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TAKESHI NAKAJIMA, MAKOTO SUNAGAWA, TOSHIYUKI HIROHASHI, KEIJI FUJIOKA
1984 Volume 32 Issue 2 Pages
383-400
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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Bencyclane (Ben) inclusion complexes with α-, β-, and γ-cyclodextrins (CyD's) in aqueous solution were studied by ultraviolet (UV), circular dichroism (CD), and nuclear magnetic resonance (NMR) spectroscopic methods. The composition ratio, the formation constants (K values), and the thermodynamic parameters for the three complexes were determined by analysis of the UV and CD spectra. The results indicated that CyD formed a 1 : 1 complex with Ben in all three cases, though the K values differed greatly (β>γ≫α). From the thermodynamic parameters obtained from the temperature dependence, it was concluded that the primary driving force for the complex formation is van der Waals interaction in the case of α- and β-CyD complexes, while it is hydrophobic interaction for the γ-CyD complex. Probable structures of the three complexes are discussed mainly on the basis of NMR data. It was concluded that the aromatic ring of Ben is inserted into the cavity of CyD from the small-diameter side in the case of β-or γ-CyD complexes, and from the opposite side in the case of α-CyD complex. It is highly probable that, in the case of β-CyD complex, binding is tight over the whole aromatic ring; in the case of γ-CyD complex, loose binding takes place over most of the aromatic ring and in the neighborhood of the benzyl carbon, with the para position of the aromatic ring extruding from the cavity; in the case of α-CyD complex, only partial inclusion occurs around the para position of the aromatic ring.
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TAKESHI NAKAJIMA, MAKOTO SUNAGAWA, TOSHIYUKI HIROHASHI
1984 Volume 32 Issue 2 Pages
401-408
Published: February 25, 1984
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The behavior of 1 : 1 inclusion complexes between cyclodextrins (CyD) and bencyclane (Ben) in a two-liquid-phase system of octanol and water was quantitatively investigated by measurement of partition coefficients (PC method). It was found that octanol partially prevents the formation of CyD·Ben complex and the apparent formation constant (K') was calculated from the apparent partition coefficient (P
*). This phenomenon was also observed in general with CyD 1 : 1 inclusion complexes of various drugs. The corrected formation constants (K) of these complexes in the aqueous phase were determined from the K' values by applying the equilibrium equations.
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HIROFUMI TAKEUCHI, YOSHIHISA MIWA, SHUSHI MORITA, JUTARO OKADA
1984 Volume 32 Issue 2 Pages
409-417
Published: February 25, 1984
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The bromide ion displacement reaction of n-octyl methanesulfonate catalyzed by polymerbound phosphonium ion was studied and the effects of the phosphonium ion content and the degree of cross-linking on the intrinsic activity and the intraparticle diffusion were examined. The catalysts were prepared by quaternization of chloromethylated polystyrene with tri-n-butylphosphine. All experiments were carried out in a stirred tank reactor in the temperature range from 60 to 90°C and at ambient pressure. The intrinsic rate of reaction was proportional to the concentration of n-octyl methanesulfonate, and gradually increased with the concentration of potassium bromide in the aqueous phase. The intrinsic activity decreased with increases in the phosphonium ion content and the degree of cross-linking. The liquid-to-solid mass transfer resistance was insignificant at stirring speeds above 400 rpm under the present conditions. The intraparticle diffusion of n-octyl methanesulfonate was found to be an important factor controlling the global rate of reaction. The effective diffusivity of n-octyl methanesulfonate in polymer resin decreased remarkably with increase in the degree of cross-linking.
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YASUSHI ITOI, MASAMI INOUE, SABURO ENOMOTO, YOSHIHIRO WATANABE
1984 Volume 32 Issue 2 Pages
418-423
Published: February 25, 1984
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By using molybdenum oxide fixed on active charcoal in the form of molybdenum blue, various alkenes of cyclopentene, cyclohexene, methylcyclohexene, styrene, methylstyrene, octene, and decene were selectively epoxidized with aqueous hydrogen peroxide (30%) in isopropyl alcohol. The yields increased in the presence of organotin compounds. Among them, tri-n-butyltin chloride gave good yields; cyclopentene and cyclohexene were epoxidized in yields of 71 and 60%, respectively. The catalyst could be separated by filtration and used repeatedly. By adjusting the pH value of the charcoal support with acid or base, both the epoxide yield and the selectivity could be varied widely, and good results were obtained between pH 6 and 7.
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TOKUJI OKAZAKI, MASAKATSU SHIBASAKI, SHIRO IKEGAMI
1984 Volume 32 Issue 2 Pages
424-429
Published: February 25, 1984
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The synthesis of both 9 (O)-methano-6α-prostaglandin-I
1 (9 (O)-methano-6α-PGI
1) and 9 (O)-methano-6β-prostaglandin-I
1 (9 (O)-methano-6β-PGI
1) has been accomplished via the same synthetic intermediate obtainable from 1, 3-cyclooctadiene. These analogs showed weak inhibitory activity in rabbit platelet aggregation induced by adenosine diphosphate. Furthermore, 9 (O)-methano-6β-PGI
1 did not show any cytoprotective action on rabbit, stomach epithelial cells at the concentration of 10
<-6 M.
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KENJI OKAMOTO, KOICHI YASUMURA, KAZUYOSHI FUJITANI, SHINICHI KATAKURA, ...
