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The Occurrence of Psilocybin and Psilocin in Finnish Fungi

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The Occurrence of Psilocybin and Psilocin in Finnish Fungi Journal of Natural Products 74I Vol. 50, NO.4, pp. 741-744,Jul-A~g 1987 THE OCCURRENCE OF PSILOCYBIN AND PSILOCIN IN FINNISH FUNGI E. OHENOJA,~ Botanical Museum, University of Ouh, SF-90570 Oulu, Finland J. JOKIRANTA, Department of Pharmacology and Toxicology, University ofKuopio, SF-7021 1 Kuopio, Finland T. MAKINEN, Department of Pharmacology and Toxicology, University of Kuopio, SF-7021 I Kuopio, Finland A. KAIKKONEN, Botanical Museum, University of Oulu, SF-90570 Oulu, Finland and M.M. AIRAKSINEN Department of Pharmacology and Toxicology, Uniwrsity of Kuopio, SF-7021 I Kuopio, Finland The use of hallucinogenic fungi con- involved about 450 analyses. Most of the fungi taining psilocybin and or psilocin (1) studied belong to the order Agaricales, and three has, during the past few decades, spread species belong to the order Boletales. The fungal material was collected mainly in the autumn of from Central America to the whole west- 1983. Some older samples were also analyzed, be- ern world (2-4). Psilocybin (4-phos- cause not all the desired species were found dur- phoryloxy-N, N-dimethyltryptamine) ing the season. A series of specimens of P. semilan- and psilocin (4-hydroxy-N,N-dimethyl- ceata collected in the years 1843, 1869, 1954, tryptamine) were first isolated from and 1976 was analyzed in order to test the stabil- ity ofpsilocybin and psilocin in the fruiting body. Psilocybe mexicana (5) but have later been The analyses were performed on fresh, deep- reported from more than 30 species of frozen, or dried material. The identification was, the genus and from several species of in some cases, made in the field with the aid of other genera. fresh characteristics, but several species were also In the Scandinavian countries, the determined microscopically. Some species were identified or confirmed by outside specialists. most common psilocybin-containing Parts of the samples analyzed are preserved in the fungus is Psilocybe semilancuta (6,7);in herbarium of the University of Oulu (Herb. all, about ten active species have been re- OULU). ported from Norway and Denmark The fresh samples (each about 500 mg) were (8,9).In this study, a variety of Finnish frozen right after harvesting until analysis. They were ground in an homogenizer (Ultra-Turrax) fungi were screened for their psilocybin with 2 ml of MeOH; whereafter 5 ml of MeOH and psilocin content using two methods was added, and the mixture was agitated for 60 of hplc (10,ll). min. The dry samples, including the herbarium MATERIALS AND METHODS specimens, were dried overnight at 45", ground into powder, weighed, and shaken for 60 min The fungus specimens were collected for analy- with 7 ml of MeOH. Both samples were then cen- sis from different parts of the country, most of trifuged for 15 min (3000 rpm). The supernatant them, however, from eastern and northern Fin- (5 ml) was stored at -70' until analysis. land. A few specimens from Denmark, Scotland, The hplc-system used (excluding the station- and Germany were also analyzed. The material ary and mobile phases) has been described in an was collected partly randomly, but an emphasis earlier publication (7). The stationary phase con- was placed on the fungi that are assumed to be sisted of a prepacked FBondapak RP-C 18 col- hallucinogenic on the basis of the literature, and, umn (Waters, Milford, Mass.). All the samples in addition, on blue species and species that turn were screened with method A, and the positive blue or black. and suspected ones were reanalyzed with method A total of 61 species belonging to 30 genera B. In method A the mobile phase consisted of were analyzed, and the whole screening procedure MeOH-H,O (60:40), and the paired ion 742 Journal of Natural Products Wol. 50, No. 4 TABLE1. Psilocybin and Psilocin Contents (% of w< ht) Found in the Studied F\ gus Species Number of (dry)or positive psilocybin psilocin Species (fresh) /studied specimen (%) (%) specimen Pluteus atricapilluP ........... 215 d 0.004 - d 0.005 - Pluteus salicinus" ............ 212 d 0.21 - d 0.30 0.05 PanaeoIus oIivareusb ........... 113 f 0.005 - Panaeulus subbaItutusb ......... 414 d 0.11 0.004 f 0.01 - d 0.06 - d 0.14 - Panaeolina fwtisecii .......... 2/ 19 d 0.03 - d 0.03 - Psathyrella candolluna ......... 117 d 0.004 0.005 Conqbe ryanopus' ........... 11 1 f 0.45 0.07 Conocybe kuehneriana' .......... I/ 1 d - 0.004 PsiIqbe semilanceatad ......... 515 f 0.80 0.003 f 0.19 0.004 d 0.87 - f 0.82 0.025 d 0.20 - Agrqbe' sp. ............. 1/ 1 d 0.003 - Herbarium specimens of Psilorybe semilancuta Collecting Year 1843 -11 d - - 1869 1/ 1 d 0.014 - 1954 11 1 d 0.67 - 1976 1/ 1 d 0.84 - "Identification confirmed by E. Vellinga. bIdentified or confirmed by E. Gerhardt. 