Overview of Alkaloids: Classification, Sources, and Characteristics

 
Introduction
 
Are defined as organic nitrogenous compounds of plant origin that are
physiologically active.
In addition to 
carbon, hydrogen and nitrogen,
 alkaloids may also
contain 
oxygen, sulfur 
and more rarely other elements such as
chlorine, bromine, and phosphorus.
 The following families represent good examples:-
Leguminosae
 Papaveraceae
Ranunculaceae
Rubiaceae
Solanaceae
Berberidaceae
 
Sources of Alkaloids
 
Natural sources
a)
Plants (ephedrine) 
Ephedra sinica
b)
Animal (bufotenin) from skin
c)
Bacteria
d)
Fungi (psilocybin) from 
Psilocybe
  
Industrial sources
Nicotinic acid can be synthesized from tryptophan or
aspartic acid.
 
 
 
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1)
From the generic name of the plant as    atropine  
Atropa
belladonna
2)
From the specific name of the plant as cocaine
Erythroxylum coca.
3)
From the common name of the drug ergotamine .
4)
From their physiologic activity as 
emetine producing
emesis.
5)
From the discoverer as 
pelletrine.
6)
Other – e.g. morphine derived from ancient Greek
Other – e.g. morphine derived from ancient Greek
mythology – 
mythology – 
Morpheus – god of dreams
Morpheus – god of dreams
 
Classification
 
True alkaloids 
characterized by a heterocyclic ring with a
nitrogen atom, and are derived from amino acids for
example: are atropine, nicotine, and morphine.
 
Proto alkaloids 
characterized by absence of the heterocyclic
ring but also derived from amino acids for example:
adrenaline and ephedrine .
 
Pseudo alkaloids 
 characterized by a heterocyclic ring with a
nitrogen atom, but are not derived from amino acids.
 
In general the alkaloids are classified according to the
chemical
structure in two broad divisions:-
 
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1)
Pyrrol and Pyrrolidine.
2)
Pyrrolizidine.
3)
Pyridine and Piperidine.
4)
Tropane.
5)
Quinoline.
6)
Isoquinoline.
7)
Aporphine
8)
Norlupinane.
9)
Indole.
10)
Indolizidine.
11)
Imidazole.
12)
Purine.
13)
Steroid.
14)
Terpenoid
 
Alkaloid Description
 
Contains nitrogen - usually derived from an amino acid
Bitter taste.
Usually colorless
Some alkaloids are colored, yellow or orange.
Generally solids (except - nicotine is a brown liquid).
They give a precipitate with heavy metal iodides, except
Caffeine.
 
 
Most alkaloids are weak bases, but some are
amphoteric, for example theobromine and
theophyllin.
Most alkaloids are poorly soluble in water but its
dissolve in organic solvents, such as diethyl ether,
chloroform. However, caffeine dissolves well in
boiling water
Toxic for example cyclopamine which is present in
the leaves of corn lily.
 
Chemistry of Alkaloids
 
Alkaloids usually contain one nitrogen atom, but some may
contain up to (5) the nitrogen may exist as a primary amine
(RNH
2
), a secondary amine(R
2
NH), or as tertiary amine
(R
3
N) .
 
 
Applications
 
In medicine
 
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It belongs to the third group of the typical alkaloids, which is the
pyridine and piperidine group.
 
This plant is a perennial plant producing berry-like and aromatic
pungent fruits, that are green when unripe and become red at
mature, then the dried berries become black and wrinkled
producing black pepper.
 
 The pepper yields both, black and white pepper according to the
method of drying.
 
 In that when the ripe and the unripe fruit are dried directly under
the sun, black pepper is the result. While if the fruit is soaked,
and then removed the outer skin, before drying and then the
result is white pepper.
 
 
The alkaloid extracted from the black pepper is
piperine.
 
Piperine alkaloid is a solid substance essentially
insoluble in water. It is a weak base that is tasteless
at first, but leaves a burning after taste.
 
The molecular formula is Cₗ₇Hₗ₉NO₃.
 
1)
 Piperine aid in the digestion of food due to its
stimulation of the digestive enzymes.
 
2)
 There is some evidence that it has an
anticonvulsant activity in the treatment of epilepsy.
 
3)
 There is some evidence that it has an anticancer
and anti-inflammatory activity due to its
antioxidant property.
 
 
The Pharmacological Activity of Piperine
 
 
Isolation of Piperine  from Black Pepper
 
 
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Large beaker and medium size beaker
Soxhlet instrument
Water bath
Filter paper and funnel
90% ethanol
10% alcoholic potassium hydroxide
 
P
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e
d
u
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e
:
-
 
1)
10gm of black pepper are ground to a fine powder.
2)
 Extracted with 150 ml of 90% ethanol in Soxhlet extractor
for two hours.
3)
The solution is concentrated .
4)
Add 10ml of 10% alcoholic potassium hydroxide to the
filtrate residue and after a while decanted from the
insoluble residue .
5)
The alcoholic solution is left over night.
 
Results:-
Yellow needles with melting point of 125ºC are deposited. Yielding 0.3
gm of piperine alkaloid.
D
i
s
c
u
s
s
i
o
n
 
:
-
1)
 
The plant is affected by heat therefore Soxhlet apparatus is used in
its extraction.
2)
 The use of 90% ethanol is to extract both, the alkaloid and the
alkaloidal salt that might be present.
3)
The use of alcoholic KOH is to precipitate the isomers of piperine
that are chuvacine, isochuvacine and piperic acid.
4)
Alcohol was used in the preparation of KOH instead of water, since
water will hydrolyze piperine into piperidine and piperic acid.
 
