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- 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
From the metabolic pathways
of carbohydrates and fats
Claisen-type Aldol-type
condensation condensation
CH3COSCoA CH3COCH2COSCoA
2 NADPH 2 NADP 3 ATP 3 ADP
O Me
HO OPP
OP
CO2, Pi
Me Isomerization Me
OPP Me OPP Isoprene units
Terpenes
- Condensation of isoprene units. Formation of acyclic
terpenes
-H+
OPP OPP OPP
H
OPP
OPP OPP
geranyl OPP farnesyl OPP
OPP
tail-tail dimerization
OPP
geranylgeranyl OPP
squalene
- Formation of monoterpenes (examples)
Me
OH
geraniol Me Me
Me Me OPP
enzyme
OPP
Me Me Me Me
myrcene - OPP
Me Me Me
Me
α-terpinyl cation
limonene
Me CH2
Me Me
Me
O
fenchone Me Me
Me Me
Me α- and β-pinene
Me
Me
camphene Me 3-carene
Me
- Formation of sesquiterpenes (examples)
Me
Me bisabolene
Me Me
Me
H
Me Me
cadinene
OPP Me
H
Me Me
Me Me
Me
Me
Me OH carotol
Me
- Formation of diterpenes (examples)
Me
Me
OH
labdadienol
Me Me
Me Me Me Me Me
OPP
Me pimaradiene
geranylgeranyl-OPP Me
Me Me
Me
kaurene
Me Me
- Biosynthesis of squalene
Enz-Nu
Me Me
OPP Me Me
-Enz-Nu
farnesyl-OPP PPO
Me Me
Me Me
Me Me Me Me Me Me Me
Me
PPO
Me Me Me Me Me Me Me Me
NADPH
Me Me Me
Me
Me
Me Me Me
squalene
- Biogenesis of steroids and triterpene alcohols (examples)
Me Me Me
Me
Me squalene
Me Me Me
epoxidation
Me
Me
Me
H
Me Me
Me H
HO
Me H Me
+
H O
2,3-epoxysqualene
-H
Me Me
Me H
Me
Me Me Me
Me H Me
Me
Me H HO Lanosterol
Cholesterol Me Me
H H
HO
- Biogenesis of phenols through polyketides
Claisen-type
condensation itteration
CH3COSCoA CH3COCH2COSEnz
O Me O Me
O O O O
Aldol C6-C1
CoA O O HO OH
Me 7 1 S
6 2
polyketide
O OH
Aldol C2-C7 floroacetophenone
OH
O Me
HO Me
hydrolysis
SCoA
orsenilic acid
-H2O COOH
O O
OH
- Biogenesis of phenols: other examples
OH OH
O O O
HOOCCH2COSEnz
CoA
Me S
-CO2
Me O O Me O O
Senz
O
Aldol
Me O Me OH
Senz COOH salicylic acid
O
O O O
CoA OH O O OMe O O
S
methylation Me
Me
O
HO OH MeO OMe
O
Me eugenone
- Biogenesis of phenols through shikimic acid. Biosynthesis
of shikimic acid
O OP
OH
COO PO COO
+ PO
O
O HO OH
OH
OH
HO COO COO
-H2O NADPH shikimic acid
O OH HO OH
OH OH
- Biosynthesis of aromatic amino acids through shikimic
acid
COO COO OP
+ H
PO COO
O COOH
PO OH PO
OH OH
NH2
COOH
COO OOC COOH
[3,3]-Claisen O phenylalanine
O COOH
OH OH
NH2
chorismic acid prephenic acid
COOH
tyrosine
OH
- An overview of catabolic
pathways
- Metabolism of fatty
acids
- Metabolism of glucose (glycolysis)
- Conversion of pyruvate
to acetyl coenzyme A
- Anabolism of fatty acids
from CH3COSCoA
- Anabolism of glucose
(gluconeogenesis)
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