-
KIYOKO TAKAMURA, FUMIYO KUSU
1986 Volume 34 Issue 6 Pages
2315-2320
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
In order to elucidate the interaction of structurally nonspectific drugs with a charged surfaces, the adsorption of six barbiturates (barbital, phenobarbital, amobarbital, allobarbital, cyclobarbital and hexobarbital) on a gold electrode surface has been studied by specular reflectivity measurement in 0.1 M NaClO
4. These barbiturates are adsorbed in the potential range around the point of zero charge. From the potential and concentration dependences of their adsorption, it can be deduced that the surface behavior of all these barbiturates is essentially the same. Electrosorption of barbiturates may provide a very simple model of the combination of barbiturates with the synaptic membranes.
View full abstract
-
MASAHIDE NOJI, KEIGO CHISAKI, JUNZO HIROSE, TAIJI KATO, YOSHINORI KIDA ...
1986 Volume 34 Issue 6 Pages
2321-2329
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
An attempt was made to develop new water-soluble antitumor Pt(II) complexes by introducing hydroxyl groups into a carrier ligand, 1, 2-diamino-1, 2-dideoxy-D-glucitol (1, 2-DAG), and their structures were determined by
13C nuclear magnetic resonance and circular dicroism spectral analyses. Only [Pt(NO
3)
2(1, 2-DAG)] and [Pt(SO
4)(1, 2-DAG)] exhibited marginal effects against leukemia L1210 in vivo, among compounds with various leaving groups.The unexpectedly low antitumor activity of Pt(II) complexes containing 1, 2-DAG was investigated in in vitro experiments. The Pt(II) complexes of 1, 2-DAG showed the same binding mode with calf-thymus deoxyribonucleic acid (DNA) as cis-diamminedichloroplatinum(II), but inhibition of DNA synthesis in L1210 cells in vitro was not observed even at the concentration of 100 μM [PtCl
2(1, 2-DAG)] or [Pt(oxalato)(1, 2-DAG)]. Consideration of the Pt contents taken into the cells indicated that the Pt(II) complexes have difficulty in passing through the cell membranes, which might account for the low antitumor effects observed in vivo.
View full abstract
-
TOMOKO OTSUKA, TOSHIE OHYA, MITSUO SATO
1986 Volume 34 Issue 6 Pages
2330-2340
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Electron paramagnetic resonance (EPR) spectroscopy has been employed to characterize the hydrogen-(H-) bonded state of the mixed-ligand low-spin complex Fe(TPP) (OMe) (NMeIm), which is formed upon mixing of Fe(TPP) (OMe) with NMeIm in Me
2SO-MeOH. Two spectrally distinct low-spin species, designated A and B in increasing order of g anisotropy, were detected depending upon the MeOH concentration in the solvent. The two low-spin species differ in degree of H-bond formation between the coordinated MeO
- and the solvent MeOH. The H-bond formation proceeds in one step, by EPR criteria, A and B being regarded as in the initial and final H-bonded states, respectively. The H-bonding interaction results in a decreased crystal field around the iron, thereby causing the tetragonal and rhombic splittings in the t
2 orbitals to decrease on going from A to B.
View full abstract
-
TOSHIKO UTAMURA, KEIKO KUROMATSU, KIYOKO SUWA, KYOKO KOIZUMI, TETSURO ...
1986 Volume 34 Issue 6 Pages
2341-2353
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
All the isomers of the tetra-O-acetyl-D-glucopyranoses, and their monobenzyl and monotrityl derivatives were synthesized and systematic
1H- and
13C-nuclear maghetic resonance (
1H-and
13C-NMR) studies were carried ont. Complete assignments of the
1H- and
13C-NMR signals were achieved by
1H[
1H]- and
13C[
1H]-decoupling techniques and by the use of a shift reagent and changes of solvents. Moreover, when necessary,
1H[
1H]- and
13C[
1H]-shift-correlated 2D NMR spectroscopy at higher frequency (Bruker AM 400) was applied. The shifts on deacetylation, benzylation, and tritylation were estimated on the basis of the
1H- and
13C-chemical shifts of these compounds, and the effects of deacetylation and benzyl- or trityl-substitution are discussed.
View full abstract
-
TAKASHI HARAYAMA, KAYOKO KOTOJI, REIKO YANADA, FUMIO YONEDA, TOORU TAG ...
1986 Volume 34 Issue 6 Pages
2354-2361
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Oxidations of 1, 3-dimethylthymine (1), 3', 5'-diacetylthymidine (2), 1, 3-dimethyluracil (3), 5-fluoro-1, 3-dimethyluracil (4), and 2', 3', 5'-triacetyluridine (5) with m-chloroperbenzoic acid were investigated. Dimethylthymine (1) gave the hydroxy ester (6), the stereostructure of which was determined by an X-ray analysis, while diacetylthymidine (2) gave 10a and 10b. Dimethyluracil (3) provided 11, 12, and 13, and 5-fluoro-dimethyluracil (4) provided 11. Triacetyluridine (5) afforded 16 in dichloromethane and 17 in benzene. A plausible mechanism for formation of these oxidation products is presented.
View full abstract
-
TAKAO SAKAMOTO, YOSHINORI KONDO, HIROSHI YAMANAKA
1986 Volume 34 Issue 6 Pages
2362-2368
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Catalytic hydrogenation of o-nitrophenylacetaldehyde diethyl acetal over palladium-carbon, followed by intramolecular cyclization of the resulting o-aminophenylacetaldehyde diethyl acetal with hydrochloric acid, gave indole. Similarly, 4-methylindole, ethyl 5-indolecarboxylate, and various pyrrolopyridines were synthesized from the corresponding o-nitroacrylacetaldehyde derivatives. The preparation of the desired o-nitroarylacetaldehydes was accomplished by the condensation of o-halonitroaromatics with trimethylsilylacetylene in the presence of dichloro-bis(triphenylphosphine)palladium as a catalyst, followed by ethanolysis of the resulting o-(tri-methylsilylethynyl)nitroaromatics.
