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ASPECTS OP SECONDARY METABOLISM IN BASIDIQMYCETES BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS A SURVEY OF PHENOL-O-METHYLTRANSFERASE IN SPECIES OF LENTINUS AND LENTINELLUS by by.' . WEI-WEI/WANG B.Sc, National Taiwan University, 1974 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE in THE FACULTY OF GRADUATE STUDIES (DEPARTMENT OF BOTANY) We accept 'this thesis as conforming to the required standard THE UNIVERSITY OF BRITISH COLUMBIA November, 1977 f7\ Wei-Wei Wang, 1977 In presenting this thesis in partial fulfilment of the requirements for an advanced degree at the University of British Columbia, I agree that the Library shall make it freely available for reference and study. I further agree that permission for extensive copying of this thesis for scholarly purposes may be granted by the Head of my Department or by his representatives. It is understood that copying or publication of this thesis for financial gain shall not be allowed without my written permission. Department of Botany The University of British Columbia 2075 Wesbrook Place Vancouver, Canada V6T 1W5 Date December 6. 1977 ii ABSTRACT I. Psilocybe cubensis was cultured successfully in two media. Medium A was devised by Catalfomo and Tyler and Medium B was a modification of a medium which has been used for ergot alkaloid production by Claviceps purpurea. Only when the fungus was kept on Sabouraud agar plates.did it subsequently produce psilocybin when transferred to liquid media. A quantitative time-course study of psilocybin production in the two media was carried out. Maximal production appeared on the fifth day. The activities of an acid phosphatase, acting on psilocybin, were measured from mycelia grown in the two media. Enzyme activity from the A culture was very high and a blue color caused by oxidation of psilocin formed in five minutes. The effect of adding L-tryptophan on alkaloid production as well as 14 the fate of tryptophan-C was also investigated. Tryptophan stimulated significantly psilocybin production in the very beginning in the B medium. The degradation of tryptophan was different in the two media. It was converted to kynurenine and anthranilic acid in A medium and to tryptamine in tryptophan added B medium (B' medium). Radioactive D,L-tryptophan side chain labeled, gave labeled psilocin and psilocybin. Potassium deficiency decreased psilocybin production while a potassium supplement had no effect. The fungus did not produce polyacetylenic compounds in the medium but ergosterol was detected as a major acetate derived metabolite when the fungus was kept on MYP agar plates and transferred subsequently to liquid media. Psilocin has very slight anti• biotic activity against Candida albicans whereas psilocybin has none. iii II. Eight species of Lentinus and Lentinellus. were investigated for the occurrence of a phenol-O-methyltransferase. Only Lentinus lepideus and Lentinus pbnderbsus showed enzyme activity in both light and dark conditions. The specificity of the enzyme for a number of substrates was also examined. Of six compounds tested, methyl p-coumarate, methyl caffeate and methyl ferulate.served-as substrates. The products of enzymic activity were identified-by radioautography. iv TABLE OF CONTENTS PAGE ABSTRACT ii TABLE OF CONTENTS;. iv LIST OF TABLES vi LIST OF FIGURES vii ACKNOWLEDGEMENT ix I. BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS INTRODUCTION 1 REVIEW OF LITERATURE 3 MATERIALS AND METHODS A. Chemicals 13 B. Medium and culture 15 C. Analytical methods 17 D. Radioautography 20 E. Psilocybin phosphatase activity 21 F. Potassium nutrition and psilocybin production 23 G. Test of UV-mediated antibiotic and phototoxic activities of medium, psilocin and psilocybin 24 EXPERIMENTAL AND RESULTS A. Chromatographic separation and identification of tryptophan metabolites 25 B. pH, Growth and morphological difference of cultures 26 C. Psilocybin production 27 D. Formation of psilocybin and psilocin from tryptophan 28 V E. Phosphatase activity 39 F. Psilocybin production and potassium nutrition 39 G. Ehrlich-positive compounds in the extracts 42 H. Tryptophan concentration in the medium 42 I. Antibiotic activity of psilocin, psilocybin and medium filtrate 49 J. Identification of d(-)mannitol 49 DISCUSSION 54 LITERATURE CITED 63 II. A SURVEY OF PHENOL-0-METHYLTRANSFERASE IN SPECIES OF LENTINUS AND LENTINELLUS INTRODUCTION 69 MAT ERI AL S A ANDI1ME THOD S A. Chemicals 73 B. Medium and culture 74 C. Extraction of enzyme 75 D. Enzyme assay 75 E. Identification of reaction products 76 F. Protein concentration 76 RESULTS AND DISCUSSION 77 LITERATURE CITED 81 vi LIST OF TABLES page I. BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS 1. Some Tryptamine Derivatives Found in Fungi 3 2. Fungi Containing Psilocybin 6 3. Composition of A-medium 15 4. Composition of B-medium 16 5. Fluorescence, Color Reaction and R^ Values of Some Tryptophan Metabolites 25 6. Distribution of Radioactivity in Tryptophan, Psilocybin