Library Subscription: Guest
International Journal of Medicinal Mushrooms

Published 12 issues per year

ISSN Print: 1521-9437

ISSN Online: 1940-4344

The Impact Factor measures the average number of citations received in a particular year by papers published in the journal during the two preceding years. 2017 Journal Citation Reports (Clarivate Analytics, 2018) IF: 1.2 To calculate the five year Impact Factor, citations are counted in 2017 to the previous five years and divided by the source items published in the previous five years. 2017 Journal Citation Reports (Clarivate Analytics, 2018) 5-Year IF: 1.4 The Immediacy Index is the average number of times an article is cited in the year it is published. The journal Immediacy Index indicates how quickly articles in a journal are cited. Immediacy Index: 0.3 The Eigenfactor score, developed by Jevin West and Carl Bergstrom at the University of Washington, is a rating of the total importance of a scientific journal. Journals are rated according to the number of incoming citations, with citations from highly ranked journals weighted to make a larger contribution to the eigenfactor than those from poorly ranked journals. Eigenfactor: 0.00066 The Journal Citation Indicator (JCI) is a single measurement of the field-normalized citation impact of journals in the Web of Science Core Collection across disciplines. The key words here are that the metric is normalized and cross-disciplinary. JCI: 0.34 SJR: 0.274 SNIP: 0.41 CiteScore™:: 2.8 H-Index: 37

Indexed in

Psychoactive Isoxazoles, Muscimol, and Isoxazole Derivatives from the Amanita (Agaricomycetes) Species: Review of New Trends in Synthesis, Dosage, and Biological Properties

Volume 25, Issue 9, 2023, pp. 1-10
DOI: 10.1615/IntJMedMushrooms.2023049458
Get accessDownload

ABSTRACT

Herbal products found in nature can serve as great systems of study for drug design. The Amanita muscaria mushroom is native to many parts of the Northern Hemisphere and has a very distinctive appearance with its red cap and white spotted warts. The mushroom comprises several pharmacologically active alkaloids, including muscazone, muscarine, ibotenic acid, and muscimol, the latter two compounds being potent GABA agonists. Muscimol has served as a backbone in the design of GABA agonists devoid of effects on the GABA-metabolizing enzyme, GABA transaminase, and GABA uptake systems. In this sense, several analogs of muscimol have been synthesized and studied including THIP, THPO, iso-THIP, iso-THAZ and 4-PIOL which all interact with the GABA receptors much differently. The growing pharmacological and toxicological interest based on many conflicting opinions on the use of the neuroprotective role of muscimol analogs against some neurodegenerative diseases, its potent role in the treatment of cerebral ischemia and other socially significant health conditions provided the basis for this review.

REFERENCES
  1. Johnston GAR, Chebib M, Duke RK, Fernandez SP, Hanrahan JR, Hinton T, Mewett KN. Herbal products and GABA receptors. In: Squire LR, Bloom FE, Spitzer NC, Gage F, Albright T, editors. Encyclopedia of neuroscience. 1st ed. Cambridge, MA: Academic Press; 2009. p. 1095-1101.

  2. Enz R. GABA(C) receptors: A molecular view. Biol Chem. 2001;382(8):1111-22.

  3. Enna SJ, Mohler H. The GABA receptors. Totowa, NJ: Humana Press; 2007.

  4. Bas C. Morphology and subdivision of Amanita and a monograph of its section Lepidella. Persoonia. 1969;5(4):285-573.

  5. Tulloss R. Amanita-distribution in the Americas, with comparison to eastern and southern Asia and notes on spore character variation with latitude and ecology. Mycotaxon. 2005;93:189-231.

  6. Rampolli FI, Kamler P, Carnevale Carlino C, Bedussi F. The deceptive mushroom: Accidental Amanita muscaria poisoning. Eur J Case Rep Intern Med. 2021;8(3):002212.

  7. Voynova M, Shkondrov A, Kondeva-Burdina M, Krasteva I. Toxicological and pharmacological profile of Amanita muscaria (L.) Lam. - a new rising opportunity for biomedicine. Pharmacia. 2020;67(4):317-23.

  8. Hoffman MA. Entheogens (psychedelic drugs) and the ancient mystery religions. In: Wexler P, editor. Toxicology in antiquity. San Diego, CA: Elsevier; 2019. p. 353-62.

  9. Tsujikawa K, Mohri H, Kuwayama K, Miyaguchi H, Iwata Y, Gohda A, Fukushima S, Inoue H, Kishi T. Analysis of hallucinogenic constituents in Amanita mushrooms circulated in Japan. Forensic Sci Int. 2006;164:172-8.

