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1.
《Bioscience, biotechnology, and biochemistry》2013,77(10):2716-2722
The in vitro reactivities of astaxanthin toward peroxynitrite were investigated and the reaction products after scavenging with peroxynitrite were analyzed in order to determine the complete mechanism of this reaction. A series of carotenoids, 13-apo-astaxanthinone (1), 12′-apo-15′-nitroastaxanthinal (2), 12′-apo-astaxanthinal (3), 10′-apo-astaxanthinal (4), 9-cis-14′-s-cis-15′-nitroastaxanthin (5), 14′-s-cis-15′-nitroastaxanthin (6), 13-cis-14′-s-cis-15′-nitroastaxanthin (7), 10′-s-cis-11′-cis-11′-nitroastaxanthin (8), 13,15,13′-tri-cis-15′-nitroastaxanthin (9), 9-cis-astaxanthin (10), and 13-cis-astaxanthin (11), were isolated from the reaction products of carotenoids with peroxynitrite. Our previous studies achieved for the first time the isolation of nitro derivatives from the reaction of astaxanthin with peroxynitrite. Here we identify the major remaining reaction products of this reaction and investigate the stabilities of the nitro astaxanthins. 相似文献
2.
Kenji Mori Noriko Mizumachi Masanao Matsui 《Bioscience, biotechnology, and biochemistry》2013,77(8):1611-1615
The enantiomers of cis-verbenol (4a and 4a′) were first synthesized in optically pure state. (1S, 4S, 5S)-2-Pinen-4-ol (4a′) was dextrorotatory in acetone or in methanol but it was levorotatory in chloroform; cis-verbenols are indistinguishable by a prefix (+) or (?). The designation of the Ips pheromone as (+)-cis-verbenol is therefore ambiguous and it should be called as (1S, 4S, 5S)-2-pinen-4-ol (4a′) or (S)-cis-verbenol. 相似文献
3.
Microbial hydrolysis of the acetates of unsaturated cyclic terpene alcohols by Pseudomonas sp. NOF-5 isolated from soil was investigated. (±)-trans-Carveyl acetate ((±)-trans-3) was enantio-selectively hydrolyzed with NOF-5 strain to give ( – )-trans-carveol (( – )-trans-2 of 86.6% optical purity). However, the hydrolysis of (±)-cis-3 was less enantioselective, while (±)-piperitylacetate ((±)-6, a cis and trans mixture) was hydrolyzed to give the ( – )-trans- and ( – )-cis-piperitols (( – )- trans-5 and ( – )-cis-5) in a poor optical yield. In this case, other tert-alcohols, ( + )-trans- and ( – )- ds-2-p-menthen-1-ols ((±)-trans-7 and ( – )-cis-7), were also produced. Furthermore, microbial and enzymic allyl rearrangements of ( + )-trans-6 and ( – )-trans-verbenylacetate (( – )-trans-11) were studied. Biological treatment of (+)-trans-6 and ( – )-trans-11 with NOF-5 or its esterase gave (+)-trans- and (-)-cis-1 and ( + )-cis-3-pinen-2-ol (( + )-cis-12), respectively. 相似文献
4.
Yoichi Mikami Yumiko Fukunaga Masatoshi Arita Yukiteru Obi Takuro Kisaki 《Bioscience, biotechnology, and biochemistry》2013,77(3):791-793
( ± )-cis-γ-Irone (1a), ( ± )-cis-dihydro-γ-irone (2a) and their trans- isomers (1b, 2b) were synthesized via 3,3-(Claisen) or 2,3-sigmatropic rearrangement of 1-hydroxymethyl-3,3,4- trimethyl-1-cyclo he xene (8) derivatives as each key step. 相似文献
5.
