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Volume 33, Issue 10
Displaying 1-50 of 74 articles from this issue
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YESOOK KIM, MIYAKO MATSUMOTO, KATSUNOSUKE MACHIDA1985 Volume 33 Issue 10 Pages 4125-4131
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe displacement velocity of each crystalline face of aspirin on dissolution in distilled water was determined by using large single crystals grown from ethanolic solution. It was found that each crystalline face of aspirin has its own displacement velocity. The specific surface energies for those crystalline surfaces in water and in vacuo were calculated from a set of atom-atom pairwise potential functions. The relative rate of diminution of surface area on dissolution of the crystal can be correlated to the sensitivity of the surface energy to the polarity of the solvent.View full abstractDownload PDF (706K) -
HIROSHI FURUKAWA, TIANSHUNG WU, TOMOKO OHTA, CHANGSHENG KUOH1985 Volume 33 Issue 10 Pages 4132-4138
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThirteen carbazole alkaloids were isolated from Murraya euchrestifolia HAYATA (Rutaceae) collected in Taiwan. Four of them are novel carbazolequinones [murrayaquinone-A (7), -B (8), -C (9), and -D (10)], isolated for the first time from natural sources. Three of others are new alkaloids having the normal carbazole nucleus [murrayafoline-A (1), -B (2), and (+)-murrayazoline (11)]. These structures were elucidated from spectral data and chemical transformations.View full abstractDownload PDF (782K) -
HISASHI ISHII, YUHICHIRO ICHIKAWA, ERI KAWANABE, MUNEKAZU ISHIKAWA, TS ...1985 Volume 33 Issue 10 Pages 4139-4151
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral nonphenolic benzo [c] phenanthridine alkaloids including naturally occurring nitidine (1a) and avicine (1e) were synthesized in excellent yields through an efficient synthetic method developed by us. Antitumor activities of twelve alkaloids including four naturally occurring O5-alkaloids [chelilutine (1g), chelirubine (1h), sanguilutine (1k), and sanguirubine (11)] against Sarcoma 180 were tested. The structure-activity relationship of these alkaloids is discussed.View full abstractDownload PDF (1336K) -
EIKO OHTSUKA, JITSUHIRO MATSUGI, AKIO YAMANE, HIROSHI MORIOKA, MORIO I ...1985 Volume 33 Issue 10 Pages 4152-4159
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRibooligonucleotides (nonamer, decamer and nonadecamer) were synthesized by the solid phase phosphotriester method using 2'-O-tetrahydrofuranyl nucleosides. These oligomers were designed in order to obtain E. coli tRNAMetf deficient in D-loop and D-stem and its analogs. Condensation was performed by using dimer blocks and the dimethoxytrityl group on the 5'-hydroxyl group was removed selectively by 1M ZnBr2 without affecting the 2'-protection.View full abstractDownload PDF (1285K) -
CHIKARA KANEKO, NOBUYA KATAGIRI, KEIJI UCHIYAMA, TORU YAMADA1985 Volume 33 Issue 10 Pages 4160-4166
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIrradiation (350nm) of 2-(3-butenyl)-and 2-(4-pentenyl) isoquinolin-1 (2H)-ones (1a and 1b) afforded the intramolecular [2+2] adducts (2a and 2b). The additions proceeded regioselectively to give only the parallel adducts. Though stable to irradiation at 350nm, these adducts (2a and 2b) gave o-vinylbenzamide derivatives (3a and 3b) on irradiation at 300nm. The intermolecular [2+2] adducts (7d and 7e) obtained by irradiation (≥300nm) of isoquinolin-1 (2H)-one (6) in the presence of a large excess of alkenes were also found to be unstable and reverted to the original components [isoquinolin-1 (2H)-one (6) and alkenes] on irradiation at 300nm in the absence of the alkenes.View full abstractDownload PDF (742K) -
KOUJI MORI, MASAFUMI GOTO, TOMOYA SAKAI1985 Volume 33 Issue 10 Pages 4167-4174
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxygenated dimer (2a) of 3-methylindole, which was isolated from the reaction mixture obtained by oxygenation of 3-methylindole in the presence of N, N'-(cis-1, 2-cyclohexylene) bis (3-tert-butylsalicylideneaminato) cobalt (II) in chloroform, was shown to be the stereoisomer of 5aβ (H), 11aα (H)-12β-hydroxy-10bβ, 12α-dimethyl-5a, 10b, 11a, 12-tetrahydro-6H-oxazolo [3, 2a : 4, 5-b'] diindole (1a) with inverted configuration at the C12 atom, on the basis of 1H and 13C-nuclear magnetic resonance (NMR) spectroscopic and chemical evidence. Kinetic parameters of restricted rotation about the amide bond in N-acetylated derivatives of 1a and 2a calculated from their dynamic NMR spectra were ΔH≐̸298=20.2±0.2 and ΔS≐̸298=+7.8±0.5 for the former, and ΔH≐̸298=19.7±0.2kcal mol-1 and ΔS≐̸298=+5.9±0.6cal K-1mol-1 for the latter. Acid decomposition of both dimers, 1a and 2a, afforded 3, 3'-dimethyl-1-(2'-indolyl)-oxindole, resulting from ring cleavage at the ether bond followed by dehydration.View full abstractDownload PDF (770K) -
TOSHIKO SATAKE, TAKAO MURAKAMI, NOBUAKI YOKOTE, YASUHISA SAIKI, CHIUMI ...1985 Volume 33 Issue 10 Pages 4175-4181
