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HIDEO KUBODERA, SETSUKO NAKAGAWA, HIDEAKI UMEYAMA
1987 Volume 35 Issue 5 Pages
1673-1685
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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New additional charge sets, which were added to correct the electrostatic potential (ESP) values on the van der Waals molecular surface using Mulliken net atomic charges, were found to reproduce
ab initio ESP with the STO-3G basis set. The charge sets were obtained for fundamental small molecules (water, ammonia. methane. ethane, and benzene). Lone pair regions of oxygen and nitrogen atoms show remarkable improvement, while pi electrons do not contribute much to ESP. The present work opens a way for treating large molecules of biological interest.
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NAOYASU ISHIZUKA, MASAHIRO TOGASHI, MASAMI INOUE, SABURO ENOMOTO
1987 Volume 35 Issue 5 Pages
1686-1690
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The asymmetric hydrogenation of 3, 4-methylenedioxy-α-acetamidocinnamic acid was carried out in the presence of a chiral Rh (I) -complex of (2
S, 4
S) -
N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine (BPPM) adsorbed on hydrophobic silica gel in MeOH- H
2O solvents. Excellent conversions (100%) and a high optical yield (85%) were attained with [Rh (COD) BPPM]
+ClO
4- on methylated silica gel. The adsorption of the complex was improved byintroducing a stearoyl group instead of the butoxycarbonyl group of BPPM. When the recovered catalysts were reused three times, the optical yields decreased gradually from 85 to 69%.
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TOSHIMASA ISHIDA, YOSHIKO TOKURA, MARI SHIMAMOTO, MITSUNOBU DOI, MASAT ...
1987 Volume 35 Issue 5 Pages
1691-1701
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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As a model compound for the interaction of tryptophan with nucleic acid bases, uracil and adenine, (uracil-1-ylethyl) (adenin-9-ylethyl) tryptophan dipeptide has been synthesized, and its molecular and crystal structure has been analyzed by the X-ray diffraction method. The crystal data are
a=4.989 (2),
b=30.056 (5),
c=9.939 (1) Å, β=94.61 (3) °,
Z=2,
Dm=1.345 (1) g·cm
-3, space group
P2
1. The molecule takes a W-shaped extended conformation, and is linked with the neighboring molecule in a head-to-tail fashion through a reverse Watson-Crick base pairing. Consequently the molecules form an infinite chain along the
b-axis. A weak stacking interaction is observed between the indole ring and the uracil base : the dihedral angle between them is 28.6 (3) °, and the average interplanar spacing is 3.95 Å. This stacking mode is formed by the dipole-dipole coupling between the respective aromatic rings.The result may indicate a possible access mode of a tryptophan residue to the uracil base of a single-stranded nucleic acid.
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KENJI KANO, BUNJI UNO, NAOKI KAIDA, ZHENG-XING ZHANG, TANEKAZU KUBOTA, ...
1987 Volume 35 Issue 5 Pages
1702-1714
Published: May 25, 1987
Released on J-STAGE: February 12, 2010
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In connection with the carcinogenic activity of 4- (hydroxyamino) quinoline
N-oxide (4HAQO), voltammetric studies of the oxidation processes of 4HAQO and related substances were carried out in aqueous solutions. It was verified that 4HAQO forms a reversible redox couple with 4-nitrosoquinoline
N-oxide (4NOQO) through an intermediate free radical. The reversible reactions in these redox couples were evaluated quantitatively, and the formation constant of the intermediate free radical was calculated. The pH dependence of the above standard redox potential gave the p
Ka values, which agreed quite well with the data measured by ultraviolet spectral methods. The molecular structures of species formed by proton addition or dissociation were investigated by analyses of the p
Ka values and the electronic spectra, and by their molecular orbital calculations. The
N-oxide type structure was considered to be a main species in aqueous solutions of 4HAQO and its analogues.
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MASAYUKI NAKAGAKI, HIROAKI ICHIHASHI
1987 Volume 35 Issue 5 Pages
1715-1723
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Mixtures of triolein and poly (γ-methyl L-glutamate) (PMLG) were spread on a water-air interface from a helix-favoring solvent and surface pressure-mean area curves were obtained with a surface balance of horizontal float type. The mixtures separated into two or three surface phases at almost all compositions. At relatively low surface pressures, two surface phases, one rich in PMLG and the other rich in triolein, co-existed and at 7 mN/m both changed to a unique duplex film consisting of equi-area PMLG and triolein phases. This duplex film was broken up at 23.5 mN/m. In this system several other phase equilibria between three surface phases were shown.
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BERNARD VIOSSAT, NGUYEN-HUY DUNG, JEAN-CHARLES LANCELOT, SIMONE BENAZE ...
1987 Volume 35 Issue 5 Pages
1724-1733
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The synthesis of 1, 4-dihydro-4-oxo-2, 5, 11-trimethy1-6
H-pyrido [3, 2-2
b] carbazole was described and the lactam-lactim tauromerism was discussed.
C
18H
16N
2O crystallizes in space group
P2
1/
c with
Dm=1.30 (2) Mg·m
-3 in acetonitrile with
a=16.179 (4),
b=14.900 (3).
c=12.702 (3) Å, β=112.28 (2),
V=2833.6 Å
3,
Z=8. The crystalstructure was investigated by X-ray diffraction method with final
R=0.04 for 2355 independent reflections. In the two molecules, the lactam form was observed while the lactim for was found with many derivatives as well in solid state as in solution. The carbazole ring is planar while the 1, 4- dihydro-4-oxo-pyridine deviates from planarity. The molecules have rather small overlapping and the molecular packing involves many hydrogen bonds.
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YOSHIYASU TERAO, MASAHIRO AONO, NOBUYUKI IMAI, KAZUO ACHIWA
1987 Volume 35 Issue 5 Pages
1734-1740
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Thermolysis of bromo (trimethylsilyl) methyl trimethylsilylmethyl sulfide was found to give a thiocarbonyl ylide, the 1, 3-cycloaddition of which proved a new method for the synthesis of tetrahydrothiophenes. The effect of the silyl group of the ylide on the regio- and stereoselectivity in these 1, 3-dipolar cycloadditions is discussed.
