A convenient workflow to spot photosensitizers revealed photo-activity in basidiomycetes

Siewert, Bianka; Vrabl, Pamela; Hammerle, Fabian; Bingger, Isabella; Stuppner, Hermann

doi:10.1039/c8ra10181g

Cited by 20 publications

(55 citation statements)

References 32 publications

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“…Just recently, we started to explore this coincidence [111] and were thereby able to show a common photoactivity scheme in this subgenus. Furthermore, we were also able to isolate and to describe new AQ-like PSs from Cortinarius i.a.…”

Section: Anthraquinones and Perylene Quinonesmentioning

confidence: 99%

“…To explore this new field, the pigment classes of fungi should be systematically studied to verify the expected and to validate the assumed. Screening protocols exist [111,144], though adjustments are needed, as one part of a current method depends on an anthracene-like compound (i.e., dimethyl anthracene (DMA)) as the singlet oxygen scavenger. In consequence, this assay works well for pigments absorbing wavelength above 450 nm, but it is not suited for the UV-A range or high energetic blue light, as the probe itself absorbs light in this range.…”

Section: Outlook-ideas and Thoughts For Future Experimentsmentioning

confidence: 99%

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Does the chemistry of fungal pigments demand the existence of photoactivated defense strategies in basidiomycetes?

Siewert

2021

Photochem Photobiol Sci

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The well-known photosensitizers hypericin, harmane, and emodin are typical pigments of certain mushroom species—is this a coincidence or an indication towards a photoactivated defense mechanism in the phylum Basidiomycota? This perspective article explores this hypothesis by cross-linking the chemistry of fungal pigments with structural requirements from known photosensitizers and insights from photoactivated strategies in the kingdom Plantae. Thereby, light is shed on a yet unexplored playground dealing with ecological questions, photopharmaceutical opportunities, and biotechnological potentials.

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Section: Anthraquinones and Perylene Quinonesmentioning

confidence: 99%

Section: Outlook-ideas and Thoughts For Future Experimentsmentioning

confidence: 99%

Does the chemistry of fungal pigments demand the existence of photoactivated defense strategies in basidiomycetes?

Siewert

2021

Photochem Photobiol Sci

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“…Co-factors, which can influence the antimicrobial activity of a secondary metabolite, might be metals (Lachowicz et al, 2020), pH-conditions (Lee et al, 1997; Wiegand et al, 2015), or just a spark of light (Wozniak and Grinholc, 2018; Dos Santos et al, 2019). Such light-activated defense strategies (Downum, 1992; Flors and Nonell, 2006) are well-known for members of the kingdom Plantae and were recently suggested to be also present in fungi (Siewert and Stuppner, 2019; Siewert et al, 2019; Siewert, 2021). Furthermore, light-activated natural compounds are promising pharmaceuticals (Hudson and Towers, 1991; Berenbaum, 1995; Siewert and Stuppner, 2019).…”

Section: Introductionmentioning

confidence: 99%

“…As part of a putative light-activated defense system, the first photosensitizers, i.e. light-activated chemical compounds, were recently activity-guided discovered in fruiting bodies of macromycota (Siewert et al, 2019; Hammerle et al, 2020). Light-activated antimicrobial effects of basidiomycetes are, however, not described yet, despite promising hints (Siewert, 2021).…”

Section: Introductionmentioning

confidence: 99%

A new High-Throughput-Screening-assay for Photoantimicrobials Based on EUCAST Revealed Photoantimicrobials in Cortinariaceae

Fiala

Schoebel

Vrabl

et al. 2021

Preprint

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A spark of light might unravel antimicrobial activity of colored compounds, which otherwise would have been classified as inactive. While many mushrooms contain such colorful pigments but lack antimicrobial activity, we wondered if a controlled irradiation is needed to unleash their effect. To explore such photoantimicrobial actions in the Kingdom Fungi, an efficient high-throughput-screening (HTS) assay is needed. Here we report on the establishment of a reliable photoantimicrobial assay based on the EUCAST recommendations, which was validated with known photosensitzers (i.e., curcumin, phenalenone, rose bengal, an hypericum extract, and methylene blue). Furthermore, an improved LED-irradiation setup enabling with only 24 LEDs a homogenous irradiation of a 96-well plate is presented. The established HTS-assay was utilized to screen six colorful Cortinarius extracts unrevealing C. xanthophyllus and C. rufo-olivaceus as promising sources for new photoantimicrobials.

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“…However, because the exact phylogeny of dermocyboid Cortinarii is not revealed 23,26 , we selected representatives based on the pigment pattern. In sum, seven species being representatives of the four sections and four pigmentation types were selected (Table 1) and submitted to the photo-activity workflow 17 consisting of an HPLC-DAD-MS fingerprint analysis, a singlet-oxygen detection assay (i.e., DMA-Assay), and a (photo)cytotoxicity screening.…”

Section: Introductionmentioning

confidence: 99%

Targeted Isolation of Photoactive Pigments from Mushrooms Yielded a Highly Potent New Photosensitizer: 7,7’-Biphyscion

Hammerle¹,

Bingger²,

Pannwitz³

et al. 2021

Preprint

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<a>Pigments of mushrooms are a fertile ground of inspiration: they spread across various chemical backbones, absorption ranges, and bioactivities. While looking from a photochemical perspective, we discovered a new bioactivity, i.e., photoactivity. We revealed that singlet oxygen production is a common theme in one group of webcaps (i.e., dermocyboid Cortinarii, formerly called Dermocybe). This photoactivity was explored by bioactivity-based molecular networking and photo-activity guided isolation. As a result, three photosensitizers based on anthraquinone structures were isolated. All three were photochemically characterized and (photo)cytotoxically tested. For one of the three, i.e. (-)-7,7’-biphyscion (1), a promising photoyield of </a>fD= 20 % (lexc = 455 nm) and an excellent photocytotoxicity of approx. 64 nM against A549 lung cancer cell lines (lexc = 468 nm, 9.3 J/cm²) was found, while no effect was observed in the dark. Several molecular biological methods proved the harmlessness of 1 in the dark while showing that apoptosis is dose-dependent induced by 1 under irradiation. Therewith, 1 is a promising candidate for photodynamic therapy, while the photoactivity theme in the subgenus hints towards a yet unthought bioactivity in fungi: photoactivated defense.

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A convenient workflow to spot photosensitizers revealed photo-activity in basidiomycetes

Abstract: An expedient approach to spot natural photosensitizers was established and with it were – for the first time – photosensitizers in mushrooms identified.

Cited by 20 publications

References 32 publications

Does the chemistry of fungal pigments demand the existence of photoactivated defense strategies in basidiomycetes?

Does the chemistry of fungal pigments demand the existence of photoactivated defense strategies in basidiomycetes?

A new High-Throughput-Screening-assay for Photoantimicrobials Based on EUCAST Revealed Photoantimicrobials in Cortinariaceae

Targeted Isolation of Photoactive Pigments from Mushrooms Yielded a Highly Potent New Photosensitizer: 7,7’-Biphyscion

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