Showing papers in "Agricultural and biological chemistry in 1970"
TL;DR: In 1970, Nojirimycin was shown to be a potent inhibitor of Glucosidase as discussed by the authors, and was used as a drug for the treatment of influenza.
Abstract: (1970). “Nojirimycin” as a Potent Inhibitor of Glucosidase. Agricultural and Biological Chemistry: Vol. 34, No. 6, pp. 966-968.
133 citations
89 citations
TL;DR: Bitter peptides were isolated from the tryptic hydrolysate of casein using n-butanol extraction, acidic precipitation at pH 5.4, gel filtration with Sephadex G-25, ion exchange chromatography with Dowex 50 W and paper chromatography.
Abstract: Bitter peptides were isolated from the tryptic hydrolysate of casein. Fractionation and isolation were carried out using n-butanol extraction, acidic precipitation at pH 5.4, gel filtration with Sephadex G-25, ion exchange chromatography with Dowex 50 W and paper chromatography. Three kinds of bitter peptides were purified. The primary structures of these peptides were proposed as follows; BP-I, Gly-Pro-Phe-Pro-Val-Ileu; BP-II, Phe-Phe-Val-Ala-Pro-Phe-Pro-Glu-Val-Phe-Gly-Lys; BP-III, Phe-Ala-Leu-Pro-Gln-Tyr-Leu-Lys. These peptides were very bitter in a 0.1% solution.l-Tyrosine, l-phenylalanine and their derivatives were also tasted. The importance of the position of bitter amino acids in the peptide in the development and strengthening of its bitter taste is discussed.
79 citations
TL;DR: Selective cleavage of the side chains of various sterols at C-17, giving rise to androsta-1,4-diene-3,17-dione (ADD), occurred in the presence of α,α′-dipyridyl by microorganisms of the following genera.
Abstract: Cholesterol decomposing ability of 1589 microbial strains was examined. Two hundreds and thirty six strains from actinomycetes, bacteria, molds, and yeasts were found capable of oxidizing cholesterol into cholestenone. Cholesta-1,4-dien-3-one was produced by 5 strains of Streptomyces. The complete decomposition of cholesterol molecule was observed in the genera: Arthrobacter, Bacillus, Brevibacterium, Corynebacterium, Microbacterium, Mycobacterium, Nocardia, Protaminobacter, Serratia, and Streptomyces. α,α′-Dipyridyl and arsenite inhibited decomposing enzymes giving rise to cholestenone, cholesta-1,4-dien-3-one, and an intermediate probably devoid of the sterol side chain.Selective cleavage of the side chains of various sterols at C-17, giving rise to androsta-1,4-diene-3,17-dione (ADD), occurred in the presence of α,α′-dipyridyl by microorganisms of the following genera: Arthrobacter, Bacillus, Brevibacterium, Corynebacterium, Microbacterium, Mycobacterium, Nocardia, Protaminobacter, Serratia, and Strept...
77 citations
TL;DR: A strain of Serratia, isolated from an intestinal canal of a silkworm, produced a large quantity of protease, the enzyme was extracellular and was named Serratiopeptidase, tentatively.
Abstract: A strain of Serratia, isolated from an intestinal canal of a silkworm, produced a large quantity of protease. The enzyme was extracellular and was named Serratiopeptidase, tentatively. Protease pro...
56 citations
TL;DR: In this article, the isolation and structure elucidation of three new insecticidal cyclodepsipeptides, Destruxins C and D and Desmethyldestruxin B, produced by Metarrhizium anisopliae.
Abstract: (1970). Isolation and Structure Elucidation of Three New Insecticidal Cyclodepsipeptides, Destruxins C and D and Desmethyldestruxin B, Produced by Metarrhizium anisopliae. Agricultural and Biological Chemistry: Vol. 34, No. 5, pp. 813-816.
54 citations
TL;DR: The chemical constitutions of the pungent principle of Capsicum were investigated in this paper, and the chemical structure of nordihydrocapsaicin was determined as N-(4-hydroxy-3-methoxybenzyl)-7-methyl octanamide.