View full abstract
-
MASAO TSUKAYAMA, TOKUNARU HORIE, KUNIHIRO FUJIMOTO, MITSURU NAKAYAMA
1986 Volume 34 Issue 6 Pages
2369-2374
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The condensation of 6', 7-bis(benzoyloxy)-2', 4'-dimethoxyisolfavone (18) with 2-methyl-3-buten-2-ol, followed by hydrolysis of the resultant 6', 7-bis(benzoyloxy)-2', 4'-dimethoxy-3'-(3-methyl-2-butenyl)isoflavone (19) gave 6', 7-dihydroxy-2', 4'-dimethoxy-3'-(3-methyl-2-butenyl)-isoflavone (licoricone) (1). Its isomer, 6', 7-dihydroxy-2', 4'-dimethoxy-5'-(3-methyl-2-butenyl)-isoflavone (2), was also synthesized from 7-benzoyloxy-6'-hydroxy- or 6', 7-bis(benzoyloxy)-2', 4'-dimethoxy-5'-(3-methyl-2-butenyl)isoflavone (11 or 20).
View full abstract
-
KYOKO ISHIGURO, MASAE YAMAKI, SHUZO TAKAGI, YOSHIAKI IKEDA, KIYOTAKA K ...
1986 Volume 34 Issue 6 Pages
2375-2379
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
An extensive study has been made on the antitumor activity of several iridoid glycosides and their aglycones in mice bearing the experimental tumor leukemia P388. Most of the aglycones were found to be active. Among them, scadoside methyl ester aglycone (SMEH) showed the most potent activity, and it was furhter tested against several kinds of experimental tumor. None of the glucosides showed any activity. Our observations suggest that the hemiacetal structure of iridoid aglycones plays a significant role in the antitumor activity, as in the case of the antimicrobial activity reported previously.
View full abstract
-
TOSHIRO IBUKA, GIL NAMG CHU
1986 Volume 34 Issue 6 Pages
2380-2390
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A stereoselective synthesis of (±)-perhydorgephyrotoxin (3) starting from 1, 3-bis(trimethyl-siloxy)-1, 3-butadiene and ethyl trans-2-octenoate is described. A crucial step is reductive decarboxylation of the γ-carbamoyloxy-α, β-enoate (6) with lithium dibutylcuprate to yield the β, γ-enoate (40).
View full abstract
-
TOSHIYUKI ITOOKA, KATSUHIDE MATOBA, TAKAO YAMAZAKI, OSAMU MURAOKA, TAK ...
1986 Volume 34 Issue 6 Pages
2391-2396
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Both 2β-bromobicyclo[3.3.1]nonan-3-one (IIa) and its 2α- epimer (IIb) afforded methyl bicyclo[3.2.1]octane-6β-carboxylate (IIIa) stereoselectively in the Favorskii reaction using sodium methoxide in methanol. In the reaction using sodium methoxide in dimethoxyethane (DME) at room temperature, the stereoselectivity decreased and the product was contaminated with methyl bicyclo[3.2.1]octane-6α-carboxylate (IIIb). However, when the reaction in DME was carried out at 0°C, IIIa was the only product.The routes involved in these transformations were examined by using nuclear magnetic resonance spectroscopic techniques with the deuterated compounds.
View full abstract
-
NOBUTAKA FUJII, MITSUYA SAKURAI, KENICHI AKAJI, MOTOYOSHI NOMIZU, HARU ...
1986 Volume 34 Issue 6 Pages
2397-2410
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Eight peptide fragments were prepared by known amide-forming reactions as building blocks for the solution synthesis of the dotetracontapeptide corresponding to the entire amino acid sequence of human intestinal GIP (gastric inhibitory polypeptide or glucose-dependent insulinotropic polypeptide). Besides Lys(Z), Trp(Mts) and Gln-OBzl, two new amino acid derivatives, Asp(OChp) and Glu(OChp) [Mts=mesitylenesulfonyl, Chp=cycloheptyl], were employed to suppress various side reactions. These fragments were successively assembled by the azide procedure to minimize racemization and all protecting groups employed were removed from the protected GIP by using 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid.Synthetic GIP exhibited a significant glucose-dependent insulinotropic activity in dogs, but failed to produce any notable anti-gastric activity in rats.
View full abstract
-
HIDEYUKI SEYA, KOOHEI NOZAWA, SHUN-ICHI UDAGAWA, SHOICHI NAKAJIMA, KEN ...
1986 Volume 34 Issue 6 Pages
2411-2416
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
In the course of searching for metabolites related to emestrin (3) from Emericella striata (80-NE-22), dethiosecoemestrin (1) was isolated from the methylene chloride extract of the culture filtrate. The tremorgenic mycotoxin, paxilline (6), was also isolated from the mycelial extract. The structure of dethiosecoemestrin was established on the basis of the chemical and spectroscopic evidence as 1. It is postulated that dethiosecoemestrin was biogenetically derived from emestrin.Dethiosecoemestrin was easily degradated to violaceic acid (5). The antimicrobial activity of dethiosecoemestrin was examined.
