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Phytochemistry
S.Y.B.Sc. Botany Paper III
Unit 1
Part 3
Phytochemistry
Alkaloids
Colchicum
Vinca
Aconitum
Solanum xanthocarpum
Gloriosa superba
Papapver
Taxus
Ephedra
Ergot
Streptomyces
Alkaloids
Definition : Alkaloid = Alkali like
• Alkaloids are organic nitrogenous substances
usually found in plants. They are
heterogenous group of compound either from
chemical, biochemical or physiologic view
points.
• As name suggests they are alkaline in nature.
• Contain one or more than one nitrogen
(usually heterocyclic)
Alkaloids
Distribution
• Angiosperm families:
• Leguminosae
• Papaveraceae
• Rannunculaceae
• Rubiaceae
• Solanaceae
• Berberidaceae
• Liliaceae
• Apocynaceae
• Amaryllidaceae
Alkaloids
Distribution contd…
• Gymnosperms:
• Taxaceae
• Ephidraceae
• Fungi:
• Ergot
• Steptomyces erythrus
Alkaloids
Properties
• Basic in nature
• The nitrogen atom present responsible for
alkaline activity – resembles ammonia in
chemical property
• The nitrogen may exist as
• Primary – RNH2
• Secondary – R2NH
• Tertiary – R3N
Amine
Alkaloids
Properties contd..
• Alkaloids are converted into their salts by aq.
mineral acids
• The chemical rules designate that the names
of all alkaloids should end in ‘ine’
Alkaloids
Functions of alkaloids in plants
• Poisonous agents protecting the plant against
insects and herbivores “Animals that feed chiefly on
plants”.
• End products of detoxification reactions.
• Regulatory growth factors.
• Reserve substances capable of supplying nitrogen
or other elements necessary to the plant’s
economy.
Alkaloids
Functions of alkaloids in plants contd…
• Involved on acid metabolism in plant
• Storing and transportation of acid
• Do not participate in metabolic sequences
• Not solely the waste or end products of
metabolism.
Alkaloids
Extraction
Extraction is carried out by Organic solvents
Clear extract dried under vacuum
Plant material powdered in to fine powder
Moistened with water
Strong solution of alkali added (mostly liq. NH3)
Precipitation of alkaloid
Extracted with organic solvents (mostly CHCl3)
Separated by solubility method
Alkaloids
Classification of Alkaloids
• Generally, there are two broad divisions:
1.Heterocyclic or typical alkaloids, divided into 14
groups according to their ring structure.
2.Nonheterocyclic or atypical alkaloids, sometimes
called ‘protoalkaloids’.
• Alkaloids are usually classified according to the
nature of the basic chemical structures from
which they derive.
Classification of Alkaloids
Tests for alkaloids
There are several general reagents, which may
be used to test the presence of alkaloids or to
help their identification. This includes the
alkaloidal precipitating reagents and the
alkaloidal coloring reagents. In addition, there
are some special reagent that can be used for
recognizing and confirming the identity of each
alkaloid.
Tests for alkaloids
Alkaloidal precipitating reagents:
1. Mayer’s reagent (potassiomercuric iodide
solution)
2. Wagner’s reagent (solution of iodine in
potassium iodide)
3. Dragendorff’s reagent (potassium bismuth
iodide)
Tests for alkaloids
Alkaloidal coloring reagents:
1.Marqui’s reagent (Formaldehyde-sulfuric acid)
2.Mandalin’s reagent (sulphovanadic acid)
3.Erdmann’s reagent (Nitric acid-sulfuric acid)
Pharmacological activity and uses
Alkaloids are particularly interesting substances
because of their multiple pharmacological
activities:
1.on the CNS, whether they are depressants
(morphine) or stimulants (caffeine);
2.on the autonomic nervous system:
sympathomimetics (ephedrine) or
sympatholytics (yohimbine, certain ergot
alkaloids), parasympathomimetic (pilocarpine),
anticholinergics (atropine, hyoscyamine), or
ganglioplegics (nicotine).
Pharmacological activity and uses
In addition, alkaloids include
• Local anesthetics (cocaine),
• Agents to treat fibrillation (quinidine)
• Antitumor agents (vinblastine)
• Antimalarials (quinine)
• Antibacterials (berberine)
• Amebicides (emetine).