1984 Volume 32 Issue 2 Pages
430-437
Published: February 25, 1984
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Hylambatin, a dodecapeptide amide isolated from the skin of an African rhacopharid frog (Hylambates maculatus), was synthesized by two routes, by successive condensations of four fragments, i.e., (1-3), (4-5), (6-10), and (11-12) in one case and (1-3), (4-7), (8-10), and (11-12) in the other, followed by deprotection with 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The S-alkylation observable during N
α-deprotection of Metcontaining peptides with trifluoroacetic acid was found to be suppressed more effectively by the use of 3, 5-dimethylanisole containing 2% ethanedithiol as a scavenger system than by the use of anisole containing 2% ethanedithiol. The contractile potency of synthetic hylambatin in isolated guinea-pig duodenum was 0.42 times that of synthetic kassinin.
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YOSHIHARU ISHIKAWA, YOSHIYASU TERAO, KUNIO SUZUKI, NOBORU SHIKANO, MIN ...
1984 Volume 32 Issue 2 Pages
438-446
Published: February 25, 1984
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The present paper describes the finding that α- and β-alkylthio-substituted amines possessing a positively charged carbon such as =CHPh, CO
2R and CH
2SR at the nitrogen undergo cyclization in the presence of lithium diisopropylamide or sodium hydride leading to thiazolidines, thiomorpholines and dihydro-1, 4-benzothiazines.
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CHUZO IWATA, TETSUAKI TANAKA, TAKAFUMI FUSAKA, NAOYOSHI MAEZAKI
1984 Volume 32 Issue 2 Pages
447-451
Published: February 25, 1984
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The stereochemistry of the spirodienones (2) obtained by the intramolecular cyclization of methyl 2-bromo-5-(4-hydroxyphenyl) hexanoate (1) was established by carbon-13 nuclear magnetic resonance spectral analysis and chemical transformation to trans- and cis-1, 4-dimethyltetralins (6).
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JEAN CHARLES LANCELOT, SYLVAIN RAULT, MAX ROBBA
1984 Volume 32 Issue 2 Pages
452-456
Published: February 25, 1984
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Imidazo [4, 5-c] carbazoles are prepared by intramolecular cyclisation of 3, 4-diamino 9-ethylcarbazole and its derivatives. Proton magnetic resonance (
1H NMR) spectra are studied to confirm the proposed structures.
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SHIGEO AMEMIYA, KOICHI KOJIMA, KIYOSHI SAKAI
1984 Volume 32 Issue 2 Pages
457-462
Published: February 25, 1984
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Derivatives of dihydromethylenomycin A undergo a facile cleavage of the five-membered ring ketone and a subsequent reclosure to give 3 (2H)-furanone derivatives under weakly basic conditions such as in the presence of K
2CO
3. The structure of a typical product was unequivocally determined by synthesis. The reaction mechanism is discussed.
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MASATO SHIMIZU, MASAYUKI ISHIKAWA, YASUO KOMODA, TERUMI NAKAJIMA, KEII ...
1984 Volume 32 Issue 2 Pages
463-474
Published: February 25, 1984
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The Pictet-Spengler reaction of N
a-methyl-N
b-benzyltryptophan methyl ester hydrochloride (4a) with methyl 3-formylpropionate was carried out in 50% aqueous MeOH under reflux to afford methyl trans-2-benzyl-3-methoxycarbonyl-9-methyl-1, 2, 3, 4-tetrahydro-9H-pyrido [3, 4-b] indole-1-propionate (3a) as a major product and trans-2-benzyl-3-methoxycarbonyl-9-methyl-1, 2, 3, 4-tetrahydro-9H-pyrido [3, 4-b] indole-1-propionic acid (5a) as a minor product. In earlier work, the stereochemistry of the major product 3a had been erroneously assigned as 1, 3-cis (3b), while the minor product 5a had been incorrectly assigned as the 1, 3-trans compound 3a. Compound 3b was not formed in this reaction. The stereochemistry of the major product (3a) was confirmed by X-ray crystallographic analysis in the present work.
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YOSHIHISA ASADA, TSUTOMU FURUYA
1984 Volume 32 Issue 2 Pages
475-482
Published: February 25, 1984
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Four new pyrrolizidine alkaloids, ligularidine, neoligularidine, ligularizine and ligularinine, were isolated together with the known compound clivorine from the roots and aerial parts of Ligularia dentata. Their structures were elucidated on the basis of the spectral data and chemical conversion of clivorine into these alkaloids. A useful epoxidation of pyrrolizidine alkaloids was achieved by using performic acid.
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GENICHIRO NONAKA, KANJI ISHIMARU, TAKASHI TANAKA, ITSUO NISHIOKA
1984 Volume 32 Issue 2 Pages
483-489
Published: February 25, 1984
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Together with 2', 5-di-O-galloylhamamelose (I), which had previously been designated as hamamelitannin, five new galloylhamameloses (II-VI) were isolated from the bark of Castanea crenata L. (Fagaceae). On the basis of chemical and spectroscopic evidence, their structures were characterized as 2', 3, 5-tri-O-galloyl-(II), 5-O-galloyl-(III), 1, 2'-di-O-galloyl-(IV), 1, 2', 5-tri-O-galloyl-(V) and 1, 2', 3, 5-tetra-O-galloyl-D-hamamelofuranose (VI). In addition, the occurrence of two galloylhamameloses (I and II) in the underground part of Sanguisorba officinalis L. (Rosaceae) was demonstrated.
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NOBUTOSHI TANAKA, TAKURO SADA, TAKAO MURAKAMI, YASUHISA SAIKI, CHIUMIN ...