View full abstract
-
TOSHIRO IBUKA, TAKESHI AOYAGI, YOSHINORI YAMAMOTO
1986 Volume 34 Issue 6 Pages
2417-2427
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Reaction of γ-acetoxy-α, β-enoates with lithium dialkylcuprate followed by alkyl halides results in the predominant or exclusive formation of α-alkyl-β, γ-enoates in high yields under mild conditions, and a synthetic application to (±)-α-vetispirene is presented. Treatment of diethyl fumarate and triethoxycarbonylethylene with Bu
2CuLi·AlCl
3 led to 1, 4-addition to give conjugate adducts in high yields. In sharp contrast, diethyl maleate and tetraethoxycarbonylethylene predominantly gave the respective reduction products. Evidence for a presumed dianionic intermediate, based on trapping with some electrophiles, is also presented.
View full abstract
-
MASAKI SATO, IZUMI FUJIMOTO, TOSHINORI SAKAI, TACHIO AIMOTO, RYOHEI KI ...
1986 Volume 34 Issue 6 Pages
2428-2434
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Two antioxidative components in commercial preparations of sodium copper chlorophyllin were isolated as their methyl esters. Through the identification of the methyl esters by comparison with authentic samples and the saponification of the methyl esters, disodium copper isochlorin-e
4 and trisodium copper chlorin-e
6 were demostrated to be included in sodium copper chlorophyllin as constituents. The antioxidative activities of both sodium copper chlorins on Fe
2+ and ascorbic acid-induced lipid peroxidation in rat liver homogenates were about 8-fold greater than that of sodium copper chlorophyllin. The two components were concluded to play a principal role in the antioxidative action of sodium copper chlorophyllin.
View full abstract
-
AKIKAZU KAKEHI, SUKETAKA ITO, TOSHIAKI YOTSUYA
1986 Volume 34 Issue 6 Pages
2435-2442
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Alkaline treatment of 2, 3-annelated 1-ethoxycarbonylmethylpyridinium bromides was investigated as a method for the preparation of 1, 8-annelated indolizine derivatives. The reaction of 1-ethoxycarbonylmethyl-2, 3-cyclopentenopyridinium bromide (1) with ethanolic sodium ethoxide did not afford any significant products, but similar treatment of 1-ethoxycarbonylmethyl-2, 3-cyclohexenopyridinium bromide (8) gave the expected 1, 8-annelated 2(3H)-indolizinone, 8, 9-dihydro-7H-pyrrolo[3, 2, 1-ij]quinolin-1(2H)-one (9), in 53% yield. The reactions of the salt 8 with a base in the presence of some vinylating and alkylating or acylating agents afforded the corresponding 1-alkoxy- or 1-acyloxy-2-vinylpyrroloquinoline derivatives (26-35), which were further transformed to tetracyclic indolizines fused with a furan or a puran ring. Some of these tricyclic and tetracyclic indolizines showed antiallergic activity.
View full abstract
-
SHIGERU KOBAYASHI, TOSHIHIRO TOKUMOTO, TOMOMI KOIKE(nee OHTA), KINJI I ...
1986 Volume 34 Issue 6 Pages
2443-2447
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The structure of acid A, an oxidation product of lycoramine (1), an Ameryllidaceae alkaloid, was established as 4 on the basis of spectral and chemical evidence. The racemic methyl ester (8) of acid A (4) was synthesized.
View full abstract
-
SUSUMU KATO, TOSHIO FUKAI, JUNKO IKUTA(nee MATSUMOTO), TARO NOMURA
1986 Volume 34 Issue 6 Pages
2448-2455
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A new isoprenylated 1, 3-diphenylpropane derivative, kazinol L, was isolated from the extract of the root bark of Broussonetia kazinoki SIEB. (Japanese name, "Himekozo, " Moraceae), and three new isoprenylated 1, 3-diphenylpropane derivatives, kazinols J, M, and N were isolated from the cortex. The structures of kazinols J, L, M, and N were shown t be 1, 2, 3, and 4, respectively, on the basis of spectral data.
View full abstract
-
SHIRO YOSHIDA, HIROSHI TAKAKU
1986 Volume 34 Issue 6 Pages
2456-2461
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Trimers of 2', 5'-oligoadenylic acids bearing 2'-terminal 8-bromo- or 8-hydroxyadenosine have been synthesized by the phosphotriester method. Some properties of these compounds were studied by circular dichroism (CD) spectroscopy. The 2', 5'-adenylate trimer, A2'p5'A2'p5'HOA (10a) was found to have a less stacked structure than the 2', 5'-adenylate trimers A2'p5'A2'p5'BrA (11) and A2'p5'A2'p5'A (10b).
View full abstract
-
SUZUMITSU KUNO, KENICHI AKAJI, OSAMU IKEMURA, MOTOYUKI MORIGA, MITSURU ...
1986 Volume 34 Issue 6 Pages
2462-2470
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Human gastrin-releasing polypeptide (hGRP), which consists of 27 amino acid residues with a C-terminal amide, was synthesized by a conventional solution method, by assembling six peptide fragments followed by deprotection with 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. Met(O) employed was reduced by treatment with phenylthiotrimethylsilane in the presence of trimethylsilyl trifluoromethanesulfonate before deprotection. The synthetic peptide was as active as synthetic porcine GRP, in terms of immunoreactive gastrin release in rats.
View full abstract
-
JUNKO IKUTA(nee OHTA), TOSHIO FUKAI, TARO NOMURA, SINICHI UEDA
1986 Volume 34 Issue 6 Pages
2471-2478
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
From callus tissues of Morus alba L., four new yellow pigments, kuwanons J (1), Q (2), R (3), and V (4), have been isolated. Chemical and spectroscopic evidence revealed that these compounds are stereochemically identical Diels-Alder type adducts of two 4-hydroxyprenylchalcone moieties bearing all the four possible patterns of hydroxylation at the 2 and/or 16'' positions.