Marie Zarevúcka Martin Rejzek Milan Pavlík Zdeněk Wimmer Jan Zima Marie-Dominique Legoy 《Biotechnology letters》1994,16(8):807-812
Summary The racemic cis and trans isomers 1a and 1b of 2-(4-methoxybenzyl)-1-cyclohexanol were subjects of an enzyme mediated resolution via esterification in organic solvents, in which the chiral esters 2a and 2b of the corresponding alcohols 4a and 4b, and the chiral alcohols 3a and 3b were obtained. The chemical yield and enantioselectivity of this enzymatic reaction have been found to depend mainly on (a) the structure of the substrate (cis or trans), (b) temperature, (c) the nature of the enzyme selected, and (d) the nature of the solvent. 相似文献
6.
Sachio Kudo Takayuki Oritani Kyohei Yamashita 《Bioscience, biotechnology, and biochemistry》2013,77(11):2739-2743
Such (+)- and (?)-cis-cycloheximide isomers as isocyclohcximide (1a, 1b), α-epiisocycloheximide (2a, 2b) and neocycloheximide (3a, 3b) were synthesized by aldol condensation of (?)-(2R, 4R)- and (+)-(2S, 4S)-cis-2,4-dimethyl-1-cyclohexanone (5a, 5b). obtained by microbial resolution, with 4-(2-oxoethyl)-2,6-piperidinedione (7). The absolute configuration of the (?)-cis-ketone 5a was confirmed by chemical correlation with natural (2S, 4S, 6S, αR)-cycloheximide (4). The newly synthesized isomer, (?)-α-epiisocycloheximide (2b), showed strong antimicrobial activity against S. cerevisiae andP. oryzae close to that of natural cycloheximide (4). 相似文献
7.
Abstract The synthesis of carbocyclic nucleosides, cis-9-[4-(1,2-dihydroxyethyl)-cyclopent-2-enyl]guanine (3) and cis-2-amino-6-cyclopropylamino-9-[4-(1,2-dihydroxyethyl)-cyclopent-2-enyl]guanine (4), was achieved from cyclopentadiene (5) in five and six steps, respectively. This route involves a hetero Diels-Alder reaction and a Pd(0)-catalyzed coupling reaction. 相似文献
8.
Urs M. Tuor Hans E. Schoemaker Matti S. A. Leisola Harald W. H. Schmidt 《Applied microbiology and biotechnology》1993,38(5):674-680
The metabolism of quinones formed in the enzymatic oxidation of veratryl alcohol (3,4-dimethoxybenzyl alcohol) (Ia) and its methyl ether Ib in ligninolytic cultures of Phanerochaete chrysosporium was studied. A metabolite of 2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-dione (IIa, formed from Ia by oxidation) was isolated and identified as cis-4-hydroxy-6-hydroxymethyl-3-methoxy-cyclohex-2-en-one (IVa), formally the reduced hydroquinone IIIa. The formation of IVa was also observed when both veratryl alcohol Ia or 2,5-dihydroxy-4-methoxybenzyl alcohol (IIIa), the hydroquinone of IIa, were used as substrates. Analogously, cis-4-hydroxy-3-methoxy-6-methoxymethyl-cyclohex-2-en-one (IVc) was isolated and identified as a metabolite from either 3,4-dimethoxybenzyl methyl ether (Ib) or from its oxidation product 5-methoxy-2-methoxymethyl-2,5-cyclohexadiene-1,4-dione (IIb) as well as from the corresponding hydroquinone 2,5-dihydroxy-4-methoxybenzyl methyl ether (IIIc). The physiological role of these unprecedented conversions is discussed.
Correspondence to: H. E. Schoemaker 相似文献
9.
《Biocatalysis and Biotransformation》2013,31(1-4):49-60
First enantioselective synthesis of S-(-)-1-[3-(4-tert-butylphenyl)-2-methyl]propyl-cis-3,5-dimethylmorpholine (6), biologically active enantiomer of the systematic fungicide fenpropimorph, is reported. It comprises reacting 4-tert-butylbenzylbromide with methyldiethylmalonate, decarbethoxylation of 2 into racemic 3-(4-tert-butylphenyl)-2-methylpropionic acid ethylester (3) in DMSO in the presence of alkali, then Pseudomonas sp. lipase catalyzed kinetic resolution of racemic 3 into S-(+)-acid (4), base-catalyzed racemization and recycling of the R-(-)-ester 3, acylation of cis-3,5-dimethylmorpholine, and final reduction of the intermediary amide 5 to provide enantiomerically pure S-(-)-6. 相似文献
10.
