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AL-FARABI
KAZAKH
NATIONAL
UNIVERSITY
J.
Jenis
CHEMISTRY
OF
NATURAL
COMPOUNDS
Educational
manual
Almaty
«Qazaq
universitety»
2016
UDC
54
(075.8)
LBC
24
я
73
J
41
Recommendedfor
publication
by
the
Academic
Council
of
the
Faculty
of
Chemistry
and
Chemical
Technology
,
Editorial-Publishing
Council,
and
Educational
and
methodical
association
of
the
Republic
educational-
methodical
council
of
higher
and
postgraduate
education
of
Ministry
of
education
and
science
of
the
Republic
of
Kazakhstan
on
the
basis
of
Al-Farabi
of
Kazakh
National
University
(Protocol
№1
from
07.10.2015)
Reviewer
Doctor
of
chemistry,
Professor
B.
Zh.
Dzhiembaev
Doctor
of
chemistry,
Professor
K.
Yu
Valentina
Doctor
of
chemistry,
Professor
Zh.
A.
Abilov
Doctor
of
chemistry,
Professor
D.
U.
Korulkin
Jenis
J.
J
41
Chemistry
of
natural
compounds:
educational
manual
/
J.
Jenis
-
Almaty:
Qazaq
universitety,
2016.-
134
p.
ISBN
978-601-04-1691-8
The
educational
manual
performed
a
series
of
theory
on
chemistry
of
natural
compounds
which
in-cluding
explanation
some
important
terms,
classification,
structure,
biological
properties,
and
the
extraction,
separation
and
identification
of
biologically
active
substances,
together
with
practical
comprehensive
experiments
and
analytical
studies
such
as
qualitative
and
quantitative
analyzing
biological
active
compounds
by
chromatographic
methods,
and
obtaining
natural
products
from
plant
material
in
laboratory.
The
educational
manual
on
the
discipline
«Chemistry
of
natural
compounds»
is
qualified
standards
in
higher
education
and
recommended
for
3rd
course
students
of
faculty
of
che-mistry
and
chemical
technology.
ISBN
978-601-04-
АТУ
гылыми
исГгапханасы
окулык
Т8
^
2б3
ЗДл1к......
-------
UDC
54
(075.8)
LBC
24
я
73
©
Jenis
J.,
2016
©
Al-Farabi
KazNU,
2016
CONTENTS
List
of
abbreviations
..........................................................................................
5
Introduction
........................................................................................................
7
1.
Historically
important
natural
products
..................................................
9
1.1.
Natural
products
chemistry,
natural
products,
classes,
and
primary
or
secondary
metabolism
...................................................
11
1
.2
Isolation
and
purification
and
structure
elucidation
of
natural
products
...................................................................................
14
1.2.1.
Extraction
of
plant
material
............................................................
15
1.2.2.
Isolation
and
purification
of
natural
products
by
using
chromatography
.............................................................................
21
2.
Phenols
and
flavones
.................................................................................
26
2.1.
Classification,
structures,
and
properties
phenolic
compounds
.............
26
2.2.
Flavanoids,
classification,
and
biological
activities
..............................
29
2.3.
Galloylbergenin
from
Kazakh
traditional
medicinal
plant
of
Bergenia
crassifolia
with
anti-
lipid
droplet
accumulation
activity
................................................................................
34
3.
Alkaloids
.....................................................................................................
40
3.1.
Introduction,
occurrence
,
nomenclature
and
classification
.................
40
3.2.
Properties
of
alkaloids
and
distribution
in
nature
.................................
53
3.3.
Extraction
and
isolation
method
for
alkaloids
........................................
54
3.4.
Dimer
alkaloids
..........................................................................................
56
3.5.
Applications
of
alkaloids
.........................................................................
56
4.
Terpens
.......................................................................................................
59
4.1.
Introduction
and
classification
.................................................................
59
4.2.
Monoterpens,
essential
oils
and
the
methods
of
extracting
essential
oils
...............................................................................................
64
4.3.
Sesquiterpenes
...........................................................................................
68
4.4.
Diterpens
and
sesterterpens
......................................................................
74
4.5.
Triterpenoid
and
steroids
.........................
80
4.6.
Carotenoids
................................................................................................
88
4.7.
Essential
oils
from
Kazakh
traditional
medicinal
plant
of
Thymus
altaica
.....................................................................................
97
5.
Laboratory
works
for
course
of
chemistry
of
natural
compounds
......
103
6.
The
examination
questions
for
the
course
of
chemistry
of
natural
compounds
...............................................................................
118
References
...........................................................................................................