View full abstract
-
TOHRU KIKUCHI, SHIGETOSHI KADOTA, KOJI TSUBONO
1986 Volume 34 Issue 6 Pages
2479-2486
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The proton and carbon-13 nuclear magnetic resonance (NMR) signals of cycloeucalenol (1a), cycloeucalenol acetate (1b), cyclonervilol (2a), cyclonervilol acetate (2b), and cyclohomonervilol acetate (3b), isolated from Nervilia purpurea, were assigned by means of two-dimensional NMR spectroscopy.
View full abstract
-
MASAHIDE NOJI, SHINGO HANAMURA, KENJIRO SUZUKI, TAZUKO TASHIRO, YOSHIN ...
1986 Volume 34 Issue 6 Pages
2487-2493
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Antitumor Pt(II) complexes containing ester derivatives of DL-2, 3-diaminopropionate and DL-2, 4-diaminobutyrate were synthesized and their structures were determined from their infrared and ultraviolet absorption spectral data. The antitumor activity of these Pt(II) complexes was tested in vivo against leukemia L1210 according to the NCI Pt Analog Protocol. [Pt(Malonato)(DL-2, 3-diaminopropionate ethyl ester)] exhibited the highest antitumor effect with a T/C% value of 364 at an administration dose of 100 mg.The partition coefficients between water and n-octanol were measured, but no clear correlation with antitumor effects was found.
View full abstract
-
TOMIO OHTA, NAOKI MIYATA, MASAAKI HIROBE
1986 Volume 34 Issue 6 Pages
2494-2500
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The metabolism of various 5H-N-substituted dibenz[b, f]azepines (1a-e) by rat liver microsomal fractions was investigated. 5H-N-Acyldibenz[b, f]azepines (1a-c) were metabolized to 5H-N-acyldibenz[b, f]azepine 10, 11-oxides (2a-c), while 5H-N-alkykibenz[b, f]azepines (1d, e) were metabolized to N-alkyl-9(10H)-acridones (5d, e). 5H-N-Acyl-10, 11-dihydro-trans-10, 11-dihydroxydibenz[b, f]azepine (3b) was additonally detected as a metabolite of 5H-N-acyldibens[b, f]azepine 10, 11-oxide (2b).The conditions for the enzymatic formation of these metabolites are discussed.
View full abstract
-
TSUYOSHI TANIMOTO, HIDEO FUKUDA, TSUTOMU YAMAHA, YOSHIROU OHMOMO, MASU ...
1986 Volume 34 Issue 6 Pages
2501-2505
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Twelve kinds of benzyl oxazolecarbamate analogues were tested in vitro for inhibition of aldose reductases, which play a leading role in the etiology of diabetic complications such as cataract, retinopathy and neuropathy. The comparative study of various analogues substituted with a benzylcarbamate group at C-2, C-4 of C-5 of the oxazole skeleton showed that the benzylcarbamate group at the C-2 position was absolutely necessary for potent aldose reductase inhibitory activity.The group at C-4 of C-5 was ineffective. Introduction of an alkyl group at the C-4 position of benzyl 5-phenyl-2-oxazolecarbamate increased the inhibitory activity, and in particular, the 4-isopropyl analogue was found to be a potent inhibitor. The 50% inhibition concentration of benzyl 4-isopropyl-5-phenyl-2-oxazolecarbamate (IV) for aldose reductases Ia and Ib was about 3.5×10
-7M, whereas that of benzyl 5-phenyl-2-oxazolecarbamate (I) was about 1.5×10
-5M. Inhibition of rabbit lens aldose reductase by compound IV was of a non-competitive type with DL-glyceraldehyde as a substrate. Compound IV appears to be a specific inhibitor of rabbit lens aldose reductase, because it was found to have little inhibitory effect against several other enzymes.
View full abstract
-
TAMOTSU SAITOH, SHIGEMI SAKASHITA, HIROYUKI NAKATA, TAKASHI SHIMOKAWA, ...
1986 Volume 34 Issue 6 Pages
2506-2511
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Six aromatic compounds 1-6 were isolated from Sappan Lignum, the dried heartwood of Caesalpinia sappan L., and were characterized as 3-benzylchroman derivatives by spectroscopic means. They seem to be closely related biosynthetically to brazilin; 2 and 3 may be precursors and 4-6 may be key intermediates in the biogenesis of brazilin.
View full abstract
-
NORIYUKI KIWASHIRI, KAZUO TORIIZUKA, ISAO ADACHI, MASAHARU UENO, KATSU ...
1986 Volume 34 Issue 6 Pages
2512-2517
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Fifteen crude drugs used in traditional Sino-Japanese medicine were investigated to analyze their effects on fibrinolysis by plasmin. Each crude drug was extracted with water (W), boiling water(H) and hot ethanol (E). The extracts were tested for inhibitory effect on fibrinolysis by the fibrin plate method and on plasmin activity by the chromogenic substrate method, and the following results were obtained.Rhei Rhizoma, Moutan Cortex and Paeoniae Radix : Each extract showed marked inhibitory effects on fibrinolysis and plasmin activity.Atractylodis Lanceae Rhizoma : H showed an inhibitory effect on fibrinolysis.Eupolyphaga, Tabanus, Armeniacae Semen, Persicae Semen and Cnidii Rhizoma : E inhibited plasmin activity, while W and H were ineffective.One of the antiplasmin principles in Eupolyphaga (Opisthoplatia orientalis BURMEISTER) was identified as oleic acid. Some cis-unsaturated fatty acids, such as linoleic acid and palmitoleic acid, also inhibited plasmin activity.