  10. Tsujikawa K, Kuwayama K, Miyaguchi H, Kanamori T, Iwata Y, Inoue H, Yoshida T, Kishi T. Determination of muscimol and ibotenic acid in Amanita mushrooms by high-performance liquid chromatography and liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007;852(1-2):430-5.

  11. Stormer FC, Koller GEB, Janak K. Ibotenic acid in Amanita muscaria spores and caps. Mycologist. 2004;18:114-7.

  12. Peredy T, Bradford H. Mushrooms, muscarine In: Wexler P, editor. Encyclopedia of toxicology. 3rd ed. Cambridge, MA: Academic Press; 2014. p. 416-7.

  13. Kondeva-Burdina M, Voynova M, Shkondrov A, Aluani D, Tzankova V, Krasteva I. Effects of Amanita muscaria extract on different in vitro neurotoxicity models at sub-cellular and cellular levels. Food Chem Toxicol. 2019;132(110687):110687.

  14. Ott J. Psycho-mycological studies of Amanita - from ancient sacrament to modern phobia. J Psychedelic Drugs. 1976;8(1):27-35.

  15. Krall J, Balle T, Krogsgaard-Larsen N, Sorensen TE, Krogsgaard-Larsen P, Kristiansen U, Frolund B. GABAA receptor partial agonists and antagonists: Structure, binding mode, and pharmacology. Adv Pharmacol. 2015;72:201-27.

  16. Wieczorek M. The effect of particular active substances of hallucinogenic mushrooms. Folia Biol Oecol. 2014;10(1):40-8.

  17. Vendramin A, Brvar M. Amanita muscaria and Amanita pantherina poisoning: Two syndromes. Toxicon. 2014;90:269-72.

  18. Brvar M, Mozina M, Bunc M. Prolonged psychosis after Amanita muscaria ingestion. Wien Klin Wochenschr. 2006;118(9-10):294-7.

  19. Tatsuta M, Iishi H, Baba M, Uehara H, Nakaizumi A, Taniguchi H. Protection by muscimol against gastric carcinogenesis induced by N-methyl-N-nitro-N-nitrosoguanidine in spontaneously hypertensive rats. Int J Cancer. 1992;52(6):924-7.

  20. Gagneux AR, Hafliger F, Eugster CH, Good R. Synthesis of pantherine (agarin). Tetrahedron Lett. 1965;6(25):2077-9.

  21. McCarry BE, Savard M. A facile synthesis of muscimol. Tetrahedron Lett. 1981;22(51):5153-6.

  22. Pevarello P, Varasi M. An improved synthesis of muscimol. Synth Commun. 1992;22(13):1939-48.

  23. Frey M, Jager V. Synthesis of N-substituted muscimol derivatives including N-glycylmuscimol. Synthesis. 1985;1985:1100-4.

  24. Sorensen US, Krogsgaard-Larsen P. Synthesis and synthetic utility of 3-isoxazolols. Org Prep Proced Int. 2001;33(6):515-64.

  25. Jamieson CS, Misa J, Tang Y, Billingsley JM. Biosynthesis and synthetic biology of psychoactive natural products. Chem Soc Rev. 2021;50(12):6950-7008.

  26. Obermaier S, Muller M. Ibotenic acid biosynthesis in the fly agaric is initiated by glutamate hydroxylation. Angew Chem Int Ed Engl. 2020;59(30):12432-5.

  27. Naffaa MM, Hibbs DE, Chebib M, Hanrahan JR. Roles of hydrophilic residues in GABA binding site of GABA-p1 receptor explain the addition/inhibition effects of competitive ligands. Neurochem Int. 2022;153:105258.

  28. Mortensen M, Krall J, Kongstad KT, Brygger BM, Lenzi O, Francotte P, Sorensen T, Nielsen B, Jensen A, Smart T, Frolund B. Developing new 4-PIOL and 4-PHP analogues for photoinactivation of Y-aminobutyric acid type A receptors. ACS Chem Neurosci. 2019;10(11):4669-84.

  29. Nasir M, Trujillo D, Levine J, Dwyer JB, Rupp ZW, Bloch MH. Glutamate systems in DSM-5 anxiety disorders: Their role and a review of glutamate and GABA psychopharmacology. Front Psychiatry. 2020;11:548505.

  30. Meera P, Uusi-Oukari M, Wallner M, Lipshutz GS. Guanidinoacetate (GAA) is a potent GABAA receptor GABA mimetic: Implications for neurological disease pathology. J Neurochem. 2023;165(3):445-54.

Begell Digital Portal Begell Digital Library eBooks Journals References & Proceedings Research Collections Prices and Subscription Policies Begell House Contact Us Language English 中文 Русский Português German French Spain