Epipedobates tricolor
N
Cl
H
N
Epibatidine
Pharmacognosy part 3

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Pharmacognosy part 3

  • 4.
  • 10.
  • 11. Taxus
  • 13. Ergot
  • 15. Alkaloids Definition : Alkaloid = Alkali like • Alkaloids are organic nitrogenous substances usually found in plants. They are heterogenous group of compound either from chemical, biochemical or physiologic view points. • As name suggests they are alkaline in nature. • Contain one or more than one nitrogen (usually heterocyclic)
  • 16. Alkaloids Distribution • Angiosperm families: • Leguminosae • Papaveraceae • Rannunculaceae • Rubiaceae • Solanaceae • Berberidaceae • Liliaceae • Apocynaceae • Amaryllidaceae
  • 17. Alkaloids Distribution contd… • Gymnosperms: • Taxaceae • Ephidraceae • Fungi: • Ergot • Steptomyces erythrus
  • 18. Alkaloids Properties • Basic in nature • The nitrogen atom present responsible for alkaline activity – resembles ammonia in chemical property • The nitrogen may exist as • Primary – RNH2 • Secondary – R2NH • Tertiary – R3N Amine
  • 19. Alkaloids Properties contd.. • Alkaloids are converted into their salts by aq. mineral acids • The chemical rules designate that the names of all alkaloids should end in ‘ine’
  • 20. Alkaloids Functions of alkaloids in plants • Poisonous agents protecting the plant against insects and herbivores “Animals that feed chiefly on plants”. • End products of detoxification reactions. • Regulatory growth factors. • Reserve substances capable of supplying nitrogen or other elements necessary to the plant’s economy.
  • 21. Alkaloids Functions of alkaloids in plants contd… • Involved on acid metabolism in plant • Storing and transportation of acid • Do not participate in metabolic sequences • Not solely the waste or end products of metabolism.
  • 22. Alkaloids Extraction Extraction is carried out by Organic solvents Clear extract dried under vacuum Plant material powdered in to fine powder Moistened with water Strong solution of alkali added (mostly liq. NH3) Precipitation of alkaloid Extracted with organic solvents (mostly CHCl3) Separated by solubility method
  • 24. Classification of Alkaloids • Generally, there are two broad divisions: 1.Heterocyclic or typical alkaloids, divided into 14 groups according to their ring structure. 2.Nonheterocyclic or atypical alkaloids, sometimes called ‘protoalkaloids’. • Alkaloids are usually classified according to the nature of the basic chemical structures from which they derive.
  • 26. Tests for alkaloids There are several general reagents, which may be used to test the presence of alkaloids or to help their identification. This includes the alkaloidal precipitating reagents and the alkaloidal coloring reagents. In addition, there are some special reagent that can be used for recognizing and confirming the identity of each alkaloid.
  • 27. Tests for alkaloids Alkaloidal precipitating reagents: 1. Mayer’s reagent (potassiomercuric iodide solution) 2. Wagner’s reagent (solution of iodine in potassium iodide) 3. Dragendorff’s reagent (potassium bismuth iodide)
  • 28. Tests for alkaloids Alkaloidal coloring reagents: 1.Marqui’s reagent (Formaldehyde-sulfuric acid) 2.Mandalin’s reagent (sulphovanadic acid) 3.Erdmann’s reagent (Nitric acid-sulfuric acid)
  • 29. Pharmacological activity and uses Alkaloids are particularly interesting substances because of their multiple pharmacological activities: 1.on the CNS, whether they are depressants (morphine) or stimulants (caffeine); 2.on the autonomic nervous system: sympathomimetics (ephedrine) or sympatholytics (yohimbine, certain ergot alkaloids), parasympathomimetic (pilocarpine), anticholinergics (atropine, hyoscyamine), or ganglioplegics (nicotine).
  • 30. Pharmacological activity and uses In addition, alkaloids include • Local anesthetics (cocaine), • Agents to treat fibrillation (quinidine) • Antitumor agents (vinblastine) • Antimalarials (quinine) • Antibacterials (berberine) • Amebicides (emetine).