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Alkaloids are organic nitrogenous compounds found in plants with physiological activity. They may also contain elements like oxygen, sulfur, chlorine, and phosphorus. Alkaloids can be sourced from plants, animals, bacteria, fungi, or industrial synthesis. Their names can be derived from plant names, drug activity, or discoverers. Alkaloids are classified into true, proto, and pseudo alkaloids based on their structure. They can further be categorized based on their chemical structure into heterocyclic and non-heterocyclic types. Alkaloids typically have a bitter taste, are colorless solids, and contain nitrogen, derived from amino acids.


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  1. Introduction Are defined as organic nitrogenous compounds of plant origin that are physiologically active. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. The following families represent good examples:- Leguminosae Papaveraceae Ranunculaceae Rubiaceae Solanaceae Berberidaceae

  2. Sources of Alkaloids Natural sources a) Plants (ephedrine) Ephedra sinica b) Animal (bufotenin) from skin c) Bacteria d) Fungi (psilocybin) from Psilocybe Industrial sources Nicotinic acid can be synthesized from tryptophan or aspartic acid.

  3. The names of alkaloids are obtained in different ways:- 1) From the generic name of the plant as atropine Atropa belladonna 2) From the specific name of the plant as cocaine Erythroxylum coca. 3) From the common name of the drug ergotamine . 4) From their physiologic activity as emetine producing emesis. 5) From the discoverer as pelletrine. 6) Other e.g. morphine derived from ancient Greek mythology Morpheus god of dreams

  4. Classification True alkaloids characterized by a heterocyclic ring with a nitrogen atom, and are derived from amino acids for example: are atropine, nicotine, and morphine. Proto alkaloids characterized by absence of the heterocyclic ring but also derived from amino acids for example: adrenaline and ephedrine . Pseudo alkaloids characterized by a heterocyclic ring with a nitrogen atom, but are not derived from amino acids.

  5. In general the alkaloids are classified according to the chemical structure in two broad divisions:- A) Non-heterocyclic or atypical alkaloids or biological amines. B) Heterocyclic or typical alkaloids, divided into (14) group according to their structure, as the following:-

  6. 1) Pyrrol and Pyrrolidine. 2) Pyrrolizidine. 3) Pyridine and Piperidine. 4) Tropane. 5) Quinoline. 6) Isoquinoline. 7) Aporphine 8) Norlupinane. 9) Indole. 10) Indolizidine. 11) Imidazole. 12) Purine. 13) Steroid. 14) Terpenoid

  7. Alkaloid Description Contains nitrogen - usually derived from an amino acid Bitter taste. Usually colorless Some alkaloids are colored, yellow or orange. Generally solids (except - nicotine is a brown liquid). They give a precipitate with heavy metal iodides, except Caffeine.

  8. Most alkaloids are weak bases, but some are amphoteric, for example theobromine and theophyllin. Most alkaloids are poorly soluble in water but its dissolve in organic solvents, such as diethyl ether, chloroform. However, caffeine dissolves well in boiling water Toxic for example cyclopamine which is present in the leaves of corn lily.

  9. Chemistry of Alkaloids Alkaloids usually contain one nitrogen atom, but some may contain up to (5) the nitrogen may exist as a primary amine (RNH2), a secondary amine(R2NH), or as tertiary amine (R3N) .

  10. Applications In medicine

  11. Black pepper Black pepper Botanical name Piper Family name Piperaceae Piper nigrum nigrum Piperaceae

  12. It belongs to the third group of the typical alkaloids, which is the pyridine and piperidine group. This plant is a perennial plant producing berry-like and aromatic pungent fruits, that are green when unripe and become red at mature, then the dried berries become black and wrinkled producing black pepper. The pepper yields both, black and white pepper according to the method of drying. In that when the ripe and the unripe fruit are dried directly under the sun, black pepper is the result. While if the fruit is soaked, and then removed the outer skin, before drying and then the result is white pepper.

  13. The alkaloid extracted from the black pepper is piperine. Piperine alkaloid is a solid substance essentially insoluble in water. It is a weak base that is tasteless at first, but leaves a burning after taste. The molecular formula is C H NO .

  14. The Pharmacological Activity of Piperine 1) Piperine aid in the digestion of food due to its stimulation of the digestive enzymes. 2) There is some evidence that it has an anticonvulsant activity in the treatment of epilepsy. 3) There is some evidence that it has an anticancer and anti-inflammatory activity due to its antioxidant property.

  15. Isolation of Piperine from Black Pepper Aim: - Isolation of piperine alkaloid from black pepper Equipments and reagents:- Large beaker and medium size beaker Soxhlet instrument Water bath Filter paper and funnel 90% ethanol 10% alcoholic potassium hydroxide

  16. Procedure:- 1) 10gm of black pepper are ground to a fine powder. 2) Extracted with 150 ml of 90% ethanol in Soxhlet extractor for two hours. 3) The solution is concentrated . 4) Add 10ml of 10% alcoholic potassium hydroxide to the filtrate residue and after a while decanted from the insoluble residue . 5) The alcoholic solution is left over night.

  17. Results:- Yellow needles with melting point of 125 C are deposited. Yielding 0.3 gm of piperine alkaloid. Discussion :- 1)The plant is affected by heat therefore Soxhlet apparatus is used in its extraction. 2) The use of 90% ethanol is to extract both, the alkaloid and the alkaloidal salt that might be present. 3) The use of alcoholic KOH is to precipitate the isomers of piperine that are chuvacine, isochuvacine and piperic acid. 4) Alcohol was used in the preparation of KOH instead of water, since water will hydrolyze piperine into piperidine and piperic acid.

  18. THANK YOU THANK YOU

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