Furoquinolines, viz., kokusagine (I), maculine (II), dictamnine (III) and 6-methoxy-dictamine (IV) were synthesized via ethyl 2-anilino-4, 5-dihydro-4-oxofuran-3-carboxylate derivatives. 6-Methoxy-2-methyldictaminne (V) and its dihydro-derivative (XXI) were synthesized via analogous ethyl 4, 5-dihydro-2-(4-methoxyanilino)-5-methyl-4-oxofuran-3-carboxylate. Stereochemical assignments of 2, 3-cis and trans 2, 3-dihydro-3-hydroxy-4, 6-dimethoxy-2-methylfuro[2, 3-b]quinoline having insect antifeeding activity were made on the basis of their spectrometric data (PMR and MS).

抄録全体を表示

Konjac glucomannan, a reserve polysaccharide from Amorphophallus koniac tubers was isolated in a homogeneous state and is known to contain D-mannose and D-glucose in a molar ratio of 1.6:1. Survival of some monosaccharides after the periodata oxidation and subsequent reduction of knojac glucomannan suggested that it was composed mainly of β-1, 4 linkages, however, there was some branching in the polysaccharide. By analysis of the hydrolyzate of the permethylated sample by GC-MS, the branching structure through C3 of both D-mannose and D-glucose residues was confirmed. Yields of O-methyl mugars were also determined.
The results indicate a branched structure for a native and non-denatured specimen of konjac glucomannan.

抄録全体を表示

Effects of temperature, atmosphere and time of heat treatment of albumin on mutagenic activity toward Salmonella typhimurium TA 98, as well as the yield of mutagens, 3-amino-1-methyl-5H-pyrido[4, 3-b]indole and 2-amino-9H-pyrido[2, 3-b]indole were determined in pyrolysis products. Mutagenic activity and mutagen content in the pyrolyzate increased progressively with heating temperature from 200 to 700°C. The effect of heating temperature differed depending on the heating atmosphere, i.e., N₂ or air. At 200°C, pyrolyzate mutagenic activity increased with heating time up to 7h, but the mutagenic principles indicated above were not detected.

抄録全体を表示

(Z)-Alkenols and Their acetates have been synthesized by the Wittig reaction of (ω-hydroxyalkyl)triphenylphosphonium salts with alkanals by a convenient procedure. The geometrical purity of the products was evaluated to be no less than 95% of the (Z)-configu-ration by means of GLC with a glass capillary column coated with CHDMS.

抄録全体を表示

Interaction of L-lysine with Co(II) and Cu(II) ions has been studied using ¹H- and ₁₃C- NMR and solution absorption spectrometry. In L-lysine-Co²⁺ solution in D₂O (100:1 in concentration), coordination interaction of the α-amino and carboxyl groups with Co²⁺ occurs from the neutral to alkaline pD region, whereas no interaction of the ε-amino group was observed throughout the whole pD region. On the other hand, in L-lysine-Cu²⁺ solu-tion, the ε-amino group also takes part in complexation in the higher pD region (pD_??_10). Structural changes in complexation of L-lysine with the divalent cations along with pD variations in aqueous solution are discussed. Dissociation constants of the three functional groups were obtained by ¹H-NMR chemical shifts; pKa₁=2.2, pKa₂=9.5 and pKa₃=11.2.

抄録全体を表示

Multipe forms (D-I and D-II) of GTP cylcohydrolase, the first enzyme in pteridine biosynthesis, was demonstrated in Serratia indica by DEAE-cellulose chromatography. D-II was purified homogeneously. D-I contained small amounts of inactive protein. Both molecular weights were estimated to be 200000. D-II consisted of 8 subunits with the same molecular weight of 25000. The Km values (Km₁ and Km₂) for GTP were 3.2μM and 0.61μM for D-I, and 0.44μM and 5.5μM for D-II, respectively. Bivalent cations (Cu²⁺, Cd²⁺, Hg²⁺) inhibited the enzymes. Univalent cations (K⁺, Na⁺ and Li⁺) activated the enzymes.

抄録全体を表示

The existence of aminoglycoside-4'-nucleotidyltransferase [AAD(4')] was demonstrated in the cellfree extract of B. brevis. This enzyme was purified about 100-fold over the cellfree extract by column chromatography using DEAE-cellulose and affinity chromatography using butirosin A-Sepharose 4B.
AAD(4') of B. brevis catalyzed the transfer of nucleotides to the 4'-hydroxyl group on amino-hexose, a constituent of 2-deoxystreptamine aminoglycosides. Ribo- and deoxyribonucleoside triphosphates were active as nucleotidyl donor. The pH optimum for the reaction was in the range of 5.5 to 6.0. AAD(4') activity was dependent upon divalent metal-ions: Mn²⁺, Zn²⁺, Mg²⁺ and Co²⁺.
The molecular weight as determined by gel filtration on a Sephadex G-100 column was approximately 45000.

