α-ergocryptine
Sign in to saveAlso known as 12'-hydroxy-2'-(1-methylethyl)-5'alpha-(2-methylpropyl)ergotaman-3',6',18-trione, 12'-hydroxy-5'alpha-isobutyl-2'-isopropylergotaman-3',6',18-trione
Ergocryptine is an ergopeptine and one of the ergoline alkaloids. It is isolated from ergot or fermentation broth and it serves as starting material for the production of bromocriptine. Two isomers of ergocryptine exist, α-ergocryptine and β-ergocryptine. The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid leucine is replaced by isoleucine. β-Ergocryptine was first identified in 1967 by Albert Hofmann. Ergot from different sources have different ratios of the two isomers.
Research
470 papers- Therapeutic potential of Xihuang Pill in colorectal cancer: Metabolomic and microbiome-driven approaches.Frontiers in pharmacology · 2024
- Inhibition of lactation.Drugs · 1975
- Ergocryptine and other ergot alkaloids stimulate the release of [3H]dopamine from rat striatal synaptosomes.Journal of animal science · 1999
- An ergocryptine as a lactation inhibitor.Gynecologic investigation · 1974
- Impacts of Cereal Ergot in Food Animal Production.Frontiers in veterinary science · 2016
via PubMed
Wikidata facts
- Mass
- 575.310769
Show 4 more facts
- chemical formula
- C₃₂H₄₁N₅O₅
- canonical SMILES
- CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
- isomeric SMILES
- CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
- Commons category
- Ergocryptine
Sources (2)
via Wikidata · CC0
~4 min read
Article
3 sectionsContents
- Biosynthesis
- See also
- References
Ergocryptine is an ergopeptine and one of the ergoline alkaloids. It is isolated from ergot or fermentation broth and it serves as starting material for the production of bromocriptine. Two isomers of ergocryptine exist, α-ergocryptine and β-ergocryptine. The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid leucine is replaced by isoleucine. β-Ergocryptine was first identified in 1967 by Albert Hofmann. Ergot from different sources have different ratios of the two isomers.
==Biosynthesis== The biosynthetic pathways to ergocryptine starts with the prenylation of L-tryptophan in an SN1 fashion with dimethylallyl pyrophosphate (DMAPP). DMAPP is derived from mevalonic acid. This reaction is catalyzed by a prenyltransferase enzyme (Prenyltransferase 4-dimethylallyltryptophan synthase) named FgaPT2 in Aspergillus fumigatus. An X-ray structure of the prenyltransferase FgaPT2 and tryptophan has been reported, and used to propose a three step mechanism: (1) formation of allylic carbocation; (2) nucleophile attack of tryptophan on the carbocation; (3) deprotonation to restore aromaticity and generate the product, 4-dimethylallyltryptophan (DMAT). DMAT is then N-methylated at the amino of the tryptophan backbone with the EasF enzyme, named FgaMT in A. fumigatus. S-adenosylmethionine (SAM) being the methyl source.