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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