Introduction to Natural Products Chemistry

 Natural

product is a chemical compound or substance produced by a living organism (plants, marine organism, microorganism)  NP usually has a pharmacological or biological activity for use in pharmaceutical drug discovery and drug design.

Introduction to Natural Products Chemistry 
NP

can be considered as such even if it can be prepared by total synthesis.  NOT ALL natural product can be fully synthesized and many NP have very complex structures that are too difficult and expensive to synthesize on an industrial scale.  Not fully synthesized is equivalence to partially synthesized.

Introduction to Natural Products Chemistry 
Yang

dimakan normal drug totally synthesized too much chemicals traditional 

Naturally

synthesized medicine.

plants. building materials. insects. fungi. animals produce a large variety of organic compounds. e. dyes. lichens. medicinals. . foodstuffs.  Many substances were obtained anciently.g.Introduction to Natural Products Chemistry  Cells of organisms . bacteria. and other extracts from nature.

such as indigo and alizarin.Introduction to Natural Products Chemistry  Crude aqueous extracts of certain plants (and animals) provided pigments. .

Introduction to Natural Products Chemistry  Other examples of natural products: ephedrine from Ephedra sinica (respiratory ailments) tetrahydrocann abinol (marijuana)geraniol (rose oil) cinnamaldehyde (cinnamon)diallyl disulfide (garlic)   .

and form the foundation for folk medicine. Plants and animals have provided substances used for their biological activity.Introduction to Natural Products Chemistry   Mild heating of certain plants afforded perfumed distillates. . Most natural products have usually come from plants and microorganisms due to practical difficulties in extracting them from animals. to heal or to kill.

Their biosynthetic paths are known (acetate. and salts. and produce a wide variety of compounds. phosphorus compounds.shikimate/shikimic. and mevalonate pathways) .Introduction to Natural Products Chemistry     Plants are particularly interesting because: They have the broadest spectrum of biosynthetic capability. carbon dioxide. nitrogen (elemental and in salts). They use simple starting materials: water.

 They discovered that natural extracts had more complex compositions and properties than salts and minerals. chemists moved from myth and mystery to basics of modern scientific methods to begin to uncover the true properties of natural extracts from biological systems.Introduction to Natural Products Chemistry  In the late 1700's. .

Introduction to Natural Products Chemistry   This lead Berzelius. e.("Organic" substances were believed to be obtainable only from organs of living systems and could not be man-made because only living systems have the vital ("life") force. organic chemistry was exclusively the study of natural products.g. to distinguish between "inorganic" and "organic´. mineral. sources. in 1807.) In the 1800's. "Inorganic" materials were from non living. .

which were then purified and analyzed. synthetic methods were being developed for some of these natural compounds.  In the late 1800's. Some examples of natural products and when they where discovered are as follows: .Introduction to Natural Products Chemistry  Natural extracts were subjected to separation into component compounds.

Introduction to Natural Products Chemistry    morphine (narcotic analgesic) 1817 Isolated from papaver somniferum Analgesic effects .

taxus brevifolia or named as taxol.Introduction to Natural Products Chemistry Paclitaxel (taxol)   Isolated from pacific yew tree. Used in cancer chemotherapy (anticancer) .

Introduction to Natural Products Chemistry    strychnine (poison) 1818 Very toxic Used as pesticide .

Introduction to Natural Products Chemistry Penicilin  Discovered by Alexander Fleming (1928)  Isolated from culture broth of penicilium notatum  Antibacterial therapeutic. .

formerly Vinca rosea.Introduction to Natural Products Chemistry Vincristine   Isolated from the Catharanthus roseus. . Used in cancer chemoteraphy.

An anti fever agent especially useful in treating malaria. .Introduction to Natural Products Chemistry Quinine   Isolated from cinchona tree.

palythoa toxica.Introduction to Natural Products Chemistry Palytoxin (1971)  Isolated from soft coral . .

Introduction to Natural Products Chemistry   cocaine (narcotic stimulant) 1859 nicotine (toxic) 1828 .

 Uses of lead compound : Can be produced by total synthesize.  .Introduction to Natural Products Chemistry  Some medicines are developed from a lead compound originally obtained from a natural source.  Can act as a template for a structurally different total synthetic compound.  Can be a starting point (precursor) for a semi-synthetic compound.

