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Dimeric naphthylisoquinoline alkaloids: polyketide-derived axially chiral bioactive quateraryls. | LitMetric

Dimeric naphthylisoquinoline alkaloids: polyketide-derived axially chiral bioactive quateraryls.

Nat Prod Rep

Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.

Published: November 2019

AI Article Synopsis

  • Dimeric naphthylisoquinoline (NIQ) alkaloids are unique natural products found in African and Asian lianas, distinguished by their complex structures and biosynthesis from polyketides rather than aromatic amino acids.
  • These compounds contain multiple stereogenic centers and chiral axes, showcasing a new class of molecular architectures through oxidative cyclization.
  • The dimers exhibit a range of promising biological activities, including antiviral, antiprotozoal, and antitumor effects, which differ significantly from their monomer counterparts, making this the first comprehensive review on their isolation, diversity, and pharmacological potential.

Article Abstract

Covering: up to April 2019Dimeric naphthylisoquinoline (NIQ) alkaloids are an emerging group of structurally, biosynthetically, and pharmacologically intriguing natural products, as yet isolated from African and Asian lianas belonging to the genus Ancistrocladus Wall. (Ancistrocladaceae) exclusively. These metabolites and their monomers are the only known di- and tetrahydroisoquinoline alkaloids that do not originate from aromatic amino acids, but from polyketide precursors. Stereochemically, dimeric NIQs are characterized by the presence of several stereogenic centers and up to three consecutive chiral axes. The most recent highlight is the discovery of dimers that witness a new biosynthetic follow-up chemistry: by oxidative cyclization, leading to bridged, cage-like molecular architectures. Depending on their individual structures, the dimers show promising biological activities, including antiviral, antiprotozoal, and antitumor properties, most of them quite different from those of the monomers. This is the first review on these multi-facetted dimeric alkaloids, dealing with their isolation, their structural diversity, their biosynthetic origin, their pharmacological properties, and their total synthesis.

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Source
http://dx.doi.org/10.1039/c9np00024kDOI Listing

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