β-Phenylethylamines and the isoquinoline alkaloids

Bentley, K. W.

doi:10.1039/np9951200419

Cited by 13 publications

(4 citation statements)

References 305 publications

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“…Secoberberines such as 5 ′ and 7 are structurally unique and are currently commercially inaccessible. Thus, few studies have been conducted on secoberberine-based drug development 39 40 41 42 43 44 45 46 . In addition, the structure of 7 synthesized by CYP82X1 has not been confirmed due to the lack of authentic standards and limited quantity of the compound achieved in the in vitro investigations 47 .…”

Section: Resultsmentioning

confidence: 99%

“…Noscapine is a phthalideisoquinoline alkaloid synthesized from L -tyrosine through scoulerine 36 , and the biosynthesis scheme involves multiple types of alkaloids, including 1-benzylisoquinoline, protoberberine and secoberberine alkaloids 37 38 . Among them, secoberberine alkaloids exhibit a unique structural scaffold, but their pharmacological activities are less investigated than alkaloids such as 1-benzylisoquinoline, protoberberine or phthalideisoquinoline alkaloids 39 40 41 42 43 44 45 46 , which may be due to limited access to these molecules.…”

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confidence: 99%

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Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

2016

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Noscapine is a potential anticancer drug isolated from the opium poppy Papaver somniferum, and genes encoding enzymes responsible for the synthesis of noscapine have been recently discovered to be clustered on the genome of P. somniferum. Here, we reconstitute the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates, complementing and extending previous in planta and in vitro investigations. Our work provides structural validation of the secoberberine intermediates and the description of the narcotoline-4′-O-methyltransferase, suggesting this activity is catalysed by a unique heterodimer. We also reconstitute a 14-step biosynthetic pathway of noscapine from the simple alkaloid norlaudanosoline by engineering a yeast strain expressing 16 heterologous plant enzymes, achieving reconstitution of a complex plant pathway in a microbial host. Other engineered yeasts produce previously inaccessible pathway intermediates and a novel derivative, thereby advancing protoberberine and noscapine related drug discovery.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

2016

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“…Substituted tetrahydroisoquinolines are attributed with broad spectrum of pharmacological properties which range from calcium antagonist and cardiovascular effects, antibacterial and antiplasmodial activity, to neuoromodulating effects .…”

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Unexpected Formation of 3-Substituted 1,2,3,4-Tetrahydroisoquinolines during Tosylation of N,N-dibenzylaminols

et al. 1999

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“…The polypropionates (chains with alternating methyl-hydroxy-methyl substituents) [33] represent an important class of natural products such as the ionophores, the lactones and the macrolides [34][35][36][37]. Associated with a broad spectrum of biological activity, these structures encompass a large diversity of molecular architecture.…”

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confidence: 99%