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Mahendra SAHAI, Sanjewon SINGH, Manorama SINGH, Yogesh Kumar GUPTA, Sa ...
1994 Volume 42 Issue 6 Pages
1163-1174
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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The petroleum ether extract of the seeds of Annona squamosa L. yielded thirteen adjacent and four non-adjacent bis-tetrahydrofuranic acetogenins, in addition to squamocin (1) and squamostatin-A. The structures of the thirteen acetogenins, named as squamocins-B (2), -C (3), -D (4), -E (5), -F (6), -G (7), -H (8), -I (9), -J (10), -K (11), -L(12), -M (13) and -N (14), have been established on the basis of spectral evidence. Squamocins-B, -D, -E, -F, -I, -K and -N are new acetogenins. The structures of these acetogenins vary in hte carbon number (C
37 or C
35), the number and position of hydroxyl groups (substituted at C-4, C-12, C-28 or C-29) and the stereochemistry at the bis-tetrahydrofuran moiety. Squamocin-N (14) has an unprecedented threo-cis-threo-cis-threo stereochemistry in its bis-tetrahydrofuran portion. Co-occurrence on a diastereoisomeric pair, 9 and 10, is noteworthy.
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Yoshinori FUJIMOTO, Chikako MURASAKI, Hiroyasu SHIMADA, Seiichi NISHIO ...
1994 Volume 42 Issue 6 Pages
1175-1184
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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Four non-adjacent bis-tetrahydrofuranic acetogenins, named squamostatins-B (2), -C (3), -D (4) and -E (5), have been isolated from the petroleum ether extract of Annona squamosa seeds. The structures of these acetogenins have been established on the basis of spectral evidence. C-15/C-16-threo, C-19/C-20-threo, C-23/C-24-erythro stereochemistry was assigned for squamostatins-B and -D, whereas C-15/C-16-threo, C-19/C-20-threo, C-23/C-24-threo stereochemistry was assigened for squamostatins-C and -E. All of these acetogenins, including squamostatin-A, have been established to have C-12/C-15-trans, C-20/C-23-trans stereochemistry by
13C-NMR comparison with synthetic model mono-tetrahydrofuranic compounds. An improved <13>C-NMR assignment of squamostatin-A is presented.
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Shunsaku OHTA, Yasunari HINATA, Masayuki YAMASHITA, Ikuo KAWASAKI, Tak ...
1994 Volume 42 Issue 6 Pages
1185-1190
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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Synthesis of 3-alkylamino-1, 4-naphthoquinone-2-carboxylic acid (2) was attempted. Although 3-(1-piperidinyl)-1, 4-naphthoquinone-2-carboxylic acid (2a) was not obtained, probably because of its instability, the esters (18a, b)of 2a could be prepared. 2-Alkylamino-3-hydroxymethyl-1, 4-naphthoquinones (9a-g) were photochemically cyclized to the 1, 4, 5, 10-tetrahydro-5, 10-2H-naphth[2, 3-d][1, 3]oxazines (19a-g), containing a novel heterocyclic ring system in moderate yields. Anti-bacterial activity of the prepared compounds was weak or insignificant.
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Takashi MATSUMOTO, Yoshio TAKEDA, Eiko IWATA, Mitsuo SAKAMOTO, Takashi ...
1994 Volume 42 Issue 6 Pages
1191-1197
Published: June 15, 1994
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Racemic 1-acetoxy-2-phenylpropane (12) and 1-acetoxy-2-(2-naphthyl)propane (33) were hydrolyzed with lipse at 35-36°C for 2 and 24 h to give predominantly (S)-2-phenyl-1-propanol (11) and (S)-2-(2-naphthyl)-1-propanol(32), respectively. However, racemic 1-acetoxy-2-(1-naphthyl)propane (25) was recovered intact even when the reaction was carried out for 240 h. On the other hand, the enantioselectivities towards racemic 2-phenyl (16), 2-(p-tolyl)(20), 2-(1-naphthyl)(28), and 2-(2-naphthyl)(36) derivatives of 1-acetoxy-2-propanol were very low.
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Yuichi ENDO, Hiroko HAYASHI, Toshitsugu SATO, Masao MARUNO(M. Chin), T ...
