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Zhizhen ZHANG, Kazuo KOIKE, Zhonghua JIA, Tamotsu NIKAIDO, Dean GUO, J ...
1999 Volume 47 Issue 11 Pages
1515-1520
Published: November 15, 1999
Released on J-STAGE: March 31, 2008
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Eight new acylated polyhydroxyoleanene triterpenoidal saponins, aesculiosides A-H (1-8), along with four known ones, have been isolated from the seeds of Aesculus chinensis. On the basis of extensive NMR studies, the structures of the new compounds were determined to be 21-O-tigloylprotoaescigenin 3-O-[β-D-glucopyranosyl-(1→2)][β-D-glucopyranosyl-(1→4)]-β-D-glucuronopyranosyl acid (1), 21-O-angeloylprotoaescigenin 3-O-[β-D-glucopyranosyl-(1→2)][β-D-glucopyranosyl-(1→4)]-β-D-glucuronopyranosyl acid (2), 21, 22-O-ditigloylprotoaescigenin 3-O-[β-D-glucopyranosyl-(1→2)][β-D-glucopyranosyl-(1→4)]-β-D-glucuronopyranosyl acid (3), 21-O-tigloyl-22-O-angeloylprotoaescigenin 3-O-[β-D-glucopyranosyl-(1→2)][β-D-glucopyranosyl-(1→4)]-β-D-glucuronopyranosyl acid (4), 21, 22-O-ditigloylprotoaescigenin 3-O-[β-D-glucopyranosyl-(1→2)][β-D-glucopyranosyl-(1→4)]-methyl β-D-glucuronopyranosate (5), 21-O-tigloyl-22-O-angeloylprotoaescigenin 3-O-[β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-methyl β-D-glucuronopyranosate (6), 21-O-tigloyl-28-O-acetylprotoaescigenin 3-O-[β-D-glucopyranosyl-(1→2)][β-D-glucopyranosyl-(1→4)]-methyl β-D-glucuronopyranosate (7) and 21-O-angeloyl-28-O-acetylprotoaescigenin 3-O-[β-D-glucopyranosyl-(1→2)][β-D-glucopyranosyl-(1→4)]-methyl β-D-glucuronopyranosate (8).
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Katsuhiro HAYASHI, Sadaaki KOMURA, Noriko ISAJI, Nobuko OHISHI, Kunio ...
1999 Volume 47 Issue 11 Pages
1521-1524
Published: November 15, 1999
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One new and 11 previously known antioxidative compounds were isolated from Brazilian propolis. The new compound was determined as 3, 4-dihydroxy-5-prenylcinnamic acid (3-[3, 4-dihydroxy-5-(3-methyl-2-butenyl)-phenyl]-2-(E)-propenoic acid) by various physical analyses (MS, IR,
1H-NMR,
13C-NMR, and 2D-NMR). The inhibitory activity of each compound against peroxidation of linoleic acid in a micelle solution was measured. We found that the novel compound possessed the highest potency (IC
50, 0.17 μM) among them and was more effective than butylated hydroxytoluene (BHT; IC
50, 0.36 μM) under the experimental conditions employed. Among the isolated antioxidative compounds, 3, 5-diprenyl-4-hydroxycinnamic acid (artepillin C; IC
50, 0.44 μM) was found to be most abundant in Brazilian propolis.
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Kozo AKASAKA, Hiroshi AKAMATSU, Yuichi KIMOTO, Yuki KOMATSU, Toshikazu ...
1999 Volume 47 Issue 11 Pages
1525-1531
Published: November 15, 1999
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Diastereoselective methylation of the enolate generated from various protected 6-oxopipecolic acid esters (3aa-3cd) was studied. The protecting groups on the carboxylic acid and amino groups significantly influenced the trans/cis selectivity in the methylation reaction. The optimal substrate (3ca), bearing benzhydryl ester and carbobenzyloxy moieties gave a trans/cis isomer ratio of ca. 4 : 1. Investigation of the reaction conditions revealed that the reaction solvent, alkylating reagent, and base employed to generate the enolate, were decisive factors for diastereoselectivity. Further optimization of reaction conditions, including the amounts of the reagents and their addition sequence enabled maximization of reaction conversion and minimization of by-products to produce the trans rich 5-methyl-6-oxopipecolic acid ester (4ca) on a large scale.
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Kozo AKASAKA, Yuki KOMATSU, Katsuya TAGAMI, Toshikazu SHIMIZU, Naoyuki ...
