全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...
PLOS ONE  2013 

Evolution of the Toxins Muscarine and Psilocybin in a Family of Mushroom-Forming Fungi

DOI: 10.1371/journal.pone.0064646

Full-Text   Cite this paper   Add to My Lib

Abstract:

Mushroom-forming fungi produce a wide array of toxic alkaloids. However, evolutionary analyses aimed at exploring the evolution of muscarine, a toxin that stimulates the parasympathetic nervous system, and psilocybin, a hallucinogen, have never been performed. The known taxonomic distribution of muscarine within the Inocybaceae is limited, based only on assays of species from temperate regions of the northern hemisphere. Here, we present a review of muscarine and psilocybin assays performed on species of Inocybaceae during the last fifty years. To supplement these results, we used liquid chromatography–tandem mass spectrometry (LC–MS/MS) to determine whether muscarine was present in 30 new samples of Inocybaceae, the majority of which have not been previously assayed or that originated from either the tropics or temperate regions of the southern hemisphere. Our main objective is to test the hypothesis that the presence of muscarine is a shared ancestral feature of the Inocybaceae. In addition, we also test whether species of Inocyabceae that produce psilocybin are monophyletic. Our findings suggest otherwise. Muscarine has evolved independently on several occasions, together with several losses. We also detect at least two independent transitions of muscarine-free lineages to psilocybin-producing states. Although not ancestral for the family as a whole, muscarine is a shared derived trait for an inclusive clade containing three of the seven major lineages of Inocybaceae (the Inocybe, Nothocybe, and Pseudosperma clades), the common ancestor of which may have evolved ca. 60 million years ago. Thus, muscarine represents a conserved trait followed by several recent losses. Transitions to psilocybin from muscarine-producing ancestors occurred more recently between 10–20 million years ago after muscarine loss in two separate lineages. Statistical analyses firmly reject a single origin of muscarine-producing taxa.

