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2.1.5.1.1 Biosynthesis of Benzylisoquinoline and Indole Alkaloids

DOI: 10.1055/sos-SD-215-00081

Ilari, A.; Bonamore, A.; Boffi, A.Science of Synthesis: Biocatalysis in Organic Synthesis, (20152160.

Benzylisoquinoline alkaloids (BIAs) comprise a wide array (>2500) of plant secondary metabolites endowed with a variety of biological activities and pharmacological properties.[‌6‌,‌7‌] Narcotic analgesics, such as morphine and codeine, or muscle relaxants, such as tubocurarine and papaverine, are just a handful of examples of medicines derived from plant benzylisoquinoline alkaloids. The biosynthetic pathways leading to benzylisoquinoline alkaloid biosynthesis originate from tyrosine through a lattice of decarboxylations, hydroxylations, and deaminations that generates a species-specific mosaic of diverse secondary metabolites that have evolved as a plant defense system against pathogens or as deterrents against herbivores.[‌7‌] The common central pathway among different species evolves from l-tyrosine as precursor and comprises the condensation reaction between dopamine (1) and (4-hydroxyphenyl)acetaldehyde (2) (both derived from tyrosine metabolism) to yield the alkaloid (S)-norcoclaurine (3), catalyzed by the enzyme norcoclaurine synthase (NCS) (Scheme 2). (S)-Norcoclaurine is subsequently converted into (S)-reticuline by O- and N-methyltransferases and a P450 hydroxylase. (S)-Reticuline is a branch-point intermediate in the biosynthesis of many other benzylisoquinoline alkaloids, leading to protoberberine alkaloids, such as berberine and palmatine, and morphinan alkaloids, such as morphine and codeine. Details of the relevant biosynthetic pathways are being extensively updated and reviewed.[‌6‌,‌7‌]

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