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel pterosin-type dinorsesquiterpene, mukagolactone (I), was isolated from the fronds of Monachosorum arakii TAGAWA (Pteridaceae), along with three new dinorsesquiterpene dimers, monachosorins A (II), B (III) and C (IV). Their structures were elucidated on the basis of spectroscopic and chemical data. Compound II may have been formed by an aldol-type condensation of 6-(2-hydroxyethyl)-5, 7-dimethylindan-1-one and the corresponding 5-formyl compound. The reduction of II afforded III, and the acid isomerization of II gave IV.View full abstractDownload PDF (819K) -
HIROSHI WADA, TOSHIKO SATAKE, TAKAO MURAKAMI, TOSHINORI KOJIMA, YASUHI ...1985 Volume 33 Issue 10 Pages 4182-4187
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fronds of Alsophila spinulosa TRYON biflavonoids Hegoflavone A (I) and B (II) were isolated and their structures were elucidated by spectroscopic analysis and chemical degradation to be 2, 3-dihydro-3'''-hydroxy-6, 6'''-biapigenin (I) and 2, 3-dihydro-6, 6'''-biluteolin (II) respectively. These are the first reports of a C-6/C-6'''-linked biflavonoid in nature.View full abstractDownload PDF (659K) -
ZHUANGXIN ZHANG, JUN ZHOU, KOJI HAYASHI, HIROSHI MITSUHASHI1985 Volume 33 Issue 10 Pages 4188-4192
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical components of the Chinese crude drug "Pai-Wei, " dried root of Cynanchum atratum BUNGE, have been further investigated. Glaucogenin-A (1), glaucoside-C (2), glaucoside-H (3) and a new glycoside named cynatratoside-F (4) were isolated. The structure of 4 was determined on the bases of spectroscopic evidence and analyses of its hydrolysate.View full abstractDownload PDF (549K) -
TAKEO HIGASHINO, MASUMI TAKEMOTO, KENICHI TANJI, CHIHOKO IIJIMA, EISAK ...1985 Volume 33 Issue 10 Pages 4193-4201
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 2-aroylquinoxalines (1) with sodium hydroxide in dimethyl sulfoxide (DMSO) was found to result in aryl migration, fission of the C2-C=O bond, and addition of DMSO to the C=O group, giving 2-arylquinoxalines (2), quinoxaline (4), aroic acids (5), and α-aryl-α-(methylsulfinylmethyl)-2-quinoxalinemethanols (6). Compounds 6 could be separated into two racemates, (αR*, SR*)-6 and (αR*, SS*)-6. In order to establish the generality of the aryl migration, other aroylated aromatic heterocycles were examined. 3-Aroylpyrido [2, 3-b] pyrazines (7) and 1-benzoyl-4-isoquinolinecarbonitrile (10) both underwent similar aryl migration to give 3-arylpyridopyrazines (14) and 1-phenyl-4-isoquinolinecarbonitrile (18), respectively. On the other hand, the reaction of 1-benzoylisoquinoline (9) and 2-benzoylquinoline (11) resulted not in migration, but in the addition of DMSO to give 1-isoquinolinemethanol (16) and 2-quinolinemethanol derivatives (20), respectively. In the case of 1-benzoylphthalazine (8), migration did not occur, but instead 4-benzoyl-1 (2H)-phthalazinone (15) was formed.View full abstractDownload PDF (861K) -
TAKESHI IMANISHI, NORIYUKI YAGI, MIYOJI HANAOKA1985 Volume 33 Issue 10 Pages 4202-4211
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new elaboration method for the 2-azabicyclo [2.2.2] octane ring via an intramolecular Michael reaction has been developed and applied to the total synthesis of (±)-ibogamine (1) and (±)-epiibogamine (2). The unsaturated ester (9) derived from ethyl 1, 6-dihydro-3 (2H)-pyridinone-1-carboxylate (3a) was reacted with potassium carbonate or sodium hydride to provide two 2-azabicyclo [2.2.2] octanone derivatives (19 and 20), the stereochemistry of which was confirmed by chemical evidence. By a three-step sequence, the esters (19 and 20) were converted into 27 and 36, which were then transformed into the corresponding amides (31 and 40). Cyclization of 31 and 40 followed by reduction with a complex of lithium aluminum hydride-aluminum chloride furnished (±)-epiibogamine (2) and (±)-ibogamine (1), respectively, in good yields.View full abstractDownload PDF (1048K) -
KOSAKU HIROTA, YUKIO KITADE, TETSUO TOMISHI, YOSHIFUMI MAKI1985 Volume 33 Issue 10 Pages 4212-4215
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 5-substituted 2', 5'-dichloro-2', 5'-dideoxyuridines (1a-d) with methanolic sodium hydroxide under reflux afforded the corresponding 5-substituted 2', 5'-anhydro-1-β-D-arabino-furanosyluracils (3a-d) in high yield. On the other hand, reaction of 5-substituted uridines (5a-d) with the Vilsmeier-Haack reagent (POCl3/DMF) followed by treatment with methanolic sodium hydroxide under reflux led directly to the formation of the corresponding anhydrouridines (3a-d) in good yield.View full abstractDownload PDF (489K) -
KOSUKE KAWADA, OSAMU KITAGAWA, TAKEO TAGUCHI, YUJI HANZAWA, YOSHIRO KO ...1985 Volume 33 Issue 10 Pages 4216-4222
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLewis acid-catalyzed aldol condensation of 2-trimethylsilyloxy-4-trifluoromethylfuran (2a) with aldehydes was found to proceed in a regio- and diastereoselective manner to give the 5-substituted 4-trifluoromethyl-2 (5H)-furanone (4) in good yield. The aldol product (4a) derived from benzyloxyacetaldehyde was successfully converted to the branched sugar (12), the first reported example of a trifluoromethylated branched sugar, and its crystal structure was determined by X-ray analysis.View full abstractDownload PDF (715K) -
