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Hiromu Kameoka - 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: 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, 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, 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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biotransformation of the sesquiterpenoid β selinene using the plant Pathogenic Fungus glomerella cingulata as a biocatalyst
Phytochemistry, 1997Co-Authors: 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.
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biotransformation of acyclic terpenoid 2e 6e farnesol by plant Pathogenic Fungus glomerella cingulata
Phytochemistry, 1996Co-Authors: Hirokazu Nankai, Hiromu KameokaAbstract:The microbial transformation of (2E,6E)-farnesol was investigated using the plant Pathogenic Fungus, Glomerella cingulata. At the first step, oxidation proceeded at the remote double bond to give (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,11-diol and (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,10,11-triol. In the second step, (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,11-diol was hydroxylated at the C-5 position and to give (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol. In addition, (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol was isomerized to (2Z,6E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol.
Hirokazu Nankai - One of the best experts on this subject based on the ideXlab platform.
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biotransformation of lavandulol by the plant Pathogenic Fungus glomerella cingulata
Journal of Agricultural and Food Chemistry, 1998Co-Authors: Hirokazu Nankai, 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, 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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biotransformation of acyclic terpenoid 2e 6e farnesol by plant Pathogenic Fungus glomerella cingulata
Phytochemistry, 1996Co-Authors: Hirokazu Nankai, Hiromu KameokaAbstract:The microbial transformation of (2E,6E)-farnesol was investigated using the plant Pathogenic Fungus, Glomerella cingulata. At the first step, oxidation proceeded at the remote double bond to give (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,11-diol and (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,10,11-triol. In the second step, (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,11-diol was hydroxylated at the C-5 position and to give (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol. In addition, (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol was isomerized to (2Z,6E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol.
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biotransformations of acyclic terpenoids cis nerolidol and nerylacetone by plant Pathogenic Fungus glomerella cingulata
Phytochemistry, 1995Co-Authors: Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-cis-nerolidol and nerylacetone were investigated using the plant Pathogenic Fungus, Glomerella cingulata. Both (±)-cis-nerolidol and nerylacetone were mainly oxidized at the remote double bond. (±)-cis-Nerolidol was transformed into (Z)-3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol while nerylacetone was transformed into (Z)-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. In addition, the biotransformation of nerylacetone resulted in hydration at the remote double bond and reduction of the carbonyl group and produced (Z)-6,10-dimethyl-5,9-undecadien-2-ol, (Z)-10-hydroxy-6,10-dimethyl-5-undecen-2-one and (Z)-6,10-dimethyl-5-undecen-2,9,10-triol. The structures of the metabolic products were determined by spectroscopic data.
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biotransformation of cedrol by plant Pathogenic Fungus glomerella cingulata
Phytochemistry, 1995Co-Authors: Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformation of (+)-cedrol has been investigated by using plant Pathogenic Fungus, Glomerella cingulata. (+)-Cedrol was hydroxylated at the C-3 position, and transformed mainly to 3α-hydroxycedrol and with a smaller amount of 3β-hydroxycedrol. 3α-Hydroxycedrol was further transformed to 8-cedren-3α-ol by dehydration at the C-8 position. In addition, G. cingulata produced a small amount of 12-hydroxycedrol from (+)-cedrol with stereoselective hydroxylation of the methyl group at the C-12 position. The structures of the metabolic products were determined by their spectroscopic data.
Tariq M. Butt - One of the best experts on this subject based on the ideXlab platform.
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conidia of the insect Pathogenic Fungus metarhizium anisopliae fail to adhere to mosquito larval cuticle
Royal Society Open Science, 2014Co-Authors: Bethany P J Greenfield, Alex M Lord, Edward G Dudley, Tariq M. ButtAbstract:Adhesion of conidia of the insect Pathogenic Fungus, Metarhizium anisopliae, to the arthropod host cuticle initially involves hydrophobic forces followed by consolidation facilitated by the action ...
