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ISOLATION AND CHARACTERIZATION OF
ALKALOIDS ISOLATED FROM Z.ARMATUM
ABDUL SAMAD
DR.SYED BADSHAH
1
OUTLINES
 INTRODUCTION
 ISOLATION
 CHARACTERIZATION
2
A class of naturally occurring organic nitrogen-containing
bases.
Some synthetic compounds of similar structure are also
termed alkaloids.
In addition to carbon, hydrogen and nitrogen, alkaloids
may also contain oxygen, sulfur and more rarely other
elements such as chlorine, bromine, and phosphorus.
Natural compounds containing nitrogen in the exocyclic
position (mescaline, serotonin, dopamine, etc.) are usually
attributed to amines rather than alkaloids.
ALKALOIDS
3
 The name "alkaloids" (German: Alkaloid) was
introduced in 1819 by the German chemist Carl
Friedrich , and is derived from Latin root Latin: alkali
(which, in turn, comes from the Arabic al- qalwī –
"ashes of plants").
 Biological precursors of most alkaloids are amino acids.
 There are a few typical reactions involved in the
biosynthesis of various classes of alkaloids, including
synthesis of Schiff bases and Mannich reaction.
4
 CARBAZOLE, an aromatic heterocyclic organic compound.
 Tricyclic structure, consisting of two six-membered benzene rings
fused on either side of a five-membered nitrogen-containing ring.
5
6
7
Powdered plant material
Defatted with non-polar solvent
Defatted plant material
Moist with water and treated with NH3, Dil. Lime solution (Free Alkaloid)
Extracted with organic solvent like chloroform, ether
Extract, Concentrate it
Dissolved in Dil. Acid (Alkaloidal salt)
Aqueous phase Organic phase impurities
Basified with ammonia or sodium
Bi-carbonate or Dil. KOH
Aqueous phase Organic phase(Free Alkaloid)
Evaporate to dryness
Crude Alkaloids
Extraction of Alkaloids
8
9
A B C
C1 C2
C3
C4
10
Compound 1
4-methoxy-12, 12-dimethylcyclopenta
furoquinoline-10-carbaldehyde
8
2
345
6
7
8a 9a
3a
10
11
12
4a
11
Whit crystals
MP: 210- 212
C18H15NO3
1H NMR
12
13C NMR
13
Compound 2
Methyl 4-methoxy-12,12-dimethylcyclopenta furoquinoline-10-carboxylate
14
White needles
1H NMR
15
13C NMR
16
Compound 3
2, 6, 7-trimethoxy-8-(3-methyl-2-butenyl) carbazole-3-carbaldehyde
17
(Yellow needles)
1H-NMR
18
13C-NMR
19
Compound 4
Methyl -2, 6, 7-trimethoxy-8-(3-methyl-2-butenyl)carbazole-3-carboxylate
20
(Yellow solid)
1HNMR
21
22
13C-NMR
23
24

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New prenylated carbazole and furoquinoline alkaloids from Z. aramatum DC.Presentation 6th seminar

  • 1. ISOLATION AND CHARACTERIZATION OF ALKALOIDS ISOLATED FROM Z.ARMATUM ABDUL SAMAD DR.SYED BADSHAH 1
  • 3. A class of naturally occurring organic nitrogen-containing bases. Some synthetic compounds of similar structure are also termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Natural compounds containing nitrogen in the exocyclic position (mescaline, serotonin, dopamine, etc.) are usually attributed to amines rather than alkaloids. ALKALOIDS 3
  • 4.  The name "alkaloids" (German: Alkaloid) was introduced in 1819 by the German chemist Carl Friedrich , and is derived from Latin root Latin: alkali (which, in turn, comes from the Arabic al- qalwī – "ashes of plants").  Biological precursors of most alkaloids are amino acids.  There are a few typical reactions involved in the biosynthesis of various classes of alkaloids, including synthesis of Schiff bases and Mannich reaction. 4
  • 5.  CARBAZOLE, an aromatic heterocyclic organic compound.  Tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. 5
  • 6. 6
  • 7. 7
  • 8. Powdered plant material Defatted with non-polar solvent Defatted plant material Moist with water and treated with NH3, Dil. Lime solution (Free Alkaloid) Extracted with organic solvent like chloroform, ether Extract, Concentrate it Dissolved in Dil. Acid (Alkaloidal salt) Aqueous phase Organic phase impurities Basified with ammonia or sodium Bi-carbonate or Dil. KOH Aqueous phase Organic phase(Free Alkaloid) Evaporate to dryness Crude Alkaloids Extraction of Alkaloids 8
  • 9. 9
  • 10. A B C C1 C2 C3 C4 10
  • 11. Compound 1 4-methoxy-12, 12-dimethylcyclopenta furoquinoline-10-carbaldehyde 8 2 345 6 7 8a 9a 3a 10 11 12 4a 11 Whit crystals MP: 210- 212 C18H15NO3
  • 14. Compound 2 Methyl 4-methoxy-12,12-dimethylcyclopenta furoquinoline-10-carboxylate 14 White needles
  • 17. Compound 3 2, 6, 7-trimethoxy-8-(3-methyl-2-butenyl) carbazole-3-carbaldehyde 17 (Yellow needles)
  • 20. Compound 4 Methyl -2, 6, 7-trimethoxy-8-(3-methyl-2-butenyl)carbazole-3-carboxylate 20 (Yellow solid)
  • 23. 23
  • 24. 24