1999 Volume 47 Issue 11 Pages
1532-1537
Published: November 15, 1999
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An efficient synthetic process for the key intermediate of a new peptidomimetic dual metalloprotease inhibitor, ER-40133, was developed. (5R)-Methyl-6-oxopipecolic acid ester (3a), prepared from L-α-aminoadipic acid, was chemoselectively reduced to the protected (5R)-methyl-6-hydroxypipecolic acid ester (4a), followed by treatment with L-cysteine methyl ester to give the linear key intermediate (5a) with the desired configuration. After deprotection of the ester moiety of 5a, the newly generated carboxylic acid group was intramolecularly condensed with the amino group at the thiazolidine ring using ethyl chloroformate in the presence of base to provide [5.7]-bicyclic compound (7a) with the desired configuration in excellent yield. Lastly, the methyl ester of 7a was hydrolyzed under alkaline conditions to afford 8a, a key intermediate for ER-40133.
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Masafumi KITANO, Atsuyuki KOJIMA, Kazuhiro NAKANO, Akira MIYAGISHI, Ts ...
1999 Volume 47 Issue 11 Pages
1538-1548
Published: November 15, 1999
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A series of N-(aminoiminomethyl)-1H-indole carboxamide derivatives were synthesized and their inhibitory potencies against the Na
+/H
+ exchanger were measured. Variation of the carbonylguanidine group at the 2- to 7-position of the indole ring system showed that a substitution at the 2-position improved the Na
+/H
+ exchanger inhibitory activity the most in vitro. This led to the synthesis and evaluation of an extensive series of N-(aminoiminomethyl)-1H-indole-2-carboxamide derivatives. Derivatives having an alkyl or substituted alkyl group at the 1-position of the indole ring system showed higher levels of in vitro activities. N-(aminoiminomethyl)-1-(2-phenylethyl)-1H-indole-2-carboxamide (49) had the strongest activity.
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Tomoyasu OHNO, Shin-go YANO, Haruo YAMADA, Tetsuhiko SHIRASAKA, Akira ...
1999 Volume 47 Issue 11 Pages
1549-1554
Published: November 15, 1999
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The enantiomers of (±)-4-[1-(4-tert-butylphenyl)-2-oxo-pyrrolidine-4-yl]methyloxybenzoic acid (S-2), a new antilipidemic agent having dual action on the plasma triglyceride (TG) and cholesterol (Cho) lowering effects, were prepared via separation by Chiralcel OJ column chromatography of their methyl ester and also by the same method as the described racemate's synthesis from optically active 1-(4-tert-butylphenyl)-2-oxo-pyrrolidine-4-carboxylic acid respectively. These optically active carboxylic acids were prepared by the resolution of diastereomeric N-[(S)-(-)-[4-methyl-(α-methyl)benzyl]]-1-(4-tert-butylphenyl)-2-oxo-pyrrolidine-4-carboxyamide using silica gel column chromatography, followed by deamination with N
2O
4. The absolute configurations for the enantiomers of S-2 were indirectly determined using X-ray analysis of the 4-bromo-2-fluorobenzamide of the (+)-4-[1-(4-tert-butylphenyl)-2-oxo-pyrrolidine-4-yl]-methyloxybenzoic acid. S-2 and its enantiomers showed an essentially equipotent activity on the fatty acid- and sterol-biosynthesis inhibition in vitro. On the other hand, in the in vivo activity, (S)-(+)-4-[1-(4-tert-butylphenyl)-2-oxo-pyrrolidine-4-yl]methyloxybenzoic acid (S-2E) was superior in the lowering abilities of the plasma TG and phospholipid(PL) and was chosen as a candidate for a novel antilipidemic agent. The difference in the in vivo activity among S-2 and its enantiomers was explained from the pharmacokinetics after administration p.o.
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Masayuki HARAMURA, Kouichi TSUZUKI, Akira OKAMACHI, Kenji YOGO, Makoto ...
1999 Volume 47 Issue 11 Pages
1555-1559
Published: November 15, 1999
Released on J-STAGE: March 31, 2008
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Biologically important sites on intact porcine motilin (pMTL) were explored using its partial peptides. The partial peptides were synthesized using Fmoc (9-fluorenylmethyloxycarbonyl) solid phase methodology, and tested for the binding activity to motilin receptor and the smooth muscle contractile activity. The results were as follows : important residues for the contractile activity were found to be Phe
1, Ile
4, and Tyr
7, and an open space existed beyond the N-terminus between motilin and its receptor. On the model of interaction between motilin and motilin receptor evolved from these results, the three points of interaction, due to Phe
1, Ile
4, and Tyr
7, and the presence of an open space were expected. The motilin agonist and antagonist, designed on this model, will help the inquiry into motilin associated diseases.