TOSHIO YOKOI, TETSURO SHINGU, SHIGETOSHI KADOTA, TOHRU KIKUCHI1985 Volume 33 Issue 10 Pages 4223-4227
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPachysana-16, 21-diene-3β, 28-diol and pachysan-16-ene-3β, 28-diol, new triterpene-diols having a 28-nor-16-methylfriedelane skeleton, were isolated from Pachysandra terminalis SIEB. et ZUCC. and their structures were elucidated. The name "pachysanane" is proposed for this new skeleton.View full abstractDownload PDF (585K) -
KOJI KOBAYASHI, SHINICHI UESATO, SHINICHI UEDA, HIROYUKI INOUYE1985 Volume 33 Issue 10 Pages 4228-4234
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAdministration of 3H- or 13C-labeled acyclic monoterpenes to Gardenia jasminoides f. grandiflora cell suspension cultures showed that tarennoside (20) and gardenoside (21) were biosynthesized in the cell cultures via the cyclization of 10-oxogeranial (5a)/10-oxoneral (5b) to iridodial cation (14). followed by extensive randomization of the carbon atoms 3 and 11. Furthermore, the intermediacy of (R)-(+)-and (S)-(-)-10-hydroxycitronellol (24a, 24b) and (R)-(+)-and (S)-(-)-9, 10-dihydroxycitronellol (28a, 28b) was disproved.View full abstractDownload PDF (755K) -
YASUYUKI KITA, OSAMU TAMURA, HITOSHI YASUDA, FUMIO ITOH, YASUMITSU TAM ...1985 Volume 33 Issue 10 Pages 4235-4241
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of alkyl phenyl sulfoxides (2a-h) with O-methyl-O-tert-butyldimethylsily ketene acetal (1a) in dry acetonitrile in the presence of a catalytic amount of zinc iodide caused a Pummerer-type rearrangement to give α-siloxy phenyl sulfides (3a-h) under mild conditions. On the other hand, treatment of the sulfoxide (2d) with O-methyl-O-trimethylsilyl ketene acetals (1b, c) under similar conditions gave carbon-carbon bond-formed products, methyl 3-(phenylthio)-butyrates (8 and 9).View full abstractDownload PDF (691K) -
JEANCHARLES LANCELOT, DANIEL LADUREE, MAX ROBBA1985 Volume 33 Issue 10 Pages 4242-4246
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of 2-methyl-pyrido [3, 2-e] pyrrolo [1, 2-a] pyrazine is described. The starting materials, 2-amino-6-methyl-3-nitropyridine and 2-amino-6-methyl-3-hydroxypyridine, were converted into pyrrolyl derivatives by using 2, 5-dimethoxytetrahydrofuran in glacial acetic acid. Subsequent elaboration of the latter afforded the title compounds. The proton nuclear magnetic resonance (1H-NMR) spectra of the products were also studied.View full abstractDownload PDF (601K) -
SHIGEKI SASAKI, MOTOJI KAWASAKI, KENJI KOGA1985 Volume 33 Issue 10 Pages 4247-4266
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe rates of transacylation were studied between thiol-bearing chiral crown ethers (1-10) and α-amino acid p-nitrophenyl ester salts. Enantioselectivities, kD/kL ratios, of 6.5 for valine ester salt, 8.7 for phenylalanine ester salt, and 7.7 for valine ester salt were achieved by 1, 5, and 8, respectively. Saturation phenomena of rate acceleration depending on crown concentration were observed and analysis of these data revealed that the chiral recognition occurs in the step of liberation of p-nitrophenol by intra-complex thiolysis, not in the complex-forming step. A possible mechanism for the enantioselectivity is proposed on the basis of the kinetic data.View full abstractDownload PDF (2152K) -
MASAYUKI YOSHIKAWA, HUIKANG WANG, HIROSHI KAYAKIRI, TOSHIO TANIYAMA, I ...1985 Volume 33 Issue 10 Pages 4267-4274
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new bisdesmoside of soyasapogenol B (3), named sophoraflavoside I (2), was isolated together with soyasaponin I (1) from Sophorae Radix (Sophora flavescens AITON, root). By employing a photochemical cleavage method for the glucuronide linkage in 2 and on the bases of chemical reactions and spectral analyses, the structure of sophoraflavoside I has been determined to be 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl]-22-O-[β-D-glucopyranosyl (1→2)-α-L-arabinopyranosyl] soyasapogenol B (2).View full abstractDownload PDF (868K) -
TAKASHI TANAKA, OSAMU TANAKA, ZHONGWEN LIN, JUN ZHOU1985 Volume 33 Issue 10 Pages 4275-4280
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe assignment of the source plant of the Chinese plant drug "Bai-Yun-Shen" as Salvia digitaloides DIELS (Labiatae), was revised to Phlomis betonicoides DIELS of the same family. From roots of this plant, a sweet glycoside named phlomisoside-I (5) and a bitter glycoside named phlomisoside-II (6) were isolated. The aglycone of both compounds was proved to be baiyunol (7, furano-labdane-type diterpene), the aglycone of baiyunoside (1), which has already been isolated as the sweet principle from this plant drug. The structures of 5 and 6 were elucidated as the 3-O-α-rhamnopyranosyl-(1→2)-β-glucopyranoside and the 3-O-sophoroside of 7, respectively.View full abstractDownload PDF (669K) -
HIROSHI HOSODA, WATARU TAKASAKI, HIROYA MIURA, MASAHIRO TOHKIN, YUKO M ...1985 Volume 33 Issue 10 Pages 4281-4287
