Eutypa lata

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Pouzoulet Jérôme - One of the best experts on this subject based on the ideXlab platform.

  • Développement d'une méthodologie PCR en temps réel pour la détection et la quantification in planta des principaux champignons pathogènes associés aux maladies du bois de la vigne
    INPT, 2012
    Co-Authors: Pouzoulet Jérôme
    Abstract:

    Les maladies fongiques du bois de la vigne que sont le syndrome de l'esca, le Black Dead Arm (BDA) et l'Eutypiose sont particulièrement dommageables à la profession vitivinicole, et sont actuellement en progression. Le temps d'incubation nécessaire à l'expression de ces maladies au champ complique l'évaluation de solutions préventives adaptées en condition contrôlée ainsi qu'en condition de terrain. Ces travaux de thèse ont eu pour objectifs la conception et la validation de tests PCR quantitatifs en temps réel (RtqPCR), permettant la détection et la quantification in planta de cinq champignons associés aux maladies de dépérissement de la vigne, Phaeomoniella chlamydospora et Phaeoacremonium aleophilum (esca), Diplodia seriata et Neofusicoccum parvum (BDA), et Eutypa lata (Eutypiose). Le développement de tests multiplexes a ensuite été entrepris et ces derniers ont été évalués pour la détection de quatre champignons (2 associés à esca et 2 au BDA) dans le bois de jeunes plants issus de pépinière viticole. Enfin, l'étude de l'interaction in planta de deux champignons associés au syndrome de l'esca de la vigne (P.chlamydospora et P.aleophilum) a été réalisée par RT-qPCR, et complétée par la caractérisation histologique de la réponse de la plante à la blessure dans le bois, en inoculation individuelle et en co-inoculation. ABSTRACT : Grapevine trunk diseases, among which esca's syndrome, Black Dead Arm (BDA) and Eutypiosis, represent a real threat for grape and wine industry. Incubation time required before symptoms externalization in field complicates the evaluation of the efficacy of preventive solution in control and field conditions. These thesis's works focused on the design and the validation of Real Time quantitative PCR assays (RT-qPCR), in order to detect and quantify in vine plant five fungi associated with grapevine trunk disease, Phaeomoniella chlamydospora et Phaeoacremonium aleophilum (esca), Diplodia seriata et Neofusicoccum parvum (BDA), et Eutypa lata (Eutypiosis). The development of multiplex assays was undertaken and these last were evaluated in order to detect four fungi (esca and BDA) in wood sample from young plants in vine nursery. Finally, a study of the interaction between two fungi associated with esca's syndrome has been determined in planta through RT-qPCR, and completed by a histological analysis of plant response to injury of woody tissues

  • Development of a real time PCR methodology for in planta detection and quantification of the main fungal pathogens associated with grapevine trunk diseases
    2012
    Co-Authors: Pouzoulet Jérôme
    Abstract:

    Les maladies fongiques du bois de la vigne que sont le syndrome de l'esca, le Black Dead Arm (BDA) et l'Eutypiose sont particulièrement dommageables à la profession vitivinicole, et sont actuellement en progression. Le temps d'incubation nécessaire à l'expression de ces maladies au champ complique l'évaluation de solutions préventives adaptées en condition contrôlée ainsi qu'en condition de terrain. Ces travaux de thèse ont eu pour objectifs la conception et la validation de tests PCR quantitatifs en temps réel (RtqPCR), permettant la détection et la quantification in planta de cinq champignons associés aux maladies de dépérissement de la vigne, Phaeomoniella chlamydospora et Phaeoacremonium aleophilum (esca), Diplodia seriata et Neofusicoccum parvum (BDA), et Eutypa lata (Eutypiose). Le développement de tests multiplexes a ensuite été entrepris et ces derniers ont été évalués pour la détection de quatre champignons (2 associés à esca et 2 au BDA) dans le bois de jeunes plants issus de pépinière viticole. Enfin, l'étude de l'interaction in planta de deux champignons associés au syndrome de l'esca de la vigne (P.chlamydospora et P.aleophilum) a été réalisée par RT-qPCR, et complétée par la caractérisation histologique de la réponse de la plante à la blessure dans le bois, en inoculation individuelle et en co-inoculation.Grapevine trunk diseases, among which esca's syndrome, Black Dead Arm (BDA) and Eutypiosis, represent a real threat for grape and wine industry. Incubation time required before symptoms externalization in field complicates the evaluation of the efficacy of preventive solution in control and field conditions. These thesis's works focused on the design and the validation of Real Time quantitative PCR assays (RT-qPCR), in order to detect and quantify in vine plant five fungi associated with grapevine trunk disease, Phaeomoniella chlamydospora et Phaeoacremonium aleophilum (esca), Diplodia seriata et Neofusicoccum parvum (BDA), et Eutypa lata (Eutypiosis). The development of multiplex assays was undertaken and these last were evaluated in order to detect four fungi (esca and BDA) in wood sample from young plants in vine nursery. Finally, a study of the interaction between two fungi associated with esca's syndrome has been determined in planta through RT-qPCR, and completed by a histological analysis of plant response to injury of woody tissues

  • Développement d'une méthodologie PCR en temps réel pour la détection et la quantification in planta des principaux champignons pathogènes associés aux maladies du bois de la vigne
    2012
    Co-Authors: Pouzoulet Jérôme
    Abstract:

    Les maladies fongiques du bois de la vigne que sont le syndrome de l'esca, le Black Dead Arm (BDA) et l'Eutypiose sont particulièrement dommageables à la profession vitivinicole, et sont actuellement en progression. Le temps d'incubation nécessaire à l'expression de ces maladies au champ complique l'évaluation de solutions préventives adaptées en condition contrôlée ainsi qu'en condition de terrain. Ces travaux de thèse ont eu pour objectifs la conception et la validation de tests PCR quantitatifs en temps réel (RtqPCR), permettant la détection et la quantification in planta de cinq champignons associés aux maladies de dépérissement de la vigne, Phaeomoniella chlamydospora et Phaeoacremonium aleophilum (esca), Diplodia seriata et Neofusicoccum parvum (BDA), et Eutypa lata (Eutypiose). Le développement de tests multiplexes a ensuite été entrepris et ces derniers ont été évalués pour la détection de quatre champignons (2 associés à esca et 2 au BDA) dans le bois de jeunes plants issus de pépinière viticole. Enfin, l'étude de l'interaction in planta de deux champignons associés au syndrome de l'esca de la vigne (P.chlamydospora et P.aleophilum) a été réalisée par RT-qPCR, et complétée par la caractérisation histologique de la réponse de la plante à la blessure dans le bois, en inoculation individuelle et en co-inoculation

Jeanpaul Roustan - One of the best experts on this subject based on the ideXlab platform.

  • effects of eutypine a toxin from Eutypa lata on plant cell plasma membrane possible subsequent implication in disease development
    Plant Physiology and Biochemistry, 2001
    Co-Authors: Benignee Amborabe, Jeanpaul Roustan, Pierrette Fleuratlessard, Janine Bonmort, Gabriel Roblin
    Abstract:

    Abstract Eutypine, 4-hydroxy-3-(3-methyl-3-butene-1-ynyl) benzaldehyde, is a toxin produced by Eutypa lata, the causal agent of Eutypa dieback. An essential target of eutypine action lies at the plasmalemma as shown by the data obtained during this study on three experimental models (Beta vulgaris, Mimosa pudica, Vitis vinifera). The fungal toxin at 100 μM triggered a rapid dose-dependent hyperpolarization of the membrane potential in M. pudica pulvinar cells. It also enhanced proton permeability in plant tissues or in purified plasma membrane vesicles (PMV) without modification of the H+-ATPase activity. As a physiological consequence, eutypine hindered sucrose and valine absorption by PMV and plant tissues. In all these situations, eutypine behaved like a protonophoric compound, such as dinitrophenol (DNP) used at 10 μM, and acted specifically since eutypinol, an inactive derivative, only triggered very limited effects at a 100-μM concentration. Eutypine did not modify phenylalanine ammonia lyase (PAL, EC 4.3.1.5) activity, suggesting that its toxic action has no after-effect on the secondary metabolism.

