PHYTOCHEMICALS

Phyto comes from the Greek word

means plant.
Phytochemicals
Chemicals

Chemicals present naturally in plants

Phytochemicals include secondary plant metabolites:

Essential oils
Oleoresin
Bioactive compounds
Phenolic compounds-flavonoids
Glycosides
Alkaloids
PLANT LIPIDS

 Defined as substances that can be extracted

from cells & tissues by nonpolar organic
solvents.

 Devided into two major classses:

1) Simple lipids
2) Complex lipids
 Simple lipids
1) Steroids
2) Prostaglandins
3) Terpenoids
4) Fat-soluble vitamins
 Those that are not easily hydrolysed by
aqueous acid or base
 Seem inappropriate because many so-called
“simple” lipids are quite complex molecules
 Steroids

CH3
H
CH3 H

H H
HO
Cholesterol

- Common biological intermediate

- Believed to be the biosynthetic
precursor to other steroids
 Prostaglandins
O H
COOH

H
HO H OH

PGE1

- Prostaglandins – first isolated from secretion

of prostate gland
- regulate diverse functions
eg: blood pressure, blood clotting, allergic,
inflammatory etc.
 Triglicerides
Complex lipids
Waxes

- Those that easily hydrolysed to simple constituents

- Mostly esters of long-chain carboxylic acids called
fatty acids
 Trigliseride

- Esters of gliserol
- Liquid (oil)
- Solid (fat)
O
CH2 O C (CH2)16CH3
O
CH O C (CH2)16CH3
O
CH2 O C (CH2)16CH3

Tristearin (a fat)
 Waxes
- Esters of long chain fatty acids with long chain
alcohols
- Serve a number of purposes in plants & animals
eg: Beeswax – a mixture of waxes that bees use to
form their honeycomb
O
CH3(CH2)29 O C (CH2)24CH3

(a component of beeswax)

- Carnuba waxes – secreted by carnuba plant to

coat its leaves to prevent excessive loss of water by
evaporation
 BIOSYNTHESIS OF PHYTOCHEMICALS
PO43-

CO2 + H2O Nucleic Acid

Photosynthesis
Carbohydrates Tannin Flavonoids

O OH O OH Phenylpropanoids

Aromatic
O
Amino
HO OH
OH OH Acids
OH
Shikimic Acid Chorismic Acid N2
CH3COCOOH
Pyruvic acid Amino Protein
Acid Peptides
CH3COOH OH Alkaloids
Acetic acid
CH3CCH2COOH
Terpenes
Fatty Acids & CH2CH2OH Steroids Purines
Polyketides Mevalonic acid
 ESSENTIAL OILS

 Volatile aromatic compounds obtained

via steam or hydrodistillation

 Mainly terpenes and terpenoids

(mono and sesqui)

 Some esters and alcohols

Concretes
- Solvent extracted product contains volatile &
non volatile components

Absolutes
- Ethanol soluble concretes

Oleoresin
- Solvent extracted product

Tincture
- Product obtained by soaking dry plant materials
in 50-95% ethanol in a ratio of 1:5
(herbs material : solvent)
TERPENOIDS

 Natural products derived from mevalonic acid

 Consist of isoprene units - C5

 Contain oxygen in variety of functional groups

• Alcohol
• Ketone/ aldehyde
• Ester
• Ether
• Carboxylic acids
 Subdivided/ classified according to the number of carbons
•mono, sesqui, di, tri, tetra, etc.
 CLASSIFICATION OF TERPENOIDS

MONOTERPENOIDS C10 Skeleton

Essential Oils
SESQUITERPENOIDS C15 Skeleton (aroma)

DITERPENOIDS C20 Skeleton

TRITERPENOIDS C30 Skeleton (Steroids skeleton)

TETRATERPENOIDS C40 Skeleton

ß-carotene  pigment in carrot  Vitamin A

Lycopene  pigment in tomato
ESSENTIAL OILS

Source Components
Perfumes & Flowers Mixture of Terpenes &
Flavours Terpenoids
Oil of Celery Celery β - Selinene

