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Alkaloids: History
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Contributor: Yu Peng

Alkaloids constitute a class of nitrogen-containing specialised metabolites that are biosynthesised by plants, fungi, bacteria, and certain animals and are characterised by the presence of at least one nitrogen atom within their molecular framework [1][2]. This nitrogen atom is typically basic and, in the majority of alkaloids, is incorporated into a heterocyclic ring system, a structural feature that confers the alkaline character from which the class derives its name [3][4]. Alkaloids are further organised according to their biosynthetic origin into three structural categories: true alkaloids, in which the nitrogen atom is derived from an amino acid and resides within a heterocycle; proto-alkaloids, in which the nitrogen is amino-acid-derived but lies outside a heterocyclic ring; and pseudo-alkaloids, in which the nitrogen is introduced at a late biosynthetic stage and is not amino-acid-derived [3][5]. The class is defined by pronounced structural diversity, with more than 27,000 structures reported and approximately 21,000 of these isolated from plants, and by a correspondingly broad range of biological activities that include toxicity, antimicrobial action, and pharmacological activity in humans and other animals [1][2]. Within the taxonomy of alkaloid synthesis and bioactivity, the term designates this nitrogen-containing, structurally heterogeneous group of specialised metabolites together with the biosynthetic pathways—rooted in amino acid metabolism and centred on iminium cation chemistry—through which their characteristic nitrogen heterocyclic scaffolds are constructed [1][3].

  • Nitrogen heterocycle
  • true alkaloids
  • proto-alkaloids
  • pseudo-alkaloids
  • specialised metabolites

 Synthesis and bioactivity of alkaloids • Molecular Biology • Biochemistry, Genetics and Molecular Biology • Life Sciences

References

  1. Peter J Facchini; ALKALOIDBIOSYNTHESIS INPLANTS: Biochemistry, Cell Biology, Molecular Regulation, and Metabolic Engineering Applications. Annu. Rev. Plant Biol. 2001, 52, 29-66, 10.1146/annurev.arplant.52.1.29.
  2. Jörg Ziegler; Peter J. Facchini; Alkaloid Biosynthesis: Metabolism and Trafficking. Annu. Rev. Plant Biol. 2008, 59, 735-769, 10.1146/annurev.arplant.59.032607.092730.
  3. Benjamin R. Lichman; The scaffold-forming steps of plant alkaloid biosynthesis. Nat. Prod. Rep. 2020, 38, 103-129, 10.1039/d0np00031k.
  4. Sweta Bhambhani; Kirtikumar R. Kondhare; Ashok P. Giri; Diversity in Chemical Structures and Biological Properties of Plant Alkaloids. Molecules 2021, 26, 3374, 10.3390/molecules26113374.
  5. Benjamin R. Lichman; The scaffold-forming steps of plant alkaloid biosynthesis. Nat. Prod. Rep. 2020, 38, 103-129, 10.1039/d0np00031k.
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