The photosensitizer emodin is concentrated in the gills of the fungus Cortinarius rubrophyllus

Siewert, Bianka; Curak, Gabrijela; Hammerle, Fabian; Huymann, Lesley; Fiala, Johannes; Peintner, Ursula

doi:10.1016/j.jphotobiol.2022.112390

Cited by 7 publications

(13 citation statements)

References 34 publications

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“…In short, we reproduced not only the results of C. rubrophyllus collected in 2019 [15], showing that the photoactivity is steadily enhanced in the gills, even in collections of different years and sites, but also significantly extended the number of photoactive dermocyboid Cortinarii. In total, the number of Cortinarius subgenus Dermocybe species investigated for their photoactivity increased to sixteen (i.e., C. cinnabarinus [6], C. cinnamomeoluteus [6], C. croceus [5], C. hadrocroceus, C. holoxanthus [14], C. huronensis, C. malicorius, C. olivaceofuscus [6], C. ominosus, C. purpureus [6], C. fervidus, C. rubrophyllus [14], C. semisanguineus [6], C. sanguineus var.…”

Section: Photochemical Testingsupporting

confidence: 75%

“…In another recent study, the photoyield of FDM (11) was determined to be φ Δ = 2% [14]. 7,7'-Biphyscion (15), in contrast, yields ten times more singlet oxygen (φ Δ = 20%), corroborating this explanation.…”

Section: Photochemical Testingmentioning

confidence: 69%

“…The most prominent difference-and probably the reason behind these diverging results-was, however, the age; the basidiocarps of the initial study [6] were sourced from an herbarium and were up to 45 years old. As a consequence, e.g., the air and light unstable pre-anthraquinones flavomannin-6,6′di-O-methyl ether (FDM) (11) and anhydroflavomannin-6,6′-di-O-methyl ether (AFDM) (14) [32,33] were nearby completely oxidized to 7,7'-biphyscion (15), the most active photosensitizer isolated from C. uliginosus. In the present study, however, freshly collected and air-dried fruiting bodies were investigated, thus the precursor FDM (11) was still present as major compound.…”

Section: Photochemical Testingmentioning

confidence: 99%

“…A larger dataset with more individual samples and consequently more data points as part of future research projects will increase the degree of freedom and thus yield true significance. Compared to the fleshy stipes, the filigree nature of gills resulted in extracts of high anthraquinone content [15]. A flaw in the DMA-assay (i.e., the extracts of the gills yield a false-positive result) is debarred by an included correction factor: the results of the DMA-quenching are corrected by the probability of the absorption; thus, solely a higher concentration of anthraquinones does not lead to a higher 1 O 2 production value [5].…”

Section: Photochemical Testingmentioning

confidence: 99%

“…Nevertheless, photoactivity is not limited to these two species of Cortinarius; it was also detected in seven other species belonging to the colorful Cortinarius subgenus Dermocybe [5,6]. The ecological function of fungal photosensitizers was explored in collections of C. rubrophyllus [15]. Photochemical and analytical studies identified emodin and its monoglucoside as responsible photosensitizers.…”

Section: Introductionmentioning

confidence: 99%

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Photochemical defense as trait of fungi from Cortinarius subgenus Dermocybe

Hannecker

Huymann

Hammerle

et al. 2022

Photochem Photobiol Sci

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The photobiological activity of ten colorful species belonging to subgenus Dermocybe of the basidiomycete genus Cortinarius was investigated. Extracts of all species produced singlet oxygen and are thus photoactive. Pigment analysis was performed and showed similarities of the anthraquinone pigments across the species in dependency to their respective pigmentation types. Detailed content analysis of the pigments in the whole agaricoid fruiting body compared to the three different tissue types (pileus, stipe, and lamellae) revealed that the pigments emodin, dermocybin, and dermorubin, as well as their respective glycosides, are enhanced in the gills. In an independent experiment, the gills were shown to be the most photoactive tissues of the fruiting body. Photobiological experiments with invertebrates (i.e., glassworm Chaoborus crystallinus) proved a phototoxic effect of the methanolic extract of the red blood webcap (Cortinarius sanguineus var. aurantiovaginatus). This work adds further evidence to a common photobiological trait in Cortinarius subgenus Dermocybe and underpins the possibility of a photochemical defense mechanism in fungi. Graphical abstract

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Section: Photochemical Testingsupporting

confidence: 75%

Section: Photochemical Testingmentioning

confidence: 69%

Section: Photochemical Testingmentioning

confidence: 99%

Section: Photochemical Testingmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Photochemical defense as trait of fungi from Cortinarius subgenus Dermocybe

Hannecker

Huymann

Hammerle

et al. 2022

Photochem Photobiol Sci

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Revised taxon definition in European Cortinarius subgenus Dermocybe based on phylogeny, chemotaxonomy, and morphology

Huymann,

Hannecker,

Giovanni

et al. 2024

Mycol Progress

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Cortinarius (Fr.) Fr. is one of the most species-rich genera in the Agaricales (Basidiomycota). Cortinarius subgen. Dermocybe (Fr.) Trog includes brightly coloured Cortinarii with anthraquinone pigments. The chemotaxonomic approach has always been as important as classical methods for species definition of Dermocybe and helped to improve overall species concepts. However, some species concepts within this group remain unclear. We therefore address this topic based on a combined phylogenetic, morphological, and pigment-chemical approach. For this, sequence data, HPLC–MS pigment profiles and spore sizes were included were included to obtain a better resolution of taxa. The study was based on 173 recent collections and 12 type specimens. A total of 117 rDNA ITS sequences were produced from the collections in this study, 102 sequences were retrieved from databases. We could detect and clearly delimit 19 Dermocybe species occurring in central European habitats, from which 16 are discussed in detail. Additionally, we grouped the detected anthraquinone pigments into four groups. This detailed analysis of dermocyboid Cortinarius species occurring in a restricted number of habitat types confirmed our hypothesis that species diversity is much higher than currently assumed. This high diversity is blurred by too wide and incorrect species concepts of several classical species like C. croceus and C. cinnamomeus. Molecular and chemotaxonomical studies carried out together with careful phenotypical analyses resulted in a good differentiation of species. A key is presented for these taxa to allow a better identification of Cortinarius subgenus Dermocybe spp. occurring in Central Europe mainly in the alpine range.

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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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The photosensitizer emodin is concentrated in the gills of the fungus Cortinarius rubrophyllus

Cited by 7 publications

References 34 publications

Photochemical defense as trait of fungi from Cortinarius subgenus Dermocybe

Photochemical defense as trait of fungi from Cortinarius subgenus Dermocybe

Revised taxon definition in European Cortinarius subgenus Dermocybe based on phylogeny, chemotaxonomy, and morphology

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

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