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I
lie
method
has
also
beenfound
suitable
for
the
extraction
of
more
polar
compounds
such
as
flavanones
and
xanthonesfrom
Maclura
in>iiii/cra,
flavonoids
from
Scutellaria
baicalensis
roots
and
apigenin
\\ow\Matricaria
chamomilla
[35-37].
1.2.2.
Isolation
and
purification
of
natural
products
by
using
chromatography
(
'hromatography
is
a
physical
method
ofseparation
in
which
the
components
to
beseparated
are
distributed
between
twophases
one
of
which
is
stationary(stationary
phase)
while
the
other
(themobile
phase)
moves
through
it
in
a
definite
direction.
The
chromatographic
process
occurs
due
to
differences
in
the
distribution
constant
of
the
individual
sample
components
[38].
Chromatographic
methods:
l.Thin
layer
chromatography
’
Column
chromatography
3.
Gas
liquid
chromatography
(GLC)
I
High
performance
liquid
chromatography
(HPLC).
5.
Gel
filtration
chro-matography
6.
Affinity
chromatography
7.
Paper
chromato
graphy.
Classification
of
chromatography
according
to
mobile
phase
(the
slalionary
phase
may
be
a
solid
or
a
liquid.
And
the
mobile
phase
11
lay
be
liquid
or
gas):
1
.
Liquid
chromatography
(LC):
mobile
phase
is
a
liquid.
(LLC,
LSC).
2.
Gas
chromatography(GC):
mobile
phase
is
a
gas.
(GSC,
GLC).
Liquid
chromatography
Liquid
chromatography
(LC)
is
a
separation
technique
in
which
I
lie
mobile
phase
is
a
liquid.
It
can
be
carried
out
either
in
a
column
or
a
plane.
Present
day
liquid
chromatography
that
generally
utilizes
very
small
packing
particles
and
a
relatively
high
pressure
is
referred
Io
as
high
performance
liquid
chromatographyhigh
performance
liquid
chromatography
(HPLC)
[39].
In
HPLC
the
sample
is
forced
by
a
liquid
at
high
pressure
(the
mobile
phase)
through
a
column
that
is
packed
with
a
stationary
phase
composed
of
irregularly
or
spherically
shaped
particles,
a
porous
monolithic
layer,
or
a
porous
membrane.
HPLC
is
historically
divided
into
two
different
sub-classes
based
on
the
polarity
of
the
https://t.me/med1917
mobile
and
stationary
phases.
Methods
in
which
the
stationary
phase
is
more
polar
than
the
mobile
phase
(e.g.,
toluene
as
the
mobile
phase,
silica
as
the
stationary
phase)
are
termed
normal
phase
liquid
chromatography
(NPLC)
and
the
opposite
(e.g.,
water-methanol
mixture
as
the
mobile
phase
and
Cl
8
=
octadecylsilyl
as
the
stationary
phase)
is
termed
reversed
phase
liquid
chromatography
(RPLC)
[40].
Gas
chromatography
Gas
chromatography
(GC),
also
sometimes
known
as
gas-liquid
chromatography,
(GLC),
is
a
separation
technique
in
which
the
mobile
phase
is
a
g
as.
Gas
chromatographic
separation
is
always
carried
out
in
a
column,
which
is
typically
«packed»
or
«capillary».
Packed
columns
are
the
routine
work
horses
of
gas
chromatography,
being
cheaper
and
easier
to
use
and
often
giving
adequate
per
formance.
Capillary
columns
generally
give
far
superior
resolution
and
although
more
expensive
are
becoming
widely
used,
especially
for
complex
mixtures.
Both
types
of
column
are
made
from
non
adsorbent
and
chemically
inert
materials.
Stainless
steel
and
glass
are
the
usual
materials
for
packed
columns
and
quartz
or
fused
silica
for
capillary
columns
[41].
Gas
chromatography
is
based
on
partition
equilibrium
of
analyte
between
a
solid
or
viscous
liquid
stationary
phase
(often
a
liquid
silicone-based
material)
and
a
mobile
gas
(most
often
helium).
