Showing papers by "Mitsuo Miyazawa published in 2000"
TL;DR: A methanol extract from Pogostemon cablin showed a suppressive effect on umu gene expression of SOS response in Salmonella typhimurium TA1535/pSK1002 against the mutagen 2-(2-furyl)-3-(5-nitro-2-Furyl)acrylamide (furylfuramide).
Abstract: A methanol extract from Pogostemon cablin showed a suppressive effect on umu gene expression of SOS response in Salmonella typhimurium TA1535/pSK1002 against the mutagen 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide). The methanol extract was re-extracted with hexane, dichloromethane, butanol, and water. A dichloromethane fraction showed a suppressive effect. Suppressive compounds against furylfuramide in the dichloromethane fraction were isolated by SiO(2) column chromatography and identified as 7,4'-di-O-methyleriodictyol (1), 7, 3',4'-tri-O-methyleriodictyol (2), and 3,7,4'-tri-O-methylkaempferol (3). In addition, three flavonoids, ombuine (4), pachypodol (5), and kumatakenin (6), were isolated and identified from the dichrolomethane fraction. Compounds 1 and 3 suppressed >50% of the SOS-inducing activity at 80% of the SOS-inducing activity of Trp-P-1 at <0.06 micromol/mL, and compounds 1 and 2 suppressed 87 and 63% at a concentration of 0.3 micromol/mL. In addition, these compounds were assayed with activated Trp-P-1, and the suppressed effects of these compounds were further decreased when compared to Trp-P-1. The antimutagenic activities of these compounds against furylfuramide, Trp-P-1, and activated Trp-P-1 were assayed by the Ames test using S. typhimurium TA100.
100 citations
TL;DR: An MeOH extract of Alpinia oxyphylla was found to possess insecticidal activity against larvae of Drosophila melanogaster Meigen, indicating that the carbonyl group at the 2-position in 1 was the important function for enhanced activity of 1.
Abstract: In the course of screening for novel naturally occurring insecticides from Chinese crude drugs, an MeOH extract of Alpinia oxyphylla was found to possess insecticidal activity against larvae of Drosophila melanogaster Meigen. From the extract, an insecticidal compound was isolated by bioassay-guided fractionation and identified as nootkatone (1) by GC, GC-MS, and (1)H and (13)C NMR spectroscopy. In bioassays for insecticidal activity, 1 showed an LC(50) value of 11.5 micromol/mL of diet against larvae of D. melanogaster and an LD(50) value of 96 microg/adult against adults. Epinootkatol (1A), however, showed slight insecticidal activity in both assays, indicating that the carbonyl group at the 2-position in 1 was the important function for enhanced activity of 1.
91 citations
TL;DR: The results showed the α-methylene-γ-lactones inhibited the growth of three bacteria and two fungi and suppressed the SOS-inducing activity of three mutagens, furylfuramide, UV irradiation, and Trp-P-1, respectively.
Abstract: Seven kinds of α-methylene-γ-lactones with an alkyl group at the C-4 position were synthesized according to a previously described method, with yields of 28−34%. These α-methylene-γ-lactones had ch...
24 citations
TL;DR: The (+)-menthol, (+)-pulegone, piperitenone, and cuminaldehyde were shown to have the most potent suppressive effects, and the ID(50) (dose for 50% inhibition) was 0.52 micromol/mL.
Abstract: Suppression of the furylfuramide-induced SOS response by 25 kinds monoterpenoids (hydrocarbons, alcohols, ketones, and aldehydes) with a p-menthane skeleton was studied. Suppression of the SOS-indu...
22 citations
TL;DR: β-Myrcene was mixed in an artificial diet at a concentration of 1 mg/g of diet, and the diet was fed to the last instar larvae of common cutworm, and β-myrcene was transformed mainly to myrcene-3(10)-glycol and myrcenes-1,2-glycol.
Abstract: β-Myrcene was mixed in an artificial diet at a concentration of 1 mg/g of diet, and the diet was fed to the last instar larvae of common cutworm (Spodoptera litura). Metabolites were recovered from frass and analyzed spectroscopically. β-Myrcene was transformed mainly to myrcene-3(10)-glycol and myrcene-1,2-glycol. Each pair of double bonds of β-myrcene was converted to the corresponding diol by oxidation, respectively. The 3,10- and 1,2-double bonds of β-myrcene were respectively oxidized. Keywords: Common cutworm; Spodoptera litura; biotransformation; β-myrcene; myrcene-3(10)-glycol; myrcene-1,2-glycol
21 citations
TL;DR: Gamma-terpinene was mixed in artificial diet at a concentration of 1 mg/g of diet, and the diet was fed to the last instar larvae of common cutworm (Spodoptera litura) as mentioned in this paper.
