ABSTRACT
Biotransformation of bromosesquiterpenes was investigated with two types of fungi, Rhinocladiella atrovirens NRBC 32362 and also Rhinocladiella sp. K-001, isolated from the Okinawan brown alga Stypopodium zonale. R. atrovirens NRBC 32362 converted aplysistatin 1 into three compounds 5alpha-hydroxyaplysistatin 4, 5alpha-hydroxyisoaplysistatin 5 and 9beta-hydroxyaplysistatin 6. Transformation of 1, palisadin A 2 and 12-hydroxypalisadin B 3 by Rhinocladiella sp. K-001 gave two compounds, 3,4-dihydroaplysistatin 7 and 9,10-dehydrobromopalisadin A 8.
Subject(s)
Bromine Compounds/metabolism , Fungi/metabolism , Laurencia/chemistry , Plant Extracts/metabolism , Sesquiterpenes/metabolism , Biotransformation , Fungi/isolation & purification , Phaeophyceae/microbiologyABSTRACT
Suspension cultured cells of Caragana chamlagu (Leguminosae) converted zerumbone (1) into zerumbone epoxide (2) as the intermediate, (2R,3R,7R)-2,3-epoxy-9-humulen-8-one (3) and (2R,3S,7R)-2,3-epoxy-9-humulen-8-one (4) as new sesquiterpenes in 11%, 36% and 21% yields, respectively.
Subject(s)
Caragana/metabolism , Sesquiterpenes/metabolism , Biotransformation , Caragana/cytology , Mass Spectrometry , Molecular Structure , Sesquiterpenes/chemistryABSTRACT
The biotransformation of 2-methylcyclohexanone (1) using 16 fungal strains and some mushroom cultures was investigated. Fusarium sp. was one of the effective biocatalysts for oxidoreduction of 2-methylcyclohexanone (1). cis-2-Methylcyclohexanol (2a) was isomerized to trans-2-methylcyclohexanol (2b) by Fusarium sp. In addition, the corresponding lactones 3 was obtained by Baeyer-Villiger oxidation using Fusarium sp. AP-2 (46%, 94% ee).
Subject(s)
Cyclohexanones/metabolism , Fusarium/metabolism , Biotransformation , Catalysis , Cyclohexanones/chemistry , Oxidation-Reduction , Time FactorsABSTRACT
The biotransformation of racemic 1-phenylethanol (30 mg) with plant cultured cells of basil (Ocimum basilicum cv. Purpurascens, 5 g wet wt) by shaking 120 rpm at 25 degrees C for 7 days in the dark gave (R)-(+)-1-phenylethanol and acetophenone in 34 and 24% yields, respectively. The biotransformation can be applied to other 1-arylethanols and basil cells oxidized the (S)-alcohols to the corresponding ketones remaining the (R)-alcohols in excellent ee.
Subject(s)
Acetophenones/metabolism , Ocimum basilicum/metabolism , Phenylethyl Alcohol/metabolism , Biotransformation , Cells, Cultured , Chromatography, Gas , Oxidation-Reduction , StereoisomerismABSTRACT
Some difficulties on a sampling of gaseous glyoxal using DNPH-silica cartridge were discussed, and an alternative sampling procedure was proposed. When glyoxal was sampled using the cartridge, it partially formed mono-hydrazone with various degrees, whereas it was quantitatively converted into its bis-hydrazone when sample gas was directly bubbled into a DNPH acidic solution. Additionally, glyoxal polymerized on the inner wall of the system during trapping to the silica cartridge. We found that the polymerization of glyoxal was effectively suppressed by dissolving glyoxal into methanol under reduced pressure; glyoxal in methanol readily reacted with DNPH in a hydrochloric acid solution and gave bis-hydrazone derivative, without any interference of methanol and any formation of mono-hydrazone derivative. When glyoxal was sampled by the proposed method, 102% of recovery was obtained, whereas it was reduced to 92.7% when the trapped glyoxal was dissolved into methanol under atmosphere.
Subject(s)
Chromatography, High Pressure Liquid/methods , Glyoxal/chemistry , Hydrazones/analysis , Methanol/chemistry , Polymers/chemistry , Spectrophotometry, UltravioletABSTRACT
The biologic degradation of 2,2-bis(4-hydroxyphenyl)propane (bisphenol A [BPA]; 1) was studied with 26 fungi. An initial BPA concentration of 40 ppm in an aqueous solution was degraded in the dark for 14 d. Among the 26 strains tested, 11 degraded BPA at 50% or more. Furthermore, four strains (F. sporotrichioides NFRI-1012, F. moniliforme 2-2, A. terreus MT-13, and E. nidulans MT-98) were more effective for degradation of BPA.
Subject(s)
Fungi/metabolism , Phenols/metabolism , Spores, Fungal/metabolism , Benzhydryl Compounds , Biodegradation, Environmental , Darkness , Gas Chromatography-Mass Spectrometry , Models, Chemical , Oxygen/chemistry , Species Specificity , Time FactorsABSTRACT
The biological degradation of 2,2-bis(4-hydroxyphenol)propane (1; bisphenol A, BPA), a representative endocrine disruptor, was studied with plant-cultured cells of Caragana chamlagu. An initial BPA concentration of 425 microM in an aqueous solution was degraded by C. chamlagu at 25 degrees C for 2 days in the dark, and two intermediates were then completely dissipated after 10 days.
Subject(s)
Caragana/metabolism , Phenols/metabolism , Benzhydryl Compounds , Biodegradation, Environmental , Caragana/cytology , Cells, Cultured , Gas Chromatography-Mass SpectrometryABSTRACT
Biotransformation of 3,6-dialkylcyclohexane-1,2-diones by cell suspension cultures of Marchantia polymorpha involves regioselective oxidative cleavage of the C-C bond to give the corresponding oxocarboxylic acids shortened by one carbon unit. In the case of cyclohexane-1,2-dione, adipic acid was obtained.
