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Файл:Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_158_библиотеки_им_акад_М_И_Перельмана
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was
poured
into
a
porcelain
dish
and
evaporated
in
a
water
bath
to
form
syrup.
In
the
cooled
residue
oxalate
of
nicotine
and
other
salts
tobacco
alkaloid
are
precipitated.
Filter
the
precipitate,
squeeze
and
shift
into
a
separating
funnel.
To
divide
the
free
alkali
treats
the
residue
with
30%
solution
of
alkali
and
separate
3-4
times
with
ether.
Ether
is
dried
and
distilled
on
potassium
hydroxide.
Nicotine
is
highly
soluble
in
organic
solvents
and
in
water
and
just
received
nicotine
odorless,
colorless,
and
as
oil.
If
his
store
he
gradually
turns
to
black.
Methods
for
determination
and
separation
of
alkaloids
Alkaloids
in
plants
are
in
the
form
of
salts.
Quantitative
determination
of
alkaloids
consists
of
three
parts:
a)
Extraction
of
alkaloids
from
plants
materials.
b)
Purification
of
alkaloids
from
resins,
pigments,
oils,
pectin.
c)
Determination
of
the
purified
alkaloids.
The
composition
of
some
alkaloids
includes
sulfur.
Many
alkaloids
contain
oxygen
are
solid
crystals,
in
some
cases,
amorphous
and
odorless.
An
alkaloid
berberine
-
yellow,
sanguinary
-
orange.
Some
alkaloids
that
do
not
contain
oxygen-volatile
liquids
and
they
are
distilled
with
water.
Alkali
alkaloids
are
readily
soluble
in
organic
solvents
and
do
not
dissolve
in
water.
Because
alkaline
properties,
they
form
salts
with
acids.
These
properties
used
in
separation
and
purification.
Qualitative
reactions
to
the
main
alkaloids:
Table
5.
1
№
Names
of
reagents
Composition
of
reagents
Results
of
reactions
1
2
3
4
I
Mayer
Solution
of
mercury
dichloride
and
potassium
iodide
White
or
yellowish
precipitate
2
Wagner
-
Bouchard
Potassium
iodide
iodine
solution
Brown
precipitate
3
Dragendorff
Solution
of
bismuth
nitrate
and
potassium
iodide
in
the
presence
of
acetic
acid
Yellow-red
or
brick-red
precipitate
-
Ill
https://t.me/med1917
1
2
3
4
4
Marmet
Cadmium
iodide
solution
of
potassium
iodide
White
or
slightly
yellow
precipitate
is
soluble
in
excess
solution
5
Silicotungstic
acid
solution
White
precipitate
6
Solution
of
phosphomolybdic
acid
Yellow
precipitate,
changes
over
time
in
the
blue
or
green
7
Solution
of
phosphotungstic
acid
White
precipitate
8
Solution
of
picric
acid
Yellow
precipitate
These
qualitative
definitions
show
the
presence
of
alkaloids,
and
to
determine
the
exact
group
of
alkaloids
should
be
carried
out
to
determine
the
refined
and
pure
alkaloids.
For
specific
reactions
of
concentrated
sulfuric
and
nitric
acid,
and
sulfuric
acid
containing
formalin
(Marquis
reagent),
ammonium
molybdate
(Froehde
reagent).
In
recent
years,
the
structures
of
alkaloids
to
be
studiedby
using
the
methods
of
gas
chromatography,
UV,
IR,
and
NMR
spectroscopy.
Most
alkaloids
are
stored
in
A-order.
Questions:
1.
Do
your
results
agree
or
disagree
with
your
expectations?
what
do
you
expect?
if
your
results
do
not
agree,
offer
an
explanation
2.
What
do
у
ou
know
about
alkaloids?
Draw
the
structure
of
the
common
alkaloids
3.
How
alkaloids
are
subdivided?
Laboratory
work
6
Obtaining
caffeine
from
tea
in
laboratory
Caffeine
is
a
main
derivative
of
purine.
Its
amount
in
leaves
of
tea
is
3%,
in
the
seeds
of
coffee
is
6%.
Milled
coffee
farm
treats
the
caffeine
from
dried
tea
leaves
and
branch
pieces,
and
also
from
powders
of
tea.
It
can
be
also
produced
by
artificial.
In
medicine
caffeine
is
used
as
stimulant
of
heart
works.
https://t.me/med1917
о
The
reagents
and
materials'.
Tea
and
tea
powders
..........................
50
g
Magnesium
powder
...............................
25
g
Chloroform
.....................................................
150
ml
Hydrogen
chlorine,
ammonia,
codeine
and
hydrogen
double
powder
Small
dried
and
cut
tea
or
tea
powders
add
magnesium
powder
(225g
of
magnesium
oxide
in
150
ml
water),
250
ml
of
water
and
heat
it
about
10-15min.
