-regulating activities of these compounds were evaluated.View full abstractDownload PDF (597K) -
Kunio HIGASHI, Kiyoshi NAKAYAMA, Emiko SHIOYA, Tsuneo KUSAMA1991 Volume 39 Issue 10 Pages 2502-2504
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel direct transformation of O-glycoside into glycosyl bromide by using trimethylsilyl bromide and zinc bromide has been developed. Treatment of various glycosides (3a-5a, 10, 12 and 14) with trimethylsilyl bromide and zinc bromide in dichloromethane afforded the glycosyl bromides (6, 11, 13 and 15) in 53, 85, 94, 47, 41 and 40% yields, respectively.View full abstractDownload PDF (609K) -
Hatsuo YAMAMURA, Kahee FUJITA1991 Volume 39 Issue 10 Pages 2505-2508
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHeptakis(6-O-(p-tosyl))-β-cyclodextrin and heptakis(6-O-(p-tosyl))-2-O-(p-tosyl)-β-cyclodextrin were prepared by the reaction of β-cyclodextrin with p-tosyl chloride in pyridine. They were converted to heptakis(3, 6-anhydro)-β-cyclodextrin, constituted from alternative (1C4) glucose units.View full abstractDownload PDF (585K) -
Chihiro ITO, Kazuko FUJIWARA, Mayumi KAJITA, Motoharu JU-ICHI, Yuko TA ...1991 Volume 39 Issue 10 Pages 2509-2513
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new coumarins, named peroxytamarin (1), cis-casegravol (5), citrusarin-A (7), and citrusarin-B (8), were isolated from root of Citrus plants and their structures were elucidated by chemical and spectrometric methods. Citrusarin-B (8), a coumarin having both a dimethylpyran ring and a dihydrofuran ring in the molecule, was also synthesized.View full abstractDownload PDF (940K) -
Kiyoshi NISHITANI, Kanou HARADA, Noboru SANO, Koji SATO, Koji YAMAKAWA1991 Volume 39 Issue 10 Pages 2514-2524
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA stereoselective synthesis of a dihydrofuran derivative (5) and an allylhalide (8), possible precursors of the cembranes (-)-sarcophytonin A and (-)-sarcophytoxide, is described. The optically active dihydrofuran, right half, segment (49) was synthesized starting from a naturally occurring monoterpene, (-)-carvone. It was converted into the phenylselenide (14) via three steps. Oxidation of 14 with m-chloroperbenzoic acid and then treatment with pyridine yielded the epoxy olefin (29). Cleavage of the epoxide with boron trifluoride etherate gave the methoxy alcohol (31). Bromoetherification with N-bromosuccinimide selectively yielded the cis-hexahydro-1-oxaindan derivative (36) having a new chirality at the C-6 position. Reductive debromination of 36 followed by oxidation and then enol silylation yielded the less substituted silyl enol ether (39). Ozonolysis of 39 followed by methylation and elimination of methanol with potassium tert-butoxide and then reduction with 9-borabicyclo[3.3.1]nonane (9-BBN) gave the dihydrofuran derivative (41). Protection as the silyl ether (42) and phenylselenenylation and then treatment with hydrogen peroxide yielded the unsaturated ester (45). Reduction followed by thiophenylation of the resulting hydroxyl group afforded the dihydrofuran derivative (49) as a right half segment. Left half segments, the chloride (53) and the bromide (54), were synthesized starting from geraniol via several steps.View full abstractDownload PDF (1888K) -
Chihiro ITO, Mayumi NAKAGAWA, Tian-Sheng WU, Hiroshi FURUKAWA1991 Volume 39 Issue 10 Pages 2525-2528
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a further study of the constituents of stem bark of Murraya euchrestifolia HAYATA collected in Taiwan, five new monomeric carbazoles named murrayaline-B (1), -C (2) and -D (3), pyrayafoline-E (5) and euchrestine-E (7), one carbazolequinone named murrayaquinone-E (9), and two dimeric carbazoles named bismurrayafoline-C (11) and -D (12) were isolated along with known carbazoles. The structures of new alkaloids were elucidated by spectrometric and/or chemical methods. The new monomeric carbazoles were found to have 2-oxygenated 3-C-substituted carbazole nuclei and the new dimeric carbazoles to have symmetrical structures containing a 1-oxygenated 3-methylcarbazole skeleton.View full abstractDownload PDF (755K) -
Tsutomu NAKANISHI, Mari KONISHI, Hiroko MURATA, Akira INADA, Atsushi F ...1991 Volume 39 Issue 10 Pages 2529-2533
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new ionone glucosides, melia-ionosides A and B, were isolated from leaves of Melia toosendan SIEB. et ZUCC. (Meliaceae) and their structures were elucidated based on combinations of chemical, spectral, and X-ray analytical studies. In addition, a novel type of selective bio-oxidation by a kind of protease (Molsin) was found during the course of the structural elucidation.View full abstractDownload PDF (864K) -
Masateru ONO, Toshio KAWASAKI, Kazumoto MIYAHARA1991 Volume 39 Issue 10 Pages 2534-2539
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTen ether-soluble resin glycosides (jalapins), operculins IX-XVIII, were isolated from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Operculins III and IV previously obtained, and operculins IX, X, XVI, XVII and XVIII were characterized on the bases of chemical and spectral data. All of them have a common glycosidic acid, operculinic acid B, with a macrocyclic ester structure and n-decanoyl and/or n-dodecanoyl residues as organic acid groups.View full abstractDownload PDF (845K) -