1994 Volume 42 Issue 6 Pages
1198-1201
Published: June 15, 1994
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Monoamine oxidase B (MAO-B) inhibitors were isolated from the bark of a Brazilian plant, Himatanthus sucuuba (SPR.). Assignments of the
1H-and
13C-NMR data using two dimensional (2D)-NMR techniques showed the active components to be known lichen depsides, confluentic acid (1) and 2'-O-methylperlatolic acid (2). The depside (1) showed selective inhibition of MAO-B with IC
50 value of 0.22μM.
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Henry HEYMANN, Yasuhiro TEZUKA, Tohru KIKUCHI, Sutardjo SUPRIYATNA
1994 Volume 42 Issue 6 Pages
1202-1207
Published: June 15, 1994
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Seven new trans-clerodane-type diterpenoids and three known ones have been identified from the chloroform-soluble fraction of the methanolic extract of Sindora sumatrana MIQ. The new compounds, each of which has a β-acetoxy group at the C-7 position, comprise three acid diterpenoids (3, 5, 6) and three neutral ones(8, 9, 10). The remaining one (7) is a dimethyl ester, which was obtained from an acid fraction after methylation with diazomethane. The structures of the isolated compounds were detemined by means of spectroscopic methods, mainly two-dimensional NMR techniques, and their relative stereochemistries were determined with the aid of difference nuclear Ovverhauser effect experiments.
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Hiroyuki AKITA, Masako NOZAWA, Shinji NAGUMO
1994 Volume 42 Issue 6 Pages
1208-1212
Published: June 15, 1994
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By applying the Hantzsch thiazole procedure, the synthesis of bithiazole derivatives (2 and (±)-3) corresponding to degradation products of myxothiazol was achieved. Optically active (S)-3 (87-88% ee) and its analog (S)-16(91% ee) were obtained through enantioselective hydrolysis of the corresponding acetates ((±)-18, (±)-20 and (±)-21) using lipase in water-saturated organic solvent.
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Yuko TAKEMURA, Toshimi NAKATA, Motoharu JU-ICHI, Masayoshi OKANO, Nari ...
1994 Volume 42 Issue 6 Pages
1213-1215
Published: June 15, 1994
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Three new bicoumarins named bisnorponcitrin (1), khelmarin-C (2), and bishassanidin (3) were isolated from the root of Citrus hassaku HORT. ex TANAKA (Rutaceae) and their structures were elucidated on the basis of spectroscopic analyses.
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Takakuni MATSUDA, Masanori KUROYANAGI, Satoko SUGIYAMA, Kaoru UMEHARA, ...
1994 Volume 42 Issue 6 Pages
1216-1225
Published: June 15, 1994
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The methanol extract of the aerial part of Andrographis paniculata NEES showed potent cell differentiation-inducing activity on mouse myeloid leukemia (M1) cells. From the ethyl acetate-soluble fraction of the methanol extract, six new diterpenoids of ent-labdane type, 14-epi-andrographolide (3), isoandrographolide (4), 14-deoxy-12-methoxyandrographolide (7), 12-epi-14-deoxy-12-methoxyandrographolide (8), 14-deoxy-12-hydroxyandrographolide (9) and 14-deoxy-11-hydroxyandrographolide (10) as well as two new diterpene glucosides, 14-deoxy-11, 12-didehydroandrographi-side (12) and 6'-acetylneoandrographolide (14), and four new diterpene dimers, bis-andrograpolides A (15), B (16), C (17) and D (18), were isolated along with six known compounds. The structures of the diterpenoids were determined by means of spectral methods. Some of these compounds showed potent cell differentiation-inducing activity towards M1 cells.
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Masayuki YOSHIKAWA, Shoko YAMAGUCHI, Kumiko KUNIMI, Hisashi MATSUDA, Y ...
1994 Volume 42 Issue 6 Pages
1226-1230
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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An anti-ulcer constituent, 6-gingesulfonic acid, and three monoacyldigalactosylglycerols, gingerglycolipids A, B, and C, were isolated from Zingiberis Rhizoma, the dried rhizome of Zingiber officinale ROSCOE which was cultivated in Taiwan, together with (+)-angelicoidenol-2-O-β-D-glucopyranoside. Based on chemical reactions and physicochemical evidence, the structures of 6-gingesulfonic acid, gingerglycolipids A, B, and C have been determined.In addition, the absolute stereostructure of (+)-angelicoidenol-2-O-β-D-glucopyranoside was clarified on the basis of its synthesis from d-borneol. 6-Gingesulfonic acid showed weaker pungency and more potent anti-ulcer activity than 6-gingerol and 6-shogaol.