Abstract: The chemical constitutions of the pungent principle of Capsicum were investigated. These principles are assumed to consist of capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homodihydrocapsaicin and two or more analogues of these materials. Thin-layer chromatography and open tubular gas chromatography showed that the natural pungent mixture contains no cis-isomer of capsaicin. The chemical structure of nordihydrocapsaicin was determined as N-(4-hydroxy-3-methoxybenzyl)-7-methyloctanamide by gas chromatography, infrared spectroscopy, mass spectrometry and nuclear magnetic resonance spectroscopy. In addition, homodihydrocapsaicin was identified as N-(4-hydroxy-3-methoxybenzyl)-9-methyl-decanamide. These identities were also proven by comparison with synthetic samples.
53 citations
TL;DR: The results showed that the inactivation of lipoxygenase took place in consonance with the autoxidation of NDGA, one of the most effective inhibitors among the phenolic antioxidants tested.
Abstract: The effect of conventional antioxidants on soybean lipoxygenase reaction was examined. Inhibitory activities of o-diphenols such as pyrocatechol, homocatechol, propyl gallate and NDGA were higher than those of m- and p diphenols. The mode of inhibition by NDGA, one of the most effective inhibitors among the phenolic antioxidants tested, conformed to a competitive type and not to an induction period type. Under certain conditions, NDGA could be an irreversible inactivator for the enzyme. The effect of NDGA on the enzyme reaction could not be completely explained by the coupled oxidation theory. The inactivation by NDGA were effectively prevented by either of adding catalase, of incubating under anaerobic condition or in low pH medium or of adding borate. These facts showed that the inactivation of lipoxygenase took place in consonance with the autoxidation of NDGA.
49 citations
TL;DR: The chemical constitutions of the pungent principle of Capsicum were investigated in this article, and the chemical structure of nordihydrocapsaicin was determined as N-(4-hydroxy-3-methoxybenzyl)-7-methyl octanamide.
Abstract: The chemical constitutions of the pungent principle of Capsicum were investigated. These principles are assumed to consist of capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homodihydrocapsaicin and two or more analogues of these materials. Thin-layer chromatography and open tubular gas chromatography showed that the natural pungent mixture contains no cis-isomer of capsaicin. The chemical structure of nordihydrocapsaicin was determined as N-(4-hydroxy-3-methoxybenzyl)-7-methyloctanamide by gas chromatography, infrared spectroscopy, mass spectrometry and nuclear magnetic resonance spectroscopy. In addition, homodihydrocapsaicin was identified as N-(4-hydroxy-3-methoxybenzyl)-9-methyl-decanamide. These identities were also proven by comparison with synthetic samples.
49 citations
TL;DR: One of the lipoxygenase isozymes whose activity was dependent on calcium ion was isolated from soybean meal, and its protein and catalytic natures were compared with those of relatively well-defined one.
Abstract: One of the lipoxygenase isozymes whose activity was dependent on calcium ion (lipoxygenase b) was isolated from soybean meal, and its protein and catalytic natures were compared with those of relatively well-defined one (lipoxygenase a). Lipoxygenase b was found different from lipoxygenase a in electrophoretic mobility on polyacrylamide gel, pH-activity profile and sensitivity to added calcium ion. The isozymes were separated from each other by fractional precipitation with ammonium sulfate and following ion exchange chromatography. Added calcium ion was found to stimulate significantly the enzymic activity of lipoxygenase b while to be rather inhibitory for that of lipoxygenase a. Hemoproteins were also stimulated by calcium ion in catalyzing the oxidation of colloidal linoleate.
44 citations
TL;DR: In this paper, the acid-precipitated fraction of soy protein incubated for 2 hours with Molsin (i.e. 2 hr-proteolyzate) showed the following composition: 10% trichloroacetic acid (TCA) insoluble fraction, 47.52%; 10% TCA soluble peptide fraction, 52.02%; and free amino acid fraction, 0.46%.