抄録全体を表示

The effects of quinolinic acid analogues and 5-phosphoribosyl-l-pyrophosphate analo-gues on the activity of quinolinate phosphoribosyltransferase (EC 2.4.2.19) crystallized from Alcaligenes eutrophus subsp. quinolinicus have been investigated. Sugar and metal contents, amino acid composition and active site of the crystalline enzyme were also examined. The C-2 carboxyl group and pyridine ring of quinolinic acid and 5-phosphate of 5-phospho-ribosyl-l-pyrophosphate took part in the binding to the enzyme. This enzyme did not contain metal and was found to contain sugar about 1% as mannose. The amino acid composi-tion of this enzyme was compared with that of hog liver enzyme. Sulfhydryl, amino and imidazole groups may exist in the active site of the enzyme.

抄録全体を表示

Effects of various compounds on crystalline quinolinate phosphoribosyltransferase (EC 2.4.2.19) from hog kidney were investigated. Phthalic acid and Pyrazine-2, 3-dicarboxy-lic acid were both competitive inhibitors for quinolinic acid. The enzyme activity was inhibited by heavy metal divalent cations and trivalent cations. Nucleoside triphosphates also inhibited the enzyme activity and this inhibition was recovered by raising the MgCl₂ concentration. Glycerol activated the enzyme activity at pH from 4.0 to 4.4, while it inhibited at above pH 5.0. Isoleucine content of the crystalline enzyme was extremely low (17 residues per mol of enzyme). The total SH groups determined by 5, 5'-dithio-bis-(2-nitrobenzoic acid) were 30 groups per mol of enzyme protein in the presence of guanidine hydrochloride. The enzyme activity was inhibited by 5, 5'-dithio-bis-(2-nitrobenzoic acid), p-chloromercuribenzoic acid, 2, 4, 6-trinitrobenzenesulfonic acid, β-naphthoquinone-4-sulfonic acid and diethylpyrocarbonate. The results suggest that SH, amino and imidazole groups exist in the active site of the enzyme. pKe value of the enzyme was 9.25.

抄録全体を表示

NADP-Dependent D-glucose dehydrogenase (EC 1.1.1.47) was crystallized for the first time from cytosol fraction of Gluconobacter suboxydans IFO 12528. Purification of the enzyme was successfully performed by column chromatography on DEAE-Sephadex A-50 and affinity chromatography by blue-dextran Sepharose 4B. The enzyme was purified about 1, 800-fold with an overall yield of 30%. Crystalline enzyme preparation was homogeneous in disc gel electrophoresis and analytical ultracentrifugation. The enzyme was highly specific for NADP and completely inactive with NAD. NADPH yielded in D-glucose oxidation to D-glucono-δ-lactone was reoxidized to NADP by the old yellow enzyme which existed in the same cytosol fraction of the organism. Cyclic regeneration of NADP occurred smoothly in the presence of D-glucose dehydrogenase, old yellow enzyme and catalase, even when a limited amount of NADP or NADPH was present in the reaction mixture.

抄録全体を表示

High phosphate accumulating bacteria were isolated by autoradiography. One isoate, Arthrobacter globiforrnis PAB-6 accumulated phosphate intracellularly at 20% of dry cell mass in a simple synthetic medium. This amount was 3_??_7 times higher than type cultures examined. Almost no phosphate was released into the medium after cessation of growth. Fifty percent of total intracellular phosphate was fractionated as nucleic acids, while 20% each was recovered from cold PCA soluble fractions and polyphosphate fractions. The large content of nucleic acids in this bacterium appeared due to increased RNA content, specifi-cally 4 S RNA fraction.

抄録全体を表示

The influence of cultural conditions was examined on phosphate accumulation of the high phosphate accumulating bacterium, Arthrobacter globiformis PAB-6. This bacterium utilized nitrate and nitrite, as well as ammonium salts, as nitrogen source, and polyphosphates, organic phosphates, as well as inorganic phosphate, as phosphorus source. Ferric and calcium ions were found to be essential for high phosphate accumulation. Both growth and phosphate uptake were stimulated by addition of certain amino acids. Phenylalanine had an especially highly stimulatory effect. Optimal temperature and pH for efficient phosphate uptake were 25°C and between 7 and 8, respectively.

