The Experts below are selected from a list of 291 Experts worldwide ranked by ideXlab platform
Mitsuo Miyazawa - One of the best experts on this subject based on the ideXlab platform.
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Biological stereoselective reduction of 3,3,5-trimethylcyclohexanone by Glomerella cingulata.
Natural Product Letters, 2020Co-Authors: Shigeaki Okamura, Hiromu Kameoka, Mitsuo MiyazawaAbstract:Abstract The microbial transformation of 3,3,5-trimethylcyclohexanone was investigated using the plant pathogenic fungus, Glomerella cingulata. With this organism 3,3,5-trimethylcyclohexanone gave the corresponding cis- and trans-3,3,5-trimethylcyclohexanols with the ratio of 20 : 1 forming the cis-isomer highly stereoselectively, upon 5 days incubation together with 3,3,5-trimethyl-2-cyclohexen- 1-one (isophrone) as a minor product.
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Biotransformation of (+)- and (-)-bornyl acetate using the plant parasitic fungus Glomerella cingulata as a biocatalyst
Journal of Chemical Technology & Biotechnology, 2020Co-Authors: Mitsuo Miyazawa, Yoshiki MiyasatoAbstract:The microbial transformations of (+)- and (-)-bornyl acetate were investigated using the plant parasitic fungus, Glomerella cingulata. As a result, (+)- and (-)-bornyl acetate were converted to (+)- and (-)-5-exo-hydroxybornyl acetate, (+)- and (-)-5-oxobornyl acetate and (+)- and (-)-borneol respectively. The structures of the metabolic products were determined by spectroscopic data.
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stereoselective biocatalytic reduction of α ionone by Glomerella cingulata
Journal of Molecular Catalysis B-enzymatic, 2012Co-Authors: Mitsuo Miyazawa, Kazuya ShimizuAbstract:Abstract The biotransformation of (±)-α-ionone ( 1 ) by Glomerella cingulata was investigated. Compound 1 was transformed into two compounds ( 2 , 3 ). The ketone was reduced to α-ionol and the olefin was reduced to dihydrio-α-ionol, respectively. (−)-(6 S ,9 R )- and (+)-(6 R ,9 S )-α-ionol proceeded the corresponding allylic alcohols in high enantiomeric excess >99%; (−)-( S )-α-ionone is preferentially metabolized by hydroxylation in the ketone at C-9. Especially on the metabolic pathway, olefine reduction was via after ketone reduction.
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microbial transformation of isopimpinellin by Glomerella cingulata
Journal of Oleo Science, 2011Co-Authors: Shinsuke Marumoto, Mitsuo MiyazawaAbstract:: Microbial transformation studies conducted on isopimpinellin (1) by the fungus Glomerella cingulata have revealed that 1 was metabolized to give the corresponding reduced acid, 5,8-dimethoxy-6,7-furano-hydrocoumaric acid (2). The structure of metabolite 2 was elucidated by high-resolution mass spectrometry (HR-MS), extensive NMR techniques, including (1)H NMR, (13)C NMR, (1)H-(1)H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteonuclear multiple bond coherence (HMBC). The biotransformed product 2 showed weak a in vitro β-secretase (BACE1) inhibitory effect.
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biotransformation of bergapten and xanthotoxin by Glomerella cingulata
Journal of Agricultural and Food Chemistry, 2010Co-Authors: Shinsuke Marumoto, Mitsuo MiyazawaAbstract:The biotransformation of bergapten (1) by the fungus Glomerella cingulata gave the corresponding reduced acid, 6,7-furano-5-methoxy hydrocoumaric acid (2), a new compound. Xanthotoxin (3) was also converted to the corresponding reduced acid cnidiol b (4) and demethylated metabolite xanthotoxol (5) by G. cingulata. The structure of the new compound 2 was elucidated by high-resolution mass spectrometry, extensive NMR techniques, including 1H NMR and 13C NMR, 1H−1H correlation spectroscopy, heteronuclear multiple quantum coherence, and heteonuclear multiple bond coherence. The methyl ester or methyl ether or methyl ester and ether derivatives of 2 and 4 were synthesized. All compounds were tested for the β-secretase (BACE1) inhibitory activity in vitro. The methyl ester and ether derivative 8 was shown to possess BACE1 inhibitory activity, and a IC50 value was 0.64 ± 0.04 mM.
