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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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и
I
i
vation
of
gene
transcription
and
to
stomatai
closure.
It
was
shown
Hint
di
acylglycerol
pyrophosphate
plays
a
role
as
phospholipid
I'cotid
messenger
in
abscisic
signaling.
A
review
of
the
signaling
network
may
be
found
in
a
paper
by
Giraudat
J
and
in
the
«Plant
hormones»
textbook.
Abscisic
acid
is
an
end
product
of
neoxanthin
"i
violaxanthine
peroxidation
and
reduction
giving
an
apocarotenal
i
ipocarotenoid)
with
a
short
side
chain
(5
carbons),
followed
by
a
mini
oxidation
into
an
acid
form
[88-90].
Abscisic
acid
has
also
a
variety
of
roles
in
plant
development,
lx
id
and
seed
dormancy,
germination,
cell
division
and
movement.
It
пн
Inces
also
storage
protein
synthesis
in
seeds
and
may
be
involved
hi
He
lense
against
insect
attack.
Abscisic
acid
is
biosynthesized
via
■
niolcnoids
(zeaxanthin,
neoxanthin,
violaxanthin)
in
roots
and
niiiliirc
leaves.
Its
direct
precursor
is
xanthoxin
which
is
a
natural
inhibitor
of
plant
growth.
Abscisic
acid
is
ubiquitous
in
lower
and
lnp.lier
plants,
it
is
present
also
in
algae.
Only
the
C2-cis,
C4-trans
i
.niiicr
is
biologically
active.
A
mechanism
of
abscisic
signaling
in
■
i
и
11icction
with
cyclic
ADP-ribose
and
calcium
movement
has
been
Hi'inonstrated
to
mediate
temperature
signaling
in
spongess
well
as
и
.ne
regeneration
in
Cnidaria.
Abscisic
acid
is
not
restricted
to
the
plant
kingdom
and
primitive
in
vertebrates
since
it
has
been
shown
to
be
present
in
the
central
in
i
vous
system
of
pigs
and
rats.
Evidence
was
provided
that
it
is
also
involved
in
the
stimulation
of
human
granulocytes
with
cyclic
ADP-
i
those
as
second
messenger.
This
lipid
may
be
considered
as
anew
pm
inllammatory
cytokine
in
humans.
Human
granulocytes
and
11
loot
li
muscle
cells
are
also
functionally
activated
by
abscissic
acid.
I
linl
messenger
can
be
considered
as
a
new
signal
molecule
involved
in
Hie
development
of
atherosclerosis
[91-93].
Abscisic
acid
was
liown
to
be
a
endogenous
stimulator
of
insulin
release
from
human
.....
crcatic
b
cells
with
cyclic
ADP-ribose
as
second
messenger.
This
observation
suggests
that
this
lipid
phytohormone
may
be
involved
in
ilie
physiology
of
insulin
release,
mainly
in
its
dysregulation
under
i
auditions
of
inflammation.
Together
with
jasmonates,
abscisic
acid
tjns
shown
to
control
excitability
and
closure
of
the
insect
trap
of
I
\iniiaea
muscipula
(Venus
flytrap)
[94-95].
<
ndalene
has
the
cadinane
skeleton
and
is
present
in
essen-
linl
oils
and
in
many
plants.
It
is
used
as
ab
iomarker
in
paleobo
https://t.me/med1917
tanic
studies.
In
connection
with
retene
(l-methyl-7-isopropyl
phc
nanthrene),
it
enables
the
estimation
in
sediments
of
the
importance
of
Pinaceae
in
ancient
forests.
Some
important
sesquiterpenes
Cdalene
CHO
OH
oil
CHO
OH
Thujops&ne
V
The
function
of
curcumene
as
insecticide,
repellent,
and
insect
feeding
deterrent
has
been
previously
reported.
A
parent
compound,
bisabolol,
isolated
from
essential
oils
of
a
variety
of
plants,
showed
at
low
concentration
a
differentiating
effect
in
endothelial
cells
but
an
apoptotic
effect
at
higher
concentration.
Gossypol,
a
sesquiterpene
dimer
found
in
cotton
that
is
formed
from
two
cadinane
units.
All
the
cotton
plant
contains
gossypol.
That
terpene
occurs
as
a
mixture
of
two
enantiomers
but
each
has
different
biological
activities.
For
nonruminant
animals
(rodents,
chickens,
https://t.me/med1917
iHiiiuiiis),
(
-)-gossypol
is
significantly
more
toxic
than
the
(+)
i
iiuniiomer.
It
has
anti-cancer
properties
and
inhibits
male
fertility
in
Imiiniiis.
