DD287053A5 - PROCESS FOR OBTAINING BAEOCYSTIN BY BIOTRANSFORMATION OF TRYPTAMINE - Google Patents

Abstract

The invention relates to a method for obtaining the active substance Baeocystin by biotransformation of tryptamine by means of basidiospores of higher fungi. The substance can be used as a pharmaceutical active substance and as a model substance in basic neurochemical research. Following the inoculation of a sterile mixture of tryptamine, methionine, yeast extract and phosphate with the basidiospores, a biotransformation to the baeocystin is achieved after up to 2 weeks of culture. The extraction of the active ingredient is carried out by known methods such as evaporation, extraction and chromatography. {Baeocystin; basidiospores; biotransformation; tryptamine; Basidiomycetes; Fertile soil; Psilocybe; Panaeolus; Conocybe; Gymnopilus}

Description

Field of application of the invention

The invention relates to a process for the recovery of Baeocystin by biotransformation of precursors by Basidiosporen. The substance Baeocystin can be used as a pharmaceutical active substance and as a model substance in neurochemical research.

Characterization of the known technical solutions

The tryptamine derivative Baeocystin (4-phosphoryloxy-N-methyltryptamine) occurs as an accompanying alkaloid of psilocybin and psilocin in naturally occurring higher fungi of various genera in small to very small amounts. It is known that the alkaloid can be isolated from the extracts of natural fungi by the use of chromatographic methods (Pharmazie 1985, 274).

The method described has several disadvantages. The yield of alkaloid is only slight, because by simple working methods no separation of the chemically distinctive only by an additional methyl group psilocybin with very similar physicochemical properties is possible. In addition, the naturally occurring fungi are not economically accessible. The biotransformation of tryptamine is known in cultured mycelia of higher fungi (DD-PS 265636}.) Although mycelium production is economically feasible in this process, the baeocystin is only produced in amounts of up to 0.25%, calculated on the dry masses As in the natural fungi, it can only be separated by loss of yield, and other mycelial substances (eg lipids) require additional processing steps, since the cultivation of mycelia takes at least 30 days to complete biotransformation Tryptamine.

Object of the invention

The aim of the invention is to develop a simple and inexpensive process for recovering the Baeocystins by biotransformation of tryptamine, which is achieved in aqueous solution, a high yield of Baeocystin without interfering Begleitalkaloide and organic substances in a short reaction time.

Explanation of the essence of the invention The invention has for its object to select such media for the biotransformation of tryptamine, which in aqueous Solution to ensure rapid formation of Baeocystins in high yield without side alkaloids. According to the invention the object is achieved in that the aqueous solution of tryptamine with the addition of methionine, Phosphates and yeast extract under sterile conditions with basidiospores and higher fungi, such as the genera Psilocybe, Conocybe, Panaeolus and Gymnopilus. After enzymatic biotransformation, the resulting Baeocystin separated in a conventional manner by evaporation, extraction or chromatography. In biotransformation, selective hydroxylation and phosphorylation occur in the 4-position of the indole ring in the Tryptamine, wherein at the same time the amino nitrogen is monomethylated in the side chain. Solutions of 1.5 to 3% methionine, 1 to 4% tryptamine or its water-soluble salts, 1.5 to

3% soluble phosphate, 0.1 to 0.3% yeast extract and water to 100%, optionally also with the addition of antibiotics, used and mixed with basidiospores in an amount of 0.1 to 0.2%.

For the biotransformation reaction spores of fungi of the genera Psilocybe, Panaeolus, Gymnopilus and Conocybe

used. After a reaction time of 5 to 14 days at 1 to 30 ° C, the Baeocystin in a known manner by filtration,

Evaporation, preferably in vacuo and subsequent extraction and / or chromatography in a yield of 70 to

90% isolated.

The invention will be explained in more detail by the following example. Ausführungsbelsplel

'c's are basidiospores of Psilocybe cubensis (Earle) Sing, used for inoculation, which mature from the lamellae

Fruit bodies were obtained by release under sterile conditions in a humid chamber.

0.1 g of the spore dust was added under sterile conditions to a mixture of 1.5 g of methionine, 2 g of tryptamine hydrochloride, 1.5 g of KH! PO ₄ and 0.1 g of yeast extract in 95 ml of water in a 300 ml Erlenmeyer flask with cotton stopper. After 10 days

Stirring (magnetic stirrer) at 20 ⁰ C, the bluish solution was filtered, after previously 150 ml of water were added. After that

was shaken with 50 ml of chloroform, the aqueous phase was evaporated (vacuum), treated with 20 ml of methanol at 0 ° C, filtered, the residue washed with 50 ml of acetone and then with 50 ml of acetone / diethyl ether and the solid residue with 500 ml

Dissolved methanol. After filtration to remove the inorganic salt becomes the methanolic solution of the Baeocystins

vacuo. eingedunstet.

Yield. * "Baeocystine after recrystallization from n-butanol: 2.1 g.

Claims (2)

1. A process for the recovery of Baeocystin by biotransformation of tryptamine, characterized in that the aqueous solution of tryptamine with the addition of methionine, phosphates and yeast extract under sterile conditions with basidiospores of higher fungi, such as those of the genera Psilocybe, Conocybe, Panaeolus and Gymnopilus inoculated and after the enzymatic biotransformation has taken place, the baeocystin is separated off by evaporation, extraction or chromatography in a manner known to the skilled person. 2. The method according to claim 1, characterized in that the biotransformation is carried out at 1 to 30 ⁰ C depending on the type of fungus and with or without the addition of antibiotics to the medium within 14 days.