New prenylated carbazole and furoquinoline alkaloids from Z. aramatum DC.Presentation 6th seminar
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Transcript of New prenylated carbazole and furoquinoline alkaloids from Z. aramatum DC.Presentation 6th seminar
ISOLATION AND CHARACTERIZATION OF
ALKALOIDS ISOLATED FROM Z.ARMATUM
ABDUL SAMAD
DR.SYED BADSHAH
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OUTLINES
INTRODUCTION
ISOLATION
CHARACTERIZATION
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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
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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.
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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.
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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
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A B C
C1 C2
C3C4
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Compound 1
4-methoxy-12, 12-dimethylcyclopenta
furoquinoline-10-carbaldehyde
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2
3456
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8a 9a
3a
10
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12
4a
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Whit crystals
MP: 210- 212
C18H15NO3
1H NMR
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13C NMR
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Compound 2
Methyl 4-methoxy-12,12-dimethylcyclopenta furoquinoline-10-carboxylate
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White needles
1H NMR
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13C NMR
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Compound 3
2, 6, 7-trimethoxy-8-(3-methyl-2-butenyl) carbazole-3-carbaldehyde
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(Yellow needles)
1H-NMR
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13C-NMR
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Compound 4
Methyl -2, 6, 7-trimethoxy-8-(3-methyl-2-butenyl)carbazole-3-carboxylate
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(Yellow solid)
1HNMR
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13C-NMR
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