Gut microbiota is populated with an immense number of microorganisms, which can be regulated by dietary components and drugs to markedly affect the nutritional and health status of the host. Eight medicinal isoquinoline alkaloids from natural plants were cultured anaerobically with rat gut microbiota and an LC/MSn-IT-TOF technique was used to identify the resulting metabolites. Palmatine, tetra...

The isoquinoline alkaloids and their biosynthetic relatives include many compounds which show important physiological properties in animals: dopamine, mescaline, morphine, papaverine, and narcotine are pertinent examples. The biosynthetic routes to the members of this family start from the essential aminoacids tyiosine or phenflalanine. Decarboxylation gives a phenethylamine building block (C,-...

Amaryllidaceae is a well-known family for its high alkaloidal content. These alkaloids comprise a unique group of bases that have been found to occur in this family. The Amaryllidaceae alkaloids represent a large and still expanding group of isoquinoline alkaloids, the majority of which are not known to occur in any other family of plants. This article reports on the phytochemical investigation...

A systematic survey of the different synthetic methodologies available for the syntheses of isoquinoline and yohimbinoid alkaloids revealed that the general approaches to these compounds involved either an A/B C — D/—i E approach or a D/E — C/B/A approach% We have now devised a novel method for the syntheses of both the isoquinoline and indole alkaloids belonging to the tetra— hydroprotoberberi...

From the quaternary alkaloidal fraction of the dried tubers of Stephania cepharantha, two new isoquinoline alkaloids, stecepharine and tetradehydroreticuline have been isolated along with the known compounds, magnoflorine, menisperine, steponine, cyclanoline, oblongine, cis-N-methylcapaurine and 2'-N-methylisotetrandrine. cis-N-Methylcapaurine (=9-O-methylstecepharine) was isolated as a natural...

Pyrrolo[2,1-a]isoquinoline alkaloids have been prepared via a visible light photoredox catalyzed oxidation/[3 + 2] cycloaddition/oxidative aromatization cascade using Rose Bengal as an organo-photocatalyst. A variety of pyrroloisoquinolines have been obtained in good yields under mild and metal-free reaction conditions.

It has been firmly established that humans excrete a small but steady amount of the isoquinoline alkaloid morphine in their urine. It is unclear whether it is of dietary or endogenous origin. There is no doubt that a simple isoquinoline alkaloid, tetrahydropapaveroline (THP), is found in human and rodent brain as well as in human urine. This suggests a potential biogenetic relationship between ...

Natural product discovery efforts have focused primarily on microbial biosynthetic gene clusters (BGCs) containing large multimodular polyketide synthases and nonribosomal peptide synthetases; however, sequencing of fungal genomes has revealed a vast number of BGCs containing smaller NRPS-like genes of unknown biosynthetic function. Using comparative metabolomics, we show that a BGC in the huma...

The title compound, C(26)H(39)NO(7), which was isolated from Delphinium anthriscifolium var. majus, has a lycoctonine carbon skeleton containing four six-membered rings (A, B, D and E) and three five-membered rings (C, F and G). Rings A, B and E adopt chair conformation, while ring D adopts a boat conformation. Rings C and F adopt envelope conformations.