Abstract: Soy proteins were incubated with a microbial acid protease (Molsin) under the following condition: substrate concentration, 1%; enzyme-substrate ratio (by weight), 1/100; pH, 2.8; and temperature, 40°C—flavor components and related impurities are removable from crude soy-protein concentrates by their incubation for 2 hr under the above condition. The acid-precipitated fraction of soy protein incubated for 2 hr with Molsin (i.e. 2 hr-proteolyzate) showed the following composition: 10% trichloroacetic acid (TCA) insoluble fraction, 47.52%; 10% TCA soluble peptide fraction, 52.02%; and free amino acid fraction, 0.46%. Gel filtration of the 2 hr-proteolyzate gave an elution pattern showing its molecular weight distribution.In the process of the incubation of the acid-precipitated protein, the 10% TCA insoluble fraction showed increase in amino nitrogen content, its solubility in a phosphate buffer increased to change at 6 hr, and a hydrophobic amino acid share in this fraction increased gradually.In vitro dig...
TL;DR: Higher plastein yields were given by pepsin, α-chymotrypsin and papain as the well-known proteinases, and by Molsin (acid protease produced by Aspergillus saitoi), Coronase (neutral protease production produced by a certain Rhizopus), Bioprase (alkaline proteaseproduced by Bacillus subtilis), and other microbial proteases available in Japan.
Abstract: Several well-known proteinases (pepsin, α-chymotrypsin, papain and trypsin) and various microbial proteases available in Japan were investigated for pH dependence of their plastein-synthetic activities and also for that of their protein-hydrolytic activities. The optimum pH-values for synthesizing plasteins from a peptic hydrolyzate of soy protein existed in the range of pH 3 ~ 7, whereas those for hydrolyzing a denatured soy protein covered the range of pH 2 ~ 11. Based on ΔpH (optimum pH-value in synthesis minus that in hydrolysis), the enzymes used were classified into three types: pepsin type (ΔpH > 0), chymotrypsin type (ΔpH<0) and papain type (ΔpH = 0), with the exception of trypsin (not plastein-productive at any pH). Higher plastein yields were given by pepsin, α-chymotrypsin and papain as the well-known proteinases, and by Molsin (acid protease produced by Aspergillus saitoi), Coronase (neutral protease produced by a certain Rhizopus), Bioprase (alkaline protease produced by Bacillus subtilis), e...
TL;DR: In this paper, the relative sweetness of various sweet substances, such as sugars, synthetic sweetners, and amino acids, was evaluated by sensory analysis and clasification according to their patterns of the taste intensity curves.
Abstract: The sweetness of various sweet substances, such as sugars, synthetic sweetners, and amino acids were evaluated by sensory analysis. The relative sweetness varied in many ways as the concentration increased and the quantitative relationships between the sweetness and the concentration were established. The substances were clasified according to their patterns of the taste intensity curves.
TL;DR: In this article, the absolute structure of decumbin was presented as [II] by the following evidences: the configuration about C4 was determined as (S) by the benzoate rule on the tetrahydromonoketone (21).
Abstract: From the mycelium of Ascochyta imperfecta decumbin, C16H24O4, mp 203°C, was obtained in one percent yield.The absolute structure of decumbin was presented as [II] by the following evidences: The configuration about C4 was determined as (S) by the benzoate rule on the tetrahydromonoketone (21). The hydroxyl at C7 is α, because tetrahydrodecumbin (23) showed no intramolecular hydrogen bond, while its C7 epimer (24) did. Ring juncture was determined by ORD of a five membered ketone (16). Two double bonds were found to be trans from IR data. The stereochemistry of decumbin monoepoxide (7), tetrahydropyrans (12 and 13) was also studied. Plant tests of the twenty derivatives of decumbin on lucerne and rape revealed that the growth inhibition activity has close relation with the presence of double bond in the thirteen membered lactone ring.
TL;DR: The growth of Brevibacterium flavum No. 2247 was inhibited over 90% at a concentration above 1 mg/ml of α-amino-β-hydroxyvaleric acid, a threonine analogue, and the inhibition was reversed by the addition of l-threonine, and to lesser extent by l-leucine, l-isoleucine), l-valine and l-homoserine.
