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Volume 108, Issue 12
Displaying 1-14 of 14 articles from this issue
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TAKAYUKI SHIOIRI, YASUMASA HAMADA1988 Volume 108 Issue 12 Pages 1115-1128
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSDiphenyl phosphorazidate (DPPA), diethyl phosphorocyanidate (DEPC), and trimethylsilyldiazomethane (TMSCHN2) have been introduced as versatile reagents for organic synthesis. Total syntheses of several biologically active natural products containing various different carbon skeletons have been achieved by use of DPPA, DEPC, and reactions developed by our group. Cytotoxic and/or antineoplastic cyclic peptides 1-7 of marine origin have been prepared using DPPA and DEPC as peptide coupling reagents and their cytotoxic activities against L 1210 murine leukemia cells have been explored. Preferred conformation of ascidiacyclamide (4), a representative of cytotoxic cyclic peptides, has been determined by X-ray crystallography and it has been proven that ascidiacyclamide (4) has no ionophoric activity toward alkali metal ions. Synthesis of dolastatin 3 bearing the revised structure 2 has been described. Cytotoxic depsipeptides from a tunicate, didemnins A (11c), B (12c), and their relatives (11b and 12b), have been efficiently prepared by condensation of the key eastern (13) and western (14b and 14a) fragments. The absolute configuration of avellanin B (26b), a fungal cyclic peptide exhibiting a pressor effect, has been determined by its synthesis. Its analog, avellanin A (26a), has been also efficiently prepared. Synthesis of AI-77-B (27), which was isolated from Baccilus pumilus AI-77 and has an interesting antiulcer activity, has been stereoselectively achieved starting from the 6-methylsalicylic acid ester (30), the L-leucinal derivative (31), and D-pyroglutamic acid (36).View full abstractDownload PDF (1250K) -
KAZUO UMEZAWA, TOMIO TAKEUCHI1988 Volume 108 Issue 12 Pages 1129-1140
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSNew anticancer agents and oncogene function inhibitors isolated from microorganisms in Institute of Microbial Chemistry are reviewed.
Aclacinomycin found in 1975 is a less toxic and non-mutagenic anthracycline. It is now in clinical use mainly for acute nonlymphocytic leukaemia. Tetrahydropyranyl-adriamycin was synthesized in 1979 as a structural analogue of baumycin, and proved to be effective in inhibiting leukaemias and various solid tumours in patients. FAD-104 is a new semisynthetic anthracycline consisting of the 14-hemipimelate derivative of adriamycinone and 2, 6-dideoxy-2-fluoro-a-L-talopyranose. It shows apparently stronger antitumour activity than adriamycin against L 1210 mouse leukaemia. It is effective over a very broad range. Liblomycin is a derivative of bleomycin, which is clinically used mainly for squamous cell carcinoma but has pulmonary toxicity. Liblomycin shows much less pulmonary toxicity than bleomycin and potent antitumour activity in animals. Spergualin and 15-deoxyspergualin are new anticancer agents with unique structures. They showed potent antitumour activity against many experimental leukaemias and some solid tumours. Their mechanism of antitumour action may include induction of tumour cell immunity.
More than 40 oncogenes have been identified. Many of them are considered to act through tyrosine kinase activity. Erbstatin was isolated as an inhibitor of tyrosine kinase associated with epidermal growth factor receptor. It also inhibits tyrosine kinase of src oncogene product. Herbimycin inhibits src oncogene functions. It changes the morphology of src-transformed cells into the normal morphology. Oxanosine inhibits ras oncogene functions. It changes the phenotypes of K-rasts-NRK cells completely into the normal phenotypes by decreasing the intracellular levels of guanine nucleotides. Various oncogenes induces activation of cellular phosphatidylinositol turnover. We have isolated psi-tectorigenin, an isoflavonoid, as an inhibitor of phosphatidylinositol turnover.View full abstractDownload PDF (1230K) -
MATSUE EBITANI1988 Volume 108 Issue 12 Pages 1141-1147
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSRiboflavin tetraesters such as riboflavin tetraacetate, tetrapropionate, tetrabutyrate and tetrabenzoate were prepared. These powdered esters showed three different colors, i. e., orange (A-type), dark yellow (B-type) and yellow (C-type), according to the kinds of solvents used for the crystallization (A-and C-type) or heating procedure (B-type). The chemical structures of these esters were discussed by comparing visual absorption, 1H nuclear magnetic resonance, X-ray diffraction, electron spin resonance, excitation, emission and infrared spectra.
