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Kanki KOMIYAMA, Kazuhiko IIZUKA, Masakazu YAMAOKA, Hiroshi WATANABE, N ...
1989 Volume 37 Issue 5 Pages
1369-1371
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Tocotrienols were evaluated for activity against transplantable murine tumors inoculated i.p. into mouse, and the activities of two tocotrienols and α-tocopherols were compared. When the compounds were injected i.p., α- and γ-tocotrienols were effective against sarcoma 180, Ehrlich carcinoma, and IMC carcinoma, and γ-tocotrienol showed a slight life-prolonging effect in mice with Meth A fibrosarcoma, but the tocotrienols had no antitumor activity against P388 leukemia at doses of 5-40 mg/kg/d. On the other hand α-tocopherol had only a slight effect against sarcoma 180 and IMC carcinoma. The antitumor activity of γ-tocotrienol was higher than that of α-tocotrienol. Tocotrienols showed growth inhibition of human and mouse tumor cells when the cells were exposed to these agents for 72h in vitro, whereas tocopherol did not show any marked cytotoxic activity. Alpha- and γ-tocotrienols had inhibitory effects on lipid peroxidation of murine microsomes by adriamycin.
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Shigeki FUKASAWA, Ken TAKAGI, Munetsugu KURATA
1989 Volume 37 Issue 5 Pages
1372-1374
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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A proteinase was purified from the culture supernatant of a marine luminous bacterium, Vibrio splendidus ATCC 33125. The purified enzyme had a molecular weight of 60000. The enzyme was most active at pH 9.0 and 57°C, and was stable below 45°C. The enzyme activity was inhibited by phosphoramidon, ethylenediaminetetraacetic acid and orthophenanthroline. Metal ions such as Cu
2+, Hg
2+ and Ni
2+ also inhibited the activity. These results indicate that this enzyme is a metal-chelator-sensitive, alkaline proteinase.
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Mutuso OKUMURA, Kenji SUGIBAYASI, Yasunori MORIMOTO
1989 Volume 37 Issue 5 Pages
1375-1378
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Since the percutaneous absorption rates of water-soluble drugs are low in general, an enhancing system is needed when using the skin as an administration site for the drugs. We have investigated the effect of various penetration enhancers on the in vitro and invivo percutaneous absorptions of catecholamine analogs, i.e. levodopa (LD), dopamine hydrochloride (DPH) and isoproterenol hydrochloride (IPH), as model water-soluble drugs. It was found that medium-chain glycerides (Sefsol 318) markedly enhanced the in vitro permeation of the drugs through excised hairless rat skin among the enhancers tested in the present experiments; the permeation rates with 5% Sefsol 318 in water were about 65, 34 and 53 times higher than the corresponding control (without enhancer) for LD, DPH and IPH, respectively. In addition, the in vivo percutaneous absorption experiments showed that the blood levels of these drugs after application of aqueous gels containing 5% Sefsol 318 on rat skin were higher than those in the absence of enhancer. Drug levels in the liver and kidney were also higher than without Sefsol 318. Percutaneous administration of DPH with Sefsol 318 to hairless rats resulted in lower diastolic blood pressure and a slightly higher heart rate with as compared to administration without the enhancer.These results suggest that Sefsol 318 is a potential candidate to enhance the transdermal absorptio of water-soluble drugs.
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Hiroshi SUEMUNE, Michiyo HIZUKA, Tomoko KAMASHITA, Kiyoshi SAKAI
1989 Volume 37 Issue 5 Pages
1379-1381
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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γ-Hydroxyethyl α, β-unsaturated γ-lactone (2) is a promising intermediate for the synthesis of eldanolide and cis, cis-1, 2, 3-trisubstituted cyclopentane, which could be converted to 11-deoxyprostaglandins. In order to prepare optically active 2, enzymatic hydrolysis of (±)-trans-cyclohexene-4, 5-diacetate with Pseudomonas fluorescens lipase was examined, and the monoalcohol ((-)-6, >99%ee)with R-configuration was obtained in accored with prediction based on the three-site model proposed by us. Compound (-)-6 could be converted to the chiral lactone ((-)-2) via a sequence of reactions involving ring cleavage.
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Tadahiro SAWAYAMA, Masatoshi TSUKAMOTO, Takashi SASAGAWA, Shunsuke NAR ...