1984 Volume 32 Issue 2 Pages
490-496
Published: February 25, 1984
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The fronds extracts of Glaphyropteridopsis erubescens (WALL.) COPEL. contain besides the already known flavonol glycosides (afzelin and quercitrin) three new flavan-4-ol glycosides, eruberin A (I), B (II) and C (III), which belong to a new type of proanthocyanidin. By means of spectroscopic and chemical methods, the structures 5, 7-dihydroxy-4'-methoxy-6, 8-dimethyl-2", 4 (S)-oxido-2 (R)-flavan-5-β-D-glucopyranoside (I), 4 (S), 5, 7-trihydroxy-4'-methoxy-6, 8-dimethyl-2 (R)-flavan-5, 7-O-β-D-diglucopyranoside (II) and 5, 7-dihydroxy-4 (S), 4'-dimethoxy-6, 8-dimethyl-2 (R)-flavan-5, 7-O-β-D-diglucopyranoside (III) are proposed. Eruberin C (III) may be an artifact.
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TAKEHIRO SANO, YOSHIE HORIGUCHI, JUN TODA, KAZUE IMAFUKU, YOSHISUKE TS ...
1984 Volume 32 Issue 2 Pages
497-503
Published: February 25, 1984
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2-Aryl-3-ethoxycarbonyl-Δ
2-pyrroline-4, 5-diones (3) were easily prepared in good yields by condensation of the enamino-esters (2) with oxalyl chloride. The products were characterized by ultraviolet and infrared spectroscopy.
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YOSHIHIRO SATO, TAIKO ODA, JUNKO INOUE, MASAYUKI KUNUGI, KAZUO T. SUZU ...
1984 Volume 32 Issue 2 Pages
504-509
Published: February 25, 1984
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The stereochemistry of microbial transformation of (-)-α-santonin (1) by Streptomyces cinereocrocatus is described. Fermentation of (-)-α-santonin (1) with S. cinereocrocatus led to the formation of (+)-1, 2-dihydro-α-santonin (2). To elucidate the stereochemistry of the microbial hydrogenation of (-)-α-santonin, (-)-[1, 2-
2H]-α-santonin (1a) was synthesized from 1, and subjected to the microbial transformation. Analysis of the 400 MHz proton nuclear magnetic resonance spectrum of the deuterated product clearly revealed that the microbial hydrogenation of 1a proceeds stereo-specifically with trans-addition of hydrogens via si face attacks at the 1 and 2 positions.
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NOBUTAKA FUJII, MASANORI SHIMOKURA, KENICHI AKAJI, SHINYA KIYAMA, HARU ...
1984 Volume 32 Issue 2 Pages
510-519
Published: February 25, 1984
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As a starting material for the solution synthesis of a tetratetracontapeptide amide corresponding to the entire sequence of growth hormone releasing factor derived from human pancreatic tumor, a C-terminal-protected docosapeptide amide (positions 23-44) was synthesized by successive azide condensation of three peptide fragments (positions 33-44, 28-32, and 23-27). Amino acid derivatives bearing protecting groups removable by trifluoromethanesulfonic acid were employed; i.e., benzyloxycarbonyl (Z), benzyl (Bzl), and mesitylene-2-sulfonyl (Mts).
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NOBUTAKA FUJII, MASANORI SHIMOKURA, MOTOYOSHI NOMIZU, HARUAKI YAJIMA, ...
1984 Volume 32 Issue 2 Pages
520-529
Published: February 25, 1984
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The tetratetracontapeptide corresponding to the entire amino acid sequence of growth hormone releasing peptide derived from human pancreas islet tumor was synthesized by assembling eight peptide fragments in a conventional manner, followed by thioanisole-mediated deprotection with 1 M trifluoromethanesulfonic acid in TFA. Our synthetic peptide significantly stimulated the release of immunoreactive growth hormone in vivo.
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SOJI SUGAI, KAZUO SATO, KUMIKO KATAOKA, YUKIKO IWASAKI, KAZUO TOMITA
1984 Volume 32 Issue 2 Pages
530-537
Published: February 25, 1984
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New versatile syntheses of 3-aminoisoxazoles and their derivatives are described. 3-(N, N-Disubstituted amino) isoxazoles 5 were synthesized by heating 3-chloro-2-methylisoxazolium chlorides 1 with secondary amines, or by the substitution reaction of 1 with primary amines, followed by the dehydrochlorination and the subsequent addition-elimination reaction of alkyl or acyl halides with the resulting imines 6. Among the products 5, 3-(N-substituted acetylamino) isoxazoles were hydrolyzed with base to give 3-(N-monosubstituted amino) isoxazoles 3. 3-Aminoisoxazoles 7 were synthesized by the reaction of 1 with potassium phthalimide, followed by treatment with hydrazine.
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MASAZUMI IKEDA, MASAMI TAKAHASHI, TAKAMASA UCHINO, YASUMITSU TAMURA
1984 Volume 32 Issue 2 Pages
538-542
Published: February 25, 1984
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Photoirradiation of 2-(3-butenoyloxy)-and 2-(4-pentenoyloxy) cyclohex-2-enones resulted in the formation of 2-oxabicyclo [3. 2. 0] heptan-3-one and 2-oxabicyclo [4. 2. 0] octan-3-one derivatives (head-to-head adducts), respectively.
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KAZUNOBU HARANO, FUMIHIRO SUEMATSU, TOSHIKAZU MATSUOKA, TAKUZO HISANO
1984 Volume 32 Issue 2 Pages
543-552
Published: February 25, 1984
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To provide additional evidence for the concerted mechanism postulated for the 1, 3-dipolar cycloaddition reaction of pyridine N-oxides with phenyl isocyanates, kinetic studies on the cycloaddition reactions were conducted in a variety of solvents. The cycloaddition showed low sensitivity to the ionizing power of the medium, indicating that it proceeds by a mechanism which involves very little change in charge separation between the ground state and the transition state. The observed cycloadditivity and site selectivity are discussed in terms of the following controlling factors based on MINDO/3 calculations : HOMOLUMO control, secondary orbital interaction, steric interaction, dipole-dipole interaction and charge-transfer complexation.