The color of riboflavin tetraesters in the solid state did not rely upon the kinds of ester groups but upon the interactions between their isoalloxazine groups.View full abstractDownload PDF (2666K) -
YASUHIRO SHIBATA, ISAO TAKEUCHI, YOSHIKI HAMADA1988 Volume 108 Issue 12 Pages 1148-1153
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSReissert Henze reactions of phenanthroline N-oxides (1-2) with methanesulfonyl chloride gave the corresponding α-(5, 7) and, β-methylsulfonylphenanthroline (6, 8), respectively.
In a similar manner, 8-methylsulfonylated 1-oxide (10) was obtained from 1, 7-phenanthroline 1, 7-dioxide (3), but the reaction of 4, 7-phenanthroline 4, 7-dioxide (4) resulted in the recovery of dioxide (4). The reactions of 1 4 with benzenesulfonyl chloride used instead of methanesulfonyl chloride did not give any reaction products, except tor the reaction of 2 giving 4, 7-phenanthroline-3-carbonitrile.
Meisenheimer reactions of 1-3 with phosphorous oxychloride gave the corresponding α-(11, 14, 17), β-(12, 15, 18), and r-chlorophenanthrolines (13, 16, 19), respectively, while in a similar reaction, the a-chlorophenanthroline (20) as a sole product was obtained from 4 in a high yield.
As for 11 18, 20, minimum inhibitory concentrations (MIC) were 12.5μg/ml for Pseudomonas aeruginosa.View full abstractDownload PDF (489K) -
TSUNEO NAMBA, MASAYUKI MIKAGE, SHAO-QING CAI1988 Volume 108 Issue 12 Pages 1154-1167
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSTo identify the botanical origins of crude drugs derived from Adiantum spp. used mainly in China, India etc., the pharmacognostical study on Adiantum plants of Asia was carried out. This paper dealt with the anatomical characters of seven Adiantum species of series Caudata CHING growing in China and neighbouring countries. The results were as follows:(I) These seven species can be distinguished separately in the presence of wing and the shape of the transection of the xylem in stipe, the presence and shape of hair, the position of guard cells relative to the subsidiary cells and the shape of the transection of abaxial and adaxial margins of pinnule, etc.;(II) All these seven species have two characters which differ from the species of other series, namely, the larger tracheids present at the dorsal side of the xylem of stipe and one or two spicular cells (fibres) are observed in the upper epidermis above most veins;(III) On the basis of the abovc results the crude drug Zhu-zong-cao from Sichuan of China was found to be derivcd from Adianmm capillus-junonis, Bian-ye-tie-xian-jue from Taiwan derived from A. caudatum, Tie-xian-jue from Taiwan and Persia Oshan from Dacca of Bangladesh derived from A. philippense.View full abstractDownload PDF (9243K) -
TSUNEO NAMBA, MASAYUKI MIKAGE, SHAO-QING CAI1988 Volume 108 Issue 12 Pages 1168-1178
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSThis paper dealt with the anatomical characters of two species belonging to series Pedata and four species belonging to series Flabellulata of genus Adiantum, which grow in China and neighbouring countries. The results were as follows:(I) These four Flabellulata species can be distinguished from one another by the distribution or shape of hairs, the distribution of stomata in pinnule, the shape of the cells of supporting sheath in the transection of root, etc. But the two Pedata species showed the same anatomical characters with each other.(II) Plants of the two series are distinguishable, that is, four Flabellulata species, all having hairs in the blade or petiole of pinnule, most veins terminating at the upper margin, a stele (or xylem) branching into two meristeles (or xylems), while Pedata species have one stele and xylem which do not branch but show U-shape in the transection of lower and basal parts of the stipe.(III) On the basis of above results, it was clarified that the crude drugs, Tie-si-cao, Jin-tou-wugong, Xiao-hao-yin-fen-bei-jue and Shi-bi-huang from Taiwan, Hei-gu-cao from Hongkong, Hei-jiao-jue from Guangxi and Zhu-zong-cao from Sichuan of China were all derived from A. flabellulatum, and Seki-cho-sei from Nagoya of Japan was derived from A. pedatum.View full abstractDownload PDF (11181K) -
