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Amphibine
F,
spinanine
A
Amphibine
B,
lotusinc
C
<
<D
c
‘
S
о
u.
Q
1
Aconitine,
delphinine
Solasodine,
solanidine,
veralkamine,
batrachotoxin
cc
doalkaloids
(terpenes
and
steroids)
Mevalonic
acid
—
»
izopentenilpyrophosfate
—
>
geranyl
pyrophosphate
Cholesterol,
arginine
СЧ
Amphibine
F
type
Amfibine
В
type
Mucroninc
A
type
□
P
h
Lycoctonine
type
-
Peptide
alkaloids
with
a
15-
mcmbcred
cycle
Diterpenes
Steroids
0 0
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I
’
Properties
of
alkaloids
and
Distribution
in
nature
Mir.I
alkaloids
contain
oxygen
in
ilu
n
molecular
structure;
those
Hin|>(iiiiids
are
usually
colorless
i
.lai*,
al
ambient
conditions.
Oxygen-
H>
■
alkaloids,
such
as
nicotine
or
....
r,
arc
typically
volatile,
colorless,
mb
liquids.
Some
alkaloids
are
iluiul,
like
berberine
(yellow)
and
-in
iimarine
(orange).
Most
alkaloids
are
weak
bases,
but
some,
such
as
theobromine
ail
ihcophylline,
are
amphoteric.
Many
alkaloids
dissolve
poorly
in
iii
i
lait
readily
dissolve
in
organic
solvents,
such
as
diethyl
ether,
*
11
1
о
i
о
I'orm
or
1
,2-dichloroethane.
Caffeine,cocaine,
codeine
and
Tih.nl
ineare
water
soluble
(with
a
solubility
of
>lg/L),
whereas
i.ilo
I-.,
including
morphineand
yohimbine
arehighly
water
soluble
io
I
I
p/L).
<
'i
у
sials
of
piperine
extracted
from
black
pepper.
I
licsc
salts
are
usually
soluble
in
water
and
alcohol
and
poorly
I
able
in
most
organic
solvents.
Exceptions
include
scopolamine
livliobromide,
which
is
soluble
in
organic
solvents,
and
the
water-
oliililc
quinine
sulfate.
Most
alkaloids
have
a
bitter
taste
or
are
poisonous
when
uiri
sii-d.
Alkaloid
production
in
plants
appeared
to
have
evolved
in
ooiisc
to
feeding
by
herbivorous
animals;
however,
some
animals
linvc
evolved
the
ability
to
detoxify
alkaloids.
Some
alkaloids
can
luiiiliicc
developmental
defects
in
the
offspring
of
animals
that
i
ini'.
nine
but
cannot
detoxify
the
alkaloids.
Distribution
in
nature
Strychnine
tree.
Its
seeds
are
rich
in
strychnine
and
lx
in
ine.
Alkaloids
are
generated
by
various
living
organisms,
■
ipreially
by
higher
plants-
about
10
to
25%
of
those
contain
ill
uloids.
Therefore,
in
the
past
the
term
«alkaloid»
was
associated
Illi
plants.
I
he
alkaloids
content
in
plants
is
usually
within
a
few
percent
uni
is
inhomogeneous
over
the
plant
tissues.
Depending
on
the
type
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of
plants,
the
maximum
concentration
is
observed
in
the
leaves
(black
henbane),
fruits
or
seeds
(Strychnine
tree),
root
(Rauwolfia
serpentina)
or
bark
(cinchona).
Furthermore,
different
tissues
of
the
same
plants
may
contain
different
alka
loids.
Beside
plants,
alkaloids
are
found
in
certain
types
of
fungi,
such
as
psilocybin
in
the
fungus
of
the
genus
Psilocybe,
and
in
animals,
such
as
bufotenin
in
the
skin
of
some
toads.
Many
marine
organisms
also
contain
alkaloids.