Yasuo OHTSUKA, Fumitaka ITOH, Takeshi OISHI1991 Volume 39 Issue 10 Pages 2540-2544
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA stereocontrolled total synthesis of natural (+)-cis-α-irone (1) is described. The key intermediate (±)-hemiacetal 15 was prepared from the diene 10 in six steps. The crucial optical resolution of (±)-15 was achieved by initial stereoselective conversion into the corresponding l-menthyl acetals 16 and 17 followed by separation and hydrolysis. One of the optically pure enantiomers of 15 was transformed to (-)-18 and then to (+)-1 in seven steps. The synthetic (+)-1 was found to be identical with the natural (+)-cia-α-irone. The isomeric (-)-cis-α-irone was also synthesized from the other enantiomer of 15, via (+)-18.View full abstractDownload PDF (833K) -
Hiroshi IRIE, Takao KITAGAWA, Masaaki MIYASHITA, Yong ZHANG1991 Volume 39 Issue 10 Pages 2545-2549
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethyl esters of AF-toxin IIa and IIc, toxic compounds to Japanese white pear produced by Alternaria alternata strawberry pathotype, were synthesized as the optically active forms starting from vitamin C as a chiral material.View full abstractDownload PDF (940K) -
Yuko KOBAYASHI, Teruyo MATSUMOTO, Yoshiji TAKEMOTO, Kazuhiko NAKATANI, ...1991 Volume 39 Issue 10 Pages 2550-2555
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe addition reaction of cyclohexylmethylmagnesium bromide with the imine prepared from unnatural(2S, 3S)-tartaric acid was found to proceed in a highly stereoselective manner in the presence of cerium(III) chloride. A chelation-controlled mechanism could explain the stereochemical outcome of the addition reaction. The addition product could be elaborated into three types of C-terminal components of renin inhibitors by employing oxidative cleavage of the 1, 2-diol moiety, epoxide formation with inversion of configuration, and epoxide opening with a nucleophile.View full abstractDownload PDF (1149K) -
Tohru NAKAO, Minoru OBATA, Minoru KAWAKAMI, Kenji MORITA, Hiroshi TANA ...1991 Volume 39 Issue 10 Pages 2556-2563
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 2-aryl-5, 6-dihydro-(1)benzothiepino[5, 4-c]pyridazin-3(2H)-ones and related compounds were synthesized and evaluated for their ability to displace 3H-diazepam from rat brain membranes in vitro, and to prevent bicuculline induced convulsions in mice in vivo.Compounds with a 4'-methoxyphenyl (36) or 4'-chlorophenyl group (37, 39-42) as 2-aryl substituents showed prominent activities in both the in vitro and in vivo tests. Among them, 2-(4'-chlorophenyl)-5, 6-dihydro- (37) and 2-(4'-chlorophenyl)-5, 6-dihydro-10-fluoro-(1)benzothiepino[5, 4-c]pyridazin-3(2H)-one 7-oxides (41) showed activity twice as potent as diazepam in an anticonflict test (Vogel type, rats) while exhibiting less muscle relaxation (rotarod test, mice) and augmentation of γ-aminobutyric acid-induced chloride current (1cl) in isolated frog sensory neurones than diazepam. Compound 37 (Y-23684) was selected from this series as a candidate for further development. The structure-activity relationships are discussed.View full abstractDownload PDF (1110K) -
Mikio KUROKAWA, Fuminori SATO, Yoshinobu MASUDA, Takayuki YOSHIDA, Yuk ...1991 Volume 39 Issue 10 Pages 2564-2573
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 11-[4-(cinnamyl)-1-piperazinyl]-6, 11-dihydrodibenz[b, e]oxepins and related compounds were synthesized and evaluated for their protective activities against complete ischemia, normobaric hypoxia, lipidperoxidation and convulsion. Structure-activity relationship studies of this series led to the finding of (E)-1-(3-fluoro-6, 11-dihydrodibenz[b, e]oxepin-11-yl)-4-(3-phenyl-2-propenyl)piperazine dimaleate (50), AJ-3941 with the most appropriate property for combined pharmacological activities.View full abstractDownload PDF (1280K) -
Seigo SAWADA, Ken-ichiro NOKATA, Tomio FURATA, Teruo YOKOKURA, Tadashi ...1991 Volume 39 Issue 10 Pages 2574-2580
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA radical substitution reaction of 20(S)-camptothecin (1) with methanol furnished 7-hydroxymethylcamptothecin (2). Reaction of 1 with primary alcohols higher than methanol gave 7-alkylcamptothecins (4), of which alkyl groups were one carbon less than the alcohols used and also 7-hydroxyalkylcamptothecins (5). For the preparation of 7-alkylcamptothecin (4), aldehydes were used as a radical source and several alkylated derivatives were synthesized. 7-Acyloxymethyl derivatives (6), 7-carbaldehyde (7), iminomethyl derivatives (10), acid (11), esters (12) and amides (13) were synthesized starting from 2. 7-Ethyl-(4b) and 7-propylcamptothecin (4c), acyloxymethyl compounds 6a, 6c and ethyl ester (12b) exhibited higher antitumor activity than 1 against L1210 in mice.View full abstractDownload PDF (1213K) -
Toshiyuki KONOSU, Yawara TAJIMA, Noriko TAKEDA, Takeo MIYAOKA, Mayumi ...1991 Volume 39 Issue 10 Pages 2581-2589
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew triazole compounds were designed and synthesized as potential inhibitors of the fungal cytochrome P-450 14α-demethylase. In testing for antifungal activity against a mouse systemic Candida albicans infection, (2R, 3R)-3-acylamino-2-aroyl-2-butanol derivatives III exhibited remarkably high efficacy after oral or parenteral administration. The structure-activity relationships of these amidoalcohols were evaluated.View full abstractDownload PDF (1269K) -