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA method for the conversion of 11-deoxycortisol into 3α-hydroxy-5α-compounds is described. The allotetrahydro-11-deoxycortisol monoacetates (8, 14), which are key intermediates in the preparation of the 3- or 21-glucuronide of allotetrahydro-11-deoxycortisol, were the target compounds. The preparation of 5α-dihydro-11-deoxycortisol 21-acetate (4) was carried out by hydrogenation of the 3-ethoxy-3, 5-diene (2), followed by acid hydrolysis. When the 21-tetrahydropyranyl ether (6) and 21-tert-butyldimethylsilyl ether (7) were treated with potassium tri-secbutylborohydride in tetrahydrofuran under mild conditions, selective reduction of the carbonyl group at C-3 took place, yielding the 3α-alcohols (9 and 10, respectively). Allotetrahydro-11-deoxycortisol 3-glucuronide (21) and allotetrahydro-11-deoxycortisol 21-glucuronide (23) were then prepared.View full abstractDownload PDF (861K) -
TOSHIO FUKAI, YOSHIO HANO, KAZUHIRO HIRAKURA, TARO NOMURA, JUN UZAWA1985 Volume 33 Issue 10 Pages 4288-4295
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new 2-arylbenzofuran derivative, mulberrofuran H and two isoprenylated flavones, kuwanons S and T, were isolated from the ethyl acetate extract of the root bark of cultivated mulberry tree (Japanese name "Roso, "a cultivated variety of Morus lhou KOIDZ.). The structures of mulberrofuran H and kuwanons S and T were shown to be 1, 2, and 3, respectively, on the basis of spectral evidence. Mulberrofuran H can be regarded biogenetically as a variation of a Diels-Alder type adduct of a chalcone derivative and a dehydroprenyl-2-arylbenzofuran derivative.View full abstractDownload PDF (766K) -
YUKIO MAEBAYASHI, MIKIO YAMAZAKI1985 Volume 33 Issue 10 Pages 4296-4298
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBiosynthetic incorporation of [1-13C]- and [1, 2-13C2] acetates into silvaticamide (1) was investigated in Aspergillus silvaticus. The incorporation experiments unambiguously demonstrate that silvaticamide is biosynthesized through the acetate-malonate pathway.View full abstractDownload PDF (355K) -
HIROKI TAKAHATA, TOMOKO NAKAJIMA, MASAHARU NAKANO, AKIRA TOMIGUCHI, TA ...1985 Volume 33 Issue 10 Pages 4299-4308
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of ketene-S, N-acetals (1-6), which are useful synthetic intermediates for heterocycles, with aryl isocyanates (7) is described. Annulation of 1-3 and 4-6 with 7 in boiling toluene gave bicyclic (8-10) and monocyclic (11-13) uracil derivatives, respectively. Addition of 2, 3, and 4 to 7 under mild conditions afforded the 1 : 1 adducts (18, 19, and 21), respectively. Compounds 18 and 19 also reacted with 7 to give bicyclic uracil derivatives.View full abstractDownload PDF (681K) -
HIROSHI YAMANAKA, MASAYUKI ANNAKA, YOSHINORI KONDO, TAKAO SAKAMOTO1985 Volume 33 Issue 10 Pages 4309-4313
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the presence of tetrakis (triphenylphosphine) palladium, 2-iodo-4, 6-dimethylpyrimidine and 4-iodo-2, 6-dimethylpyrimidine reacted with ethoxycarbonylmethylzinc bromide (Reformatsky reagent) to give ethyl 4, 6-dimethyl-2-pyrimidineacetate and ethyl 2, 6-dimethyl-4-pyrimidineacetate, respectively. In contrast, the reaction of 5-iodo-2, 4-dimethylpyrimidine with the same reagent resulted in recovery of the starting iodide. Similar results were observed in the reactions of various N-heteroaryl iodides.View full abstractDownload PDF (569K) -
TOZO FUJII, MASASHI OHBA1985 Volume 33 Issue 10 Pages 4314-4319
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe racemic synthesis of the Alangium lamarckii alkaloid 10-demethyltubulosine (2) has been accomplished for the first time via a "lactim ether route, "which included the intermediates (±)-7, (±)-8, (±)-10, and (±)-9. The 1'α-H isomers (±)-12 and (±)-11 were also obtained through this synthetic route. The assignments of the configuration at C-1'of (±)-2, (±)-9, (±)-11, and (±)-12 were based on four criteria, namely, the ratio of products from the catalytic reduction of (±)-10, thin-layer chromatographic mobility, and 1H and 13C nuclear magnetic resonance spectral features. The identity of synthetic (±)-2 with (-)-demethyltubulosine from A. lamarckii unequivocally established the structure of this alkaloid.View full abstractDownload PDF (651K) -
MASASHI TOMODA, RYOKO GONDA, NORIKO SHIMIZU, SACHIKO AKIYAMA, HITOMI A ...1985 Volume 33 Issue 10 Pages 4320-4325
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA representative mucilage, named Althaea-mucilage RL, was isolated from the leaves of Althaea rosea CAVAILLES. The final preparation was homogeneous as determined by ultracentrifugal analysis, electrophoresis, and gel chromatography. Its water solution gave an intrinsic viscosity value of 32. 5. It was mainly composed of partially acetylated acidic polysaccharide, and its molecular weight was estimated to be about 1800000. The polysaccharide was composed of L-rhamnose : D-galactose : D-galacturonic acid : D-glucuronic acid : O-acetyl groups in the approximately molar ratio of 20 : 1 : 16 : 16 : 10. Methylation and partial hydrolysis studies made it possible to deduce the structural features of the polysaccharide moiety in the mucilage.View full abstractDownload PDF (721K) -
NOBUTAKA FUJII, MITSUYA SAKURAI, SUZUMITSU KUNO, HARUAKI YAJIMA, MASAM ...1985 Volume 33 Issue 10 Pages 4326-4332