1989 Volume 37 Issue 5 Pages
1382-1383
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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(S)-3-Acetylthio-2-methylpropionic acid was obtained in a good yield by an effective optical resolution with a newly synthesized chiral amine, (S)-N-isopropyl(phenylalaninol), which was readily derived from (S)-phenylalaninol, as a resolving agent.
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Akinori KUBO, Yoshiyasu KITAHARA, Shinsuke NAKAHARA
1989 Volume 37 Issue 5 Pages
1384-1386
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Three isoquinolinequinone metabolites of a marine sponge, Xestospongia sp., and the nudibranch Jorunna funebris, i.e. renierol propionate (3), N-formyl-1, 2-dihydrorenierol acetate (7) and N-formyl-1, 2-dihydrorenierol propionate (8), were synthesized.
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Koohei NOZAWA, Yoshikazu HORIE, Shun-ichi UDAGAWA, Ken-ichi KAWAI, Mik ...
1989 Volume 37 Issue 5 Pages
1387-1389
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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The distribution of a tremorgenic mycotoxin, paxilline (1), was investigated in 19 species belonging to the genus Emericella. It was found that Emericella desertorum, E. foveolata, and E. striata produced paxilline (1). A new type of indoloditerpene, emindole DA (4), was also found in E. quadrilineata. A new tremorgenic indoloditerpene, 1'-O-acetylpaxilline (3), was isolated from the mycelium of E. striata. Its structure was established on the basis of spectroscopic investigations.
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Hiromichi MATSUURA, Tsuyoshi USHIROGUCHI, Yoichi ITAKURA, Toru FUWA
1989 Volume 37 Issue 5 Pages
1390-1391
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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From bulbs of Allium chinense G. DON (Liliaceae), a new furostanol glycoside, named chinenoside I (1), was isolated and the structure was established to be 26-O-β-glucopyranosyl 3β, 22, 26-trihydroxy-25(R)-5α-furostan-6-one 3-O-β-xylopyranosyl(1→4)[α-arabinopyranosyl(1→6)]β-glucopyranoside.
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Tamotsu NIKAIDO, Taichi OHMOTO, Takeshi KINOSHITA, Ushio SANKAWA, Fran ...
1989 Volume 37 Issue 5 Pages
1392-1395
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Sixty-one flavanones, twenty-six isoflavones and eight other flavonoids, obtained from Sophora tomentosa, S. flavescens, Scutellaria baicalensis and other medicinal plants or synthesized, were tested for their inhibitory activity against adenosine 3', 5'-cyclic monophosphate (cAMP) phosphodiesterase from beef heart. The structure-activity relationships were investigated.
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Kazuo ISHII, Haruo OKAJIMA, Youji OKADA, Hiroshi WATANABE
1989 Volume 37 Issue 5 Pages
1396-1398
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Several phosphatidylcholines (PCs) containing furan fatty acid (10, 13-epoxy-11, 12-dimethyloctadeca-10, 12-dienoic acid, F acid) were synthesized, and their antioxidant activities were studied in the oxidation of soybean PC. The rate of oxidation in soybean PC liposomes initiated with 2, 2'-azobis(2, 4-dimethylvaleronitrile) (AMVN), a lipophilic azoinitiator, was measured by following the oxygen uptake, the accumulation of conjugated diene, and the disappearance of unsaturated fatty acid moieties. These PCs containing F acid were found to retard the rate of oxidation in soybean PC liposomes, and the retarding effect increased in the following order : 1/2 mol of di-furanoacyl PC (di-F PC)<1 mol of 1-furanoacyl-2-linoleoyl PC (F-18 : 2 PC)<1 mol of 1-furanoacyl-2-arachidonyl PC (F-20 : 4 PC)<1 mol of di-F PC (1 : 1 : 1 : 2, as molar ratios of F acid residue). This is the first report showing that the naturally occurring F acid has a retarding effect on lipid peroxidation.
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Yutaka NISHIOKA, Syojiro KYOTANI, Masashi OKAMURA, Yasumi MORI, Masako ...