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HIROSHI SUEMUNE, KOUJI OKANO, HIROYUKI AKITA, KIYOSHI SAKAI
1987 Volume 35 Issue 5 Pages
1741-1747
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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This paper describes the enzymatic hydrolysis of the
trans,
trans (
meso) -2-substituted 1, 3- bis (acetoxymethyl) cyclopentanes (4a, b) to afford the monoacetates (5a, b) in high enantiomeric excess ((-) -5a : 96% ee, (-) -5b : >99% ee). The absolute stereochemistry of (-) -5b was unequivocally determined to be 1
R, 2
R, 3
S by converting it to a known compound derived from (-) -limonen-10-ol. Starting with (-) -5b, a new route to the key intermediate ((-) -20) for the synthesis of 11- deoxyprostaglandins was established.
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FUMIKO ABE, TATSUO YAMAUCHI
1987 Volume 35 Issue 5 Pages
1748-1754
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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From the whole plant of
Trachelospermum asiaticum, sixteen triterpenoid glycosides wereisolated. Eight of them, including two known glucosides, suavissimoside Rl and the 3, 28-bis-
O-glucoside of 19α-hydroxyasiatic acid, were determined to be 28-
O-or 3, 28-bis-
O-glucosides of 19α-hydroxyursolic acid derivatives, except for one 28-
O-xylosyl-glucoside. The most major compound was the 28-
O-glucoside of 2α, 3β, 19α, 23, 24-pentahydroxyurs-12-en-28-oic acid.
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TETSUYA TAKEYA, TORU OKUBO, SEISHO TOBINAGA
1987 Volume 35 Issue 5 Pages
1755-1761
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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An approach for general synthesis of biphenyl neolignans by the reaction of 1-oxaspiro [4.5] -deca-6, 9-diene-2, 8-dione (3) (quinol-lactone) with the Grignard reagent 4 was explored. Among the biphenyl derivatives 6, 8, and 9 thus obtained, 6 was transformed to magnaldehyde B (2b) in three steps.
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TETSUYA TAKEYA, TORU OKUBO, EISHO TOBINAGA
1987 Volume 35 Issue 5 Pages
1762-1769
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Acid catalyzed condensation reactions of 1-oxaspiro [4.5] deca-6, 9-diene-2, 8-dion (1) (quinollactone) with phenols and phenol-ethers 2a-i to yield biphenyls 3a-i and 4a-f were found to proceed by an elimination-addition mechanism.
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ATSUKO NOSE, TADAHIRO KUDO
1987 Volume 35 Issue 5 Pages
1770-1776
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Aromatic sulfonyl chlorides were reduced with sodium borohydride in tetrahydrofuran at 0 C to the corresponding sulfinic acids in good yields. Further reduction proceeded when the reaction was carried out under reflux in tetrahydrofuran to give disulfide and thiophenol derivatives
via sulfinic acid. Furthermore, sulfonamides were reduced with sodium borohydride by heating directly to give sulfide, disulfide and thiophenol derivatives, and diphenyl sulfone was reduced under similar conditions to give thiophenol and biphenyl
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TAKASHI HARAYAMA, HIDETO FUKUSHI, TETSUYA ARATANI, KAZUHIRO OGAWA, TER ...
1987 Volume 35 Issue 5 Pages
1777-1784
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Treatment of 8, 8-dibromobicyclo [5.1.0] octanes (A) with a higher order organocuprate prepared from cuprous thiocyanate (method A) or cuprous cyanide (method B) and methyllithium, followed by the addition of methyl iodide
in situ, readily afforded 8, 8-dimethylbicyclo [5.1.0] octanes (B) in good yields. The results are summarized in Table I. Interestingly, reaction of the
cisdibromides (4 and 19) under the present conditions gave tricyclic compounds (15 and 16, and 20, respectively)
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TAKESHI DEYAMA, TAKAKO IKAWA, SHIZUKA KITAGAWA, SANSEI NISHIBE
1987 Volume 35 Issue 5 Pages
1785-1789
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Two new lignans,
erythro-dihydroxydehydrodiconiferyl alcohol (1) and its
threo isomer (2), were isolated from the bark of
Eucommia ulmoides OLIV. (Eucommiaceae), together with six known lignans and three known phenolic compounds. Their structures were elucidated on the basis of spectroscopic analyses and chemical evidence.
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YUTAKA OZAKI, KEIKO MOCHIDA, SANG-WON KIM
1987 Volume 35 Issue 5 Pages
1790-1795
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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A number of 4- (2-hydroxyalkyl) -1, 3-benzenediols (4) were synthesized by thermolysis of 1, 3-cyclohexadiones (3), which were obtained by the reaction of α-phenylsulfiny1-γ-butyrolactones (I) with α, β-unsaturated ketones (2), providing a new aromatic annelation. One of the compounds thus obtained, 4- (3, 4-dihydro-4-hydroxy-7-methoxy-2
H-1-benzopyran-3-yl) -1, 3-benzenediol (4n), was converted to isomedicarpin (5b) and homopterocarpin (5c).
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NORIICHI ODA, YUKIO YOSHIDA, SHIN-ICHI NAGAI, TAISEI UEDA, JINSAKU SAK ...
1987 Volume 35 Issue 5 Pages
1796-1800
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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2- [(2-Nitrophenyl) methylene] propanedioic acids (2a-c) were denitrocyclized to coumarins (3a-c) by heating in quinoline in the presence of copper powder. 2- (4-Methoxyphenyl) -3- (2-nitrophenyl) - (Z) -2-propenoic acids (6a, b, d, e) were also similarly denitrocyclized to 3-substituted coumarins (7a, b, d, e).