Shunya Takahashi Takayuki Oritani Kyohei Yamashita 《Bioscience, biotechnology, and biochemistry》2013,77(6):1589-1595
( ± )-Methyl phaseates were synthesized from ( ± )-4-(6′-acetoxymethyl-2 ′,6′-dimethyl-1′-cyclohexen-1′-y1)-but-3-en-2-one (20), which was prepared from a useful terpenoid building block, ( ± )-2-hydroxymethyl-2,6-dimethyl-1-cyclohexanone (11a and 11b). Photooxidation of the cyclohexadiene intermediate (22), followed by alkaline hydrolysis and methylation, gave four stereoisomers of ( ± )-methyl phaseates: (2Z,4E)-cis form (2), (2E,4E)-cis form (24), (2Z,4E)-trans form (25) and (2E,4E)-trans form (26). 相似文献
11.
Katsuhiro Takahashi Shigeru Muraki Toshio Yoshida 《Bioscience, biotechnology, and biochemistry》2013,77(1):129-132
(─)-Mintsulfide [(─)-1], a new sulfur-containing sesquiterpene found in peppermint oil, was synthesized from (─)-germacrene-d[(─)-3] by a photochemical reaction and was confirmed to be (1R)-cis-2,6-epithio-cis-8-isopropyl-l-methyl-5-methylene-cis-bicyclo-[5,3,0]decane. The existence of 1 was confirmed in 13 of 74 essential oils analyzed. 相似文献
12.
《Biocatalysis and Biotransformation》2013,31(5):217-221
AbstractTwelve typical commercial hydrolases and crude cell extract of Bacillus subtilis ATCC6633 were tested for their activity to synthesize cis-7-phenylacetamido-3-propenyl-cephalosporanic acid (cis-GPRA) by enzymatic removal of a p-methoxybenzyl protecting group from p-methoxybenzyl-7-phenylacetylamino-3-propenyl-3-cephem-4-carboxylate (GPRE) in aqueous– organic solvents. No activity was detected for 12 commercial enzymes. However, the crude cell extract showed significant activity for removing the p-methoxybenzyl protecting group from GPRE to produce cis-GPRA. The yield of cis-GPRA reached 73% with the initial reaction rate of 10.2 μM h?1 under the optimized reaction conditions. 相似文献
13.
《Archives of animal nutrition》2013,67(5):402-411
Abstract An in vitro study was conducted to determine the effect of different types of fibre supplemented with sunflower oil on ruminal fermentation and formation of conjugated linoleic acids (CLA) by mixed ruminal microorganisms. Cell wall components extracted from wheat straw (representing lignified fibre), soybean hulls (representing easily digestible fibre), and purified cellulose were used as substrates. Sunflower oil was supplemented at the same level for all three types of fibre. After 24 h of incubation, ruminal fermentation parameters (including 24 h gas production, pH value, concentration of ammonia nitrogen and volatile fatty acids) and the concentration of long chain fatty acids in the culture fluid were determined. Results showed that the type of fibre influenced ruminal fermentation traits and the biohydrogenation of unsaturated C18 fatty acids in vitro. Composition of LCFA and profile of CLA were altered by the fibre type. Compared to the digestible fibre and purified cellulose, lignified fibre significantly increased the production of cis-9, trans-11 CLA and total CLA (sum of cis-9, trans-11 CLA, trans-10, cis-12 CLA, trans-9, trans-11 CLA, and cis-9, cis-11 CLA) by ruminal microorganisms. It was concluded that ruminal fermentation and production of CLA can be affected by the type of dietary fibre. 相似文献
14.
