Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63

Gubiani, Juliana R.; Oliveira, Michele C.S.; Neponuceno, Ricardo A.R.; Camargo, Maria José de; Garcez, Walmir Silva; Biz, Andressa R.; Soares, Marcos Antônio; Araújo, Ângela R.; Bolzani, Vanderlan S.; Lisboa, Helen Cristina Fávero; Sousa, Paulo Teixeira de; Vasconcelos, Leonardo Gomes de; Ribeiro, Tereza Auxiliadora Nascimento; Oliveira, Juliana Magalhães de; Banzato, Thais Petrochelli; Lima, Carolina A. de; Longato, Giovanna Barbarini; Batista, João M.; Berlinck, Roberto G. S.; Teles, Helder Lopes

doi:10.1016/j.phytol.2019.06.003

Cited by 29 publications

(18 citation statements)

References 19 publications

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“…Figure 2 shows the structures of uncommon indole alkaloids. Giluterrin ( 24 ), a prenylated indole alkaloid that presented an unprecedented carbon skeleton, was isolated from endophytic fungus Aspergillus terreus and presented an antiproliferative profile for prostate (PC-3) and kidney (786-0) cancer cell lines [ 29 ]. Another rare prenylated indole alkaloid is penioxamide A ( 25 ), possessing a piperidine moiety and bearing an antirelative configuration in the bicyclo[2.2.2]diazaoctane ring, and was isolated from Penicillium oxalicum and showed potent brine-shrimp lethality with LD 50 value of 5.6 μM [ 30 ].…”

Section: Resultsmentioning

confidence: 99%

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

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Torres-Mendoza

et al. 2021

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Among microorganisms, endophytic fungi are the least studied, but they have attracted attention due to their high biological diversity and ability to produce novel and bioactive secondary metabolites to protect their host plant against biotic and abiotic stress. These compounds belong to different structural classes, such as alkaloids, peptides, terpenoids, polyketides, and steroids, which could present significant biological activities that are useful for pharmacological or medical applications. Recent reviews on endophytic fungi have mainly focused on the production of novel bioactive compounds. Here, we focus on compounds produced by endophytic fungi, reported with uncommon bioactive structures, establishing the neighbor net and diversity of endophytic fungi. The review includes compounds published from January 2015 to December 2020 that were catalogued as unprecedented, rare, uncommon, or possessing novel structural skeletons from more than 39 different genera, with Aspergillus and Penicillium being the most mentioned. They were reported as displaying cytotoxic, antitumor, antimicrobial, antiviral, or anti-inflammatory activity. The solid culture, using rice as a carbon source, was the most common medium utilized in the fermentation process when this type of compound was isolated.

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Section: Resultsmentioning

confidence: 99%

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Ortega

Torres-Mendoza

et al. 2021

JoF

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“…Ellagitannins, including corilagin (4), have demonstrated a therapeutic potential to manage type-2 diabetes by in vitro and in vivo models (Caldeira et al 2020). The complete characterization of giluterrin ( 6), a cytotoxic prenylated indole alkaloid with an unprecedented carbon skeleton, produced by Aspergillus terreus P63, collected from roots of the grass Axonopus leptostachyus, reinforced the power of VCD to discriminate diastereoisomers arising from a rotated chiral axis in the presence of additional chiral centers (Gubiani et al 2019). Two groups of atropodiastereomers were considered for VCD calculations (B3LYP/6-31G(d)).…”

Section: Applications Of Vcd In Brazilmentioning

confidence: 98%

“…5 arises from vibrational modes involving predominantly the chiral centers, while the region above 1400 cm − 1 reflects the configuration of the atropoisomeric portion of the molecule. From a therapeutic point of view, giluterrin (6) presented antiproliferative profiles against prostate (PC-3) and kidney (786-0) cancer cell lines (Gubiani et al 2019).…”

Section: Applications Of Vcd In Brazilmentioning

confidence: 99%

Vibrational Circular Dichroism for the Assignment of Absolute Configuration of Natural Products in Brazil

Batista

Valverde

Batista

2021

Rev. Bras. Farmacogn.

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The determination of the absolute configuration of chiral bioactive natural products is a crucial step in their structural characterization. Several well-established techniques, such as X-ray crystallography, stereo-controlled organic synthesis, NMR, and chiroptical spectroscopy, are commonly used to this end. However, even today, the configurational analysis of natural products remains a challenge, with a significant number of reassignments being reported every year. Among chiroptical methods, vibrational circular dichroism (VCD) has emerged as an excellent tool for the assignment of the absolute configuration of structurally diverse chiral natural products directly in solution. This review covers the use of VCD spectroscopy to elucidate the absolute stereochemistry of natural products in Brazil over the last 20 years. Although the number of VCD investigations on secondary metabolites has increased, VCD can still be considered under-explored in Brazil. Therefore, herein, we aim to demonstrate the unparalleled stereochemical discriminatory power of VCD to assign both conformation and absolute configuration of natural products in conditions not commonly accessible to other techniques.

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“…From the culture of the fungus A. terreus P63, endophyte of the grass Axonopus leptostachyus , was isolated the prenylated indole alkaloid, giluterrin, with an unprecedented carbon skeleton, which showed an antiproliferative effect on prostate (PC-3) and kidney (786-0) cancer cell lines [ 178 ].…”

Section: Studies Of Fungal Secondary Metabolites As Cytotoxic and Ant...mentioning

confidence: 99%

Overview of Bioactive Fungal Secondary Metabolites: Cytotoxic and Antimicrobial Compounds

et al. 2022

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Microorganisms are known as important sources of natural compounds that have been studied and applied for different purposes in distinct areas. Specifically, in the pharmaceutical area, fungi have been explored mainly as sources of antibiotics, antiviral, anti-inflammatory, enzyme inhibitors, hypercholesteremic, antineoplastic/antitumor, immunomodulators, and immunosuppressants agents. However, historically, the high demand for new antimicrobial and antitumor agents has not been sufficiently attended by the drug discovery process, highlighting the relevance of intensifying studies to reach sustainable employment of the huge world biodiversity, including the microorganisms. Therefore, this review describes the main approaches and tools applied in the search for bioactive secondary metabolites, as well as presents several examples of compounds produced by different fungi species with proven pharmacological effects and additional examples of fungal cytotoxic and antimicrobial molecules. The review does not cover all fungal secondary metabolites already described; however, it presents some reports that can be useful at any phase of the drug discovery process, mainly for pharmaceutical applications.

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Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63

Cited by 29 publications

References 19 publications

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Vibrational Circular Dichroism for the Assignment of Absolute Configuration of Natural Products in Brazil

Overview of Bioactive Fungal Secondary Metabolites: Cytotoxic and Antimicrobial Compounds

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