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AKIRA SHIOZAWA, YUHICHIRO ICHIKAWA, CHIKARA KOMURO, GENICHI IDZU, MICH ...
1984 Volume 32 Issue 2 Pages
553-563
Published: February 25, 1984
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A series of 2-(2-aminoethyl) pyridines derived by the modification of the amine moiety in betahistine, 2-(2-methylaminoethyl) pyridine, was synthesized and evaluated for antivertigo action in terms of inhibitory activity against spontaneous nystagmus in cats. The structure-activity relationships between the amine moieties and antivertigo activities were investigated. The effects of substituents on the phenyl ring of the 4-phenylpiperazine moiety were investigated by means of quantitative regression analysis using various physicochemical parameters. The following equation gave the best correlation. log 1/ID
30=-0.417 (±0.322) π+0.166 (±0.048) MR-1.473 (±0.237) (n=15, s=0.239, r=0.910, F
212=28.887). In this series of compounds, 1-(2-methoxyphenyl)-4-[2-(2-pyridyl) ethyl] piperazine, 1-(2-methoxyphenyl)-4-[2-[2-(6-methyl) pyridyl] ethyl]-piperazine, and 1-(2-methoxyphenyl)-4-[2-[2-(5-ethyl) pyridyl] ethyl] piperazine were found to show more potent activity than betahistine. Thus, the 4-(2-methoxyphenyl) piperazine group was found to be the most effective amine moiety for activity against spontaneous nystagmus.
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MICHIKO MIYAHARA, MAKOTO MIYAHARA, SHOZO KAMIYA
1984 Volume 32 Issue 2 Pages
564-570
Published: February 25, 1984
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Administration of 1, 3-diaryl-1-nitrosoureas (I) prolonged the life span of rats inoculated intraperitoneally with ascites hepatoma AH13 cells. Active species produced from compound I were aryl diazonium ion, aryl isocyanate and nitrosonium ion. These species reacted with adenine, guanine, L-lysine, and the SH group of N-acetyl-DL-penicillamine. A possible anti-AH13 action mechanism of 1, 3-diaryl-1-nitrosoureas in proposed to be as follows. The nitrosoureas (I) permeate quickly into the cytoplasm or nucleus, and decompose to give an active intermediate, an aryl diazonium ion, which reacts with nucleic acids of tumor cells to form a deoxyribonucleic acid (DNA) adduct, followed by tumor cell death. DNA repair of other damaged cells is inhibited by aryl isocyanate and nitrosonium ion liberated from compound I, which reacts with repair enzyme to form carbamoylated and S-nitrosated enzyme.
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YOSHIKI MINO, YASUYUKI TSUKIOKA, NAGAYO OTA
1984 Volume 32 Issue 2 Pages
571-577
Published: February 25, 1984
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Inorganic constituents of many licorice roots (55 samples; almost all obtained commercially in Osaka market) were investigated using energy-dispersive X-ray fluorescence spectrometry. The results can be summarized as follows : (1) Most of the elemental contents of each licorice root showed considerable variation. (2) Many licorice roots contained Sr at a high level, and the contents of Sr and K were dependent on the geographical source of the root, i. e., the producing district (Seihoku or Tohoku). (3) The metals profile of each crude drug provides valuable information regarding the identification of not only the kind of crude drug but also the producing district or the original plant.
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TAMOTSU NIKAIDO, YEOLIK SUNG, TAICHI OHMOTO, USHIO SANKAWA
1984 Volume 32 Issue 2 Pages
578-584
Published: February 25, 1984
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Cyclic adenosine 3', 5'-monophosphate (AMP) phosphodiesterase inhibitors present in the culms of Phyllostachys nigra MUNRO var. henonis STAPF. and the rhizomes of Phragmites communis TRIN. (Gramineae) were identified as 2, 5-dimethoxy-p-benzoquinone, p-hydroxybenzaldehyde, syringaldehyde, coniferylaldehyde, vanilic acid, ferulic acid and p-coumaric acid. The structure-activity relationship was investigated with 12 derivatives of p-benzoquinone, 22 derivatives of benzaldehyde, 10 derivatives of benzyl alcohol, 24 derivatives of benzoic acid and 32 derivatives of C
6-C
3 related compounds.
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HIROSHI TERADA, YUKIE INOUE, TETSUO ICHIKAWA
1984 Volume 32 Issue 2 Pages
585-590
Published: February 25, 1984
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The 2nd derivative spectra of tryptophan and tyrosine, and of ribonuclease (as a tyrosine-rich protein) and lysozyme (as a tryptophan-rich protein) were recorded under various conditions. On the basis of these spectra, the spectral bands of tryptophan and tyrosine residues in proteins were analyzed. Furthermore, the effects of the anionic surfactant sodium dodecyl sulfate on the environment around tryptophan and tyrosine residues in bovine serum albumin were studied.
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YOSHIKI MINO, NAGAYO OTA
1984 Volume 32 Issue 2 Pages
591-599
Published: February 25, 1984
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A convenient method requiring only one standard material was developed for the multielemental analysis (20 elements) of crude drug samples by energy-dispersive X-ray fluorescence spectrometry. The analytical method was based on the principle that when a sample powder is shaped into a very thin pellet, the excitation effect of the matrix is negligible, and a correction factor for the matrix absorption effect can be obtained by mathematical treatment. Percentage accuracies are better than ±10%, and detection limits are in the low ppm range for most elements. The present method is suitable for the examination of metal-containing profiles of many crude drug samples because of its ease of application. Several samples were analyzed and each crude drug was found to apparently have a characteristic metal profile.