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Guita N. JUBILUT, Maria Teresa MIRANDA, Mineko TOMINAGA, Yoshio OKADA, ...
1999 Volume 47 Issue 11 Pages
1560-1563
Published: November 15, 1999
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Ideally, the solid support used for tert-butyloxycarbonyl (Boc)-peptide synthesis method must allow sufficient stability of the peptide linkage towards TFA-α-amino deprotection but adequate lability to final HF cleavage. Due to these conflicting characteristics, the choice of the correct resin for peptide synthesis is complex and dependent upon many factors. Aiming to clarify this issue, a time-course study of the trifluoroacetic acid (TFA) and HF steps using model peptidyl-resins was developed. The peptidyl-resin bond stability was strongly dependent upon the resin and the carboxy-terminus residue. The decreasing order of acid stability for resins was : benzhydrylamine-resin (BHAR)>p-methylbenzhydrylamine-resin (MBHAR)≅4-(oxymethyl)-phenylacetamidomethyl-resin (PAMR)>chloromethyl-resin (CMR) and Phe>Gly≅His≅Asp for C-terminal amino acids. HF-cleavage times of near 6 h (BHAR) and 2-3 h (MBHAR and PAMR) were necessary for quantitative cleavage of hydrophobic Phe residue-containing sequence at its C-terminal portion. When premature chain loss in TFA and incomplete cleavage in HF values were both quantitatively considered, a significant decrease in the overall yield (up to 35%) was observed in some resins. Moreover, MBHAR was more suitable than BHAR only when the peptide C-terminal residue is hydrophobic. The data also allow the prediction that due to more significant chain loss in TFA when MBHAR is used, BHAR will be the resin of choice for much longer than 40-mer peptide sequences containing C-terminal hydrophilic residues. Otherwise PAMR is the best resin for the synthesis of free carboxyl peptides but significantly low HF cleavage was observed when the C-terminal amino acid is of the hydrophobic-type.
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Yasuyo OKADA, Kazuha MATSUDA, Koji HARA, Kenichi HAMAYASU, Hitoshi HAS ...
1999 Volume 47 Issue 11 Pages
1564-1568
Published: November 15, 1999
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The novel heterogeneous branched cyclodextrins (CDs), 6-O-α-D-galactosyl-α, -β, and -γCDs (Gal-α, -β, and -γCDs) and 6-O-α-D-mannosyl-α, -β, and -γCDs (Man-α, -β, and -γCDs) dissolved sufficiently in water and in 10-50% (v/v) methanol aqueous solutions, as did the homogeneous branched CDs, 6-O-α-D-glucosyl-α, -β, and -γCDs (Glc-α, -β, and -γCDs). The solubilities of heterogeneous branched CDs were higher than those of each parent non-branched CDs. The hemolytic activities of heterogeneous and homogeneous branched CDs were lower than those of each parent non-branched CDs and the hemolytic activity became weaker in the order of non-branched CD>Man-CD>Glc-CD>Gal-CD in each series of α, β, and γCD. A
L type solubility-phase diagrams were displayed in the formation of inclusion complexes of the guest compounds of small size (methyl benzoate, estriol, and dexamethasone) with Gal-, Man-, and Glc-CDs, and marked differences among the three kinds of branched CDs could not be detected. However, solubility-phase diagrams between these branched CDs and the insoluble guest compounds of large cyclic structure (cyclosporin A, tacrolimus, and amphotericin B) showed A
P type, and the improvement of water solubilities of these guest compounds with three kinds of branched CDs was enhanced in the order of Man-CDs>Glc-CDs>Gal-CDs.
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Bao-Ning SU, Yoshihisa TAKAISHI
1999 Volume 47 Issue 11 Pages
1569-1572
Published: November 15, 1999
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Five new phenylpropanol derivatives, called morinins L-P (1-5), along with two known compounds, 3, 4-dimethoxycinnamylalcohol methyl ether (6) and p-methoxycinnamaldehyde (7), have been isolated from the roots of the medicinal Chinese plant, Morina chinensis. The structures of all the new compounds were determined on the basis of spectral evidence, especially by 2D-NMR and HREIMS. Alkaline hydrolytic degradation confirmed the structure of compound 5.
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Hiroyuki NAKANO, Tsutomu INOUE, Nobuhide KAWASAKI, Hideki MIYATAKA, Hi ...
