1
Nat. Vol. Essent. Oils, 2014; 1 (1): 1-50
REVIEW
Essential
Oils
of
Anatolian
Apiaceae
-‐
A
Profile¶
K.
Hüsnü
Can
Baser1,2and
Neş’e
Kırımer1
1
Anadolu
University,
Faculty
of
Pharmacy,
Department
of
Pharmacognosy,
26470
Eskişehir,
Turkey.
2
King
Saud
University,
College
of
Science,
Department
of
Botany
and
Microbiology,
Riyadh,
Saudi
Arabia
__________________________________________________________________________________________
Abstract
The
family
Apiaceae
is
represented
in
Turkey
by
101
genera
belonging
to
485
species
included
in
511
taxa
comprising
181
endemics,
7
genera
being
monotypic.
The
ratio
of
species
endemism
in
the
family
is
37.3
%.
We
have
screened
the
literature
for
Apiaceae
taxa
studied
for
their
essential
oils
and
compiled
the
data
in
order
to
get
a
clear
aromatic
profile
of
the
family.
It
has
become
obvious
that
our
group
has
been
very
active
in
this
matter.
We
have
so
far
investigated
taxa
belonging
to
58
genera
including
the
monotypic
genera
Ekimia
bornmuelleri,
Olymposciadium
caespitosum
and
published
on
their
essential
oil
yields
and
compositions.
Apiaceae
is
an
interesting
family
comprising
many
aromatic
taxa
including
commercialized
Herbas
and
spices
such
as
anis,
fennel,
cumin,
caraway,
coriander,
chervil,
parsley,
carrot,
asa
foetida,
galbanum,
etc.
Some
are
rich
in
essential
oils.
The
most
interesting
feature
of
the
family
is
that
many
of
its
members
have
high
chemical
diversity
containing
different
aromatic
chemicals
in
different
organs.
Therefore,
it
is
advisable
to
study
all
parts
(e.g.,
fruit,
flower,
stem,
leaf
and
root)
of
an
Apiaceae
plant
separately
in
order
to
get
a
complete
chemical
profile
of
that
taxon.
Apiaceae
genera
of
Turkey
studied
so
far
for
their
essential
oils
are
as
follows:
Actinolema,
Ammi,
Anethum,
Angelica,
Anthriscus,
Apium,
Artedia,
Bifora,
Bilacunaria,
Bunium,
Bupleurum,
Cachrys,
Chaerophyllum,
Cnidium,
Coriandrum,
Crithmum,
Cuminum,
Cymbocarpum,
Daucus,
Diplotaenia,
Echinophora,
Ekimia,
Eryngium,
Ferula,
Ferulago,
Foeniculum,
Fuernrohria,
Glaucosciadium,
Grammosciadium,
Heptaptera,
Heracleum,
Hippomaranthum,
Johrenia,
Kundmannia,
Lagoecia,
Laser,
Laserpitium,
Malabaila,
Myrrhoides,
Neocryptodiscus,
Olymposciadium,
Pastinaca,
Petroselinum,
Peucedanum,
Physocaulis,
Pimpinella,
Prangos,
Rhabdosciadium,
Scaligeria,
Scandix,
Seseli,
Smyrnium,
Szovitsia,
Tordylium,
Trachyspermum,
Trinia,
Xanthogalum,
Zosima.
KEYWORDS:
Review,
Apiaceae,
essential
oil,
Turkey
__________________________________________________________________________________________
¶Presented
as
a
plenary
lecture
at
the
2014
Apiales
Symposium
in
Istanbul,
Turkey
on
August
1-‐3.
2
Introduction
The
family
Apiaceae
is
represented
in
Turkey
by
101
genera
belonging
to
485
species
included
in
511
taxa
comprising
181
endemics
(=
E).
Endemic
monotypic
genera
include
Crenosciadium,
Microsciadium,
Olymposciadium,
Muretia,
Froriepia,
Stenotaenia
and
Ekimia.
Other
endemic
genera
are
Rhabdosciadium
(3
spp.)
and
Kundmannia
(2
spp.)
(Davis,
1972;
1988;
Duman
H.
and
Watson,
1999;
Ozhatay
et
al.
1994;
1999;
2009;
Guner
et
al.
2000,
Duran,
2014)
Apiaceae
species
are
rich
in
essential
oils.