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Tozo FUJII, Tohru SAITO, Tetsunori FUJISAWA
1994 Volume 42 Issue 6 Pages
1231-1237
Published: June 15, 1994
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Three variants of a syntheric route to the antitumor antibiotic azepinomycin (3) from 1-substituted N'-alkoxy-5-formamidoimidazole-4-carboxamidine (type 10) are described. The synthesis started with the monocycles 10a-c and proceeded through the intermediates 11a-c, 12a-c, 13a-c, 14a-c, and 4a, b and 3-β-D-ribofuranosylazepinomycin (4c). The benzyl version (series a), including the permutation 14a→15→3, was found to produce the antibiotic (3) most efficiently. The starting materials 10a-c were readily prepared from the 9-substituted adenines 7a-c via the N-oxides 8a-c and the 1-alkoxy derivatives 9a-c. The 8-imino analogues (17 and 18) of 3 and 4c were also synthesized from 12a and 12c, respectively.
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Yoshihiro KAWASAKI, Hiroaki KONISHI, Minoru MORITA, Masami KAWANARI, S ...
1994 Volume 42 Issue 6 Pages
1238-1242
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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Hydrogen storage alloys are capable of charging and discharging hydrogen in temperature-dependent manner, and are employed as catalysts for hydrogenation and dehydration. In water, CaNi
5 removed protecting groups such as benzyloxycarbonyl, benzyl ester, benzyl ether and nitro groups without any side reactions, and the reaction time was highly dependent on the hydrogen pressure of the reaction system In organic solvents such as dioxane and EtOAc the deprotection reaction did not proceed. Methanol (MeOH) was applicable, but the reaction in MeOH required a longer reaction time than in water. A mixture of water and MeOH accelerated the reaction depending on the water content. Although the mechanism of the catalytic hydrogenation with CaNi
5 in water and/or MeOH is uncertain, the reaction between Ca and water or MeOH seems to be of critical importance.
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Tetsuaki TANAKA, Yousuke FUNAKOSHI, Kenji UENAKA, Kimiya MAEDA, Hideno ...
1994 Volume 42 Issue 6 Pages
1243-1246
Published: June 15, 1994
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The reactivity of the tricyclic enone, (+)-(1S, 2R, 4R, 7R)-3, 3, 7-trimethyltricyclo[6.3.0.0
2, 4]undec-8-en-10-one(1), obtained previously as the key intermediate for the synthesis of compounds bearing the aromadendrane uncleus was investigated, and a natural aromadendrane-type sesquiterpene, (+)-1, 2-didehydroaromadendrane (2), was synthesized via regio- and stereo-specific introduction of a methyl group at the C-11 position of 1 followed by reductive deoxygenation.
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Naoki NODA, Ryuichiro TANAKA, Kazumoto MIYAHARA
1994 Volume 42 Issue 6 Pages
1247-1250
Published: June 15, 1994
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Eight glycosphingolipids have been isolated in the pure state from the crude drug "Jiryu" (the dried body wall of the earthworm, Pheretima asiatica). Their structures have been determined on the basis of chemical and spectroscopic evidence. All the compounds carry a phosphocholine group attached to the sugar moiety, and seven of them consist of ceramide units with branched-chain bases (C
18 : 1, C
19 : 1 iso type).
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Nobuya KATAGIRI, Hironori NOCHI, Ayumu KURIMOTO, Hiroshi SATO, Chikara ...
1994 Volume 42 Issue 6 Pages
1251-1257
Published: June 15, 1994
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Synthesis of 5-isonitroso-1, 3-dioxane-4, 6-dione (2 : isonitroso Meldrum's acid) and related compounds and their reactions were described. Compound (2) reacted with various alcohols to give hydroxyiminoacetic acid esters in moderate yields. Compound 2 was acetylated in the usual manner to give 5-acetoxyimino-1, 3-dioxane-4, 6-dione (9)as a stable crystalline substance, which acted not as a heterodiene but as a heterodienophile and underwent hetero Diels-Alder reaction with various dienes to form [4+2] adducts.
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Yasuo NAGAOKA, Akira IIDA, Teturo FUJITA
1994 Volume 42 Issue 6 Pages
1258-1263
Published: June 15, 1994
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A membrane-modifying peptide antibiotic, trichosporin B-VIa, having catecholamine secretion-inducing activity on bovine adrenal chromaffin cells has been synthesized. Aib
14-Trichosporin B-VIa, in which Pro
14 was replaced by Aib, has also been synthesized to modify the secondary structure of trichosporin B-VIa. Sequience-specific
1H-NMR assignments of both peptides in methanol were achieved by using two-dimensional NMR techniques.