  • enzymatic detoxification of eutypine a toxin from Eutypa lata by vitis vinifera cells partial purification of an nadph dependent aldehyde reductase
    Planta, 1999
    Co-Authors: Segolene Colrat, Alain Latche, Mondher Bouzayen, J Fallot, Corine Deswarte, Alain Klaebe, Jeanpaul Roustan
    Abstract:

    Eutypine, 4-hydroxy-3-(3-methyl-3-butene-1-ynyl) benzaldehyde, is a toxin produced by Eutypa lata (Pers.: Fr.) Tul., the causal agent of dying arm disease of Vitis vinifera L. (grapevine). Previously, we have shown that eutypine is involved in the development of disease symptoms. In the present study, the effects of V. vinifera cell-suspension cultures on the biological activity of the toxin were investigated. Eutypine was converted by grapevine tissues into a single compound, identified by mass spectrometry and nuclear magnetic resonance as 4-hydroxy-3-(3-methyl-3-butene-1-ynyl) benzyl alcohol, designated eutypinol. This compound was found to be non-toxic for grapevine tissues. Unlike eutypine, eutypinol failed to affect the oxidation rate or membrane potential of isolated mitochondria. In grapevine cells, reduction of eutypine into the corresponding alcohol is an NADPH-dependent enzymatic reaction. An enzyme which reduced eutypine was partially purified, over 1000-fold, using a five-step purification procedure. By gel filtration and sodium dodecyl sulfate-polyacrylamide gel electrophoresis, the protein was found to have a molecular mass of 54–56 kDa. The enzyme exhibited an apparent Km for eutypine of 44 μM, and was active between pH 6.8 and 7.5 with a maximum at pH 7.0. The eutypine reductase activity was improved by Mn2+ and Mg2+ and inhibited by disulfiram and p-hydroxymercuribenzoate. The possible role of the eutypine-detoxification mechanism in the defense reactions of V. vinifera cells is discussed.

  • purification and characterization of a nadph dependent aldehyde reductase from mung bean that detoxifies eutypine a toxin from Eutypa lata
    Plant Physiology, 1999
    Co-Authors: Segolene Colrat, Alain Latche, Monique Guis, Jeanclaude Pech, Mondher Bouzayen, J Fallot, Jeanpaul Roustan
    Abstract:

    Eutypine (4-hydroxy-3-[3-methyl-3-butene-1-ynyl] benzaldehyde) is a toxin produced by Eutypa lata , the causal agent of Eutypa dieback in the grapevine ( Vitis vinifera ). Eutypine is enzymatically converted by numerous plant tissues into eutypinol (4-hydroxy-3-[3-methyl-3-butene-1-ynyl] benzyl alcohol), a metabolite that is nontoxic to grapevine. We report a four-step procedure for the purification to apparent electrophoretic homogeneity of a eutypine-reducing enzyme (ERE) from etiolated mung bean ( Vigna radiata ) hypocotyls. The purified protein is a monomer of 36 kD, uses NADPH as a cofactor, and exhibits a K m value of 6.3 μm for eutypine and a high affinity for 3- and 4-nitro-benzaldehyde. The enzyme failed to catalyze the reverse reaction using eutypinol as a substrate. ERE detoxifies eutypine efficiently over a pH range from 6.2 to 7.5. These data strongly suggest that ERE is an aldehyde reductase that could probably be classified into the aldo-keto reductase superfamily. We discuss the possible role of this enzyme in eutypine detoxification.