In
contrast,
cotton
plants
containing
high
levels
of
I
i
I'ossypol
are
resistant
to
insect
damage.
These
terpenes
must
be
11i
no
veil
from
the
plant
parts
and
oil
before
use
as
animal
foods.
h
vclic
sesquiterpenes
with
a
driman
unit
are
widespread
in
plants,
Ini
worts,
fungi
and
certain
marine
organisms
(sponges).
Some
h
111
nines
have
been
identified
in
petroleum
and
are
probably
derived
II
<
и
11
и
microbial
source.
1'1
icy
have
generally
potent
antibacterial
and
antifungal
activities,
11
и
I
11
icy
are
toxic
to
several
invertebrates
and
also
in
fish.
In
idililion,
they
deter
feeding
by
i
nsects
on
plants
and
by
fish
on
piillgcs.
(
upsidiol
is
a
sesquiterpenoid
compound
that
accumulates
in
iiibiicco
Nicotiana
tabacum
and
chili
pepper
Capsicum
annuum
in
и
spouse
to
fungal
infection.
It
is
considered
as
a
phytoalexin.
Driman
squeleton
Avarol,
and
its
quinone
derivative
avarone,
are
biologically
u
live
sesquiterpenoids
which
exhibited
antimicrobial
and
antifungal
<n
livities
and
also
active
against
AIDS
virus.
They
were
isolated
from
a
Med
iterranean
(Dysidia
avara)
and
an
Australian
sponge
tlh'sidia
spp).
They
have
also
potent
antileukemic
activity
both
in
nfro
and
in
vivo
in
mice.
The
1
,4-benzoquinone
moietylinked
to
the
sesquiterpene
is
a
i
om
mon
structural
feature
in
a
large
number
of
terpenoid
i
(impounds
which
have
a
large
spectrum
of
biological
activities,
besides
avarol,
several
other
natural
quinones
and
hydroquinones,
Mich
as
illimaquinone,
nakijiquinone
and
bolinaquinone,
are
present
in
sponges
of
the
order
Dictyoceratida.
All
have
cytotoxic
and
https://t.me/med1917
antiproliferative
properties
which
offer
promising
opportunities
for
the
development
of
new
antitumor
agents.
OH
Avarol
(E)-b-Caryophyllene
A
review
of
the
cytotoxic
termene
quinones
from
marine
sponges
has
been
released
by
Gordaliza
M
[96].
Rasmann
E
et
al.
discovered
that
insect-induced
(E)-b-caryophyllene
emission
from
maize
roots
attracts
nematodes
that
prey
on
the
attacking
insect
larvae.
4.4.
Diterpenes
and
Sesterterpens
They
have
20
carbon
atoms
and
are
derived
fromgeranylgeraniol
pyrophosphate.
They
are
of
fungal
or
plant
origin
and
are
found
in
resins,
gummy
exudates,
and
in
the
resinous
high-boiling
fractions
remaining
after
distillation
of
essential
oils.
The
rosin
remaining
after
distilling
pine
turpentine,
for
instance,
is
rich
in
diterpenoids.
In
ancient
times,
conifer
exudates
were
used
for
caulking
boats
and
waterproofing
ropes.
Resin
secretion
is
also
recognized
to
be
part
of
the
resistance
mechanism
conifers
employ
against
bark
beetles
and
their
associated
pathogenic
fungi.
Diterpenoid
groups
that
are
physiologically
active
include:
vitamin
A
activity
(retinol),
phy
tohormones
that
regulate
plant
growth
and
germination,
e.g.
gibberellin,
fungal
hormones
that
stimulate
the
switch
from
asexual
to
sexual
reproduction,
e.g.
tris-poric
acid;
disease
resistance
agents
(phytoalexins),
e.g.
casbene
and
podocarpic
acid,
the
anticancer
drug,
taxol,
from
the
bark
of
the
yew
tree,
the
cancer
promoter,
phorbol,
and
natural
cannabinoids
[97].
https://t.me/med1917
I
lie
diterpenes
have
exceptionally
open
chain,
as
found
in
■
i
any
I
geraniol
or
phytol
which
forms
a
part
of
chlorophyll
and
the
nli
chain
of
vitamin
E
and
K,
and
crocetinwhich
is
a
diacid
ilih
i
penoid
and
the
lipid
part
of
the
crocins,
glycosylated
derivatives
|iii
,
!,en(
in
saffron.
I
xamples
of
diterpene
substances
are
given
below:
all
trans
retinol
laxism
(iibbereliin
A1
2
OH
o
Tnsporic
acid
HO
7.)