They
may
contain
essential
oils
in
fruits,
flowers,
leaves,
roots
and
stem.
Chemical
diversity
is
so
varied
that
essential
oil
components
in
underground
and
aboveground
parts
may
vary
significantly.
Fruit
type
in
Apiaceae
is
schizocarp
meaning
that
seed
is
fused
with
the
fruit
in
such
a
way
that
it
is
impossible
to
separate
them
from
eachother.
This
is
the
reason
why
Apiaceae
fruits
are
often
called
seeds
such
as
aniseeds,
cumin
seeds,
coriander
seeds,
fennel
seeds,
etc.
Fruit
essential
oils
in
Apiaceae
are
contained
in
oil
ducts
called
vittae.
Such
subcutaneus
oils
give
higher
yields
when
crushed
before
distillation.
If
whole
fruits
are
distilled,
oxygenated
components,
which
are
generally
less
volatile
but
more
water
soluble,
appear
earlier
in
the
distillate.
This
can
be
explained
by
the
hydrodiffusion
phenomenon.
More
water
soluble
components
in
oil
ducts
diffuse
to
the
surface
of
the
fruit
and
are
carried
away
by
the
passing
steam.
More
volatile
but
less
water
soluble
hydrocarbons
are
eluted
later.
Hydrophobics
are
released
by
crushing
the
material
to
break
the
oil
ducts
prior
to
distillation.
Heating
of
the
material
facilitates
the
removal
of
hydrocarbons.
Crushing
the
fruits
prior
to
distillation
facilitates
distillation
of
hydrocarbons
as
well
as
other
components.
Several
Apiaceae
species
are
ingredients
of
foods
and
therefore
their
large
scale
cultivation
is
required.
Surplus
of
domestic
use
is
generally
exported.
Major
Apiaceae
crops
cultivated
in
Turkey
are
aniseed
(Pimpinella
anisum),
cumin
(Cuminum
cyminum),
coriander
(Coriandrum
sativum),
fennel
(Foeniculum
vulgare).
Some
lesser
crops
cultivated
or
used
in
Turkey
include
celery
(Apium
graveolens),
dill
(Anethum
graveolens),
parsley
(Petroselinum
sativum)
and
laser
(Laser
trilobum).
In
2013,
Turkey
exported
7.942
tons
of
cumin
fruits
for
a
return
of
USD
20.5
million.
Exports
of
aniseeds
amounted
to
1.944
tons
for
a
return
of
USD
7.9
million.
15
years
ago
it
was
4.000
tons.
When
Turkish
State
Monopolies
(TEKEL)
used
to
purchase
7000
tons
annually
for
the
production
of
an
alcoholic
drink
called
RAKI
(Baser,
1997b).
Since
then,
TEKEL
has
been
privatized
and
the
state
monopoly
over
RAKI
has
been
lifted.
Therefore,
most
of
the
aniseed
production
is
consumed
by
the
domestic
Raki
producers
and
only
a
small
surplus
is
exported.
Export
figures
of
fennel
and
juniper
are
collectively
cited
under
the
same
HS
(Harmonised
system)
code
in
export
statistics.
Their
combined
exports
amounted
to
894.292
kg
in
2011
for
a
return
of
USD
2.5
million.
Coriander
exports
of
Turkey
in
2013
were
229
tons
for
USD
566.088
(Table
1).
3
Table
1.
Export
of
Some
Apiaceae
Crops
of
Turkey
1997
2013
Aniseed
kg
3.907.492
1.944.227
$
8.891.921
7.889.501
$/kg
2.28
4.05
Cumin
kg
12.927.275
7.941.924
$
19.489.209
20.574.613
$/kg
1.51
2.59
Fennel
/
kg
1.699.129
894.292*
Juniper
fruit
$
1.873.348
2.500.000*
$/kg
1.10
1.33*
Coriander
kg
228.596
$
566.088
$/kg
2.48
*2011
figures
Technical
Information
1.
Unless
stated
otherwise,
all
the
oils
were
obtained
by
water
distillation
using
a
laboratory-‐
scale
Clevenger
apparatus.
2.
For
micro-‐distillation,
either
an
Eppendorf
MicroDistiller
or
a
Likens-‐Nickerson
Simultaneous
Distillation-‐Extraction
apparatus
were
used.
3.
Unless
stated
otherwise,
all
plant
materials
were
ground
prior
to
distillation.
4.