Muneaki KURIMURA, Masumi TAKEMATO, Kazuo ACHIWA1991 Volume 39 Issue 10 Pages 2590-2596
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of optically active lipopeptide derivatives has been accomplished by the use of chiral glycerol derivatives. Lipopeptide derivatives with (R)-glycerol moieties showed higher mitogenic activities than those with the (S)-configuration. N-2, 2, 2-Trichloroethoxycarbonyl lipopeptide derivatives increased mitogenic activity.View full abstractDownload PDF (1132K) -
Makoto KOSHIGAMI, Kazuhito WATANABE, Toshiyuki KAMURA, Ikuo YAMAMOTO1991 Volume 39 Issue 10 Pages 2597-2599
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCentral depressant effects in mice of N3-substituted 6-azauridines (6-AzUd) (1) were examined by intracerebroventricular (i.c.v) injection. Eleven derivatives including alkyl-, benzyl-, xylyl- and phenylethly-substitution onto the N3-position of 1 were synthesized and their pharmacological effects were evaluated using hypnotic activity, locomotor activity, motor incoordination and pentobarbital-induced sleep prolongation as indices. Six of 12 compounds showed the hypnotic activity. At a dose of 2 μmol/mouse, the mean sleeping time induced by 1, N3-benzyl-6-AzUd (7), N3-o-xylyl-6-AzUd (8), N3-m-xylyl-6-AzUd (9), N3-p-xylyl-6-AzUd (10) and N3-α-phenylethyl-6-AzUd (11) was 14, 11, 45, 12, 9 and 16 min, respectively. These derivatives and N3-β-phenylethyl-6-AzUd (12)(1.5 μmol/mouse) significantly prolonged pentobarbital-induced (40 mg/kg, i.p.) sleeping time, whereas none of the N3-alkylated derivatives (methyl-, ethyl-, n-propyl-, n-butyl- and allyl-substitution) exetred the hypnotic activity or pentobarbital-induced sleep prolongation. Nucleoside 1 and its xylyl-derivatives (1.5 μmol/mouse) singificantly decreased locomotor activity of mice, their effects paralleled the hypnotic activity. These compounds (1.5 μmol/mouse) also produced motor incoordination and potentiated the effect of diazepam-induced motor incoordination. These results indicate that 1 and its benzyl-related derivatives, but not alkyl-derivatives have a depressant effect on the central norvous system.View full abstractDownload PDF (532K) -
Yukinobu IKEYA, Ko SUGAMA, Minoru OKADA, Hiroshi MITSUHASHI1991 Volume 39 Issue 10 Pages 2600-2605
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new phenolic glycosides, tenuifolisides A (1), B (2), C (3), and D (4) together with a known phenolic glyciside, β-D-(3-O-sinapoyl)-fructofuranosyl-α-D-(6-O-sinapoyl)-glucopyranoside (5) were isolated from the roots of Polygala tenuifolia. The structures of these new compounds were characterized as β-D-(3-O-(3, 4, 5-trimethoxycinnamoyl)]-fructofuranosyl-α-D-[6-O-(p-hydroxybenzoyl)]-glucopyranoside (1), β-D-(3-O-sinapoyl)-fructofuranosyl-α-D-(6-O-[p-hydroxybenzoyl)]-glucopyranoside (2), β-D-[3-O-(3, 4, 5-trimethoxycinnamoryl)]-fructofuranosyl-α-D-(6-O-sinapoyl)-glucopyranoside (3), and 1, 5-anhydro-[6-O(3, 4, 5-trimethoxycinnamoryl)]-D-glucitol (4), respectively, on the basis of chemical and spectral evidence including two dimensional unclear magnetic resonance (2D-NMR) studies.View full abstractDownload PDF (918K) -
Isao KOUNO, Takuya MORISAKI, Yumiko HARA, Chun-Shu YANG1991 Volume 39 Issue 10 Pages 2606-2608
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new sesquineolignans, named dunnianol (1) and isodunnianol (2), respectively, were isolated from the bark of Illicium dunnianum together with the known biphenylneolignan, magnolol (3). Compounds 1 and 2 have a similar triphenyl-type neolignan structure to that of macranthol (4), which we previously isolated from the pericarps of I. macranthum. Their structures were elucidated by means of the detailed analysis of their 1H-and 13C-nuclear magnetic resonance spectra of 1, 2, and their acetylation and methylation products, including two-dimensional NMR spectra, comparing with those of magnolol, isomagnolol and macranthol.View full abstractDownload PDF (572K) -
Hiroshi KOHDA, Seiji TANAKA, Yasutoshi YAMAOKA, Yoshie OHHARA1991 Volume 39 Issue 10 Pages 2609-2612
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour triterpenoid saponins were isolated from Amaranthus hypochondriacus which are grain crops in the Nepal, Mexico and South America. Their structures were elucidated based on spectral evidence to be : (1) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester. (2) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxyolean-12-en-23-al-28-oic acid 28-O-β-D-glucopyranosyl ester; (3) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxy-30-norolean-12, 20(29)-dien-28-oic acid 28-O-β-D-glucopyranosyl ester. (4) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxy-30-norolean-12, 20(29)-dien-23-al-28-oic acid 28-O-β-D-glucopyranosyl ester.View full abstractDownload PDF (675K) -
Yan-Nong SONG, Masaaki SHIBUYA, Yutaka EBIZUKA, Ushio SANKAWA1991 Volume 39 Issue 10 Pages 2613-2616