Abstract: gamma-Terpinene was mixed in artificial diet at a concentration of 1 mg/g of diet, and the diet was fed to the last instar larvae of common cutworm (Spodoptera litura). Metabolites were recovered from frass and analyzed spectroscopically. gamma-Terpinene was transformed mainly to p-mentha-1,4-dien-7-oic acid and p-cymen-7-oic acid (cumic acid). Similarly, (-)-alpha-phellandrene was transformed mainly to (4R)-p-mentha-1,5-dien-7-oic acid and p-cymen-7-oic acid (cumic acid). The C-7 position (allylic methyl group) of gamma-terpinene and (-)-alpha-phellandrene was preferentially oxidized.
15 citations
TL;DR: The biotransformations of 4-methylcyclohexanone and 4-ethylcyclo hexanone were investigated using 10 kinds of anthracnose fungi as biocatalysts and cis-alcohol was formed with stereoselectivity by Glomerella cingulata and C graminicola.
Abstract: The biotransformations of 4-methylcyclohexanone and 4-ethylcyclohexanone were investigated using 10 kinds of anthracnose fungi as biocatalysts. 4-Methylcyclohexanone and 4-ethylcyclohexanone were reduced to the corresponding cis- and trans-alcohols respectively. In the case of 4-methylcyclohexanone, it was transformed to mainly trans-4-methylcyclohexanol by all the fungi examined. In particular, the ratio of cis- and trans-alcohol products was shown to be 1:81 with high stereoselectivity by Colletotrichum lagenarium after a 7-day incubation period. The biotransformation of 4-ethylcyclohexanone by C lagenarium, C dematium MAFF410046, C trifolii MAFF305389, C fragariae, C atramentarium MAFF712102, C lindemuthianum (C-1), C lindemuthianum (C-3) and C lindemuthianum (C-13) produced mainly trans-4-ethylcyclohexanol. On the other hand, cis-alcohol was formed with stereoselectivity by Glomerella cingulata and C graminicola MAFF305460.
© 2000 Society of Chemical Industry
11 citations
TL;DR: Results showed that 2-hydroxy-6-methoxyacetophenone displayed the strongest activity, and a hydroxyl group at C-2 is necessary feature for acetophenone derivatives to show the suppressive effects of furylfuramide-induced SOS response.
Abstract: The recently isolated paeonol (2-hydroxy-4-methoxyacetophenone), as one of the antimutagenic compounds from Discorea japonica, was used as a lead compound for detailed structure−activity relationship studies. Nine acetophenones (2-hydroxy-4-methoxy, 2-hydroxy-5-methoxy, 2-hydroxy-6-methoxy, 4-hydroxy-3-methoxy, o-methoxy, m-methoxy, p-methoxy, and 2,5-dimethoxyacetophenone and acetophenone) were investigated for their ability of suppression of furylfuramide-induced SOS response using Salmonella typhimurium TA1535/pSK1002 in the umu test, against the mutagen, 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide). The results showed that 2-hydroxy-6-methoxyacetophenone displayed the strongest activity (EC50 = 0.6 μmol/mL), and a hydroxyl group at C-2 is necessary feature for acetophenone derivatives to show the suppressive effects of furylfuramide-induced SOS response. Keywords: Acetophenones; suppressive effects; SOS response; umu gene; Salmonella typhimurium TA1535/pSK1002; furylfuramide
9 citations
TL;DR: In this article, the composition of the essential oil from the flowers of Neofinetia falcata has been investigated by capillary GC and GC/MS, which contained 40 components of which 66.2% were terpenoid.
Abstract: The composition of the essential oil from flowers of Neofinetia falcata has been investigated by capillary GC and GC/MS. The oil contained 40 components of which 66.2% were terpenoid. The main constituents were geranyl geraniol (53-0%), heptacosane (5.3%), linalool (4.5%), pentacosane (4.0%), squalene (3.9%), ethyl arachidiate (3–8%) and α-farnesene (3.1%).