and Psilocin of Mycelium Extract, 14 Administered D,L-Tryptophan, side chain-3-C 28 7. The Growth, pH of Medium and Psilocybin Production of B-medium, Potassium Deficient and Supplement Media 39 II. A SURVEY OF PHENOL-0-METHYLTRANSFERASE IN SPECIES OF LENTINUS AND LENTINELLUS 1. Substrates Specificity of Methylating Enzymes from Lentinus ponderosus and Lentinus lepideus 78 vii LIST OF FIGURES page I. BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS 1. Locations of some standard tryptophan metabolites on a two-dimensional cellulose thin layer plate 29 2. pH of A and A' media 30 3. pH of B and B' media 31 4. Growth rate of fungal cells in A and A' media 32 5. Growth rate of fungal cells in B and B' media 33 6. UV spectrum of authentic psilocybin -.34 6!. UV spectrum of psilocybin isolated from fungal cells 35 7. Psilocybin production from A and A' media 36 8. Psilocybin production from B and B' media 37 9. Radioautograph of chromatographed tryptophan metabolites of a mycelium extract of Psilocybe cubensis, administered D,L-tryptophan 38 10. Blue color formation when psilocybin incubated with enzyme extract 40 11. Activities of acid phosphatases of the mycelia from two different media 41 12. Chromatograms of mycelium extract and medium extract of different growth period 43 13. Tryptophan concentration of A' and B' media 48 14. Antibiotic activity of psilocin 50 15. IR spectrum of white crystals 51 16. NMR spectrum of acetate derivative of white crystals 53 17. UV spectrum of ergosterol 55 viii A SURVEY OF PHENOL-O-METHYLTRANSFERASE IN SPECIES OF LENTINUS AND LENTINELLUS 1. Radioautographs of the chromatographed methylated clnnamate products ix ACKNOWLEDGEMENT I wish to express my appreciation to Dr. G. H. N. Towers for his suggestion of this project and his advice, criticism and encouragement. I like to thank sincerely to Dr. C. K. Wat for her helpful assist• ance and guidance; to the members of committee in reading the manuscript and making critical comments; and.to the faculty, staff and students of the Department of Botany for being helpful in many ways. I also acknowledge with gratitude to Mr. Terry Q. F. Ching for his invaluable assistance in the preparation of the manuscript; to Miss Yvonne Tang for proofreading the final manuscript; and to Mr. H. P. Hsu for his contribution in many ways. X I, I. BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS 1 INTRODUCTION Intoxication, following the ingestion of certain kinds of mushrooms has. been known as early as the tenth century in the Sung Dynasty of China (69) and an 11th Century tale from Japan is about the eating of "dancing mushrooms" and "laughing mushrooms" (4, 69). Of the psychotropic materials utilized by ancient Nahuatl people of the New World, teonanacatl ("God's mushrooms" or "God's flesh") especially stands out in Mexican history (3). Since the pre-Columbian era, the Indians of Mexico have made the eating of certain fungi a part of their religious rites (15). The first record of the use of hallucinogenic mushrooms dates from 1502 at the Aztec Coronation festivals of Montezuma II (3, 70). This was recently rediscovered by R. G. Wasson and U. P. Wasson in 1957 (70). The active hallucinogenic principle was isolated from Psilocybe and therefore named psilocybin (4-phosphoryl-N,N-dimethyltryptamine). Psilocin is the dephosphorylated derivative. They are the first natural indole derivatives found to possess an OH group in position 4 and psilocybin is the first one known to contain a phosphate group (71). The chemical synthesis of these two indole alkaloids has been well 14 studied. The biosynthesis has only been studied by feeding C -labeled precursors and from these results a pathway has been proposed. Enzymological studies are meager. One of the objectives of the present study was to find better growth conditions for the production of psilocybin so as to lead to further studies on enzymology of biosynthesis and psychopharmaco- logy. Psilocybin has been demonstrated to be derived from tryptophan. An objective of this study concerned the fate of added tryptophan and of labeled tryptophan. 2 It was interesting to find out if there is any biological significance in the production of these two indole compounds. A brief examination of cultures for other obvious secondary metabolites, such as polyacetylenes, was also carried out. 3 REVIEW OF LITERATURE A. The occurrence of tryptamine derivatives in higher fungi Certain tryptamine derivatives (I) to which psychotomimetic, properties have been ascribed occur in a number of the Basidiomycetes (1, 2, 3, 4). Serotonin (II), N-methylserotonin (III), bufotenine (IV) bufotenine N-oxide (V), N,N-dimethyltryptamine (VI) and 5-methoxy-N,N- dimethyltryptamine (VII) have been found in either carpophores or mycelia of species of Amanita (Amanitaceae), Panaeolus, Coprinus (Coprinaceae), Boletus (I('B6>letaeeaeO) and Sarcodpn (Thelephoraceae) (Table 1) (5, 6, 7, 8, 9, 10). Table 1. Some Tryptamine Derivatives Found in Fungi Species Compound Amanita citrinaa.