Hiromu Kameoka - One of the best experts on this subject based on the ideXlab platform.
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Biological stereoselective reduction of 3,3,5-trimethylcyclohexanone by Glomerella cingulata.
Natural Product Letters, 2020Co-Authors: Shigeaki Okamura, Hiromu Kameoka, Mitsuo MiyazawaAbstract:Abstract The microbial transformation of 3,3,5-trimethylcyclohexanone was investigated using the plant pathogenic fungus, Glomerella cingulata. With this organism 3,3,5-trimethylcyclohexanone gave the corresponding cis- and trans-3,3,5-trimethylcyclohexanols with the ratio of 20 : 1 forming the cis-isomer highly stereoselectively, upon 5 days incubation together with 3,3,5-trimethyl-2-cyclohexen- 1-one (isophrone) as a minor product.
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Biotransformation of the sesquiterpenoid (+)-γ-Gurjunene using a plant pathogenic fungus, Glomerella cingulata, as a biocatalyst
Phytochemistry, 1998Co-Authors: Mitsuo Miyazawa, Yoshihiro Honjo, Hiromu KameokaAbstract:Abstract The biotransformation of a sesquitepenod which possesses a guaiane skeleton, (+)- γ -gurjunene has been investigated using the plant pathogenic fungus, Glomerella cingulata as a biocatalyst. (+)- γ -Gurjunene was oxidized at the double bond of the isopropenyl group to (1 S ,4 S ,7 R ,10 R )-5-guaien-11,13-diol and in addition oxidized at the C–10 position to (1 S ,4 S ,7 R ,10 S )-5-guaien-10,11,13-triol. The structures of the metabolic products have been elucidated on the basis of their spectral data.
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biotransformation of the sesquiterpenoid γ gurjunene using a plant pathogenic fungus Glomerella cingulata as a biocatalyst
Phytochemistry, 1998Co-Authors: Mitsuo Miyazawa, Yoshihiro Honjo, Hiromu KameokaAbstract:Abstract The biotransformation of a sesquitepenod which possesses a guaiane skeleton, (+)- γ -gurjunene has been investigated using the plant pathogenic fungus, Glomerella cingulata as a biocatalyst. (+)- γ -Gurjunene was oxidized at the double bond of the isopropenyl group to (1 S ,4 S ,7 R ,10 R )-5-guaien-11,13-diol and in addition oxidized at the C–10 position to (1 S ,4 S ,7 R ,10 S )-5-guaien-10,11,13-triol. The structures of the metabolic products have been elucidated on the basis of their spectral data.
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biotransformation of lavandulol by the plant pathogenic fungus Glomerella cingulata
Journal of Agricultural and Food Chemistry, 1998Co-Authors: Hirokazu Nankai, Mitsuo Miyazawa, Shinichi Akazawa, Hiromu KameokaAbstract:To clarify the structures of biotransformation products and the metabolic pathways, the microbial transformation of (±)-lavandulol has been investigated using the plant pathogenic fungus Glomerella cingulata. (±)-Lavandulol [(±)-5-methyl-2-(1-methylethenyl)-4-hexen-1-ol] was mainly oxidized at the C-4 double bond to give (−)-(2S,4S)-1,5-epoxy-5-methyl-2-(1-methylethenyl)-4-hexanol and cis- and trans-1,4-epoxy-5-methyl-2-(1-methylethenyl)-5-hexanol. 5-Methyl-2-(1-methylethenyl)-4-hexene-1,6-diol (6-hydroxylavandulol) was also produced through this biotransformation. These structures were confirmed by the mass, IR, 1H NMR, and 13C NMR spectral data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-lavandulol; tetrahydropyran; tetrahydrofuran
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Biotransformation of (±)-Lavandulol by the Plant Pathogenic Fungus Glomerella cingulata
Journal of Agricultural and Food Chemistry, 1998Co-Authors: Hirokazu Nankai, Mitsuo Miyazawa, Shinichi Akazawa, Hiromu KameokaAbstract:To clarify the structures of biotransformation products and the metabolic pathways, the microbial transformation of (±)-lavandulol has been investigated using the plant pathogenic fungus Glomerella cingulata. (±)-Lavandulol [(±)-5-methyl-2-(1-methylethenyl)-4-hexen-1-ol] was mainly oxidized at the C-4 double bond to give (−)-(2S,4S)-1,5-epoxy-5-methyl-2-(1-methylethenyl)-4-hexanol and cis- and trans-1,4-epoxy-5-methyl-2-(1-methylethenyl)-5-hexanol. 5-Methyl-2-(1-methylethenyl)-4-hexene-1,6-diol (6-hydroxylavandulol) was also produced through this biotransformation. These structures were confirmed by the mass, IR, 1H NMR, and 13C NMR spectral data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-lavandulol; tetrahydropyran; tetrahydrofuran
Hirokazu Nankai - One of the best experts on this subject based on the ideXlab platform.