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MASATAKA MORIYASU, MASARU ENDO, YOHEI HASHIMOTO, TAKEMI KOEDA
1984 Volume 32 Issue 2 Pages
600-608
Published: February 25, 1984
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The reaction of Ni (II) dithiocarbamate chelate formation was applied as a color reaction in high-performance liquid chromatography (HPLC) analysis of aliphatic primary and secondary amines. The reaction proceeded quantitatively and almost instantaneously at room temperature in alkaline media. The deep yellow (logε=4.5 at 325 nm) reaction products were extractable with organic solvents and gave sharp peaks on both normal-phase and reverse-phase chromatography. This method was applied to the microdetermination of stimulant drugs, e.g. methamphetamine and amphetamine, in urine, and as little as 1 ng of these drugs could be detected.
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RIKIO IKENISHI, TAKAYASU KITAGAWA, EIZO HIRAI
1984 Volume 32 Issue 2 Pages
609-617
Published: February 25, 1984
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In connection with our studies to develop an assay method for 4-chloro-2-(o-chlorobenzoyl)-N-methyl-N
α-glycylglycinanilide (1), a colored substance formed by the reaction of 1 with the reagent 3, 5-dibromosalicylaldehyde (DBSA) was isolated and its chemical structure was investigated. Another colored substance formed by the same reaction of glycinemonomethylamide (3) with DBSA was also isolated, and the chromophoric structure was shown to be essentially the same as that of the compound formed in the reaction of 1 with DBSA. On the basis of spectrometric and chemical evidence, the colored compounds were determined to be N-substituted 5-(3, 5-dibromo-2-hydroxybenzylidene)-2-(3, 5-dibromo-2-hydroxyphenyl)-1-imidazoline-4-ones. The reaction mechanism of the coloration in the assay of 1 is discussed.
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MITSUTERU NUMAZAWA, MASAO NAGAOKA, MIEKO OGATA
1984 Volume 32 Issue 2 Pages
618-622
Published: February 25, 1984
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Synthesis of 1, 3, 5 (10)-estratriene-3, 16α, 17β-triol-d
6 and -d
7 (4), 3, 16α-dihydroxy-1, 3, 5 (10)-estratrien-17-one-d
5 (5) and sodium 3, 17β-dihydroxy-1, 3, 5 (10)-estratrien-16α-yl-β-D-glucopyranosuronate-d
6 (8) is described. Treatment of 2, 4, 16α-tribromo-3-hydroxy-1, 3, 5 (10)-estratrien-17-one (1) with sodium hydroxide-OD in deuterium oxide-pyridine under controlled conditions gave the [16β-
2H] 16α-hydroxy-17-one (2). The ketol 2 was converted into the triol-d
6 (4) via sodium borodeuteride reduction in the presence of palladium chloride. Similar treatment of the 17-ethyleneacetal of 2 followed by acid hydrolysis gave compound 5-d
5. Reaction of 2 with methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranosuronate using silver carbonate as a catalyst yielded the 16-monoglucuronide acetate methyl ester (6). The reductive removal of the bromines of 6 and subsequent alkaline hydrolysis gave the glucuronide-d
6 (8). Mass spectrometric analysis showed compounds 4, 5, and 8 to have good isotopic purity.
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HIROSHI HAMADA, MIYUKI YAMASHITA, MISAO KOJIMA, TAMOTSU MORITA
1984 Volume 32 Issue 2 Pages
623-627
Published: February 25, 1984
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The effect of methanol on the induction of cytoplasmic respiration-deficient (RD) mutants of Saccharomyces cerevisiae by acriflavine (AF) was investigated. After 24 h incubation, AF at above 0.5μg/ml induced approximately 100% RD mutants in surviving cells. Methanol prevented the RD mutation by AF at concentrations less than 1.5μg/ml. The RD mutation by 0.15μg/ml AF was completely repressed by the addition of 4.0% methanol to the culture fluid. The induction frequency of RD mutants by 0.5μg/ml AF was reduced from 97 to 15% by the addition of 8.0% methanol. The AF uptake by the yeast cells was decreased in the presence of methanol. However, this methanol-induced repression in the RD mutation could not be explained simply in terms of the decrease of AF content in the yeast cells.
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HAJIME INOUE, YOSHIYUKI SEYAMA, SABURO YAMASHITA, SHOGO TOKUDOME
1984 Volume 32 Issue 2 Pages
628-630
Published: February 25, 1984
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Arylsulfatase B (AS-B) activity was isolated from the human lung. AS-B activity has been reported to be homogeneous on disc electrophoresis after ion-exchange chromatography, but in the present study, a highly purified (approx. 2000-fold increase as compared with the previously reported 170-fold increase of specific activity) fraction was found to be still heterogeneous on a chromatofocusing column.
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TOSHIAKI KOIZUMI, YASUHIRO YAMANE
1984 Volume 32 Issue 2 Pages
631-637
Published: February 25, 1984
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The protective mechanism of Na
2MoO
4 against the acute toxicity of HgCl
2 was studied by investigating the subcellular distributions of mercury and molybdenum in the liver and kidney of rats treated with either Na
2MoO
4 or HgCl
2 or both, and by performing Sephadex G-75 gel chromatography of the liver and kidney cytosol obtained from these groups. The rats given HgCl
2 (0.03mmol/kg, once, s.c.) after pretreatment with Na
2MoO
4 (1.24mmol/kg, once a day for 3d, i.p.) has decreased the mercury contents in the liver mitochondrial and microsomal fractions and in the renal nuclear fraction, in comparison with those of the rats given HgCl
2 alone. However, the mercury content in the renal cytosol of this group was increased in comparison with that of the rats given HgCl
2 alone. A gel filtration study showed that the increase in mercury content of the renal cytosol of the rats pretreated with Na
2MoO
4 was associated with an increase in the metal content in the metallothionein-like fraction. These results suggest that molybdenum alleviated the acute HgCl
2 toxicity not only by reducing the mercury contents in the mitochondrial and microsomal fractions of liver and in the nuclear fraction of kidney, but also by enhancing the retention of mercury in the renal metallothionein-like fraction.