抄録全体を表示

New sterylglycosides; tetraglycosylsterol and pentaglycosylsterol were isolated in addition to the known mono-, di- and triglycosylsterols from rice bran and studied for the chemical structures. In both the lipids, the principal sterol components were sitosterol, campesterol and stigmasterol; the component sugar was essentially only glucose, glucose units of which were linked with β 1, 4-bonds. Based on these data, the representative tetraglycosylsterol and pentaglycosylsterol were characterized as cellotetraosylsitosterol and cellopentaosylsitosterol, respectively.

抄録全体を表示

From the volatile flavor concentrate of shoyu, acidic I and acidic TI fractions were se-parated. Shoyu was also directly extracted with CH₂Cl₂ in order to cover the components that were not obtained by the above method, and the extract was separated into ten (A_??_J) fractions. C_??_I fractions were acidic ones. The above fractions were successively analy-zed by gas chromatography and combined gas chromatography-mass spectrometry. Con-sequently, 93 components were identified, 36 of which have not been reported previously as constituents of shoyu. The identified compounds were 15 alcohols, 15 carbonyls, 9 esters, 4 lactones, 6 furans, 3 furanones, 5 pyrones, 7 phenols, 13 acids and 16 other compounds. Organoleptically, the caramel-like aroma compounds among them are important for the characteristic flavor of shoyu. 4-Hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) and 4-hydroxy-5-methyl-3(2H)-furanone seem to be important, and particularly, in view of the content and the organoleptic property, HEMF is concluded to be the main and most important constituent of the characteristic flavor of shoyu.

抄録全体を表示

An extracellular polysaccharide (I) was isolated from the viscous culture filtrate of S. libertiana and subjected to methylation study, enzymic hydrolysis and Smith degradation. From the results, I was concluded to be a polysaccharide composed of a backbone of β-(1→3)-linked D-glucopyranosyl residues and possessed a single β-n-glucopyranosyl residue joined through C-6 of every third D-glucopyranosyl residue of the backbone.

抄録全体を表示

An N-acetylglutamokinase-deficient arginine-requiring mutant, KY9390 and an N-acetylornithine aminotransferase-deficient arginine-requiring mutant, AA-7 were derived from a wild-type strain and an L-arginine-producing mutant of Corynebacterium glutamicum, respectively. KY 9390 accumulated 7.5mg per ml of N-acetylglutamic acid and AA-7 accumulated 2mg per ml of N-acetylglutamate-γ-semialdehyde, intermediates of arginine biosynthesis, in a culture medium.
The production of N-acetylglutamate-β-semialdehyde by AA-7 was not affected by the concentration of L-arginine in the medium, whereas that of N-acetylglutamic acid by KY 9390 was inhibited by the addition of L-arginine in the medium.

抄録全体を表示

The cleavage pattern of Streptomyces chromosomal DNA was examined with various restriction endonucleases under agarose gel electrophoresis, and Sall endonuclease was found to cleave Streptomyces DNA efficiently. Chromosomal DNA segments from four Streptomyces species were cloned into Escherichia colt vector plasmids pTA2070 and pBR322 by the “Sail-ligase method.” The number of clones possessing hybrid plasmids was large enough to be termed as a gene bank. However, there was no clone in the four gene banks complement-ing E. colt leu, ade, or thy auxotrophic marker. No clone was isolated that expressed the streptomycin phosphotransferase activity of Streptomyces griseus as a determinant of streptomycin resistance in E. coli. It was suggested that E. coil does not allow functional expression of Streptomyces genes.
A streptomycin resistant plasmid RSF1010 of E. coil was linked to a pTA2070-S. griseus DNA hybrid plasmid, by the “EcoRI-ligase method, ” in order to construct a possible cloning vector usable in the streptomycete.

抄録全体を表示

The title lactone trans-7 with a partial structural resembling picrotoxinin 1, which is an antagonist of GABA, and some related lactones were synthesized, and their insecticidal activities were assayed on susceptible and resistant housefly strains. Lactone trans-7 showed the highest activity among the tested compounds in both strains. The configuration of the isopropyl group at C₈ position was important for the insecticidal activity.