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biotransformation of dihydromyrcenyl acetate using the plant parasitic fungus Glomerella cingulata as a biocatalyst
Journal of Agricultural and Food Chemistry, 2000Co-Authors: Mitsuo Miyazawa, Shinichi Akazawa, Hiromu Sakai, Hirokazu NankaiAbstract: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.
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biotransformation of lavandulol by the plant pathogenic fungus Glomerella cingulata
Journal of Agricultural and Food Chemistry, 1998Co-Authors: Hirokazu Nankai, Mitsuo Miyazawa, Shinichi Akazawa, Hiromu KameokaAbstract:To clarify the structures of biotransformation products and the metabolic pathways, the microbial transformation of (±)-lavandulol has been investigated using the plant pathogenic fungus Glomerella cingulata. (±)-Lavandulol [(±)-5-methyl-2-(1-methylethenyl)-4-hexen-1-ol] was mainly oxidized at the C-4 double bond to give (−)-(2S,4S)-1,5-epoxy-5-methyl-2-(1-methylethenyl)-4-hexanol and cis- and trans-1,4-epoxy-5-methyl-2-(1-methylethenyl)-5-hexanol. 5-Methyl-2-(1-methylethenyl)-4-hexene-1,6-diol (6-hydroxylavandulol) was also produced through this biotransformation. These structures were confirmed by the mass, IR, 1H NMR, and 13C NMR spectral data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-lavandulol; tetrahydropyran; tetrahydrofuran
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Biotransformation of (±)-Lavandulol by the Plant Pathogenic Fungus Glomerella cingulata
Journal of Agricultural and Food Chemistry, 1998Co-Authors: Hirokazu Nankai, Mitsuo Miyazawa, Shinichi Akazawa, Hiromu KameokaAbstract:To clarify the structures of biotransformation products and the metabolic pathways, the microbial transformation of (±)-lavandulol has been investigated using the plant pathogenic fungus Glomerella cingulata. (±)-Lavandulol [(±)-5-methyl-2-(1-methylethenyl)-4-hexen-1-ol] was mainly oxidized at the C-4 double bond to give (−)-(2S,4S)-1,5-epoxy-5-methyl-2-(1-methylethenyl)-4-hexanol and cis- and trans-1,4-epoxy-5-methyl-2-(1-methylethenyl)-5-hexanol. 5-Methyl-2-(1-methylethenyl)-4-hexene-1,6-diol (6-hydroxylavandulol) was also produced through this biotransformation. These structures were confirmed by the mass, IR, 1H NMR, and 13C NMR spectral data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-lavandulol; tetrahydropyran; tetrahydrofuran
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Biotransformation of (2Z,6Z)-farnesol by the plant pathogenic fungus Glomerella cingulata
Phytochemistry, 1998Co-Authors: Hirokazu Nankai, Mitsuo Miyazawa, Hiromu KameokaAbstract:Abstract The microbial transformation of (2 Z ,6 Z )-farnesol was investigated using the plant pathogenic fungus, Glomerella cingulata as a biocatalyst. Oxidation of the remote double bond and isomerization of the 2,3-double bond gave (2 Z ,6 Z )-3,7,11-trimethyl-2,6-dodecadiene-1,10,11-triol and (2 E ,6 Z )-3,7,11-trimethyl-2-6-dodecadiene-1,10,11-triol as major metabolites. One of the further degraded compounds, ( Z )-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one, was also obtained.