1999 Volume 47 Issue 11 Pages
1573-1578
Published: November 15, 1999
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Syntheses were conducted of novel benzimidazole derivatives that suppress histamine release from mast cells, inhibit 5-lipoxygenase, and possess antioxidative action. Among the compounds synthesized, 1-[2-[2-(4-hydroxy-2, 3, 5-trimethylphenoxy)ethoxy]ethyl]-2-(4-methyl-1-homopiperazino)benzimidazole (22) potently suppressed histamine release from rat peritoneal mast cells triggered by the antigen-antibody reaction, inhibited 5-lipoxygenase in rat basophilic leukemia-1 (RBL-1) cells, and prevented the NADPH-dependent lipid peroxidation induced by Fe
3+-ADP in rat liver microsomes, in addition to an antagonizing the contraction of guinea pig ileum caused by histamine.
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Chihiro ITO, Yuichi KONDO, K. Sundar RAO, Harukuni TOKUDA, Hoyoku NISH ...
1999 Volume 47 Issue 11 Pages
1579-1581
Published: November 15, 1999
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Chemical constituents of MeOH-CH
2Cl
2 extract of the stem of Glycosmis pentaphylla RETZ (Rutaceae) collected in Papua New Guinea were studied. A novel naphthoquinone and a new acridone alkaloid called glycoquinone (1) and glycocitrine-III (2), respectively, were isolated along with twelve known compounds, and their structures were elucidated by spectrometric analyses. This is the first isolation of a naphthoquinone derivative from the genus Glycosmis.
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Takao TANAHASHI, Takeshi SAKAI, Yukiko TAKENAKA, Naotaka NAGAKURA, Che ...
1999 Volume 47 Issue 11 Pages
1582-1586
Published: November 15, 1999
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Phytochemical investigation of the dried leaves of Jasminum officinale var. grandiflorum has led to the isolation of two new secoiridoid glucosides, (2"R)-2"-methoxyoleuropein and (2"S)-2"-methoxyoleuropein, together with four known secoiridoid glucosides, oleuropein, ligstroside, demethyloleuropein and oleoside dimethyl ester, a lignan, (-)-olivil and p-hydroxyphenethyl alcohol. The structures of the new compounds were elucidated from chemical and spectroscopic evidence.
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Kumi OSANAI, Yuusaku YOKOYAMA, Kazuhiro KONDO, Yasuoki MURAKAMI
1999 Volume 47 Issue 11 Pages
1587-1590
Published: November 15, 1999
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The first total synthesis of optically active costaclavine (18), an ergot alkaloid, was accomplished starting from methyl [4R-(Z)]-[4-[[(1, 1-dimethylethoxy)carbonyl]methylamino]-3, 4-dihydro-1-[(4-methylphenyl)sulfonyl]-benz[cd]indol-5(1H)-ylidene]acetate (8), which was prepared by intramolecular cyclization of 1, 1-dimethylethyl[1R-(E)]-[1-[[4-bromo-1-[(4-methylphenyl)-sulfonyl]-1H-indol-3-yl]methyl]-4-carbomethoxy-2-propenyl]methylcarbamate (7) according to the method we developed earlier during the course of the total synthesis of chanoclavine-I (9).
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Tomoo HOSOE, Koohei NOZAWA, Trevor C. LUMLEY, Randolph S. CURRAH, Kazu ...
1999 Volume 47 Issue 11 Pages
1591-1597
Published: November 15, 1999
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The culture filtrate of a fungus isolated from decaying Picea glauca wood and tentatively identified as Oidio-dendron cf. truncatum showed strong antibiotic activity against the pathogenic yeast, Candida albicans. Four new tetranorditerpenoids, oidiodendrolides A (3), B (4), and C (5) and oidiodendronic acid (7) were isolated along with three known tetranorditerpenoids, LL-Z1271α (=PR1387) (1), PR1388 (2), and acrostalidic acid (6), from rice fermented by the above fungus. The structures of oidiodendrolides A (3), B (4), and C (5) and oidiodendronic acid (7) were established on the basis of spectroscopic and chemical investigations. The antifungal activity of the above tetranorditerpenoids against the pathogenic yeasts, Candida albicans and Cryptococcus neoformans is discussed.
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Kazuko YOSHIKAWA, Kumiko TAKAHASHI, Koji MATSUCHIKA, Shigenobu ARIHARA ...