The
stationary
phase
is
adhered
to
the
inside
of
a
s
mall-diameter
(commonly
0.53
-
0.18mm
inside
diameter)
glass
or
fused-silica
tube
(a
capillary
column)
or
a
solid
matrix
inside
a
larger
metal
tube
(a
packed
column).
It
is
widely
used
in
analytical
chemistry;
though
the
high
temperatures
used
in
GC
make
it
unsuitable
for
high
molecular
weight
biopolymers
or
proteins
(heat
denatures
them),
frequently
encountered
in
biochemistry,
it
is
well
suited
for
use
in
the
petrochemical,
environmental
monitoring
and
remediation,
and
industrial
chemical
fields.
It
is
also
used
extensively
in
chemistry
research.
Classification
according
to
the
packing
of
the
stationary
phase:
1.
Thin
layer
chromatography
(TLC):
the
stationary
phase
is
a
thin
layer
supported
on
glass,
plastic
or
aluminum
plates.
2.
Paper
chromatography
(PC):
the
stationary
phase
is
a
thin
film
of
liquid
https://t.me/med1917
supported
on
an
inert
support.
3.
Column
chromatography
(CC):
■.liltionary
phase
is
packed
in
a
glass
column.
Classification
according
to
the
force
of
separation:
1.
Adsorption
cliromatography.
2.
Partition
chromatography.
3.
Ion
exchange
chro
matography.
4.
S
ize
exclusion
chromatography.
5.
Affinity
chro
matography.
Paper
chromatography
Paper
chromatography
is
a
technique
that
involves
placing
a
.mall
dot
or
line
of
sample
solution
onto
a
strip
of
chromatography
paper.
The
paper
is
placed
in
a
container
with
a
shallow
layer
of
solvent
and
sealed.
As
the
solvent
rises
through
the
paper,
it
meets
the
sample
mixture,
which
starts
to
travel
up
the
paper
with
the
solvent.
This
paper
is
made
of
cellulose,
a
polar
substance,
and
the
compounds
within
the
mixture
travel
farther
if
they
are
non-polar.
More
polar
substances
bond
with
the
cellulose
paper
more
quickly,
and
therefore
do
not
travel
as
far.
Thin
layer
chromatography
Thin
layer
chromatography
(TLC)
is
aw
idely
employed
laboratory
technique
and
is
similar
to
paper
chromatography.
Thin
layer
chromatography
(TLC)
is
a
method
for
identifying
substances
and
testing
the
purity
of
compounds.
TLC
is
a
useful
technique
because
it
is
relatively
quick
and
requires
small
quantities
of
material.
However,
instead
of
using
a
stationary
phase
of
paper,
it
involves
a
stationary
phase
of
a
thin
layer
of
adsorbent
like
silica
gel,
alumina,
or
cellulose
on
a
flat,
inert
substrate.
Compared
to
paper,
it
lias
the
advantage
of
faster
runs,
better
separations,
and
the
choice
between
different
adsorbents.
For
even
better
resolution
and
to
allow
lor
quantification,
high-performance
TLC
can
be
used.
An
older
popular
use
had
been
to
differentiate
chromosomes
by
observing
distance
in
gel
(separation
of
was
a
separate
step).
Retention
Factor,
R
f
The
retention
factor,
R
f
,
is
a
quantitative
indication
of
how
far
a
particular
compound
travels
in
a
particular
solvent.
The
Revalue
is
a
good
indicator
of
whether
an
unknown
compound
and
a
known
compound
are
similar,
if
not
identical.
If
the
R
f
value
for
the
https://t.me/med1917
unknown
compound
is
close
or
the
same
as
the
Rf
value
for
the
known
compound
then
the
two
compounds
are
most
likely
similar
or
identical
(Picture
1.1).