M. I. Nieto J. M. Blanco O. CaamañTo F. Fernández X. García-Mera J. Balzarini 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1255-1266
Abstract Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 5–7), 8-azapurine (compounds 9 and 10) or pyrimidine (compound 13) base on the amino group of (1R,cis)-3-(aminornethyl)-1,2,2-trimethylcyclopentylmethanol (2). The antiviral activity of compounds 5–7, 10 and 13, and their cytostatic activity, were evaluated. At subtoxic concentrations, the compounds showed no or marginal antiviral activity. Compound 5 showed moderate inhibition on tumor cell proliferation. 相似文献
15.
Nobuya Katagiri Hiroshi Sato Chikara Kaneko 《Nucleosides, nucleotides & nucleic acids》2013,32(2-4):707-718
Abstract Adenine (7 and 16), thymine (9a and 18a), and 5-fluorouracil (9b and 18b) involving f-2, c-3-bishydroxymethyl-r-1-cyclopropylmethyl- and t-2 t-3-bishydroxymethyl-r-1-cyclopropylmethyl residues were synthesized, starting from trans-1, 4-dibenzyloxy-2-butene and its cis isomer, respectively. These compounds were evaluated for anti HSV-1 activity. 相似文献
16.
José E. R. Borges Franco Fernández Xerardo García Antonio R. Hergueta Carmen López Graciela Andrei 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1237-1253
Abstract (1R,cis)-2-(3-Amino-2,2-dimethylcyclobutyl)ethanol (4) was used as a precursor in the synthesis of cyclobutyl nucleoside analogues containing guanine, 8-azaguanine, adenine or 8-azaadenine. All the compounds were evaluated as antiviral agents in a variety of assay systems. Some activity was noted for compound 13, 17, 19 and 20 against vaccinia virus and for compounds 11, 12, 13, 17, 19 and 20 against herpes simplex virus, at concentrations that were up to 10-fold below the cytotoxic concentrations for the host cells. 相似文献
17.
18.
N Connors R Prevoznak M Chartrain J Reddy R Singhvi Z Patel R Olewinski P Salmon J Wilson R Greasham 《Journal of industrial microbiology & biotechnology》1997,18(6):353-359
Two mutation and selection methods were used to isolate mutants of Pseudomonas putida F1 which convert indene to cis-(1S),(2R)-indandiol in a toluene-independent fashion. Using soybean or silicone oil as a second phase to deliver indene to the culture,
cis-(1S),(2R)-indandiol, cis-(1R),(2S)-indandiol, 1,2-indenediol (or the keto-hydroxy indan tautomer), and the monooxygenation products 1-indenol and 1-indanone
were produced from indene as a function of time. Similarly the enantiomeric excess of the cis-(1S),(2R)-indandiol produced also increased with increasing time. In addition, mutants were isolated which produced cis-(1S),(2R)-indandiol of lower optical purity which corresponded to reduced levels of 1,2-indenediol. These data suggest this toluene
dioxygenase produces cis-(1S),(2R)-indandiol of low optical purity and that cis-glycol dehydrogenase plays a role in resolving the two cis-1,2-indandiol enantiomers.
Received 15 November 1996/ Accepted in revised form 09 March 1997 相似文献
19.
Abstract cis-Disubstituted cyclobutene nucleosides analogues were prepared by a linear synthesis starting from cis-cyclobutene dicarboxylic anhydride. This strategy involved mild reaction conditions with intent to restrict the thermal electrocyclic ring opening into (Z,E)-dienes. 相似文献
20.
M. Carmen Balo Franco Fernández Evangelina Lens Carmen López Erik De Clercq Graciela Andrei 《Nucleosides, nucleotides & nucleic acids》2013,32(7-8):1335-1346
Abstract cis-3-Aminomethylcyclopentylmethanol (4), prepared from norbornene (5) in four steps and 51 % overall yield, was used as a precursor in the synthesis of carbocylic nucleosides 13–18 containing guanine and 8-azaguanine bases. None of these compounds had appreciable activity against fourteen viruses in the concentration range tested. Compounds 13 and 16 showed cytotoxicity to all or part of the cell lines used. 相似文献