1999 Volume 47 Issue 11 Pages
1598-1603
Published: November 15, 1999
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From the fresh roots of Gymnema alternifolium, nine new oleanane-type triterpenoid glycosides, named alternosides XI-XIX (1-9), were isolated, together with two artificial compounds 10 and 11, and two known compounds, sitakisosides X (12) and XVII (13). Their structures were determined on the basis of spectroscopic data and chemical evidence. Compounds 1-3 are 3-O-glycosides of chichipegenin having a tigloyl group at C-22, 28 and 16, respectively. Compounds 4-7 are 3, 28-bis-O-glycosides of chichipegenin having a tigloyl group at C-22. Compounds 8 and 9 are 3, 28-bis-O-glycosides of longispinogenin. Compounds 1-7 having an acyl group showed antisweet activity.
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Abdelhakim ELOMRI, Sylvie MICHEL, Michel KOCH, Elisabeth SEGUIN, Franc ...
1999 Volume 47 Issue 11 Pages
1604-1606
Published: November 15, 1999
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Condensation of 2-chloro-3-nitrobenzoic acid with either 5-amino-7-methoxy-2, 2-dimethyl-2H-chromene or 5-amino-2, 2-dimethyl-2H-chromene afforded diphenylamines 14 and 15. Trifluoroacetic anhydride mediated cyclization gave the corresponding acridones 16 and 17, which were subsequently N-methylated and reduced to 11-aminoacronycine and 11-amino-6-demethoxyacronycine.These two amino compounds, which gave stable water soluble salts, were 2- to 3-fold more potent than acronycine or 6-demethoxyacronycine in inhibiting L1210 cell proliferation.
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Akikazu KAKEHI, Suketaka ITO, Hoh SA
1999 Volume 47 Issue 11 Pages
1607-1613
Published: November 15, 1999
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Title compounds were prepared in 20-72% yields from the S-aklylation of pyridinium 1- [3-ethoxycarbonyl-1-[(methylthio)thiocarbonyl]]allylides with some alkyl halides, followed by the treatment of the resulting pyridinium salts with a base and then a dehydrogenating agent. In part of these reactions novel heterocycles, ethyl 1-cyano-3-(methylthio)thieno[3, 4-b]indolizine-9-carboxylates, were also formed. The oxidation of the title compounds with m-chloroperbenzoic acid gave the corresponding sulfoxides in moderate to good yields, which smoothly underwent Pummerer reactions on treatment with acetic anhydride. The bromination of the 3-vinyl group in the title compounds, followed by treatment of the resulting dibromo adducts with a base afforded ethyl 2-bromo-3-[2-(methylthio)indolizin-3-yl]acrylates, 3-[1-cyano-2-(methylthio)indolizin-3-yl]propiolates, and ethyl thieno[2, 3-b]indolizine-2-carboxylate depending upon the substrate used.
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R. M. El-SHAZLY
1999 Volume 47 Issue 11 Pages
1614-1617
Published: November 15, 1999
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Complexes of ethyl-α-(N-phenylthiocarbamyl)acetoacetate (HEPTA) with Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Pd(II) have been prepared and characterized on the basis of elemental analyses, molar conductance, magnetic moment and spectral (UV-Visible, ESR and IR) studies. IR spectra show that HEPTA behaves in a neutral or mononegative bidentate manner. A tetrahedral structure is proposed for the Co(II) complex while a square-planar structure is proposed for the Ni(II), Cu(II) and Pd(II) complexes. The thermal stability and the decomposition steps of [Ni(EPTA)
2] and [Cu(EPTA)(OAc)] were investigated with the help of TG thermograms. The Ni(II) and Co(II) complexes show two well defined electrode processes M
I/M
II and M
II/M
III in dimethylform-amide(DMF), while the Cu(II) complex shows one electrode couple assigned to Cu(II/I).