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAdrenorphin, H-Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH2, and its D-Met (O)2-analog were synthesized. In addition, analogs of [Arg6, Phe7] enkephalin substituted at the 2nd position by D-Ala and D-Met (O) were also synthesized, together with four other enkephalin analogs. Among these compounds, [D-Met (O)2] adrenorphin exhibited high analgesic activity (29.1 times that of morphine) antagonized by naloxone, when administered intracisternally to mice.View full abstractDownload PDF (815K) -
KIYOSHI TOMIOKA, TSUNEO ISHIGURO, KENJI KOGA1985 Volume 33 Issue 10 Pages 4333-4337
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOptically pure trans- and cis-burseran (4, 10) were stereoselectively synthesized in an unequivocal manner. Comparison of their behaviors on gas chromatography indicated that naturally occurring antitumor lignan, burseran, is the trans-isomer.View full abstractDownload PDF (595K) -
SATOSHI MORIMOTO, GENICHIRO NONAKA, ITSUO NISHIOKA1985 Volume 33 Issue 10 Pages 4338-4345
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA proanthocyanidin trimer (1), two tetramers (2 and 3) and a pentamer (4) have been isolated from the root bark of Cinnamomum sieboldii MEISNER (Lauraceae). The structures of these compounds were established by acid-catalyzed thiolytic degradation, in conjunction with proton and carbon-13 nuclear magnetic resonance analyses. In addition, the presence of (-)-epicatechin (13), (+)-catechin (14) and known proanthocyanidins B-1 (5), B-2 (6) and B-5 (7), trimers (8 and 9), tetramers (10 and 11) and a pentamer (12) in this plant was demonstrated.View full abstractDownload PDF (779K) -
HISAO ONA, SHOICHIRO UYEO, KIYOSHI MOTOKAWA, TADASHI YOSHIDA1985 Volume 33 Issue 10 Pages 4346-4360
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRacemic carbapenem antibiotics having a 1-(hydroxymethyl) ethylidene side-chain at C-6 [dl-asparenomycins A (54), B (37), C (53) and related compounds, 55, 56, 38, 59 and 45] were synthesized starting from the common intermediates 9a and 9b, and their antibacterial activities were examined. The synthesis involves transformation of a cyclic carbonate group into the 1-(hydroxymethyl) ethylidene moiety with a catalytic amount of 1, 8-diazabicyclo [5. 4. 0] undec-7-ene (DBU) in an appropriate solvent, and deblocking of the p-methoxybenzyl ester group by the AlCl3-anisole method.View full abstractDownload PDF (1610K) -
MITSURU IMUTA, HISAO ONA, SHOICHIRO UYEO, KIYOSHI MOTOKAWA, TADASHI YO ...1985 Volume 33 Issue 10 Pages 4361-4370
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRacemic 2-acetoxymethyl and 2-(heteroaromatic) thiomethyl carbapenems having a 1-(hydroxymethyl) ethylidene or cyclic carbonate side-chain at C-6 (5, 25, 38, 40, 42, and 36b, 23b, 28b, 30b, 32b, 34b) were synthesized from the common intermediates 3a and 3b, and their antibacterial activities were determined.View full abstractDownload PDF (1055K) -
MITSURU IMUTA, SHOICHIRO UYEO, MASAO NAKANO, TADASHI YOSHIDA1985 Volume 33 Issue 10 Pages 4371-4381
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRacemic and optically active 2-(heteroaromatic) thiomethyl penems having a 1-(hydroxymethyl) ethylidene or cyclic carbonate side-chain at C-6 (24, 51, 63, 65, 37, 40, 69 and 21b, 61b, 26b, 30b, 64b, 35b, 66b, 39b, 68b) were synthesized, and their antibacterial activities are determined.View full abstractDownload PDF (1177K) -
HISAO ONA, SHOICHIRO UYEO, TAKASHI FUKAO, MASAYOSHI DOI, TADASHI YOSHI ...1985 Volume 33 Issue 10 Pages 4382-4394
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRacemic 2-acetoxymethyl and 2-(heteroaromatic) thiomethyl carbapenem and penem antibiotics having a 1-(R*)-hydroxyethyl side-chain at C-6 (6, 7, 8, and 45, 59, 47, 49, 51) were synthesized, and their antibacterial activities were determined.View full abstractDownload PDF (1324K) -
GIULIANO BANDOLI, ANTONIO GRASSI, MARINO NICOLINI, GIUSEPPE C. PAPPALA ...1985 Volume 33 Issue 10 Pages 4395-4401
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe crystal and molecular structure of 4-hydroxy-2-oxo-1-pyrrolidineacetamide was determined by X-ray analysis. The molecular conformation found in the solid was compared with results of theoretical quantum mechanical calculations carried out by using an ab-initio method at the STO-3G level. Crystals (orthorhombic) of the studied nootropic agent were as follows : a=7.162 (6), b=8.852 (3), c=11.340 (8) Å ; Pbc21. The five-membered ring deviates from planarity, while the planes of the amide group and of the four atoms N (1)-C (1)-C (2)-C (4) are almost perpendicular in cis arrangement, with the 4-hydroxy group in the axial position. In the crystals, molecules are linked by two intermolecular hydrogen-bonds, namely O (3)…O (2) and N (2)…O (1), which are 2.77 and 2.92 Å long, respectively. Results of theoretical calculations indicate for the free molecule a twisted cis conformation, with the 4-hydroxy goup in the axial position, as the most preferred one. This appears to be determined by the intramolecular hydrogen-bond between the O (1) atom and amide group hydrogen atoms. The relative conformational energies indicate that several conformations about the minimum can be populated in the solution state. The geometry and conformational profile of the pharmacologically active investigated molecule were found to reproduce, with the exception of the puckered conformation of the fivemembered ring, those previously determined for the related analogous nootropic agent 2-oxo-1-pyrrolidineacetamide (piracetam), whose chemical structure differs only in the lack of the 4-hydroxy group in the β-position to the carbonyl group.View full abstractDownload PDF (642K) -