.Introduction to Natural Products Chemistry   Most biologically active natural product compunds are SECONDARY METABOLITES with very complex structures.  It may allow the possibility of synthesizing analogues of the final product. This approach can have 2 advantages :  The intermediate may be more easily extracted in higher yield than the final product itself.

Introduction to Natural Products Chemistry 10-deacetylbaccatins  isolated from the Pacific yew tree (Taxus brevifolia) 10-deacetylbaccatin III  Used as chemical intermediate in the preparation of anti cancer. .

Introduction to Natural Products Chemistry General isolation strategy of natural products: .

Introduction to Natural Products Chemistry Extract the dried and ground plant material with a suitable solvent. Natural organic acids were isolated by aqueous basic extraction and natural organic bases (alkaloids) were isolated by aqueous acidic extraction.  Separate and purify each component. early isolations involved selective crystallization of the most dominant component in the mixture.  Concentrate the extract. .   Since the concentrate contains an enormous variety of compounds. Liquid natural products were distilled.

paper. electrophoresis. GC. or from the biological action. Natural products are usually given names that are derived from the species name of the plant or animal. or property. of the compound. TLC.Introduction to Natural Products Chemistry   Modern chromatographic methods have been greatly developed to isolate and purify a large number of different compounds in very small quantities: column. . etc. ion exchange. HPLC.

hoping to find correlations between data and structure. but useful data on natural products were obtained.Introduction to Natural Products Chemistry  In the late 1800's. . [a] (optical rotation). This initiative was not successful in predicting structure. natural products were identified and analyzed by mp. bp.

B. C) and the entire molecule (A-B-C)  Classification of the compound into a biogenetic family of compounds .Introduction to Natural Products Chemistry Classical structural elucidation is done by:  Determination of functional groups  Determination of the carbon skeleton and the location of the functional groups  Degradation to smaller fragments (A-B-C ------> A + B + C)  Elemental analysis  Reactivity (leading to new reactions)  Stereochemistry  Synthesis of the smaller fragments (A.

W.Introduction to Natural Products Chemistry             More modern structural elucidation and characterization by spectroscopy: 1930's UV (ultraviolet) light (cf.II) 1950's NMR (nuclear magnetic resonance) spectroscopy 1960's MS (mass spectrometry) ESR (electron spin resonance) spectroscopy and by other methods: ORD (optical rotatory dispersion) CD (circular dichroism) acidity and basicity measurements (pK) advanced synthetic and biosynthetic technology X-ray crystallography . Woodward's Rules. 1941) 1940's IR (infrared) spectroscopy (note: penicillin structure problem in W.

Why synthesize natural products? Structure determination Challenge Develop new synthetic methods Practical and commercial interests . so much less material is required.Introduction to Natural Products Chemistry       Modern methods reduces the necessity of chemical degradation methods.

 Natural product sources  Part of plants Rhizomes  Flowers  Leaves  Stem barks  Fruits  Roots  .Introduction to Natural Products Chemistry  Many of today¶s medicines are obtained directly from a natural sources.

Introduction to Natural Products Chemistry  Microorganism Bacteria  Fungi   Marine Coral  Sponges  Marine microorganism  .

structurally diverse chemical compounds.  The study of medicines derived from natural sources.  .  Pharmacognosy Provides the tools to identify.Introduction to Natural Products Chemistry  Crude extract from any one at those sources typically contains novel/new. select and process natural products for medicinal use.

Introduction to Natural Products Chemistry  Usually. . the natural product compound has same form of biological activity and that compound is known as the active principle such a structure can act as a lead compound (guided compound).

.  Examples  An antimicrobial compounds works well with compounds that stimulate various pathways of the immune system.Introduction to Natural Products Chemistry  Isolated  compound Often work differently than the original products which have synergies and may combine.

 The . synthetic drugs cause severe side effects that were not acceptable except as treatments of last resorts for terminal diseases such as cancer.Introduction to Natural Products Chemistry  Many non-natural. metabolites discovered in medicinal.

: semisynthetic procedures which involves harvesting a biosynthetic intermediate from the natural source.Introduction to Natural Products Chemistry  In the developed world almost all clinically used chemotherapeutics have been produced by intro chemical synthesis.  Alternative . Exceptions for complex compounds such as taxol and vincristine.

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