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TAKESHI DEYAMA, TAKAKO IKAWA, SHIZUKA KITAGAWA, SANSEI NISHIBE
1987 Volume 35 Issue 5 Pages
1803-1807
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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A new sesquilignan glycoside, syringylglycerol-β-syringaresinol ether 4' '4''', -di-Ο-β-D-glucopyraRoside (1), and a new neolignan glycoside, dehydrodiconiferyl alcohol 4, γ'-di-Ο-β-D-glucopyranoside (2), were isolated from the bark of Eucommia ulmoides Ouv. (Eucommiaceae), together with a known neolignan glycoside, citrusin B (3). Their structures were determined on the basis of chemical evidence and spectroscopic analyses.
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YUKARI SUZUKI, AKIRA MATSUDA, TOHRU UEDA
1987 Volume 35 Issue 5 Pages
1808-1811
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Oxidation of 6, 5'-cyclo-5'-deoxy-2', 3'-Ο-isopropylideneuridine with selenium dioxide gave the 5'-oxo derivative, which was converted to the 5'-ethoxycarbonylmethylidene derivative (3). Reduction of 3 afforded, after deprotection, the title compounds (6,
R and
S). The base-catalyzed epimerization of 6 at the 5'-position was observed, and the equilibrium was in favor of the (
R) -epimer.
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ZHUO-FENG XIE, YUKINOBU ICHIKAWA, HIROSHI SUEMUNE, KIYOSHI SAKAI
1987 Volume 35 Issue 5 Pages
1812-1816
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The conversion of (+) -limonen-10-ol (7) into the key intermediate for the synthesis of carbacyclin (1), (+) - (1
S, 2
R, 3
R, 5
R) -3-acetoxy-2-methoxycarbony1-7-oxobicyclo [3.3.0] octane (2), is described. The cis-3, 4-disubstituted cyclopentanone prepared from 7
via a sequence of reactions involving Rh (I) -catalyzed cyclization could be converted to the 3-acetylbicyclo [3.3.0] oct-2-ene skeleton, which was subjected to 1, 4-addition reaction with CN
-. The resulting cyano compound was transformed into the key intermediate 2 through appropriate modification of the substituents on the five-membered ring. This synthetic method provides a new route to carbacyclin.
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TAKASHI YOSHIDA, XIN-MIN CHEN, TSUTOMU HATANO, MAKOTO FUKUSHIMA, TAKUO ...
1987 Volume 35 Issue 5 Pages
1817-1822
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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From the unripe fruits of
Rosa roxburghii TRATT., two new hydrolyzable tannins, roxbin A (1) (a dimeric ellagitannin) and roxbin B (9), were isolated along with rugosin F (2), pedunculagin (3), casuarictin (4), alnusiin (5), stachyurin (6), tellimagrandin 11 (7), 2, 3-Ο- (
S) -hexahydroxydiphenoyl-D-glucose and (+) -catechin. The structures of new tannins were elucidated on the basis of chemical and spectral evidence.
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TAKAO SAKAMOTO, YOSHINORI KONDO, SHIGEKI IWASHITA, HIROSHI YAMANAKA
1987 Volume 35 Issue 5 Pages
1823-1828
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The palladium-catalyzed reaction of ethyl 2-bromocarbanilate with trimethylsilylacetylene yielded ethyl 2- (trimethylsilylethynyl) carbanilate, which was treated with sodium ethoxide to give indole. The carbanilates having a methyl or a bromo substituent were similarly transformed to corresponding indole derivatives. Furthermore, pyrrolo [3, 2-
b] -and pyrrolo [3, 2-
c] pyridines were synthesized by this method.
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YOSHINORI FUJIMOTO, TAKETOSHI YAMADA, NOBUO IKEKAWA, ICHIRO NISHIYAMA, ...
1987 Volume 35 Issue 5 Pages
1829-1832
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Three steroidal saponins (designated as Co-ARIS I, II, III) which are essential for inducing the acrosome reaction, were isolated from the egg jelly of the starfish,
Asterias amurensis, and their structures were elucidated by chemical and spectral means. The structure of Co-ARIS II was determined to be 6α-
Ο- {
Ο-β-D-fucopyranosyl- (1→2) -
Ο-β-D-fucopyranosyl- (1→4) - [
Ο-β-D-quinovopyranosyl- (1→2)] -
Ο-β-D-quinovopyranosyl- (1→3) -6-deoxy-β-D-
xylo-hexos-4-ulopyranos-1-yl} -3β-hydroxysulfonyloxy-5α-cholesta-9 (11), 17 (20), 24-trien-23-one (2), whereas Co-ARIS I (1) and Co-ARIS III (3) were identical with ovarian asterosaponin-1 (OA-1) and OA-4 previously isolated from the same species of starfish.
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FUMIKO ABE, TATSUO YAMAUCHI
1987 Volume 35 Issue 5 Pages
1833-1838
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Eight glycosides of 2α, 19α-dihydroxyoleanolic acid derivatives, includingtrachelosperosidesD-1, D-2, E-1, F-2, and arjungenin-23, 28-bis-
Ο-glucoside and-28-
Ο-xylopyranosyl- (1→2) -gluco-pyranoside, were isolated from the whole plant of
Trachelospermum asiaticum, along with the known glucosides arjunglucoside I and arjungenin-3, 28-bis-
Ο-glucoside, and their structures were determined.
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JUN MORI, SHIN-ICHI NAGAI, JINSAKU SAKAKIBARA, KAZUMI TAKEYA, YOSHIHIR ...
1987 Volume 35 Issue 5 Pages
1839-1846
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Catalytic hydrogenation of proscillaridin (I) gave five compounds (II-VI) which were successfully separated by reversed-phase high performance liquid chromatography. The structures of II-VI were determined on the basis of the proton, carbon-13 and two dimensional nuclear magnetic resonance (
1H-,
13C-and 2D-NMR) spectra. The configurations of IV and V were determined by circular dichroism spectral analyses.
Relationships between the chemical structures and biological activities of I-VI were studiedby the use of isolated guinea-pig papillary muscle and an Na
+, K
+-adenosine triphosphatase preparation from dog kidney. The biological activity of each compound was evaluated in terms of pD
2 and pIC
50 values, while the inotropic speed of each compound was evaluated in terms of
T50 value. The activities of the reduced compounds (II-VI) were weaker than that of proscillaridin (I), but the inotropic speeds were faster.
