The botryane sesquiterpenoid metabolism of the fungus <i>Botrytis cinerea</i>

Collado, Isidro G.; Hanson, James R.; Sánchez, Antonio José Macías

doi:10.3184/174751917x14993374065962

Cited by 3 publications

(4 citation statements)

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“…Another study examined the metabolism of botryane sesquiterpenoids of B. cinerea [ 68 ]. The study of metabolites with botryane and presilphiperfolane skeleton of the fungus B. cinerea has shed light on the biosynthesis of this family of sesquiterpenoids and has also led to potentially novel approaches to the selective control of this pathogen.…”

Section: Botrytis Cinerea Pers Fr (The Anamorph Stage)mentioning

confidence: 99%

“…The study of metabolites with botryane and presilphiperfolane skeleton of the fungus B. cinerea has shed light on the biosynthesis of this family of sesquiterpenoids and has also led to potentially novel approaches to the selective control of this pathogen. An ecological role of the naturally occurring sesquiterpenoids in terms of their effect on the growth of these plant pathogens has been suggested [ 68 ].…”

Section: Botrytis Cinerea Pers Fr (The Anamorph Stage)mentioning

confidence: 99%

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From Genes to Molecules, Secondary Metabolism in Botrytis cinerea: New Insights into Anamorphic and Teleomorphic Stages

Ripardo-Filho

Ruíz

Suárez

et al. 2023

Plants

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The ascomycete Botrytis cinerea Pers. Fr., classified within the family Sclerotiniaceae, is the agent that causes grey mould disease which infects at least 1400 plant species, including crops of economic importance such as grapes and strawberries. The life cycle of B. cinerea consists of two phases: asexual (anamorph, Botrytis cinerea Pers. Fr.) and sexual (teleomorph, Botryotinia fuckeliana (de Bary) Wetzel). During the XVI International Symposium dedicated to the Botrytis fungus, which was held in Bari in June 2013, the scientific community unanimously decided to assign the most widely used name of the asexual form, Botrytis, to this genus of fungi. However, in the literature, we continue to find articles referring to both morphic stages. In this review, we take stock of the genes and metabolites reported for both morphic forms of B. cinerea between January 2015 and October 2022.

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Section: Botrytis Cinerea Pers Fr (The Anamorph Stage)mentioning

confidence: 99%

Section: Botrytis Cinerea Pers Fr (The Anamorph Stage)mentioning

confidence: 99%

From Genes to Molecules, Secondary Metabolism in Botrytis cinerea: New Insights into Anamorphic and Teleomorphic Stages

Ripardo-Filho

Ruíz

Suárez

et al. 2023

Plants

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“…Botrydial is a low molecular weight phytotoxin [26], with a carbon skeleton not following the isoprene rule, which originates from farnesyl diphosphate by folding, cyclization, and a sequence of oxidative transformations [27][28][29][30]. Genes encoding for the relevant steps of the metabolic pathway to botrydial and related compounds have also been elucidated [31,32].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols

Bracarense

Ascari

Souza

et al. 2021

JoF

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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.

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“…cinerea produces a wide variety of low-molecular-weight phytotoxins (Figure ). Botrydial and related botryanes are representative examples. − Chemical and genetic studies revealed that B. cinerea also produces abscisic acid (ABA), which is a well-known plant hormone. , In addition to plants, these metabolites exert toxicity against microorganisms and mammals.…”

Section: Introductionmentioning

confidence: 99%

Effects of Azole Fungicides on Secreted Metabolomes of Botrytis cinerea

Song

Keum

2020

J. Agric. Food Chem.

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Botrytis cinerea, gray mold, is one of the most notorious phytopathgens, causing serious economic loss in the agricultural industry. The phytotoxic effects are mainly derived from secreted virulence proteins and terpenoid-type secondary metabolites. Azole fungicides are commonly used to manage the disease. However, their biochemical effects other than sterol biosynthesis were not documented, especially toxic secreted metabolites. In this study, six azole fungicides were treated with in vitro and in vivo conditions. Comprehensive profiles of primary and secondary metabolites in culture media were evaluated to assess the fungal metabolomes under pesticide-stressed conditions. The results indicated that extensive metabolic differentiation was induced by azole fungicides. Epoxiconazole clearly reduced the extracellular phytotoxin concentrations, while the level of indole-3-acetic acid was increased. In addition, significant differentiation of primary metabolism could be deduced from secreted metabolite profiles, including the tricarboxylic acid cycle and aromatic amino acid catabolism. Cellular lipid profiles, including fatty acids and sterol, have been altered drastically by azoles, which indicate extensive changes of cellular lipid metabolism. These system-wide metabolic alterations resulted in reduced plant damages, proven by the in vivo assay with tomato. Overall, azole fungicides induced significant changes of endo-and exometabolomes and could reduce the fungal infection. The experimental results will provide a more detailed understanding of physiological changes of phytopathogens under pesticide treatment and information for new pesticide development.

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The botryane sesquiterpenoid metabolism of the fungus Botrytis cinerea

Abstract: The evidence is reviewed for the biosynthesis of the phytotoxic sesquiterpenoid botryane metabolites of Botrytis cinerea and its genetic regulation. The use of this information in the development of a novel strategy for the selective control of this fungus is reviewed.

Cited by 3 publications

References 71 publications

From Genes to Molecules, Secondary Metabolism in Botrytis cinerea: New Insights into Anamorphic and Teleomorphic Stages

From Genes to Molecules, Secondary Metabolism in Botrytis cinerea: New Insights into Anamorphic and Teleomorphic Stages

Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols

Effects of Azole Fungicides on Secreted Metabolomes of Botrytis cinerea

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