Abstract: The growth of Brevibacterium flavum No. 2247 was inhibited over 90% at a concentration above 1 mg/ml of α-amino-β-hydroxyvaleric acid, a threonine analogue, and the inhibition was reversed by the addition of l-threonine, and to lesser extent by l-leucine, l-isoleucine, l-valine and l-homoserine. l-Methionine stimulated the inhibition. Several mutants resistant to the analogue produced l-threonine in the growing cultures. The percentage of l-threonine producer in the resistant mutants depended on the concentration of the analogue, to which they were resistant. The best producer, strain B-183, was isolated from resistant strains selected on a medium containing 5 mg/ml of the analogue. Mutants resistant to 8 mg/ml of the analogue was derived from strain B-183 by the treatment with mutagen, N-methyl-N’-nitro-N-nitrosoguanidine. Among the mutants obtained, strain BB-82 produced 13.5 g/liter of l-threonine, 30% more than did the parental strain. Among the resistant mutants obtained from Corynebacterium acetoaci...
TL;DR: It is shown that among various grains, wheat and barley contain in the endosperm a toxic substance to brewing yeast, and the substance is easily extracted with a dilute sulfuric acid solution.
Abstract: It is shown that among various grains, wheat and barley contain in the endosperm a toxic substance to brewing yeast, and the substance is easily extracted with a dilute sulfuric acid solution. One unit of the toxicity is defined as the lowest amount of the extract which inhibits the yeast growth in 10 ml of wort medium. Two or more units of the toxicity not only inhibited the yeast growth, but also caused the death of yeast cells. Although the toxic effect was not observed when divalent metallic ions such as Ca2+, Zn2+ or Fe2+ were present at a concentration of 5 × l0−3 mole or more, the toxicity could be recovered by the addition of ethylene-diamine-tetra-acetate (EDTA). Genetic relationships on the content of the toxicity in wheat and barley and sensitivity of yeast strains to the toxicity are also presented.
TL;DR: A functional role of Co2+ and Mn2+ in the d-glucose- and d-xylose-isomerizing reactions by d-GLucose isomerizing enzyme obtained from the cells of Bacillus coagulans, strain HN-68 was investigated in this paper.
Abstract: A functional role of Co2+ and Mn2+ in the d-glucose- and d-xylose-isomerizing reactions by d-glucose-isomerizing enzyme obtained from the cells of Bacillus coagulans, strain HN–68 was investigated. (1) The enzyme required Co2+ and Mn2+ for d-glucose- and d-xylose-isomerizing activities, respectively. (2) The enzyme which bound the metal, Co2+- or Mn2+-enzyme, was active form. Co2+ was bound to the enzyme in a molar ratio of 4:1. (3) The rate of activation by metal ion varied with incubation pH. (4) The binding of substrate to the enzyme was completely independent in the presence of metal ions. (5) However, it seemed unlikely that the Co2+ and Mn2+ acted as catalyzer on the reaction. (6) The binding sites for Co2+ and Mn2+ were different from each other. (7) The experimental data obtained might be successfully explained in terms of the suitable conformational changes for d-glucose and d-xylose isomerization, which were induced in the catalytic sites of the enzyme by binding Co2+ and Mn2+, respectively.
TL;DR: In this article, the cold-pressed peel oil of Yuzu (Citrus junos) based on gas chromatography, infrared spectrometry, nuclear magnetic resonance spectrometer, and capillary GLC connected with fast-scan mass spectrometric.
Abstract: Eight monoterpenic hydrocarbons, 15 sesquiterpenic hydrocarbons, 6 aliphatic aldehydes, 1 aromatic aldehyde, 3 terpenic aldehydes, 1 terpenic ketone, 1 aliphatic ketone, 1 phenol, 1 phenol ether, 8 terpenic esters, 3 aliphatic alcohols, 9 monoterpenic alcohols, 9 sesquiterpenic alcohols, 1 aromatic alcohol, 5 fatty acids and 2 coumarin compounds were identified in cold-pressed peel oil of Yuzu (Citrus junos) based on gas chromatography, infrared spectrometry, nuclear magnetic resonance spectrometry and capillary GLC connected with fast-scan mass spectrometry. Structures of the sesquiterpenic hydrocarbons, γ-elemene and bicycloelemene are discussed.
