CNP 1

CHEMISTRY OF NATURAL
PRODUCTS
By
Mufti Dekamo (B Pharm, MSc)
2015, Sem 2
Natural Products
compounds which are isolated from natural sources like
plants, animals, fungi, bacteria and lichens.
the end product of organism metabolism (metabolites)

Primary metabolites:-essential for the plants growth and is
involved in directly normal growth, development, and
reproduction.
Secondary metabolites:-not directly involved in those processes

and usually has a function but is not that important for the
organism survival.
Chemistry of Natural Products 2
No nutritional or structural function.
Functional roles may include:
 color (identification)
 scent (attraction or repulsion)
 sexual attraction
 social communication
 defense (e.g., plant toxins and antibiotics)

Why do we study Natural Products?
 Source of the most complex and fascinating chemical

structures.
 Represent biological diversity.
 Are expressions of the genome.
 Represent natural biological activity, whether as single
compounds or as complex mixtures.

 Are part of the natural wealth of the country, and can be
an important source of livelihood, from agriculture and
food, pharmaceuticals, fine chemicals industry.
 Can be an effective bridge from tradition to modern

scientific developments, including genetics, molecular
biology, biotechnology, and pharmaceutical science.

The market for natural products is HUGE
• Pharmaceuticals
• Traditional herbal medicines
• Beverages: tea (e.g., green, Chinese), herbal teas, coffee
• Food supplements and health products
• Herbs and spices, food flavor ingredients
• Perfumes and scents
• Essential oils, others …

Herbal Medicine Regulation in the World
WHO recognizes the important and historical role of herbal

medicine in health.
Herbal medicine is a major form of treatment for more than 70% of

the world's population.

 The Guidelines for the Assessment of Herbal Medicines
states that a substance’s historical use is a valid way to
document safety and efficacy in the absence of
scientific evidence to the contrary.
• Appropriate use
• Quality control methods
• Recommended labeling

 EU follows the "doctrine of reasonable certainty” and is
generally consistent with WHO.
 France: traditional medicines can be sold with labeling

based on traditional use
 Germany considers active ingredient of herbal product

and standardization (Commission E).

 England generally follows the rule of prior use
 USA: herbal products can be marketed only as food

supplements.
 Herbal products can make no specific health claims
without FDA approval.
 India: Ayurvedic medicine

Asia: use of patent herbal remedies composed of dried and
powdered whole herbs or herb extracts, also in tablet form
China: wide-spread use of traditional herbals
Japan: Kampo medicine is derived from Chinese medicine

The changing landscape of herbal medicine, food
and wellness
Traditional Medicine “is a comprehensive term used to

refer both to TM systems and to various forms of indigenous
medicine.

In countries where:
• the dominant health care system is based on
allopathic medicine, or
• where TM has not been incorporated into the
national health care system,
TM is often termed “complementary”, “alternative” or
“non-conventional” medicine.”
eg, US FDA: Complementary and Alternative Medicine

Chemistry Natural Products is key to
•Herbal Medicine
•Dietary Supplement
•Nutriceutical
•Functional Food

Herbal Medicine: Makes therapeutic claim;
includes:
 crude herbal materials,
 preparations and finished products, that contain

as active ingredients,
 parts of plants or combinations thereof.
(WHO).
In Europe, also called “phytotherapy”.

Dietary Supplement: A product that is intended to
supplement the diet and that bears or contains one or more of
the following dietary ingredients:
• a vitamin,
• mineral,
• herb or other botanical material,
• an amino acid,
a dietary substance to supplement the diet by increasing the

total daily intake.
Nutriceutical: Dietary supplements administered in large
dosages in order to obtain pharmacological effects.
Deliver a concentrated form of a presumed bioactive agent

from food, presented in a non-food matrix, in dosages that
exceed those that can be obtained in normal food.

•Functional Food: A food that is consumed as part of a
normal diet and which is claimed to have health-promoting
or disease-preventing properties beyond the basic function
of supplying nutrients.
 Examples include probiotics (fermented foods with
live cultures), prebiotics (e.g., inulin).

The study of natural products is multidisciplinary
Biology   Chemistry
Taxonomy . Botany Organic synthesis
Agriculture . Pharmacology . Pharmaceutical Science . Organic analytical chemistry
Entomology . Microbiology . Biotechnology/Molecular Biology . Biochemistry
Genomics . Proteomics
Metabolonomics

Natural products and Ecology
Animals
Antifeedant
Toxins
Toxins
Scents
Antipest
Attractants Toxins
Allelopathy Plants Insects Pheromones
Communication Communication
Antifungals
Symbiosis Symbiosis
Antifungals Chemotaxis
Chemotaxis
Fungi Bacteria Communication
Communication Antibacterials

Techniques used in natural products chemistry
1800 1850 1900 1950 1975 2000
Type of research undertaken:

Isolation, characterization
Pharmacognosy & Pharmacology
Organic synthesis
Chromatography Spectroscopy
Biogenetic studies
Biochemistry; Enzymology
Molecular Biology
Metabolonomics
Techniques used:
basic physico-chemical measurements
TLC column chrom GC HPLC / Electrophoresis
X-ray UV-vis IR MS / NMR
Radioisotopes
Enzymes Computational methods
Tissue culture
Mol Bio / Biotech
Combinatorial chem