For
Gas
Chromatographic
/
Mass
Spectrometric
Analysis,
a
Shimadzu
QP2000A,
QP5050,
a
Hewlett-‐Packard
G1800A
MSD
and
Agilent
5975GCMSD
systems
were
used.
5.
For
chiral
separations,
the
Multi-‐Dimensional
Gas
Chromatography/Mass
Spectrometry
(MDGC/MS)
system
used
consisted
of
two
HP-‐GC6890
gas
chromatographs
+
HP-‐MSD
+
Gerstel
MCS
system.
Apiaceae
Oils
of
Turkey
CUMIN
SEED
OIL
(Cuminum
cyminum
L.)
Cumin
(Kimyon
in
Turkish)
is
an
annual
plant
cultivated
for
its
use
as
condiment
and
as
an
ingredient
of
sucuk
(spicy
meaty
Turkish
sausages).
15
essential
oil
samples
from
Turkey
and
four
from
abroad
were
subjected
to
analysis
and
the
results
are
summarised
in
Table
2
(Baser
et
al.,
1992).
The
following
generalities
can
be
drawn
from
the
results.
1.
p-‐Mentha-‐1,4-‐dien-‐7-‐al
(γ-‐terpinen-‐7-‐al)
predominates
over
the
other
components
in
lab-‐
distilled
oils.
2.
Total
aldehydes
content
in
lab-‐distilled
oils
varies
between
61-‐78%
while
in
commercial
oils
it
falls
between
29-‐46%.
3.
Monoterpene
hydrocarbons
predominate
over
the
aldehydes
in
commercial
oils
(32-‐66%)
4.
In
commercial
Turkish
and
Egyptian
oils
cuminaldehyde
is
the
main
constituent
while
γ-‐
terpinene
is
the
main
component
in
Indian
oils.
4
5.
p-‐Mentha-‐1,4-‐dien-‐7-‐al
(γ-‐terpinen-‐7-‐al)
is
the
main
component
in
fresh
seeds.
It
is
easily
oxidised
to
cuminaldehyde
in
pre-‐ground
seeds
during
storage
or
during
the
heat
treatment
associated
with
distillation
of
the
commercial
oil.
Table
2.
Cumin
seed
oil
Water
distilled
whole
ground
Steam
distilled
whole
ground
Yield
(%)
p-‐mentha-‐1,4-‐dien-‐
7-‐al
(α-‐terpinen-‐7-‐al)
cuminaldehyde
p-‐mentha-‐1,3-‐dien-‐
7-‐al
(α-‐terpinen-‐7-‐al)
p-‐cymene
γ-‐terpinene
β-‐pinene
1.2-‐3.2
31-‐49
1.4-‐1.6
25-‐38
1.2
41
1.2-‐1.7
28-‐32
2-‐8
6
2-‐3
19-‐25
4-‐12
21-‐25
4-‐12
26
12
21-‐27
6-‐11
22-‐40
8-‐13
20
9
20-‐31
7-‐11
5-‐9
7-‐11
3-‐7
6
14-‐15
7-‐8
5
7
3
6
14-‐16
6-‐9
6-‐9
11-‐23
8-‐16
9
18
10
14-‐18
29-‐32
4-‐13
Turkish
Commercial
Egyptian
Indian
We
have
also
published
on
the
hydrodistilled
essential
oils
of
unripe,
ripe
and
fully
ripe
cumin
fruits
cultivated
in
Konya
(Table
3).
Table
3.
Cumin
seed
oils
at
different
vegetative
states
(Kan
et
al,
2007)
Yield
(%)
p-‐mentha-‐1,4-‐dien-‐7-‐al
(=
γ-‐terpinen-‐7-‐al)
cuminaldehyde
p-‐mentha-‐1,3-‐dien-‐7-‐al
(=
γ-‐terpinen-‐7-‐al)
p-‐cymene
γ-‐terpinene
α-‐phellandrene
β-‐pinene
Total
aldehydes
1.9
16.9
19.9
14.1
7.7
10.3
8.5
8.7
50.9
2.4
13.9
23.6
17.5
9.6
11.5
4.1
7.4
65.0
2.3
16.0
20.4
11.4
11.6
13.6
5.4
9.0
55.8
Impact
compounds
of
the
cumin
fruit
oil
are
the
three
aldehydes.
