Trịnh Huy Cường

Đặng Nguyễn Minh Khôi

Natural
Products

There is a chemical rule that like dissolves like

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 Contents

Introduce
Part 1

The Process Selection

Part 2

Extraction techniques
Part 3
 Chemical characteristics

 What are “Natural Products”?

Naturally-occurring small organic compounds
• including heterocyclic compounds, and peptides.
• does not include proteins, carbohydrates, and nucleic acids.
• MW: ~150 ~ <800 amu (“small molecule”)
• Methods of extraction and purification are generally
similar to the techniques used for organic compounds
 (e.g., TLC, column chromatography, HPLC, GC)
• Methods of structural determination
• NMR, MS, IR, X-ray, UV
 Biological characteristics

 What are “Natural Products”?

• Compounds are generally characteristic of a particular species
or family, i.e., narrow taxonomic distribution (non-ubiquitous)
• 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)
• but many still have unknown function in the organism in which they are
found.
• Classified as “secondary metabolites” in contrast to “primary
metabolites”
 Introduce
• Diverse aspects of the Chemistry of Natural Products:
Structural determination of natural products compounds
• Total synthesis or semi-synthesis of natural products; enzyme
synthesis
• Determination of biosynthetic pathways using using plant
tissues, cell culture and isotopic labeling
• Pharmaceutical science: pharmacologic effects
• Functional foods, herbal medicines
• Agricultural science: antipest, allelopathy, IPM
• Ethnobotany
• Plant chemistry and plant development
• Biodiversity and Ecology; Marine natural products
• Chemotaxonomy and genetic classification
• Genomics and metabolonomics
 Why study Natural Products?

• Natural products are the source of the most complex and

fascinating chemical structures.
• Natural products represent biological diversity.
• Natural products are expressions of the genome.
• Natural products represent natural biological activity, whether as
single compounds or as complex mixtures.
• Natural products 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.
• Natural products can be an effective bridge from tradition to
modern scientific developments, including genetics, molecular
biology, biotechnology, and pharmaceutical science.
Range of products from natural products
Range of products from natural products
 Introduce

The Changing Landscape of Herbal Medicine,

Food and Wellness
• Herbal Medicine
• Dietary Supplement
• Nutriceutical
• Functional Food
 Natural Products Chemistry
is key to all of these!
 Natural products and Ecology

Animals
Antifeedant
Toxins
Toxins
Scents
Antipest
Attractants Toxins
Allelopathy Plants Insects Pheromones
Communication Communication

Antifungals
Symbiosis Symbiosis

Antifungals Chemotaxis
Chemotaxis Bacteria Communication
Communication
Fungi Antibacterials
 Contents

Introduce
Part 1

The Process Selection

Part 2

Extraction techniques
Part 3
 The process selection

1. Small molecular weight organic

compounds, lyophilic
Extract and
separate
compounds
2. Small molecular weight organic
compounds, hydrophilic
 The process selection

 Small molecular weight organic compounds, lyophilic

• Sythetic, the product is mixture ( 3 compounds)

 Using chromatographic method to separate

• Natural products, the isolation is more complex.

 Preparing a series of “extracts solid ”with polarization which

gradually increased
 The process selection
Common solvent Solubility Common chemical grouping

Petroleum ether Alkan

Hexan Alken, alkin
The solvent has polarization

Aromatic compound
which gradually increased

Benzene
Ether
Toluen
Diclorometan Aldehyde, cetone

Cloroform Ester, Amide

Ethyl acetate
Hydroxy, Amin
Etanol
Metanol
Butanol Acid cacbonxylic
Water
The process selection

Sơ đồ 1

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 The process selection

 Small molecular weight organic compounds, hydrophilic

• 95% new compounds are lyophilic

 Isolating hydrophiclic organic compound is more complex

than lyophilic ones
The process selection

Sơ đồ 2

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 Contents

Introduce
Part 1

The Process Selection

Part 2

Extraction techniques
Part 3
 1.Liquid-Liquid Extraction

• Liquid-liquid extraction (also known as solvent extraction)

involves the separation of the constituents (solutes) of a liquid
solution by contact with another insoluble liquid.

• Solutes are separated based on their different solubilities in

different liquids.

• Separation is achieved when the substances constituting the

original solution is transferred from the original solution to
the other liquid solution
1.Liquid-Liquid Extraction
1.Liquid-Liquid Extraction
 1.Liquid-Liquid Extraction

Two phase system, hydrophobic (top) and hydrophilic

(bottom) for measuring the partition coefficient of compounds.
1.Liquid-Liquid Extraction

Video
2.Solid-Liquid Extraction
1.Percolation
 2. Maceration

1 2

3 4
3.Soxhlet extractor

1: Stirrer bar
2: Still pot (the still pot should not be
overfilled and the volume of solvent in
the still pot should be 3 to 4 times the
volume of the soxhlet chamber)
3: Distillation path
4: Thimble
5: Solid
6: Siphon top
7: Siphon exit
8: Expansion adapter
9: Condenser
10: Cooling water in
11: Cooling water out
3.Soxhlet extractor
4.Kumagawa extractor

1: Condenser

2: Power saving cage

3: Solvent chamber

3
5. Steam distillation
6.Supercritical fluid extraction
6.Supercritical fluid extraction
7.Solid phase
 Some tips when isolating organic compounds

1. Dry the sample

- Compounds in extract materials will be stable

- To properly calculate the extract efficiency of the extract materials

- To continue refining high with column chromatography

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 Dried by inert gas in the Rotavap/rotovap

- Using the Evaporation to dry the

sample completely

- Give a slightly inert gas from the top

of the machine (N2)

- If not, saving sample longer in the

machine
 Dried by vacuum dessicator

- Using pump to remove the air from

the tank (30 - 60 minutes)

- Note: Replace desiccant for high

efficiency
Dried by lypophilization
 Recrystallization

- Purity of compound must be > 95%

- Investigating chemical structure of

substance by physiological method

 Fractional recrystallization

- Separate a substance based on different solubility in the same solvent

 Colding temperture recrystallization

When a compound has high content. It is able to get by colding temperture

 Colding temperture recrystallization

Gossypol collects from the kernel of cotton balls

Colding temperture recrystallization

Naringin is obtained from grape skins

Colding temperture recrystallization

Piperin collected from pepper

Colding temperture recrystallization

Capsanthin collected from red peppers

There is a chemical rule that like dissolves like

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