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Tomoji AOTSUKA, Hiroshi HOSONO, Toshio KURIHARA, Yoshiyuki NAKAMURA, T ...
1994 Volume 42 Issue 6 Pages
1264-1271
Published: June 15, 1994
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A number of 1, 4-benzothiazine-2-acetic acid derivatives (1, 2 and 3) and their bioisosteres (15b, 16, 18 and 20b) were synthesized and evaluated in vitro for the ability to inhibit aldose reductase (AR) in porcine lens. The compounds which exhibited potent activity in vitro were also assayed in vivo for inhibitory activity against sorbitol accumulation in the erythrocytes, sciatic nerve and lens of streptozotocin-diabetic rats. The 4-(substituted benzothiazol-2-ylmethyl)-1, 4-benzothiazine-2-acetic acid derivatives (2 and 3) showed more potent AR inhibitory activity than did the 4-(4-bromo-2-fluorobenzol)-1, 4-benzothiazine-2-acetic acid derivatives (1). 4-(4, 5, 7-Trifluorobenzothiazol-2-ylmethyl)-3, 4-dihydro-3-oxo-2H-1, 4-benzothiazine-2-acetic acid (2q, SPR-210) showed not only a potent AR-inhibitory activity in vitro (IC
50 9.5×10
-9 M) but also a significant reduction in sorbitol accumulation in rat sciatic nerve (ID
50 0.1 mg/kg) and lens (ID
50 9.8 mg/kg). Optical resolution of the racemic SPR-210 was achieved by means of a diastereomer salt method using (-)-brucine. The biological activities of both enantiomers, (+)- and (-)-SPR-210, were comparable to that of the racemate.
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Hirokazu HASHIZUME, Hajime ITO, Naoaki KANAYA, Hajime NAGASHIMA, Hiroy ...
1994 Volume 42 Issue 6 Pages
1272-1278
Published: June 15, 1994
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Isosteric side chain analogs of 3a were synthesized and tested for inhibitory activivies towards 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase and upon cholesterol production in Hep G2 cells and in mouse liver. It became clear that the lipophilic substituent on the aromatic ring and the terminal hydrophilic group in the side chain were important in the enhancement of activity. 4-[2-(3-n-Hexyloxyphanyl)ethyl]-3-hydroxymethyl-2-oxetanone (5a) showed equivalent inhibitory activity in vivo to that of 1233A.
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Mitsuru OHKUBO, Atsushi KUNO, Hiroyoshi SAKAI, Yoshie SUGIYAMA, Hisash ...
1994 Volume 42 Issue 6 Pages
1279-1285
Published: June 15, 1994
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Novel pyrimidine derivatives, possessing linkages between the aryl group and the pyrimidine nucleus at the C-4 position, were prepared and tested for anti-anoxic (AA) activity in mice. Among them, 5-(4-methylpiperazin-1-ylcarbonyl)-4-(4-nitrobenzoyl)-2-phenylpyrimidine (2f, FR76659) possessed significant AA activity (10-100 mg/kg, i.p.) with low acute toxicity (LD
50>1000 mg/kg, i.p.). Structure-activity relationships in regard to AA activity of this series of compounds were examined.
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Mario GIANNELLA, Alessandro PIERGENTILI, Maria PIGINI, Wilma QUAGLIA, ...
1994 Volume 42 Issue 6 Pages
1286-1290
Published: June 15, 1994
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To acquire more information about the so-called "muscarinic subsite", compound 4 was synthesized and tested.The results show that in comparison with deoxamuscarine (23) the muscarinic potency of 4 on M
2 and M
3 subtypes is not significantly altered by the presence of an epoxidic function, which confirms the donor-acceptor hydrogen bonding charactor of this receptive site. Conversely, there is a negative influence on the transduction prosesses. In addition, a second hydroxylic function bound on the carbon carrying the terminal methyl of the fourth substituent on the nitrogen dramatically affects the muscarinic behavior; the resulting compounds (11-1) lack any agonist or antagonist activity.
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Ryouko YAMAMOTO, Toshio MIYASE, Akira UENO
1994 Volume 42 Issue 6 Pages
1291-1296
Published: June 15, 1994
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Water extracts from the whole plant of Stachys riederi gave eight new bisdesmosides of echinocystic acid. The stuctures of these compounds were elucidated by chemical and spectroscopic evidence.