Some
amines,
such
as
adrenaline
and
serotonin,
which
play
an
important
role
in
higher
animals,
are
similar
to
alkaloids
in
their
structure
and
biosynthesis
and
are
sometimes
called
alkaloids
[59].
3.3.
Extraction
and
isolation
method
for
alkaloids
Isolation
of
Alkaloids:
In
order
to
isolate
pure
alkaloid
from
plant
source,
the
procedures
to
be
followed
are
as
follows:
Step
1:
Collection
of
plant
material,
air-drying
the
plant
material
to
remove
water,
pulverization
of
the
air-dried
plant
material
and
solvent
extraction
protocol
of
the
powdered
plant
materials.
Step
2:
Purification
of
the
alkaloid-This
is
done
to
separate
alkaloid
from
the
solution.
This
is
done
by
running
chromatography
on
the
syrupy
form
of
the
extract.
Step
3:
involves
the
crystallization
and
further
puri
fication
of
the
isolates.
Crystals
of
piperine
extracted
from
black
pepper,
because
of
the
structural
diversity
of
alkaloids,
there
is
no
single
method
of
their
extraction
from
natural
raw
materials.Most
methods
exploit
the
property
of
most
alkaloids
to
be
sol
uble
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
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ill
nloids
may
remain
salts
or
change
into
bases.
Base
extraction
is
к
Iiicved
by
processing
the
raw
material
with
alkaline
solutions
and
lincling
the
alkaloid
bases
with
organic
solvents,
such
as
1,
2-dich-
li'HH'iliaiie,
chloroform,
diethyl
ether
or
benzene.
Then,
the
im-
i
и
и
ilics
arc
dissolved
by
weak
acids;
this
converts
alkaloid
bases
into
all
1,
I
ha
t
are
washed
away
with
water.
If
necessary,
an
aqueous
nliiiion
of
alkaloid
salts
is
again
made
alkaline
and
treated
with
an
u
runic
solvent.
The
process
is
repeated
until
the
desired
purity
is
lueved
|65-66].
In
the
acidic
extraction,
the
raw
plant
material
is
processed
by
a
il
acidic
solution
(e.g.,
acetic
acid
in
water,
ethanol,
or
methanol).
\
base
is
then
added
to
convert
alkaloids
to
basic
forms
that
are
1
1
acted
with
organic
solvent
(if
the
extraction
was
performed
with
■di
nliol,
it
is
removed
first,
and
the
remainder
is
dissolved
in
water).
Hr
solution
is
purified
as
described
above.
Alkaloids
are
separated
from
their
mixture
using
their
different
iiliibility
in
certain
solvents
and
different
reactivity
with
certain
11
11'i
‘
iits
or
by
distillation.
PLANT
MATERIAL
Shade
dried.
Pulverised,
Extracted
EXTRACT
♦
0.1MHCI
.....
'if.
lave
г
Extract
H.p.ilv
li-ll
H-9
I
'Jhivlkni
Orgaaic
layer
Extract
i
it
u
tn
nt
wills
Cliloiofoi-
it
i
i
di
tiled
Extract
Separation
by
column
chroma
togtaphy
or
НИХ
Pieparative
TEC
Further
Purification
by
crystallisation
Pure
Isolate
Scheme
3.1.
Isolation
of
alkaloid
from
plant
material
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The
extraction
procedure
often
used
in
the
isolation
of
alkaloid
is
summarized
in
the
scheme
1
below.
3.4.
Dimer
alkaloids
In
addition
to
the
described
above
monomeric
alkaloids,
there
are
also
dimeric,
and
even
trimeric
and
tetrameric
alkaloids
formed
upon
condensation
of
two,
three,
and
four
monomeric
alkaloids.
Dimeric
alkaloids
are
usually
formed
from
monomers
of
the
same
type
through
the
following
mechanisms:
-
Mannich
reaction,
resulting
in,
e.g.,
voacamine
-
Michael
reaction
(villalstonine)
-
Condensation
of
aldehydes
with
amines
(toxiferine)
-
Oxidative
addition
of
phenols
(dauricine,
tubocurarine)
-
Lactonization
(carpaine).
