Different solvents can be used

for extraction depending on the

type of phytochemicals being
targeted for extraction.
Solvents differ in polarity just
like phytochemicals.
 Principles of Polarity:
 The greater
the electronegativity difference
between atoms in a bond, the more
polar the bond. Partial negative
charges are found on the most
electronegative atoms, the others
are partially positive.
 Ingeneral, the presence of
an oxygen is more polar
than a nitrogen because
oxygen is more
electronegative than
nitrogen.
 Thecombination of carbons
and hydrogens as in
hydrocarbons or in the
hydrocarbon portion of a
molecule with a functional
group is always NON-
POLAR.
Polar solvent Non-Polar
solvent – water solvent - hexane

ö CH3CH2CH2CH2CH2CH3
H H
O= 3.5 C= 2.5
H= 2.1 H= 2.1
Diff.= 1.4 Diff.= 0.4
 Amide(RCONH2) >
Acid(RCOOH) > Alcohol (ROH)>
Ketone (RCOR)~
Aldehyde(RCHO) > Amine
(RNH2 )> Ester (RCOOR) >
Ether (ROR)> Alkane (RH)
 A.polar solvents – e.g. water,
ethanol, ethyl alcohol , hexane

H2O CH3CH2OH
water ethanol (IUPAC)
ethyl alcohol (common)
 B.medium polar solvents - e.g.
acetone, ethyl acetate and
dichloromethane

CH3COCH3 CH3COOCH2CH3
acetone ethyl acetate
CH2Cl2
dichloromethane
C.non-polar solvents – e.g. toluene,
chloroform, hexane
CH2
CH3 H2 C CH2

CHCl3 H2 C CH2
CH2
toluene chloroform hexane
 These solvents can be mixed or
used in sequence for the same
sample material.
Solubility follows the general
rule:
“Like dissolves like.”
Polar solutes dissolve in polar
solvents.
Non-polar solutes dissolve in
non- polar solvents.
Major Types Of Chemical Compounds
In Plants & Animals
Phenolic Compounds,
Phenolic Compounds: Composed
of one or more aromatic benzene
rings with one or more hydroxyl
groups (C-OH). This enormous
class includes numerous plant
compounds that are chemically
distinct from terpenes.
Although the essential oils are
often classified as terpenes,
many of these volatile chemicals
are actually phenolic compounds,
such as eucalyptol from
(Eucalytus globulus), citronellal
from (E. citriodora) and
 clove oil from Syzygium
aromaticum.Like the terpenes, many
phenolic compounds are attached to
sugar molecules and are called
glucosides or glycosides, depending
on the type of sugar. Most vanilla
flavorings sold in markets are
synthetic vanillin containing artificial
food coloring and preservatives.
Vanillin is a single-ring phenolic
compound derived from the
breakdown of lignin, a complex
phenolic polymer that gives
seasoned wood its color, hardness
and mass. Natural vanilla flavoring
also comes from vanillin plus
several other aromatic compounds
in the seed capsules of the vanilla
orchid (Vanilla fragrans).
 Thedouble-ring phenolic
compound called coumarin
imparts the distinctive sweet smell
to newly-mown hay. Coumarin is
also an anticoagulant that
represses the synthesis of
prothrombin, a plasma protein
produced in the liver in the
presence of vitamin K.
 Prothrombin is the precursor of
the enzyme thrombin which
catalyzes the conversion of
fibrinogen to fibrin in the
clotting process. Threads of
fibrin wind around blood
platelets in the damaged area of
a blood vessel and provide the
framework of a blood clot.
 Flavonoids are widely distributed
in plants fulfilling many functions.
 Flavonoids are the most
important plant pigments for
flower coloration producing yellow
or red/blue pigmentation in petals
designed to
attract pollinator animals.
 In higher plants, Flavonoids
are involved in UV filtration,
symbiotic nitrogen fixation
and floral pigmentation.
 They may act as a chemical
messenger or physiological
regulator, they can also act as
cell cycle inhibitors.