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Yoshie MAITANI, Miho KUGO, Tsuneji NAGAI
1994 Volume 42 Issue 6 Pages
1297-1301
Published: June 15, 1994
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To understand the mechanism of percutaneous absorption of ionizable drugs, diclofenac salts (DM : M=Li, Na, K, NH
4, N(Me)
4) as hydrophilic drugs were compared to free diclofenac acid (DH), a hydrophobic drug. DNa showed the highest permeability coefficient among DMs. The experimental diffusion coefficient through the silicone membrane (Dm) was compared with the calculated diffusion coefficient for an ion pair molecule (Dm
pair) of DM.This may suggest that the existence of the lipid pathway of the DMs is the same as the DH.
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Satoru WATANO, Toru FUKUSHIMA, Kei MIYANAMI, Takayuki MURAKAMI, Toshih ...
1994 Volume 42 Issue 6 Pages
1302-1307
Published: June 15, 1994
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The automated manufacturing process of cold remedy granules using a tumbling fluidized bed will be described.Powdered materials, containing salicylamide and acetaminophen as the main components and having been used for the extrusion process previously, were granulated by a tumbling fluidized bed. Effects of the operational variables on the properties of granules were investigated, which led to the conclusion that the exact control of bed height and moisture content was indispensable for continuously producing desired granules. The fuzzy control method based on a linguistic algorithm of if-then rules was applied to the bed height control, and programmed control of the moisture content was used for the continuous operation from mixing, granulation to drying. By means of the system developed, a series of operations could be conducted automatically. Properties of the granules thus obtained were evaluated, and a comparison of the granules by this process to those by the extrusion process used previously was conducted.It was concluded that by means of the control system developed, desired granules which had sharp particle size distribution, high yield, i.e., almost 100% of granules, large apparent density and remarkably good flowability were easily produced.
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Hideki ICHIKAWA, Hiroyuki TOKUMITSU, Kaori JONO, Tomoaki HUKUDA, Yoshi ...
1994 Volume 42 Issue 6 Pages
1308-1314
Published: June 15, 1994
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An aqueous acrylic latex which could exhibit a low degree of agglomeration, low membrane permeation and high coating efficiency was developed using copoly(ethyl acrylate (EA)-methyl methacrylate (MMA)-2-hydroxyethyl methacrylate (HEMA)) whose molar ratio was 6 : 12 : 8 or 12 : 6 : 4. Blend latices composed of the hydrophilic 6 : 12 : 8 latex and the hydrophobic 12 : 6 : 4 latex exhibited a very low degree of agglomeration. However, the coating operation had problems with particle adhesion and cohesion due to the low softening temperature (26°C) of the 12 : 6 : 4 copolymer. In addition, the release of lactose from the microcapsules coated with the substances, even if cured by heating, could not be sufficiently suppressed, with a fraction of fast releasing microcapsules remaining due to a variation of the membrane structure formed by the random packing of latex particles. Hence, composite latices composed of the low permeable 12 : 6 : 4 copolymer core and the nonadhesive 6 : 12 : 8 polymer shell were synthesized.A 6 : 4 (core : shell) composite latex formed a low permeable membrane by curing, so that the microcapsules of 53-63μm lactose 40% coated with it released only 10% of its lactose at 3h without an initial burst. Moreover, composite latices exhibited a very low degree of aglomeration, with the polymer yield remaining very high, and they did not induce any adhesive behavior. These properties were still effective even in the coating of corn starch as fine as 12μm. At a 50% level of coating, the mass median diameter of the product was 16μm and it contained only 3% agglomerates. These results showed that by using the composite latex the particles of the order of 10 μm could be discretely coated as single-core microcapsules in the Wurster process, a kind of spouted bed process assisted with a draft tube.
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Takatoshi KAWAI, Nobuo TOMIOKA, Tazuko ICHINOSE, Mayuko TAKEDA, Akiko ...
1994 Volume 42 Issue 6 Pages
1315-1321
Published: June 15, 1994
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The dynamic behaviors of the cyclohexane molecule have been simulated by normal- and high-temperature molecular dynamics calculation. At 1000 K, all of the well-known conversion processes and equilibria between conformers (chair form inversion, boat-chair conversion and pseudorotation) were fully reproduced in the trajectories within a practical simulation time, 50 ps, whereas at normal temperature (300 K), these conversions scarcely occurred even during an extraodinarily long simulation time, 100 ns. The calculated structures and relative stabilities of conformers agreed well with the experimental data. These satisfactory results with this well-studied molecule imply applicability of unrealistically high-temperature simulation to the prediction of dynamic behaviors of other molecules.
