CHEMISTRY OF NATURAL PRODUCTS

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Overview1.Biosynthesis of terpenes2.Biosynthesis of phenols3.Metabolism of fatty acids4.Metabolism of glucose (glycolysis)5.Anabolic pathways of fatty acidsand carbohydrates.Biosynthesis of acyclic terpenoids.Condensation of isoprene units. Formation of acyclic terpenes.Formation of monoterpenes(examples)

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Nội dung Text: 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 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)