Lamellarin alkaloids: Isolation, synthesis, and biological activity

Alkaloids Chem Biol. 2020:83:1-112. doi: 10.1016/bs.alkal.2019.10.001. Epub 2020 Jan 23.

Abstract

Lamellarins are marine alkaloids containing fused 14-phenyl-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinoline or non-fused 3,4-diarylpyrrole-2-carboxylate ring systems. To date, more than 50 lamellarins have been isolated from a variety of marine organisms, such as mollusks, tunicates, and sponges. Many of them, especially fused type I lamellarins, exhibit impressive biological activity, such as potent cytotoxicity, topoisomerase I inhibition, protein kinases inhibition, and anti-HIV-1 activity. Due to their useful biological activity and limited availability from natural sources, a number of synthetic methods have been developed. In this chapter, we present an updated and comprehensive review on lamellarin alkaloids summarizing their isolation, synthesis, and biological activity.

Keywords: Anti-HIV-1 activity; Cytotoxicity; Lamellarin; Marine alkaloid; Mitochondrial inhibition; Multidrug resistance (MDR) reversal activity; Protein kinases inhibition; Structure–activity relationships (SAR); Topoisomerase I inhibition; Total synthesis.

Publication types

  • Review

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Animals
  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification
  • Anti-HIV Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Humans
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / isolation & purification
  • Protein Kinase Inhibitors / pharmacology*
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification*
  • Pyrroles / pharmacology*
  • Topoisomerase I Inhibitors / chemical synthesis
  • Topoisomerase I Inhibitors / chemistry
  • Topoisomerase I Inhibitors / isolation & purification
  • Topoisomerase I Inhibitors / pharmacology*

Substances

  • Alkaloids
  • Anti-HIV Agents
  • Antineoplastic Agents
  • Protein Kinase Inhibitors
  • Pyrroles
  • Topoisomerase I Inhibitors
  • lamellarin I