'Identified or confirmed by R. Watling. dIdentified or confirmed by G. Guzman and E. Rald. chromatography (pic) reagent was heptanesul- weight) of psilocybin were detected in fonic acid buffered to pH 3.5 with HOAc (10). In Conocybe cyanopus (Atk.) Kiihn. and method B the mobile phase consisted of MeOH- H,O-cetrimoniumbromide (40:60:0.15, v/v/w). Psilocybe semilanceata (Fr .) Kumm . , and The buffer was 0.25% Na2HPO4+O. 15% fairly high ones in Pluteus salicinus (Pers. NaH2PO4*H,O (wlv), pH 7.6 (1 1). The mobile ex Fr.) Kumm. and Panaeolus subbaltea- phases were degassed with an ultrasonic bath and tus (Berk. & Br.) Sacc. Smaller amounts filtered through a 0.45 pm filter (Millipore). The (below 0.1% of dry weight) were mea- flow rate was 2 ml/min, the injection volume 10 ~1,and the wavelength of the detector 280 nm sured in Pluteus atricapillus Sing., (bandwidth 2nm). The pure standards for Panaeolus olivaceus Moller, Panaeolina psilocybin and psilocin were from Sandoz AG fmisecii (Pers. ex Fr.) R. Maire, (Basel). Psatbyrefla candolleana (Fr.) R. Maire, and Conocybe kuebneriana Sing. and in a RESULTS AND DISCUSSION species of Agrocybe. C. cyanopus, C. Altogether ten species belonging to kuebneriana and Pa. oliuaceus have not seven genera were found to contain been recorded earlier from Finland. PI. psilocybin andor psilocin (Table 1). The atricapilfus, C. kuebneriana and Pa. highest concentrations (over 0.5% ofdry ofivaceus are not reported in the literature Jul-Aug 19871 Ohenoja et al. : Psilocybin and Psilosin 743 to contain these compounds. One reason persist in fungal fruit bodies. The speci- might be that the concentrations of mens were from the year 1843, 1869, psilocybin and psilocin are very low and 1954, and 1976, all being ofPs. semilan- cannot be detected from dry material. Of cuta. Psilocybin was found to be very st- the specimens that contain psilocybin able in dried fruit bodies. Even the 115- andlor psilocin, PI. atricapillus, Pan- year-old collection still showed a aeolina foenisecii, Ps. semilancuta, and measurable amount of psilocybin, Psathyrella candolleana are common namely 0.014% ofdry weight (Table 1). species in Finland. The oldest specimen, on the other hand, The difficulties in the taxonomy of did not show any activity. The concen- fungus species may be one source of not- tration of psilocybin had a linear nega- able confusion and error in the literature; tive correlation with the age of collec- in addition, our material has included tions. Psilocin seemed to be much less problems. We analyzed a specimen, stable, and it was only detected in fresh identified as Psilocybe atrobrunnu by specimens or in species that contained Guzman, which contains much psilocy- high concentrations of psilocybin. bin and psilocin. Its morphological The chromatography column used characteristics agree fairly well with was found to be reliable and stable; those given by GuzmPn (12), but the about 450 samples were analyzed with- ecology is different. Ps. atrobrunnea was out significant changes in the retention described from Sphagnum vegetation; our volume or the peak configuration. Be- specimen grew on lawn. In this study it cause interfering peaks of method A is included with Ps. semilancuta. We were not present in method B, we con- have seen also the specimens analyzed by sider both methods essential for reliabil- Hoiland (13) and reported as Ps. atro- ity. The same selectivity can also be ob- hunnu. They have smaller and paler tained by using simultaneous multiple spores, for example, than Ps. atrobrunnu detection (19). has. ACKNOWLEDGMENTS Rald (14) considers Pa. fimicola and Pa. oliuaceus synonymous, but Gerhardt The chemical analyses were made in the De- (15), who identified our material, has partment of Pharmacology and Toxicology of the found those two species distinctly differ- University of Kuopio, and the samples were iden- tified in the Botanical Museum of the University ent. Stijve et al. (16) are of the opinion of Oulu. Some identifications were made and con- that Panaeolina foenisecii cannot contain firmed by Dn. E. Gerhardt, Berlin, FRG; G. psilocybin or psilocin at all. Two of our Guzmin, Xalapa, Mexico; E. Rald, Copenhagen, analyses were, however, positive. Denmark; R. Watling, Edinburgh, UK; J. Vau- The genus Conocybe is very little ras, Turku, Finland; and E. Vellinga, Leiden, The Netherlands, to whom the authors wish to known in Finland and even in whole express their gratitude. Fennoscandia. According to Watling (17), C. kuehnerima is fairly common in LITERATURE CITED the British Isles, but it is not known to 1. R.E. Schultes and A. Hofmann, “The be hallucinogenic. Botany and Chemistry of Hallucinogens,” The genus Agrocybe is considered 2nd Ed., Charles C. Thomas, Springfield, Illinois, 1980. psychoactive according to Koike et ai. 2. S.H. Pollock, J. Psyched. Drugs, 7, 73 (18), who found psilocybin in A. (1975). farinarea. Our collection was inadequate 3.
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