Analysis of indole alkaloids in Norwegian Psilocybe semilanceata using high-performance liquid chromatography and mass spectrometry

Christiansen, A.L.; Rasmussen, Knut

doi:10.1016/s0021-9673(00)85700-3

Cited by 25 publications

(13 citation statements)

References 9 publications

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“…It displayed the same mass spectrum as phosphoric ester (PT). The UV spectra of the compound showed very similar maxima as psilocin (CHRISTIANSEN andRASMUSSEN 1982, WURST et al 1984): 223, 260, 267, 282 and293 nm. By using alkaline phosphatase a complete cleavage of PT and a subsequent formation of HT could be observed.…”

Section: Resultsmentioning

confidence: 60%

“…The alkaloid was subsequently detected in various collections of P. semilanceata (GARTZ 1985a, CHRISTIANSEN and RASMUSSEN 1982, REPKE and LESLIE 1977, VANHAELEN-FASTRE and VANHAELEN 1984.…”

Section: Resultsmentioning

confidence: 99%

“…Baeocystin was first detected by LEUNG and PAUL (1968), who isolated this incompletely methylated counterpart of psilocybin from Psilocybe baeocystis SINGER and SMITH grown in submerged culture. The alkaloid was subsequently detected in various collections of P. semilanceata (GARTZ 1985a, CHRISTIANSEN and RASMUSSEN 1982, REPKE and LESLIE 1977, VANHAELEN-FASTRE and VANHAELEN 1984.…”

Section: Resultsmentioning

confidence: 99%

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Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe

Gartz

1989

J. Basic Microbiol.

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Mycelial cultures of Psilocybe cubensis capable of forming psilocybin and psilocin de novo display a high capacity for hydroxylation of tryptamine derivatives at the 4-position. A specific biotransformation of added synthetic N,N-diethyl-tryptamine was found. Thus high amounts of 4-hydroxy-N,N-diethyltryptamine (up to 3.3%) and a minor quantity of 4-phosphoryloxy-N,N-diethyltryptamine (0.01-0.8%) were isolated from fruiting bodies of Psilocybe cubensis in corresponding experiments. This is the first example of a directed biosynthesis of tryptamine substances by fungi. An effective biotransformation of N-methyltryptamine was also demonstrated with surface cultures of Psilocybe semilanceata. Baeocystin, a possible natural precursor of psilocybin, was detected and quantified in the biomasses. No alkaloids could be found in the culture medium.

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Section: Resultsmentioning

confidence: 60%

“…The alkaloid was subsequently detected in various collections of P. semilanceata (GARTZ 1985a, CHRISTIANSEN and RASMUSSEN 1982, REPKE and LESLIE 1977, VANHAELEN-FASTRE and VANHAELEN 1984.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe

Gartz

1989

J. Basic Microbiol.

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“…As far as it is currently known, this trimethylammonium analog of psilocybin has only been reported to occur in the hallucinogenic species Inocybe aeruginascens Babos. [13,21] Psilocybe semilanceata is the best studied psychoactive mushroom species in the world [1,14,18,19,17,22,23] and is known to contain psilocybin and baeocystin (Table 1). Previous investigations in 1994 have shown that the use pure methanol yielded the authentic indole derivatives from dried mushrooms and the use of aqueous solvents resulted in hydrolysis of psilocybin and baeocystin to give psilocin.…”

Section: Description Of the New Species Psilocybe Germanica Gartz And Wmentioning

confidence: 99%

“…It contained high amounts of psilocybin and baeocystin. This mushroom appears to be [16] 0.34 À 0.98 0.01 À 0.05 0.01 À 0.93 P. cyanescens [17] 0.25 À 0.85 0.01 À 0.03 0.04 À 0.36 P. semilanceata [3,4] 0.19 À 1.34 0.03 À 0.38 nd P. semilanceata [18] 0.55 À 1,96 0,11 À 034 À P. semilanceata [19] 0.41 À 1.41 0.10 À 0.60 traces P. semilanceata [14] 0,91 À 1,05 qualitative nd À 0.02 P. semilanceata [17] 0.05 À 1.70 nd À 0.36 nd À 0.36 P. bohemica [14] 0.25 À 1.14 nd nd À 0.07 P. bohemica [17] 0.28 À 0.80 0.01 À 0.03 nd À 0.02 P. bohemica [20] 0.11 À 1,35 0.01 À 0.03 0.01 À 0.02 P. azurescens [9] 1.17 À the first described species derived from wood chips that contains significant amounts of baeocystin in the absence of psilocin. The novel species was differentiated from other psychoactive taxons such as Psilocybe cyanescens, Psilocybe azurescens and Psilocybe bohemica in combination from features of the stipes and caps.…”

Section: Description Of the New Species Psilocybe Germanica Gartz And Wmentioning

confidence: 99%

Discovery of a new caerulescent Psilocybe mushroom in Germany: Psilocybe germanica sp.nov.

Gartz¹,

Wiedemann²

2015

Drug Testing and Analysis

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Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis

Gotvaldová

Hájková

Borovička

et al. 2020

Drug Testing and Analysis

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Psilocybin, psilocin, baeocystin, norbaeocystin, and aeruginascin are tryptamines structurally similar to the neurotransmitter serotonin. Psilocybin and its pharmacologically active metabolite psilocin in particular are known for their psychoactive effects. These substances typically occur in most species of the genus Psilocybe (Fungi, Strophariaceae). Even the sclerotia of some of these fungi known as “magic truffles” are of growing interest in microdosing due to them improving cognitive function studies. In addition to microdosing studies, psilocybin has also been applied in clinical studies, but only its pure form has been administrated so far. Moreover, the determination of tryptamine alkaloids is used in forensic analysis. In this study, freshly cultivated fruit bodies of Psilocybe cubensis were used for monitoring stability (including storage and processing conditions of fruiting bodies). Furthermore, mycelium and the individual parts of the fruiting bodies (caps, stipes, and basidiospores) were also examined. The concentration of tryptamines in final extracts was analyzed using ultra‐high‐performance liquid chromatography coupled with mass spectrometry. No tryptamines were detected in the basidiospores, and only psilocin was present at 0.47 wt.% in the mycelium. The stipes contained approximately half the amount of tryptamine alkaloids (0.52 wt.%) than the caps (1.03 wt.%); however, these results were not statistically significant, as the concentration of tryptamines in individual fruiting bodies is highly variable. The storage conditions showed that the highest degradation of tryptamines was seen in fresh mushrooms stored at −80°C, and the lowest decay was seen in dried biomass stored in the dark at room temperature.

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Analysis of indole alkaloids in Norwegian Psilocybe semilanceata using high-performance liquid chromatography and mass spectrometry

Cited by 25 publications

References 9 publications

Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe

Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe

Discovery of a new caerulescent Psilocybe mushroom in Germany: Psilocybe germanica sp.nov.

Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis

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