5 citations
TL;DR: The microbial transformation of (-)-dihydromyrcenyl acetate was investigated using the plant parasitic fungus Glomerella cingulata and converted to dihydromyr cenol, which was then converted to 3,7- dihydroxy-3, 7-dimethyl-1-octene-7-carboxylate.
Abstract: The microbial transformation of (-)-dihydromyrcenyl acetate was investigated using the plant parasitic fungus Glomerella cingulata. As a result, (-)-dihydromyrcenyl acetate was converted to dihydromyrcenol, 3,7-dihydroxy-3,7-dimethyl-1-octene-7-carboxylate, 3,7-dihydroxy-3,7-dimethyl-1-octene, 3,7-dimethyloctane-1,2,7-triol-7-carboxylate, and 3,7-dimethyloctane-1,2,7-triol. In addition, microbial transformation of dihydromyrcenol by G. cingulata was carried out. The metabolic pathway of (-)-dihydromyrcenyl acetate is discussed.
5 citations
TL;DR: The ratio of cis- and trans-alcohol products was shown to be 1 : 13 (4-propylcyclohexanol) and 1 : 11 ( 4-isopropyl cyclohexanone) with high stereoselectivity by C. lagenarium after a 7-day incubation period.
Abstract: The biotransformation of 4-propylcyclohexanone and 4-isopropylcyclohexanone was examined using ten different anthracnose fungi as biocatalysts. 4-Propylcyclohexanone and 4-isopropylcyclohexanone were reduced to the corresponding cis- and trans-alcohols, respectively, and transformed mainly to trans-4-alcohols by all ten fungi enumerated as follows; Colletotrichum lagenarium, C. dematium MAFF410046, C. trifolii MAFF305389, C. fragariae, C. atramentarium MAFF712102, C. lindemuthianum (C-1), C. lindemuthianum (C-3), C. lindemuthianum (C-13), C. graminicola MAFF305460 and Glomerella cingulata. In particular, the ratio of cis- and trans-alcohol products was shown to be 1 : 13 (4-propylcyclohexanol) and 1 : 11 (4-isopropylcyclohexanol) with high stereoselectivity by C. lagenarium after a 7-day incubation period.
01 Jan 2000
TL;DR: This chapter demonstrates the biotransformation of terpenoids, attempted by the larvae of common cutworm (Spodoptera liturd), and indicates that the intestinal bacteria probably participate in the metabolism of a-terpinene.
Abstract: Publisher Summary Biotransformation is a useful way to produce biologically active terpenoids. This chapter explores the biotransformation of terpenoids in mammals and by microorganisms, and demonstrates the biotransformation of terpenoids, attempted by the larvae of common cutworm (Spodoptera liturd). The reasons for using the larvae of S. litura as a biological catalyst are: Lepidopteran larvae feed on plants containing terpenoids as their diet and therefore possess a high level of enzymatic activity against terpenoids; the worm consumes a large amount of plants, making it possible to obtain more metabolites; and the worm is easy to rear on a laboratory scale. α-Terpinene is mixed in an artificial diet at a concentration of 10 mg/g of diet, and the diet is fed to the last instar larvae of common cutworm (Spodoptera litura). Metabolites are recovered from frass and analyzed spectroscopically. The α-terpinene is transformed mainly to 4-isopropyl-l,3-cyclohexadienoic acid and cumic acid. Similarly, (+)-limonene is transformed mainly to (+)- ρ -menth-l-ene-8,9-diol (uroterpenol) and (+)- ρ -mentiia-l,8-dien-7-oic acid (perillic acid), (-)-limonene is transformed mainly to (-)- ρ -menth-l-ene-8,9-diol (uroterpenol) and (-)- /7-mentha-l,8-dien-7-oic acid (perillic acid). On the other hand, γ-terpinene is transformed mainly to ρ -mentha-l,4-dien-7-oic acid and ρ -cymen-7-oic acid (cumic acid) by the same way. The results indicate that the intestinal bacteria probably participate in the metabolism of a-terpinene. The aerobically active intestinal bacteria transform α-terpinene to 4-isopropyl-l,3-cyclohexadienemethanol, and the anaerobically active intestinal bacteria transformed a-terpinene to ρ -cymene.