Cadinane sesquiterpenes from the mushroom Lyophyllum transforme

Clericuzio, Marco; Negri, Roberto; Cossi, Maurizio; Gilardoni, Gianluca; Gozzini, Davide; Vidari, Giovanni

doi:10.1016/j.phytochem.2013.03.019

Cited by 11 publications

(8 citation statements)

References 32 publications

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“…2 Two new pyrrolizidinone antibiotics closely related to 183 and 184, CJ-16,264 (185) and CJ-16,367 (186), were isolated from an unidentied soil fungus CL39457. 176 Recently, a novel proteasome inhibitor, pyrrolizilactone (187), was discovered from an uncharacterized fungus, 177 and inhibited the trypsin-linked activity of the proteasome. 178 All these pyrrolizidine antibiotics could be biogenetically related to tetramic acid derivatives.…”

Section: Spirotetronatesmentioning

confidence: 99%

“…[4][5][6] Cadinane sesquiterpenes have demonstrated highly selective and notable nematicidal activities, but have remained largely inactive in antimicrobial and cytotoxic assays. [185][186][187][188][189] Eremophilane sesquiterpenes, typically isolated from fungi of the genera Xylaria and Penicillium exhibit diverse biological properties, such as cytotoxic, 190,191 antimicrobial, 192 and inhibition of HIV integrase. 193 More importantly, most of the bicyclofarnesane-type sesquiterpenes are composed of an isoprenoid-derived decalin ring system linked to a polyketide ring unit with some substituted functionalized groups such as an amino acid.…”

Section: Isoprenoid Decalinmentioning

confidence: 99%

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Natural products containing ‘decalin’ motif in microorganisms

2014

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Microorganisms are well-known producers of a wide variety of bioactive compounds that are utilized not only for their primary metabolism but also for other purposes such as defense, detoxification, or communication with other micro- and macro-organisms. Natural products containing a 'decalin ring' occur often in microorganisms. They exhibit diverse and remarkable biological activities, including antifungal, antibacterial, anticancer and immunosuppressive activities, to name a few. This review surveys the natural decalin-type compounds that have been isolated from microorganisms, with emphasis on both chemical and biological implications. Total syntheses of some important decalin moiety-containing natural products are also highlighted.

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Section: Spirotetronatesmentioning

confidence: 99%

Section: Isoprenoid Decalinmentioning

confidence: 99%

Natural products containing ‘decalin’ motif in microorganisms

2014

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“…The vast majority of products of STSs in clades I and II were cadinane‐type sesquiterpenoids and δ‐cadinene was often obtained as a relatively abundant product. STSs producing cadinane‐type sesquiterpenoids have been discovered in a wide variety of basidiomycetes (Clericuzio et al, 2013 ; Ichinose et al, 2022 ; Ichinose & Kitaoka, 2018 ; Liu et al, 2007 ; Yu et al, 2022 ). Thus, combining these data and earlier literature, we suggest that the majority of basidiomycetes possess sophisticated metabolic systems to produce cadinene‐type sesquiterpenoids.…”

Section: Resultsmentioning

confidence: 99%

Biocatalyst collection and heterologous expression of sesquiterpene synthases from basidiomycetous fungi: Discovery of a novel sesquiterpene hydrocarbon

Masunaga

Kitaoka

Ichinose

2022

Microbial Biotechnology

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Basidiomycetes produce a wide variety of sesquiterpenoids, which attract significant interest in pharmaceutical and industrial applications. Structural diversification of sesquiterpenoids is performed by sesquiterpene synthases (STSs), which produce a wide array of backbone structures; therefore, functional characterization and increased biocatalyst collection of STSs are important for expanding scientific knowledge and meeting the needs of advanced biotechnology. Gene identification and functional annotation of STSs from the basidiomycetous fungi Agaricus bisporus, Auriscalpium vulgare, Lepista nuda, Pleurotus ostreatus and Trametes versicolor were conducted. Through these investigations, the catalytic functions of 30 STSs were revealed using recombinant enzymes heterologously expressed in Saccharomyces cerevisiae. Furthermore, the unique function of an STS from P. ostreatus, PoSTS-06, was revealed to be the production of a novel sesquiterpene hydrocarbon that we named pleostene. The absolute structure of pleostene was determined by NMR spectroscopy and X-ray crystallography using the crystalline sponge method.

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“…An advantage of this approach lies in the capacity to harness an expanding array of publicly available datasets. However, compared to other genera within the Agaricales, Lyophyllum exhibits a relatively limited number of species (Clericuzio et al, 2013;Wu et al, 2019). Furthermore, current community sequencing efforts may not fully represent all the basidiocarps of Lyophyllum species, implying that with increased sampling efforts, additional species are likely yet to be uncovered (Figure 5) (Hawksworth and Lücking, 2017).…”

Section: Figurementioning

confidence: 99%

Global diversity and biogeography of Lyophyllum inferred from amplicon datasets

Wei,

Qi,

Zhang

et al. 2024

Front. Ecol. Evol.

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Lyophyllum consists of rare edible and medicinal mushrooms. Considering this group’s economic and ecological significance, understanding its biodiversity could be strategically important. Our analysis involved an extensive examination of publicly available ITS sequences from NCBI-GenBank and fungal amplicon sequencing data obtained from NCBI-SRA. At a 98% sequence similarity level, we deliminated 88 Lyophyllum OTUs, 49 of which were not categorized as ‘known species’. The diversity of Lyophyllum is predominantly concentrated in the Northern Hemisphere and tends to display endemic distribution, and Europe is particularly notable for its high diversity of Lyophyllum. Given the escalating volume of data produced by amplicon sequencing, employing the amplicon dataset can facilitate an accurate survey of species diversity in Lyophyllum taxonomy. By using data from amplicon datasets, the fieldwork time and research funding for taxonomists can be saved, thereby significantly advancing the progress of the entire field of biodiversity research.

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Cadinane sesquiterpenes from the mushroom Lyophyllum transforme

Cited by 11 publications

References 32 publications

Natural products containing ‘decalin’ motif in microorganisms

Natural products containing ‘decalin’ motif in microorganisms

Biocatalyst collection and heterologous expression of sesquiterpene synthases from basidiomycetous fungi: Discovery of a novel sesquiterpene hydrocarbon

Global diversity and biogeography of Lyophyllum inferred from amplicon datasets

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