References

[1]  Young A (1994) Muscarine-containing mushrooms. Spoerke DG, Rumack, BH (Eds), Handbook of mushroom poisoning: diagnosis and treatment: 289–299.
[2]  Benjamin DR (1995) Mushrooms: poisons and panaceas. New York: WH Freeman and Co.
[3]  Besl H, Mack P (1985) Halluzinogene Ri?pilze. Z Mykol 51: 183–184.
[4]  Bresinsky A, Besl H (1990) A colour atlas of poisonous fungi: A handbook for pharmacists, doctors, and biologists. London: Wolfe Publishing Ltd.
[5]  Brown J, Malone M, Stuntz D, Tyler Jr V (1962) Paper chromatographic determination of muscarine in Inocybe species. J Pharm Sci 51: 853–856.
[6]  Catalfomo P, Eugster CH (1970) Muscarine and muscarine isomers in selected Inocybe species. Helvetica Chimica Acta 53: 848–851.
[7]  Gurevich LS, Nezdoi?minogo EL (1992) Psilocybin and muscarine as possible chemotaxonomic markers for the genus Inocybe (Fr.) Fr. Mycologija i Phytopathologija 262: 88–97.
[8]  Loup C (1938) Contribution a l’étude toxicologique de trente-trois Inocybe: de la region de Genève. 141 p.
[9]  Malone M, Robichaud R, Tyler Jr V, Brady L (1962) Relative muscarinic potency of thirty Inocybe species. Lloydia 25: 231–237.
[10]  Malone M, Brady L. Relative muscarinic potency of five Inocybe species. 1987: 193–195.
[11]  Robbers JE, Brady L, Tyler Jr V (1964) A chemical and chemotaxonomic evaluation of Inocybe species. Lloydia 27: 192–202.
[12]  Stijve T (1982) Het voorkomen van muscarine en muscimol in verschillende paddestoelen. Coolia 25: 94–100.
[13]  Stijve T, Klan J, Kuyper TW (1985) Occurrence of psilocybin and baeocystin in the genus Inocybe (Fr.) Fr. Persoonia 12: 469–473.
[14]  Herrmann M (1964) Die Naumburger Massen-Pilzvergiftung mit dem Ziegelroten Ri?pilz–Inocybe patouillardii. Mykologisches Mitteilungsblatt 8: 42–44.
[15]  Yam P, Helfer S, Watling R (1993) Mushroom poisoning in a dog. Vet Rec 133: 24.
[16]  Lee S, Nam SJ, Choi R, Hyun C (2009) Mushroom Poisoning by Inocybe fastigiata in a Maltese Dog. J Anim Vet Adv 8: 708–710.
[17]  Beug MW, Shaw M, Cochran KW (2006) Thirty-plus years of mushroom poisoning: summary of the approximately 2,000 reports in the NAMA case registry. McIlvainea 16: 47–68.
[18]  Lurie Y, Wasser SP, Taha M, Shehade H, Nijim J, et al. (2009) Mushroom poisoning from species of genus Inocybe (fiber head mushroom): a case series with exact species identification. Clin Toxicol 47: 562–565.
[19]  I??lo?lu M, Helfer S, All? H, Y?lmaz F (2009) A fatal Inocybe (Fr.) Fr. poisoning in Mediterranean Turkey. Turk J Bot. 33: 71–73.
[20]  Marciniak B, Ferenc T, Kusowska J, Cie?wierz J, Kowalczyk E (2010) Poisoning with selected mushrooms with neurotropic and hallucinogenic effect. Medycyna pracy 61: 583–595.
[21]  Amitai I, Peleg O, Ariel I, Binyamini N (1982) Severe poisoning in a child by the mushroom Inocybe tristis, Malen?on and Bertault. Isr J Med Sci 18: 798–801.
[22]  Lin H (1984) Mushroom poisoning (Inocybe asterospora Quel.)–report of 3 cases. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 18: 231–233.
[23]  Griffiths RR, Richards W, McCann U, Jesse R (2006) Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. Psychopharmacology 187: 268–283.
[24]  Gartz J (1985) Vergleichende dünnschichtchromatografische Untersuchungen zweier Psilocybe-und einer halluzinogenen Inocybeart. Pharmazie 40: 134.
[25]  Gartz J (1985) Drewitz (1985) Der erste Nachweis des Vorkommens von Psilocybin in Ri?pilzen. Zeitschrift für Mykologie 51: 199–203.
[26]  Jensen N, Gartz J, Laatsch H, Biotransformations F (2006) Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens. Planta Med 72: 665–666.
[27]  Gartz J (1986) Untersuchungen zum Vorkommen des Muscarins in Inocybe aeruginascens Babos. Zeitschrift für Mykologie 52: 359–361.
[28]  Fahrig C (1920) über die Vergiftung durch Pilze aus der Gattung Inocybe (Ri?pilze und Faserk?pfe). Naunyn-Schmiedeberg’s Archives of Pharmacology 88: 227–246.
[29]  Eugster C (1957) Isolierung von Muscarin aus Inocybe Patouillardi (Bres.) 4. Mitteilung über Muscarin. Helvetica Chimica Acta 40: 886–887.
[30]  Eugster C, Müller G (1959) Notiz über weitere Vorkommen von Muscarin. 12. Mitteilung über Muscarin. Helvetica Chimica Acta 42: 1189–1190.
[31]  Semerdzieva M, Wurst M, Koza T, Gartz J (1986) Psilocybin in Fruchtk?rpern von Inocybe aeruginascens. Planta medica 47: 83–85.
[32]  Matheny PB, Aime MC, Bougher NL, Buyck B, Desjardin DE, et al. (2009) Out of the Palaeotropics? Historical biogeography and diversification of the cosmopolitan ectomycorrhizal mushroom family Inocybaceae. J Biogeogr 36: 577–592.
[33]  Kuyper TW (1986) A revision of the genus Inocybe in Europe 1. Subgenus Inosperma and the smooth-spored species of subgenus Inocybe. Persoonia 3: 1–247.
[34]  Gurevich LS, Nezdoi?minogo EL (1990) On possible application of psilocybin and muscarine alkaloids in chemotaxonomy of Inocybe (Fr) Fr. Mycologija i Phytopathologija 242: 97–105.
[35]  Maddison W, Maddison D (2010) Mesquite: a modular system for evolutionary analysis 2010. Version 2 74.
