10 results on '"Macías-Sánchez, Antonio J"'
Search Results
2. The complemented mutant compl ΔBcstc7 niaD , in the STC7 of Botrytis cinerea led to the characterization of 11,12,13-tri-nor-eremophilenols derivatives.
- Author
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Suárez I, Pinedo C, Aleu J, Durán-Patrón R, Macías-Sánchez AJ, Hernández-Galán R, and Collado IG
- Subjects
- Secondary Metabolism, Botrytis genetics, Plant Diseases
- Abstract
Botrytis cinerea has high potential for the production of specialized metabolites. The recent resequencing of the genome of the B05.10 strain using PacBio technology and the resulting update of the Ensembl Fungi (2017) database in the genome sequence have been instrumental in identifying new genes that could be involved in secondary metabolism. Thus, a new sesquiterpene cyclase (STC) coding gene (Bcstc7) has been included in the gene list from this phytopathogenic fungus. We recently constructed the null and complement transformants in STC7 which enabled us to functionally characterize this STC. Deletion of the Bcstc7 gene abolished (+)-4-epi-eremophilenol biosynthesis, and could then be re-established by complementing the null mutant with the Bcstc7 gene. Chemical analysis of the complemented transformant suggests that STC7 is the principal enzyme responsible for the key cyclization step of farnesyl diphosphate (FDP) to (+)-4-epi-eremophil-9-en-11-ols. A thorough analysis of the metabolites produced by two wild-type strains, B05.10 and UCA992, and the complemented mutant
compl ΔBcstc7niaD , revealed the isolation and structural characterization of six 11,12,13-tri-nor-eremophilene derivatives, in addition to a large number of known eremophilen-11-ol derivatives. The structural characterization was carried out by extensive spectroscopic techniques. The biosynthesis of these compounds is explained by a retroaldol reaction or by dehydration and oxidative cleavage of C11-C13 carbons. This is the first time that this interesting family of degraded eremophilenols has been isolated from the phytopathogenous fungus B. cinerea., (Copyright © 2021 The Authors. Published by Elsevier Ltd.. All rights reserved.)- Published
- 2022
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3. Structural and biosynthetic studies on eremophilenols related to the phytoalexin capsidiol, produced by Botrytis cinerea.
- Author
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Suárez I, da Silva Lima G, Conti R, Pinedo C, Moraga J, Barúa J, de Oliveira ALL, Aleu J, Durán-Patrón R, Macías-Sánchez AJ, Hanson JR, Tallarico Pupo M, Hernández-Galán R, and Collado IG
- Subjects
- Antifungal Agents chemistry, Antifungal Agents metabolism, Botrytis growth & development, Botrytis metabolism, Microbial Sensitivity Tests, Molecular Conformation, Molecular Structure, Sesquiterpenes chemistry, Sesquiterpenes metabolism, Phytoalexins, Antifungal Agents pharmacology, Botrytis chemistry, Fungi drug effects, Plant Diseases microbiology, Sesquiterpenes pharmacology, Triterpenes pharmacology
- Abstract
A thorough study of the fermentation broth of three strains of Botrytis cinerea which were grown on a modified Czapek-Dox medium supplemented with 5 ppm copper sulphate, yielded five undescribed metabolites. These metabolites possessed a sesquiterpenoid (+)-4-epi-eremophil-9-ene carbon skeleton which was enantiomeric to that of the phytoalexin, capsidiol. The isolation of these metabolites when the fungus was stressed, suggests that they may be potential effectors used by B. cinerea to circumvent plant chemical defences against phytopathogenic fungi. The biosynthesis of these compounds has been studied using
2 H and13 C labelled acetate., (Copyright © 2018. Published by Elsevier Ltd.)- Published
- 2018
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4. Chemically Induced Cryptic Sesquiterpenoids and Expression of Sesquiterpene Cyclases in Botrytis cinerea Revealed New Sporogenic (+)-4-Epieremophil-9-en-11-ols.
- Author
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Pinedo C, Moraga J, Barua J, González-Rodríguez VE, Aleu J, Durán-Patrón R, Macías-Sánchez AJ, Hanson JR, Viaud M, Hernández-Galán R, Garrido C, and Collado IG
- Subjects
- Botrytis chemistry, Botrytis genetics, Carbon-Carbon Lyases genetics, Fermentation, Fungal Proteins genetics, Genome, Fungal, Multigene Family, Polycyclic Sesquiterpenes, Sesquiterpenes chemistry, Botrytis metabolism, Carbon-Carbon Lyases metabolism, Fungal Proteins metabolism, Sesquiterpenes metabolism
- Abstract
The sequencing of the genomes of the B05.10 and T4 strains of the fungus Botrytis cinerea revealed an abundance of novel biosynthetic gene clusters, the majority of which were unexpected on the basis of the previous analyses of the fermentation of these and closely related species. By systematic alteration of easy accessible cultivation parameters, using chemical induction with copper sulfate, we have found a cryptic sesquiterpenoid family with new structures related to eremophil-9-ene, which had the basic structure of the sesquiterpene (+)-5-epiaristolochene ((+)-4-epieremophil-9-ene). An expression study of the sesquiterpene cyclase genes present in the Botrytis cinerea genome, under culture conditions, is reported. In general, a 3 day delay and a higher BcSTC genes expression were observed when copper (5 ppm) was fed to the fermentation broth. In addition, to the observed effect on the BcBOT2 (BcSTC1) gene, involved in the biosynthesis of the botrydial toxin, a higher expression level for BcSTC3 and BcSTC4 was observed with respect to the control in the strain B05.10. Interestingly, under copper conditions, the BcSTC4 gene was the most expressed gene in the Botrytis cinerea UCA992 strain. In vitro evaluation of the biological role of these metabolites indicates that they contributed to the conidial development in B. cinerea and appear to be involved in self-regulation of the production of asexual spores. Furthermore, they promoted the formation of complex appressoria or infection cushions.