123
LIST
OF
ABBREVIATIONS
AMD
Al
’
CI-MS
ASE
CCD
CLC
C-RPC
DMSO
EPC
FFSLE
FFPC
GC
GC-MS
GLC
GSC
HPLC
HPTLC
IR
LC
LLC
LSC
LC-MS
MPLC
MPSLE
MS
NMR
NP
N-RPC
OPLC
PC
PEC
PHWE
PLE
PS
Rf
RPC
automated
multiple
development
atmospheric
pressure
chemical
ionization
mass
spectrometry
accelerated
solvent
extraction
charge-coupled
device
column
liquid
chromatography
column
rotation
planar
chromatography
dimethylsulfoxide
electro-planar
chromatography
forced-flow
solid-liquid
extraction
forced-flow
planar
chromatography
gas
chromatography
gas
chromatograph
coupled
to
mass
spectrometer
gas-liquid
chromatography
gas-solid
chromatography
high
performance
liquid
chromatography
high
performance
thin-layer
chromatography
infrared
liquid
chromatography
liquid-liquid
chromatography
liquid-solid
chromatography
liquid
chromatography-mass
spectrometry
medium
pressure
liquid
chromatography
medium
pressure
solid-liquid
extraction
mass
spectrometry
nuclear
magnetic
resonance
spectroscopy
normal
phase
normal
chamber
rotation
planar
chromatography
over-pressured
layer
chromatography
paper
chromatography
planar
electrochromatography
pressurized
hot
water
extraction
pressurized
liquid
extraction
selectivity
point
retention
factor
rotation
planar
chromatography
https://t.me/med1917
RPE
rotation
planar
extraction
RP
reversed-phase
RPLC
reversed
phase
liquid
chromatography
SFE
supercritical
fluid
extraction
SLE
solid-liquid
extraction
S-RPC
sequential
rotation
planar
chromatography
ST
solvent
strength
SWE
subcritical/superheated
water
extraction
TLC
thin-layer
chromatography
TLE
thin-layer
electrochromatography
U-RPC
ultra-microchamber
rotation
planar
chromatography
UV
ultraviolet
UV/VIS
ultraviolet/visible
https://t.me/med1917
INTRODUCTION
The
traditionally
natural
products
have
played
an
important
role
in
developing
of
natural
product
chemistry
which
continues
to
expand
to
exciting
new
frontiers
of
great
importance
in
medicine.
Natural
Products
Chemistry
is
a
course
in
the
chemistry
discipline
area.
We
will
explore
the
historical
and
contemporary
role
of
secondary
natural
products
in
health
care
and
commerce.
We
will
learn
how
natural
products
are
normally
classified
according
to
their
biosynthetic
origins
and
chemical
properties.
A
special
emphasis
will
be
placed
on
how
chemical
structure
affects
the
physiological
function
of
various
natural
products.
These
"structure
activity
relationships"
help
us
learn
about
the
interaction
of
small
molecules
in
living
systems
and
pharmacology
of
drugs.
At
present
the
own
production
of
medical
drugs
in
the
Republic
of
Kazakhstan
is
11%
(including
vaccines
-
1.1%),
veterinary
drugs
78%
(mainly
the
manufacture
of
drugs
from
imported
substances),
while
other
drugs
are
being
imported
into
the
country.
The
main
problem
is
the
lack
of
original
domestic
biotechnological
drugs
in
the
presence
of
perspective
experimental
developments.
To
date,
virtually
the
production
of
genetically
engineered
drugs
is
not
adjusted,
while
there
are
original
domestic
or
joint
developments
that
passed
or
passing
phase
of
preclinical
and
clinical
studies.
In
Kazakh
traditional
medicine,the
plant
resources
have
been
efficiently
used
in
the
treatments
of
different
kinds
of
diseases
such
as
bronchitis,
bronchial
asthma,
brohepatitis,
urethritis,
chronic
rheu
matoid
arthritis,
nephritis,
urolithiasis,
pharyngitis,
periodontitis,
stomach
pain,
hyperacidity,
diarrhea,
hemostasia,
metrorrhagia,
snakebite,
cancer
and
so
on.
In
Kazakhstan
grow
over
six
thousand
https://t.me/med1917
kinds
of
plants
in
which
more
than
6000
species
of
highest
vascular
plants,
about
5000
species
of
mushrooms,
4851
species
of
lichen,
more
than
2000
species
of
seaweed
are
registered.
The
study
revealed
that
investigated
plants
belonging
to
famdyChenopodiaceae
is
good
sources
for
biologically
active
substances
which
include:
saponins,
triterpenes,
organic
acids,
amino
acids
flavonoids,
chromones
and
carbohydrates.
The
choice
of
plant
species
which
belong
to
family
of
Chenopodiaceaedue
to
the
fact
that
on
the
territory
of
the
Republic
of
Kazakhstan
salt
tolerant
plants
have
a
huge
reserves
and
in
depth
studies
not
performed
before
which
promotes
the
study
of
their
chemical
composition
and
biological
activity
for
the
purpose
of
development
of
new
drugs
needed
for
the
domestic
pharmaceutical
industry
which
is
one
of
the
main
priorities
of
socio-economic
policy
of
the
Government
of
Kazakhstan.