TSUNEO NAMBA, MASAYUKI MIKAGE, SHAO-QING CAI1988 Volume 108 Issue 12 Pages 1179-1187
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSThe anatomical characters of seven species belonging to series Venusta of genus Adiantum from China and neighbouring countries are described. The results were as follows:(I) These seven species can be distinguished from one another by the distribution of stomata and spicular cells (fibres); whether the supporting sheath border on the epidermis in the ultimate pinnule or not; the shape of the xylem in transection of the stipe; the number of cells of supporting sheath in the root, etc. with the exception that A. davidi and A. venustum showed the same anatomical characters.(II) All these seven species have two characters which differ from the species of other series reported previously by us, that is, the shape of both margins of pinnule are acute in transection, and the upper epidermal cells of intercostal areas are transversely elongated or isodiametric in transection.(III) It was found that the crude drug Zhu-zong-cao from Yunnan province of China, was derived from A. bonatianum.View full abstractDownload PDF (3634K) -
SHIZUO NAKAJIN, KAZUAKI TAKAHASHI, MASATO SHINODA1988 Volume 108 Issue 12 Pages 1188-1195
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSThe inhibitory effect of 20β-hydroxy-C21-steroids on oxygenase reaction, Δ 16-C19-steroid synthetase, 17α-hydroxylase and C17, 20-lyase activities catalyzed by pig testicular cytochrome P-450 (17α-hydroxylase/lyase) were studied.Δ 16-C19-Steroids synthetase, 17α-hydroxylase and C17, 20-lyase activities were competitively inhibited by 3β, 20β-dihydroxypregn-5-ene, 3β, 17α, 20β-trihydroxypregn-5-ene, 20β-hydroxypregn-4-en-3-one and 17α, 20βdihydroxypregn-4-en-3-one, and K, values for these steroids were 0.11 0.17 μM, 0.36-0.58 μM, 0.68-1.25μM and 8.11-10.1μM, respectiveiy.
Substrate-induced difference spectra with those steroids were examined. 3β, 20βdihydroxypregn-5-ene and 20β-hydroxypregn-4-en-3-one showed typical type I difference spectra (peak at 386 nm and trough at 420 nm). However, 3β, 17α, 20β-trihydroxypregn-5-ene and 17α, 20β-dihydroxypregn-4-en-3-one showed typical reverse type I (or modified type II) difference spectra (peak at 421 nm and trough at 385 nm). From those results of the spectral titration, it was indicated that 3β, 20β-dihydroxypregn-5-ene (or 3β, 17α, 20βtrihydroxypregn-5-ene) and cytochrome P-450 (17α-hydroxylase/lyase) formed a one-to-one complex with very high affinity.
In addition, the reduction rate of cytochrome P-450 (17α-hydroxylase/lyase) with Na2S2O4 was decreased by the addition of those 20β-hydroxy-C21-steroids.View full abstractDownload PDF (858K) -
TAKAYUKI OIKAWA, NAGAHIKO YUMITA, SHIGEKI SHIBASAKI, RYUICHIRO NISHIGA ...1988 Volume 108 Issue 12 Pages 1196-1202
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSThe mesenteric membrane permeability between the blood and peritoneal cavity was studied pharmacokinetically by using rat for two drugs; salicylamide (SAM) and salicylic acid (SA).
The intraperitoneal cavity was perfused continuously and SAM and SA were given by i. v. administration and from the perfusate.
But, benzoic acid (BA) was given only by i. v. administration.
The drug concentration in the blood and intraperitoneal perfusate were determined and analyzed pharmacokinetically.
The transport rate constants from the blood and intraperitoneal cavity of SAM were 20.8±1.2-10-3 and 40.3±2.2-10-3min-1, respectively. While those of SA were 0.97±0.33-10-3 and 6.6± 1.7-10-3 min-1, respectively.
