Fungi as a source of natural coumarins production

Costa, Tania Maria; Tavares, Lorena Benathar Ballod; Oliveira, Débora de

doi:10.1007/s00253-016-7660-z

Cited by 48 publications

(32 citation statements)

References 86 publications

(150 reference statements)

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“…Coumarins (1,2-benzopyrone or benzopyran-2-one) are heterocyclic compounds present in many plants (Angiospermas, Apiaceae, Rutaceae, and Asteraceae) (Venugopala, Rashmi, & Odhav, 2013) fungi (Agaricus sp., Armillariella tabescens, and Penicillium) (Costa, Tavares, & Oliveira, 2016), and bacteria (Streptomyces spheroides and Streptomyces niveus) (Steffensky, Mühlenweg, Wang, Li, & Heide, 2000). The isocoumarins are structurally similar to coumarins, differing only by the orientation of the lactone.…”

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confidence: 99%

Design, synthesis, molecular modelling, and in vitro evaluation of tricyclic coumarins against Trypanosoma cruzi

et al. 2018

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Chagas disease is caused by infection with the parasite protozoan Trypanosoma cruzi and affects about 8 million people in 21 countries in Latin America. The main form of treatment of this disease is still based on the use of two drugs, benznidazole and nifurtimox, which both present low cure rates in the chronic phase and often have serious side‐effects. Herein, we describe the synthesis of tricyclic coumarins that were obtained via NHC organocatalysis and evaluation of their trypanocidal activity. Molecular docking studies against trypanosomal enzyme triosephosphate isomerase (TIM) were carried out, as well as a theoretical study of the physicochemical parameters. The tricyclic coumarins were tested in vitro against the intracellular forms of Trypanosoma cruzi. Among the 18 compounds tested, 10 were more active than the reference drug benznidazole. The trypanocidal activity of the lead compound was rationalized by molecular docking study which suggested the strong interaction with the enzyme TIM by T. cruzi and therefore indicating a possible mode of action. Furthermore, the selectivity index of eight tricyclic coumarins with high anti‐T. cruzi activity was above 50 and thus showing that these lead compounds are viable candidates for further in vivo assays.

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confidence: 99%

Design, synthesis, molecular modelling, and in vitro evaluation of tricyclic coumarins against Trypanosoma cruzi

et al. 2018

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“…[15] Additionally, we proposed a plausible biosynthetic pathway of 1. The biosynthetic route starts from glucose via phenylalanine to yield umbeliferone [24] which undergoes alkylation [25,26] to obtain 1 (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…[41,42,24] These secondary metabolites have many bioactivities such as antiacetylcholinesterase, anti-bacterial, anti-cancer, anti-coagulant, anti-fungal, anthelmintic, anti-inflammatory, anti-HIV, antimicrobial, anti-oxidant and anti-viral activities. [41,42,24,43] Coumarins are utilized in wide range of applications, not only as pharmaceuticals but also as cosmetics, fragrances, agrochemicals, insecticides, in food industry and in color technol-ogy. [24,44] Additionally, coumarins have been used in pharmaceutical industry as precursors in the synthesis of anticoagulant agents since 1868.…”

Section: Resultsmentioning

confidence: 99%

“…[41,42,24,43] Coumarins are utilized in wide range of applications, not only as pharmaceuticals but also as cosmetics, fragrances, agrochemicals, insecticides, in food industry and in color technol-ogy. [24,44] Additionally, coumarins have been used in pharmaceutical industry as precursors in the synthesis of anticoagulant agents since 1868. [24] In recent years, the production of chemicals by microbial conversion is becoming an important component of industrial biotechnology.…”

Section: Resultsmentioning

confidence: 99%

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Epigenetic Manipulation Induces the Production of Coumarin‐Type Secondary Metabolite from Arthrobotrys foliicola

Hsueh

et al. 2019

Israel Journal of Chemistry

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Pursuing epigenetic manipulation approach in fungi led to the isolation of an unusual coumarin metabolite from fungi. An addition of the histone deacetylase inhibitor, suberohydroxamic acid (SBHA), to the culture medium of Arthrobotrys foliicola induced production of the coumarin‐type secondary metabolite represented by a single intensive peak in the HPLC profile of the ethyl acetate extract. The compound which was identified as 4‐ethyl‐7‐hydroxy‐8‐methyl‐2H‐chromen‐2‐one (1) was isolated from nature for the first time. Moreover, the investigation on the remaining part of the HPLC profile led to the separation of 6‐ethyl‐2,4‐dihydroxy‐3‐methylbenzaldehyde (2) and ten 2,5‐diketopiperazine compounds (3–12). The structures of isolates were deduced by their mass and NMR spectroscopic data. The coumarin‐type secondary metabolite (1) with peculiar smell induced by epigenetic stimulation is found for the first time in the Arthrobotrys species and the family Orbiliaceae. We evaluated 1 for the cytotoxic, anti‐inflammatory, anti‐allergic and nematocidal activities, however, it was found inactive.

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“…A wide range of derivatives including furan rings and pyran rings has been reported from bacteria, fungi and plants. As it regards fungi, coumarins have been up to now isolated from several species both in Ascomycota and Basidiomycota, including polypores (Costa et al 2016); nevertheless, chlorination has been reported from F. officinalis only, despite chlorinated coumarins are known in plants (Guz et al 2001;Patnam et al 2005).…”

Section: Chlorinated Coumarinsmentioning

confidence: 99%

Antimicrobial properties of Fomitopsis officinalis in the light of its bioactive metabolites: a review

Girometta

2018

Mycology

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Fomitopsis officinalis, also known as Laricifomes officinalis, is a medicinal polypore used for millennia (Agarikon) to contrast several diseases, particularly the pulmonary ones. A rich literature has dealt with its ethno-mycological aspects, but isolation and chemical characterisation of single compounds has only recently significantly developed, as well as in vitro tests for bioactivity. According to several reports there is evidence of a broad-spectrum antibacterial and antiviral activity by F. officinalis, including pathogens like Mycobacterium tuberculosis, Yersinia pseudotuberculosis and Staphylococcus aureus, as well as Ortopox virus. Chlorinated coumarins from mycelia and lanostane triterpenoids from basidiomes have been demonstrated to be directly responsible for antiviral-antibacterial and trypanocidal activity, respectively. A wider literature deals instead with crude extracts including an undetermined mixture of metabolites, whose efficacy in vitro is yet far from being standardised as extraction and treatment methodology are highly variable. Nevertheless, in vivo tests on bees provided promising results in order to develop sustainable solutions against the pathogens responsible for colony collapse disorders. Despite increasing attention has been paid to other medicinal aspects of this polypore, such as immune-tropic or antitumor, this review rationally reports and critically analyses the available knowledge by focusing on aspects of antimicrobial properties.

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Fungi as a source of natural coumarins production

Cited by 48 publications

References 86 publications

Design, synthesis, molecular modelling, and in vitro evaluation of tricyclic coumarins against Trypanosoma cruzi

Design, synthesis, molecular modelling, and in vitro evaluation of tricyclic coumarins against Trypanosoma cruzi

Epigenetic Manipulation Induces the Production of Coumarin‐Type Secondary Metabolite from Arthrobotrys foliicola

Antimicrobial properties of Fomitopsis officinalis in the light of its bioactive metabolites: a review

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