View full abstract
-
KEIICHI NISHIMURA, TOSHIO MIYASE, AKIRA UENO, TADATAKA NORO, MASANORI ...
1986 Volume 34 Issue 6 Pages
2518-2521
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Three new sesquiterpene glycosides, picrisides A (III), B (VI) and C (VII), in addition to lactucin (I), 11β, 13-dihydrolactucin (II), crepidiaside A (IV) and ixerin F (V), have been isolated from the methanol extract of Picris hieracioides L. var. japonica REGEL (Compositae). The stuctures of the new compounds were determined on the basis of chemical and spectral data.
View full abstract
-
TAKESHI ONO, KAZUYUKI TANIDA, HIDEHIKO SHIBATA, HIROKI KONISHI, HARUMI ...
1986 Volume 34 Issue 6 Pages
2522-2527
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A simple, rapid, sensitive and reproducible reversed-phase high-performance liquid chromatographic (HPLC) method was developed for the quantitative determination of urinary 6β-hydroxycortisol (6β-OHF) as a non-invasive indicator of drug-metabolizing enzyme activity in man. The urine (10ml) containing 6β-hydroxycortisone as an internal standard was loaded onto a Sep-Pak C
18 column and eluted with ethyl acetate. The samples were analyzed on a Radial-Pak Nova-Pak C
18 column, and the compounds were eluted with a mixture of 0.01 M potassium dihydrogen phosphate-acetonitrile-methanol (935 : 55 : 10) containing 0.005% trichloroacetic acid as a mobile phase and quantified by ultraviolet absorbance measurement at 243.5nm. The analytical recovery of added 6β-OHF was almost complete. The reproducibility assessed by repeated analysis was satisfactory, that is to say, the coefficient of variation ranged from 2.06 to 2.25% (within-run) and from 2.82 to 3.11% (between-run). In healthy adult subjects (23-41 years), the mean excretion rate of 6β-OHF was 214 μg/d (S.D.=41.4; n=10) and the mean ratio of 6β-OHF to 17-hydroxycorticosteroids was 0.0310 (S.D.=0.00662; n=10).The present HPLC method was found to be applicable to the routine assay of urinary 6β-OHF in clinical studies.
View full abstract
-
MASAYOSHI TABARA, MITSUO WATANABE
1986 Volume 34 Issue 6 Pages
2528-2531
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The effect of a potent tumor promoter, 12-tetradecanoylphorbol-13-acetate (TPA), on delayed type hypersensitivity (DTH) to sheep red blood cells (SRBC) in ddy mice was investigated. The mice were immunized with 10
8 SRBC, and footpad reaction (FPR) was measured after challenge with 10
8 SRBC. When 5μg of TPA was administered to the mice 24h before the challenge by painting on the skin. FPR was markedly suppressed. The suppression was greater in the painting of TPA on the footpads of the challanged leg than on the footpad of the other leg. These data suggest that the suppression of FPR involves not only a systemic process, but also a local effect.The application of 4 phorbol related compounds (TPA, phorbol 12, 13-didecanoate, 4α-phorbol 12, 13-didecanoate and phorbol) showed that the suppressive effect was on DTH virtually paralleled the tumor-promoting activity. Treatments with λ-carrageenan and formaldehyde did not suppress the FPR. These data suggest that the present effect may not be related to the phlogistic effect.
View full abstract
-
MOTOKO WATANABE, KAZURO IWAI, SHOJI SHIBATA, KUNIO TAKAHASHI, TAKAO NA ...
1986 Volume 34 Issue 6 Pages
2532-2541
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Administration of some anititumor lichen polysaccharides (ALP) increased the serum level of α
1-acid glycoproteins (α
1-AG) in mice, possibly as a result of liver cell necrosis or inflammation induced by those polysaccharides.Ascites tumor-bearing mice were treated with ALP, and ascitic fluid having a high α
1-AG level was harvested. Mouse α
1-AG was obtained from this source in quanity, and fractionated into α
1-AG-1 and -2.The time courses of the serum level of α
1-AG and of the growth of subcutaneously implanted tumor were found to correlate well in ALP-treated mice, and purified α
1-AG-1 inhibited the growth of tumor cells in vitro at a concentration normally observed in animals with inflammation. These results suggest that α
1-AG plays a significant role in the antitumor activity exhibited by ALP.
View full abstract
-
YOSHIHIKO INAMORI, MAYURI KUBO, YOSHIAKI KATO, HIROSHI TSUJIBO, MICHIH ...
1986 Volume 34 Issue 6 Pages
2542-2549
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Histopathological examination of tissues and analysis of uric acid in hemolymph and feces of the 5th instar larvae of the silkworm, Bombyx mori LINNE, either treated with racemomycin-D or deoxypodophyllotoxin both of which showed delayed insecticidal activities, or being starved, gave the following results. 1) In the larvae treated with racemomycin-D the epidermal cells and fat body cells were seriously damaged along with the Malpighian tubules, 2) in the larvae treated with deoxypodophyllotoxin, the fat body cells as well as the epidermal cells were seriously damaged, but the Malpighian tubules remained intact, 3) on starvation, only the fat body cells were damaged. 4)Both in the starved and the deoxypodophyllotoxin-treated larvae, a considerable increase of uric acid was noted in hemolymph and feces.It was concluded that the increase of uric acid in hemolymph and feces was caused by the histolysis of fat body cells due to inadequate feed intake, resulting either directly therough starvation or indirectly through the effects of the chemicals.