A significant correlation was obtained between the
13C-NMR chemical shifts of C-24 and the pD
2 values of I-VI (
r= 0.95,
p < 0.01). The
T50 values and
13C-NMR chemical shifts of C-18 also showed a remarkable correlation (
r=0.96,
p<0.01).
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SANAE MARUYAMA, NORIKO OGIHARA, ITSUKO ADACHI, JUNKO OHOTAWA, MASUO MO ...
1987 Volume 35 Issue 5 Pages
1847-1852
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Several 7-ketones of lanostane, 4, 4-dimethylcholestane and cholestane derivatives were subjected to catalytic hydrogenation on platinum, reduction with complex hydrides and reduction with sodium in
tert-butanol, and the product ratios (7α-ol/7β-ol) were determined by gas chromatography or high-performance liquid chromatography. Catalytic hydrogenation of 3β-hydroxylanostan-7-one and3β-hydroxy-4, 4-dimethylcholestan-7-one yielded the 7β-alcohols as the major products, whereas their 3-acetates gave principally the7a-alcohols. Reduction of various 7-ketones with sodium in
tert-butanol gave mainly the 7βequatorial alcohols, while the epimeric7α-ols were the major products on reduction with lithium tri-
sect-butylborohydride. The stereoselectivity of reduction with sodium borohydride and lithium aluminum hydride was highly dependent on the neighboring double bond and 4, 4-dimethyl and/or 14α-methyl substituent (s).
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KIMIYE BABA, KAZUO TAKEUCHI, MITSUNOBU DOI, MITSUGI KOZAWA
1987 Volume 35 Issue 5 Pages
1853-1859
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The structure of a novel spiro biflavonoid, daphnodorin C (3), previously isolated from the root and bark of
Daphne odora THUNB., was established on the basis of chemical and spectral studies, and confirmed by an X-ray diffraction analysis.
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1, 3-Oxazines and Related Compounds. XIII. Reaction of Acyl Meldrum's Acids with Schiff Bases Giving 2, 3-Disubstituted 5-Acy1-3, 4, 5, 6-tetrahydro-2H-1, 3-oxazine-4, 6-diones and 2, 3, 6-Trisubstituted 2, 3-Dihydro-1, 3-oxazin-4-ones
YUTAKA YAMAMOTO, YUKIYOSHI WATANABE, SHUHEI OHNISHI
1987 Volume 35 Issue 5 Pages
1860-1870
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The reactions of Schiff bases (2) with various acyl Meldrum's acids (1) were investigated. Refluxing of 1 and 2 in benzene caused an exchange reaction of the acetone moiety of 1 with the Schiff base moiety through the intermediate acylketenes 11 formed
in situ from 1 to give 2, 3-disubstituted 5-acy1-3, 4, 5, 6-tetrahydro-2
H-1, 3-oxazine-4, 6-diones (3). The oxazindiones 3 underwent thermal conversion to afford 2, 3, 6-trisubstituted 2, 3-dihydro-1, 3-oxazin-4-ones (4) in good yield. The intermediates 11 were found to be formed by thermal cleavage of both 1 and 3.
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YUTAKA YAMAMOTO, YUKIYOSHI WATANABE
1987 Volume 35 Issue 5 Pages
1871-1878
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Simple preparations of 2, 3, 6-trisubstituted 2, 3-dihydro-1, 3-oxazine-5-carboxylic acids (4) and 1, 4-disubstituted 3-acyl-β-lactams (5) from acyl Meldrum's acids and Schiff bases were carried out. 2, 3-Disubstituted 5-acy1-3, 4, 5, 6-tetrahydro-2
H-1, 3-oxazine-4, 6-diones (3) were isomerized to 4 in a chlorotrimethylsilane?triethylamine system and to 5 by hydrogen chloride.
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KATSUICHIRO KOMATSU, SETSUKO NAKAGAWA, HIDEAKI UMEYAMA, HARUKI NAKAMUR ...
1987 Volume 35 Issue 5 Pages
1880-1895
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The electrostatic interaction energies among dihydrofolate reductase (DHFR), coenzyme reduced nicotinamide adenine dinucleotide phosphate (NADPH) and methotrexate (MTX) were calculated by means of the Debye-Hückel equation taking the solvent accessibility into account; the results obtained were comparable with the experimental values. The atoms of guest molecules exposed on the molecular surface in NADPH and MTX may contribute to the electrostatic stabilization on the molecular complex formed with the host molecules. The electrostatic effects due to the replacement of charged amino acid residues with other ones or uncharged ones were visualized as the difference of two electrostatic correlation potentials by the use of computer graphics. It is shown that Arg43, Arg44, Arg57, and Asp26 of DHFR play important roles from the view point of electrostatic potential. A distance graphics method was used to express the distance from a patch on the van der Waals' surface of the guest molecule to the nearest host-molecular surface in order to visualize the buried ligand, and host-atom contacts with the guest atom are given as the contact ratio of the guest-atoms with the proper host atoms.
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SHOHGO ATARASHI, SHUICHI YOKOHAMA, KEN-ICHI YAMAZAKI, KATSU-ICHI SAKAN ...
1987 Volume 35 Issue 5 Pages
1896-1902
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Two optically active (100% enantiomeric excess) isomers (13a and 13b) of ofloxacin (1) [(±) -ofloxacin; DL-8280; (±) -9-fluoro-2, 3-dihydro-3-methyl-10- (4-methyl-1-piperazinyl) -7-oxo-7
H-pyrido [1, 2, 3-
de] [1, 4] benzoxazine-6-carboxylic acid] and their fluoromethyl derivatives (14a and 14b) were prepared
via their optically active intermediates resolved by use of high-performance liquid chromatography (HPLC). The isomers (13a and 13b) were also obtained efficiently by an alternative route
via separation of the diastereoisomers (18, 19) prepared in the reaction of benzoxazine (17) with L-prolinyl chloride.
