Rhodocollybia maculata explained

Rhodocollybia maculata, commonly known as the spotted toughshank, is a species of basidiomycete fungus in the family Omphalotaceae.[1] It often appears in decomposing conifer duff.[2] R. maculata is a source of collybolide, a sesquiterpenoid containing a furyl-ẟ-lactone motif reminiscent of salvinorin A.[3]

Description

The cap is cream-colored with red-brown spots. The edge remains inrolled for an extended period of time. The whitish gills are crowded, becoming spotted in age. The similarly colored stipe is long, tough, hollow, and tapered downwards.

A variety known as scorzonerea is characterized by yellowish color of its gills, and sometimes the stipe.

Edibility

Though non-toxic,[4] this species is considered inedible due to its toughness and unpalatability;[5] it is typically bitter.[6]

Kappa-opioid receptor agonism

See main article: Collybolide. In 2016, Gupta et al. reported that collybolide exhibited high-potency, selective kappa-opioid receptor (KOR) agonism.[7] Due to its attractive bioactivity and chemical similarity to salvinorin A, collybolide garnered attention in the synthetic chemistry and pharmacology fields as a potential scaffold for developing next-generation analgesics, antipruritics, and antidepressants.[8] [9]

In 2022, Shevick et al. completed the first enantioselective total synthesis of collybolide and profiled the activity of synthetic collybolide at the KOR. Despite previous findings by Gupta et al., these assays showed that neither enantiomer of collybolide had KOR activity.[10] The synthetic sample was identical to natural collybolide isolated from R. maculata. Assays of crude R. maculata extracts by other groups additionally showed no KOR activity. These assays of synthetic and natural samples contradict the findings of Gupta et al., and suggest that collybolide and the other constituents of R. maculata have no activity at KOR.

External links

Notes and References

  1. Web site: Kuo M . March 2018 . Rhodocollybia maculata . MushroomExpert.Com .
  2. Book: Trudell S, Ammirati J . Mushrooms of the Pacific Northwest . Timber Press . 2009 . 978-0-88192-935-5 . Timber Press Field Guides . Portland, OR . 120.
  3. Bui AM, Cavé A, Janot MM, Parello J, Potier P, Scheidegger U . 1974-01-01 . Isolement et analyse structurale du collybolide, nouveau sesquiterpene extrait de Collybia maculata alb. et sch. ex fries (basidiomycetes) . Isolation and structural analysis of collybolide, a new sesquiterpene extracted from Collybia maculata alb. and sch. ex fries (basidiomycetes) . Tetrahedron . fr . 30 . 11 . 1327–1336 . 10.1016/S0040-4020(01)97243-6 . 0040-4020.
  4. Book: Miller Jr OK, Miller HH . North American Mushrooms: A Field Guide to Edible and Inedible Fungi . . 2006 . 978-0-7627-3109-1 . Guilford, CN . 176 . Orson K. Miller Jr..
  5. Book: Phillips R . Mushrooms and Other Fungi of North America . Firefly Books . 2010 . 978-1-55407-651-2 . Buffalo, NY . 73 . registration.
  6. Web site: Wood M, Stevens F . The Fungi of California . Rhodocollybia maculata .
  7. Gupta A, Gomes I, Bobeck EN, Fakira AK, Massaro NP, Sharma I, Cavé A, Hamm HE, Parello J, Devi LA . 6 . Collybolide is a novel biased agonist of κ-opioid receptors with potent antipruritic activity . Proceedings of the National Academy of Sciences of the United States of America . 113 . 21 . 6041–6046 . May 2016 . 27162327 . 4889365 . 10.1073/pnas.1521825113 . 2016PNAS..113.6041G . free .
  8. Khan MI, Sawyer BJ, Akins NS, Le HV . A systematic review on the kappa opioid receptor and its ligands: New directions for the treatment of pain, anxiety, depression, and drug abuse . European Journal of Medicinal Chemistry . 243 . 114785 . December 2022 . 36179400 . 10.1016/j.ejmech.2022.114785 . 252476850 .
  9. Chakraborty S, Majumdar S . Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide . Biochemistry . 60 . 18 . 1381–1400 . May 2021 . 32930582 . 7982354 . 10.1021/acs.biochem.0c00629 .
  10. Shevick SL, Freeman SM, Tong G, Russo RJ, Bohn LM, Shenvi RA . Asymmetric Syntheses of (+)- and (-)-Collybolide Enable Reevaluation of kappa-Opioid Receptor Agonism . ACS Central Science . 8 . 7 . 948–954 . July 2022 . 35912357 . 9335922 . 10.1021/acscentsci.2c00442 .

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