 Flavonoids secreted by the root of
their host plant help Rhizobia in
the infection stage of
their symbiotic relationship with
legumes like peas, beans, clover,
and soy. Rhizobia living in soil are
able to sense the flavonoids and
this triggers the secretion of Nod
factors
 , which in turn are recognized by
the host plant and can lead to
root hair deformation and several
cellular responses such as ion
fluxes and the formation of a root
nodule.
 Inaddition, some flavonoids
have inhibitory activity against
organisms that cause plant
disease e.g. Fusarium
oxysporum.
 Hemorrhaging and death may
occur in cattle that eat spoiled
sweet clover hay, depending on
the amount consumed.
Dicoumarin and related drugs are
used in human medicines as blood
thinners and are commonly used
in rodent poisons such as Decon®,
which literally cause rats to bleed
to death.
 Flavonoids include water soluble
pigments (such as anthocyanins)
that are found in cell vacuoles.
[Note: Carotenoids are fat soluble
pigments found in plastids.] You
have probably observed water
soluble anthocyanins if you have
cut open a fresh head of red
cabbage.
 [Note:The nitrogen-containing,
water soluble pigment in beets is
not a flavonoid, but a different
type of chemical called a
betacyanin or betalain, with a
complex chemical structure
similar to an alkaloid. Betacyanins
also produce the reddish color of
flowers such as Bougainvillea.]
 Water soluble flavonoids (mostly
anthocyanins) are responsible for
the colors of many flowers and
can range from red to blue,
depending on the pH of the
watery sap in the vacuoles
The common garden shrub
called hydrangea (Hydrangea
macrophylla ) produces showy
clusters of white, pink, red or
blue flowers depending on the
pH of the soil.
Bitter, alkaline, nitrogenous compounds
that may have pronounced effects on the
nervous systems of animals. They may
contain phenolic rings or terpenes
(steroids), and include one of the largest
groups of chemicals produced by plants.
 Some alkaloids are also
produced by animals, such as
toxins in the skin of poison-
dart frogs. Many alkaloids are
plant metabolic by-products
derived from amino acids.
The pinnate leaf, silvery-brown
pod and bright red seeds of
mescal bean (Sophora
secundiflora), an attractive
leguminous shrub native to the
southwestern United States and
Mexico.
 The poisonous seeds contain the
alkaloid cytisine, and were once
used in the intoxicating, vision-
seeking "red bean dance" prior to
the widespread use of the "less-
life-threatening" peyote cactus.
Adried, Pacific coastal psilocybin
mushroom Psilocybe cyanescens with
an umbrella-like cap and stalk (left),
two peyote (Lophophora williamsii)
buttons (center) and a complete
peyote plant (right). The complete
plant has a thick, tapering, carrot-like
root. Indians cut off the above-
ground crowns and sun-dry them into
brown, "mescal buttons."
 The hair tufts on the crowns become
much more conspicuous in the dried
buttons. It is easy to see how the
Spanish authorities could have
mistaken the dried crowns or tops
(buttons) of peyote cactus for the
caps of teonanacatl mushrooms.
 The Aztecs may have fooled their
conquerers into thinking that these
religious plants were mushrooms,
while the identity of one of their
most spiritual and sacred plants
was actually a cactus.
 The peyote cactus contains more
than 50 different alkaloids, but the
most active hallucinogen is
mescaline. The chemistry, botany and
history of peyote is discussed in a
fascinating book by E.F. Anderson
(Peyote: The Divine Cactus, 1976).
Mescaline has a chemical structure
similar to the brain neurotransmitter
dopamine. It is also structurally similar
to the neurohormone norepinephrine
(noradrenalin) and to the stimulant
amphetamine. In the peyote cactus,
mescaline is formed in a complex
pathway from the amino acid tyrosine.
A similar pathway in humans
produces epinephrine (adrenalin)
and its demethylated precursor
norepinephrine from tyrosine.
Dopamine and its precursor L-dopa
are also derived from a tyrosine
pathway. The following illustration
shows the remarkable molecular
similarity between mescaline and
dopamine:
Indole Alkaloids
 Indole alkaloids contain the indole
carbon-nitrogen ring which is also
found in the fungal alkaloids ergine
and psilocybin, the neurotransmitter
serotonin, and the mind-altering drug
LSD. These alkaloids may interfere or
compete with the action of serotonin
in the brain.
The night-blooming San Pedro
cactus (Trichocereus pachanoi). In
the Andes of Peru, Ecuador and
Bolivia the natives call this tall,
columnar cactus "aguacolla" or
"giganton." An intoxicating drink
called "cimora" is made from the
boiled stems. The floral bracts at
base of Trichocereus blossoms