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVirulence (vir) gene expression of Agrobacterium tumefaciens is activated by plant phenolic compounds such as α-hydroxyacetosyringone (HOAS), acetosyringopone (AS), methyl syringate, coniferyl alcohol and sinapyl alcohol.Inositol was found to be a potentiating factor of vir-inducing activity, which enhanced the vir-inducing activity of AS and HOAS in a synergistic manner, in particular at a low concentration of AS and HOAS. Of the other sugars tested D-gluose, L-rhamnose, D-xylose and D-galacturonic acid, the main components of plant cell wall polysaccharides, remarkedly potentiated the vir-inducing activity of AS, indicating the cooperative action of the signal compunds and sugars in Agrobacterium infection to plants.View full abstractDownload PDF (807K) -
Hideo YOSHIZAKI, Yohichi HASHIMOTO, Koichi ARAI, Masao OHKUCHI, Masami ...1991 Volume 39 Issue 10 Pages 2617-2621
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCalphobindin-II (CPB-II, annexin VI), is a calcium dependent phospholipid binding protein that can be classified as a member of the annexin family.The phospholipid-binding properties of CPB-II were investigated by measuring the binding constants of [125I]-CPB-II using phospholipid vesicles consisting of 80% phosphatidylcholine and 20% phosphatidylserine. A dissociation constant (Kd) of CPB-II with the phospholipid vesicles was determined to be 0.2 to 0.3 nM in the presence of Ca2+ ranging from 0.3 to 30 mM. The number of CPB-II capable of binding to the phospholipid vesicles at 0.3 mM Ca2+ decreased to about 1/2 in the presence of Ca2+ of more than 1 mM. Prothrombin and factor X were effective in competing with the binding of CPB-II to the phospholipid vesicles, although their affinities were lower by two or three orders of magnitude than that of unlabeled CPB-II at 30 mM Ca2+. Competitive effects of CPB-II, calphobindin-I(CPB-I, annexin V) and calphobindin-III (CPB-III, annexin III) on binding of [125I]-CPB-II to phospholipid vesicles, were similarly observed.View full abstractDownload PDF (779K) -
Toshihiro FUJII1991 Volume 39 Issue 10 Pages 2622-2626
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn actin-binding protein (p33) has been purified from chicken gizzard smooth muscle. The homogenous protein has a molecular weight near 33000 as determined by both sodium dodecyl sulfate-polyacrylamide gel electrophoresis(SDS-PAGE) and size exclusion chromatography. Its binding ability to F-actin remained after heating at 95°C for 4 min. Immunoblot analyses indicated that p33 was not a degradation product from higher molecular components. The binding of p33 to F-actin was saturable in a molar ratio of about one p33 to 2-3 actin molecules with an apparent binding constant of 6.6×107 M-1. p33 also bound to calmodulin and tropomyosin. The bindings of p33 to F-actin and tropomyosin were regulated by calmodulin in a Ca2+-dependent fashion. In addition to actin, caldesmon and tropomyosin, p33 was contained in the native thin filaments prepared from smooth muscle. Other actin-binding proteins, including α-actinin, caldesmon and filamin, had little effect on p33 binding to actin filaments. These results demonstrate that p33 may function in actin-based cellular processes which are mediated by Ca2+ and calmodulin.View full abstractDownload PDF (1146K) -
Taiko ODA, Yoshihiro SATO, Shigetaka KITAJIMA, Yukio YASUKOCHI1991 Volume 39 Issue 10 Pages 2627-2629
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe examined the effects of diethylstilbestrol (1), Z, Z-dienestrol (2), E, E-dienestrol (3), indenestrol A (4), indenestrol B (5) and estradiol (6) on the activity of in vitro accurate transcription from adenovirus 2 major late promoter by mammalian ribonucleic acid (RNA) polymerase II using partially purified transcription factors from HeLa cell nuclear extract as well as on RNA polymerase II activity assayed for random incorporation of ribonucleotides. 1, 2, and 3 inhibited both activities, whereas 4 and 5 were inhibitory only in the transcription activity at concentrations higher than 10 μg/ml. However 6 had no effects on both activities.View full abstractDownload PDF (586K) -
Noriko SHIMIZU, Hatsuki ASAHARA, Masashi TOMODA, Ryoko GONDA, Naoko OH ...1991 Volume 39 Issue 10 Pages 2630-2632
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structural features of MVS-I, the major neutral polysaccharide isolated from the seeds of Malva verticillata L., were elucidated by controlled Smith degradation, methylation analysis, partial acid hydrolysis and enzymic degradation studies. It has a backbone chain composed of β-1, 3-linked D-glucose and D-galactose residues having branches composed of α-1, 5-linked L-arabinosyl β-1, 4-linked D-galactose and of β-1, 4-linked D-galactosyl β-1, 3-linked D-glucose residues at position 6 of a part of D-halactose units as side chains. MVS-I showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test.View full abstractDownload PDF (659K) -
Hiroko SHIMADA, Norio INOKUCHI, Takashi KOYAMA, Masachika IRIE1991 Volume 39 Issue 10 Pages 2633-2637