[36]  Gartz J (1986) Nachweis von Tryptaminderivaten in Pilzen der Gattungen Gerronema, Hygrocybe, Psathyrella and Inocybe: Detection of Tryptamine Derivatives in Fungi of the Genera Gerronema, Hygrocybe, Psathyrella and Inocybe. Biochemie und Physiologie der Pflanzen 181: 275–278.
[37]  Stijve T, Kuyper TW (1988) Absence of psilocybin in species of fungi previously reported to contain psilocybin and related tryptamine derivatives. Persoonia 13: 463–465.
[38]  Maddison D, Maddison W (2005) MacClade v. 4.08. Computer software distributed by Sinauer Associates Inc, Sunderland, Massachusetts.
[39]  Matheny PB, Liu YJ, Ammirati JF, Hall BD (2002) Using RPB1 sequences to improve phylogenetic inference among mushrooms (Inocybe, Agaricales). Am J Bot 89: 688–698.
[40]  Matheny PB (2005) Improving phylogenetic inference of mushrooms with RPB1 and RPB2 nucleotide sequences (Inocybe; Agaricales). Mol Phylogenet Evol. 35: 1–20.
[41]  Ryberg M, Nilsson RH, Kristiansson E, T?pel M, Jacobsson S, et al. (2008) Mining metadata from unidentified ITS sequences in GenBank: a case study in Inocybe (Basidiomycota). BMC Evo Bio 8: 50.
[42]  Alvarado P, Manjón JL, Matheny PB, Esteve-Raventós F (2010) Tubariomyces, a new genus of Inocybaceae from the Mediterranean region. Mycologia 102: 1389–1397.
[43]  Larsson E, Ryberg M, Moreau PA, Mathiesen ?D, Jacobsson S (2009) Taxonomy and evolutionary relationships within species of section Rimosae (Inocybe) based on ITS, LSU and mtSSU sequence data. Persoonia 23: 86–98.
[44]  Ryberg M, Larsson E, Jacobsson S (2010) An evolutionary perspective on morphological and ecological characters in the mushroom family Inocybaceae (Agaricomycotina, Fungi). Mol Phylogenet Evol. 55: 431–442.
[45]  Ryberg M, Matheny PB (2012) Asynchronous origins of ectomycorrhizal clades of Agaricales. P Roy Soc B Bio 279: 2003–2011.
[46]  Rambaut A, Drummond A (2007) Tracer v1. 4. Available from http://beast.bio.ed.ac.uk/Tracer.
[47]  Ryberg M, Matheny PB (2011) Dealing with incomplete taxon sampling and diversification of a large clade of mushroom-forming fungi. Evolution 65: 1862–1878.
[48]  Nylander JAA, Wilgenbusch JC, Warren DL, Swofford DL (2008) AWTY (are we there yet?): a system for graphical exploration of MCMC convergence in Bayesian phylogenetics. Bioinformatics 24: 581–583.
[49]  Schliep KP (2011) phangorn: Phylogenetic analysis in R. Bioinformatics. 27: 592–593.
[50]  Maddison WP, Slatkin M (1991) Null models for the number of evolutionary steps in a character on a phylogenetic tree. Evolution 45: 1184–1197.
[51]  Faith DP, Cranston PS (1991) Could a cladogram this short have arisen by chance alone?: on permutation tests for cladistic structure. Cladistics 7: 1–28.
[52]  Shimodaira H, Hasegawa M (1999) Multiple comparisons of log-likelihoods with applications to phylogenetic inference. Mol Biol Evol 16: 1114–1116.
[53]  Stamatakis A (2006) RAxML-VI-HPC: maximum likelihood-based phylogenetic analyses with thousands of taxa and mixed models. Bioinformatics 22: 2688–2690.
[54]  Paradis E, Claude J, Strimmer K (2004) APE: analyses of phylogenetics and evolution in R language. Bioinformatics 20: 289–290.
[55]  Lincoff GH (1981) National Audubon Society Field Guide to North American Mushrooms (National Audubon Society Field Guides). 928.
[56]  Matheny PB, Curtis JM, Hofstetter V, Aime MC, Moncalvo JM, et al. (2006) Major clades of Agaricales: a multilocus phylogenetic overview. Mycologia 98: 982–995.
[57]  Kropp BR, Albee-Scott S (2010) Inocybe tauensis, a new species from the Samoan Archipelago with biogeographic evidence for a Paleotropical origin. Fungal biol 114: 790–796.
[58]  Kropp BR, Matheny PB, Nanagyulyan SG (2010) Phylogenetic taxonomy of the Inocybe splendens group and evolution of supersection “Marginatae”. Mycologia 102: 560–573.
[59]  Jacobsson S, Larsson E (2009) Inocybe spuria, a new species in section Rimosae from boreal coniferous forests. Mycotaxon 109: 201–207.
[60]  Matheny PB, Pradeep C, Vrinda K, Varghese SP (2012) Auritella foveata, a new species of Inocybaceae (Agaricales) from tropical India. Kew Bulletin: 1–7.
[61]  Heinrich R, Wenzel B, Elsner N (2001) A role for muscarinic excitation: Control of specific singing behavior by activation of the adenylate cyclase pathway in the brain of grasshoppers. Proc Natl Acad Sci USA 98: 9919–9923.
[62]  Tissenbaum HA, Hawdon J, Perregaux M, Hotez P, Guarente L, et al. (2000) A common muscarinic pathway for diapause recovery in the distantly related nematode species Caenorhabditis elegans and Ancylostoma caninum. Proc Natl Acad Sci USA 97: 460–465.
[63]  Agurell S, Nilsson JLG (1968) Biosyntheis of psilocybin. Part II.* Incorporation of labeled tryptamine derivatives. Acta Chemica Scandinavica 22: 1210–1218.
[64]  Nitta K, Stadelmann RJ, Eugster CH (1977) Muscarine and related substances. 40. Studes on biosynthesis of muscarine in mycelial cultures of Clitocybe rivulosa. Helvetica Chimica Acta 60: 1747–1753.

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133