  • a novel nadph dependent aldehyde reductase gene from vigna radiata confers resistance to the grapevine fungal toxin eutypine
    Plant Journal, 1998
    Co-Authors: Pedro Guillen, Segolene Colrat, Monique Guis, Mondher Bouzayen, J Fallot, Jeanpaul Roustan, Corine Deswarte, Gracia Martinezreina, Sylvie Dalmayrac, Jeanclaude Pech
    Abstract:

    Eutypine, 4-hydroxy-3-(3-methyl-3-butene-1-ynyl) benzyl aldehyde, is a toxin produced by Eutypa lata, the causal agent of Eutypa dieback of grapevines. It has previously been demonstrated that tolerance of some cultivars to this disease was correlated with their capacity to convert eutypine to the corresponding alcohol, eutypinol, which lacks phytotoxicity. We have thus purified to homogeneity a protein from Vigna radiata that exhibited eutypine-reducing activity and have isolated the corresponding cDNA. This encodes an NADPH-dependent reductase of 36 kDa that we have named Vigna radiata eutypine-reducing enzyme (VR-ERE), based on the capacity of a recombinant form of the protein to reduce eutypine into eutypinol. The strongest homologies (86.8%) of VR-ERE at the amino acid level were found with CPRD14, a drought-inducible gene of unknown function, isolated from Vigna unguiculata and with an aromatic alcohol dehydrogenase (71.7%) from Eucalyptus gunnii. Biochemical characterization of VR-ERE revealed that a variety of compounds containing an aldehyde group can act as substrates. However, the highest affinity was observed with 3-substituted benzaldehydes. Expression of a VR-ERE transgene in Vitis vinifera cells cultured in vitro conferred resistance to the toxin. This discovery opens up new biotechnological approaches for the generation of grapevines resistant to Eutypa dieback.

  • protonophoric activity of eutypine a toxin fromEutypa lata in plant mitochondria
    Archives of Biochemistry and Biophysics, 1996
    Co-Authors: Corine Deswarte, Jeanpaul Roustan, Joelle Eychenne, Jacques Davy De Virville, Francois Moreau, J Fallot
    Abstract:

    Abstract Eutypine is a toxin produced by Eutypa lata, the causal agent of the dying-arm disease of grapevine. We have previously shown that this toxin behaves as a lipophylic weak acid (p K = 6.2) and induces drastic changes in both the respiration and energy balance of grapevine cells. In the present study, the molecular mode of action of eutypine at the mitochondrial level, using methyl-eutypine, the unprotonable derivative of the toxin, has been investigated. The effects of these molecules on mitochondrial respiration and membrane potential were compared using isolated mitochondria from grapevine cells in suspension cultures or potato tuber mitochondria. Eutypine induces marked stimulation of oxygen consumption and a depolarizing effect, while methyl-eutypine exhibits a very small effect on both the rate of oxygen uptake and membrane potential. For high eutypine concentrations, a mixed effect corresponding to a direct inhibition of electron transport and uncoupling can be observed. In addition, below 200 μ M , eutypine displays a linear relationship between oxidation rate and membrane potential similar to that of the classical protonophore carbonyl cyanide- m -chlorophenylhydrazone (CCCP). However, unlike CCCP, eutypine induces a potential-dependent proton conductance that can be due to the potential-dependent migration of the dissociated form of the toxin across the membrane. It is concluded that eutypine uncouples mitochondrial oxidative phosphorylation and decreases the ADP/O ratio in grapevine cells by increasing the proton leaks via a cyclic protonophore mechanism. The physiological aspects of these results are discussed.

W D Gubler - One of the best experts on this subject based on the ideXlab platform.