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn endonuclease with 3'-nucleotidase activity (nuclease Le1) was purified from fruit bodies of Lentinus edodes in a single band on sodium dodecylsulfate-polyacrylamide gel electrophorosis (SDS-PAGE). The apparent molecular weight of nuclease Le1 was about 27000. The nuclease was inactivated in the presence of ethylenediaminetetraacetic acid (EDTA) and reactivated by the addition of Zn2+. Hydrolysis of poly U by the nuclease showed many intermediate size oligomers prior to the formation of 5'-uridine monophosphate (UMP). Therefore, it was concluded that nuclease Le1 was a Zn2+-endonuclease similar to P1-nuclease from Penicillium citrinum. The nuclease was very sensitive to ionic strength, but pH-profiles of the hydrolysis of four 3'-nucleotides were very similar to those of P1 nuclease from P. citrinum.View full abstractDownload PDF (762K) -
Motoaki KOIZUMI, Teruaki AKAO, Shigetoshi KADOTA, Tohru KIKUCHI, Takuo ...1991 Volume 39 Issue 10 Pages 2638-2643
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThis report discusses a novel type of arylsultotransferase (AST) which was derived from human intestinal bacterium sulfated polyphenolic compounds when p-nitrophenyl sulfate (PNS) was taken as a donor substrate. (+)-Catechin, (±)-catechin, (-)-epicatechin and (-)-epicatechin gallate were better substrates than tyramine. (-)-Epigallocatechin and (-)-epigallocatechin gallate were slightly worse substrates than tyramine. Although gallic acid was a bad substrate, alkyl gallate esters were better substrates than tyramine. The degree of acceptor specificity increased in proportion to the length of the alkyl group up to the carbon number of five. Pedunculagin, geraniin and corilagin were less effective than tyramine. Rosmarinic acid and penta-O-galloyl-β-D-glucose were similarly well sulfated. Two products, 4'-monosulfate and 4', 5-disulfate of (+)-catechin, were detected at a two-fold molar excess of PNS over (+)-catechin. When (+)-catechin-4'-monosulfate as an acceptor was enzumatically sulfated with PNS as a donor, only the 4', 5-disulfate was produced. Thus, arylsulfotransferase was useful for the convenient preparation of sulfate esters of polyphenols at their specific hydroxyl groups.View full abstractDownload PDF (840K) -
Yasuo KOTERA, Yoshimasa INOUE, Masami OHASHI, Keizo ITO, Goro TSUKAMOT ...1991 Volume 39 Issue 10 Pages 2644-2646
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe antibacterial activity of a new tetracyclic quinolone, No. 5290, against 25 strains of Staphylococcus aureus clinically isolated in Japan in 1988-1989 was determined. The minimum inhibitory concentrations (MICs) of No. 5290 against both quinolone-susceptible (MIC : norfloxacin≃6.25 μg/ml, ciprofloxacin≤1.56 μg/ml) and 4 out of 5 norfloxacin- and ciprofloxacin-moderately resistant strains (MIC : 25 μg/ml≤norfloxacin≤50 μg/ml, 3.13 μg/ml, &l;ciprofloxacin≤12.5 μg/ml) were 0.05 μg/ml. Similar findings were obtained on the quinolone-resistant mutants derived by norfloxacin- or KB-5246-selection from quinolone -susceptible clinical isolates of S. auresu. The uptake of No. 5290 into a quinolone-susceptible strain of S. aureus was 2.47 μg/mg dry cell and the uptake in norfloxacin- and ciprofloxacin-moderately resistant strains was comparable to that in the quinolone-susceptible strain. The uptake of No. 5290 in both the quinolone-susceptible strain, and norfloxacin- and ciprofloxacin-moderately resistant, and No. 5290-susceptible strains was only slightly influenced by the treatment of bacteria with carbonyl cyanide m-chlorophenylhydrazone. These findings indicate that : (i) No. 5290 has potent antibacterial activity against quinolone-susceptible strains of S. aureus, and the potent activity might be due to a high uptake caused by an ineffective efflux of No. 5290. (ii) No. 5290 also has potent antibacterial activity against norfloxacin- and ciprofloxacin-moderately resistant strains, the reason for which could not be explained by the efflux.View full abstractDownload PDF (531K) -
Takashi ABIKO, Hiroshi SEKINO1991 Volume 39 Issue 10 Pages 2647-2652
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA fragment corresponding to N-terminal octaeicosapeptide of rat parathymosin α was synthesized by assembling 5 peptide fragments, followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole (molar ratio 1 : 1) in trifluoroacetic acid in the presence of dimethylselenium. Incubation of impaired T-lymphocytes isolated from uremic patients with the synthetic parathymosin α fragment 1-28 showed no immunological restoring effect, but when it was administered together with thymosin α1 it appeared to suppress the restoring effect of the thymosin α1 on the impaired T-lymphocytes of uremic patients.View full abstractDownload PDF (1057K) -
Keiko TANAKA, Tokuji TAKEDA, Kiyoko FUJII, Koichiro MIYAJIMA1991 Volume 39 Issue 10 Pages 2653-2656
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFactors such as lipid composition and liposome size, which affect the stability of liposomes during the freeze-drying process, were investigated. The addition of 9 mol% of charged lipids to egg-phosphatidylcholine (eggPC) had little effect on liposome stability. The addition of cholesterol decreased the retention percentage (R%) of entrapped calcein and increased the size of liposomes after freeze-drying. Destabilization occurred in the gel state of eggPC/cholesterol binary system. In liposome systems prepared using the extrusion technique, the R% decreased through freeze-drying as their size increased. Similar damage to liposomes was observed only by hyperosmotic shock : Considerable leakage occurred for large liposomes when the medium was changed from hyperosmotic to isotonic. Consequently, liposome leakage by freeze-drying likely occurs at the rehydration process.View full abstractDownload PDF (723K) -