Bz
CAc
Taxd
OH
Podocarpic
acid
Abietic
acid
https://t.me/med1917
Abietic
acid
is
an
irritant
compound
present
in
pine
wood
and
resin.
It
is
the
most
abundant
compound
present
in
rosin,
the
solid
fraction
of
the
oleoresin
of
coniferous
trees.
It
is
mainly
used
to
make
lacquers
and
varnishes
and
metal
resinates.
These
resinates
are
produced
in
reacting
abietic
acid
(or
a
similar
compound)
with
a
metal
salt
(gold,
indium,
nickel,
palladium,
platinum,
silver)
and
used
in
a
wide
variety
of
applications
where
high
purity
metals
in
organic
solution
form
is
needed
(gravure
printing
inks,
vitrifiable
colors,
antifouling
agent,
dryers
for
paints
and
varnishes).
Tanshinones
are
abietane
diterpenes,
isolated
mainly
from
Salvia
miltiorrhiza
(Lamiaceae),
a
plant
largely
used
in
traditional
Chinese
medicine
for
the
treatment
of
cardiovascular
and
inflammatory
diseases.
Among
them,
tanshinone
I
is
an
apoptose
inductor
and
displays
several
anticancerous
biological
properties
[98].
Several
analogues
have
been
synthesized
for
clinical
trials.
Steviol
is
the
aglycone
of
stevia's
sweet
glycosides,
one
of
them
being
formed
by
replacing
one
hydrogen
atom
(bottom)
with
glucose
via
an
ester
link,
and
another
hydrogen
atom
(top)
with
a
disaccharide
(glucose
and
rhamnose).
The
steviol
glycosides
are
responsible
for
the
sweet
taste
of
the
leaves
of
the
stevia
plant
(Stevia
rebaudiana,
Asteraceae).
These
compounds
are
40
to
300
times
sweeter
than
sucrose.
They
are
developed
to
be
used
in
sweet
drinks.
Retene
is
present
in
tars
obtained
by
distillation
of
resinous
wood,
it
is
an
important
pollutant
eliminated
by
the
paper
factories.
This
diterpene
is
present
in
geological
sediment
where
it
is
formed
by
diagenesis
from
abietic
acid,
several
intermediates
having
been.
https://t.me/med1917
I
bus,
with
cadalene
(sesquiterpene),
retene,
a
diterpenoid
dehy-
ihop.cnation
product,
is
used
in
paleobotanic
to
estimate
the
importance
of
ancient
pine
forests.
Retene
Dehydroleucodine
Gibberellins
are
a
family
of
compounds,
over
130
members
■
xist.
The
most
important
in
plants
is
gibberellin
Al
which
is
и
sponsible
for
stem
elongation.
The
most
widely
available
<
(impound
is
gibberellic
acid
(one
double
bond
in
the
right
cycle).
.Among
the
physiological
properties,
gibberellins
are
involved
in
•mm
growth,
seed
germination
and
fruit
setting
and
growth.
Deliydroleucodine
was
isolated
from
Artemisia
douglasiana,
a
popular
medicinein
Argentina
and
was
shown
to
have
several
physiological
and
therapeutic
properties:
anti-proliferative
activity
in
(
i.
’
phase
[99],
cytoprotective
agent
for
gastric
ulcers
and
a
general
uni
ioxidant.
Cafestol
and
kahweol
are
present
in
high
concentrations
(up
to
18%
diterpene
esters)
in
the
oil
derived
from
coffee
beans.
The
only
difference
between
cafestol
and
kahweol
is
an
extra
double
bond
present
in
the
second
cycle
of
kahweol.
These
diterpenes
are
•■sterified
with
one
fatty
acid
(C14
to
C24),
palmitic
and
linoleic
hi
ids
being
the
major
esterified
fatty
acids.
Terpenes
were
also
shown
to
induce
an
elevated
plasma
cholesterol
content
in
human.
Cafestol
kahweol
https://t.me/med1917
Phorbol
is
a
diterpene
isolated
in
1934
from
croton
oil
(seeds
ol
Croton
tiglium).
Various
fatty
acid
esters
of
phorbol
have
important
biological
properties,
the
most
notable
of
which
is
the
capacity
to
ad
as
tumor
promoters
through
activation
of
protein
kinase
C
as
they
mimic
diacylglycerols.
The
most
common
phorbol
ester
is
phorbo
1
12-myristate-
13
-acetate
(PMA),
which
is
used
as
a
research
tool
in
models
of
carcinogenesis.