Modern directions in natural products chemistry:
• Genomics of bacteria and plants
• Novel and efficient synthetic methods
• Genetic engineering of bacteria and plants
• Enzyme synthesis

•Computational methods and modeling
• High efficiency chromatography
• Spectroscopic methods
• High-throughput screening
• Synergism
• Biotransformation

The development of methods in organic chemistry is
linked to developments in natural products chemistry:
1800s
• Development of techniques in organic chemistry
• Wagner-Meerwein rearrangement in monoterpenes
early 1900s
• The early work on alicyclic chemistry was done on
steroids

1950~1980
Steric control of chemical reactions, e.g., borneol, steroids
Studies by UV-visible spectroscopy (e.g., Vitamin A )
Development of NMR (2-D NMR, NOE)
1980 ~ present
Recent synthetic methodologies
Enzyme-mediated synthesis, cell culture, genetics and

biotechnology

The role of the study of natural products today
• Nature still holds many secrets which we can learn from:
chemical structure, biosynthesis, the role and relationship
of plants to other organisms.
• The study of natural products merges science with
culture.
• For countries which harbor rich biodiversity, the study of
natural products is an important way of developing one’s
natural resources.
• Natural products should use the new developments, e.g.,
molecular biology, computational science.

Issues and challenges in Natural Products today
1. Loss of biodiversity
2. Intellectual Property Rights
• Patent protection (pharma companies)
• Biopiracy (source countries)
3. Western drugs:
a. High cost of drug development
b. New drug leads and targets
4. Herbal products:
a. Regulation
b. Improvement in quality
c. Elucidation of mechanism of action

Research areas in natural products today
1. Structural elucidation
2. Metabolonomics
3. Synergy and biotransformation
4. Biosynthesis
5. Biological activity
a. Ecological
b. Pharmaceutical properties / drug discovery
c. Healthcare and cosmetic products
6. Molecular biology and Biotechnology
7. Quantitative natural products chemistry

CNP is at the intersection of many fields:
Ecological Biochemistry
Taxonomy
Pharmaceutical Science
Entomology
Biochemistry
Natural
Products Combinatorial
Chemistry Chemistry
Biotechnology
Chemical synthesis
Molecular Biology Microbiology

Major classes of organic natural products
 Peptides and proteins  Steroids

(basically consist of  Terpenes (Terpenoids)
amino acids)
 Carteins (Carotenoids)
 Fats and oils
 Anthocyanines
 Nucleotides (purines)
 Alkaloids
 Vitamins

LITERATURES
latest available edition of the following books
1.Finer, I, L., “Organic chemistry”, vol 2, Pearson Education Ltd,

Delhi.
2.Hesse, M, “Alkaloid chemistry”, John Wille and Sons, New York.
3.Shoppe, C, W., “Chemistry of the steroids”, Butter worth, London.

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CHEMISTRY OF NATURAL

the end product of organism metabolism (metabolites)

Secondary metabolites:-not directly involved in those processes

Chemistry of Natural Products 3

 Source of the most complex and fascinating chemical

Chemistry of Natural Products 4

 Can be an effective bridge from tradition to modern

Chemistry of Natural Products 5

Chemistry of Natural Products 6

WHO recognizes the important and historical role of herbal

Herbal medicine is a major form of treatment for more than 70% of

Chemistry of Natural Products 8

Chemistry of Natural Products 9

 France: traditional medicines can be sold with labeling

 Germany considers active ingredient of herbal product

Chemistry of Natural Products 10

 USA: herbal products can be marketed only as food

 India: Ayurvedic medicine

Chemistry of Natural Products 11

China: wide-spread use of traditional herbals

Japan: Kampo medicine is derived from Chinese medicine

Chemistry of Natural Products 12

Traditional Medicine “is a comprehensive term used to

Chemistry of Natural Products 13

Chemistry of Natural Products 14

Chemistry of Natural Products 15

 preparations and finished products, that contain

In Europe, also called “phytotherapy”.

• herb or other botanical material,

a dietary substance to supplement the diet by increasing the

Deliver a concentrated form of a presumed bioactive agent

Chemistry of Natural Products 18

Chemistry of Natural Products 19

Taxonomy . Botany Organic synthesis

Agriculture . Pharmacology . Pharmaceutical Science . Organic analytical chemistry

Entomology . Microbiology . Biotechnology/Molecular Biology . Biochemistry

Chemistry of Natural Products 20

Chemistry of Natural Products 21

Type of research undertaken:

Chemistry of Natural Products 22

• Genomics of bacteria and plants

• Novel and efficient synthetic methods

• Genetic engineering of bacteria and plants

Chemistry of Natural Products 23

• High efficiency chromatography

Chemistry of Natural Products 24

Chemistry of Natural Products 25

Steric control of chemical reactions, e.g., borneol, steroids

Studies by UV-visible spectroscopy (e.g., Vitamin A )

Development of NMR (2-D NMR, NOE)

Recent synthetic methodologies

Enzyme-mediated synthesis, cell culture, genetics and

Chemistry of Natural Products 26

Chemistry of Natural Products 27

Chemistry of Natural Products 28

Chemistry of Natural Products 29

Molecular Biology Microbiology

Chemistry of Natural Products 30

 Peptides and proteins  Steroids