The (-) -isomers of 1 and its fluoromethyl derivative (2) were approximately twice as active as the corresponding racemates, while the (+) -isomers were considerably less active than the racemates.
The absolute configuration at the C
3 position in the oxazine ring in a series of (-) -compounds (b) was confirmed by X-ray analysis of the hydrochloride of the (-) -benzoxazine derivative (15b) to be
S.
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NOBUHIRO OHI, BUNYA AOKI, TEIZO SHINOZAKI, KANZI MORO, TOSHIO KUROKI, ...
1987 Volume 35 Issue 5 Pages
1903-1909
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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New ureidocephalosporin and ureidocephamycin derivatives containing a catechol moiety or its acetate were prepared and their minimum inhibitory concentration values against various microorganisms were determined. Among these compounds, the ureidocephalosporins (2, 3Aa, 3Ba) and ureidocephamycins (4, 5) carrying a methyl group on the nitrogen atom of the ureido bond showed strong activities against
Pseudomonas aeruginosa. 7β- [(R) -2-[3- (3, 4-Dihydroxybenzoyl) -3-methylureido] -2-phenylacetamido] -7α-methoxy-3- [(1-methyl-1H-tetrazol-5-yl) -thiomethyl] -3-cephem-4-carboxylic acid (5) had the most potent activity
in vitro against gramnegative bacteria, its activity being 8-to 32-fold and 4-fold greater than those of cefoperazone and ceftazidime, respectively, against two strains of
P. aeruginosa. The structure-activity relationship is discussed.
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SHOJI SHIBATA, KUNIO TAKAHASHI, SHINGO YANO, MASATOSHI HARADA, HIROSHI ...
1987 Volume 35 Issue 5 Pages
1910-1918
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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18β-Olean-12-ene-3β, 30-diol (deoxoglycyrrhetol) (4a) was prepared with a view to eliminating pseudoaldosteronism, a side-effect of glycyrrhetinic acid (1b), which is the sapogenin of Licorice saponin, glycyrrhizin (1a), while maintaining or enhancing the therapeutic activities.
On reduction of the 11-keto and 30-carboxyl groups of 1b with NaAlH
2- (OCH
2CH
2OCH
3)
2, olean-12-ene-3β, 11β, 30-triol (9) and olean-12-ene-3β, 11α, 30-triol (10) were obtained. On catalytic hydrogenation of 9 and 10 with Pd-C as a catalyst, 4a was formed in an overall yield of 80%. On treatment with conc. HCl, 9 yielded 18β-olean-9 (11), 12-diene-3β, 30-diol (11a), while 10 yielded olean-11, 13 (18) -diene-3β, 30-diol (12a). Mono-and di-β-carboxy-propionyl and mono-and di-ο-pbthaloyl esters of 4a, lla and 12a were prepared to increase the hydrophilic character.
The competitive inhibition of 5β, Δ
4-reductase of corticosteroids in the liver which is caused by lb to induce pseudoaldosteronism was not observed in the case of 4a. Compounds 4a, 11a and 12a and their β-carboxypropionyl and ο-phthaloyl esters were studied pharmacologically, and showed antiulcerogenic, antiallergic and antiinflammatory activities.
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HIROSADA SUGIHARA, HIROSHI MABUCHI, YUTAKA KAWAMATSU
1987 Volume 35 Issue 5 Pages
1919-1929
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Methyl 3-oxo-3, 4-dihydro-2
H-1, 5-benzoxathiepin-4-carboxylates (3a-f) were synthesized by regioselective Dieckmann reaction of methyl 2-methoxycarbonylmethylthiophenoxyacetates (2a-f) [readily prepared from 2-mercaptophenols (la-f)] in fairly good yields. Alkylation of thc ketoester (3b) with alkyl halides gave 4-alkylated derivatives (7 and 8). A substituent at the 2-position on the 1, 5-benzoxathiepin ring was introduced by Dieckmann reaction of methyl ssubstituted 2-methoxycarbonylmethylthiophenoxyacetates (11, 12b and 12f). Thorpe-Ziegler reaction of 2-cyanomethylthiophenoxyacetonitriles (18a-d) gave 3-amino-2
H-1, 5-benzoxathiepin-4-carbonitriles (19a-d). Novel heterocycles, 4-amino-11
H-pyrimido [4, 5-
c] [1, 5] benzoxathiepin derivatives (24-32), were synthesized by the reaction of enaminonitriles (3a and 3b) with amidines or guanidines.
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HIROSADA SUGIHARA, HIROSHI MABUCHI, MINORU HIRATA, TETSUJI IMAMOTO, YU ...
1987 Volume 35 Issue 5 Pages
1930-1952
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Novel 1, 5-benzoxathiepin derivatives, 3, 4-dihydro-2
H-1, 5-benzoxathiepin-3-ols with an aminoalkyl group at the 2-, 3- or 4-position, were synthesized and evaluated for serotonin S
2-receptor-blocking activity and adrenergic α
1-receptor-blocking activity. Methyl 4-aminoalky1-3-hydroxy-3, 4-dihydro-2
H-1, 5-benzoxathiepin-4-carboxylates showed significant S
2-receptor-block-ing activities. Structure-activity relationships (including the results of a conformational study and skeletal modifications) were examined. In the series of 1, 5-benzoxathiepin, 1-benzoxepin and 1-benzothiepin derivatives, methyl cis-3-hydroxy-7-methoxy-4- [3- (4-phenyl -1-piperazinyl) propyl] -3, 4-dihydro-2
H-1, 5-benzoxathiepin-4-carboxylatehydrochloride (CV-5197) showed the most potent and the most selective S
2-receptor-blocking activity in the binding profile, and was chosen as a candidate for further pharmacological evaluation.
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HIROYUKI NATE, YASUO SEKINE, YASUSHI HONMA, HIDEO NAKAI, HIROSHI WADA, ...
1987 Volume 35 Issue 5 Pages
1953-1968
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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A series of novel 2-phenylthiazolidine-3-thiocarboxamides (II) was synthesized and tested for positive inotropic activity in the isolated guinea pig heart and in anesthetized dogs. Reaction of the benzaldehydes (VI, XI, XIV and XV) with cysteamine followed by treatment with isothiocyanates readily gave II. Structure-activity relationships were investigated by varying the structural parameters.