View full abstract
-
KAYO INOUE, TOSHIO MAZDA, TAKASHI TOBE, MOTOWO TOMITA
1986 Volume 34 Issue 6 Pages
2550-2554
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A monoclonal antibody (MAb) to von Willebrand factor antigen (vWF : Ag) was produced. In the present study, we used the MAb for an enzyme-linked immunosorbent assay (ELISA) to quantify vWF : Ag. The amount of vWF : Ag bound to a rabbit rabbit antibody coated on a plate was measured by applying sequentially MAb, a peroxidase-labeled antibody to murine immunoglobulin and enzyme substrate. The assay is quick and simple.Cryoprecipitates were prepared with three thawing (slow-thaw, rapid-thaw and modified thaw-siphon) methods. ELISA for vWF : Ag and an assay for factor VIII clotting activity (VIII : C) were performed on cryoprecipitates and on cryosupernatants. The recoveries of vWF : Ag and VIII : C in the cryoprecipitate by the modified thaw-siphon method were the highest among the three methods.The ratio of VIII : C to the content of vWF : Ag was high in the cryosupernatant and low in the cryoprecipitate.
View full abstract
-
NAOHITO OHNO, YOSHIYUKI ADACHI, IWAO SUZUKI, SHOZO OIKAWA, KICHIRO SAT ...
1986 Volume 34 Issue 6 Pages
2555-2560
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Several antitumor glucan fractions obtained by various extraction procedures from Grifola frondosa were compared by solution and solid (cross polarization, magic angle spinning (CP/MAS))carbon-13 nuclear magnetic resonance (
13C-NMR) spectroscopy. The fractions prepared under milder conditions, i.e., hot water extract (AHW), liquid culture filtrate (LLFD), and extracellular polysaccharide (LELFD), showed a C-3 signal at the same chemical shift as that in DMSO-d
6 solution (native form) in
13C CP/MAS NMR spectroscopy. However, the fractions prepared under drastic conditions, i.e., cold alkali extract (NMF-5, grifolan), showed a C-3 signal at 89 ppm, simiar to those of curdlan and attributable to helix structure (helix form). After dissolution of LELFD in 8M urea followed by dialysis, LELFD also showed a C-3 signal at 89ppm. These results suggest that the polysaccharides obtained from G. frondosa possess two kinds of conformations.
View full abstract
-
HIRAKU ONISHI, TSUNEJI NAGAI
1986 Volume 34 Issue 6 Pages
2561-2567
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Alkylenediamine-dextran T70(T70-C
n) might be useful as a polymer support for anti-tumor polymeric drugs, and its preparation was investigated. Decylenediamine-dixtran T70(T70-C
10) was selected as the most suitable compound. Methotrexate (MTX) or mycophenolic acid was conjugated through an amide bond involving the carboxyl group of the drug and the amino group of T70-C
10. Stability tests under the conjugation reaction conditions confirmed that T70-C
10 could be utilized as a polymer support. The conjugation reaction with 1-ethyl-3-(3-dimethylamino-prophyl)carbodiimide hydrochloride as the reagent was satisfactory. The inhibition of dihydrofolate reductase by the conjugate of T70-C
10 and MTX (T70-C
10-MTX) was checked in vitro.
View full abstract
-
MINORU KURODA
1986 Volume 34 Issue 6 Pages
2568-2577
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
An investigation was carried out on poultices molded on cloth to ascertain whether y
j can be related to x
i, where x
i is the value of the i'th physical property of a molded poultice, obtained by using instrumental techniques, and y
j is the preference value of a subject treated with the poultice for the j'th textural characteristic, obtained by sensory evalutaion. Four formulations of molded poultices were prepared and used. Sensory tests of these poultices were performed with 23 volunteers. The relations between y
j and x
i were obtained for six characteristics as linear regression equations with good correlation coefficients. It should be possible to apply these equations to screen the quality of a new molded poultice by means of objective and reproducible measurements using instrumental techniques instead of extensive field tests.
View full abstract
-
MINORU KURODA, HIDEO KANEKO, SADAO HIROTA, YOSHIO OHNO
1986 Volume 34 Issue 6 Pages
2578-2584
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
In the previous paper, the value (x
i) of the i'th physical property of a molded poultice was measured, the preference value (y
j) for the j'th textural characteristic was obtained in sensory tests, and a mathematical expression for the relation between y
j and x
i was obtained in the form of first-order regression equations with good regression coefficients. A study was performed to ascertain whether x
i is related to and can be obtained from the quantities, a
k, of components, k, in a preparation. Molded poultices of 53 formulations contaning various quantities of nine ingredients were prepared and their physical properties were measured. For seven of their properties, the relations between x
i and a
k were analyzed by stepwise multiple regression analysis and were obtained in the form of first-order regression equations with a confidence level above 95%. These relations made it possible to carry out simulation of the optimum formulations of molded poultices.One of the simulated optimum formulations showed viscoelasticity at 50°C obeying the four-element model, whose values were dete mined from creep test data.
View full abstract
-
NAOKO OHTA, TOSHIHISA YOTSUYANAGI, KEN IKEDA
1986 Volume 34 Issue 6 Pages
2585-2590
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The hydrolysis rate of meclofenoxate hydrochloride (MFX) was investigated in the absence and in the presence of human serum albumin (HSA). Compared with the degradation of the drug(pK
a 8.2) in buffer solutions, the degradation rate in HSA solutions (pH 4.0-10.7) was accelerated in the acidic region below pH 7.0 and was retarded in the basic region above pH 7.0.Based on a Michaelis-Menten type kinetic scheme involving the formation of HSA-drug complexes for both protonated and neutral forms of MFX, the effects of the protein on the degradation rate were analyzed and the hydrolysis rate constants and the binding constants of HSA-drug complexes were obtained.It was found that the neutral form was considerably stabilized by the association with HSA whereas the degradation of the protonated form was accelerated, and the neutral form-HSA complex was extremely stable compared with the protonated form-HSA complex. These results suggest that the neutral and protonated forms are bound to HSA molecules in different modes, the former being less accessible than the later to hydroxide ion attack.