Phorbol
A
9
-Tetrahydrocannabinol
(THC)
Cannabinoids
are
a
group
of
diterpenes
present
in
Cannabis
(Cannabis
sativa
L).
All
these
substances
are
structurally
related
to
tetrahydrocannabinol
(THC)
and
are
able
to
bind
to
specific
cannabinoid
receptors.
Tetrahydrocannabinol,
also
known
as
A
9
-THC
or
A
9
-tetrahydrocannabinol,
is
the
main
psychoactive
substance
found
in
the
plant.
It
was
isolated
by
Mechoulam
R
et
al.
in
1964
[100].
Sesterterpens
They
are
derived
from
geranylfamesol
pyrophosphate
and
have
25
carbon
atoms
(the
sester-
prefix
means
half
to
three,
i.e.
two
and
a
half.).
These
relatively
rare
lipids
were
first
isolated
from
insect
protective
waxes
and
from
fungal
sources.
Now,
they
are
known
to
be
widespread,
they
have
been
isolated
from
terrestrial
fungi,
lichens,
higher
plants,
insects,
and
various
marine
organisms,
especially
sponges.
Geranyl
farnesol
https://t.me/med1917
11
icy
exhibit
diverse
biological
properties
such
as
anti
ml
I
и
minatory,
cytotoxic,
anticancer,
antimicrobial,
and
anti-biofilm
i.
uvilics.
The
structure
of
the
most
recent
sesterterpenoids
and
their
•H
livitics
have
been
reviewed
[101].
Three
examples
of
•
.tcrlcrpenes
are
shown
below.
Ophiobolin
A,
a
fungal
metabolite
and
a
phytotoxin
stimulates
lIn-
net
leakage
of
electrolytes
and
glucose
from
maize
seedling
roots
uni
was
found
to
be
a
potent
inhibitor
of
calmodulin-activated
cyclic
nucleotide
phosphodiesterase
[102].
Gascardic
acid
is
the
first
sesterterpenes
that
was
isolated
in
I
%5
from
the
secretion
of
an
insect,
Gascardia
madagascariensis.
Variously
unsaturated
and
branched
sesterterpenes,
known
as
I
Inslenes,
were
found
in
species
of
diatomaceous
algae
[103].
They
I
in
vc
25
carbons
and
3,
4
and
5
double
bonds.
They
are
widely
distributed
and
abundant
in
marine
sediments.
Several
haslenes
were
I
on
nd
to
be
produced
by
a
pennate
diatom
Haslea
ostrearia
uncording
to
the
culture
temperature
and
were
shown
to
have
cytostatic
properties.
One
of
them,
with
only
one
double
bond'and
known
as
IP25,
is
shown
below.
Ilaslene-C25
monounsaturated
isoprenoid
hydrocarbon
(IP25).This
compound
has
been
detected
in
sea
ice
in
Canadian
Arctic
and
was
shown
to
be
a
specific
biomarker
for
studying
the
Quaternary
Arctic
ice
history.
The
monitoring
of
this
lipid
appears
https://t.me/med1917
valuable
for
reconstruct
paleo-sea
ice
distributions
and
accurati
calibration
of
climate
prediction
models
[104-105].
4.5.
Triterpenoids
and
Steroids
They
form
a
large
group
of
natural
products
which
includes
steroids
and
consequently
sterols,
they
derived
from
C30
precursors.
Nearly
200
different
triterpene
skeletons
are
known
from
natural
sources
and
represent
structurally
cyclization
products
of
Squalene
which
is
the
immediate
biological
precursor
of
all
triterpenoids.
In
1934,
Robinson
proposed
a
direct
cyclization
of
squalene
to
the
steroid
molecule.
In
1936,
Nobel
laureate
researcher
Paul
Karrei
described
the
biochemical
structure
of
squalene
for
the
first
time.
It
has
major
specificities,
which
are
related
to
anticancer
properties,
the
maintenance
of
the
oxidation/antioxidation
balance,
and
its
antiaging
capabilities.
Shark
liver
oil
is
considered
the
richest
source
ol
squalene,
accounting
for
at
least
40%
of
its
weight.
It
is
also
widely
distributed
in
nature,
in
lesser
proportions
in
amaranth
oil
(6-9%),
in
wheat
germ
oil,
and
in
olive
oil
(usually
from
0.4%
up
to
1%
in
extra
virgin
olive
oil).
It
has
been
shown
that
the
human
body
synthesizes
an
average
amount
of
1.5
g/day
[106].
Biochemistry,
molecular
biology,
and
applications
of
squalene,
and
the
origin
of
their
skeletal
diversity
have
been
reviewed
[107].
Squalene
https://t.me/med1917
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