CHEMISTRY OF NATURAL PRODUCTS ppt

Metabolism of fatty acids 4.. Metabolism of glucose glycolysis 5.. Anabolic pathways of fatty acids and carbohydrates... Biosynthesis of acyclic terpenoidsOPP Me Me CH 3 COSCoA Claisen-t

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

CH 3 COSCoA

Claisen-type condensation

CH3COCH2COSCoA

Aldol-type condensation

2 NADPH 2 NADP 3 ATP 3 ADP

Me OP

O

CO2, 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

OPP

Me

OPP

- OPP

Me

α-terpinyl cation

Me

OH

Me

O

Me

limonene

fenchone

camphene 3-carene

geraniol

myrcene

Me Me

Me Me

Me Me

Me

CH2

Me Me α- and β-pinene enzyme

Formation of sesquiterpenes (examples)

OPP

Me

Me

Me

Me H

H

Me

Me Me

Me OH

bisabolene

cadinene

carotol

Formation of diterpenes (examples)

OPP geranylgeranyl-OPP

Me

Me

Me

kaurene

Me

Me

Me

Me

pimaradiene

Me

Me

Me

labdadienol OH Me

Biosynthesis of squalene

farnesyl-OPP

OPP

Me Me

Me Me

PPO

Enz-Nu

-Enz-Nu

Me Me

Me

PPO

Me

Me Me

Me Me

NADPH

squalene Me

Me

Biogenesis of steroids and triterpene alcohols (examples)

squalene Me

Me

O

H+

HO

Me Me

Me

Me

HO

Me

Me

Me H

Me H

Me H

2,3-epoxysqualene

epoxidation

Me

Me

H

H

H HO

Me Me

Lanosterol

Me Me

- H

Cholesterol

Biogenesis of phenols through polyketides

CH 3 COSCoA

Claisen-type condensation

CH3COCH2COSEnz itteration

O CoA

O O

O

1

Aldol C2-C7

O

O

OH

Me SCoA

Me

OH

HO

COOH

hydrolysis

orsenilic acid

Aldol C6-C1

Me O

O

O

O

Me O

OH

OH HO

floroacetophenone

polyketide

Biogenesis of phenols: other examples

HOOCCH2COSEnz

O CoA

O

O

Aldol

OH

OH

Me

O Senz

O Me

O Senz

Me

COOH

OH salicylic acid

S

O CoA

O

O

O

O

Me

Me

O O OH

O O OMe

eugenone

Biogenesis of phenols through shikimic acid Biosynthesis

of shikimic acid

O

COO

PO

O OH

OH +

PO

HO

OH OH

O COO

OP

COO HO

OH

OH O

COO

OH OH HO

shikimic acid

Biosynthesis of aromatic amino acids through shikimic

acid

COO

OH OH

PO

H +

COO

O OH

COO

OH

[3,3]-Claisen

OP

OH chorismic acid

O

prephenic acid

COOH

NH2

COOH

NH2

OH

tyrosine phenylalanine

An overview of catabolic

pathways

Metabolism of fatty

acids

Metabolism of glucose (glycolysis)

Conversion of pyruvate

to acetyl coenzyme A

Anabolism of fatty acids

Anabolism of glucose (gluconeogenesis)