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After detection of a presumed (assumed) alkaloid, large quantities of the specific plant
material are collected, dried, and defatted by petroleum ether extraction if seed or leaf is
investigated. This process usually leaves polar alkaloidal material behind but removes
neutrals. The residue, in aqueous alcohol, is extracted with dilute acid and filtered, and
the acidic solution is made basic. Crystallization can occasionally be effected by
adjustment of the pH. If such relatively simple purification fails, crude mixtures may be
used or, more recently, very sophisticated separation techniques have been employed.
Once alkaloidal material has been found, taxonomically related plant material is also
examined.
Until separation techniques such as chromatography and counter current extraction had
advanced sufficiently to be of widespread use, the principal alkaloids were isolated from
plant extracts and the minor constituents were either discarded or remained uninvestigated. With the advent of, first, column, then preparative thin layer, and now high
pressure liquid chromatography (hplc), even very low concentrations of materials of
physiological significance can be obtained in commercial quantities. The alkaloid
leurocristine (vincristine, 23, RCHO), one of the >90 alkaloids found in Catharanthus
roseus G. Don, from which it is isolated and then used in chemotherapy, occurs in
concentrations of _2 mg/100 kg of plant material.
Most recently, with the advent of enzyme assay and genomic manipulation, the
possibility of utilization of callous or root tissue or even isolated enzymes along with
genetic engineering techniques can be employed to enhance or modify production of
specific alkaloids.
4. Properties
Most alkaloids are basic and they are thus generally separated from accompanying
neutrals and acids by dilute mineral acid extraction. The physical properties of most
alkaloids, once purified, are similar. Thus they tend to be colorless, crystalline, with
definite melting points, and chiral; only one enantiomer is isolated.
However, among >10,000 individual compounds, these descriptions are over
generalizations and some alkaloids are not basic, some are liquid, some brightly
coloured, some achiral, and in a few cases both enantiomers have been isolated in equal
amounts, i.e., the material as derived from the plant is racemic (or racemization has
occurred during isolation).
5. Organization
Early investigators grouped alkaloids according to the plant families in which they are
found, the structural types based on their carbon framework, or their principal
heterocyclic nuclei. However, as it became clear that the alkaloids, as secondary
metabolites, were derived from compounds of primary metabolism (eg, amino acids or
carbohydrates), biogenetic hypotheses evolved to link the more elaborate skeletons of
alkaloids with their simpler proposed progenitors (41). These hypotheses continue to
serve as valuable organizational tools and in many cases, enzyme catalyzed processes
affirming them have been found (36).