Their
total
percentages
amounted
to
50.9%,
65.0%
and
55.8%
in
unripe,
ripe
and
fully
ripe
fruits,
resp.
(Kan
et
al,
2007).
Another
paper
on
the
Turkish
cumin
seed
oil
reported
only
cuminaldehyde
as
55%
together
with
edulan
(10%)
and
carotol
(5%)
without
mention
of
other
aldehydes
and
monoterpenes.
Scientific
value
of
this
paper
is
questionable
(Topal
et
al.,
2008).
Our
group
has
also
determined
the
steam
distillation
process
parameters
of
cumin
seed
oil
using
a
500
liter
pilot
plant.
Optimum
conditions
for
the
best
yield
of
oil
were
found
as
0.5
mm
particle
size,
35
kg
batch
size,
distillation
rate
0.28
kg/
kg-‐1h-‐1,
distillation
time
3
h.
Major
components
were
found
as
cuminaldehyde
27.6%,
γ-‐terpinene
17.3%,
p-‐mentha-‐1,3-‐dien-‐7
al
(γ-‐terpinen-‐7-‐al)
15.2%,
β-‐pinene
10.2%,
p-‐mentha-‐1,4-‐dien-‐7-‐al
(γ-‐terpinen-‐7-‐al)
9.5%
(Beis
et
al.,
2000).
Bunium
persicum
(Boiss.)
B.Fedtsch.
(Umbelliferae)
is
also
a
native
plant
of
Turkey
with
no
reported
use.
However,
the
fruits
of
this
species
are
used
in
place
of
cumin
in
Central
Asia,
Afghanistan
and
Pakistan.
The
analysis
of
fruits
of
Bunium
persicum
from
Tajikistan
revealed
the
presence
of
p-‐mentha-‐
1,4-‐dien-‐7-‐al
γ-‐terpinen-‐7-‐al)
(29%),
γ-‐terpinene
(26%),
β-‐pinene
(16%)
and
cuminaldehyde
(12%)
as
main
constituents
(Baser
et
al,
1997a).
5
LASER
SEED
OIL
(Laser
trilobum
(L.)
Borkh.)
Laser
is
an
erect,
glaucous
perennial
plant
attaining
a
height
of
ca.
120
cm
which
grows
wild
scattered
throughout
Turkey
except
in
the
Southest
region.
Dried
ripe
fruits
known
as
“kefe
kimyonu”
is
traded
and
used
as
a
spice
in
Turkey.
The
fruits
have
a
cumin-‐like
aroma
with
a
resinous
and
spicy
taste.
A
2%
decoction
of
the
fruit
is
applied
on
the
skin
for
acne.
Fruits
from
two
localities
in
Turkey
were
subjected
to
different
distillation
modes
and
the
oils
were
analysed.
The
results
are
summarised
in
Table
4
(Baser
et
al,
1993).
1.
Perillaldehyde
and
limonene
are
the
main
constituents
of
Laser
seed
oil.
Limonene
is
a
monoterpene
hydrocarbon.
Perillaldehyde
is
an
oxygenated
monoterpene.
2.
Due
to
reasons
already
explained,
perillaldehyde
is
the
main
constituent
in
essential
oil
distilled
from
whole
fruits.
Crushed
fruits
or
predistilled
whole
fruits
yield
oil
rich
in
limonene.
3.
Prolonged
storage
or
heat
treatment
of
Laser
seeds
produce
an
oil
rich
in
perillaldehyde
due
to
higher
volatility
of
limonene.
Table
4.
Laser
seed
oil
Yield
(%)
perillaldehyde
limonene
whole
2-‐3
62-‐69
27-‐29
ground
5-‐7
29-‐34
65-‐69
Water
distilled
heated
cad
whole
2-‐6
2
4-‐8
67
88-‐91
22
heated
ad
1
80
6
Steam
distilled
whole
ground
2
6
72
31
19
63
Cad:
Crushed
after
distillation
of
the
whole
fruits.
Another
recent
study
on
laser
fruits
reported
the
yield
of
essential
oil
as
4.4-‐5.8%
with
limonene
(41-‐
72%)
and
perillaldehyde
(4-‐33%)
as
main
constituents
(Parlatan
et
al,
2009).
APIACEAE
OILS
OF
OTHER
COMMERCIAL
CROPS
Table
5
summarises
the
results
of
analysis
of
the
essential
oils
of
some
commercial
Apiaceae
crops
carried
out
at
our
laboratories.