  • phomopsis dieback a grapevine trunk disease caused by phomopsis viticola in california
    Plant Disease, 2013
    Co-Authors: J R Urbeztorres, F Peduto, Rhonda J Smith, W D Gubler
    Abstract:

    Abstract Field surveys recently conducted in California and in other grape-growing regions in the United States showed Phomopsis viticola to be one of the most prevalent fungi isolated from grapevine perennial cankers in declining vines. The current study has not only confirmed the presence of P. viticola from grapevine cankers in California but also has for the first time revealed the occurrence of Diaporthe ambigua, D. eres, and D. neotheicola in symptomatic grapevine wood in California by means of morphological studies and multi-gene sequence analysis. Pathogenicity trials conducted on mature cordons of Vitis vinifera ‘Syrah’ and ‘Red Globe’, as well as on lignified Syrah dormant canes, showed P. viticola isolates from California to be capable of causing perennial cankers. Lengths of vascular discoloration caused by P. viticola were similar to those caused by Eutypa lata and several Botryosphaeriaceae spp., which are well-known grapevine trunk disease pathogens. Additionally, a lack of spring growth wa...

  • phomopsis dieback a grapevine trunk disease caused by phomopsis viticola in california
    Plant Disease, 2013
    Co-Authors: J R Urbeztorres, F Peduto, Rhonda J Smith, W D Gubler
    Abstract:

    Field surveys recently conducted in California and in other grape-growing regions in the United States showed Phomopsis viticola to be one of the most prevalent fungi isolated from grapevine perennial cankers in declining vines. The current study has not only confirmed the presence of P. viticola from grapevine cankers in California but also has for the first time revealed the occurrence of Diaporthe ambigua, D. eres, and D. neotheicola in symptomatic grapevine wood in California by means of morphological studies and multi-gene sequence analysis. Pathogenicity trials conducted on mature cordons of Vitis vinifera 'Syrah' and 'Red Globe', as well as on lignified Syrah dormant canes, showed P. viticola isolates from California to be capable of causing perennial cankers. Lengths of vascular discoloration caused by P. viticola were similar to those caused by Eutypa lata and several Botryosphaeriaceae spp., which are well-known grapevine trunk disease pathogens. Additionally, a lack of spring growth was commonly observed in dormant canes inoculated with P. viticola spore suspensions in two pathogenicity trials. As part of this study, V. vinifera 'Cabernet Sauvignon' and 'Zinfandel' wood was shown to be more susceptible to infection by P. viticola than 'Barbera', 'Chardonnay', 'Merlot', and 'Thompson Seedless' wood. After more than 40 years overlooking P. viticola as a grapevine wood pathogen, this study provides strong evidence of the role of P. viticola as a canker-causing organism, and suggests its addition to the fungi involved in the grapevine trunk disease complex. Results from this study suggest D. ambigua and D. neotheicola to be saprophytes or weak pathogens on grapevine wood.

  • diversity of diatrypaceous fungi associated with grapevine canker diseases in california
    Mycologia, 2010
    Co-Authors: Florent P. Trouillas, J R Urbeztorres, W D Gubler
    Abstract:

    Eutypa lata is the most common diatrypaceous fungus in grapevine cankers. This study was undertaken to determine the presence and diversity of other members of the Diatrypaceae in grapevines in California. We isolated into pure culture 11 species of Diatrypaceae from the wood of diseased grapevines including Cryptosphaeria pullmanensis, Cryptovalsa ampelina, Diatrype oregonensis, D. stigma, D. whitmanensis, Diatrype sp., Diatrypella verrucaeformis and four putative species of Eutypella. Species were identified or grouped morphologically and by phylogenetic analyses of the complete sequence of the internal transcribed spacer (ITS) of the rDNA and β-tubulin gene. Diatrypaceous fungi also occurred frequently on the native flora surrounding vineyards, thus serving as possible inoculum sources for these putative pathogens.