Voacamine
Dauricine
3.5.
Applications
of
alkaloids
In
medicine
Medical
use
of
alkaloid-containing
plants
has
a
long
history,
and,
thus,
when
the
first
alkaloids
were
isolated
in
the
19th
century,
they
immediately
found
application
in
clinical
practice.
Many
synthetic
and
semisynthetic
drugs
are
structural
modifications
of
the
alkaloids,
which
were
designed
to
enhance
or
change
the
primary
effect
of
the
drug
and
reduce
unwanted
side
effects.
For
example,
naloxone,
an
opioid
receptorantagonist,
is
a
derivative
of
thebaine
that
is
present
in
opium
[67-68].
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Many
alkaloids
are
still
used
in
medicine,
usually
in
the
form
of
nli.'i,
including
the
following
(Table3.2
):
Table
3.2
Important
alkaloids
with
biological
actions
Alkaloid
\|llllllillC
tiinpine,
scopolamine,
hyoscyamine
i
.illeine
•
Illll'illC
i
uh
liicinc
I
IllrllllC
I
i
pul
и
I
kaloids
Miiiplunc
i
Hi
nline
l'li\
'.usligmine
>
1
1111III
i
i
ic
llllllllic
I
I
ripinc
I
iilinciii'iii'ine
'
inlihisline,
vincristine
\
iiiriiiiiine
tuliiinbine
Action
antiarrhythmic
anticholinergic
Stimulant,
adenosine
receptor
antagonist
cough
medicine,
analgesic
remedy
for
gout
antiprotozoal
agent
sympathomimetic,
vasodilator,
antihypertensive
analgesic
Stimulant,
Nicotinic
acetylcholine
receptor
agonist
inhibitor
of
acetylcholinesterase
antiarrhythmic
antipyretics,
antimalarial
antihypertensive
Muscle
relaxant
antitumor
vasodilating,
antihypertensive
Stimulant,
Aphrodisiac
lii
agriculture
Prior
to
the
development
of
a
wide
range
of
relatively
low-toxic
\iillictic
pesticides,
some
alkaloids,
such
as
salts
of
nicotine
and
iiinbasine,
were
used
as
insecticides.
Their
use
was
limited
by
their
lupli
(oxicity
to
humans.
Thebaine
Naloxone
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Use
as
psychoactive
drugs
Preparations
of
plants
containing
alkaloids
and
their
extracts,
and
later
pure
alkaloids,
have
long
been
used
as
psychoactive
substances.
Cocaine,
caffeine,
and
cathinone
are
stimulants
of
the
central
nervous
system.
Mescaline
and
many
of
indole
alkaloids
(such
as
psilocybin,
dimethyltryptamine
and
ibogaine)
have
hallucinogenic
effect.
Morphine
and
codeine
are
strong
narcotic
pain
killers.
There
are
alkaloids
that
do
not
have
strong
psychoactive
effect
themselves,
but
are
precursors
for
semi-synthetic
psychoactive
drugs.
For
example,
ephedrine
and
pseudoephedrine
are
used
to
produce
methcathinone
and
methamphetamine.
Thebaine
is
used
in
the
synthesis
of
many
painkillers
such
as
oxycodone.
Problems
1
.
Definition:
What
is
Alkaloid,
show
structures,
and
make
short
statements
on
historical
important
alkaloids.
2.
Please
make
detail
discuss
on:
Classification
of
alkaloids,
show
related
structures
and
make
examples.
3.
What
are
the
chemical
and
biochemical
properties
of
Alkaloids,
and
identifi
cation
methods?
4.
Extraction
and
isolation
of
alkaloids
from
plant
resources,
draw
block
scheme,
please
indicated
the
applying
solvents
and
methods.
5.
Explain
Protoalkaloids,
together
with
Pyrrolidine,
Tropane,
and
Pyrrolizidine
types
alkaloids,
discuss
detail
with
examples.