contain numerous long hairs. Like
peyote, members of this genus
contain mescaline.
Some dangerously poisonous
species of mushrooms are
the red agaric mushroom
(A. muscaria), death cap (A.
phalloides), death angel (A.
ocreata), and panther
amanita (A. pantherina).
 According to Terrence McKenna (Food
of the Gods, 1992), the active alkaloid
in fly agaric mushrooms
(muscimol) The use of mind-altering
psilocybin "magic mushroom,“ is
much stronger such as Stropharia
cubensis, by ancient humans in Africa
may have been a catalyst in the
development of language and religion
in primitive cultures.
 David Isaak (personal
communication, 2002) stated in a
recent e-mail message that in the
Pacific Northwest, a number of
people gather "the panther" for
culinary purposes; cooking it in
several changes of water to
remove "most" of the psychoactive
materials.
 According to R.F. Raffauf (Plant
Alkaloids: A Guide To Their
Discovery and Distribution, 1996),
more than 10,000 different alkaloids
have been discovered in species
from over 300 plant families. For
thousands of plant species, a vast
arsenal of bitter alkaloids
undoubtedly provides a competitive
advantage by repelling hungry
herbivorous mammals.
 Because of the structural diversity
of alkaloids, there is no single
method of their extraction from
natural raw materials.[159] Most
methods exploit the property of
most alkaloids to be soluble in
organic solvents but not in water,
and the opposite tendency of their
salts.
 Most plants contain several
alkaloids. Their mixture is extracted
first and then individual alkaloids
are separated.[ Plants are
thoroughly ground before
extraction. Most alkaloids are
present in the raw plants in the
form of salts of organic acids. The
extracted alkaloids may remain salts
or change into bases.
 Base extraction is achieved by
processing the raw material with
alkaline solutions and extracting
the alkaloid bases with organic
solvents, such as 1,2-
dichloroethane, chloroform,
diethyl ether or benzene.
 Then, the impurities are dissolved
by weak acids; this converts
alkaloid bases into salts that are
washed away with water. If
necessary, an aqueous solution of
alkaloid salts is again made
alkaline and treated with an
organic solvent. The process is
repeated until the desired purity is
achieved.
 Inthe acidic extraction, the raw plant
material is processed by a weak
acidic solution (e.g.,acetic acid in
water, ethanol, or methanol). A base
is then added to convert alkaloids to
basic forms that are extracted with
organic solvent (if the extraction was
performed with alcohol, it is removed
first, and the remainder is dissolved
in water). The solution is purified as
described above.
 Alkaloids are separated from
their mixture using their
different solubility in certain
solvents and different
reactivity with certain reagents
or by distillation.
 1. Maceration - This process is
where plant tissues and cells are
broken or disrupted to release the
chemicals.
 A. the homogenized plant sample is
soaked in a solvent in a closed
container and left at room
temperature.
The solvent is then decanted and
filtered to remove debris. To
further purify the extract, it is dried
using the rotary evaporator.
 B.The plant may also be dried
at room temperature or under
the heat of the sun and then
ground in a mortar and pestle.
The grinding serves to
increase the surface area for
greater extraction of
chemicals from the tissues.
General Maceration Procedure:
1. Dry plant material under the
heat of the sun or air dry.
2. Place in close vessel with
chosen solvent.
3. Allow to settle for 2-7 days
shaking from time to time.
4. Filter out solid residue and
press residue. Combine liquids.
5. Remove solvent using rotary
evaporator.
6. Add water to weighed extract
and record before using.
 2.Steam distillation – the plant
sample can be wet or dry. The
sample is placed in a flask and
immersed in water. The flask is
then connected to a condenser and
heated. The distillate is collected in
a tube that is connected to a
condenser
 It comes out as a mixture of oils
and water and they are collected
separately. Steam distillation is
good for the extraction of volatile
phytochemicals.
 3.Soxhlet Extraction - This a
general method of extracting
fats/ oils. The homogenized
plant sample is placed in a
cellulose thimble in an
extraction chamber. The
chamber is placed on top of an
collection flask which is placed
beneath a condenser. (see
picture) .
A solvent of choice is added to
the sample which gets heated
up under reflux. The
condensed solvent with
extracts gets collected in the
flask connected below
extraction chamber.
 1. sublimation
 2. Percolation
 3. ultra sound - assisted extraction
Aweed is a plant whose
use has not yet been
discovered …..