TL;DR: In this paper, several strains were found to produce a large amount of cumic acid from p-cymene, including S449B1, B2, B3, B4 and B6.
Abstract: During the course of an investigation of the microbial assimilation of aromatic hydrocarbons, several strains were found to produce a large amount of cumic acid from p-cymene.Five strains, S449B1, B2, B3, B4 and B6, were isolated from soil with the aromatic hydrocarbon substrates. They all assimilated both p-cymene and cumene. The strain S449B3 grew also on p-xylene, and S449B6 on p-xylene, toluene, and ethylbenzene.They were all shown to be capable of producing an ultraviolet-absorbing substance from p-cymene. This substance was isolated in crystalline form and identified as cumic acid by infrared absorption spectrum and other observations.The superior strain, S449B6, produced the acid as much as 1000 mg/1 in shaking culture at 30°C after 24 hours. The yields were increased up to approximately 1700 mg/1 after further investigations. Addition of calcium carbonate and considerable agitation were favorable conditions for the acid production.The taxonomical studies of these strains were carried out, and they...
TL;DR: The fungitoxicity of Polyoxins A to G was positively related to their inhibition of 14C-glucosamine incorporation into the cell wall chitin of C. miyabeanus.
Abstract: In the previous papers we reported that the antibiotic Polyoxin D induced the characteristic swelling of the mycelia of fungi,1,2) and strongly inhibited the incorporation of 14C-glucosamine into the fungal cell wall chitin.3) The present work has been conducted to further investigate the influence of this antibiotic on the fungal cell wall biosynthesis.Polyoxin D did not inhibit the incorporation of 14C-glucose, 14C-amino acids and 14C-sodium acetate into the cell wall. In addition, UDP-N-acetylglucosamine, a precurcor of chitin biosynthesis of cell wall, was accumulated in the Polyoxin D-treated mycelia of Cochliobolus miyabeanus more than 150 to 160% of that accumulated in the untreated one.Chitin synthetase prepared from Piricularia oryzae which is not treated with Polyoxin D was completely inhibited by the addition of 0.1 ppm of Polyoxin D. The fungitoxicity of Polyoxins A to G was positively related to their inhibition of 14C-glucosamine incorporation into the cell wall chitin of C. miyabeanus. From...
TL;DR: The inactivation of the enzymes by linoleic acid hydroperoxides (LAHPO) was tested in connection with the toxicity of oxidized fat and may show that the inhibition occurs by binding of suchhydrophobic compounds to the enzyme, and that the surface exposition of hydrophobic region may depend on the pH.
Abstract: The inactivation of the enzymes by linoleic acid hydroperoxides (LAHPO) was tested in connection with the toxicity of oxidized fat. At the same time, the inhibition of enzyme activities by linoleic acid was also tested. Ribonuclease (RNase), trypsin, chymotrypsin and pepsin which are considered to be simple proteins and not to be SH-enzymes were chosen as the enzymes. RNase was largely inhibited by LAHPO, but the other enzymes were inhibited by linoleic acid as well as LAHPO. The inhibition of each enzyme occurred at different pH. This fact may show that the inhibition occurs by binding of such hydrophobic compounds to the enzyme, and that the surface exposition of hydrophobic region may depend on the pH. Not only the reaction of some specific amino acid residue in the protein molecules with LAHPO, but also the binding of these hydrophobic compounds must be remembered in the mechanism of inhibition.
TL;DR: In this article, pyrazines were also found from the pyrolysis of l-threonine, but not from that of alanine and considered to be characteristic pyrolysis products of β-hydroxy amino acids.
Abstract: From the pyrolysis of l-serine, ten volatile compounds including several pyrazines were identified. Pyrazines were also found from the pyrolysis of l-threonine, but not from that of alanine and considered to be characteristic pyrolysis products of β-hydroxy amino acids. At the same time, diketopiperazines, amines and carbonyl compounds were also found in addition to those described above. Formation mechanism of pyrazine compounds was also discussed.
TL;DR: Three isocoumarin compounds (BV 1, 2 and 3) were isolated from the cultural broth of Aspergillus oniki 1784 as mentioned in this paper, and two of them were newly isolated.
