Metabolites from Penicillium sp., an endophytic fungus from the liverwort Riccardia multifida (L.) S. Gray

Recently, the metabolites separated from endophytes have attracted significant attention, as many of them have a unique structure and appealing pharmacological and biological potentials. Isocoumarins represent one of the most interesting classes of metabolites, which are coumarins isomers with a reversed lactone moiety. They are produced by plants, microbes, marine organisms, bacteria, insects, liverworts, and fungi and possessed a wide array of bioactivities. This review gives an overview of isocoumarins derivatives from endophytic fungi and their source, isolation, structural characterization, biosynthesis, and bioactivities, concentrating on the period from 2000 to 2019. Overall, 307 metabolites and more than 120 references are conferred. This is the first review on these multi-facetted metabolites from endophytic fungi.

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“…Compound 300 produced by Penicillium sp. possessed moderate inhibitory activity on the Arabidopsis thaliana seeds germination [116].…”

Section: Other Biological Activitiesmentioning

confidence: 99%

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

et al. 2020

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“…In addition to the five compounds described above, we also isolated 14 known ones ( Figure 1 ), alternariol ( 6 ; Tanahashi et al, 1997 ), alternariol 9-methyl ether ( 7 ; Meng et al, 2012 ) altenuene ( 8 ; Xiao et al, 2014 ), 3-epidihydroaltenuene A ( 9 ; Tian et al, 2016 ), 5-hydroxyepialtenuene ( 10 ; Jin et al, 2013 ), 5′-epialtenuene ( 11 ; Bradburn et al, 1994 ), 4′-epialtenuene ( 12 ; Aly et al, 2008 ) isoaltenuene ( 13 ; He et al, 2012 ), (+)-nigrosporaol A ( 14 ; He et al, 2016 ), (3a R ,9b R )-6,9b-dihydroxy-8-methoxy-1-methyl-cyclopentene[c]isochromen-3,5-dion ( 15 ; Jiao et al, 2013 ), alternatains A ( 16 ; Yang H. Y. et al, 2019 ), 2,5-dimethyl-7-hydroxychromone ( 17 ; Kashiwada et al, 2008 ), 2-(2’ S -hydroxypropyl)-5-methyl-7-hydroxychromone ( 18 ; Khamthong et al, 2012 ), 7-hydroxy-2-hydroxymethyl-5-methyl-4H-chromen-4-one ( 19 ; Kimura et al, 2008 ). All of these compounds were identified by comparing their 1 H and 13 C NMR data with those reported in the literatures.…”

Section: Resultsmentioning

confidence: 99%

Polyketides with IDH1 R132h and PTP1B inhibitory activities from the desert-plant-derived fungus Alternaria sp. HM 134

Li²,

Ma³

et al. 2022

Front. Microbiol.

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Five new polyketides named alternafurones A (1) and B (2), alternapyrones M-O (3–5), together with fourteen known ones (6–19), were isolated from the desert-plant-derived fungus Alternaria sp. HM 134. The structures of the new compounds were elucidated from spectroscopic data and ECD spectroscopic analyses. Alternafurones A and B represent polyketides with an unprecedented 6/5/6 skeleton core. Compounds 1, 2 and 4 showed definite inhibitory activities against isocitrate dehydrogenase 1 gene (IDH1 R132h) with IC50 values of 29.38, 19.41 and 14.14 μg/ml, respectively. Seven compounds (6, 7, 9–12, 14) showed potent protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC50 values ranging from 0.97 μg/ml to 89.80 μg/ml.

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“…There are only a few scientific publications on phytochemical studies of liverwort endophytes. These include the following species, Scapania ciliata , S. verrucosa , Heteroscyphus tener , Riccardia multifida , and Trichocolea tomentella [ 23 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ]. As in the case of the current research, the literature data indicate no phytochemical correlation between plant material and their endophytes.…”

Section: Discussionmentioning

confidence: 99%

Phytochemical Profile and Anticancer Potential of Endophytic Microorganisms from Liverwort Species, Marchantia polymorpha L.

2021

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Liverwort endophytes could be a source of new biologically active substances, especially when these spore-forming plants are known to produce compounds that are not found in other living organisms. Despite the significant development of plant endophytes research, there are only a few studies describing liverwort endophytic microorganisms and their metabolites. In the presented study, the analysis of the volatile compounds obtained from thallose liverwort species, Marchantia polymorpha L., and its endophytes was carried out. For this purpose, non-polar extracts of plant material and symbiotic microorganisms were obtained. The extracts were analyzed using gas chromatography coupled to mass spectrometry. Compounds with the structure of diketopiperazine in the endophyte extract were identified. Liverwort volatile extract was a rich source of cuparane-, chamigrane-, acorane-, and thujopsane-type sesquiterpenoids. The cytotoxicity of ethyl acetate extracts from endophytic microorganisms was evaluated on a panel of cancer (FaDu, HeLa, and SCC-25) cell lines and normal (VERO), and revealed significant anticancer potential towards hypopharyngeal squamous cell carcinoma and cervical adenocarcinoma.

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Metabolites from Penicillium sp., an endophytic fungus from the liverwort Riccardia multifida (L.) S. Gray

Cited by 24 publications

References 17 publications

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

Polyketides with IDH1 R132h and PTP1B inhibitory activities from the desert-plant-derived fungus Alternaria sp. HM 134

Phytochemical Profile and Anticancer Potential of Endophytic Microorganisms from Liverwort Species, Marchantia polymorpha L.

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