抄録全体を表示

L-Lysine α-oxidase, a new fungal enzyme that catalyzes the a-oxidative deamination of L-lysine, inhibited the growth of L5178Y mouse leukemic cells in vitro. Complete inhibition of the growth was observed at the enzyme concentration of 3.3mU/ml, and the concentration which induces 50% inhibition of the cell growth was 1mU/ml. DNA synthesis of L5178Y cells was inhibited more strongly by the enzyme treatment than protein and RNA syntheses were. The enzyme was also shown to have antitumor activity against L1210 mouse leukemia in vivo. Intraperitoneal injection of the dose of 70 units/kg/day on day I to 5 resulted in an increase of lifespan by 34 to 48 %. The enzyme reduced L-lysine level in both RPMI 1640 medium and plasma of BDF₁ mice. The plasma half-life time of the enzyme was about 2 hr. In addition to the growth-inhibitory effect based on the enzymatic depletion of L-lysine, the cytotoxic effect of H₂O₂ formed enzymatically on L5178Y cells also contributed to the antitumor activity in vitro.

抄録全体を表示

Bracken fern constituents, pterosin H, F, I, O, Z, B and V, were identified as factors inducing abnormal development of sea urchin embryos. These compounds were also found to have cytotoxic effects on a ciliate, Paramecium caudatum. Feeding experiments showed that they did not inhibit DNA synthesis of the sea urchin embryos in a specific manner.

抄録全体を表示

Glycerol oxidase, a novel glycerol oxidizing enzyme, has been found in several strains belonging to genera Aspergillus, Neurospora, and Penicillium. Aspergillus japonicus AT 008 showed significantly high enzyme activity. Glycerol oxidase was formed in the mycelia of the fungi grown on glycerol as a carbon source. The enzyme was purified from the cell-free extract of Aspergillus japonicus AT 008 by a procedure involving fractionation with ammonium sulfate, column chromatographies on DEAE-Sephadex A-25 and hydroxylapatite, and gel filtration on Sephadex G-200. The overall purification was approximately 190-fold with a yield of 35.5%. The purified enzyme gave a single band on acrylamide gel electrophoresis. The enzyme catalyzed the oxidation of glycerol using molecular oxygen as a primary electron acceptor and producing glyceraldehyde and hydrogen peroxide according to the following scheme: CH₂OHCHOHCH₂OH+0₂→CHOCHOHCH₂OH+H₂O₂.

抄録全体を表示

Effects of isopentenyl alcohol and its homologues on the ubiquinone production by various microorganisms were examined. A new method using methionine-methyl (³H) to estimate relative content of ubiquinone in bacterial cells was devised. The results obtained by this method corresponded to those obtained by ordinary method. Isopentenyl alcohol, dimethylallyl alcohol or geraniol enhanced ubiquinone production by Pseudomonas schuylkilliensis when added to the culture media at the final concentration of 1×10^-3M, whereas farnesol and the longer chain homologues were inhibitory to the ubiquinone production. Isopentenyl alcohol was also effective to enhance the ubiquinone production by yeasts and fungi tested when added to their culture media at the final concentration of 1.5×10^-3M. Geraniol or farnesol added were inhibitory to their growth at the same concentration.

抄録全体を表示

Seven kinds of lipase were immobilized to Sepharose 4 B, porous glass beads and ionexchange resins. Lipase immobilized to porous glass beads was most suitable for the treatment of yolk-contaminated egg white. Optimum pH and temperature were not varied by the immobilization. The immobilized lipoprotein lipase from Pseudomonas fluorescens and lipase from Rhizopus delemar were applied to the treatment of yolk-contaminated egg white. The foam stability of the spray-dried egg white solution containing 0.05% yolk was completely recovered by the 30min's treatment with both immobilized lipases. This demonstrated the feasibility of improving the foaming properties of yolk-contaminated egg white by the immobilized lipase treatment.

抄録全体を表示

DL-(1, 3/2)-3-Acetamido-1, 2-di-O-benzylcyclohex-4-enediol (IIIa) and DL-(1, 3/4)-1-ace-tamido-3, 4-di-O-benzylcyelohex-5-enediol (IIIb) were synthesized from DL-trans-1, 2-di-O-benzylcyclohex-3-enediol (I) via the corresponding azide derivatives (IIa-b) prepared by bromination and subsequent treatment with sodium azide in N, N-dimethylformamide. Compounds (IIIa and IIIb) were converted into a variety of deoxyinosamine and deoxyinosadiamine derivatives via epoxides (VIII and IX) or by cis-hydroxylation with osmium tetroxide. Hexaacetyl-_rac-inosamine-1 (XVIIIc) was synthesized from DL-(1, 3, 4/2, 5)-3-acetamido-1, 2-di-O-benzyl-5-bromocyclohexanetriol (VIa) via conduramine derivatives (XVIIa-c). Conformational analysis of partially O-benzylated aminocyclitol derivatives were studied by means of NMR spectroscopy.

抄録全体を表示