Connected
water
solution
is
washed
by
25
ml
of
diluted
sulfur
acid
(by
kongo
indicator
check
medium
acid
media)
and
in
water
bath
it
’
s
concentrated
till
it
remains
one
part
of
three.
Hot
solution
is
separated
by
layer
filter,
divided
by
chloroform
5
times.
To
each
extract
spent
30ml
of
solvent.
At
the
first
chloroform
extract
is
diluted
till
a
few
milliliters
by
alkaline,
then
is
washed
by
water
the
same
amount.
Solvent
is
distilled
in
water
bath.
From
sediments
take
the
erode
caffeine,
it
is
divided
by
crystallization
from
8-10
ml
of
water.
Yield
should
be
about
0.8-1
g.
Distillation
caffeine
from
dried
tea.
To
put
small
amount
of
dried
tea
into
clock
glass
and
cover
another
one.
To
observe
distillation
of
caffeine
through
accurately
heating.
It
is
cleaved
to
upper
side
of
glass
in
thin,
needle
form.
Qualitative
reactions.
To
10
mg
of
caffeine
add
5%
of
hydrogen
double
powder,
a
drop
of
25%
HC1
and
to
dry
in
water
bath.
Sediment
is
divided
into
2
parts.
The
first
part
is
immediately
wetted
by
ammonia,
it
is
colored
to
purple.
The
second
part
is
colored
to
light
blue
by
adding
3
drops
of
water
and
5
mg
of
codeine.
Questions:
1.
What
did
you
observe
during
qualitative
reaction?
How
can
you
explain
it?
2.
What
amount
caffeine
presents
in
tea
and
coffee?
3.
Please
discuss
about
chemical
and
biological
properties
of
caffeine.
https://t.me/med1917
Laboratory
work
7
Isolation
of
Carotene
from
carrots
Previtamin
carotene
A
is
found
in
nature
in
the
form
of
three
isomers.
It
is
necessaiy
for
organisms
to
live.
Carotene
produced
in
the
production
of
vitamin.
The
necessary
reagents
and
materials'.
Carrot,
5kg
NaOH,
lOg
Carbon
tetrachloride,
400
ml
Petroleum
ether,
200ml
Methyl
alcohol,
500ml
Chloroform,
400ml
Infusorial
earth,
30g
Magnesium
oxide,
20g
Taking
of
Coagulation',
completely
washed
carrots
by
ground
meat
grinder.
It
is
separated
into
the
fabric,
and
each
part
can
manually
squeeze
out
the
juice.
Compressed
puree
takes
into
cauldron
and
added
1
L
water
and
stirred
for
40
min.
of
intense
mixing
with
mechanical
mixture.
And
then
get
caught
again
compresses
solution.
Add
the
juice
of
two
part
solution,
the
protein
product
of
thermal
coagulation.lt
is
a
mix
of
juice
jug
with
a
temperature
of
60-70
°C
water
bath
heated
before.Hot
juicy
in
no
hurry
to
settle.
Coagulate
output
of
300-400
g
wet.
Crystal
carotene'.
New
infused
coagulate
is
a
separating
funnel.
10
g
NaOH
and
100
g
stirred
tetrachlorate.
Extraction
4
times,
added
solution
is
washed
with
distilled
water,
30-40
degrees
inert
gas
supply
is
kept
in
a
vacuum.
https://t.me/med1917
In
the
flask
with
a
remainder
like
warm
oil
add
30g
of
dry
infusorial
earth.
The
flask
is
shacked
and
mixed
so
it
is
not
adhere
to
the
mass
for
an
hour.
During
adsorption
to
get
rid
of
grease
hardly
lathering
mixtures
it
is
filtered
and
mixed
with
petroleum
ether
(b.p.
50-60
°C)
Filtration
is
conducted
under
non
strong
pressure
of
inertia
gas.
In
this
purpose
the
flask
is
closed
with
lid
with
a
hole.
The
hole
is
continued
by
ball
bladder
which
is
full
of
Carbon
dioxide
or
nitrogen.
Wash
adsorbent
2
times.
Precipitant
is
replaced
into
the
flask
equipped
with
reflux
condenser.
To
fill
150
ml
of
methyl
alcohol
and
to
heat
2-3
min
then
hot
mixture
is
separated
by
that
filter.
By
two
times
washing
we
can
make
away
with
sterols.
Carotene
is
divided
by
several
portions
of
chloroform
from
adsorbent.
Chloroform
is
distilled
under
the
vacuum
30
°C
until
dry
state.
The
sediment
is
dissolved
by
heating
in
10
ml
of
chloroform.
To
the
solution
add
200
ml
of
methyl
alcohol
rapidly.
To
filter
precipitant
by
glass
filter,
wash
by
hot
methyl
alcohol
and
again
dissolve
in
10
ml
of
chloroform
and
add
200
ml
hot
methyl
alcohol
to
precipitate
it.
