<i>Phialomyces macrosporus</i>: Chemical Constituents, Antimicrobial Activity and Complete NMR Assignments for the 7,7′‐Biphyscion

Brandão, Maurício Da Silva; Abreu, Lucas Silva; Geris, Regina

doi:10.1002/cbdv.201900353

Cited by 10 publications

(6 citation statements)

References 37 publications

(54 reference statements)

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“…Identification of compounds 4 and 5 , which were obtained as a mixture, was achieved with the help of previously isolated reference compounds [ 8 ] (SI: Figure S2). The structures of compounds 6 – 8 were confirmed via comparison with literature data as well as in-house data ( 6 : [ 18 ], 7 : [ 19 ], 8 : [ 8 , 20 ]).…”

Section: Resultsmentioning

confidence: 83%

Optimized isolation of 7,7′-biphyscion starting from Cortinarius rubrophyllus, a chemically unexplored fungal species rich in photosensitizers

Hammerle

Steger

Zhou

et al. 2021

Photochem Photobiol Sci

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Mushrooms such as the dermocyboid Cortinarius rubrophyllus are characterized by strikingly colorful fruiting bodies. The molecular dyes responsible for such colors recently experienced a comeback as photoactive compounds with remarkable photophysical and photobiological properties. One of them—7,7′-biphyscion—is a dimeric anthraquinone that showed promising anticancer effects in the low nanomolar range under blue-light irradiation. Compared to acidic anthraquinones, 7,7′-biphyscion was more efficiently taken up by cells and induced apoptosis after photoactivation. However, seasonal collection of mushrooms producing this compound, low extraction yields, and tricky fungal identification hamper further developments to the clinics. To bypass these limitations, we demonstrate here an alternative approach utilizing a precursor of 7,7′-biphyscion, i.e., the pre-anthraquinone flavomannin-6,6′-dimethyl ether, which is abundant in many species of the subgenus Dermocybe. Controlled oxidation of the crude extract significantly increased the yield of 7,7′-biphyscion by 100%, which eased the isolation process. We also present the mycochemical and photobiological characterization of the yet chemically undescribed species, i.e. C. rubrophyllus. In total, eight pigments (1–8) were isolated, including two new glycosylated anthraquinones (1 and 2). Light-dependent generation of singlet oxygen was detected for the first time for emodin-1-O-β-d-glucopyranoside (3) [photophysical measurement: Φ∆ = 0.11 (CD3OD)]. Furthermore, emodin (7) was characterized as promising compound in the photocytotoxicity assay with EC50-values in the low micromolar range under irradiation against cells of the cancer cell lines AGS, A549, and T24. Graphical abstract

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Section: Resultsmentioning

confidence: 83%

Optimized isolation of 7,7′-biphyscion starting from Cortinarius rubrophyllus, a chemically unexplored fungal species rich in photosensitizers

Hammerle

Steger

Zhou

et al. 2021

Photochem Photobiol Sci

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“…Meanwhile, in rice-grain cultures, the fungus produced the bis-anthraquinone 7,7'-biphyscion (8) and the disaccharide trehalose ( 9). [37] The polyketide flavipin (10) was exclusively isolated from Aspergillus flavipes when cultivated on a Raulin-Thom medium but not when grown on a Czapek-Dox medium, as reported by Hanson in 2000.…”

Section: Culture Media and Fungal Metabolomementioning

confidence: 55%

Exploring Culture Media Diversity to Produce Fungal Secondary Metabolites and Cyborg Cells

Geris,

Teles de Jesus,

Ferreira da Silva

et al. 2024

Chemistry & Biodiversity

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Fungi are microorganisms of significant biotechnological importance due to their ability to provide food and produce several value‐added secondary metabolites and enzymes. Its products move billions of dollars in the pharmaceutical, cosmetics, and additives sectors. These microorganisms also play a notable role in bionanotechnology, leading to the production of hybrid biological‐inorganic materials (such as cyborg cells) and the use of their enzyme complex in the biosynthesis of nanoparticles. In this sense, optimizing the fungal growth process is necessary, with selecting the cultivation medium as one of the essential factors for the microorganism to reach its maximum metabolic expression. The culture medium's composition can also impact the nanomaterial's stability and prevent the incorporation of nanoparticles into fungal cells. Therefore, our main objectives are the following: (1) compile and discuss the most commonly employed culture media for the production of fungal secondary metabolites and the formation of cyborg cells, accompanied by preparation methods; (2) provide a six‐step guide to investigating the fungal metabolomic profile and (3) discuss the main procedures of microbial cultivation to produce fungal cyborg cells.

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“…d ‐Mannitol ( 12 ) was widely found in plants, fungi, and large fruiting bodies and an important fine chemical product, food and pharmaceutical additive …”

Section: Resultsmentioning

confidence: 99%

Metabolites from Two Dominant Thermophilic Fungal Species Thermomyces lanuginosus and Scytalidium thermophilum

Yang

Zhang

Ding

et al. 2020

Chemistry & Biodiversity

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Thermomyces lanuginosus and Scytalidium thermophilum are among the most ubiquitous thermophilic fungi in compost and soil. Chemical study on these two prevalent strains collected from Yunnan led to isolation of 23 metabolites, including one new metabolite, therlanubutanolide, and 15 known compounds, isolated from the YGP culture broth of Thermomyces lanuginosus and 7 known compounds isolated from Scytalidium thermophilum, respectively. Therlanubutanolide shared the quite similar features of the same carbon skeleton and saturation as natural hexadecanoic acids. This was the first reported discovery of such a lactone as natural occurring metabolite. All the compounds were reported for the first time from thermophilic fungi. Among them, N-[(2S,3R,4E,8E)-1,3-dihydroxy-9-methyloctadeca-4,8-dien-2-yl]acetamide was for the first time reported to be a naturally occurring metabolite and its NMR data was first provided in this study. A type of PKS-derived metabolites, three 3,4-dihydronaphthalen-1(2H)-ones, which were widely found in plant pathogenic fungi as phytotoxins and reported to have antimicrobial activity, were obtained from both dominant thermophilic fungi. The frequent occurrence of such PKS phytotoxins in these two thermophilic fungi might suggest particular ecological interest.

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Phialomyces macrosporus: Chemical Constituents, Antimicrobial Activity and Complete NMR Assignments for the 7,7′‐Biphyscion

Cited by 10 publications

References 37 publications

Optimized isolation of 7,7′-biphyscion starting from Cortinarius rubrophyllus, a chemically unexplored fungal species rich in photosensitizers

Optimized isolation of 7,7′-biphyscion starting from Cortinarius rubrophyllus, a chemically unexplored fungal species rich in photosensitizers

Exploring Culture Media Diversity to Produce Fungal Secondary Metabolites and Cyborg Cells

Metabolites from Two Dominant Thermophilic Fungal Species Thermomyces lanuginosus and Scytalidium thermophilum

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