Structure, biosynthesis and activity of indolactam alkaloids.

Alkaloids Chem Biol

School of Environmental and Life Sciences, The University of Newcastle, Callaghan, NSW, Australia; The Australian Research Council Centre of Excellence in Synthetic Biology, Macquarie Park, NSW, Australia.

Published: October 2024

AI Article Synopsis

  • - Indolactam alkaloids are toxic compounds produced by certain actinobacteria and the cyanobacterium Moorena producens, known for causing skin issues like severe dermatitis and potential serious health risks from ingestion.
  • - Notable types of these alkaloids include teleocidins, lyngbyatoxins, and others, which contain a common nine-membered lactam core made from l-tryptophanol and l-valine.
  • - This chapter discusses the history and current understanding of indolactam alkaloids, including their isolation, structure, biosynthesis, biological effects, and methods of synthesis, covering research from their discovery in the 1960s up to 2024.

Article Abstract

Indolactam alkaloids are a family of aromatic toxins produced by various actinobacteria and the cyanobacterium, Moorena producens. The best characterized examples include the teleocidins, lyngbyatoxins, olivoretins, blastmycetins, and pendolmycins, which share a nine-membered lactam core, comprised from l-tryptophanol and l-valine. Contact with indolactam alkaloids has been linked to severe dermatitis (swimmers itch), while accidental ingestion may lead to illness and fatalities. Indolactam alkaloids are also potent tumor promotors, due to their activation of protein kinase C isozymes. This chapter reviews the current literature on indolactam alkaloids, from their discovery in the early 1960s up to 2024. Topics covered include the isolation, structural elucidation, biosynthesis, bioactivity, and total synthesis of the indolactam alkaloid core.

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Source
http://dx.doi.org/10.1016/bs.alkal.2024.07.001DOI Listing

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