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Haruhisa KIZU, Ei-ichi KANEKO, Tsuyoshi TOMIMORI
1999 Volume 47 Issue 11 Pages
1618-1625
Published: November 15, 1999
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From the dried roots of Dactylorhiza hatagirea, which are termed Panch Aunle in Nepal, five new compounds called dactylorhins A, B, C, D and E, and two new natural compounds named dactyloses A and B, have been isolated together with twelve known compounds. In addition to these compounds, two kinds of lipid mixture were also obtained.The structures of the new compounds have been determined by spectroscopic and chemical methods as follows : dactylorhin A, (2R)-2-β-D-glucopyranosyloxy-2-(2-methylpropyl)butanedioic acid bis(4-β-D-glucopyranosyloxybenzyl) ester; dectylorhin B, (2R, 3S)-2-β-D-glucopyranosyloxy-3-hydroxy-2-(2-methylpropyl)butanedioic acid bis(4-β-D-glucopyranosyloxybenzyl) ester; dactylorhin C, (2R)-2-β-D-glucopyranosyloxy-2-(2-methylpropyl)butanedioic acid; dactylorhin D, (2R, 3S)-2-β-D-glucopyranosyloxy-3-hydroxy-2-(2-methylpropyl)butanedioic acid 1-(4-β-D-glucopyranosyloxybenzyl) ester; dactylorhin E, (2R)-2-β-D-glucopyranosyloxy-2-(2-methylpropyl)butanedioic acid 1-(4-β-D-glucopyranosyloxybenzyl) ester; dactylose A, 1-deoxy-1-(4-hydroxyphenyl)-L-sorbose; dactylose B, 1-deoxy-1-(4-hydroxyphenyl)-L-tagatose.Although a mixture of dactyloses A and B has been already synthesized, this is the first example of their isolation from natural resources.Dactyloses A and B were suggested to be biosynthesized from L-ascorbic acid and 4-hydroxybenzyl alcohol via 2-C-(4-hydroxybenzyl)-α-L-xylo-3-ketohexulofuranosono-1, 4-lactone.
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Hitoshi ISHIDA, Yasunori INAOKA, Akira NOZAWA, Jun-ichi SHIBATANI, Mak ...
1999 Volume 47 Issue 11 Pages
1626-1628
Published: November 15, 1999
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The crystal structure of polyporusterone A, from Polyporus umbellatus F. was determined by X-ray diffraction analysis. The crystals are orthorhombic, space group P2
12
12
1, Z=4, unit-cell dimension a=17.968(2), b=26.201(5), c=6.227(1) Å. The structure, (+)-2β, 3β, 14α, (20R, 22R)-pentahydroxy-(24S)-methyl-5β-cholest-7-en-6-one, was solved from diffractometric data by direct methods and refined by least-squares calculations to R=0.053 (2345 observed independent significant reflections (I>3σ(I)). All the hydroxyl groups are involved in a hydrogen-bonding network. The NMR data indicate that the side-chain has the same conformation in both the crystalline state and solution.
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Paloma DE LA TORRE, Susana TORRADO, Santiago TORRADO
1999 Volume 47 Issue 11 Pages
1629-1633
Published: November 15, 1999
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Solid dispersions of praziquantel (PZQ) containing varying concentrations of polyvinylpyrrolidone (PVP) with different molecular weights (3000, 11000 and 34000) were prepared in an attempt to improve the solubility and dissolution rate of PZQ. The physical characteristics of PZQ, physical mixtures and solid dispersions were investigated by a variety of analytical methods including scanning electron microscopy (SEM), differential scanning calorimetry (DSC) and powder X-ray diffraction (XRD). The solubility of PZQ in the coprecipitate was greater when PVP of a smaller molecular weight was used. The dissolution rate of the drug in the coprecipitate was faster when the ratio of the drug to PVP was smaller (1 : 9). SEM was especially useful in the verification of possible PZQ inclusion in the PVP matrix due to the morphological and physical differences between PZQ and PVP. The physical mixture and solid dispersion DSC scans did not present a clear endothermic peak, perhaps due to low PZQ enthalpy.The dissolution rate was significantly increased when the PZQ : PVP ratio was at least 1 : 5, which agrees with the inclusion of PZQ in the PVP matrix, as observed by SEM, and the amorphous pattern shown by XRD.
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Hiroshi KUWAJIMA, Takao TANAHASHI, Kenichiro INOUE, Hiroyuki INOUYE
1999 Volume 47 Issue 11 Pages
1634-1637
Published: November 15, 1999
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A biosynthetic pathway from secologanin to oleoside-, 10-hydroxyoleoside- and ligustaloside-type secoiridoid glucosides was examined by feeding experiments in which the respective C-8 stereoisomers of [8-
3H]-8, 10-epoxyse cologanin and [8-
3H]-8, 10-epoxysecoxyloganin as well as [carbomethoxy-
2H
3]secologanin were administered separately to three oleaceous plants. The results showed that (8S)-8, 10-epoxysecologanin was an intermediate between the secologanin and secoiridoid glucosides of the three types.