Taro OGISO, Masahiro IWAKI, Yuji KASHITANI, Katsuaki YAMASHITA1991 Volume 39 Issue 10 Pages 2657-2661
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a previous paper, we have demonstrated that medium chain fatty acids significantly enhance the in vitro rectal absorption of propranolol (PL) and that the enhancement may be partly due to the formation of a complex with a fatty acid at a 1 : 1 molar ratio. To confirm in vivo the enhancement effect of lauric acid on PL absorption, PL suppositories with lauric acid at various molar ratios were administered at rat rectum. PL absorption from Witepsol and macrogol suppositroies with lauric acid at a 1 : 1 molar ratio was much larger than that after PL alone and the 1 : 2 or 1 : 3 molar ratio ones. The bioavailability (BA) after administration of the 1 : 1 molar ratio suppository (PL, 4 mg/kg) was 1.6- and 2.1-fold for the Witepsol and macrogol formulations respectively, compared with that after PL alone. A similar result was obtained with the PL solid dispersion suppository with lauric acid at a 1 : 1 molar ratio, showing a 1.7-fold higher BA compared with PL alone. The release of PL from the macrogol suppository was significantly faster at a 1 : 1 molar ratio than that of other preparations, but not so in the solid dispersion suppository. There was not good agreement between the release rates of PL from the suppositories and the plasma levels after dosing. These results supported the concept that a portion of PL, by forming a 1 : 1 complex with lauric acid, would penetrate across the rectal mucosa more easily than PL alone.View full abstractDownload PDF (803K) -
Keiichi ASAHARA, Hitoshi YAMADA, Shigeru YOSHIDA1991 Volume 39 Issue 10 Pages 2662-2666
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stabilities of human insulin (HI) is aqueous solutions were investigated in the pH range of 4.0-7.0 in the presence (1.0-3.0×10-3M) and absence of sodium bisulfite (SBS) both in the dark and under scattered light (1000 lux) using high performance liquid chromatography. Increasing concentrations of SBS tended to degrade HI. In the presence of SBS, with an increase in the pH value, the stability of HI decreased in the pH range of 4.0-7.0. There was a partial difference in the stability of HI in the presence of SBS in the dark and that under scattered light.HI was stabilized by glycose in the presence of SBS in the dark, and the stability of HI was revealed to depend on the concentration of free SBS. The reason for this phenomenon was postulated to be the formation of bisulfite-glucose adduct.View full abstractDownload PDF (799K) -
Makoto OTSUKA, Reiko TERAOKA, Yoshihisa MATSUDA1991 Volume 39 Issue 10 Pages 2667-2670
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe anhydrate and monohydrate of nitrofurantoin were characterized by X-ray diffraction analysis, infrared (IR) spectroscopy, thermal analysis and scanning electron microscopy. The X-ray diffraction patterns and the IR spectra of the anhydrate and monohydrate were significantly different, respectively. The differential thermal analysis (DTA) curve of the anhydrate showed endothermic and exothermic peaks at 272 and 276°C, respectively, with a loss of weight due to decomposition on the thermogravimetry curve. The DTA curve of the monohydrate showed an endothermic peak at 120-128°C with a loss of weight due to the dehydration of 1 mol/mol of crystal water, and endothermic and exothermic peaks at 273 and 276°C, respectively, accompanying decomposition. The initial dissolution rate of anhydrate and monohydrate in JP XI, 2nd fluid (pH 6.8) at 37°C were measured to estimate for solubility by using a rotating disk method. The solubilities of the anhydrate and monohydrate were estimated to be 47.8 and 27.4 mg/100 ml, respectively.View full abstractDownload PDF (836K) -
Narumi SUGIHARA, Koji FURUNO, Noriko KITA, Teruo MURAKAMI, Noboru YATA1991 Volume 39 Issue 10 Pages 2671-2673
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPlasma protein binding of weakly basic drugs such as propranolol and quinidine was determined in rats with carbon tetrachloride (CCl4)-induced hepatic disease. Free fractions of propranolol and quinidine in the plasma of rats at 24 h after CCl4-intoxication were decreased by 41 and 30%, respectively, compared to those of control rats. An addition of Tris (butoxyethyl) phosphate (TBEP), a specific displacer for basic drugs from α1-acid glycoprotein (AGP), to the plasma increased the free fractions of the basic drugs, resulting in no difference in the extent of the plasma free fraction of each drug between control and CCl4-intoxicated rats.Plasma concentration of AGP in CCl4-intoxicated rats was elevated 2.7-fold of that in control rats at 24h after the CCl4 intoxication and reached at peak of 4.8-fold evelation at 48h. A regression analysis revealed a high degree of positive correlation between ratios of bound to free fraction of propranolol and plasma concentrations of AGP. These results suggest that the plasma protein binding of the basic drugs was increased mainly due to the rise in the plasma AGP concentration in CCl4-intoxicated rats.View full abstractDownload PDF (625K) -
