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    Home > J. Nat. Prod.: extraction and identification of natural product ω - n-methyl-4-hydroxytryptamine (norpsilocin) from Pleurotus ostreatus

    J. Nat. Prod.: extraction and identification of natural product ω - n-methyl-4-hydroxytryptamine (norpsilocin) from Pleurotus ostreatus

    • Last Update: 2017-09-22
    • Source: Internet
    • Author: User
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    The fungus of Pleurotus and other related genera and species is called magic mushroom Once ingested, it will cause dramatic changes in human emotion and perception, which is often called hallucination These "poisonous mushrooms" will produce tryptamine derivatives psilocin and psilocybin, which are known as hallucinogens, which are the main culprit of hallucinations after ingestion Psilocybin represents a class of drugs After oral administration, it will rapidly dephosphorylate into psilocybin with psychoactive effect Psilocin and psilocybin were first discovered by Hoffman and his research partners In the next few decades, the synthetic psilocybin derivatives and the homologues in natural products have been gradually discovered and recorded This includes baeocystin, norbaeocystin, aeruginascin Omega-n-methyl-4-hydroxytryptamine (1) is assumed to be the direct precursor of baeocystin Recent in vitro studies have shown that 1 is directly derived from a small shunt of 4-hydroxytryptamine and then phosphorylated to baeocystin However, compound 1, considered to be a synthetic product and an artificially dephosphorized extract of Pleurotus ostreatus, has never been identified as a natural product But we found it is a natural product in the Pleurotus nudus The 1H NMR data of norpsilocin (1) (source: J NAT Prod.) researchers purchased the Pleurotus Cuban strain and cultured it with malt extract / peptone (MEP) solid medium After harvest, different extraction methods were used for comparison Scheme 1 (weighing, freeze-drying in liquid nitrogen for 2 days, grinding into fine powder with mortar and pestle, and then extracting with 20ml absolute methanol for each gram of fresh reuse) After dry extraction, shake, filter and vacuum distillation The dried extract is then extracted and separated with a mixture of organic and aqueous phases Compound 1 was obtained by further separation and purification of the filtered water phase Because it is sensitive to air and easy to decompose, it needs to be protected under inert gas After that, 1H NMR test was carried out to confirm that its structure is indeed norpsilocin After comparing several different extraction methods, the researchers confirmed that water would have an impact on the extraction results If not freeze-dried before extraction, then water may cause reaction in the extraction process, make some natural products into derivatives, change the chemical structure, and affect the actual distribution ratio Two previous studies have consistently reported that the concentration of psilocybin is six times higher than that of psilocybin Previous reports may have overestimated the natural concentration of psilocybin in fungi The results show that the drying process itself is likely to determine dephosphorization and acidification, and water has an impact on the research results This in turn indicates that dephosphorylation is caused by enzyme catalysis rather than spontaneous process Considering the reported psychoactive effect of baeocystin, 1 is probably the actual active form after 4-o-dephosphorylation in vivo This hypothesis is similar to the alkaloids of psilocybin / psilocin pairs Due to its low concentration in natural products, 1 is unlikely to be the main hallucinogenic component of the ingested "magic mushroom" Mushrooms have been used as illegal psychedelic drugs However, when their medicinal potential is considered, the value of their alkaloid natural products becomes obvious Recent studies have shown that psilocybin has a positive effect on the treatment of addiction, chronic depression and anxiety Compound 1 may be selected as a drug precursor for further drug development.
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