N-Methyl-2 -phenylthiazolidine-3-thiocarboxamides having an
ortho substituent such as a Me or OMe group exhibited significant positive inotropic action, which was not blocked by propranolol. Among the various
ortho-alkoxyphenyl derivatives synthesized, the 2- (2- (3- (4-phenylpiperazino) propoxy) phenyl) derivative (I
67) was found to exhibit more potent and longerlasting activity than amrinone without any significant effect on heart rate or blood pressure
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TOSHIO MIYASE, MAYUMI YAMADA, SEIGO FUKUSHIMA
1987 Volume 35 Issue 5 Pages
1969-1974
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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A new guaiane-type sesquiterpene, prenanthelide A (1), and three new guaiane-type sesquiterpene glycosides, prenanthesides A (3), B (4) and C (7), have been isolated from
Prenanthes acerifolia BENTH., together with three known guaiane-type sesquiterpene glycosides, ixerin D (2), 8-epidesacylcynaropicrin glucoside (5) and crepiside E (6). The structures of the new compounds were established on the basis of chemical and spectral data.
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HISAKATSU IWABUCHI, MASAHIRO YOSHIKURA, YOSHITOMI IKAWA, WASUKE KAMISA ...
1987 Volume 35 Issue 5 Pages
1975-1981
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Two sesquiterpene alcohols, panasinsanol A (1) and panasinsanol B (2), were isolated from the rootlets of
Panax ginseng C. A. MEYER (Araliaceae) together with known sesquiterpene hydro-carbons, α-panasinsene (3), β-panasinsene (4), α-neoclovene (5), and β-neoclovene (6). The structures of 1 and 2 were established by spectral evidence, chemical correlations to congener hydrocarbons (3, 4, 5, and 6), and finally by their syntheses from (-) -β-caryophyllene. This is the first isolation of 1 from a natural source, and 2 is a novel panasinsane-type sesquiterpene.
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TAKAO KONOSHIMA, MUTSUO KOZUKA, TAKEATSU KIMURA
1987 Volume 35 Issue 5 Pages
1982-1990
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Four new triterpenoid saponins, gymnocladus saponins F
2 (1), F
1 (2), E (3) and D
1 (4), were isolated from the fruits of
Gymnocladus chinensis BAILLON. On the basis of chemical and physicochemical evidence, they were characterized structurally as 3, 28-bisglycosides of 2β, 23-dihydroxyacacic acid having a glycosyl monoterpene carboxylate as an acyl moiety.
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KIYOSHI ZAITSU, MIKIO OHNISHI, HIROYUKI HOSOYA, HIROYUKI SUGIMOTO, YOS ...
1987 Volume 35 Issue 5 Pages
1991-1997
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Five heterobifunctional reagents,
N- (bromoacetamido-
n-alkanoyloxy) succinimides having a glycine or ω-amino acid (β-alanine, γ-aminobutyric acid, δ-aminovaleric acid or ε-aminocaproic acid) residue, were synthesized. Bromoacetamido-
n-alkanoyl groups could be introduced into horseradish peroxidase and hen egg-white lysozyme and its reduced and S-3- (trimethylated amino) propylated product by using the reagents. The number of bromoacetamido-
n-alkanoyl groups introduced into the proteins could be successfully estimated from the amount of glycine or ω-amino acid (non-protein amino acid) produced from the introduced groups by acid hydrolysis.
N- (β-Bromoacetamido-
n-propionoyloxy) succinimide, one of the reagents, was examined as a reagent for the preparation of horseradish peroxidase-insulin conjugate. A single β-bromoacet- amido-n-propionoyl group was first introduced into Gly
A1, Phe
B1-dicitraconylinsulin through the ε-amino group of its Lysine
B29 residue and the product was subjected to decitraconylation with dilute acetic acid to obtain Lys
B29- (β-bromoacetamido-
n-propionoyl) insulin. The insulin was reacted with thiolated horseradish peroxidase to give peroxidase-insulin conjugate (molar ratio of 1 : 1).
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TERUAKI AKAO, KYOKO MIBU, TATSUO ERABI, MASAO HATTORI, TSUNEO NAMBA, K ...
1987 Volume 35 Issue 5 Pages
1998-2003
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Reduced flavin-adenine dinucleotide (FADH
2), which was produced by flavin-adenine dinucleotide (FAD) -dependent sennidin reductase, reduced methyl orange non-enzymatically in a molar ratio of 2 : 1 under anaerobic conditions. Similarly, sennidins and sennosides were reduced nonenzymatically to rheinanthrone and 8-glucosylrheinanthrone, respectively, by the reduced forms of cofactors such as FAD, flavin mononucleotide (FMN), riboflavin and benzyl viologen. The reaction was inhibited by oxygen. FADH
2 reduced sennidins equimolarly, but sennosides were reduced much less effectively than sennidins (about one-tenth).
The polarographic half-wave potentials of sennidins A and B, and sennosides A and B were-115, -133, -184and-201mV, respectively.
Therefore, it was confirmed that the reduction of sennidins and sennosides by FAD-dependent sennidin reductase consists of the following two reactions; (1) the reductase reduces cofactors such as FAD and (2) sennidins and sennosides are reduced non-enzymatically by the reduced forms of cofactors.
On the other hand, oxidation of rheinanthrone to sennidins in a neutral solution occurred with oxygen but not with FAD.
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TOSHIYUKI MASUZAWA, TADAYORI SHIMIZU, YASUTAKE YANAGIHARA, ICHIJI MIFU ...