1989 Volume 37 Issue 5 Pages
1399-1400
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Albumin microspheres and microcapsules containing cisplatin (CDDP) were prepared and tested as chemotherapeutic agents for the treatment of hepatocellular carcinoma. CDDP albumin microspheres were prepared by hardening with glutaric aldehyde in accordance with the method to prepare W/O emulsion. On the other hand, microcapsules were prepared by formation of a coacervate by the phase isolation method. CDDP albumin microspheres and microcapsules thus prepared were sieved and sterilized by dry heat at 135°C for 4 h prior to use. The content and release of CDDP were determined. The CDDP contents for albumin microspheres and microcapsules were found to be 9.2% and 33.3%, respectively. Release of CDDP in vitro was found to be significantly different between the two formulations. CDDP release in vivo also investigated by injecting albumin microspheres and microcapsules into the hepatic artery of adult dogs. The blood CDDP concentrations after injection of both formulations were lower than those noted after injection of CDDP injectable solution, indicating that CDDP might be accumulated in the liver at a higher concentration and that use of the two formulations might result in alleviation of CDDP side effects.
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Masaki OTAGIRI, Hideki NAKAMURA, Yorishige IMAMURA, Ushio MATSUMOTO, J ...
1989 Volume 37 Issue 5 Pages
1401-1403
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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The binding of sulfadimethoxine and sulfaphenazole to human serum albumin (HSA) has been shown by circular dichroism measurements to be dependent on the N-B transition. The secondary drug binding sites were found to be optically active in the B conformation form in HSA but optically inactive in the N form. Moreover, the drug-HSA interaction in Tris-HCl buffer seems to be more sensitive to the conformational change in HSA, compared with that in the phosphate buffer.
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Mutsuo OKUMURA, Kenji SUGIBAYASHI, Keizaburo OGAWA, Yasunori MORIMOTO
1989 Volume 37 Issue 5 Pages
1404-1406
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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The permeabilities of several water-soluble drugs through excised hairless rat skin from their aqueous suspensions were investigated by using newly designed two-chamber diffusion cells. Disodium cromoglycate, diclofenac sodium, dopamine hydrochloride, isoproterenol hydrochloride, diltiazem hydrochloride and papaverine hydrochloride were selected as water-soluble drugs. Indomethacin, a lipophilic drug, and deuterium oxide (D
2O) were used for comparison. The skin permeability coefficients of these water-soluble drugs were 100-10000 times lower than that of indomethacin. Since these drugs have high solubility in the donor solution (distilled water or lactate buffer), however, the skin permeation rates, which are in general proportional to the product of skin permeability coefficient and solubility of drugs in the drug-donor compartment, were comparable to or higher than that of indomethacin (1.7 μg/cm
2/h) : the skin permeation rate of dopamine hydrochloride (458 μg/cm
2/h) was about 300 times higher than that of indomethacin. The water-soluble drugs with lower molecular weight and higher solubility in water showed higher skin permeation rates. These results suggest that some water-soluble drugs with low molecular weight and high solubility in water might be good candidates for transdermal drug delivery.
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Toshihiko OZAWA, Akira HANAKI
1989 Volume 37 Issue 5 Pages
1407-1409
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Hydroxyl radicals from the reaction of vanadyl ions (VO
2+) with hydrogen peroxide (H
2O
2) in an acidic solution can be detected by an electron spin resonance (ESR) spectroscopy using water-soluble spin-traps, α-(4-pyridyl-1-oxide)-N__-tert-butylnitrone (POBN) and 5, 5-dimethyl-1-pyrroline N__--oxide (DMPO). Further, the fact that some hydroxyl radical scavengers suppressed or reduced the production of POBN-OH adducts affirms the formation of hydroxyl radicals at the initial step of the reaction between VO
2+ and H
2O
2.
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Yoshio NAGATSU, Tsunehiko HIGUCHI, Masaaki HIROBE
1989 Volume 37 Issue 5 Pages
1410-1412
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Biomimetic oxidation of bioactive pyrazolo[1, 5-a]pyridine derivatives carried out with the chemical model for cytochrome P-450, afforded 6, 7-epoxides in relatively high yields, these appear to be chemically unstable precursors of the main metabolites, i__-.e__-., 6, 7-dihydro-6, 7-diols.
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Mikio HONJO, Tokumi MARUYAMA, Yoshiko SATO, Takahiko HORII
1989 Volume 37 Issue 5 Pages
1413-1415
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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2, 3-Bis(benzoyloxymethyl)cyclobutanone (3__∼) was prepared in three steps from diethyl 3, 3-diethoxy-1, 2-cyclobutanedicarboxylate (1__∼). Hydrogenation of the oxime (4__∼) of 3__∼ provided the two amino compounds ((5a)___∼ and (5b)___∼), from which 9-[2, 3-bis(hydroxymethyl)cyclobuthyl]adenines ((9a)___∼ and (9b)___∼) were synthesized in four steps. The steric configurations of 3__∼, (5a)___∼, (5b)___∼, (9a)___∼ and (9b)___∼ were established by
1H-NMR spectroscopies including the NOE difference experiments.
