ALKALOIDS

Group 1
ABALOS AFAGA AGTALAO ALAMO AQUINO ALBOS ANCHETA

ALKALOIDS

a group ofnaturally occurringchemical compoundsthat contain mostlybasic

nitrogenatoms

also includes some related compounds with neutral and even weaklyacidic
properties

produced by a large variety of organisms includingbacteria,fungi,plants,

andanimals

can be purified from crude extracts of these organisms by

acid-base extraction

History

"alkaloids" (German:Alkaloide) was introduced in 1819 by the German

chemistCarl Friedrich Wilhelm Meiner, and is derived from late Latin root
Latin:alkali(which, in turn, comes from the Arabical-qalw "ashes of
plants") and the suffixGreek:- "like".

Derosne-narcotine-1803

Serturner- morphine-1816

Pelletier and Caventou

Strychnine- emetine-brucine-piperine

Caffeine quinine-colchicine-coniine

Characteristics of Alkaloids

Mostly are physiologically active, some are poisonous (presence of amino

nitrogen)

Soluble in organic solvent, insol. in water: alkaloidal salts behave conversely as

to its solubility

Pure alkaloids unite with acid to form substituted ammonium salts, alkaloids are
freed from their salt by the addition of alkali.

Alkaloids contains nitrogen, nitrogen may exist as primary amine (RNH2),

secondary amine (R2NH), tertiary amine (R3N) and quarternary amine (R4N+X-)

Mostly are crystalline solids, few are amorphous, liquids for those that lacks
oxygen

Alkaloids form double salts with compound of mercury, gold, platinum and other
heavy metals, in the form of precipitate (a false positive result may be observed
due to presence of proteins

Usually possess a bitter taste, perfect test to detect the presence of alkaloids

Methods of Obtaining Alkaloids

Maceration the process of soaking a drug in a menstruum until the soluble

portions are all in solution

Percolation comes from the word percolare, to strain through, process by

which the soluble portions of a drug are separated from it by the descent of a
solvent through it.

Continuous Extraction - uses Soxhlet Apparatuswhen the desired compound

has a limited solubility in a solvent, and the impurity is insoluble in that
solvent.

Alkaloids are often divided into the following major

groups:

"True alkaloids" - which containnitrogenin theheterocycleand originate

fromamino acids. Their characteristic examples areatropine, nicotine, and
morphine. This group also includes some alkaloids that besides nitrogen
heterocycle containterpene(e.g.,evonine) or peptide fragments (e.g.
ergotamine). This group also includes piperidine alkaloidsconiineand
coniceinealthough they do not originate from amino acids.

"Protoalkaloids", which containnitrogenand also originate from amino

acids.Examples includemescaline,adrenalineandephedrine.

Polyamine alkaloids derivatives ofputrescine,spermidine, andspermine.

Peptide and cyclopeptide alkaloids.

Pseudalkaloids alkaloid-like compounds that do not originate from amino

acids.This group includesterpene-like andsteroid-like alkaloids, as well as
purine-like alkaloids

CLASSIFICATION OF ALKALOIDS

1.Non-Heterocyclic Alkaloids or Atypical Alkaloids:

These are also sometimes called proto-alkaloids or biological amines. These

are less commonly found in nature. These molecules have a nitrogen atom
which is not a part of any ring system. Examples of these include ephedrine,
colchicine, erythromycin and taxol etc.
Name

Structure

Biological Significance

Ephedrine

Adrenergic agent-used for

asthma and hay fever

Colchicine

Relieves gout

Non-Heterocyclic Alkaloids or Atypical

Alkaloids:
Name

Structure

Biological Significance

Erythromycin

Antibiotic

Taxol (Paclitaxel)

Used in the treatment of

ovarian cancer, breast
cancer and non-small cell
lung cancer

2.Heterocyclic Alkaloids or Typical

Alkaloids:

Structurally these have the nitrogen as a part of a cyclic ring system. These
are more commonly found in nature. Heterocyclic alkaloids are further
subdivided into 14 groups based on the ring structure containing the nitrogen.

No.

Heterocycle

1.

Pyrrole and Pyrrolidine

2.

Pyrrolizidine

Example

Hygrine, Stachydrine

Senecionine, Symphitine, Echimidine, Seneciphylline

Heterocyclic Alkaloids or Typical Alkaloids:

No.

Heterocycle

Example

3.

Pyridine and Piperidine

Lobeline, Nicotine, Piperine, Conine, Trigonelline

4.

Tropane (piperidine/N-methylpyrrolidine)

Cocaine, Atropine, Hyoscyamine, Hyoscine

5.

Quinoline

Quinine, Quinidine, Cinchonine, Cinchonidine

Heterocyclic Alkaloids or Typical Alkaloids:

No.

Heterocycle

Example

6.

Isoquinoline

Morphine, Emetine, Papaverine, Narcotine, Tubocurarine, Codeine

7.

Aporphine (reduced
isoquinoline/naphthalene)

Boldine

8.

Quinolizidine

Lupanine, Cytisine, Laburnine, Sparteine

Heterocyclic Alkaloids or Typical Alkaloids:

No.

Heterocycle

Example

9.

Indole or Benzopyrole

Ergometrine, Vinblastine, Vincristine, Strychnine,

Brucine, Ergotamine, Yohimbine, Reserpine,
Serpentine, Physostigmine

10.

Indolizidine

Castanospermine, Swainsonine

11.

Imidazole or glyoxaline

Pilocarpine, Pilosine

Heterocyclic Alkaloids or Typical Alkaloids:

No.

Heterocycle

Example

12.

Purine (pyrimidine/imidazole)

Caffeine, Theobromine

13.

Steroidal (some combined as

glycosides)*

Conessine, Solanidine

14.

Terpenoid*

Aconitine, lycaconitine, Aconine

*Note- Steroidal and terpenoid classes are also treated as separate classes or along with glycosides.

Other methods of classification

of alkaloids include:

Based on their pharmacological action: Alkaloids have very diverse

pharmacological actions. They are known to be adrenergics, antibiotics,
poisons, stimulants, diuretics, astringents, anti-inflammatory, antihypertensives, anti-mydriatics, analgesics, anti-gout, expectorant, emetic,
anti-spasmodic and many others. However, structurally diverse molecules
may show similar pharmacological actions while in certain cases the
activity might be identical for specific structure. Hence it is very difficult
to classify them on the sole basis of pharmacological action.
Based on their taxonomy: Alkaloids can be classified on the basis of
the biological source from which they are obtained but
thisgeneralizationsdo not work most often.
Based on their biosynthetic origin: Biosynthetic origin here means
from which fundamental chemical building block these alkaloids are
derived. For example indole alkaloids often come from tryptophan,
pyrrolidine and tropane containing alkaloids come from proline and
ornithine, quinolizidine containing alkaloids are derived from lysine.
Biosynthetic origin of classification is beneficial in a more ordered

References:

Evans, W. C.Trease and Evans Pharmacognosy, 16th ed.; Elsevier: New York,
2009.

Kokate, C. K.; Gokhale, S. B.; Purohit, A. P.A textbook of Pharmacognosy,

29th ed.; Nirali Prakashan: Pune, 2009.

http://pharmaxchange.info/press/2012/07/classification-of-alkaloids/

https://en.wikipedia.org/wiki/Alkaloid