- Published
- 2016
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5. nor-Mevaldic acid surrogates as selective antifungal agent leads against Botrytis cinerea. Enantioselective preparation of 4-hydroxy-6-(1-phenylethoxy)tetrahydro-2H-pyran-2-one.
- Author
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Botubol-Ares JM, Durán-Peña MJ, Hernández-Galán R, Collado IG, Harwood LM, and Macías-Sánchez AJ
- Subjects
- Aldehydes chemistry, Botrytis growth & development, Botrytis isolation & purification, Colletotrichum growth & development, Colletotrichum isolation & purification, Colony Count, Microbial, Fungicides, Industrial pharmacology, Glutaral chemistry, Hydroxymethylglutaryl-CoA-Reductases, NADP-dependent chemistry, Lactones chemistry, Molecular Mimicry, Phenylethyl Alcohol chemistry, Plant Diseases microbiology, Pyrans pharmacology, Stereoisomerism, Structure-Activity Relationship, Vitis microbiology, Botrytis drug effects, Colletotrichum drug effects, Fungicides, Industrial chemical synthesis, Glutaral analogs & derivatives, Pyrans chemical synthesis
- Abstract
Solvent-free desymmetrisation of meso-dialdehyde 1 with chiral 1-phenylethan-1-ol, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one (+)-3a with a 96:4 dr Deprotected lactone (+)-19a and the related racemic lactones 16a-18a present a lactone moiety resembling the natural substrate of HMG-CoA reductase and their antifungal properties have been evaluated against the phytopathogenic fungi Botrytis cinerea and Colletotrichum gloeosporioides. These compounds were selectively active against B. cinerea, while inactive against C. gloeosporioides., (Copyright © 2015 Elsevier Ltd. All rights reserved.)
- Published
- 2015
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6. Phytotoxic activity and metabolism of Botrytis cinerea and structure-activity relationships of isocaryolane derivatives.
- Author
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Ascari J, Boaventura MA, Takahashi JA, Durán-Patrón R, Hernández-Galán R, Macías-Sánchez AJ, and Collado IG
- Subjects
- Aldehydes chemistry, Aldehydes metabolism, Biotransformation, Bridged Bicyclo Compounds chemistry, Bridged Bicyclo Compounds metabolism, Lactuca growth & development, Lactuca physiology, Molecular Structure, Stereoisomerism, Structure-Activity Relationship, Botrytis metabolism, Fungicides, Industrial chemistry, Fungicides, Industrial pharmacology, Sesquiterpenes chemistry, Sesquiterpenes pharmacology
- Abstract
Research has been conducted on the biotransformation of (8S,9R)-isocaryolan-9-ol (4a) and (1S,2S,5R,8S)-8-methylene-1,4,4-trimethyltricyclo[6.2.1.0(2,5)]undecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6-9, while the biotransformation of compound 5a yielded compounds 10-13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)-Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3, 4a, and 5a, together with their biotransformation products 6-8, 10, and 14-17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7-13 are described for the first time.
- Published
- 2013
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7. Biotransformation of bioactive isocaryolanes by Botrytis cinerea.
- Author
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Ascari J, Boaventura MA, Takahashi JA, Durán-Patrón R, Hernández-Galán R, Macías-Sánchez AJ, and Collado IG
- Subjects
- Biotransformation, Botrytis drug effects, Molecular Structure, Sesquiterpenes chemistry, Spectroscopy, Fourier Transform Infrared, Stereoisomerism, Botrytis metabolism, Fungicides, Industrial metabolism, Sesquiterpenes pharmacology
- Abstract
The metabolism of the fungistatic agent (8R,9R)-8-methoxyisocaryolan-9-ol (4) by the fungus Botrytis cinerea has been investigated. Biotransformation of compound 4 yielded compounds 5 and 6-9. No dihydrobotrydial is observed after 4 days of incubation of compound 4. Separate biotransformation of (8R,9R)-isocaryolane-8,9-diol (5) yielded compounds 7-11. The evaluation of the fungistatic activity against B. cinerea of compounds 4, 5, and 6 is reported. (4R,8R,9R)-8-Methoxyisocaryolane-9,15-diol (6), a major metabolite of (8R,9R)-8-methoxyisocaryolan-9-ol (4), shows a much reduced biological activity when compared with the parent compound. Isocaryolane derivatives 6-11 are described for the first time.