  • use of boron for the control of Eutypa dieback of grapevines
    Plant Disease, 2005
    Co-Authors: Philippe E Rolshausen, W D Gubler
    Abstract:

    ABSTRACT Eutypa dieback is a perennial canker disease of grapevine (Vitis vinifera) caused by Eutypa lata. The fungus produces ascospores, which infect grapevines through pruning wounds during the dormant season. Management of the disease has been achieved with fungicide applications during the dormant period. However, no effective fungicide was available for this purpose after Benlate was withdrawn from the market. Boric acid (17.5% a.i. boron), a potential alternative to Benlate, was tested in the present study against E. lata. The EC50 values for inhibition of mycelial growth and ascospore germination were 125 and 475 μg of boric acid per ml (22 and 83 μg a.i./ml), respectively. Two boron-based treatments were developed and tested in vitro and in four field trials during 2001 to 2003. One product, biopaste, contained 5% boric acid (8.75 mg a.i./ml) in a commercial paste. The second product, bioshield, contained 5% boric acid in a spore suspension of Cladosporium herbarum. Both products significantly re...

Fallot J. - One of the best experts on this subject based on the ideXlab platform.

  • Biodégradation des lignocelluloses de vigne (Vitis vinifera cv. Cabernet Sauvignon) par Eutypa lata (PERS. FR.) TUL.
    VITIS - Journal of Grapevine Research, 2015
    Co-Authors: Elghazali B., Gas G., Fallot J.
    Abstract:

    Biodegradation of lignocelluloses in grapevine (Vitis vinifera cv. Cabernet Sauvignon) by Eutypa lata (PERS. FR.) TUL.The biodegradation of lignocelluloses in Vitis vinifera cv. Cabernet Sauvignon by the parasitic fungus Eutypa lata was studied in dependence on culture conditions. By use of lignocelluloses labelled with 14C in two different ways, it was possible for the first time to determine the degradation rates of two main parietal constituents, cellulose and lignin. The rate of lignin decomposition in the overall degradation was constantly weak. This can explain the prolonged time span needed for mycelium development in the trunk or in the arms (3-10 years). The just slight lignin degradation may also be responsible for the hardness of the attacked tissue. The fungus activity was stimulated when E. lata was cultivated in media of low nitrogen and sugar concentration and in an atmosphere which was rich in oxygen. These reactions are similar to those shown by Phanerochaete chrysosporium, lignivorous fungus most often reported. Several pathotypes of E. lata showed similar aggressiveness, whereas in studies using other model systems their toxicity was more or less different

  • Ultrastructural changes produced in plantlet leaves and protoplasts of Vitis vinifera cv. Cabernet Sauvignon by eutypine, a toxin from Eutypa lata
    VITIS - Journal of Grapevine Research, 2015
    Co-Authors: Deswarte Corine, Rouquier R., Roustan J. P., Dargent R., Fallot J.
    Abstract:

    Eutypine is a toxin produced by Eutypa lata (Pers.: Pr.) Tul., the causal agent of dying-arm disease of the grapevine. Ultrastructural alterations induced by eutypine in leaf cells and protoplasts isolated from plantlets of Vitis vinifera cv. Cabernet Sauvignon, a very sensitive variety cultured in vitro, were observed for the first time by transmission electron microscopy. Eutypine caused early cytoplasm lysis and vesiculation followed by chloroplast swelling with thylakoid dilation. The eutypine-induced alterations of the cellular ultrastructure are similar to those previously described in vivo in the leaves of diseased grapevines. These results confirm that eutypine, synthesized by E. lata mycelium present in the trunk or arms, is involved in symptom expression of eutypiosis in the herbaceous parts of grapevine

  • Effets de l'eutypiose sur des feuilles de Vitis vinifera cv. Cabernet Sauvignon. Etude cytologique
    VITIS - Journal of Grapevine Research, 2015
    Co-Authors: Fallot J., Petitprez M., Dargent R.
    Abstract:

    Effects of Eutypa dieback on the leaves of Vitis vinifera cv. Cabernet Sauvignon. Cytological studiesThe fungus Eutypa lata only grows in lignified wood (trunk and arms) and causes at a distance typical symptoms on the leaves of Vitis vinifera cv. Cabernet Sauvignon, a very sensitive variety. For the first time, lesions induced in vivo in leaf cells were examined by transmission electron microscopy. The main alterations of ultrastructure are depending on the level of disease. In the cells of slightly affected leaves, the enlarged chloroplasts show dilated thylakoids with a lowered electron density and sometimes contain very large starch grains. In the severely affected leaves, the cells are completely disorganized, with plasmalemma retraction, chloroplast degradation, cytoplasm lysis and endomembrane breakdown. These results suggest that structural decline of the photosynthetic system can be responsible, at least partly, for the death of Cabernet Sauvignon grapevines

Pinedo-rivilla Cristina - One of the best experts on this subject based on the ideXlab platform.

