CHEMISTRY OF NATURAL PRODUCTS
CHEMISTRY OF NATURAL PRODUCTS
(professor Manolis Stratakis)
Overview
1. Biosynthesis of terpenes
2. Biosynthesis of phenols
3. Metabolism of fatty acids
4. Metabolism of glucose (glycolysis)
5. Anabolic pathways of fatty acids
and carbohydrates
Biosynthesis of acyclic terpenoids
OPP
Me
Me OPP
Me
CH
3
COSCoA
Claisen-type
condensation CH
3
COCH
2
COSCoA
Aldol-type
condensation
2 NADPH 2 NADP 3 ATP 3 ADP Me
OP
O
HO OPP
CO
2
, Pi
Isomerization
Terpenes
From the metabolic pathways
of carbohydrates and fats
Isoprene units
Condensation of isoprene units. Formation of acyclic
terpenes
OPP
OPP
H
OPP
OPP
-H
+
geranyl OPP
OPP
farnesyl OPP
squalene
OPP
tail-tail dimerization
OPP
geranylgeranyl OPP
OPP
Formation of monoterpenes (examples)
Me Me
Me
OPP
Me Me
Me
OPP
- OPP
Me
Me Me
α-terpinyl cation
Me Me
Me
OH
Me Me Me
Me
O
Me
limonene
fenchone
camphene 3-carene
geraniol
myrcene
Me
Me
Me
Me
Me
Me
Me
CH
2
Me
Me
α- and β-pinene
enzyme
Formation of sesquiterpenes (examples)
Me Me
Me Me
OPP
Me Me
Me
Me
Me Me
Me
Me
H
H
Me
Me Me
Me
OH
bisabolene
cadinene
carotol