The
retention
factor,
R
f
,
is
defined
as
Rf=
distance
the
solute
(DI)
moves
divided
by
the
distance
traveled
by
the
solvent
front
(D2)
R
f
=
Dl/D2
where
D
1
=
distance
that
color
traveled,
measured
from
center
of
the
band
of
color
to
the
point
where
the
food
color
was
applied
D2
=
total
distance
that
solvent
traveled
Start
Eid
So-vent
tar
Solvent
«
*
t
«
«
«
Solvent
After
Ten
Minutes
Picture
1.2.
Thin
layer
chromatography
and
R
f
calculations
Column
chromatography
Column
chromatography
is
a
separation
technique
in
which
the
stationary
bed
is
within
a
tube.
The
particles
of
the
solid
stationary
phase
or
the
support
coated
with
a
liquid
stationary
phase
may
fill
the
whole
inside
volume
of
the
tube
(packed
column)
or
be
concentrated
on
or
along
the
inside
tube
wall
leaving
an
open,
unrestricted
path
for
the
mobile
phase
in
the
middle
part
of
the
tube
(open
tubular
column).
Differences
in
rates
of
movement
through
the
medium
are
calculated
to
different
retention
times
of
the
sample.
In
1978,
W.
Clark
Still
introduced
a
modified
version
of
column
chromatography
called
flash
column
chromatography.
The
technique
is
very
similar
to
the
traditional
column
chromatography,
except
for
that
the
solvent
is
driven
through
the
column
by
applying
positive
pressure.
This
allowed
most
separations
to
be
performed
in
https://t.me/med1917
less
I
han
20
minutes,
with
improved
separations
compared
to
the
old
method.
Modern
flash
chromatography
systems
are
sold
as
pre-
pneked
plastic
cartridges,
and
the
solvent
is
pumped
through
the
curl
ridge.
Systems
may
also
be
linked
with
detectors
and
fraction
collectors
providing
automation.
The
introduction
of
gradient
pumps
i
c
s
111
ted
in
quicker
separations
and
less
solvent
usage.
Problems
I
.
Explain:
Historically
important
natural
products,
Distribution
of
plant
resources
in
Kazakhstan.
2
Please
explain:
Kazakh
traditional
medicine.
Development
condition
of
phar
macology
in
Kazakhstan?
1.
Please
give
definition
for:
Natural
products
chemistry,
Natural
products,
and
Phytochemistry.
4.
Illustration:
Major
classes
of
natural
products,
Definition:
Medicinal
che
mistry,Pharmacognosy.
5.
Please
making
definition
and
explain:
Metabolites,
Primary
metabolites
and
Secondary
metabolites.
6.
Please
explain:
Development
of
isolation
and
purification
of
natural
products.
7.
Chromatography
-what
does
it
mean?
History
of
chromatography?
8.
Principles
and
types
of
chromatography.
Explain
with
applications.
9.
Liquid
chromatography,
types,
which
kind
of
natural
compounds
and
material
could
be
analyzed
by
the
method.
1
0.
Malang
statements
on:
Adsorption
chromatography,Partition
chromatography,
types,
and
applications.
1
1.
Please
explain:
Paper
chromatography,
Thin
layer
chromatography,
Column
chromatography.
12.
What
is
Revalue?
What
does
it
mean
that
difference
of
R
f
value?
Explain
the
affecting
factors
to
R
f
value.
https://t.me/med1917
2.
PHENOLS
AND
FLAVONES
2.1.
Classification,
structures,
and
propertiesof
phenolic
compounds
In
organic
chemistry,
phenols,
sometimes
called
phenolics,
are
a
class
of
chemical
compounds
consisting
of
a
hydroxylgroup
(-OH)
bonded
directly
to
an
aromatic
hydrocarbon
group.
The
simplest
of
the
class
is
phenol,
which
is
also
called
carbolic
acid
C
6
H
5
OH.
Phenolic
compounds
are
classified
as
simple
phenols
or
polyphenols
based
on
the
number
of
phenol
units
in
the
molecule.
