Natural Products Chemistry Amir E. Wahba, Ph.D. Assistant Professor of Natural Products Chemistry Department Faculty of Science, Damietta University.

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Presentation transcript:

Natural Products Chemistry Amir E. Wahba, Ph.D. Assistant Professor of Natural Products Chemistry Department Faculty of Science, Damietta University

Instructor Dr. Amir E. Wahba Research Interest: Marine natural products, total synthesis of natural products, cancer chemotherapy, pseudo LDL nanoparticles for targeted delivery of cancer chemotherapy Contact: Office hours: Saturday, by appointment

What Are Natural Products?

What are Natural Products? Living organisms produces natural products for several reasons: Live Grow Reproduce Defense Communicate Examples of living organisms that produces natural products: Bacteria Fungi Plants Marine organisms (sponges, alga...etc)

How Do plants produces chemicals? Biosynthesis

Primary Metabolism: All the chemical reactions necessary for the live of the organism by itself. Primary Metabolites: All the chemical products involved in the Primary Metabolism. Secondary Metabolites: All the chemical products that are produced by the living organism but are NOT involved in the primary metabolism. Not necessary for the live of the organism by itself but useful for interaction with others (chemical communication, chemical defenses).

Biosynthesis: Building Blocks

Tetrahydrocannabinol Moderate analgesic

Terpenes Volatile oily compounds Usually give the smells of plants Essential oils All aliphatic compounds Biosynthetically obtained from isoprene unit

Terpenes: Classification Number of carbon atomsClass 10Monoterpenoids (C 10 H 16 ) 15Sesquiterpenoids (C 15 H 24 ) 20Diterpenoids (C 20 H 32 ) 25Sesterterpenoids (C 25 H 40 ) 30Triterpenoids (C 30 H 48 ) 40 Tetraterpenoids (Carotenoids) (C 40 H 64 ) >40Polyterpenoids

Terpenes: Isoprene Rule Isoprene rule:

Monoterpenoids and Sesquiterpenoids Isolation: Steam distillation Extraction with volatile solvents Structure Elucidation: Pure sample Molecular formula Mass spectrophotometer Chemical reactions Complete Structure: Chemical methods Modern Spectroscopy (IR, NMR, 2D-NMR)

Myrcene Acyclic monoterpenoid hydrocarbon Isolated from verbena and bay oils ( ورق الغار أو ورق موسى ) Used in perfume industry and as flavoring material in cooking Molecular formula: C 10 H 16

General Chemical Methods Catalytic hydrogenation: Ozonolysis

Structure Elucidation of Myrcene

Citral 60-80% in lemon grass oil Smell of lemons Molecular formula: C 10 H 16 O

Citral: Structure Elucidation laevulic acid

Citral: Structure Elucidation

Expected questions: Building blocks for the biosynthesis of natural products A chemical puzzle that describe the structure elucidation of a terpenoid