6.
Explain
Piperidine,
Quinolizidine,
Isoquinoline,
and
Indolizidine
types
alka
loids,
discuss
detail
with
examples.
7.
Explain
Pyridine,
Oxazole,
Isoxazole
and
Indole
alkaloids
types
alkaloids,
discuss
detail
with
examples.
8.
Explain:
Distribution
of
alkaloids
in
plant
materials.
And
applications
of
al
kaloids.
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4.
TERPENS
■l.l.
Introduction
and
classification
I'eipcnoids
(or
isoprenoids),
a
su
bclass
of
the
prenyllipids
ii-1
penes,
prenylqunones,
and
sterols),
represent
the
oldest
group
of
11
in
1
1
molecular
products
synthesized
by
plants
and
are
probably
the
i
in
r.t
widespread
group
of
natural
products.
terpenoids
can
be
described
as
modified
terpenes,
where
methyl
г
i
-
a
ips
are
moved
or
removed,
or
oxygen
atoms
added.
Inversely,
......
authors
use
the
term
«terpenes»
more
broadly,
to
include
the
i
ipenoids.
During
the
19th
century,
chemical
works
on
turpentine
lid
lo
name
«terpene»
the
hydrocarbons
with
the
general
formula
|
inll|
(
,
found
in
that
complex
plant
product.
These
terpenes
are
lni|iiently
found
in
plant
essential
oils
which
contain
the
«Quinta
■
■
.
‘
Ulin»,
the
plant
fragrance
[69].
I
hey
are
universally
present
in
small
amounts
in
living
ui
nanisms,
where
they
play
numerous
vital
roles
in
plant
physiology
a
;
well
as
important
functions
in
all
cellular
membranes.
The
various
linn
lions
of
terpene
natural
products
in
the
natural
world
have
been
n
irwed
[70].
On
the
other
hand,
they
are
also
accumulated
in
many
-
ir.es,
and
it
is
shown
that
the
extraordinary
variety
they
then
display
■
hi
be
due
to
ecological
factors
playing
an
evolutionary
role.
H
CH
3
X
^CH
2
Isoprene
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They
may
be
defined
as
a
group
of
molecules
whose
structure
is
based
on
a
various
but
definite
number
of
isoprene
units
(methylbuta-
1,3
-diene,
named
hemiterpene,
with
5
carbon
atoms).
Terpenoids
are
extraordinarily
diverse
but
they
all
originate
through
the
condensation
of
the
universal
phosphorylated
derivative
of
hemiterpene,
isopentenyl
diphosphate
(IPP)
and
dimethylallyl
diphosphate
(DMAPP)
giving
geranyl
pyrophosphate
(GPP)
Fig.4.1.
Figure
4.1.
Biosynthesis
pathways
of
the
terpenoids
OPP
GPP
In
higher
plants,
IPP
is
derived
from
the
classic
mevalonic
acid
pathway
in
the
cytosol
but
from
the
methylerythritol
phosphate
pathway
in
plastids.
It
is
generally
accepted
that
the
cytosolic
pool
of
IPP
serves
as
a
precursor
of
sesquiterpenes,
triterpenes,
sterols
and
polyterpenes
whereas
the
plastid
pool
of
IPP
provides
the
precursors
of
mono-,
di-
and
tetraterpenes.
Some
exceptions
have
been
described
showing
that
interactions
between
the
two
biosynthetic
pathways
may
exist.
A
rational
classification
of
the
terpenes
has
been
established
based
upon
the
number
of
isoprene
(or
isopentane)
units
incorporated
in
the
basic
molecular
skeleton
(Table
4.1):
Table
4.1
Classification
of
terpens
№
Terpenes
Isoprene
units
Carbon
atoms
1
2
3
4
1
Monoterpenes
2
10
2
Sesquiterpenes
3
15
3
Diterpenes
4
20
4
Sesterterpenes
5
25
5
Triterpenes
6
30
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