SHINSAKU MISHIO, TOHRU HIROSE, AKIRA MINAMIDA, JUNICHI MATSUMOTO, SHIN ...1985 Volume 33 Issue 10 Pages 4402-4408
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 7-substituted 1, 4-dihydro-4-oxo-1-vinyl-1, 8- and 1, 6-naphthyridine-3-carboxylic acids (5a-e and 13a-c) was prepared. During the preparation of 5a, unexpected compounds (4, 7 and 8) were also obtained. Structural elucidation of these compounds was achieved on the basis of chemical and spectral (ultraviolet, mass and proton nuclear magnetic resonance) data. The structure-antibacterial activity relationships are discussed.View full abstractDownload PDF (627K) -
MASAAKI MATSUO, KIYOSHI TANIGUCHI, YOUSUKE KATSURA, TOSHIHARU KAMITANI ...1985 Volume 33 Issue 10 Pages 4409-4421
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-(2-Phenoxyphenylimino) imidazolidine and related compounds (IV and XII) were synthesized and evaluated for hypotensive activity in rats. Most of the 2-aryliminoimidazolidines (IV) were synthesized via the aniline derivatives (VI) by two different methods. Some imidazolidines (IV) were found to be significantly active, with 2-(5-chloro-2-phenoxyphenylimino) imidazolidine (IV-19) being more active than prazosin, the reference compound. The mechanism of action of IV-9 may involve the blockade of peripheral α-adrenergic receptors. This paper describes the synthesis, pharmacology, and structure-activity relationships of the 2-(2-phenoxyphenylimino) imidazolidines.View full abstractDownload PDF (985K) -
GIICHI GOTO, KAYOKO OKAMOTO, TETSUYA OKUTANI, ISUKE IMADA1985 Volume 33 Issue 10 Pages 4422-4431
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-(ω-Hydroxyalkyl)-2, 3-dimethoxy-5-methyl-1, 4-benzoquinones (3) and 6-(ω-acetoxyalkyl)-2, 3-dimethoxy-5-methyl-1, 4-benzoquinones (26) having various carbon numbers (n) of the side chain were synthesized by the Friedel-Crafts coupling of 3, 4, 5-trimethoxytoluene (4) and ω-acetoxyalkanoyl chlorides (5) as a key step. The Fremy's salt oxidation or the salcomine-catalyzed oxidation of 6-(ω-hydroxyalkyl)-2, 3-dimethoxy-5-methylphenols (25) and their acetates (24), the key intermediates of the process, gave rise to 3 and 26, respectively, in good yields. The described method provides a good yield of the 1, 4-benzoquinones and is suitable for the synthesis of other quinonyl analogs. The effect on lipid peroxidation in canine brain homogenate of the 1, 4-benzoquinones (3) having various carbon numbers (n) of the side chain was studied. Among the compounds tested, 3 having a carbon number in the range of n=9-13 showed rather strong antioxidant activity.View full abstractDownload PDF (934K) -
KIYOSHI UKAWA, TOSHIHIRO ISHIGURO, HISASHI KURIKI, AKIRA NOHARA1985 Volume 33 Issue 10 Pages 4432-4437
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolites and degradation products of 2-amino-7-isopropyl-5-oxo-5H-[1] benzopyrano-[2, 3-b] pyridine-3-carboxylic acid (Amoxanox, AA-673, 1), a promising drug for the treatment of bronchial asthma, were synthesized to confirm the proposed structures and to determine their activity in the rat passive cutaneous anaphylaxis test.View full abstractDownload PDF (697K) -
NAOMICHI FUKUDA, MICHIKO YONEMITSU, TAKEATSU KIMURA, SHIZUKO HACHIYAMA ...1985 Volume 33 Issue 10 Pages 4438-4444
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new diterpene glucoside, borapetoside A (1), and its aglycone, borapetol A (2), were isolated from the stems of Tinospora tuberculata BEUMEE as the bitter principles, and their structures were elucidated.View full abstractDownload PDF (704K) -
TOSHIO MIYASE, MASANORI KUROYANAGI, TADATAKA NORO, AKIRA UENO, SEIGO F ...1985 Volume 33 Issue 10 Pages 4445-4450
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new guaiane-type sesquiterpene glycosides, macroclinisides F (II), G (III), H (IV) and I (V), and a new phenyl propanoid glycoside, 4-allyl-2, 6-dimethoxyphenol glucoside (VI), have been isolated from Macroclinidium trilobum MAKINO together with isolipidiol (I). The structures were determined on the basis of chemical and spectral data.View full abstractDownload PDF (697K) -
TOSHIO MIYASE, AKIRA UENO, TADATAKA NORO, MASANORI KUROYANAGI, SEIGO F ...1985 Volume 33 Issue 10 Pages 4451-4456
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNine new guainolide-type glycosides, crepisides A (II), B (III), C (IV), D (V), E (VI), F (VII), G (VIII), H (IX), and I (X), have been isolated from Crepis japonica BENTH., together with a known glycoside, glucozaluzanin C (I). The structures of II-X were established on the basis of chemical and spectral data.View full abstractDownload PDF (649K) -
TSUYOSHI TOMIMORI, YUKINORI MIYAICHI, YOSHITAKA IMOTO, HARUHISA KIZU, ...1985 Volume 33 Issue 10 Pages 4457-4463