Table
5.
Main
components
of
the
essential
oils
of
some
commercial
genera
Common
name
Latin
name
%
yield
Main
components
(%)
Carrot
seed
Daucus
carota
2.5
carotol
27
0.83
carotol
67
Celery
Herba
Apium
graveolens
0.09
γ-‐terpinene
39
Chervil
Herba
Anthriscus
cerefolium
0.4
methyl
chavicol
83,
1-‐allyl-‐2,4-‐
di-‐methoxy
benzene
15
Coriander
seed
Coriandrum
sativum
0.4-‐2.0
(+)-‐linalool
89
Dill
seed
Anethum
graveolens
2.0-‐2.5
(+)-‐carvone
46-‐66
Parsley
seed
Petroselinum
sativum
0.5
2,3,4,5-‐tetramethoxy
allylbenzene
29
Angelica
seed
Angelica
sylvestris
var.
0.26
α-‐pinene
26,
β-‐phellandrene
9,
sylvestris
bornyl
acetate
7,
p-‐cresol
7
Ref.
Baser,
2002
Ozcan
&
Chalchat,
2007
Baser,
2002
Baser
et
al.,
1998a
Baser,
2002
Kosar
et
al.,
2005
Baser,
2002
Ozek,
T.,
et
al.,
2008
6
FENNEL
OILS
Foeniculum
vulgare
var.
dulce
oil
contains
trans-‐anethole
80-‐95%
as
the
main
constituent
with
methyl
chavicol
(estragole)
3-‐16%
as
a
minor
component.
In
the
oil
of
F.
vulgare
var.
piperitum
methyl
chavicol
22-‐70%
is
the
main
constituent,
fenchone
13-‐28%
is
second
major
component.
Trans-‐anethole
content
is
very
low.
F.
vulgare
var.
vulgare
oils
are
characterized
by
high
trans-‐anethole
content
which
is
lower
than
that
of
F.
vulgare
var.
dulce.
Trans-‐anethole
and
methyl
chavicol
contents
are
similar
in
percentage
values.
Due
to
higher
methyl
chavicol
contents
this
taxon
is
also
called
as
bitter
fennel.
Table
6.
Fennel
oils
Common
name
Fennel
seed,
sweet
Latin
name
Part
Foeniculum
vulgare
var.
Fruit
vulgare
Fruit
Fruit
Fennel
seed,
bitter
Florence
finocchio
Foeniculum
vulgare
var.
Fruit
dulce
Foeniculum
vulgare
var.
Fruit
piperitum
Leaf
%
yield
2.4-‐3.1
3.1
6-‐12
3
4.3-‐7.7
1-‐3
Root
0.17
Stem
0.87
fennel,
Foeniculum
vulgare
var.
Fruit
azoricum
Main
components
(%)
trans-‐anethole
65-‐88
trans-‐anethole
75,
methyl
chavicol
16
trans-‐anethole
81-‐88,
methyl
chavicol
4-‐6,
fenchone
1-‐3
trans-‐anethole
95,
methyl
chavicol
3
methyl
chavicol
63-‐73,
fenchone
18-‐28
methyl
chavicol
25-‐70,
fenchone
8-‐15,
limonene
2-‐10,
fenchylacetate
2-‐14
methyl
chavicol
59,
fenchone
12,
fenchylacetate
3
methyl
chavicol
61,
fenchone
25
trans-‐anethole
59-‐72,
limonene
8-‐11,
apiole
tr-‐9
Ref.
Baser,
2002
Cosge
et
al.,
2008
Telci
et
al.,
2009
Cosge
et
al.,
2008
Baser,2002
Figueredo
2011
et
al.,
Özcan
&
Chalchat
2010
Özcan
&
Chalchat
2010
Cetin
et
al,
2010
CORIANDER
OIL
Coriander
(Coriandrum
sativum)
is
a
cultivated
crop
whose
fresh
leaves
and
fruits
are
used
as
condiment
and
as
a
source
of
essential
oil.
Fruit
oil
is
a
rich
source
of
the
rare
(+)-‐linalool
and
therefore
important
as
a
perfumery
ingredient.
Fresh
leaves,
rich
in
aliphatic
aldehydes
such
as
(E)-‐2-‐decenal,
are
added
to
soups
and
salads
due
to
its
pungent
taste.
Table
7.