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Hidetoshi FUJIWARA, Ichizo OKABAYASHI
1994 Volume 42 Issue 6 Pages
1322-1324
Published: June 15, 1994
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The Skraup reaction of amino-9H-thioxanthen-9-ones was conducted in the presence of glycerol, fuming sulfuric acid, nitrobenzone, iron(II) sulfate and boric acid. 1-Amino-9H-thioxanthen-9-one (1) gave 12H-[1]benzothiopyrano[2, 3-h]quinolin-12-one (5). 2-Amino-(2) and 3-amino-9H-thioxanthen-9-ones (3) gave angular-type products, 12H-[1]benzothiopyrano[3, 2-f]quinolin-12-one (6) and 7H-[1]benzothiopyrano[2, 3-f]quinolin-7-one (8), but did not give linear-type products. 4-Amino-9H-thioxanthen-9-one (4) gave 7H-[1]benzothiopyrano[3, 2-h]quinolin-7-one(10).
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Keizo MATSUO, Shigetoshi ISHIDA
1994 Volume 42 Issue 6 Pages
1325-1327
Published: June 15, 1994
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Murrayaquinone-A, one of the carbazolequinone alkaloids isolated from Murraya euchrestifolia HAYATA(Rutaceae), was prepared starting from 1, 2, 3, 4-tetrahydrocarbazol-4(9H)-one in good overall yield.
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Hideaki KURODA, Masaaki MIYASHITA, Hiroshi IRIE, Tamio UENO
1994 Volume 42 Issue 6 Pages
1328-1330
Published: June 15, 1994
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Methyl (4S, 5R)-4-(N-acetylphenylalanyl)oxy-5, 6-epoxy-5-methylhex-2(E)-enoate, the enantiomeric analogue of AK-toxin, the host-specific toxin, and its stereoisomers have been synthesized and tested for host-specific toxin activity.
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Shiyomi KOYAMA, Naohiro SHIRAI, Yoshiro SATO
1994 Volume 42 Issue 6 Pages
1331-1333
Published: June 15, 1994
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N, N-Dimethyl-(1- or 2-naphthylmethyl)ammonium N-methylide (2a, b) produced from N, N-dimethyl-N-[(trimethylsilyl)methyl](1- or 2-nephthylmethyl)ammonium iodide (1a, b) with CsF in N, N-dimethylformamide, was rearranged to 2[(dimethylamino)methyl]-1, 2-dihydro-1-naphtholidene (3a) or 1-[(dimethylamin)methyl]-1, 2-dihydro-2-naphtholidene (3b), respectively, in high yield. Aromatization of 3a, b to the Sommelet-Hauser products(4a, b) occurred with the aid of KOH or heating.
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Yoshinori FUJIMOTO, Chikako MURASAKI, Tadashi EGUCHI, Katsumi KAKINUMA ...
1994 Volume 42 Issue 6 Pages
1334-1335
Published: June 15, 1994
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Treatment of fern-9(11)-en-25-ol mesylate (2) with LiAlH
4 in refluxing tetrahydrofuran afforded 9, 25-cyclofernane(4), a new cyclopropane ring-containing triterpene, in a moderate yield.
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Shoji YAHARA, Ning DING, Toshihiro NOHARA
1994 Volume 42 Issue 6 Pages
1336-1338
Published: June 15, 1994
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From the whole parts of Eclipta alba HASSK., six new oleanane triterpene glycosides, named eclalbasaponins I-VI (1-6), were isolated. The structures of 1-6 were characterized as echinocystic acid glycosides, and of those, 5 and 6 were revealed to be sulfated saponins on the basis of chemical and spectral data.
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Junei KINJO, Hadzuki UEMURA, Motoyuki NAKAMURA, Toshihiro NOHARA
1994 Volume 42 Issue 6 Pages
1339-1341
Published: June 15, 1994
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Two new triterpenoid glycosides called medicago-saponins P
1 (1) and P
2 (2) were isolated together with five known glycosides from the aerial parts of Medicago polymorpha L. (Leguminosae). The structures of 1 and 2 were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl caulophyllogenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside and the desglucoside of 1.