The
plant
kingdom
offers
a
rich
source
of
structural
biodiversity
in
the
form
of
a
variety
of
natural
products.
By
using
the
rich
resources
of
medicinal
plants
from
Kazakhstan
to
find
new
bioactive
natural
products
which
as
new
drug
leads,
new
anticancer
or
anti
tumor
drugs
and
to
solve
in
our
opinion
with
a
success
a
problem
of
creation
and
introduction
in
the
industry
(medicine
and
agriculture)
of
Kazakhstan
of
new
highly
effective
medical
products.
https://t.me/med1917
1.
HISTORICALLY
IMPORTANT
NATURAL
PRODUCTS
For
centuries,
drugs
were
entirely
of
natural
origin
and
composed
of
herbs,
animal
products,
and
inorganic
materials.
Early
remedies
may
have
combined
these
ingredients
with
witchcraft,
mysticism,
astrology,
or
religion,
but
it
is
certain
that
those
treatments
that
were
effective
were
subsequently
recorded
and
documented,
thus
leading
to
the
early
Herbals.
Traditional
medicinal
practices
have
formed
the
basis
of
most
of
the
early
medicines
followed
by
subsequent
clinical,
phar
macological
and
chemical
studies
[1-2].
Probably
the
most
famous
and
well
known
example
to
date
would
be
the
synthesis
of
the
anti
inflammatory
agent,
acetylsalicyclic
acid
(1)
(aspirin)
derived
from
the
natural
product,
salicin
(2)
isolated
from
the
bark
of
the
willow
tree
Salix
alba
L.
Investigation
of
Papaver
somniferum
L.
(opium
poppy)
resulted
in
the
isolation
ofseveral
alkaloids
including
morphine
(3),
a
commercially
important
drug,
first
reported
in
1803
(Figure
1).
It
was
in
the
1870s
that
crude
morphine
derived
from
the
plant
P.
somniferum,
was
boiled
in
acetic
anhydride
to
yield
diacetylmorphine
(heroin)
and
found
to
be
readily
converted
to
codeine
(painkiller).
Historically,
it
is
documented
that
the
Sumerians
and
Ancient
Greeks
used
poppy
extracts
medicinally,
whilst
the
Arabs
described
opium
to
be
addictive.
Digitalis
purpurea
L.
(foxglove)
had
beentraced
back
to
Europe
in
the
10th
century
but
it
was
not
until
the
1700s
that
the
active
constituent
digitoxin
(4),
a
cardiotonic
glycoside
was
found
to
enhance
cardiac
conduction,
thereby
improving
the
strength
of
cardiac
contractibility.
Digitoxin
(4)
and
its
analogues
have
long
been
used
in
the
management
of
congestive
heart
failure
and
have
possible
long
term
detrimental
https://t.me/med1917
effects
and
are
being
replaced
by
other
medicines
in
the
treatment
of
«heart
deficiency».
The
anti-malarial
drug
quinine(5)
approved
by
the
United
States
FDA
in
2004,
isolated
from
the
bark
of
Cinchona
succirubra
Pav.
exKlotsch,
had
been
used
for
centuries
for
the
treatment
of
malaria,
fever,
indigestion,
mouth
and
throat
diseases
and
cancer.
Formal
use
of
the
bark
to
treat
malaria
was
established
in
the
mid-1800s
when
the
British
began
the
worldwide
cultivation
of
the
plant
[30].
Pilocarpine
(6)
found
in
Pilocarpus
jaborandi
(Rutaceae)
is
an
L-histidine-derived
alkaloid,
which
has
been
used
as
a
clinical
drug
in
the
treatment
of
chronic
open-angle
glaucoma
and
acute
angle-closure
glaucoma
for
over
100
years.
In
1994,
an
oral
formulation
of
pilocarpine
was
approved
by
the
FDA
to
treat
dry
mouth
(xerostomia)
which
is
a
side
effect
of
radiation
therapy
for
head
and
neck
cancers
and
also
used
to
stimulate
sweat
glands
to
measure
the
concentrations
of
sodium
and
chloride
(Figure
1.1)
[3].
In
1998,
the
oral
preparation
was
approved
for
the
management
of
Sjogren's
syndrome,
an
autoimmune
disease
that
damages
the
salivary
and
lacrimal
glands.
о
но
У=г
J
о
2
3
4
Figure
1.1.
Acetylsalicyclic
acid
(1),
Salicin
(2),
Morphine
(3),
Digitoxin
(4),
Quinine
(5)and
Pilocarpine
(6).
https://t.me/med1917
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