Quercetin,
a
typical
flavonoid,
is
a
polyphenol
OH
OH
or
Phenol
-
the
simplest
of
the
phenols
Phenolic
compounds
are
synthesized
industrially;
they
also
are
produced
by
plants
and
microorganisms,
with
variation
between
and
within
species.Although
similar
to
alcohols,
phenols
have
unique
properties
and
are
not
classified
as
alcohols
(since
the
hydroxyl
group
is
not
bonded
to
a
saturated
carbon
atom).
They
have
higher
acidities
due
to
the
aromatic
ring's
tight
coupling
with
the
oxygen
and
a
relatively
loose
bond
between
the
oxygen
and
hydrogen.
The
acidity
of
the
hydroxyl
group
in
phenols
is
commonly
intermediate
https://t.me/med1917
between
that
of
aliphatic
alcohols
and
carboxylic
acids
(their
pK
a
is
usually
between
10
and
12).
Organisms
that
synthesize
phenolic
compounds
do
s
о
in
response
to
ecological
pressures
such
as
pathogen
and
insect
attack,
UV
radiation
and
wounding.
As
they
are
pi
esent
in
food
consumed
in
human
diets
and
in
plants
used
in
traditional
medicine
of
several
cultures,
their
role
in
human
health
and
disease
is
a
subject
of
research.Some
phenols
are
germicidal
and
.no
used
in
formulating
disinfectants.
Others
possess
estrogenic
or
endocrine
disrupting
activity
[42-43].
Classification
There
are
various
classification
schemes.
A
commonly
used
scheme
is
based
on
the
number
of
carbons
and
was
devised
by
IeUrey
Harborne
and
Simmonds
in
1964
and
published
in
1980
(Table
2.1):
They
can
also
be
classified
on
the
basis
of
their
number
of
phenol
p,
roups.
They
can
therefore
be
called
simple
phenols
or
monophenols,
with
only
one
phenolic
group,
or
di-
(bi-),
tri-
and
oligophenols,
with
two,
three
or
several
phenolic
groups
respectively
[44].
Classification
of
phenolic
compounds
Table
2.1
Number
of
carbon
atoms
Basic
skelet
on
Number
of
phenolic
cycles
Class
Examples
1
2
3
4
5
a
c
6
1
Simple
phenols,
Benzoquinones
Catechol,
Hydroquinone,
2,6-
Dimethoxybenzoqui
none
7
Сб
-Cj
1
Phenolic
acids,
Phenolic
aldehydes
Gallic,
salicylic
acids
К
c
6
-c
2
1
Acetophenones,
Tyrosine
derivatives,
Phenylacetic
acids
3-Acetyl-6-
methoxybenzaldehy
de,
Tyrosol,
p-
Hydroxyphenylaceti
c
acid,
Homogentisic
acid
https://t.me/med1917
Not
in
this
Harborne
classification
are
the
С
й
-С
7
-С
й
diarylheptanoids
.
1
2
3
4
5
9
c
6
-c
3
1
Hydroxycinnamic
acids,
Phenylpropenes,
Coumarins,
Isocoumarins,
Chromones
Caffeic,
ferulic
acids,
Myristicin,
Eugenol,
Umbelliferone,
aesculetin,
Bergenon,
Eugenin
10
C
6
-C
4
1
Naphthoquinones
Juglone,
Plumbagin
13
C
6
-Cr
C
6
2
Xanthonoids
Mangiferin
14
C
6
-C
2
-
c
6
2
‘
Stilbenoids,
Anthraquinones
Resveratrol,
Emodin
15
C
6
-C
3
-
C
6
2
Chaiconoids,
Flavonoids,
Isoflavonoids,
Neoflavonoids
Quercetin,
cyanidin,
Genistein
16
C
6
-C
4
-
C
6
2
Halogenated
algal
phenolic
compounds
Kaviol
A,
colpol
18
(C
6
-
c
3
)2
2
Lignans,
Neolignans
Pinoresinol,
Eusiderin
30
(C
6
-
C
3
-
c
6
)2
4
Biflavonoids
Amentoflavone
Many
(C
6
-
C
3
)„,
(C
6
)
n
,
(C
6
-
C
3
-
Сб)„
n>
12
Lignins,
Catechol
melanins,
Flavolans
(Condensed
tannins),
Polyphenolic
proteins,
Polyphenols
Raspberry
ellagitannin,
Tannic
acid
The
largest
and
best
studied
natural
phenols
are
the
flavonoids,
which
include
several
thousand
compounds,
among
them
the
flavonols,
flavones,
flavan-3ol
(catechins),
flavanones,
anthocyanidins
and
isoflavonoids.
https://t.me/med1917
2.2.
