Tuesday, 7 August 2018

Chemistry of Alkaloids


History of Alkaloids:
  •       The French apothecary Derosne probably isolated the alkaloid afterwards  known as narcotine in 1803 and the Hanoverian apothecary Sertürner further investigated opium and isolated morphine (1806, 1816).
  •        Isolation of other alkaloids, particularly by Pelletier and Caventou, rapidly followed; strychnine (1817), emetine (1817), brucine (1819), piperine (1819), caffeine (1819), quinine (1820), colchicine (1820) and coniine (1826). 
  •     Coniine was the first alkaloid to have its structure established (Schiff, 1870) and to be synthesized (Ladenburg, 1889), but for others, such as colchicine, it was well over a century before the structures were finally elucidated.
  •      Modern methods and instrumentation have greatly facilitated these investigations, chemists during the first quarter of the last century would now be sufficient, several thousand times over, for a complete structure analysis.
  •        In the second half of the twentieth century alkaloids featured strongly in the search for plant drugs with anticancer activity.
  •        There is much current interest in other alkaloids having anticancer properties as well as those exhibiting antiaging and antiviral possibilities.

Alkaloids have complex molecular structure.
  • Steps for structural elucidations.
    1.Determine the structure of pure Alkaloids as its molecular formula and optical rotatory power.
    2. Unsaturation:- Addition of Br    - Addition of halogen acids     - Hydroxylation with dil. alkaline permanganate.
  • 3. Cleaved into simple fragments by hydrolysis with water, acids or alkalies & fragments so obtained examined separately. i.e. piperine on hydrolysis gives piperidinepiperic acid both attached through acid – amide linkage.
    4. Ascertaining the functional nature of Oxygen & Nitrogen atoms.