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KIYOMI KIKUGAWA, SHIGENOBU WATANABE, TSUTAO KURECHI
1984 Volume 32 Issue 2 Pages
638-645
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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Unsaturated fatty acids such as linoleic, linolenic and arachidonic acids produced a complex mixture of fluorescent substances with an excitation maximum at 355-370nm and an emission maximum at 420-440nm by reaction with methylamine at pH 7.5 and 37°C. The excitation and emission maxima of the products shifted to higher wavelength with increasing unsaturation of the fatty acid, and were similar to those of lipofuscin pigments. The fluorescence characteristics of the products indicated that they were different in structure or composition with different fatty acids, and the major fluorescent products were neither 1-substituted-4-methyl-1, 4-dihydropyridine-3, 5-dicarbaldehydes [Kikugawa et al., Chem. Pharm. Bull., 29, 1423 (1981)] nor the conjugated Schiff bases [Chio and Tappel, Biochemistry, 8, 2821 (1969)] which were produced by reaction of malonaldehyde (MDA) with primary amines. Both thin-layer and high performance liquid chromatographies suggested that thiobarbituric acid-reactive substances other than MDA contributed to the formation of the fluorescent substances.
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EIKO ONISHI, KAZUO YAMADA, TOSHIO YAMADA, KIYOKO KAJI, HAJIME INOUE, Y ...
1984 Volume 32 Issue 2 Pages
646-650
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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Aqueous extracts of leaves of Nelumbo nucifera, GAERTN. (Nymphaeceae), Kayo, leaves and stems of Lonicera japonica THUNB. (Caprifoliaceae) Nindo and stems of Akebia quinta (THUNB.) DECNE (Lardiazabalaceae) Mokutsu were administered to rats loaded with a high fat diet containing 1.5% cholesterol and 1.0% cholic acid in order to screen the hypocholesterolemic activity of these crude drugs. The animals were kept on the diet for 5d, and then crude drug extract, equivalent to the human dose (×1) and higher doses (×10, ×25), was orally administered. Changes of total cholesterol (TC), free cholesterol (FC), cholesterol ester (CE), free and ester cholesterol ratio (Ratio), triglycerides (TG), phospholipid (PL) and free fatty acids (NEFA) were examined. Significant decreases in serum TC, FC, and PL were observed in the high fat-loaded groups given these crude drugs. TC in the liver did not show any reduction in the groups receiving Kayo, Nindo and Mokutsu as compared with the high fat-loaded control group. The overall effects in suppressing serum lipids elevation were in the order of Nindo > Mokutsu > Kayo.
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KAZUNOBU MIURA, TOHRU UEDA, NARIKO SHINRIKI, KOZO ISHIZAKI, FUMIO HARA ...
1984 Volume 32 Issue 2 Pages
651-657
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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The treatment of transfer ribonucleic acids (tRNAs) with ozone and subsequent treatment with aniline-acetate (pH 4.5) resulted in the internucleotidic bond cleavage of tRNAs. Sequence analysis of the fragments obtained showed that the internucleotidic bond-cleavage occurred at the guanine residues modified with ozone, and the most susceptible sites were those in consecutive sequences of guanine residues, such as -GpGpGpGp- and -GpGp
m1Gp-in tRNA
Pro.
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KEIJI SEKIGUCHI, ETSUKO SUZUKI, YASUYUKI TSUDA, KENICHI SHIROTANI, KIK ...
1984 Volume 32 Issue 2 Pages
658-664
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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It was formerly believed that when a binary compound dissociates extensively on fusion, parts of the solidus and liquidus of the system become horizontal and therefore parallel. Since this is unacceptable in terms of the phase rule, thermal analysis was carried out with the picric acid-m-hydroxybenzaldehyde and naphthalene-m-dinitrobenzene systems which were hitherto considered as typical examples of such systems. The phase diagrams reconstructed by the improved thaw-melt method showed two eutectic lines, closely adjacent but distinctly different. In both cases, the melting curves consisted of three parts and the central ones were gently curved but had maximums at equimolar composition. Thus, it is certain that these systems belong to the category forming a congruently melting compound with a combining ratio of 1 : 1, and that the so-called parallelism resulted from a lack of experimental accuracy and/or rather arbitrary drawing of the phase diagrams in the past. In addition to the visual method, measurements by differential thermal analysis (DTA) and differential scanning calorimetry were done with the latter system. It was found that the melting point could not be determined in several cases; however, differentiation of the two close eutectic points was possible at a sufficiently slow rate of heating. Also, a small heat effect due to the metastable eutectic liquefaction was often recorded on the DTA curves. These findings show that the instrumental methods are useful for detecting the binary compound but by themselves are unsuitable for constructing the phase diagram of such a system.
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EVA FENYVESI, OSAMU SHIRAKURA, JOZSEF SZEJTLI, TSUNEJI NAGAI
1984 Volume 32 Issue 2 Pages
665-669
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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The binding and disintegrating properties of cyclodextrin polymer as well as its effect on the dissolution of a poorly soluble drug have been evaluated on the basis of the hardness, friability and disintegration time of directly compressed tablets. The hardness of tablets containing cyclodextrin polymer in addition to potato starch or lactose was lower than that of tablets with microcrystalline cellulose indicating that cyclodextrin polymer has a relatively poor binding capacity. The disintegrating action of cyclodextrin polymer was compared to those of potato starch and lactose, with microcrystalline cellulose as a binder. Equal disintegration times were obtained with 2.5% cyclodextrin polymer, 12.5% potato starch, and 25% lactose. The dissolution rate of furosemide was greatly accelerated by as little as 2.5% cyclodextrin polymer added to microcrystalline cellulose. A somewhat lower dissolution rate was observed with 12.5% potato starch. As a result it was shown that cyclodextrin polymer, which has excellent disintegrating properties as well as some binding capacity, can be used advantageously in direct compression systems as a binder-disintegrant.