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nutrition influences growth and virulence of the insect Pathogenic Fungus metarhizium anisopliae
Fems Microbiology Letters, 2005Co-Authors: Farooq A Shah, Cheng S Wang, Tariq M. ButtAbstract:Abstract Nutrition influenced growth, sporulation and virulence of the insect Pathogenic Fungus, Metarhizium anisopliae . Virulent conidia were produced on susceptible insect hosts, 1% yeast extract, 2% peptone, osmotic stress medium (OSM) and CN 10:1 medium. Several strain independent markers were identified that could be used to predict the virulence of M. anisopliae conidia. Virulent conidia typically had high levels of spore bound Pr1, an important cuticle degrading protease, and high germination rates. We also show for the first time that virulent conidia have an endogenous CN ratio below 5.2:1. Real Time PCR revealed that virulent conidia from insects contained significantly higher levels of transcripts of pr1 A and other Pathogenicity-related genes than inoculum from artificial media. Of the artificial media studied, 1% yeast extract medium yielded the most virulent conidia, these had higher levels of transcripts of these Pathogenicity-related genes than the least virulent conidia from the high conidia yielding CN 35:1 medium (=SDA), however, the levels were significantly lower than those in insect-derived conidia. Our study shows for the first time that the passaged inoculum is virulent irrespective of the original culture medium or insect host. Virulent conidia were consistently produced on OSM even though growth and sporulation were poor. We postulate that starvation conditions, whether in vivo or in vitro, results in de-repression of Pr1 and that elevated levels of this enzyme enhance fungal virulence.
Masahiko Isaka - One of the best experts on this subject based on the ideXlab platform.
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Cordybislactone, a stereoisomer of the 14-membered bislactone clonostachydiol, from the hopper Pathogenic Fungus Cordyceps sp. BCC 49294: revision of the absolute configuration of clonostachydiol
The Journal of Antibiotics, 2018Co-Authors: Ken-ichi Ojima, Kanoksri Tasanathai, Pattiyaa Laksanacharoen, Arunrat Yangchum, Donnaya Thanakitpipattana, Hidetoshi Tokuyama, Masahiko IsakaAbstract:Cordybislactone ( 3 ), a new stereoisomer of the 14-membered bislactone clonostachydiol, together with its open ring analog ( 4 ), was isolated from the hopper Pathogenic Fungus Cordyceps sp. BCC 49294. The relative and absolute configurations of 3 were determined by chemical derivatizations, including the modified Mosher’s method. The stereochemistry of clonostachydiol was determined using the natural compound isolated from Xylaria sp. BCC 4297. The result revealed that the absolute configuration of clonostachydiol, previously determined by synthesis, should be revised to its enantiomer.
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isariotins g j from cultures of the lepidoptera Pathogenic Fungus isaria tenuipes
Phytochemistry Letters, 2011Co-Authors: Taridaporn Bunyapaiboonsri, Wilunda Choowong, Kanoksri Tasanathai, Nigel L Hyweljones, Janet Jennifer Luangsaard, Urarat Srisanoh, Seangaroon Yoiprommarat, Masahiko IsakaAbstract:Four new alkaloids isariotins G–J (1–4), together with the known isariotins, were isolated from cultures of the Lepidoptera Pathogenic Fungus Isaria tenuipes. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. Compounds 1–4 exhibited antimalarial and cytotoxic activities.
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bioactive compounds from the scale insect Pathogenic Fungus conoideocrella tenuis bcc 18627
Journal of Natural Products, 2011Co-Authors: Masahiko Isaka, Somporn Palasarn, Sumalee Supothina, Somjit Komwijit, Jennifer J LuangsaardAbstract:A new cyclohexadepsipeptide, conoideocrellide A (1), its linear derivatives, conoideocrellides B-D (2-4), three new hopane triterpenoids (5-7), two new bioxanthracenes (9 and 10), and a new isocoumarin glycoside (13) were isolated from the scale insect Pathogenic Fungus Conoideocrella tenuis BCC 18627. Biological activities of the new compounds were evaluated.