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Hydroxylation of Two Saturated Acyclic Monoterpenoids, Tetrahydrogeraniol and Tetrahydrolavandulol, by the Plant Pathogenic Fungus Glomerella cingulata
Journal of Natural Products, 1997Co-Authors: Hirokazu Nankai, Mitsuo Miyazawa, Hiromu KameokaAbstract:The microbial transformations by Glomerella cingulata of two saturated acyclic monoterpenoids, tetrahydrogeraniol (1) and tetrahydrolavandulol (3), were investigated. Both compounds were hydroxylated regioselectively at the isopropyl group. Tetrahydrogeraniol was transformed to hydroxycitronellol (2), while tetrahydrolavandulol was transformed to 5-hydroxytetrahydrolavandulol (4). This is the first report describing the microbial transformation of compounds 1 and 3.
Yoshiki Miyasato - One of the best experts on this subject based on the ideXlab platform.
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Biotransformation of (+)- and (-)-bornyl acetate using the plant parasitic fungus Glomerella cingulata as a biocatalyst
Journal of Chemical Technology & Biotechnology, 2020Co-Authors: Mitsuo Miyazawa, Yoshiki MiyasatoAbstract:The microbial transformations of (+)- and (-)-bornyl acetate were investigated using the plant parasitic fungus, Glomerella cingulata. As a result, (+)- and (-)-bornyl acetate were converted to (+)- and (-)-5-exo-hydroxybornyl acetate, (+)- and (-)-5-oxobornyl acetate and (+)- and (-)-borneol respectively. The structures of the metabolic products were determined by spectroscopic data.
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biotransformation of and bornyl acetate using the plant parasitic fungus Glomerella cingulata as a biocatalyst
Journal of Chemical Technology & Biotechnology, 2001Co-Authors: Mitsuo Miyazawa, Yoshiki MiyasatoAbstract:The microbial transformations of (+)- and (-)-bornyl acetate were investigated using the plant parasitic fungus, Glomerella cingulata. As a result, (+)- and (-)-bornyl acetate were converted to (+)- and (-)-5-exo-hydroxybornyl acetate, (+)- and (-)-5-oxobornyl acetate and (+)- and (-)-borneol respectively. The structures of the metabolic products were determined by spectroscopic data.
Yoshihiro Honjo - One of the best experts on this subject based on the ideXlab platform.
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Biotransformation of the sesquiterpenoid (+)-γ-Gurjunene using a plant pathogenic fungus, Glomerella cingulata, as a biocatalyst
Phytochemistry, 1998Co-Authors: Mitsuo Miyazawa, Yoshihiro Honjo, Hiromu KameokaAbstract:Abstract The biotransformation of a sesquitepenod which possesses a guaiane skeleton, (+)- γ -gurjunene has been investigated using the plant pathogenic fungus, Glomerella cingulata as a biocatalyst. (+)- γ -Gurjunene was oxidized at the double bond of the isopropenyl group to (1 S ,4 S ,7 R ,10 R )-5-guaien-11,13-diol and in addition oxidized at the C–10 position to (1 S ,4 S ,7 R ,10 S )-5-guaien-10,11,13-triol. The structures of the metabolic products have been elucidated on the basis of their spectral data.
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biotransformation of the sesquiterpenoid γ gurjunene using a plant pathogenic fungus Glomerella cingulata as a biocatalyst
Phytochemistry, 1998Co-Authors: Mitsuo Miyazawa, Yoshihiro Honjo, Hiromu KameokaAbstract:Abstract The biotransformation of a sesquitepenod which possesses a guaiane skeleton, (+)- γ -gurjunene has been investigated using the plant pathogenic fungus, Glomerella cingulata as a biocatalyst. (+)- γ -Gurjunene was oxidized at the double bond of the isopropenyl group to (1 S ,4 S ,7 R ,10 R )-5-guaien-11,13-diol and in addition oxidized at the C–10 position to (1 S ,4 S ,7 R ,10 S )-5-guaien-10,11,13-triol. The structures of the metabolic products have been elucidated on the basis of their spectral data.
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biotransformation of the sesquiterpenoid β selinene using the plant pathogenic fungus Glomerella cingulata as a biocatalyst
Phytochemistry, 1997Co-Authors: Mitsuo Miyazawa, Yoshihiro Honjo, Hiromu KameokaAbstract:Abstract The biotransformation of β-selinene was investigated using the plant pathogenic fungus Glomerella cingulata as a biocatalyst. β-Selinene was oxidized at the double bond of the isopropenyl group and at the C-1 position regioselectively to (1 S ,6 S ,9 S ,10 R ,11 RS )-1,11,13-trihydroxy- β -selinene. The structures of the metabolic products have been elucidated on the basis of their spectral data.