Taken
crystal
form
of
carotene
is
dried
in
vacuum
desiccator.
Yield
should
be
about
0,3-0,4
g.
Questions:
1
.
How
do
you
think
the
obtaining
results
are
coincided
with
theoretical
part?
Explain
your
answer.
2.
What
kind
biological
activates
you
know
about
carotene?
3.
Please
write
and
explain
the
structure
of
carotene.
Laboratory
work
8
Isolation
and
qualitative
analysis
saponins
from
plant
materials
There
are
three
types
of
reactionsfor
determining
the
saponins
from
plant
resources:
1.
Reactions
based
on
physical
properties
of
saponins;
2.
Reactions
based
on
chemical
properties
of
saponins;
3.
Reactions
based
on
biological
properties
of
saponins;
https://t.me/med1917
Second
group
of
qualitative
reaction
for
saponin
is
deposition
and
color
reaction.
Saponins
precipitate
with
barium
and
magnesium
hydroxich
salts
of
iron,
lead
acetate.
Also
triterpene
saponins
precipitate
in
average
salts,
steroids
in
lead
acetate.
Alcohol
extract
of
triterpcnc
and
steroid
saponins
precipitate
in
alcohol
extract
of
cholesterols.
For
qualitative
reaction
о
I
saponins
will
take
100
ml
flask
and
add
1
g
of
plant.
Then
pour
1
ml
о
I
water,
connect
with
reflux
condenser
and
heat
in
water
bath.
After
that
filtered
and
taken
solution.
Then
we
use
our
solution
for
qualitative
reactions.
1.
Bubble
formation
reaction.
Take
2
test
tubes,
to
the
first
pour
5
ml
of
O,1N
HC1,
to
the
second
poui
5
ml
of
O,1N
NaOH.
For
each
tube
add
2-3
drops
of
plant
extract
and
mix.
We
can
see
existing
of
triterpene
saponins
in
plant
by
constant
and
big
volume
of
bubble
in
tubes.
If
in
the
structure
of
plant
exists
steroid
saponins
bubble
in
alkali
media
will
be
more.
2.
To
the
tube
add
2
ml
of
water
extract
and
lead
acetate.
Precipitating
occur.
3.
To
1ml
of
saponin
extract
added
alcohol
solution
of
1%
cholesterol.
We
take
white
precipitation.
4.
Lafont
reaction.
To
2
ml
of
water
extract
add
1
ml
of
ulfuric
acid,
1
ml
of
ethanol,
1
drop
of
10%
solution
of
iron
sulfate
and
heat.
While
heating
blue-green
color
appear
.
5.
To
2
ml
of
water
extract
added
10%
solution
of
NaNO
3
and
1
drop
of
concentrated
H
2
SO
4
.
After
that
red-blood
color
is
appearing.
6.
Liebermann
Burchard
reaction.
For
this
reaction
investigating
substance
dissolved
in
acetic
anhydride
and
added
concentrated
sulfuric
acid
(50:1).
After
some
time
that
pink
color
will
be
changed
to
blue.
7.
Hemolysis.
To
1
ml
of
isotonic
solution
add
1
ml
of
2%
erythrocyte.
Blood
give
light
red
color.
https://t.me/med1917
8.
Thin-layer
chromatography.
Aqueous
or
alcohol
extract
testedby
chromatography
on
silica
gel
or
aluminium
oxide.
For
neutral
saponins
is
used
n-butanol
-
sulfuric
acid
-
water,
for
acid
saponins
n-butanol
-
in
various
ratio
water
solution
of
ammonia.
Steroid
saponins
in
a
chromatogram
with
1
%
solution
of
three-
chloric
antimony,
concentrated
sulfuric
acid,
and
acetic
anhydride
give
yellow
gouts.
At
present
the
chromatographic
method
is
more
precise
method
of
determination
of
saponins.
Questions:
1
.
What
did
you
actually
observe
from
experiment?
Report
you
actual
findings.
2.
Do
your
results
agree
with
your
expectations?
yes
or
no
why
or
why
not?
Be
specific.
If
needed,
identify
possible
sources
of
error
3.
Give
the
explanation
of
saponins
and
their
structures.
https://t.me/med1917
6.
THE
EXAMINATION
QUESTIONS
FOR
COURSE
OF
CHEMISTRY
OF
NATURAL
COMPOUNDS
1.
Explain:
Historically
important
natural
products,
Distribution
of'
plant
resources
in
Kazakhstan.
2.
Please
explain:
Kazakh
traditional
medicine.
Development
condition
of
pharmacology
in
Kazakhstan?
3.
Please
give
definition
for:
Natural
products
chemistry,
Natural
products,
and
Phytochemistry.
4.
Illustration:
Major
classes
of
natural
products,
Definition:
Medicinal
chemistry,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.