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new flavanones (I-IV) and a new chalcone (V) were isolated from the root of Scutellaria discolor COLEBR., together with wogonin, norwogonin, 5, 7, 2'-trihydroxy-8-methoxyflavone, 5, 7-dihydroxy-8, 2'-dimethoxyflavone and wogonin 7-O-glucuronide. The structures of I-V were shown to be 2 (S)-5, 7-dihydroxy-8, 2'-dimethoxyflavanone, 2 (S)-7-hydroxy-5, 8, 2'-trimethoxyflavanone, (±)-5, 2'-dihydroxy-7, 8, 6'-trimethoxyflavanone, (±)-5, 2'-dihydroxy-6, 7, 6'-trimethoxyflavanone and 2', 4'-dihydroxy-2, 3', 6'-trimethoxychalcone, respectively, based on spectral data and simple chemical modifications.View full abstractDownload PDF (879K) -
JUNYA OKADA, SADAO KONDO1985 Volume 33 Issue 10 Pages 4464-4470
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA double-antibody solid-phase enzyme immunoassay for determining des-Gly10-NH2-LH-RH-ethylamide (fertirelin) in bovine plasma was developed. Antiserum was raised against fertirelin-BSA conjugate, and enzyme-labeled antigens were prepared by coupling fertirelin analogues bearing an N-terminal amino group with β-D-galactosidase using N-(m-maleimidobenzoyloxy)-succinimide (MBS). The antiserum cross-reacted hardly at all with LH-RH and only slightly with peptides bearing a different C-terminal alkyl substituent, but it was less specific for the N-terminus. Plasma specimens were extracted with antibody-immobilized cellulose in order to minimize substances interfering with the assay. This assay system could detect as little as 0.2 ng/ml of fertirelin in the absence of plasma extract and 1.0 ng/ml in the presence of the extract. The mean recovery of fertirelin added to plasma was 80.9% and the coefficients of variation were 14.4% (within assay) and 17.5% (between assay).View full abstractDownload PDF (741K) -
HIROTERU SAYO, MIKIO HOSOKAWA1985 Volume 33 Issue 10 Pages 4471-4477
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stoichiometry and kinetic mechanism of the cumene hydroperoxide (CHP)-supported N-demethylation of N, N-dimethylaniline (DMA) catalyzed by catalase were studied. The formations of formaldehyde, 2-phenyl-2-propanol and N-methylamiline, and the consumption of DMA exhibited a 1 : 1 : 1 : 1 stoichiometry up to 5 min after initiation of the reaction. Plots of reciprocal initial velocity versus the reciprocal concentration of either substrate at several different fixed concentrations of the other substrate resulted in a family of straight lines which converged to a common intersection point on the left side of the ordinate and above the abscissa, suggesting a sequential mechanism involving the formation of a ternary complex of catalase, DMA and CHP followed by one or more reactions and the subsequent release of the products. N, N, N', N'-Tetramethylbenzidine radical cation was detected by electron spin resonance spectroscopy during the CHP-supported oxidation of DMA, whereas the corresponding amine radical cations were detected during the oxidations of N, N-dimethyl-p-toluidine and N, N-dimethyl-p-anisidine. These results suggest that the mechanism of the CHP-supported oxidation of DMA catalyzed by catalase is the same as that of aminopyrine.View full abstractDownload PDF (726K) -
YOSHIHIKO INAMORI, MAYURI KUBO, MASAFUMI OGAWA, MASAMITSU MORIWAKI, HI ...1985 Volume 33 Issue 10 Pages 4478-4483
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDiethylstilbestol (I), a nonsteroidal estrogen, showed strong coronary vasodilator action on isolated guinea-pig heart, as well as ichthyotoxicity and antimicrobial activity. First, the coronary vasodilator action of I (ED50 : 0.26μg/heart) on isolated guinea-pig heart was much stronger than that of papaverine (ED50 : 7.0μg/heart) used as a standard. On the other hand, the activities of derivatives of I, i. e., I-diphosphate (II), I-dimethyl ether (III), I-diacetate (IV), I-dipropionate (V) and hexestrol (VI) were weaker than that of I. Second, I showed strong ichthyotoxicity (median tolerance limit at 48h : 3.30 ppm in Oryzias latipes and 4.50 ppm in Carassius auratus). On the other hand, the ichthyotoxic activities of II-V were weaker than that of I. However, VI showed the same toxicity as I on both fishes. Third, the antimicrobial activities of II-V were weaker than that of I, whereas that of VI was stronger. In particular, I and VI showed strong antifungal activity against Trichophyton spp. It was concluded that both the hydroxyl groups attached to the benzene rings and the transolefin structure are necessary for coronary vasodilator action, while only the hydroxyl groups attached to the benzene ring are necessary for the ichthyotoxic and antimicrobial activities.View full abstractDownload PDF (672K) -
Isolation of Serine, Glutamic Acid, and Glycine-Rich Nonhistone Proteins from Bovine Cerebral CortexTOSHIKO SHIBAYAMA, KAZUYASU NAKAYA, YASUHARU NAKAMURA1985 Volume 33 Issue 10 Pages 4484-4488
