DD278600A1 - Process for obtaining tryptophane derivatives by culturing higher mushrooms - Google Patents

Process for obtaining tryptophane derivatives by culturing higher mushrooms Download PDF

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Publication number
DD278600A1
DD278600A1 DD32374188A DD32374188A DD278600A1 DD 278600 A1 DD278600 A1 DD 278600A1 DD 32374188 A DD32374188 A DD 32374188A DD 32374188 A DD32374188 A DD 32374188A DD 278600 A1 DD278600 A1 DD 278600A1
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DD
German Democratic Republic
Prior art keywords
indoles
obtaining
culturing
ethyl
cultivation
Prior art date
Application number
DD32374188A
Other languages
German (de)
Inventor
Jochen Gartz
Original Assignee
Akad Wissenschaften Ddr
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Akad Wissenschaften Ddr filed Critical Akad Wissenschaften Ddr
Priority to DD32374188A priority Critical patent/DD278600A1/en
Publication of DD278600A1 publication Critical patent/DD278600A1/en

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Abstract

The invention relates to the microbial recovery of tryptophan derivatives. It is applicable for the production of drugs for experimental neurobiology and drug synthesis. The invention consists in the use of solid nutrient media consisting of substrates to which 3 (2-dialkylaminoethyl) -indoles are added for biotransformation. The cultivation under Fruchtkoerperbildung takes place at 4 to 32C under diffuse light, the extraction and isolation of the active ingredients in a known manner. The inventive solution leads to high yields of the 4-substituted derivatives while suppressing the biosynthesis of other indole compounds.

Description

Field of application of the invention

The invention relates to a method for obtaining Tryptophanderivaten by artificially growing higher fungi on nutrient media containing Biotransformatiun substances. The 3 (2-dialkylaminoethyl) -4-hydroxyindoles which can be prepared from fruiting bodies can be used as model substances in neurobiological research and can also be used as an intermediate in drug syntheses.

Characterization of the known technical solution

4-substituted Tryphophanderivate occur in naturally occurring higher fungi of the genus Psilocybe, Stropharia, Pluteus, Conocybe and Inocybo in various species.

Artificially cultivated fruiting bodies and mycelia of these fungi also form the methylated compounds psilocybin, bacocystine and psilocin (DE 1087321). The disadvantage of this method is that bosynthetically no homologs of these extended alkyl chain substances can be formed since they are derived from the tryptophan containing a methyl group. Another method (Helvetica Chim. Acta 1959, 2073) describes the synthetic chemical recovery of the 3 (2-dialkyaminoethyl) -4-hydroxyindoles. The disadvantage of this process is a variety of complicated synthetic steps (up to 10 steps) to achieve ring closure to obtain the 4-hydroxyindoles. Poor yields in individual synthesis steps and the use of expensive and poorly manageable organometallic reagents are further disadvantages of this method.

Object of the invention

The aim of the invention is the effective preparation of 3 (-2-dialkylamino-ethyl) -4-hydroxyindoles in high yields while avoiding many synthetic reaction steps.

Explanation of the essence of the invention

The invention has for its object to produce by a biotechnological process, the 3 (-2-dialkylamino-ethyl) -4-hydroxyindole suppression of the synthesis of other indole compounds.

According to the invention, the object is golöst that the cultivation of higher species of fungi of the genera Psilocybe, Panaoolus, Stropharia, Inocybe, Conocybe and Pluteus is performed on solid nutrient media containing 0.1 to 2% 3 (-2-dialkylamino-ethyO-indoles , And the resulting 3 (-2-dialkylamino-ethyl) -hydroxyindole be obtained by known separation and purification methods from the fruiting bodies.

Ethyl, propyl, isopropyl and butyl radicals act as alkyl groups of the indoles to be biotransformed, preferably in the form of water-soluble salts.

The cultivation of the fruiting bodies takes place depending on the type of fungus at 4 to 32 0 C in diffuse light.