Flavonoids,
classification,
and
biological
activities
Flavonoids
(from
the
Latin
word
flavus
meaning
yellow,
their
i
olor
in
nature)
are
a
class
of
plantsecondary
metabolites.
Flavonoids
an-
a
group
of
natural
compounds
with
variable
phenolic
structures
and
arc
found
in
plants.
In
1930
a
new
substance
was
isolated
from
iaaugcs.
At
that
time
it
was
believed
to
be
a
member
of
a
new
class
id
vitamins
and
was
designated
as
vitamin
P.
Later
on
it
became
i
Icar
that
this
substance
was
a
flavonoid
(rutin).
Flavonoids
consist
ul
a
large
group
of
polyphenolic
compounds
having
a
benzo-y-
pyionc
structure
and
are
ubiquitously
present
in
plants.
They
are
■•vi
ilhcsized
by
phenylpropanoid
pathway.
Available
reports
tend
to
I
low
that
secondary
metabolites
of
phenolic
nature
including
fla
vonoids
are
responsible
for
the
variety
of
pharmacological
acti
vities.
Chemically,
they
have
the
general
structure
of
a
15-carbon
skeleton,
which
consists
of
two
phenyl
rings
(A
and
B)
and
heterocyclic
ring
(C).
This
carbon
structure
can
be
abbreviated
('(>
C3-C6.
According
to
the
IUPAC
nomenclature,
they
can
be
clas-
'.i
I
icd
into:
1
.
Flavonoids
or
Bioflavonoids,
2.
Isoflavonoidsderived
from
3-phenylchromen-4-one
(3-phenyl-
1
,4-benzopyrone)
structure.
3.
Neoflavonoids,
derived
from
4-phenylcoumarine
(4-phenyl-
1
,2-benzopyrone)
structure.
The
three
flavonoid
classes
above
are
all
ketone-containing
compounds,
and
as
such,
are
anthoxanthins
(flavones
and
flavonols).
I
his
class
was
the
first
to
be
termed
bioflavonoids.
The
terms
llavonoid
and
bioflavonoid
have
also
been
more
loosely
used
to
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describe
non-ketone
polyhydroxy
polyphenol
compounds
which
are
more
specifically
termed
flavonoids.
The
three
cycle
or
heterocycles
in
the
flavonoid
backbone
are
generally
called
ring
A,
В
and
C.
Ring
A
usually
shows
a
phloroglucinol
substitution
pattern.
Over
5000
naturally
occurring
flavonoids
have
been
charac
terized
from
various
plants.
They
have
been
classified
according
to
their
chemical
structure,
and
are
usually
subdivided
into
the
following
subgroups
(Table
2.2):
Skeleton
and
examples
of
Flavonoids
Flavones
and
flavonols
Table
2.2
Group
Skeleton
Examples
Description
Structural
formula
Flavone
2-
phenylchromen-
4-one
0
Luteolin,
Apigenin,
Tangeritin
Flavonol
or
3
-hydroxyflavone
3-hydroxy-2-
phenylchromen-
4-one
0
Quercetin,
Kaempferol,
Myricetin,
Fisetin,
Galangin,
Isorhamnetin,
Pachypodol,
Rhamnazin,
Pyranoflavonols,
Furanoflavonols,
Flavanones
Description
Structural
formula
Flavanone
2,3-dihydro-2-
phenylchromen-
4-one
co
11
о
Hesperetin,
Narineenin.
Eriodictyol.
Homoeriodictvol
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