A Shared Biosynthetic Pathway for Botcinins and Botrylactones Revealed through Gene Deletions

Massaroli, Michelli; Moraga, Javier; Borges, Keyller Bastos; Ramírez-Fernández, Jacinto; Viaud, Muriel; Collado, Isidro González; Durán-Patrón, Rosa; Hernández-Galán, Rosario

doi:10.1002/cbic.201200487

Cited by 14 publications

(12 citation statements)

References 24 publications

(52 reference statements)

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“…Furthermore, there are several elements that are clearly involved in this interaction. These include BOT exogenously added or produced by B05.10, Botcs added to the medium or produced by bcbot2Δ , HA produced by Ta37, other SMs produced by B05.10 (botcinic acid, Moraga et al ., ; botrylactones, Massaroli et al ., ) and Ta37 (aspinolides, Malmierca et al ., ), and the hydrolytic enzymes and signalling molecules generated in the interaction zone that can act as signals even far away from the confrontation region. The cross‐pathway interactions established between these SMs, together with the hydrolytic enzyme activity, observed in the present work, and with the ability of HA to inhibit the germination of B. cinerea spores (Malmierca et al ., ), contribute to explain why T. arundinaceum is able to overcome and suppress the virulence mechanisms exhibited by the pathogen.…”

Section: Discussionmentioning

confidence: 99%

Botrydial and botcinins produced by Botrytis cinerea regulate the expression of Trichoderma arundinaceum genes involved in trichothecene biosynthesis

Malmierca

Izquierdo-Bueno

McCormick

et al. 2016

Molecular Plant Pathology

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Trichoderma arundinaceum IBT 40837 (Ta37) and Botrytis cinerea produce the sesquiterpenes harzianum A (HA) and botrydial (BOT), respectively, and also the polyketides aspinolides and botcinins (Botcs), respectively. We analysed the role of BOT and Botcs in the Ta37-B. cinerea interaction, including the transcriptomic changes in the genes involved in HA (tri) and ergosterol biosynthesis, as well as changes in the level of HA and squalene-ergosterol. We found that, when confronted with B. cinerea, the tri biosynthetic genes were up-regulated in all dual cultures analysed, but at higher levels when Ta37 was confronted with the BOT non-producer mutant bcbot2Δ. The production of HA was also higher in the interaction area with this mutant. In Ta37-bcbot2Δ confrontation experiments, the expression of the hmgR gene, encoding the 3-hydroxy-3-methylglutaryl coenzyme A reductase, which is the first enzyme of the terpene biosynthetic pathway, was also up-regulated, resulting in an increase in squalene production compared with the confrontation with B. cinerea B05.10. Botcs had an up-regulatory effect on the tri biosynthetic genes, with BotcA having a stronger effect than BotcB. The results indicate that the interaction between Ta37 and B. cinerea exerts a stimulatory effect on the expression of the tri biosynthetic genes, which, in the interaction zone, can be attenuated by BOT produced by B. cinerea B05.10. The present work provides evidence for a metabolic dialogue between T. arundinaceum and B. cinerea that is mediated by sesquiterpenes and polyketides, and that affects the outcome of the interaction of these fungi with each other and their environment.

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Section: Discussionmentioning

confidence: 99%

Botrydial and botcinins produced by Botrytis cinerea regulate the expression of Trichoderma arundinaceum genes involved in trichothecene biosynthesis

Malmierca

Izquierdo-Bueno

McCormick

et al. 2016

Molecular Plant Pathology

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“…[14][15][16][17] Botcinins 18 originated through poliketide biosynthetic pathway. 19,20 Gene silencing studies have shown that blockade of one toxin metabolic pathway does not completely eliminate the pathogenicity of the fungus, due to the metabolic switch to another fungal toxin pathway. 21,22 At the same time, genomic studies have been unraveling the complex metabolic potential of this versatile phytopathogen, showing that the genome of B. cinerea comprises 45 genes encoding secondary metabolites key enzymes including 22 polyketide synthases (PKSs), 8 non-ribosomal peptide synthetases (NRPSs), 5 PKS/NRPS, six sesquiterpene cyclases (STCs), three diterpene cyclases (DTCs) and one dimethylallyl tryptophan synthase (DMATS).…”

Section: Introductionmentioning

confidence: 99%

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

Botubol-Ares

Durán‐Peña

Hernández-Galán

et al. 2015

Bioorganic & Medicinal Chemistry

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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.

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“…These are the botrylactones, and the botcinic and botcineric acids with their cyclic relatives, the botcinins. 3 The structure, 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1), has been assigned to a metabolite which was isolated from a mutant strain of B. cinerea. This structure ( Fig.…”

Section: Introductionmentioning

confidence: 99%

The synthesis of 3-hydroxy-2,4,8-trimethyldec-8-enolides and an approach to 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide

et al. 2015

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The synthesis of several derivatives of 3-hydroxy-2,4,8-trimethyldec-8-enolide and attempts at the synthesis of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1), a structure which has been assigned to a metabolite of the phytopathogenic fungus, Botrytis cinerea, gave products whose spectroscopic data had significant differences from those reported for the natural product 1. The rare 11-membered lactone rings were constructed by ring-closing metathesis reactions. The increase in conformational restrictions imposed by the substituents has a high influence on the stereochemistry of the ring-closing metathesis reaction and gives rise to a decrease in the yield for the synthesis of 11-membered lactones. The predominant alkene which was obtained was the (Z)-isomer. The observed spectroscopic differences between the synthesized lactones and the natural product and the spectroscopic data of its acetylated derivative 26a allowed us to revise the structure 1 to that of the γ-butyrolactone 26.

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A Shared Biosynthetic Pathway for Botcinins and Botrylactones Revealed through Gene Deletions

Cited by 14 publications

References 24 publications

Botrydial and botcinins produced by Botrytis cinerea regulate the expression of Trichoderma arundinaceum genes involved in trichothecene biosynthesis

Botrydial and botcinins produced by Botrytis cinerea regulate the expression of Trichoderma arundinaceum genes involved in trichothecene biosynthesis

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

The synthesis of 3-hydroxy-2,4,8-trimethyldec-8-enolides and an approach to 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide

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