Coriander
oils
Plant
name
Coriandrum
sativum
Part
Fruit
%
yield
0.3-‐1.2
Main
components
%
linalool
(16)
72-‐83
C.
sativum
var.
vulgare
C.
sativum
var.
macrocarpum
C.
sativum
var.
microcarpum
Fruit
Fruit
0.2-‐0.4
linalool
30-‐65
linalool
79
Fruit
Fruit
Fruit
Herba
0.3-‐0.4
0.35-‐0.61
0.5
linalool
64-‐71
linalool
91
linalool
37-‐77
(E)-‐2-‐decenal
17-‐35
(spring);
11-‐51
(summer)
decanal
19-‐23
(autumn);
10-‐18
(summer)
Ref.
Kiralan
et
al.,
2009;
Sampson
et
al.,
2005;
Koşar
et
al
2005;
Yıldırım
&
Gok,
2012.
Telci
et
al.,
2006a;
2006b.
Duman
A.D.
et
al.,
2010
Telci
et
al.,
2006b
Duman
A.D.
et
al.,
2010
Telci
et
al.,
2006a
Telci
&
Hisil,
2008a
7
PIMPINELLA
ESSENTIAL
OILS
The
genus
Pimpinella
is
represented
in
Turkey
by
25
species,
and
altogether
29
taxa,
7
being
endemic
(Duran
2014).
Essential
oils
of
20
taxa
were
analysed
by
our
group.
The
results
are
summarized
in
Table
8.
Pimpinella
oils
are
characterized
by
high
contents
of
phenylpropanoid
derivatives.
Kubeczka
has
classified
phenylpropanoids
as
two
specific
types,
a
propenylphenol-‐type
(4-‐monosubstituted
phenylpropanoid)
and
a
pseudoisoeugenol-‐type
(2,5-‐disubstituted
phenylpropanoid)
(Kubeczka,
1998).
The
2-‐hydroxy-‐5-‐methoxy-‐1-‐(E)-‐propenylbenzene
skeleton
of
these
compounds,
known
as
pseudoisoeugenol,
is
unique
to
Pimpinella.
Trinorsesquiterpenes
(geijerenes
and
azulenes)
were
also
found
to
be
characteristic
constituents
in
most
Pimpinella
oils
(Baser
et
al.,
2007b)
Oil
yields
of
the
fruits
of
Pimpinella
species
were
as
follows:
P.
nudicaulis
(5.10%),
P.
anisetum
(5.3-‐
5.05%),
P.
aurea
(5.1%),
P.
anisum
(4.8-‐1.3
%),
P.
affinis
(2.12%),
P.
cappadocica
var.
cappadocica
(2.06-‐0.3
%),
P.
flabellifolia
(1.88%),
P.
tragium
subsp.
pseudotragium
(1.87%),
P.
saxifraga
(1.67%),
P.
isaurica
(1.4-‐1.3%),
P.
peregrina
(1.08%),
P.
kotschyana
(1.02%),
P.
tragium
subsp.
polyclada
(0.92%),
P.
tragium
subsp.
lithophila
(0.73-‐
0.71%),
P.
rhodantha
(0.41%),
P.
puberula
(0.32%),
P.
corymbosa
(0.26%),
P.
peucedanifolia
(0.23%),
P.
olivieroides
(0.20%).
P.
aromatica
and
P.
anisetum
roots
gave
the
highest
oil
yields
(4.2
and
3.2%,
resp.
).
Oil
yield
of
P.
aromatica
Herba
was
6.1%
and
of
P.
anisetum
3.0%.
Oil
of
the
cultivated
anis
(Pimpinella
anisum)
with
3-‐5%
yield
contained
trans-‐anethole
(85-‐96%)
as
the
main
constituent
which
crystallizes
out
easily
by
freezing.
Crushed
fruits
of
the
endemic
P.
anisetum
gave
a
high
yield
of
oil
(3-‐5%)
with
relatively
high
percentage
of
trans-‐anethole
(55-‐83%)
and
methyl
chavicol
(22%).
Herbaal
parts
of
the
same
species
yielded
an
oil
also
rich
in
trans-‐anethole
(55%)
and
methyl
chavicol
(42%).
The
oil
from
Herbaal
parts
of
P.
aromatica
obtained
in
high
yield
(6.1%)
was
a
rich
source
of
methyl
chavicol
(92%).