1987 Volume 35 Issue 5 Pages
2004-2010
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The macrophage activation and immunostimulating effects of the slime of
Sphaerotilus natans IAM 12068, which is an aquatic sheathed bacterium, and GF-P-1, which was isolated from the slime fraction by Sepharose 4B gel filtration and has antitumor activity against Ehrlich ascites tumor in mice, were investigated. C57BL/6 mice peritoneal exudate macrophage induced by GF-P-1, which exhibited more effective antitumor activity than slime fraction, had the strongest cytostatic activity against EL-4 leukemic cells
in vitro. Addition of GF-P-1 to mouse peritoneal macrophages
in vitro caused marked spreading morphology, but the slime fraction did not. Acid phosphatase activity in the peritoneal cells induced by slime and GF-P-1 was also augmented as compared with that of resident macrophages.
S. natans fractions, as well as
Salmonella typhimurium lipopolysaccharide, were able to induce the mitogenic response in cultured spleen cells of C57BL/6 mice. Since spleen cells pretreated with rabbit anti-mouse thymocyte antiserum showed an unaffected mitogenic response to slime, the slime may be aB-lymphocyte mitogen. When slime fraction and GF-P-1 were injected intraperitoneally into ddY mice, they exhibited an enhancing effect onantibody response
in vivo. These results indicate that slime and GF-P-1 are able to activate macrophages and exhibit immunostimulating effects.
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SADAKI FUJIMOTO, MAYUMI TAKEBAYASHI, NAOKO KAWAMOTO, AKIRA OHARA
1987 Volume 35 Issue 5 Pages
2011-2015
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Mn (III) -acid phosphatase [EC 3.1.3.2] from sweet potato was inactivated by diethylpyrocarbonate (DEPC) in the presence of the F
- ion.Upon treatment of the inactivated enzyme with NH2OH, the enzyme activity was significantly restored. The difference absorption spectra of the modified vs. native enzyme preparations, both in the presence and absence of the F
- ion, exhibited two prominent peaks at around 242 and 275 nm.The pH-dependence of the inactivation rate suggested that an amino acid residue having a p
K value of approximately 7.3 was involved in the inactivation. These results indicate that the inactivation was due to the modification of histidine residues. The correlation between the spectral change at 242 nm and the activity change of theenzyme in the presence and absence of the F
- ion revealed that 1 histidine residue per subunit was essential for the enzyme activity. The inactivation by DEPC occurred only in the presence of the F
- ion, which has been found to interact with the Mn in the active site, suggesting that the histidine residue to be modified is located at the activesite of the enzyme.
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TAKASHI ABIKO, HIROSHI SEKINO
1987 Volume 35 Issue 5 Pages
2016-2024
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The nonatetracontapeptide corresponding to the revised amino acid sequence of thymopoietin II was synthesized by assembling ten peptide fragments in solution followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole (molar ratio, 1 : 1) in trifluoroacetic acid in the presence of dimethylselenide and
m-cresol. The synthetic nonatetracontapeptide was tested for effect on impaired T-lymphocyte transformation by phytohemagglutinin (PHA) in a uremic patient with pneumonia. The synthetic peptide was found to have restoring activity on the impaired PHA stimulation of T-lymphocytes; the minimum effective concentration was 1 μg/ml.
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MASAYOSHI YAMAGUCHI, HIROSUKE SHIBANO
1987 Volume 35 Issue 5 Pages
2025-2029
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The effect of a calcium-binding protein (CaBP) isolated from rat liver cytosol on enzyme activation by Ca
2+ was investigated. Pyruvate kinase (adenosine triphosphate : pyruvate 2-
Ο- phosphotransferase; EC 2.7.1.40) isolated from liver cytosol was activated by addition of Ca
2+ in the range of 1.0-10
3 μm; the concentration giving a half-maximal effect was 10 μm Ca
2+. The enzyme activation by 10 μm Ca
2+ addition was reversed by the presence of CaBP (4-40 μg/ml). With increasing concentrations of Ca
2+ (1, 10 and 100, um Ca
2+), the pyruvate kinase activity increased progressively. The increase of the enzyme activity by Ca
2+ was clearly prevented by the presence of CaBP (20 μ/ml). CaBP had no effect on pyruvate kinase activity in the absence of Ca
2+. Meanwhile, calmodulin (2.5-10 μg/ml) also reversed the activation of pyruvate kinase by Ca
2+ (1 and 10 μM). These results indicate that CaBP may regulate the activation of pyruvate kinase by Ca
2+. In particular, a novel CaBP may play an important role in the regulation of the Ca
2+ effect on pyruvate kinase.
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FUJIO ICHIMURA, YOSHIHARU DEGUCHI, KOICHI YOKOGAWA, EMI NAKASHIMA
1987 Volume 35 Issue 5 Pages
2030-2037
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The effect of valproate on the plasma concentration of phenytoin was examined in bothnormal and D-galactosamine-treated rats. In normal rats the total plasma concentration of phenytoin decreased and the plasma concentration of unbound phenytoin increased after the injection of valproate (300 mg/kg). By contrast, in rats showing low binding as a result of D-galactosamine treatment, the total and unbound concentrations of phenytoin in plasma were almost unchanged after the injection of valproate. Possible mechanisms to explain the above results are discussed in this paper on the basis of the results of plasma protein binding and tissue distribution studies. One such possible mechanism was thought to be that decrease in the total plasma concentration of phenytoin after valproate injection in normal rats may have resulted from an increased volume of distribution which is dependent on increase in the unbound fraction of phenytoin in plasma. On the other hand, one possible reason why valproate produced no significant influence on the total and unbound concentrations of phenytoin in plasma in the rats showing low binding may have been an unchanged volume of distribution of phenytoin preceding and following the injection of valproate which would have been dependent on the lack of change in the unbound fraction. The molar ratio of nonesterified fatty acid (NEFA) /albumin of the plasma protein was increased by D-galactosamine treatment. As NEFA is considered to be an important inhibitor of phenytoin binding to rat plasma, it could be speculated that valproate does not act as an inhibitor of phenytoin binding in rat plasma when the NEFA/albumin molar ratio of plasma protein is increased.
