Endophytic fungus <i>Pseudofusicoccum stromaticum</i> produces cyclopeptides and plant-related bioactive rotenoids

Sobreira, Aline C. M.; Pinto, Francisco das Chagas L.; Florêncio, Katharine Gurgel Dias; Wilke, Diego Veras; Staats, Charley Christian; Streit, Rodrigo de A. S.; Freire, Francisco das Chagas de O.; Pessoa, Otília Deusdênia Loiola; Trindade-Silva, Amaro E.; Canuto, Kirley Marques

doi:10.1039/c8ra06824k

Cited by 15 publications

(8 citation statements)

References 59 publications

(77 reference statements)

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“…The two rotenoids rotenolone and tephrosin (Figure 1), previously reported in plants belonging to the genera Derris and Tephrosia, were found to be produced by the endophytic fungus Pseudofusicoccum stromaticum isolated from the timber tree Myracrodruon urundeuva [79]. In plants, rotenoids are formed from flavonoids in a multi-step pathway where chalcone isomerase (CHI) and CHS play a role as key enzymes [98].…”

Section: Rotenoids: Rotenolone and Tephrosinmentioning

confidence: 86%

“…During the investigation of the P. stromaticum genome, the gene encoding for a CHI-like protein was identified, elucidating the ability of this fungus to produce plant-related rotenoids, while no CHS homologue could be found. Protein alignment analysis and maximum likelihood phylogenetic reconstruction analysis have revealed that fungal CHI-like enzymes have more than one substrate specificities since they recognize chalconoids other than (2S)-naringenin [79].…”

Section: Rotenoids: Rotenolone and Tephrosinmentioning

confidence: 99%

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Using Next-Generation Sequencing Technology to Explore Genetic Pathways in Endophytic Fungi in the Syntheses of Plant Bioactive Metabolites

2022

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Recent investigations carried out all over the world have disclosed the capacity of a multitude of endophytic fungal species/strains to produce bioactive compounds which are the same or structurally related to those synthesized by their host plants. This intriguing phenomenon has implemented huge research activity aimed at ascertaining the nature of the biological processes underlying this convergence, as well as to characterize the genetic bases of the biosynthetic schemes. Insights on these basic issues may support the biotechnological exploitation of wild strains, and their eventual improvement through genome editing. Aspects concerning the use of next generation sequencing technologies for the comparative elucidation of the biosynthetic pathways operating in endophytic fungi and their host plants are reviewed in this paper in view of applicative perspectives. Our literature search yielded 21 references dealing with at least 26 strains which have been the subject of experimental activities involving massively parallel genome and transcriptome sequencing methods in the last eight years.

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Section: Rotenoids: Rotenolone and Tephrosinmentioning

confidence: 86%

Section: Rotenoids: Rotenolone and Tephrosinmentioning

confidence: 99%

Using Next-Generation Sequencing Technology to Explore Genetic Pathways in Endophytic Fungi in the Syntheses of Plant Bioactive Metabolites

2022

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“…New coumarins showing antifungal and anticholinesterase activity were isolated [10]. In another study, eleven compounds were identified and one compound, tephrosin, showed activity against a colorectal cancer cell line (HCT-116) [11].…”

Section: Introductionmentioning

confidence: 99%

Paecilins Q and R: Antifungal Chromanones Produced by the Endophytic Fungus Pseudofusicoccum stromaticum CMRP4328

et al. 2023

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Chemical investigation of the endophyte Pseudofusicoccum stromaticum CMRP4328 isolated from the medicinal plant Stryphnodendron adstringens yielded ten compounds, including two new dihydrochromones, paecilins Q (1) and R (2). The antifungal activity of the isolated metabolites was assessed against an important citrus pathogen, Phyllosticta citricarpa. Cytochalasin H (6) (78.3 %), phomoxanthone A (3) (70.2%), phomoxanthone B (4) (63.1 %) and paecilin Q (1) (50.5 %) decreased in vitro the number of pycnidia produced by P. citricarpa, which are responsible for the disease dissemination in orchards. In addition, compounds 3 and 6 inhibited the development of citrus black spot (CBS) symptoms in citrus fruits. Cytochalasin H (6) and one of the new compounds, paecilin Q (1) appear particularly promising, as they showed strong activity against this citrus pathogen, and low or no cytotoxic activity. The strain CMRP4328 of P. stromaticum and its metabolites deserve further investigation for the control of citrus black spot disease.

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“…Almost twenty years ago, Gensheimer and Musheigan discovered that the CHIdomain-containing protein family extends into fungi, slime molds, and γ-proteobacteria (8). Previous studies mention the presence of a fungal CHI-domain-containing protein family (6,(9)(10)(11)(12)(13) and speculate whether these proteins have CHI activity; however, to date, no functional characterization of the fungal CHI-domain-containing proteins has been reported.…”

Section: Introductionmentioning

confidence: 99%

Aim18p and Aim46p are CHI-domain-containing mitochondrial hemoproteins inSaccharomyces cerevisiae

Schmitz

Wolters

Murray

et al. 2022

Preprint

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Chalcone isomerases (CHIs) have well-established roles in the biosynthesis of plant flavonoid metabolites. Saccharomyces cerevisiae possesses two predicted CHI-like proteins, Aim18p (encoded by YHR198C) and Aim46p (YHR199C), but it lacks other enzymes of the flavonoid pathway, suggesting that Aim18p and Aim46p employ the CHI fold for distinct purposes. Here, we demonstrate that Aim18p and Aim46p reside on the mitochondrial inner membrane and adopt CHI folds, but they lack select active site residues and possess an extra fungal-specific loop. Consistent with these differences, Aim18p and Aim46p lack chalcone isomerase activity and also the fatty acid-binding capabilities of other CHI-like proteins, but instead bind heme. We further show that diverse fungal homologs also bind heme and that Aim18p and Aim46p possess structural homology to a bacterial hemoprotein. Collectively, our work reveals a distinct function and cellular localization for two CHI-like proteins, introduces a new variation of a hemoprotein fold, and suggests that ancestral CHI-like proteins were hemoproteins.

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Endophytic fungus Pseudofusicoccum stromaticum produces cyclopeptides and plant-related bioactive rotenoids

Abstract: Pseudofusicoccum stromaticum produces cyclopeptides and plant-related rotenoids, which are responsible for its antiproliferative effect.

Cited by 15 publications

References 59 publications

Using Next-Generation Sequencing Technology to Explore Genetic Pathways in Endophytic Fungi in the Syntheses of Plant Bioactive Metabolites

Using Next-Generation Sequencing Technology to Explore Genetic Pathways in Endophytic Fungi in the Syntheses of Plant Bioactive Metabolites

Paecilins Q and R: Antifungal Chromanones Produced by the Endophytic Fungus Pseudofusicoccum stromaticum CMRP4328

Aim18p and Aim46p are CHI-domain-containing mitochondrial hemoproteins inSaccharomyces cerevisiae

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