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Masato OHTA, Yuichi TOZUKA, Toshio OGUCHI, Keiji YAMAMOTO
1999 Volume 47 Issue 11 Pages
1638-1640
Published: November 15, 1999
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The heat of crystallization and heat of solution of cefditoren pivoxil of different crystallinities were determined by differential scanning calorimetry and isothermal microcalorimetry, respectively. The heat of crystallization and heat of solution of ground cefditoren pivoxil showed good linear correlation with the degree of crystallinity determined by Ruland's method by powder X-ray diffractogram. The changes in crystallinity of amorphous cefditoren pivoxil by adsorption of alcohol vapor could be evaluated for small amounts of sample by use of heat of crystallization. Since the apparent dissolution rate of cefditoren pivoxil of various crystallinities correlated with the heat of solution, microcalorimetry was found to be useful for prediction of dissolution behavior.
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Noriyuki USAMI, Takeshi OKUDA, Hisatoshi YOSHIDA, Toshiyuki KIMURA, Ka ...
1999 Volume 47 Issue 11 Pages
1641-1645
Published: November 15, 1999
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Six halogenated derivatives of cannabidiol (CBD, 1) substituted on the aromatic ring at the 3' and/or 5' position, 3'-chloro- (2), 3', 5'-dichloro- (3), 3'-bromo- (4), 3', 5'-dibromo- (5), 3'-iodo- (6) and 3', 5'-diiodo-CBD (7) were synthesized and their pharmacological effects of barbiturate-induced sleep prolongation, anticonvulsant effects and locomotor activity were evaluated by intravenous (i.v.) injection in mice. 2 (10 mg/kg, i.v., 69±10 min) significantly prolonged pentobarbital-induced sleeping time by 3.1-fold, compared to control (22±2 min), although other 1 derivatives used did not significantly affect the sleeping time. 2, 4 and 6 (10 mg/kg, i.v.) significantly prolonged hexobarbital-induced sleeping time by 2.0-, 2.0- and 2.3-fold, respectively, compared with control (52±5 min). On the other hand, 1 and all halogenated derivatives did not significantly prolong barbital-induced sleeping time. The monohalogenated derivatives, 2, 4 and 6 were able to prolong pentobarbital and hexobarbital-induced sleeping time, although the dihalogenated derivatives, 3, 5 and 7 did not exhibit a prolongation of the sleeping time. All halogenated derivatives of 1 except for brominated derivatives (2, 3, 6, 7) tended to prolong tonic seizure latency induced by pentylenetetrazol. 1 and its halogenated derivatives did not exhibit any prolongation of seizure latency induced by picrotoxin or strychnine. Maximal electroshock test demonstrated that 1 and 4 exhibited almost the same potency in their anticonvulsant effects, although other 1 derivatives 2, 3, 5, 6 and 7 did not show significant effect up to a dose of 63 mg/kg, i.v. The ED
50 values (mg/kg, i.v.) of 1 and 4 were 38 and 44, respectively. 1 and 4 also showed anticonvulsant effect in minimal and maximal electroshock-threshold tests. 2, 4 and 6 tended to decrease the total distance (horizontal activity) and number of rearings (vertical activity) of mice, whereas 3, 5 and 7 tended to increase the number of rearings. However, the effects of all derivatives were not statistically significant from the control. 2 and 4 were the most potent derivatives on pharmacological activities among the synthetic cannabinoids examined in the present study. These results indicate that monohalogenation of 1 leads to some modification of the pharmacological profile of CBD.
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Masanori KUROYANAGI, Kazutoshi SHIBATA, Kaoru UMEHARA
1999 Volume 47 Issue 11 Pages
1646-1649
Published: November 15, 1999
Released on J-STAGE: March 31, 2008
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In the course of screening for cell differentiation inducers from botanical sources, the methanol extract of Withania somnifera L. (DUN.) showed activity. From the aerial parts of the plant, sixteen withanolides, including three new compounds, 14, 15 and 16, were isolated and their structures elucidated to be (20S, 22R)-4β, 5β, 6α, 27-tetrahydroxy-1-oxo-witha-2, 24-dienolide, (20R, 22R, 24S, 25R)-4β, 20β-dihydroxy-5β, 6β-epoxy-3β-methoxy-1-oxo-withanolide and 3-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl]-(20S, 22R)-1α, 3β-dihydroxywitha-5, 24-di-enolide, respectively, from the spectral data. Of these withanolides, 1, 2, 3 and 4 showed potent cell differentiation inducing activity against M1 cells. The most potent compound, 3, showed more potent activity than dexamethasone, the positive control. These active compounds have the same partial structure of the AB ring part, having a 4β-hydroxy-5β, 6β-epoxy-2-en-1-one moiety.
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Toshiharu YANAGI, Akihiko KITAJIMA, Kinsei ANZAI, Kazuya KODAMA, Jun-i ...