10.
Making
statements
on:
Adsorption
chromatography,
Partition
chromatography,
types,
and
applications.
11.
Please
explain:
Paper
chromatography,
Thin
layer
chroma
tography,
Column
chromatography.
12.
What
is
R
f
value?
What
does
it
mean
that
difference
of
R
r
value?
Explain
the
affecting
factors
to
R
f
value.
13.
Please
Make
illustration:
Phenols,
structures,
classification
and
their
biological
properties.
https://t.me/med1917
14.
Explain
detail:
Flavonoids,
and
their
classification,
please
show
structures
of
each
class.
15.
Illustration:
Extraction
and
isolation
of
flavonoids
from
plant
resources,
and
draw
the
isolation
block
scheme,
indicate
the
applied
solvents
and
methods.
16.
Please
discuss:
Chemical
and
biochemical
properties
of
flavonoids,
identification
method.
17.
Please
make
statements
on
Glycosides,
their
classifications,
and
structures.
18.
Definition:
Carbohydrate,
Discuss
about
groups
of
carbohydrates,
show
structures
with
Fischer
and
Haworth
projections
explain
detail
with
examples.
19.
Make
a
account
for
flavonoids
glycosides
and
write
reaction
of
Hydrolysis
of
glycosides,
related
structures,
and
properties.
20.
Please
make
explain:
Monosaccharaides,
properties,
ring
straight
chain
isomerism,
show
structures
and
explain
detail
with
examples.
21.
Please
give
definition
for
Amino
acids,
write
the
structure,
and
explain
the
naming
methods
and
properties
with
sample.
22.
Making
illustration
and
compare
the
essential
and
non-
essential
amino
acids,
and
basic
set
of
20
amino
acids.
23.
Definition:
What
is
Alkaloid,
show
structures,
and
make
short
statements
on
historical
important
alkaloids.
24.
Please
make
detail
discuss
on:
Classification
of
alkaloids,
show
related
structures
and
make
examples.
25.
What
are
the
chemical
and
biochemical
properties
of
Alkaloids,
and
identification
methods?
26.
Extraction
and
isolation
of
alkaloids
from
plant
resources,
draw
block
scheme,
please
indicated
the
applying
solvents
and
methods.
27.
Explain
Protoalkaloids,
together
with
Pyrrolidine,
Tropane,
and
Pyrrolizidine
types
alkaloids,
discuss
detail
with
examples.
28.
Explain
Piperidine,
Quinolizidine,
Isoquinoline,
and
Indolizidine
types
alkaloids,
discuss
detail
with
examples.
29.
Explain
Pyridine,
Oxazole,
Isoxazole
and
Indole
alkaloids
types
alkaloids,
discuss
detail
with
examples.
https://t.me/med1917
30.
Definition:
What
is
terpenoid,
show
structures,
and
make
short
statements
on
some
important
terpenoids.
31.
Classifications
of
terpens,
detail
discuss
and
write
related
structures
of
each
type.
32.
Extraction
and
isolation
of
terpens
from
plant
resources,
and
to
draw
block
scheme,
indicate
the
applied
solvents
and
methods.
33.
Definition:
Diterpenoids,
explain
with
biosynthesis,
structure
and
properties.
34.
Definition:
Triterpenoids,
explain
with
biosynthesis,
struc
ture
and
properties.
35.
Definition:
Fatty
acids?
What
are
the
key
chemical
properties
of
fatty
acids?
36.
Please
make
a
st
atement
on
marine
natural
products,
introduction,
structure,
properties.
37.
Make
an
account
of
classification
of
glycosides,
show
with
structures,
and
tell
about
physico-chemical
properties
of
glycosides.
38.
Introduction
of
anthocyanines
and
flavones,
structures.
Distributions
in
plant
materials.
Biological
activates.
39.
What
is
essential
oil,
distribution
in
plant
material,
main
compounds,
biological
and
medicinal
activities?
40.
Please
describe
the
methods
of
obtaining
essential
oil
from
plant
resources.
Make
short
statements
for
each
method.
41.
Biosynthesis
pathway
of
steroids,
discuss
about
structure
and
properties.
42.
What
is
Saponin,
distribution
in
plant
materials,
structures
and
biological
properties?
43.
Distribution
of
ursolic
acid
and
oleanolic
acid
in
plant
material,
they
belong
to
which
class
of
natural
products,
structure,
and
biological
activities.
44.
Compare
the
structures
of
Cumarins,
Chaicones
and
Aurones.
There
are
any
relations
or
not?
Discuss
about
their
properties.
45.
Structures
of
abietic
type
of
terpen,
distribution
in
plant
material,
and
biological
activities.
46.
Describe
the
classification
of
sesquiterpens,
write
structures
of
some
important
sesquiterpens
and
biological
activities.
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