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EVA FENYVESI, KOZO TAKAYAMA, JOZSEF SZEJTLI, TSUNEJI NAGAI
1984 Volume 32 Issue 2 Pages
670-677
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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The effectiveness of cyclodextrin polymer as a disintegrating agent for directly compressed tablets containing furosemide, cyclodextrin polymer and microcrystalline cellulose was investigated. Regression analysis based on statistically designed experiments made it possible to determine how various tablet characteristics are affected by the amount of excipients. As a result of computer optimization an optimum formulation was obtained exhibiting high dissolution rate, sufficient dissolution stability, fast disintegration, high hardness immediately after preparation and adequate hardness after ageing.
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FUMIYOSHI ISHII, AKIRA TAKAMURA, SHUNICHI NORO
1984 Volume 32 Issue 2 Pages
678-684
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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The preparation of anticancer agent-loaded microcapsules magnetically responsive to applied magnetic fields is described, together with some biophysical and biochemical data. The ethylcellulose-walled microcapsules containing magnetite (Fe
3O
4, as a ferrofluid) and anticancer agents had a diameter of 0.2-0.6μm (mean diameter, 0.308μm). The retention of these microcapsules by magnetic fields was measured in an in vitro model of the human circulation system. The apparatus provided steady flow at various rates through various types of horizontally mounted glass capillary tubes. The retention of magnetically responsive microcapsules was also evaluated in terms of the Reynolds number. The microcapsules prepared in this experiment were caught and held with high efficiency at specific sites within a large artery model by using external permanent or electric magnets, and further, the captured microcapsules did not aggregate irreversibly when the electric field was removed.
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YOSHINOBU NAKAI, KEIJI YAMAMOTO, KATSUHIDE TERADA, KATSUYA AKIMOTO
1984 Volume 32 Issue 2 Pages
685-691
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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Aspirin, benzoic acid and p-hydroxybenzoic acid, all of which form intermolecularly hydrogen-bonded dimer structures in the crystalline form, were ground with α- or β-cyclodextrin. Inclusion compounds were also prepared by the coprecipitation method, except in the case of the aspirin-α-cyclodextrin system. The dispersed state of the medicinal molecules were investigated by analysis of the infrared spectra in the carbonyl stretching regions. It was suggested that the dispersed state of medicinals in the α-cyclodextrin system was different from that in the β-cyclodextrin system. It was assumed that, by grinding, aspirin molecules were included in the cyclodextrin cavity in the β-cyclodextrin system, but were dispersed monomolecularly in the hydrogen-bonded network structure of cyclodextrin in the α-cyclodextrin system. Interaction between medicinals and α- or β-cyclodextrin in aqueous solution was investigated by means of nuclear magnetic resonance studies. The sublimation of p-hydroxybenzoic acid from the ground mixtures or inclusion compounds with α- or β-cyclodextrin systems was determined by thermogravimetry. The effects of cyclodextrin on the hydrolysis of aspirin under acidic conditions were investigated as well.
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NOBUHARU KAKEYA, KENICHI NISHIMURA, AKIHISA YOSHIMI, SYOHEI NAKAMURA, ...
1984 Volume 32 Issue 2 Pages
692-698
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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p-Glycyloxy-, o-glycylamino- and p-glycylaminobenzoyloxymethyl esters of 7β-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-methyl-3-cephem-4-carboxylic acid (1) were synthesized as prodrugs designed to improve the oral absorption of the parent cephalosporin. The esters were found to possess the desired factors for an orally active prodrug, that is, appropriate solubility, lipophilicity and lability. As predicted from these factors, the esters when administered orally to mice were well absorbed from the gastrointestinal tract and gave high blood levels of the parent compound (1).
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NAOMI I. NAKANO, YOSHIMITSU SHIMAMORI, MISAKO UMEHASHI, MASAHIRO NAKAN ...
1984 Volume 32 Issue 2 Pages
699-707
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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An activated carbon preparation suitable for oral administration as an intestinal adsorbent was prepared by drying spherical beads of 48 to 250 mesh in which 8% activated carbon powder was dispersed. The final preparation, dried activated carbon beads containing about 67% activated carbon in agar, consists of fine granules with good flow properties and is free from many of the handling problems associated with fine charcoal powders. The in vitro adsorption characteristics of the original fine powder were essentially retained when salicylic acid and acetaminophen were used as adsorbates, including the rate of adsorption and the enhancing effect of sodium chloride on the adsorption of salicylate ions. Administration of the beads to rats caused a statistically significant reduction in plasma salicylate level at about 2 h after administration, and no greater reduction was observed with the powder. These results indicate that the preparation is a promising candidate as an intestinal adsorbent.