Abstract: Three isocoumarin compounds (BV 1, 2 and 3) were isolated from the cultural broth of Aspergillus oniki 1784. BV 1 was mellein (3-methyl-8-hydroxy-3,4-dihydroisocoumarin). BV 2 and 3 were assigned to be 3-methyl-4,8-dihydroxy-3,4-dihydroisocoumarin, 3-methyl-3,8-dihydroxy-3,4-dihydroisocoumarin, respectively. These two compounds (BV 2, 3) were newly isolated. Also another component named BV 4 was proved to be 6-methylsalicylic acid.
TL;DR: In this paper, the ratio of milk clotting to proteolytic activities (MCA/PA) was assumed to be an important index for the selection of organism, and Fomitopsis pinicola and Coriolus consors (Berk.) Imaz. were selected as the strain with high MCA /PA ratio.
Abstract: In the course of screening tests of Basidiomycete proteolytic enzymes, it was observed that some strains produced milk clotting enzymes with fairly weak proteolytic activities.When sucrose-polypeptone and sucrose-corn steep liquor media were used, only 6 strains out of 44 strains tested showed weak milk clotting activities. Cheddar cheese making with culture filtrates of these 6 strains revealed that the culture filtrates of 2 strains, Irpex lacteus Fr. and Fomitopsis pinicola (Fr.) Karst., were able to produce Cheddar cheese of good quality.On the other hand, when sucrose-distillers solubles media were used, a lot of strains showed high proteolytic activity in addition to high milk clotting activity. The ratio of milk clotting to proteolytic activities (MCA/PA) was assumed to be an important index for the selection of organism, and F. pinicola and Coriolus consors (Berk.) Imaz. were selected as the strain with high MCA/PA ratio.As the investigation on culture conditions of 3 strains mentioned above showe...
TL;DR: The fungitoxicity of Polyoxins A to G was positively related to their inhibition of 14C-glucosamine incorporation into the cell wall chitin of C. miyabeanus.
Abstract: In the previous papers we reported that the antibiotic Polyoxin D induced the characteristic swelling of the mycelia of fungi,1,2) and strongly inhibited the incorporation of 14C-glucosamine into the fungal cell wall chitin.3) The present work has been conducted to further investigate the influence of this antibiotic on the fungal cell wall biosynthesis.Polyoxin D did not inhibit the incorporation of 14C-glucose, 14C-amino acids and 14C-sodium acetate into the cell wall. In addition, UDP-N-acetylglucosamine, a precurcor of chitin biosynthesis of cell wall, was accumulated in the Polyoxin D-treated mycelia of Cochliobolus miyabeanus more than 150 to 160% of that accumulated in the untreated one.Chitin synthetase prepared from Piricularia oryzae which is not treated with Polyoxin D was completely inhibited by the addition of 0.1 ppm of Polyoxin D. The fungitoxicity of Polyoxins A to G was positively related to their inhibition of 14C-glucosamine incorporation into the cell wall chitin of C. miyabeanus. From...
TL;DR: In this article, the content of the ovomucin gel obtained from the gel parts of stored thick white decreased during storage and the carbonhydrate contents of the sol parts of the stored (20 days) thick white were higher than those of the control OVOMIN gel (B) obtained from newly laid thick white.
Abstract: The content of the ovomucin gel obtained from the gel parts of stored thick white decreased during storage. Changes of the content of the ovomucin gel (A) was much larger than that of the ovomucin gel (B). The content of the ovomucin sol obtained from the sol parts of stored thick white increased during storage.The hexose and hexosamine contents of the ovomucin gel (B) decreased to about one half and the sialic acid content decreased to one eighth after 20 days storage at 30°C On the other hand, the carbonhydrate contents of the ovomucin sol (B) increased during storage and those obtained from sol parts of the stored (20 days) thick white were higher than those of the control ovomucin gel (B) obtained from the newly laid thick white. The amino acid composition of the ovomucin gel (B) and sol (B) did not show a great deal of change during storage.It is suggested from these results that the properties of the ovomucin gel (B) changed greatly during storage; one portion of the ovomucin gel (B), the carbohydra...