- Published
- 2011
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8. Antifungal activity and biotransformation of diisophorone by Botrytis cinerea.
- Author
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Daoubi M, Deligeorgopoulou A, Macías-Sánchez AJ, Hernández-Galán R, Hitchcock PB, Hanson JR, and Collado IG
- Subjects
- Biotransformation, Botrytis growth & development, Cyclohexanones chemistry, Hydroxylation, Magnetic Resonance Spectroscopy, Molecular Structure, Mycelium growth & development, Plants microbiology, Botrytis drug effects, Botrytis metabolism, Cyclohexanones metabolism, Cyclohexanones pharmacology, Fungicides, Industrial metabolism, Fungicides, Industrial pharmacology
- Abstract
Diisophorone (1) was tested against two strains of the necrotrophic plant pathogen Botrytis cinerea. Fungal sensitivity varied according to the strain. B. cinera 2100 was more sensitive than B. cinereaUCA992: its mycelial growth was significantly inhibited at concentrations of 50 ppm and above. Although diisophorone (1) showed an effective control of B. cinerea, a detoxification mechanism was present. The detoxification of racemic diisophorone (1) by B. cinerea was investigated. Incubation with two strains of B. cinerea gave one and four biotransformation products (2-5), respectively. Their structures were established as the known 8beta-hydroxydiisophorone (2), 6alpha-hydroxydiisophorone (3), 6beta-hydroxydiisophorone (4) and 8beta,14beta-dihydroxydiisophorone (5) on the basis of their spectroscopic data, including two-dimensional NMR analysis [heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser enhancement spectroscopy (NOESY)] and an X-ray crystallographic study.
- Published
- 2005
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9. Structure--activity relationships in the fungistatic activity against Botrytis cinerea of clovanes modified on ring C.
- Author
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Deligeorgopoulou A, Macías-Sánchez AJ, Mobbs DJ, Hitchcock PB, Hanson JR, and Collado IG
- Subjects
- Biotransformation, Bridged Bicyclo Compounds chemical synthesis, Crystallography, X-Ray, Cyclization, Fungicides, Industrial chemical synthesis, Molecular Structure, Oxidation-Reduction, Structure-Activity Relationship, Botrytis drug effects, Bridged Bicyclo Compounds chemistry, Bridged Bicyclo Compounds pharmacology, Fungicides, Industrial chemistry, Fungicides, Industrial pharmacology, Plant Diseases microbiology
- Abstract
The preparation of clovanes 4, 5, 6, 8, and 9, which bear different levels of oxidation on ring C, is described for the first time. The biotransformation of compounds 5, 6, and 9 by the fungus Botrytis cinerea is investigated, yielding compounds 10, 11, and 12, which are described for the first time, together with compounds 4-6, 8, and 9. The evaluation of the fungistatic activity against B. cinerea of compounds 6, 9, 12, 18, 19, 20, and 21 is reported. Comparison of these results with previously published data shows first that the inclusion of hydroxyl groups on ring C leads to a decrease in the biological activity and, second, that the presence of a 9alpha-hydroxyl group and an alkyl chain at C-2 plays an important role in the fungistatic activity against B. cinerea of compounds with a clovane skeleton.
- Published
- 2004
- Full Text
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10. Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols.
- Author
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de Almeida Pinto Bracarense, Adriana, Ascari, Jociani, de Souza, Giovanni Gontijo, Oliveira, Thays Silva, Ruano-González, Antonio, Pinto, Ana A., Boaventura, Maria Amélia Diamantino, Takahashi, Jacqueline Aparecida, Collado, Isidro G., Durán-Patrón, Rosa, and Macías-Sánchez, Antonio J.
- Subjects
BOTRYTIS ,PHYTOTOXICITY ,GERMINATION ,ANTIFUNGAL agents ,LETTUCE - Abstract
Clovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus Botrytis cinerea. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of B. cinerea. Further development of both classes of antifungal agent requires exploration of the structure–activity relationships for the antifungal effects on B. cinerea and phytotoxic effects on a model crop. In this paper, we report on the preparation of a series of alkoxy-clovane and -isocaryolane derivatives, some of them described here for the first time (2b, 2d, 2f–2h, and 4c–4e); the evaluation of their antifungal properties against B. cinerea, and their phytotoxic activites on the germination of seeds and the growth of radicles and shoots of Lactuca sativa (lettuce). Both classes of compound show a correlation of antifungal activity with the nature of side chains, with the best activity against B. cinerea for 2d, 2h, 4c and 4d. In general terms, while 2-alkoxyclovan-9-ols (2a–2e) exert a general phytotoxic effect, this is not the case for 2-arylalkoxyclovan-9-ols (2f–2i) and 8-alkoxyisocaryolan-9-ols (4a–4d), where stimulating effects would make them suitable candidates for application to plants. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
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