Four new spiroaxane sesquiterpenes and one new rosenonolactone derivative from cultures of Basidiomycete Trametes versicolor

Wang, Su-Rui; Zhang, Ling; Chen, He‐Ping; Li, Zhenghui; Dong, Zhibao; Liu, Ji‐Kai

doi:10.1016/j.fitote.2015.06.017

Cited by 12 publications

(3 citation statements)

References 18 publications

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“…A new sesquiterpenoid 54 was isolated from the fungus Pholiota nameko [36]. Tramspiroins A-D 55-58 have been isolated from the cultures of Basidiomycete Trametes versicolor [37].…”

Section: Bergamotane Spiroaminal and Spiroaxanementioning

confidence: 99%

Sesquiterpenoids Specially Produced by Fungi: Structures, Biological Activities, Chemical and Biosynthesis (2015–2020)

Quan

Zhang

Feng

2021

JoF

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Fungi are widely distributed in the terrestrial environment, freshwater, and marine habitat. Only approximately 100,000 of these have been classified although there are about 5.1 million characteristic fungi all over the world. These eukaryotic microbes produce specialized metabolites and participate in a variety of ecological functions, such as quorum detection, chemical defense, allelopathy, and maintenance of symbiosis. Fungi therefore remain an important resource for the screening and discovery of biologically active natural products. Sesquiterpenoids are arguably the richest natural products from plants and micro-organisms. The rearrangement of the 15 high-ductility carbons gave rise to a large number of different skeletons. At the same time, abundant structural variations lead to a diversification of biological activity. This review examines the isolation, structural determination, bioactivities, and synthesis of sesquiterpenoids that were specially produced by fungi over the past five years (2015–2020).

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“…A new sesquiterpenoid 54 was isolated from the fungus Pholiota nameko [36]. Tramspiroins A-D 55-58 have been isolated from the cultures of Basidiomycete Trametes versicolor [37].…”

Section: Bergamotane Spiroaminal and Spiroaxanementioning

confidence: 99%

Sesquiterpenoids Specially Produced by Fungi: Structures, Biological Activities, Chemical and Biosynthesis (2015–2020)

Quan

Zhang

Feng

2021

JoF

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“…1-phenyl-3-methylpyrazolones oxidoreductase mediators [297] aryl tetral226in lignans bioactive compounds [298] podophyllotoxin bioactive compounds [298] Trametes versicolor funatrol D bioactive compound [299] isodrimenediol sesquiterpenes (anticancer) [299] tramspiroins sesquiterpenes (anticancer) [299] triterpenes bioactive compounds [300] Database on potential toxigenic capacities of microorganisms used for industrial production 2,4-di-tert-butylphenol bioactive compound [310] 2,6,10-trimethylundeca-5,9-dienal bioactive compound [310] 2-phenylethanol bioactive compound [311] 6-pentyl-alpha-pyrone bioactive compound [312,313] 6-methyl-1,3,8-trihydroxyanthraquinone antifungal [308] 6-n-pentyl-a-pyrone bioactive compound [311] 6-pentyl-2H-pyran-2-one antifungal [308] alpha-cubebene bioactive compound [310] alpha-curcumene bioactive compound [310] anthraquinones antifungal [314] azaphilone antifungal [307,309] b-bisabolene bioactive compound [310] biformen (6CI) bioactive compound [310] butenolide antifungal [307,309] [318] gliotoxin bioactive compound [319] gliovirin bioactive compound [319,320] harzianic acid siderophore [321] harzianolide anti-phytopathogen [307,309,322] harzianopyridone anti-phytopathogen [307][308][309] harziphilone bioactive compound [318] hexahydrofarnesol bioactive compound …”

Section: Trametes Hirsutamentioning

confidence: 99%

Database on the taxonomical characterisation and potential toxigenic capacities of microorganisms used for the industrial production of food enzymes and feed additives, which do not have a recommendation for Qualified Presumption of Safety