The ratio of cumulative amount transported to the intraperitoneal cavity after i. v. administration to the dose administered was estimated by the area under the blood concentration-time curve. The values for SAM, SA and BA were 50.4, 6.8 and 5.6%, respectively.View full abstractDownload PDF (605K) -
HIROAKI SHIMIZU, SHIGERU HAYASHIDA, NAGATOSHI WAGATSUMA1988 Volume 108 Issue 12 Pages 1203-1208
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSPhotodecomposition and stabilization of sodium guaiazulenesulfonate (I) in aqueous and various organic solvents were studied. It was found that photodecomposition of I was biphasic, and the results fitted the zero-order kinetic pattern.
Further, this photolysis was inhibited by the addition of halogen ions, and univalent and bivalent metal ions.
In the case of replacement with N2 and the addition of hydroquinone or pyra zoloned erivatives, I was also stabilized. It was found that I formed the charge transfer complex with pyrazolone derivatives, composing of molar 1: 1, which may consequently stabilize the photolysis.View full abstractDownload PDF (611K) -
HIDEAKI SHIMADA, MORIO KIYOZUMI, TOSHIYA HONDA, SHOJI KOJIMA1988 Volume 108 Issue 12 Pages 1209-1214
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSThe effects of three chelating agents, sodium N-benzyl-o-glucamine dithiocarbamate (NBG-DTC), 2, 3-dimercaptopropanol (BAL), and D-penicillamine (D-PEN), on the distribution and excretion of inorganic mercury were compared in rats exposed to HgCl2. Rats were injected i. p. with 203HgCl2 (300μg and 2μCi of 203Hg/kg) and after 24h they were treated with the chelating agents (a quarter of an LD50) every day for 7d. NBG-DTC and BAL promoted fecal and urinary excretions of mercury, while o-PEN promoted urinary excretion of mercury. NBG-DTC and BAL reduced the contents of mercury in the liver and kidney. BAL reduced the contents of mercury in the spleen, testes, heart, pancreas, and lung. D-PEN reduced only the content of mercury in the kidney. These chelating agents did not result in a redistribution of mercury to the brain, heart, and lung. The treatment with these chelating agents decreased the amounts of Zn, Fe, Cu, and Mn in the tissue as compared with control. The growth of rats was little retarded by treatment with these chelating agents. There was no damage to the liver and kidney by treatment with NBG-DTC. The results of this study reveal that the injection of NBG-DTC to rats pretreated with mercury can effectively remove mercury from the body as well as the injection of BAL.View full abstractDownload PDF (683K) -
TETSUYA ASAMIZU, KAZUYUKI AKIYAMA, ICHIRO YASUDA1988 Volume 108 Issue 12 Pages 1215-1218
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSHairy roots were induced in seedlings of Cassia obtusifolia inoculated with Agrobacterium rhizogenes. Established hairy root clone in shaking culture synthesized several anthraquinones; 8-O-methylchrysophanol, chrysophanol, emodin and physcion. Their yields were maximized in the late exponential growth phase of shaking-culture. The anthraquinones composition of hairy roots was different from that of mature seeds (Ketsumeishi) and relatively similar to that of the primary roots of seedling.View full abstractDownload PDF (430K) -
SHIZUO NAKAJIN, SHUJI OHNO, MASATADA AOKI, MASATO SHINODA1988 Volume 108 Issue 12 Pages 1219-1222
Published: December 25, 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSThe inhibitory effect of various inhibitors of steroid metabolizing enzyme against 20β-hydroxysteroid dehydrogenase (20β-HSD) purified from the pig testes was investigated. The dehydrogenase activity was considerably inhibited by spironolactone, SU 10603 and cyanoketone. Those compounds showed a concentration-dependent and competitive inhibitory effect and the inhibition constants (K1) were 11.2μM for spironolactone, 22.3μM for SU 10603 and 42.8μM for cyanoketonc. However, 20β-HSD activity was not inhibited by SU 8000, 1-(o-chlorophcnym)-1-(p-chloropheay1)-2, 2-dichloroethane, aminoglutethimide and SKF 525A.View full abstractDownload PDF (325K) -
1988 Volume 108 Issue 12 Pages 1223
Published: 1988
Released on J-STAGE: July 11, 2011
JOURNAL FREE ACCESSDownload PDF (17K)
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