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KAZUYUKI HIRANO, YOSHIHITO WATANABE, TETSUO ADACHI, MAMORU SUGIURA
1984 Volume 32 Issue 2 Pages
708-715
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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The bilirubin-binding abilities of human serum albumin, α-fetoprotein and ligandin were investigated by employing absorbance spectral measurement, peroxidation and fluorescence measurement techniques. The binding constants of the proteins from adult serum and cord serum were very similar. However, those of α-fetoprotein were slightly smaller than those of albumin. Ligandin had two cooperative binding sites for bilirubin, and the binding constants were of the same order as those of the weaker binding sites of albumin. A study of the effect of linolic acid revealed that the bilirubin bound to α-fetoprotein was more easily liberated in the presence of linolic acid than that bound to albumin binding. The drug-binding abilities of these proteins were also examined, and no significant difference was found between adult serum and cord serum albumins. However, α-fetoprotein appeared not to exhibit drug-binding ability when the peroxidation method was employed. The biological role of α-fetoprotein in fetal plasma may be similar to that of albumin.
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MASAKI SATO, KIMIE IMAI, RYOHEI KIMURA, TOSHIRO MURATA
1984 Volume 32 Issue 2 Pages
716-722
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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When sodium copper chlorophyllin (Cu-Chl-Na) was given intraperitoneally to rats (two doses of 50 or 100mg/kg at 18 and 2h prior to sacrifice), the ascorbic acid-dependent lipid peroxidation in both mitochondria and microsomes of the liver markedly decreased. The microsomal lipid peroxidation induced by reduced nicotinamide adenine dinucleotide phosphate (NADPH) was also depressed by the treatment with Cu-Chl-Na. In addition, the soluble fraction of liver in injected animals showed an inhibition of the ascorbic acid- and NADPH-stimulated lipid peroxidation in hepatic microsomes from untreated rats. The absorption spectrum of each subcellular fraction in liver from Cu-Chl-Na-treated rats showed a red absorption band with a peak at ca. 633nm, which is characteristic of the copper complexes of chlorophyll derivatives. These findings suggest that the administered Cu-Chl-Na or substance (s) derived from Cu-Chl-Na is taken into the liver and distributed among the mitochondria, microsomes and soluble fraction in an active form functioning as an antioxidant. Subsequently, a single injection of Cu-Chl-Na was observed to prevent effectively the impairment of hepatic microsomal functions (as indicated by the depression of glucose-6-phosphatase and drug-metabolizing enzyme system) resulting from ascorbic acid-induced lipid peroxidation.
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AINA LAO, YASUO FUJIMOTO, TAKASHI TATSUNO
1984 Volume 32 Issue 2 Pages
723-727
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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Twelve compounds were isolated from Artemisia argyi, LEVL et VANT (Compositae) collected in China : ethyl palmitate, ethyl oleate, ethyl linoleate, lupenone, lupenyl acetate, α-amyrin acetate, β-amyrin acetate, glutinone, fernenone, 24-methylene-cycloartanone, simiarenol and trans-phenylitaconic acid. This is the first report of the isolation of trans-phenylitaconic acid from a natural souce.
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TAKAO SAKAMOTO, HIROSHI YOSHIZAWA, SOHICHI KANEDA, HIROSHI YAMANAKA
1984 Volume 32 Issue 2 Pages
728-732
Published: February 25, 1984
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The reaction of 2-methyl-and 4-methylpyrimidine N-oxides with acetic anhydride proceeded smoothly in benzene solution to give 2-acetoxymethyl- and 4-acetoxymethylpyrimidines, respectively. The same reaction of 4-methoxy-2, 6-dimethylpyrimidine 1-oxide afforded 2-acetoxymethyl-4-methoxy-6-methylpyrimidine as a sole product. Other examples of such siteselective acetoxylation of pyrimidine N-oxides are also described.
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SHOICHIRO OZAKI, YUTAKA WATANABE, TOMONORI HOSHIKO, HARUO MIZUNO, KATS ...
1984 Volume 32 Issue 2 Pages
733-738
Published: February 25, 1984
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The toxicity and tumor affinity of 5-fluorouracil (1) have been modified by the introduction of acyloxyalkyl group (s) at the 1-, 3- or 1, 3-position (s) of 1. 1-Acyloxyalkyl-5-fluorouracil (3), 3-acyloxyalkyl-5-fluorouracil (4) and 1, 3-bis (acyloxyalkyl)-5-fluorouracil (5) were obtained by three methods : i) the reaction of α-chloroalkyl carboxylate (2) with 1, ii) the reaction of alkylidene diacylate with 2, 4-bis (trimethylsilyloxy)-5-fluoropyrimidine, iii) partial hydrolysis of 5. Compounds 3, 4 and 5 showed antitumor activity.
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NOBUTAKA FUJII, WI LEE, MASANORI SHIMOKURA, HARUAKI YAJIMA
1984 Volume 32 Issue 2 Pages
739-743
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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A hybrid heptacosapeptide amide, consisting of growth hormone releasing factor (GRF) tetradecapeptide (1-14) and PHI tridecapeptide (15-27), was synthesized by a fragment condensation procedure, followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The synthetic peptide exhibited in vivo GRF activity (ca. 1/10 of that of GRF-44-NH
2), but lacked the blood pressure-decreasing activity of the parent PHI.
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MASATAKA MORIYASU, MASARU ENDO, RITSUKO KANAZAWA, YOHEI HASHIMOTO, ATS ...
1984 Volume 32 Issue 2 Pages
744-747
Published: February 25, 1984
Released on J-STAGE: March 31, 2008
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High-performance liquid chromatographic (HPLC) analysis of ephedrine, pseudoephedrine, norephedrine and pseudonorephedrine in some Ephedra species was carried out. Color reaction of these bases by the formation of Ni (II) dithiocarbamate chelates facilitated microdetermination of these based at levels of less than 1 ng. This method was applied to the analysis of these bases in some Ephedra species. The present method is so sensitive that analysis of these bases in Pinelliae Tuber was also possible, and peaks corresponding to pseudoephedrine, norephedrine and pseudonorephedrine appeared on the chromatograms along with the peak of ephedrine.
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