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo nonhistone proteins with molecular weights of 63000, and 53000 were isolated from bovine cerebral cortex by polyacrylamide gel electrophoresis with a urea-acetic acid system, followed by extraction from the gel. These proteins have a particularly large proportions of Ser, Gly and Glu, which represent 40% of total amino acids. Such amino acid compositions are unusual among nonhistone proteins. These proteins also contained 1.00 and 0.27% (w/w) phosphate/mg protein.View full abstractDownload PDF (565K) -
MASAYOSHI YAMAGUCHI, HIROYUKI YOSHIDA1985 Volume 33 Issue 10 Pages 4489-4493
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe role of a calcium-binding protein (CaBP) isolated from rat liver cytosol was investigated in relation to the activation of hepatic fructose 1, 6-diphosphatase by Ca2+-calmodulin. Fructose 1, 6-diphosphatase activity in rat liver cytosol was markedly increased by addition of Ca2+ (1.0-5.0 μM) to the incubation mixture. This increase was completely inhibited in the presence of N-(6-aminohexyl)-5-chloro-1-napthalenesulfonamide (W-7 15 μM), an inhibitor of calmodulin. Added Ca2+ (5.0 μM)-increased cytosolic fructose 1, 6-diphosphatase activity was markedly enhanced by the coexistence of calmodulin (2.5 μg/ml). Further, fructose 1, 6-diphosphatase isolated from rabbit liver cytosol was activated by Ca2+-calmodulin. This activation was completely inhibited by CaBP (20 μg/ml) isolated from rat liver cytosol, though CaBP in the absence of calmodulin had no effect on liver fructose 1, 6-diphosphatase activity. The present data suggest that CaBP can modify the action of Ca2+-calmodulin in liver cells. It is proposed that CaBP, which may regulate Ca2+ effects on liver function, should be named calregulin.View full abstractDownload PDF (609K) -
TETSURO NAGASAWA, HIKOKICHI OURA, GENICHIRO NONAKA, ITSUO NISHIOKA1985 Volume 33 Issue 10 Pages 4494-4499
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism by which rhatannin (condensed tannin purified from Rhei Rhizoma) produces a prolonged decrease in plasma amino acids in the postabsorptive state was investigated in vivo by measuring the incorporation of [14C] phenylalanine (Phe) into proteins in serum, liver, kidney and muscle. Enhanced incorporation into serum proteins was observed 4 to 8 h after the intraperitoneal administration (12.5 mg/kg body weight), and the maximal enhancement was observed 6 h after the treatment. Incorporations into other proteins did not change. Further, a fluorogram of the polyacrylamide gel electrophoretic pattern of serum obtained from rats after rhatannin treatment revealed incorporation of the labeled amino acid into protein (s) which corresponded to albumin in terms of electrophoretic mobility. Incorporation of [3H] phenylalanine after a 20 min in vivo labeling 6 h after rhatannin treatment was enhanced in hepatic microsomal and mitochondrial fractions. In addition, stimulated incorporation of [3H] orotic acid into rat hepatic nuclear and cytoplasmic ribonucleic acids (RNA) was observed after rhatannin treatment and the maximal enhancements were achieved at 6 h. Thus, the decrease of plasma amino acid level 4 to 8 h after rhatannin treatment may be due in part to the increased removal of amino acids by the liver, although the underlying mechanisms of enhancement of the syntheses of hepatic protein and RNA in rhatannintreated rats remain obscure.View full abstractDownload PDF (808K) -
HIDEAKI WATANABE, SAKAE SUGIYAMA, YOSHIMI NAKAMOTO, KYOKO MATSUNO, KAZ ...1985 Volume 33 Issue 10 Pages 4500-4507
Published: October 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe role of tyrosyl residues in the enzymatic activity and the state of tyrosyl residues of guanine preferential ribonuclease (RNase Ms) from Aspergillus saitoi were studied. 1) The solvent perturbation difference spectra of RNase Ms measured with ethylene glycol and polyethylene glycol as perturbants indicated that ca. 5 tyrosyl residues and one tryptophan residue were exposed to solvents. 2) The spectrophotometric titration of RNase Ms indicated that ca. 5 tyrosyl residues were titrated first, giving an apparent pKa value of 10.5, and the rest of the tyrosine residues gave higher pKa values. 3) About 8 tyrosine residues in RNase Ms were acetylated by excess N-acetylimidazole and about 6 of them were reactive towards a relatively low concentration of the reagent. Extrapolation of the curve showing the relation between the tyrosyl residues modified and the remaining activity indicated that the enzyme was inactivated when 4-5 tyrosyl residues were modified. 4) The chemical modification of RNase Ms with diazonium 1 (H)-tetrazole was also studied. The plot of the relationship between the residual activity and the tyrosyl residues modified showed that 1-1.5 tyrosyl residue (s) was responsible for the loss in enzymatic activity. 5) The enzymatic activities of RNase Ms modified by the two kinds of tyrosine-modifying reagents were measured with ribonucleic acid (RNA) and guanyl (3'→5') cytidine (GpC) as substrates at pH 5.0. The loss in enzymatic activity was more marked when RNA was used as a substrate than with GpC as a substrate. 6) Based on the reported (Heinemann and Saenger, Nature, 299, 27 (1982)) three-dimensional structure of RNase T1, which is about 60% sequence-homologous with RNase Ms, the possible site of the diazotization is discussed.View full abstractDownload PDF (826K)