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EITARO ARAKAWA, SHIKIFUMI KITAZAWA
1987 Volume 35 Issue 5 Pages
2038-2044
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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In an attempt to develop a suitable dosage form of systemically acting drugs for pulmonary administration, the absorption of xanthine derivatives from the lung of rats was studied. The pulmonary absorption of xanthine derivatives was rapid, and these drugs were transferred into the circulation. For example, in the case of theophylline (500 μg/rat), the absorption within 1 min was about 90%, and in the cases of aminophylline (500 μg/rat) and caffeine (1000 μg/rat), 96% and 97%, respectively. The maximum plasma levels in all cases were achieved within 30 s. The pulmonary absorption of these drugs was not affected by body weight or wet weight of lung. When the dose of these drugs was raised 10- to 15-fold, the amount of compound absorbed was directly proportional to the dose, the percentage absorption remaining constant. The pulmonary absorption of these drugs was not significantly different at pH between 6.4 and 8.4, but at pH 9.4, the absorption of theophylline and aminophylline was significantly decreased (
p<0.001), though the absorption of caffeine remained nearly constant. Comparison of the partition coefficients of these drugs indicated that the pulmonary absorption of xanthine derivatives depends on lipid solubility. The pulmonary absorption of theophylline was unaffected by changes of the osmotic pressure of drug solutions. These results suggest that the pulmonary absorption of xanthine derivatives can indeed occur very rapidly, and that the lung may afford a favorable route of administration to obtain a systemic effect of drugs.
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KENJI SAITO, FUMIO HOSOI, KEIZO MAKUUCHI, MASUMI KOISHI
1987 Volume 35 Issue 5 Pages
2045-2051
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Polymer-coated porous microspheres containing salicylic acid as a model drug were prepared by graft copolymerization by a pre-irradiation method using gamma rays. Methyl methacrylate (MMA), dimethylaminoethyl methacrylate (DM), and diethylaminoethyl methacrylate (DE) were used as monomers. Irradiated spheres were brought in contact with monomer solution containing the drug. The amount of salicylic acid entrapped increased linearly with increasing extent of graft polymerization of DM-MMA and DE-MMA. The amount of salicylic acid released was proportional to the square root of time, and diffusion of salicylic acid through solution-filled pores in the matrix was the rate-limiting step. The diffusion rate constant of salicylic acid increased with increasing content of amino ester in the graft copolymer.
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YI ZHAO, IRIS H. HALL, C. BRENT OSWALD, TOSHIO YOKOI, KUO-HSIUNG LEE
1987 Volume 35 Issue 5 Pages
2052-2061
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The antimalarial agent, artesunate has been observed to suppress the infection growth rate of
Plasmodium berghei in CF
1 mouse red blood cells. The inhibition of growth was due to a number of biochemical mechanisms. Deoxyribonucleic acid (DNA) synthesis in the
Plasmodium berghei was inhibited significantly by the drug with marginal inhibition of protein synthesis. The inhibition of DNA synthesis seemed to be due to a block of purine synthesis at the regulatory enzyme site of inosine monophosphate (IMP) dehydrogenase. Whereas there was no evidence to demonstrate that the drug alkylated nucleotide bases or caused cross linking of DNA strands of the plasmodium, the drug did appear to cause non-specific binding to bases that interfered with template activity. There was marked inhibition of messenger ribonucleic acid (mRNA) polymerase activity with moderate inhibition of DNA polymerase activity. The drug caused significant reduction of basal oxygen consumption of
Plasmodium berghei with a significant inhibition of succinic acid dehydrogenase activity. The drug interacted with reduced nicotinamide adenine dinucleotide (NADH), suggesting the possibility that artesunate may interfere with energy required for cell growth.
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HIDEAKI TANIMORI, KENSEI YOSHIDA, HIDEAKI MOTOMURA, KAZUHIRO KITADA, S ...
1987 Volume 35 Issue 5 Pages
2062-2070
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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Affinty purification procedures for antibodies specific to a drug and to a carrier protein were examined in detail with the use of three enzyme immunoassays (EIAs). Many blasticidin S (BLS) molecules were coupled to an affinity ligand with pig serum albumin as a spacer protein. The influence of the spacer on the affinity purification of an antibody specific to BLS was quantitatively analyzed. The antibody showed higher binding to BLS bound to the solid matrix with a carrier protein than without. The stability of specific antibody in six representative eluents, used for affinity chromatography of specific antibodies, was examined, and 0.1 M potassium chloride-0.008 N hydrochloric acid buffer was selected as the preferred eluent based on the stability of the specific antibody and convenience in handling. The ability of the buffer to elute the specific antibody from an affinity column was studied, and was improved by modifying the concentration of potassium chloride in the buffer to 0.3 M. Complete purification of anti-BLS antibody was performed by affinity chromatography under the chosen conditions. The specific anti-BLS and anti-carrier protein antibodies were purified quantitatively. Formation of denatured specific antibody was hardly detected by a sensitive ETA, under the chosen conditions. The purity of the standard antiBLS antibody was demonstrated by the affinity chromatographic method with the aid of two EIAs for rabbit immunoglobulin G and for BLS.
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MASAHIKO IKEKITA, TAKUJI MASUNAGA, KAZUYUKI KIZUKI, HIROSHI MORIYA
1987 Volume 35 Issue 5 Pages
2071-2078
Published: May 25, 1987
Released on J-STAGE: October 19, 2009
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The patterns of micro-heterogeneity in relation to the carbohydrate structures of active-and latent-types of normal human urinary kallikrein (HUK) were analyzed by serial lectin agarose chromatographies (concanavalin A- erythroagglutinating phytohemagglutinin-, lentil lectin-and wheat germ agglutinin-agarose chromatographies) and crossed affino-immunoelectrophoresis. In the case of active HUK, the species carrying tri- and/or tetra-antennary oligosaccharide (s), corefucosylated bi-antennary oligosaccharide (s), and bi-antennary oligosaccharides containing outer galactose residues and an
N-acetylglucosamine residue linked β1, 4 to a β-linked mannose residue (bisecting
N-acetylglucosamine residue) amounted to approximately 36, 33 and 17% of the total active-type HUK, respectively. The micro-heterogeneity of the latent-type HUK found by serial lectin affinity chromatographies was similar to that of the active-type HUK.
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