  • Asymmetric microbial conversion of (E)-2-benzylideneindan-1-one by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata
    'Elsevier BV', 2011
    Co-Authors: Pinedo-rivilla Cristina, Aleu Casatejada Josefina, González Collado Isidro
    Abstract:

    The transformation of (E)-2-benzylideneindan-1-one 1 by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata as biocatalysts was studied. The results showed the catalytic potential of these fungi in affording several hydroxylation and reduction products, three of them reported here for the first time. The absolute configuration of enantiomerically pure 2-benzylindane derivatives was determined

  • Asymmetric microbial reduction of ketones: absolute configuration of trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol
    Pergamon-Elsevier B.V. Ltd, 2009
    Co-Authors: Pinedo-rivilla Cristina, Cafêu, Mariana Carrara, Casatejada, Josefina Aleu, Regina Araujo Angela, Collado, Isidro G.
    Abstract:

    A set of five fungal species, Botrytis cinerea, Trichoderma viride and Eutypa lata, and the endophytic fungi Colletotrichum crassipes and Xylaria sp., was used in screening for microbial biocatalysts to detect monooxygenase and alcohol dehydrogenase activities (for the stereoselective reduction of carbonyl compounds). 4-Ethylcyclohexanone and acetophenone were biotransformed by the fungal set. The main reaction pathways involved reduction and hydroxylations at several positions including tertiary carbons. B. cinerea was very effective in the bioreduction of both substrates leading to the chiral alcohol (S)-1-phenylethanol in up to 90% enantiomeric excess, and the cis-trans ratio for 4-ethylcyclohexanol was 0:100. trans-4-Ethyl-1-(1S-hydroxyethyl)cyclohexanol, obtained from biotransformation by means of an acyloin-type reaction, is reported here for the first time. The absolute configurations of the compounds trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol and 4-(1S- and 4-(1R-hydroxyethyl)cyclohexanone were determined by NMR analysis of the corresponding Mosher's esters. (C) 2009 Elsevier Ltd. All rights reserved

  • Asymmetric microbial reduction of ketones: absolute configuration of trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol
    'Elsevier BV', 2009
    Co-Authors: Pinedo-rivilla Cristina, Regina Araujo Angela, Carrara Mafeu Mariana, González Collado Isidro, Aleu Casatejada Josefina
    Abstract:

    A set of five fungal species, Botrytis cinerea, Trichoderma viride and Eutypa lata, and the endophytic fungi Colletotrichum crassipes and Xylaria sp., was used in screening for microbial biocatalysts to detect monooxygenase and alcohol dehydrogenase activities (for the stereoselective reduction of carbonyl compounds). 4-Ethylcyclohexanone and acetophenone were biotransformed by the fungal set. The main reaction pathways involved reduction and hydroxylations at several positions including tertiary carbons. B. cinerea was very effective in the bioreduction of both substrates leading to the chiral alcohol (S)-1- phenylethanol in up to 90% enantiomeric excess, and the cis–trans ratio for 4-ethylcyclohexanol was 0:100. trans-4-Ethyl-1-(1S-hydroxyethyl)cyclohexanol, obtained from biotransformation by means of an acyloin-type reaction, is reported here for the first time. The absolute configurations of the compounds trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol and 4-(1S- and 4-(1R-hydroxyethyl)cyclohexanone were determined by NMR analysis of the corresponding Mosher’s esters

Related terms

  • vitis vinifera cv cabernet
  • vigne vitis vinifera cv
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