PHARMACOGNOSY

Dealing with drugs derived from natural sources

Animals
Plants
M.O
Biosynthetic pathway of natural drugs
According to the biosynthetic pathway the natural compounds
classified into:
-Active compounds derived from shikimic acid pathway
-Active compounds derived from acetate –mevalonic acid
pathway
-Mixed pathway derived from both shikimic and mevalonate

Biosynthesis of aromatic compounds

Shikimicacidpathway:
-is a key intermediate from carbohydrate for the biosynthesis of
C6-C3 units (phenyl propane derivative).
-Besides serving as precursor for the biosynthesis of amino
acids, Shikmic acid is also an intermediate in production of
tannins, flavones, coumarins and vanillin . Present in
plants,fungi, and bacteria but is not found in animals, so animals
have no way to synthesis the three aromatic amino
acids(phenylalanine, tyrosine,and tryptophan) which are
therefore essential nutrients in animal diet.

-The shikimic acid pathway converts simple carbohydrate

precursors derived from glycolysis and the pentose phosphate
pathway to the aromatic amino acids.
-Shikimic acid through a series of phosphorylated intermediates
yield chorismic acid which is important branch point
intermediate.one branch leads to anthranilic acid then to
tryptophan .The other leads to prephenic acid which is the
last non aromatic compound in the sequence .
Prephenic acid can be aromatized in 2 ways:
-The first proceeds by dehydration and simultaneous
decarboxylation to yield phenyl pyruvic acid , the direct precursor of
phenylalanine.
The second occurs by dehydrogenation and decarboxylation to give p-
-hydroxyphenyl pyruvic acid , the precursor of tyrosine
Acetate hypothesis(biosynthesis of isoprenoid compounds)

1-Claisen condensation of 2 molecule of acetyl CoA to give

acetoacetylCoA

2-Aldole like condensation of acetoacetyl CoA with third

molecule of acetylCoA , followed by hydrolysis , gives (3s)-3-
hydroxy-3-methylglutaryl CoA

3-Reduction of the thioester group by2 equivalents of NADPH

gives (R)-mevalonate ,a dihydroxy acid.

4-phosphorylation of the tertiary hydroxyl and

diphosphorylation of the primary hydroxyl , followed by
decarboxylation and simultaneous expulsion of phosphate , give
isopentenyl diphosphate , the precursor of terpenoids
Biosynthesis of Glycosides

The principal pathway of glycoside formation involves the

transfer of uridylyl group from uridine triphosphate (UTP) to
sugar-1-phosphate and the enzymes catalyzing this reaction are
known as uridylyl transferases. The subsequent reaction
controlled by enzymatic system glycosyl transferases involves
transfer of sugar from uridine diphosphate to aglycone moiety
resulting in formation of glycoside .

The sugars present in glycosides may be monosaccharides such

as rhamnose, glucose. More than one molecule of such sugars
may be attached to the aglycone either by separate linkages,
which is rare, or, more commonly, as di-, tri- or tetrasaccharide.
Such complex glycosides are formed by stepwise addition of
sugars to aglycone. Since sugars exist in isomeric α- and β-
forms, both types are theoretically possible. Practically all
natural glycosides, however, are of the β- type