Hiroyuki WAKABAYASHI, Kenji SHIMADA, Tetsuo SATOH1991 Volume 39 Issue 10 Pages 2674-2676
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of diazepam (DZP) on melatonin synthesis in rat pineal gland was investigated in vivo. Subcutaneous injection of DZP (3 mg/kg) 1 h before the start of darkness significantly suppressed nocturnal elevations of pineal N-acetylserotonin (NAS) and melatonin contents in rats, and caused a 2-h delay in reaching the maximum melatonin level in the dark phase. DZP treatment also markedly suppressed the dark-induced increase of pineal N-acetyltransferase activity, which catalyzes the rate-limiting step in melatonin synthesis, but had no effect on hydroxyindole-O-methyltransferase activity, which catalyzes the final step of melatonin formation. Pineal norepinephrine and dopamine contents, in contrast, were not altered by DZP injection. The distribution rate of DZP to the brain reached the highest level 30 min after a single injection, while that to the pineal gland was observed 5 h later (i, e., 4h after the start of darkness). It is clear that the inhibitory effect of DZP on melatonin synthesis in rat pineal gland appears concomitantly with the increase in the distribution volume of DZP into this gland. These results suggest that the inhibitory effect of DZP on melatonin synthesis results from the drug's direct action on the rat pineal gland.View full abstractDownload PDF (626K) -
Hiroyuki WAKABAYASHI, Kenji SHIMADA, Tetsuo SATOH1991 Volume 39 Issue 10 Pages 2677-2680
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of propranolol (PPL), phenoxybenzamine (PBZ) or bicuculline (BCL) on the diazepam (DZP)-induced changes of pineal melatonin synthesis in male rats was examined in vivo and in vitro. Administration of PBZ did not affect the inhibitory action of DZP on pineal melatonin synthesis in vivo. A single injection of PPL inhibited the pineal melatonin synthesis similarly to the administration of DZP alone, but the two drugs together did not exhibit additive or synergistic effects on the melatonin synthesis. Significant decreases in the N-acetyltransferase (NAT) activity and the N-acetylserotonin (NAS) and melatonin contents were observed in the BCL-injected group, being greater than those in the DZP-treated group. Unexpectedly, however, the combination treatment of DZP and BCL caused an increase in the NAT activity and melatonin content compared with the BCL-alone group. Incubation with DZP at higher concentrations resulted in an increase of pineal NAT activity in vitro, but this increase was inhibited by preincubation with PPL, PBZ or BCL. DZP treatment thus appeared to have different effects on pineal NAT activity in vivo and in vitro. These results suggest that both a GABAergic mechanism and peripheral benzodiazepine (BZP) receptors in rat pineal gland may be involved in the modulation of melatonin synthesis by DZP.View full abstractDownload PDF (763K) -
Masayuki KITAGAWA, Kenjiro YAMAMOTO, Shinichi KATAKURA, Hideyuki KANNO ...1991 Volume 39 Issue 10 Pages 2681-2690
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDi- and tri-substituted [(4-oxo-4H-1-benzopyran-7-yl)oxy]acetic acids, and 4-oxo-3-phenyl-4H-furo[2, 3-h]-[1]benzopyran-8-carboxylic acid were synthesized and tested for natriuretic acid uricosuric activities. Among the compounds tested, 3, 5-disubstituted [(4-oxo-4H-1-benzopyran-7-yl)oxy]acetic acids (6c-f, h, n and x) showed potent natriuretic acid uricosuric activities, whereas 4-oxo-3-phenyl-4H-furo[2, 3-h][1]benzopyran-8-carboxylic acid (6dd) possessed only potent natriuretic activity. The structure-activity relationships are also discussed.View full abstractDownload PDF (1341K) -
Machiko MATSUURA, Hiroshi ZENDA, Shigetoshi CHIBA1991 Volume 39 Issue 10 Pages 2691-2695
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUsing the cannula insertion method, we investigated vascular effects of 7-O-ethyl-fangchinoline (TJN-220) derived from tetrandrine in isolated and perfused common carotid arteries of Wistar Kyoto rats (WKY) and spontaneously hypertensive rats (SHR). A single dose of TJN-220 caused a vasodilation in a dose-related manner in arteries preconstricted by phenylephrine. The vasodilation was not inhibited by propranolol, a potent beta-adrenoceptor antagonist. A potent alpha-antagonist bunazasin inhibited the vasoconstriction to norepinephrine while TJN-220 did not modify the norepinephrine-induced constriction, indicating TJN-220 had no alpha-blocking activity. A potent calcium entry blocker, diltiazem, markedly attenuated the KCl-induced vasoconstriction, and TJN-220 slightly but significantly attenuated the KCl-induced one in large doses. The vasodilation of TJN-220 was not abolished after removing the endothelium by an intraluminal administration of saponin, although the ACh-induced dilation was completely abolished by it. A comparison of vascular resposes in WKY and SHR revealed no significant differences. From these results, it is concluded that 1) a new tetrandrine derivative, TJN-220 has relatively long- lasting vasorelaxant properties, 2) the dilatory effects might not be related to adrenergic, muscarinic or endothelium-dependent mechanisms, and 3) the effects might partially be due to calcium entry antagonistic properties.View full abstractDownload PDF (705K) -