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  • The Production of Psilocybin in Submerged Culture by Psilocybe Cubensis

    The Production of Psilocybin in Submerged Culture by Psilocybe Cubensis

    The Production of Psilocybin in Submerged Culture by Psilocybe cubensis PHILIP CATALF01!O' AND V. E. TYLER, JR. (Drug Plant Laboratory, College of Pharmacy, University of Washington, Seattle 5) Psychotomimetic mushrooms have long been employed as intoxicants by vari- ous native peoples. Schultes (10) describes their employment in magico-religious ceremonies by the Indians of Mexico and Central America, and extensive docu- mentation of such usage has been provided by the Wassons (14, 15) and by Heim and Wasson (6). Especially noteworthy is the occurrence of certain indole derivatives in many of the basidiomycetes to which psychotomimetic properties have been ascribed. Several species of Panaeolus contain serotonin (o-hydroxytryptamine), first demonstrated in a fungus, Panaeolus campanulatus (Fr.) Quel., by Tyler (13). Bufotenine (5-hydroxy-N,lV-dimethyltryptamine) was shown to exist in Amanita citrina (Shaeff.) S. F. Gray [Amanita mappa (Lasch) Quel.] by Wieland and Motzel (16). Psilocybin (4-phosphoryl-N,N-dimethyltryptamine), together with the closely related psilocin (4-hydroxy-1Y,N-dimethyltryptamine), was first found in Psilocybe species by Hofmann, et al. (8).The latter two principles are the most recently discovered hallucinogens in basidiomycetes and are of particular interest since they are the only principles isolated from mushrooms 'w-hichare capable of inducing psychotomimetic effects in human beings following oral ingestion. Heim, et al.(7), established conditions favoring the formation of both sclerotia and sporocarps from mycelial growth obtained upon subculture of the spores and tissue of the naturally occurring Mexican Psilocybe species. In this way they obtained ample amounts of materials for isolation and structural studies of the active principles.
  • Toxic Fungi of Western North America

    Toxic Fungi of Western North America

    Toxic Fungi of Western North America by Thomas J. Duffy, MD Published by MykoWeb (www.mykoweb.com) March, 2008 (Web) August, 2008 (PDF) 2 Toxic Fungi of Western North America Copyright © 2008 by Thomas J. Duffy & Michael G. Wood Toxic Fungi of Western North America 3 Contents Introductory Material ........................................................................................... 7 Dedication ............................................................................................................... 7 Preface .................................................................................................................... 7 Acknowledgements ................................................................................................. 7 An Introduction to Mushrooms & Mushroom Poisoning .............................. 9 Introduction and collection of specimens .............................................................. 9 General overview of mushroom poisonings ......................................................... 10 Ecology and general anatomy of fungi ................................................................ 11 Description and habitat of Amanita phalloides and Amanita ocreata .............. 14 History of Amanita ocreata and Amanita phalloides in the West ..................... 18 The classical history of Amanita phalloides and related species ....................... 20 Mushroom poisoning case registry ...................................................................... 21 “Look-Alike” mushrooms .....................................................................................