View full abstract
-
NAOMI I. NAKANO, KAORU IWASAKA, SHOKO FUNADA, YOSHITERU HONDA, MASAHIR ...
1986 Volume 34 Issue 6 Pages
2591-2598
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Agarose beads containing a powdered charcoal or a cation-exchange resin were prepared by dropping a hot aqueous suspension of adsorbents in agarose sol into an organic solvent mixture consisting of cyclohexane and chloroform (2 : 1). The beads were crosslinked for intended use in direct hemoperfusion circuits as adsorbent columns. Their in vitro adsorption characteristics for selected adsorbates such as theophylline, paraquat, cholate, etc., from rabbit blood as wel as from Ringer's solution were evaluated by means of batchwise adsorption experiments and by the column method. Adsorption rate rather than capacity was reduced by incorporation of the powdered adsorbent into agarose gel, particularly for larger adsorbates. On the basis of equal adsorbent weight, the cation-exchange resin beads adsorbed paraquat from Ringer's solution better than did coated petroleum-based activated carbon beads obtained from a commercial hemoperfusion column. No significant changes in the levels of plasma components were observed after contact with the blood. The degree of platelet reduction was similar for the charcoal beads and control agarose beads without an adsorbent, though that for the resin beads was slightly greater. These adsorbent-containing agarose beads are likely to be of value for blood purification.
View full abstract
-
ATSUSHI WATANABE
1986 Volume 34 Issue 6 Pages
2599-2605
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A practical application of polarizing microscopy has been investigated by using key refractive indices (n
1, n
2) of group A drugs (lamellar, scales or plates). A graphic illustration of the retardation plotted log(n
2-n
1) as the abscissa and log(D) as the ordinate, where D denotes the thickness of the sample, gives a simple striped pattern composed of parallel straight lines having various retardations. As group A drugs have unique values of log(n
2-n
1), the thickness of a crystalline particle can easily be obtained from the graph by observing the interference color of the crystal under crossed polars.When the thickness of the crystal is obtained, the specific surface area can be calculated by the general microscopic method. This procedure could be useful for quality testing of poorly soluble drugs.
View full abstract
-
SABURO SHIMABAYASHI, MASAHIRO KOJIMA, OSAMU KUSADA, MASAYUKI NAKAGAKI
1986 Volume 34 Issue 6 Pages
2606-2608
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The formation of by-products during the preparation of hydrated calcium diphosphates(Ca
2P
2O
7·nH
2O, n=2 or 4) was examined in samples which were obtained through the literature methods. When CaH
2P
2O
7 was used as the reactant (2CaH
2P
2O
7+nH
2O→Ca
2P
2P
7·nH
2O+H
4P
2O
7), the product contained not only hydrated calcium diphosphate but also calcium ammonium diphosphate and/or acidic calcium diphosphate, depending on the reaction medium(0.05M NH
4OH, 2.2M Ca(CH
3COO)
2, or water). When K
4P
2O
7 and CaCl
2 were reacted in an aqueous solution of KCl, a significant amount of diphosphate ion (ca. 57%) was hydrolyzed to orthophosphate ion. The product was amorphous when the molar ratio of the reactant Ca
2+ to diphosphate ion was higher than 1.0. Several kinds of crystalline calcium potassium diphosphate were found in the product when the ratio was lower than 1.0. Therefor, it was concluded that hydrated calcium diphosphates prepared in the aqueous phase by the literature methods are generally contaminated with several kinds of by-product.
View full abstract
-
MASAKO MURAOKA, JUNKO IWAHARA, MICHIKO KANEKO
1986 Volume 34 Issue 6 Pages
2609-2613
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
2, 6-Diacetamido-8-hydroxy-9-(3, 5-O-diacetyl-2-O-tosyl-β-D-ribofuranosyl)purine (III) was cyclized with ammonia in methanol to give a mixture of 2, 6-diamino-8, 2'-anhydro-8-hydroxy-9-β-D-arabinofuranosylpurine (V) and 2-acetamido-6-amino-8, 2'-anhydro-8-hydroxy-9-β-D-arabinofuranosylpurine (IV), which was deacetylated to the cyclonucleoside (V) with 40% methylamine.After acetylation, the cyclonucleoside (V) was converted to 2, 6-diamino-9-β-D-arabinofuranosylpurine (IX) by cleavage of the anhydro linkage with H
2S in pyridine followed by Raney Ni dethiolation. Alternatively, acetylated arabinofuranosylguanine (X) derived from 8, 2'-anhydro-8-hydroxy-9-β-D-arabinofuranosylguanine was chlorinated with phosphoryl chloride and aminated with ammonia in metthanol to afford the arabinoside (IX).
View full abstract
-
MINEO SHIMIZU, HIDEKI FUKUMURA, HIDEKI TSUJI, SEIICHI TANAAMI, TOSHIMI ...
1986 Volume 34 Issue 6 Pages
2614-2617
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The ether-soluble fraction of EtOH extract from the leaves of Eriobotrya japonica LINDL.showed an anti-inflammatory effect when topically applied to rats. Ursolic acid, maslinic acid, methyl maslimate and euscaphic acid were isolated from the ether-soluble fraction. Maslinic acid was found to show an anti-inflammatory effect on carrageenan-induced edema and an inhibitory effect on histamine-induced ileum contraction.