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Eihei FUKUOKA, Midori MAKITA, Shigeo YAMAMURA, Yasuo YOSHIHASHI
1994 Volume 42 Issue 6 Pages
1342-1344
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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Sulfacetamide reacted with phthalic anhydride in the solid state and was gradually converted into phthalylsulfacetamide with mechanical grinding. Formation of phthalylsulfacetamide was confirmed by high pressure liquid chromatography and Fourier transform infrated spectroscopy. The X-ray diffraction pattern of ground powder of sulfacetamide and phthalic anhydride mixture (1 : 1 by molar ratio) gradually became a halo with the formation of phthalylsulfacetamide, indicating that amorphous phthalylsulfacetamide was obtained by the solid-state reaction with mechanical grinding. The solid-state reaction between sulfacetamide and phthalic anhydride also occurred when a mixture of the two was heated. Crystalline phthalylsulfacetamide was formed by the solid-state reaction with heating.
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Koichiro MIYAJIMA, Seiichi TANIKAWA, Mina ASANO, Katsumi MATSUZAKI
1994 Volume 42 Issue 6 Pages
1345-1347
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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We have developed a model membrane system for estimating drug permeability of skin by fixing liposomes composed of stratum corneum (SC) lipids (ceramides, palmitic acid, cholesterol, and cholesterol-3-sulfate) onto a supporting filer, Biodyne B (Chem. Pharm. Bull., 41, 575 (1993)). In both the model membrane and guinea pig skin experiments, the addition of absorption enhancers (Azone, decylmethylsulfoxide, oleic acid, and capric acid)caused an increase in cyclobarbital (a relatively hydrophilic drug) permeation, but had littel effect on ibuprofen (a hydrophobic drug) permeation. Thus, the model membrane and guinea pig skin behave similarly in terms of permeability, suggesting that the main target of the enhancers is the SC intercellular lipid lamellae. The influence of SC lipid composition on permeability was also investigated. A lipid composition similar to that of skin SC showed the lowest permeability for the hydrophilic drug. Our model membrane system was found to be widely applicable for drug permeation studies.
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Yoshihiro SAITO, Yukisige KONDO, Masahiko ABE, Takatoshi SATO
1994 Volume 42 Issue 6 Pages
1348-1350
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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The solubilization of estriol was studied in an aqueous solution of a poly(ethylene oxide)/poly(proplylene oxide)/poly(ethylene oxide) triblock copolymer (pluronic L-64).The solubility of estriol increased with increasing pluronicL-64 concentrations and temperatures. Two clear transition points were found on the solubility curves at 30 and 40°C. These two transition points were in good agreement with the 2nd critical micelle concentration and the change points of the micellar structure determined by our previous report. Furthermore, the thermodynamic parameters of estriol solubilization were also discussed.
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Shoko YOKOYAMA, Yoshihiro FUJINO, Yoshiko KAWAMOTO, Akiko KANEKO, Tada ...
1994 Volume 42 Issue 6 Pages
1351-1353
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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The surface tension of an aqueous solution of piperidolate hydrochloride (PIH), which is an anti-cholinergic drug, was measured with a Du Nouy tensiometer at 25°C in the absence and presence of acetylcholine chloride(Ach·Cl), and the effect of Ach·Cl on the critical micelle concentration (cmc) of PIH was investigated by comparing it with the effects of sodium chloride (NaCl) and calcium chloride (CaCl
2). Furthermore, the effect of Ach·Cl on the cmc of PIH was discussed by comparing it with the effect of Ach·Cl on the cmc of dodecyltrimethylammonium chloride (DTAC). The value of cmc of PIH decreased with an increasing concentration of Ach·Cl. The order of the effect on the decrease in the cmc of PIH was CaCl
2>NaCl>Ach·Cl. The effect of Ach·Cl on the decrease in the cmc of PIH was smaller than that on the decrease in the cmc of DTAC.
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Masayuki YOSHIKAWA, Hisashi MATSUDA, Emiko HARADA, Toshiyuki MURAKAMI, ...
1994 Volume 42 Issue 6 Pages
1354-1356
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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A new inhibitor named elatosides E (which was shown to affect the elevation of plasma glucose level by oral sugar tolerance test in rats) was isolated from the root cortex of Aralia elata SEEM. together with elatoside F. The structures of elatosides E and F were elucidated on the basis of chemical and physicochemical evidence. The hypoglycemic activities of oleanolic acid and nine oleanolic acid glycosides obtained from the root cortex of Aralia elata heve been examined, and some structure-activity relationships have been found.