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isariotins a d alkaloids from the insect Pathogenic Fungus isaria tenuipes bcc 7831
Journal of Natural Products, 2007Co-Authors: Rachada Haritakun, Punsa Khoyaiklang, Prasert Srikitikulchai, Masahiko IsakaAbstract:Isariotins A–D (1–4), alkaloids possessing a unique bicyclo[3.3.1]nonane ring, were isolated from the insect Pathogenic Fungus Isaria tenuipes BCC 7831. The structures of these compounds were elucidated primarily by NMR and mass spectroscopic analyses.
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hirsutellones a e antimycobacterial alkaloids from the insect Pathogenic Fungus hirsutella nivea bcc 2594
Tetrahedron, 2005Co-Authors: Masahiko Isaka, Yodhathai Thebtaranonth, Nuntawan Rugseree, Pacharee Maithip, Palangpon Kongsaeree, Samran PrabpaiAbstract:Abstract Five new alkaloids, hirsutellones A–E, were isolated from the insect Pathogenic Fungus Hirsutella nivea BCC 2594. Their structures were elucidated by spectroscopic analysis and X-ray crystallography. Hirsutellones displayed significant growth inhibitory activity against Mycobacterium tuberculosis H37Ra.
John W Taylor - One of the best experts on this subject based on the ideXlab platform.
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cryptic speciation in the cosmopolitan and clonal human Pathogenic Fungus aspergillus fumigatus
Evolution, 2005Co-Authors: Anne Pringle, Jean-paul Latgé, D M Baker, Jamie L Platt, John P Wares, John W TaylorAbstract:Microbes and other organisms smaller than one to a few millimeters in size are hypothesized to have global populations, in contrast to the geographically restricted ranges of larger organisms. However, fungi, which routinely have reproductive propagules no larger than 10 micrometers, challenge the generality of this hypothesis because recent studies have shown that globally distributed morphological species embrace two or more geographically restricted phylogenetic species. We used the concordance of gene genealogies to recognize phylogenetic species in the globally distributed opportunistic human Pathogenic Fungus, Aspergillus fumigatus. Based on DNA sequence data of five loci for each of 63 individuals collected from five continents, we have delineated two phylogenetic species in this single morphological species. Unlike all other fungi examined to date, both genetically isolated groups showed a global distribution with no evidence of a correlation between genotype and geographic location. Sexual reproduction has never been observed in A. fumigatus, but when the same data were used to explore the association of alleles at the five loci for one of the phylogenetic species, evidence was found to support recombination. The discovery of a cryptic species is medically relevant because different species are likely to differ in virulence or drug resistance. The discovery of a globally distributed A. fumigatus species clade highlights the need for ecological studies of the Fungus to either document global dispersal or propose alternative mechanisms by which it persists as single, global phylogenetic population.
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phylogeny and pcr identification of the human Pathogenic Fungus penicillium marneffei
Journal of Clinical Microbiology, 1995Co-Authors: Katherine F Lobuglio, John W TaylorAbstract:The phylogenetic position of the human Pathogenic Fungus Penicillium marneffei was assessed from the nucleotide sequences of the nuclear and mitochondrial ribosomal DNA regions. Phylogenetic analysis determined that P. marneffei is closely related to species of Penicillium subgenus Biverticillium and sexual Talaromyces species with asexual biverticillate Penicillium states. Knowledge of the phylogenetic position of P. marneffei facilitated the design of unique oligonucleotide primers, from the nuclear ribosomal DNA internal transcribed spacer region, for the specific amplification of P. marneffei DNA. These primers were successful at selectively amplifying DNA from six isolates of P. marneffei and excluding the other species tested, which included Penicillium subgenus Biverticillium and Talaromyces species and several well-known fungal pathogens, namely, Aspergillus fumigatus, Coccidioides immitis, Histoplasma capsulatum, and Pneumocystis carinii. The primers that we have developed for the specific amplification of P. marneffei have the potential to be incorporated in a PCR identification system which could be used for the identification of this Pathogenic agent from clinical material.