Benito

Ibáñez

Moncho

et al. 2017

EFSA Supporting Publications

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The present work constitutes the external scientific report of the EFSA open call OC/EFSA/FEED/2015/01. The aim of the call was to provide EFSA with a database from a review on the taxonomical description and potential toxigenic capacities of microorganisms used for the industrial production of feed additives and food enzymes. The review includes microorganisms used as source of feed additives and food enzymes for which EFSA has received or can potentially receive applications for safety assessment, and which have not been recommended for Qualified Presumption of Safety status. The database also comprises the molecular taxonomical identifiers and biosynthetic pathways involved in the production of toxic compounds and the responsible genes. The main result of the project is shown as a database developed according to the EFSA data structure. The methodological aspects and the queries used in the systematic search, as well as the procedure applied for the screening of scientific documents retrieved are described in this report. Details are available in supplementary appendices.In total, 22970 scientific documents were screened in the literature search, from which 411 were initially selected for providing pertinent data for the scope of the project. From the review of the selected articles, 474 bioactive secondary metabolites were recorded and 59 compounds were further studied in order to obtain data on their toxicology and the conditions in which they are produced by the microorganisms used in industrial fermentations. The database generated in this project comprises details that characterise, when available, the production conditions, genes involved and toxicity of these 59 compounds. This provides information that can be used to establish safety measures when using potentially toxigenic microorganisms in industrial fermentations Disclaimer: The present document has been produced and adopted by the bodies identified above as author(s). This task has been carried out exclusively by the author(s) in the context of a contract between the European Food Safety Authority and the author(s), awarded following a tender procedure. The present document is published complying with the transparency principle to which the Authority is subject. It may not be considered as an output adopted by the Authority. The European Food Safety Authority reserves its rights, view and position as regards the issues addressed and the conclusions reached in the present document, without prejudice to the rights of the authors. Acknowledgements:We thank the following EFSA satff: Jaime Aguilera, Margarita Aguilera-Gómez, Jane Richardson, Mario Monguidi and Davide Gibin for their valuable help and collaboration throughout the project. We also would like to thank the members of AINIA: Sonia Porta, Lidia Tomás, Joaquin Espí and Juan Antonio Nieto for providing expertise in biotechnology and molecular biology and contributing with their efforts to achieve the goals of this project, and Violeta Gómez from the University of Navarra for her colla...

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“…Compounds with a spiro[4.5]decane motif (Figure ) are commonly distributed in natural products, such as sesquiterpenoids, sesquiterpene dimers, diterpenoids, triterpenoids, tetracycline antibiotics, and alkaloids, etc. A series of reactions, like Heck reaction, Diels–Alder reaction, Claisen rearrangement reaction, and Aldol condensation reaction, have been successfully applied to establish the core spiro[4.5]decane motif during the total synthesis of natural products in this family.…”

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confidence: 99%

Isolation and Bioinspired Total Synthesis of Rugosiformisin A, A Skeleton-Rearranged Abietane-Type Diterpenoid from Isodon rugosiformis

et al. 2022

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Rugosiformisin A, a skeleton-rearranged abietane-type diterpenoid with a spiro[4.5]decane motif, was isolated from Isodon rugosiformis. Its structure was unambiguously established via NMR spectroscopic analysis and single-crystal X-ray diffraction. A bioinspired asymmetric synthesis of rugosiformisin A was achieved in 15 steps with 2.7% overall yield. The synthesis features an iridium-catalyzed asymmetric polyene cyclization and a semipinacol rearrangement.

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Four new spiroaxane sesquiterpenes and one new rosenonolactone derivative from cultures of Basidiomycete Trametes versicolor

Cited by 12 publications

References 18 publications

Sesquiterpenoids Specially Produced by Fungi: Structures, Biological Activities, Chemical and Biosynthesis (2015–2020)

Sesquiterpenoids Specially Produced by Fungi: Structures, Biological Activities, Chemical and Biosynthesis (2015–2020)

Database on the taxonomical characterisation and potential toxigenic capacities of microorganisms used for the industrial production of food enzymes and feed additives, which do not have a recommendation for Qualified Presumption of Safety

Isolation and Bioinspired Total Synthesis of Rugosiformisin A, A Skeleton-Rearranged Abietane-Type Diterpenoid from Isodon rugosiformis

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