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Masayuki YOSHIKAWA, Emiko HARADA, Toshiyuki MURAKAMI, Hisashi MATSUDA, ...
1994 Volume 42 Issue 6 Pages
1357-1359
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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Five triterpene oligoglycosides named escins-Ia, Ib, IIa, IIb, and IIIa were isolated from the seeds of Aesculus hippocastanum L. and their chemical structures were determined on the basis of chemical and physicochemical evidence. Escins-Ia, Ib, IIa, and IIb were found to exhibit inhibitory effect on ethanol absorption and hypoglycemic activity on oral glucose tolerance test in rats. Among them, escins-IIa and IIb showed the higher activities for both bioassay, while desacylescins-I and II had no activity.
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Toshikazu SEKINE, Nobuaki FUKASAWA, Yumi KASHIWAGI, Nijsiri RUANGRUNGS ...
1994 Volume 42 Issue 6 Pages
1360-1362
Published: June 15, 1994
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A new cage-type alkaloid, asparagamine A (1), was isolated from the roots of Asparagus racemosus Willd. (Liliaceae). The relative stereostructure was elucidated by spectroscopic, chemical and single crystal X-ray analyses as a novel polycyclic pyrrolizidine derivative.
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Yoshiyasu KITAHARA, Fumiyasu TAMURA, Akinori KUBO
1994 Volume 42 Issue 6 Pages
1363-1364
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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A pentacyclic aza-aromatic alkaloid, meridine (1), was synthesized from 4-methoxy-5, 8-quinolinedione (4) and o-nitrocinnamaldehyde N, N-dimethylhydrazone (5) in four steps.
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Mugio NISHIZAWA, Hiroshi IMAGAWA, Eiko MORIKUNI, Susumi HATAKEYAMA, Hi ...
1994 Volume 42 Issue 6 Pages
1365-1366
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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A novel L-series cyclooligosaccharide, cyclo-L-rhamnopentaose, has been synthesized by means of successive glycosylation by Schmidt's imidate method and DMTST induced cycloglycosylation.
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Masanori SAKAMOTO, Asae NOZAKA, Mino SHIMAMOTO, Hideki OZAKI, Yoko SUZ ...
1994 Volume 42 Issue 6 Pages
1367-1369
Published: June 15, 1994
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Diels-Alder reactions of benzylidenecyanomethyl-1, 3-benzothiazoles and -1, 3-benzoxazoles 2a-f as 1-aza-1, 3-butadienes are described. The dienes 2, featuring the stabilized imine moieties by constituting heteroaromatic rings, react with both electron-deficient and electron-rich dienophiles 3a-c to give corresponding cycloadducts 4-6, regioselectively. The cycloadditions of the intramolecular systems 8a-d smoothly undergo via exo-transition state, stereoselectively affording polycyclic compounds 9a-d in good to excellent yields.
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Fumihiro NAGASHIMA, Shigeru TAKAOKA, Yoshinori ASAKAWA, Siegfried HUNE ...
1994 Volume 42 Issue 6 Pages
1370-1372
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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Three new rearranged ent-eudesmane-type sesquiterpene lactones, spirodilatanolides A (1), B (2) and C(3), and two new ent-eremophilane-type sesquiterpene lactones, dilatanolides A (4) and B (5), have been isolated and their absolute structures determined by extensive spectroscopic and X-ray crystallographic analyses.
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Takehiro SANO, Makiko KAMIKO, Jun TODA, Shinzo HOSOI, Yoshisuke TSUDA
1994 Volume 42 Issue 6 Pages
1373-1375
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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The detailed stereochemical pathway of [2+2] photocycloaddition reaction of isoquinolinodioxopyrroline to 2-(rtimethylsilyloxy)butadiene was clarified by using an enantiomerically pure substrate. The photoadducts were converted into the synthetic intermediates of Erythrina alkaloids, providing an efficient synthetic method in optically active forms.
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Toshihiro HASHIMOTO, Shigeo KANAYAMA, Yukiko KAN, Motoo TORI, Toshinor ...
1994 Volume 42 Issue 6 Pages
1376-1378
Published: June 15, 1994
Released on J-STAGE: March 31, 2008
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Two novel bis(bibenzyls) named paleatins A (1) and B (2) have been isolated from the liverwort, Marchantia paleacea var. diptera. Their structures have been establishied by a combination of high-resolution NMR spectra and chemical degradation. A total synthesis of paleatin A has been accomplished in ten steps.
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