Oil of anise Anise Seed MeO

Anethole

Oil of Coriander Coriander seed OH

Linalool

Mango flavour Curcuma mangga

Myrcene
CONSTITUENTS OF ESSENTIAL OILS & ESSENTIAL OIL DRUGS

MONOTERPENOIDS - ALCOHOL

OH

OH OH

geraniol (-)-linalool (-)-β-citronellol

HO

HO
OH

(-)-β-menthol (+)-Borneol (+)-α-terpineol

 KETONES

Used in liniments against rheumatic pains

O

~ 3% solution in ethanol sooth itching

(+)-camphor

CHO

(+)-carvone (+)-limonene Citral

- From caraway - From lemon, orange, grape fruit - from ginger

- used as spice - For flavouring - For flavouring
- Food & perfumery industries
 PHENOLS

Thymol
Thymi herba
Carvacrol The extract is used in cough mixture as an expectorant

PHYRETROIDS
- Flower of Chrysanthimum sp.
- Insecticides

O
O

O
Pyrethrin
 ALKALOIDS

1. Contain nitrogen, N–usually derived from amino acids

2. Bitter tasting, usually in the forms of solids/ crystals
3. Precipitate with heavy metal iodides.
4. Testing the presence of alkaloids.
- Mayer’s reagent ( Potassiomercuric iodide solution).
Cream coloured precipitate.
- Dragendoff’s reagent (solution of potassium bismuth iodide).
Orange coloured precipitate.
5. Alkaloids are basic-form water-soluble salts.Most alkaloids are
well defined crystalline substances, which react with acids to
form salts. In plants, they may exist :
- as free state
- as salts
- as N-oxides
 AlKALOIDS

Cocaine – local anaestatic

Nicotine – alkaloid from tobacco

N
CH3 RO
N

Morphine – Analgesic O H H
Codeine – Analgesic, NCH3
antitussive
HO
Morphine, R=H
Codeine, R=CH3
Vincristine & vinblastine – anticancer
From Catharanthus roseus (Kemunting Cina)

Terpenes/ steroids also build into final alkaloid skeleton

 GLYCOSIDES

Glycosides are compounds containing carbohydrates and

noncarbohydrate residue in the same molecule

The carbohydrate residue is attached by an acetyl

linkage at carbon atom 1 to a noncarbohydrate residue
or AGLYCONE

The nonsugar component is known as the AGLYCONE.

The sugar component is called GLYCONE

If the carbohydrate portion is glucose, the resulting

compound is a glucosides
 Example

Methyl glucoside will be formed when a solution of glucose

in boiling methyl alcohol is treated with 0.5 % HCl as catalyst

CH2OH CH2OH
O O
0.5 % HCl
OH CH3OH OH

HO OH HO OCH3
OH OH
Glucose Methyl Glucoside
 or   or 
 CLASSIFICATION OF GLYCOSIDES

GLYCOSIDES

Tannin Flavonol
Saponin group
Carboxylic Phenol
group Alcohol group group
Aldehyde group Lactone Isothiocyanate
group group group
Anthraquinone Cyanate
group group

SAPONIN GLYCOSIDES

 Saponin glycosides are devided into 2 types based on the chemical structure of
their aglycones (sapogenins)
E.g. : Dried rhizome and root Glycyrrhiza glabra (licorice) from Leguminosae
family.
 SAPONIN

Aglycone
Glycone

Sapogenin
Sugar
-Glucose
- Arabinose
- xylose - Neutral - Saponin Acid
- glucronic acid Saponin - Triterpenoids
- Steroids

The main pathway leading to both types of sapogenins is similar

and involves the head to tail coupling units. However, a branch
occurs, after the formation of the triterpenoids hydrocarbon,
squalene, that leads the steroids in one direction and to cyclic
triterpenoids in the other.
 PHENOLIC

 Most phenolic compounds belong to the flavonoids.

 Lignin the primary substances of wood is the most

common member of this group