1999 Volume 47 Issue 11 Pages
1650-1654
Published: November 15, 1999
Released on J-STAGE: March 31, 2008
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Of 4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4-pyrrolidinyl)benzamide, four optical isomers, (2S, 4S)-1 (TKS159), (2S, 4R)-25, (2R, 4S)-26 and (2R, 4R)-27, were prepared from optically active 4-amino-1-ethyl-2-hydroxymethylpyrrolidine di-p-toluenesulfonate [(2S, 4S)-14, (2S, 4R)-17, (2R, 4S)-20 and (2R, 4R)-23, respectively]. The requisites, (2S, 4S)-14, (2S, 4R)-17, (2R, 4S)-20 and (2R, 4R)-23, were prepared from a commercially available trans-4-hydroxy-L-proline. The absolute configurations of (2S, 4S)-1 (TKS159), (2S, 4R)-25, (2R, 4S)-26 and (2R, 4R)-27 were spectroscopically determined. Of the benzamide derivatives, four optical isomers, (2S, 4S)-1, (2S, 4R)-25, (2R, 4S)-26 and (2R, 4R)-27, showed a relatively potent affinity for 5-hydroxytryptamine 4 (5-HT
4) receptors in a radioligand binding assay ([
3H]GR113808). The activities of 25-27 were less effective than that of 1 for the gastric emptying of a phenol red semisolid meal in rats. All this suggests that the most potent of the isomers was 4-amino-5-chloro-2-methoxy-N-[(2S, 4S)-1-ethyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide (1).
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Takahiro UCHIDA, Noboru SEKIYA, Yuka TOIDA, Noriko YASUDA, Keiko TAZUY ...
1999 Volume 47 Issue 11 Pages
1655-1658
Published: November 15, 1999
Released on J-STAGE: March 31, 2008
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The objective of this study was to prepare and evaluate the possibility of cylindrical xerogel preparations with zero-order release characteristics. As model polymers, polyvinyl alcohol (PVA), hydroxypropyl methylcellulose (HPMC), and acrylic block copolymers of methacrylic acid and the methacrylate, Eudispert, were selected and formed into xerogel formulations. Tegafur, 5-fluorouracil (5-FU), aspirin, benzoic acid, p-methoxybenzoic acid, theophylline, and salicylamide were employed as model compounds and thereby incorporated into xerogel matrices.In a dissolution test (rotating basket method; pH 7.4), PVA xerogel did not erode nor swell in dissolution medium, and did not exhibit zero-order release, but rather exhibited Fickian's law diffusion followed by the initial burst release profile. In the case of HPMC xerogel, swelling of the polymer was observed to some extent, but the release profile was almost the same as PVA, suggesting the Fickian diffusion of drug from HPMC gel; in contrast, Eudispert gel showed zero-order release in every drug. The polymer was also gradually dissolved into the medium at a zero order release rate.Finally, the Eudispert xerogel containing theophylline was orally administered to beagle dogs, and plasma was withdrawn periodically. The sustained-release characteristics were observed and the possibility of the cylindrical xerogel preparation for oral usage was demonstrated.
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Jie XIA, Yong-Zheng HUI
1999 Volume 47 Issue 11 Pages
1659-1663
Published: November 15, 1999
Released on J-STAGE: March 31, 2008
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Synthesis of a series of mixed-acid phospholipids containing a polyunsaturated fatty acid using a newly protecting strategy are described. Thus, benzyl and methyl α-(2, 4-dinitrophenyl)acetic acid which were respectively removed by BCl
3, and 354 nm light are used as protecting groups.
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Hongquan DUAN, Yoshihisa TAKAISHI, Yongfong JIA, Duan LI
1999 Volume 47 Issue 11 Pages
1664-1667
Published: November 15, 1999
Released on J-STAGE: March 31, 2008
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Five new sesquiterpene pyridine alkaloids, named wilfordinines D (1), E (2), F (3), G (4) and H (5), along with six known compounds have been isolated from the extracts (T
II) of Tripterygium wilfordii Hook F. Their structures were elucidated by spectroscopy.
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Yae FUJISAWA, Hiromu SAKURAI
1999 Volume 47 Issue 11 Pages
1668-1670
Published: November 15, 1999
Released on J-STAGE: March 31, 2008
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A vanadyl complex, bis(6-methylpicolinato)oxovanadium(IV), VO(6MPA), with VO(N
2O
2) coordination mode, was found to exhibit a normoglycemic effect on KKA
y mice with hereditary noninsulin-dependent diabetes mellitus with daily oral administration.
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