View full abstract
-
MASAKAZU KAWATA, MASAHIRO NAKAMURA, SHIGERU GOTO, TOSHINOMU AOYAMA
1986 Volume 34 Issue 6 Pages
2618-2623
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Microencapsulation of ketoprofen using Eudragit RS, which is a copolymer synthesized from acrylic and methacrylic acid esters with a low content of quaternary ammonium groups, was investigated. The preparation is based on dispersion of acetone containing the drug in liquid paraffin. Aluminium tristearate was used as an additive for the preparation of microcapsules. Good reproducibility in microcapsule preparation was observed. The microcapsules obtained were uniform and free-flowing particles. The dissolution rates of ketoprofen from these microcapsules were considerably decreased as compared with that from ketoprofen powder.
View full abstract
-
JUNZO NAKAMURA, YOSHIO INOUE, HITOSHI SASAKI, JUICHIRO SHIBASAKI
1986 Volume 34 Issue 6 Pages
2624-2627
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Salicylic acid was detected in the blood at 2h after oral administration of salicyluric acid(60 mg/kg : salicylic acid equivalent) to rabbits and reached the maximum level at 5h (about 9.7 μg/ml). The levels of salicylic acid remained above 7μg/ml for several hours, after which they slowly declined. Following the simultaneous oral administration of salicylic acid (7.5 mg/kg) and salicyluric acid (60 mg/kg : salicylic acid equivalent), the blood concentration of salicylic acid was maintained at 8.5-15.3μg/ml from 6 min to 12h. Different blood level patterns of salicylic acid could be produced by simultaneous oral administration of salicyluric acid and various doses of salicylic acid.
View full abstract
-
KUNIO NAKANISHI, MIKIO MASADA, TANEKAZU NADAI
1986 Volume 34 Issue 6 Pages
2628-2631
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The effect of three nonsteroidal anti-inflammatory drugs (NSAID), indomethacin, phenylbutazone and dicolofenac sodium, on the absortion of water-soluble drugs with various molecular weights through the rectal membrane was evaluated by using an in situ perfusion technique.
14C-Inulin,
125I-insulin,
125I-polyvinyl pyrrolidone (PVP) and
125I-albumin were selected as marker drugs. NSAID increased the absorptions of inulin, insulin and PVP, but not that of albumin. It is suggested that macromolecular drugs with a molecular weight of less than 35000 are able to penetrate through the rectal membrane in the presence of NSAID.
View full abstract
-
SHOZO MIYAZAKI, NORIO HASHIGUCHI, WEI-MIN HOU, CHIZUKO YOKOUCHI, MASAH ...
1986 Volume 34 Issue 6 Pages
2632-2636
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The antitumor activity of fibrinogen microparticles containing adriamycin against Ehrlich ascites carcinoma in mice was evaluated on the basis of animal survival data. Tumor cell injections were performed on day 0 and microparticle injections on day 1, both intraperitoneally. A prolongation of the life span of tumor-bearing mice following injection of therapeutic microparticles was noted, and the microparticles containing adriamycin were therapeutically more effective than adriamycin alone. The high chemotherapeutic efficiency of fibrinogen-adriamycin microparticles was striking at high doses which would be toxic in the case of the drug alone. These results indicated that fibrinogen microparticles containing adriamycin may be effective in cancer chemotherapy. Microparticles composed of fibrinogen could be a novel drug carrier for use in injectable delivery systems for anticancer agents.
View full abstract
-
YOSHIHARU MACHIDA, TADAKAZU TOKUMURA, SHIGEMI KOMURO, YUKI TSUSHIMA, K ...
1986 Volume 34 Issue 6 Pages
2637-2641
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A new method of dissolution testing for oily drug preparations, the drug and vehicles of which tend to float on the surface of the dissolution test medium, was investigated. In this study, a modified version of the paddle method of JPX, involving an additional (assistant) wing to stir the surface of the medium, was use. Moreover, polypropylene beads were added to the medium in order to enhance the efficiency of stirring. The 2nd fluid containing 20mM sodium glycochenodeoxycholate was used as a dissolution test medium. A linear relationship was observed between the percent of the drug dissolved and the lapse of time, and also between the dissolution rate and the number of beads used. It was found that there was an optimum rotation speed of the paddle.
View full abstract
-
Hiroyuki Setoi, Hidekazu Takeno, Masashi Hashimoto
1986 Volume 34 Issue 6 Pages
2642-2645
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Here the synthesis of 1-deoxynojirimycin(1___-) and 1-deoxymannojirimycin (2___-) from D-mannose is reported and their immunostimulating activity is evaluated.
View full abstract
-
Nobuya Katagiri, Toru Haneda, Hiroshi Watanabe, Chikara Kaneko
1986 Volume 34 Issue 6 Pages
2646-2648
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Irradiation of 4-(2-tetrahydropyranyloxy)-2-cyclopentenyl 3-acetoxyacrylate (2___∼) resulted only in an E___--Z___- isomerization. Also, the corresponding 4-oxo-2-cyclopentenyl derivative (7___∼) did not give the cyclized product on irradiation. These facts clearly indicate that the Libit's method is only an idea without any experimental verification.
View full abstract
-
Kazuhide Uchida, Tetsuichi Shibata, Masako Tomoda, Shin-ichi Saito, Se ...
1986 Volume 34 Issue 6 Pages
2649-2652
Published: June 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A more rapid and convenient microdetermination of hydroxyproline(Hyp) was established by modification of the conventional KISO method using flow injection analysis. This new flow method is based on the color change reaction between pyrole, the oxidation and decarboxylation product of Hyp, and Ehrlich's reagent. A good linear relationship was obtained between the concentration of Hyp (from 0 to 80 μg/ml) and absorbance.
View full abstract