Shoko YOKOYAMA, Fumio UEDA, Tadao FUJIE1991 Volume 39 Issue 10 Pages 2696-2698
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe rates of release of nicotinamide (NAA) from fatty acid (FA)-NAA complexes, FA-NAA, were determined in a JP XI dissolution test apparatus in 500 ml of JP XI disintegration test medium No. 1 at 37°C. The release rate constant (k) and the activation Gibbs energy (ΔG〓) for the release of NAA from FA-NAA were estimated. The results obtained for FA-NAA were compared with previous results obtained for the thiamine disulfide (TDS) complex, (FA)6-(TDS).The plots of log k against the carbon number of the constituent FA (n) presented a zig-zag line which indicates a downward convex at an odd-numbered position. The plots of ΔG〓 against n showed a zig-zag line with an upward convex at an odd-numbered position, though the positive value of ΔG〓 increased rather regularly with an increase of n for either even-numbered or odd-numbered FA.The phonomena that the plots of log k vs. n and ΔG〓 vs. show zig-zag lines due to the difference between even- and odd-numbered FA were the same as observed previously for the relase of TDS from (FA)6 (TDS).View full abstractDownload PDF (565K) -
Tadahiro TAKEDA, Keisuke KOJIMA, Yukio OGIHARA1991 Volume 39 Issue 10 Pages 2699-2701
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIsomers of O-α-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→6)-N-[L-aspart-1-onl-(L-proline)4-oyl]-α-D-glucopyranosylamine have been prepared, as models for a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding dipeptide derivative (5) with triglycosylamine (4) in the presence of O, O-diethylcyanophosphonate, followed by deprotection of the trisaccharide-dipeptide derivative. During the deprotection process, cis- and trans-isomers containing proline were separated by silica gel column chromatography and also reversed-phase high performance liquid chromatography.View full abstractDownload PDF (576K) -
Kosaku HIROTA, Shoji ONOGI, Yoshifumi MAKI1991 Volume 39 Issue 10 Pages 2702-2705
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(4R, 6S)-4-Hydroxy-6-hydroxymethyl-3, 4, 5, 6-tetrahydro-2H-pyran-2-one (1) and (4R, 6S)-4-hydroxy-6-hydroxymethyl-2-methoxytetrahydropyran (2), chirons of the β-hydroxy-δ-lactone moiety of mevinic acids and congeners, were derived from 1, 2, 3, 6-tetra-O-acetyl-α-D-idose (5), which is easily available from penta-O-acetyl-β-D-glucose (3).View full abstractDownload PDF (710K) -
Hideo TAKEDA, Takeshi TACHINAMI, Shigeki HOSOKAWA, Masakazu ABURATANI, ...1991 Volume 39 Issue 10 Pages 2706-2708
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(S)-(-)-2-Methyl succinamic acid, which is a good precursor of (S)-(-)-3-methyl-γ-butyrolactone, can be prepared by homogeneous asymmetric hydrogenation of 2-methylene succinamic acid catalyzed by (2S, 4S)-N-substituted-4-(diphenylphosphino)-2-[(diphenylphosphino)-methyl]pyrrolidine-rhodium complexes. Various N-substituted pyrrolidine-bisphosphines were synthesized to find the optimum ligand for this purpose and to compare the effects of the N-substituents.View full abstractDownload PDF (643K) -
Fumiko ABE, Yujiro MORI, Tatsuo YAMAUCHI1991 Volume 39 Issue 10 Pages 2709-2711
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3'-epi-19-Norafraside, a 19-norcardenolide glycoside with dual linkages between a cardenolide and 4, 6-dideoxy-galactos-2-ulose, and 12β-hydroxycoroglausigenin were newly isolated from the stems of Asclepias curassavica, along with known glycosides and free cardenolides. The structures were determined by spectral and chemical methods.View full abstractDownload PDF (507K) -
Hisashi ISHII, Sunao TAKEDA, Koreharu OGATA, Miyoji HANAOKA, Takashi H ...1991 Volume 39 Issue 10 Pages 2712-2714
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidation of the enamine (6) to the isocarbostyril (7) was re-examined. Simply stirring a dimethylformamide (DMF) solution of 6 provided 7 with good reproducibility, in the presence of KCN under an oxygen atmosphere. The structure of the chloroform adduct (8) was determined by an X-ray analysis.View full abstractDownload PDF (606K) -
Nobutoshi MURAKAMI, Takashi MORIMOTO, Keiko MATSUO, Shin-ichi NAGAI, T ...1991 Volume 39 Issue 10 Pages 2715-2717
Published: October 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to obtain adducts of 8-methoxypsoralen (8-MOP, 1) and singlet oxygen (1O2), the oxidation of 1 with chemically generated singlet oxygen in H2O2-NaOCl was undertaken. Bioassay-directed fractionation of the crude oxidized products has led to the isolation and characterization of a novel derivative of 1, 2, 3-dihydro-2, 9-dimethoxy-3-hydroxy-7H-furo[3, 2-g][1]benzopyran-7-one (2) as a substance inhibiting chemotactic activity of polymorphonuclear neutrophils toward anaphylatoxin C5a des Arg. The structure of 2 was determined from the spectroscopic data and by correlation with its acetate (2a). Furthermore, the oxidation of 1 in H2O2-NaOCl afforded 5-chloro-9-methoxy-7H-furo[3, 2-g][1]benzopyran-7-one (3) and 6-formyl-7-hydroxy-8-methoxy-2H-1-benzopyran-2-one (4) along wiht 1, but they exhibited no such activity.View full abstractDownload PDF (590K)