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Isao KITAGAWA, Kazuyoshi OHASHI, Wakuko KOYAMA, Hiroyuki KAWANISHI, To ...
1989 Volume 37 Issue 5 Pages
1416-1418
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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A simple apparatus for measuring the ion-transport activity of a substance has been developed. The apparatus designated W-07 comprises three parts : two glass-cells of aqueous phase sandwiching one teflon cell of organic phase with two artificial membranes in between. Using the apparatus W-07, we have demonstrated the ion-transport activities (for Na
+, K
+, and Ca
++ ions) of an oligopeptide-lactone, and resin-glycosides containing a macrocyclic lactone structure.
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Shigetoshi KADOTA, Lamek MARPAUNG, Tohru KIKUCHI, Hisao EKIMOTO
1989 Volume 37 Issue 5 Pages
1419-1421
Published: May 25, 1989
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Two new tetranortriterpenoids, mahonin and secomahoganin, have been isolated from the cotyledons of Swietenia mahogani and their structures have been determined by means of 2-D NMR spectroscopy.
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Takanobu MATSUNO, Tomoko MATSUKAWA, Yoshiharu SAKUMA, Takehisa KUNIEDA
1989 Volume 37 Issue 5 Pages
1422-1423
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Treatment of acetaminophen with an excess sodium nitrite under mildly acidic to neutral conditions results in smooth formation of new 3-nitro-4-acetamidophenol via N-acetyl-p-benzoquinone imine as an oxidation intermediate, which is a well-known, widely explored metabolite.
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Takaaki HAYASHI, Akio KANETOSHI, Mitsuhiko IKURA, Haruhisa SHIRAHAMA
1989 Volume 37 Issue 5 Pages
1424-1425
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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A lipid peroxidation inhibitor, bolegrevilol was isolated from the edible mushroom Suillus grevillei. The structure was determined as 1-acetoxy-6-geranylgeranyl-2, 4-dihydroxybenzene.
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Kazuhiko ICHINO, Hitoshi TANAKA, Kazuo ITO
1989 Volume 37 Issue 5 Pages
1426-1427
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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From the fresh leaves of Lindera umbellata Thunb. var. lancea Momiyama a new flavanone, named neolinderatone (6), was isolated and the structure was established by spectroscopic and chemical means as (2S__-, 3"S__-, 4"R__-, 3"'S__-, 4"'R__-)-5, 7-dihydroxy-6, 8-bis(4-isopropyl-1-methylcyclohexl-en-3-yl)flavanone.
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Tenji KONISHI, Shiu KIYOSAWA, Yasuo SHIMADA, Kazumoto MIYAHARA, Toshio ...
1989 Volume 37 Issue 5 Pages
1428-1430
Published: May 25, 1989
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New tetraphydroxy-2-(2-phenylethyl)chromone, tentatively named AH
16 was isolated from agalwood, "Jinko", and the structure was characterized as (5R__-, 6R__-, 7S__-, 8R__-)-2-(2-phenylethyl)-5e', 6a, 7e, 8e'-tetraphydroxy-5, 6, 7, 8-tetraphydrochromone, assuming the cyclohexenyl ring to have a boat conformation.
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Haruko TAKECHI, Minoru MACHIDA, Yuichi KANAOKA
1989 Volume 37 Issue 5 Pages
1431-1433
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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Upon irradiation of thiobarbiturates (1a-c) in the presence of olefins (4a-d), [2+2]cycloaddition occurred to give thietanes (5, 7, and 8) and its related compounds (6 and 9).
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Yutaka OZAKI, Ikumi OSHIO, Sang-Won KIM
1989 Volume 37 Issue 5 Pages
1434-1436
Published: May 25, 1989
Released on J-STAGE: March 31, 2008
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1, 2-Benzenediols and their monoethers were efficiently prepared from α, α-bis(ethylthio)cyclohexenones which were constructed by the C3+C3 annulation of 1, 1-bis(ethylthio)propan-2-one and the Mannich bases.
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