The fungi mentioned synthesize the fruiting bodies normally the alkaloids psilocin, psilocybin and balocystin.

The addition of 3 (-2-dialkylamino-ethyl) -indoles suppresses the denovo synthesis of these alkaloids and achieves biotransformation of the added indoles in the sense of a specific hydroxylation in the 4-position of the indole ring.

Thus yields of 4-hydroxylation products are possible, which amount to 2 to 4% of the dry mass of the fungi.

The procedure is such that inoculated with a suspension of Mycelflocken of autoclaved culture medium and is incubated in suitable containers at a temperature between 4 and 32 0 C for 20 to 60 days. After separation of the fungi and their freeze-drying, comminution and extraction by known methods, the active compounds are separated by chromatography also known methods.

By this simple operation, high yields of biomass can be obtained with a high content of 3 (-2-dialkylamino-ethyl) -4-indoles, the fungi no longer form significant amounts of psilocybin, psilocin and Baeocystin more.

By the following example, the invention will be explained in more detail.

embodiments

A primary culture of Psilocybe cubensis (Earle) Sing was used for inoculation obtained by germination of the spores on 6% malt agar, inoculation after 14 days and subsequent cultivation (20 days) on 100 ml of the same agar.

A mycelium piece of about 2 cm χ 2cm was then removed sterile (spatula) and by shaking with 30ml of sterile water and 15g saddle filling a suspension of fine Mycelflöckchen produced. 10 ml of the mixture were used to inoculate 100 g of an autoclaved mixture of 50% dry cow dung, 25% wheat straw and 25% water, after which 3 g of (2-dipropylaminoethyl-2-indole hydrochloride (in 10 ml of water) had been added before sterilization After 3 weeks, fruiting began, which occurred in 5 output waves.

Yield: 18g dry fruiting bodies

By extraction of finely powdered mushrooms with 3 times 500m! Methanol, filtration, evaporation i. Vak. (2O 0 C) and column chromatography on cellulose powder (30 cm column) was 3 (-2-dipropylamino-ethyl) -4-hydroxyxindole (mp: 102 ° C, yield: 420 mg) after recrystallization from ethyl acetate / chloroform shown as white crystals. The eluent used in det SC was water-saturated n-butanol.

No further indoles could be detected in the mushrooms.

Claims (4)

1. A method for obtaining Tryptophanderivaten by culturing higher species of fungi of the genus Psilocybe, Panaeolus, Stropharia, Inocybe, Conocybe and Pluteus, characterized in that the cultivation is carried out on solid nutrient media containing 0.1 to 2% 3 (-2- Diakylamino-ethyO-indoles contained, and the resulting 3 (-2-diakylamino-ethyl) -4-hydroxyindole be obtained by known separation and purification methods from the fruiting bodies.
2. The method according to claim 1, characterized in that act as alkyl groups ethyl, propyl, isopropyl and butyl radicals.
3. The method according to claim 1, characterized in that the 3 cultivation of the fruiting bodies is carried out at temperatures between 4 and 32 ° C in diffused light.
4. The method according to claim 1 to 4, characterized in that the indoles are preferably added in the form of soluble salts.
DD32374188A 1988-12-23 1988-12-23 Process for obtaining tryptophane derivatives by culturing higher mushrooms DD278600A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DD32374188A DD278600A1 (en) 1988-12-23 1988-12-23 Process for obtaining tryptophane derivatives by culturing higher mushrooms

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DD32374188A DD278600A1 (en) 1988-12-23 1988-12-23 Process for obtaining tryptophane derivatives by culturing higher mushrooms

Publications (1)

Publication Number Publication Date
DD278600A1 true DD278600A1 (en) 1990-05-09

Family

ID=5605513

Family Applications (1)

Application Number Title Priority Date Filing Date
DD32374188A DD278600A1 (en) 1988-12-23 1988-12-23 Process for obtaining tryptophane derivatives by culturing higher mushrooms

Country Status (1)

Country Link
DD (1) DD278600A1 (en)

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