Essential
oil
from
roots
of
the
same
plant
gave
a
totally
different
picture
than
the
Herba
in
that
the
main
constituent
was
2-‐methylbutanoate
of
trans-‐pseudoeugenol
(40%).
Compounds
responsible
for
the
blue
colour
of
the
root
oil
were
two
azulene
derivatives.
Herba
oil
of
P.
isaurica,
another
endemic
species,
contained
high
proportion
of
angelic
and
tiglic
acid
esters
of
chavicol
(44%).
Fruits
and
Herbas
of
P.
cappadocica
(E)
and
P.
corymbosa
were
relatively
poor
in
essential
oil.
The
oils
contained
sesquiterpenes
as
main
constituents
(Table
8).
Of
the
22
isolated
compounds
during
this
investigation,
two
new
phenylpropanoids,
4-‐(prop-‐2-‐
enyl)phenyl
angelate,
and
4-‐(3-‐methyloxiranyl)phenyl
2-‐methylbutyrate,
one
new
bisabolene-‐type
sesquiterpenoid,
1-‐methyl-‐4-‐(6-‐methylhepta-‐1,5-‐dien-‐2-‐yl)-‐7-‐oxabicyclo
[4.1.0]heptane
(“aureane”),
and
one
new
trinorsesquiterpene,
4-‐(6-‐methylbicyclo[4.1.0]hept-‐2-‐en-‐7yl)butan-‐2-‐one
(“traginone”),
were
identified
and
characterized
by
spectral
techniques
(Tabanca
et
al.,
2006).
Six
further
compounds
were
identified
for
the
first
time
as
constituents
of
Apiaceae,
whilst
trans-‐isoosmorhizole,
was
identified
for
the
first
time
as
a
constituent
of
Pimpinella
species.
Nine
known
phenylpropanoids,
as
well
as
trans-‐anethole
and
methyl
eugenol,
were
isolated
and
identified
from
different
Pimpinella
oils.
The
properties
of
known
compounds
were
compared
with
previously
published
data,
and
after
identification
were
registered
in
the
“Baser
Library
of
Essential
Oil
Constituents”.
Pimpinella
oils
were
reanalyzed
by
GC/MS,
and
those
isolated
compounds
were
detected
in
other
Pimpinella
oils
(Table
8).
Oils
from
four
Pimpinella
taxa
(P.
anisum,
P.
nudicaulis,
and
two
endemic
taxa
8
P.
anisetum,
P.
flabellifolia)
were
rich
in
trans-‐anethole.
Pimpinella
anisetum
and
P.
anisum
fruit
oils
were
characterized
by
higher
contents
of
trans-‐anethole
(81–94
%)
than
the
other
species.
Trinorsesquiterpenes
geijerene
and
pregeijerene
were
main
constituents
in
the
oils
of
P.
affinis
and
P.
tragium
subsp.
lithophylla.
P.
saxifraga
and
P.
puberula
oils
were
rich
in
monoterpenes
and
P.
peucedanifolia
oil
was
unique
in
having
undecane
(an
alkane)
as
main
constituent
in
the
oil.
P.
cappadocica,
P.
corymbosa,
P.
kotschyana,
P.
peregrina,
P.
tragium
subsp.
lithophila,
P.
tragium
subsp.
polyclada,
P.
tragium
subsp.
pseudotragium
oils
were
rich
in
sesquiterpenes.
Methyl
eugenol
was
a
major
constituent
in
the
oils
of
P.
oliveiroides
and
P.
puberula.
9
Table
8.
Pimpinella
oils
of
Turkey
Plant
name
P.
affinis
Part
Fruit
%
yield
2.12
Stem+Leaf
0.09
Root
0.23
P.
anisum
Fruit
1.6
1.3-‐3.7
2.8-‐4.8
3.4
P.
anisetum
(E)
Fruit
5.3
5.05
P.
aromatica
P.
aurea
Stem+Leaf
1.06
Herba
Herba
Root
3.0
2.07
3.2
Herba
6.1
Root
4.2
Fruit
5.1
Stem+Leaf
0.3
Root
0.1
Main
components
(%)
geijerene
59,
pregeijerene
20,
dictamnol
2,
traginone
1*
geijerene
40,
pregeijerene
11,
traginone
5*,
dictamnol
4,
epoxypseudoisoeugenyl
2-‐
methylbutyrate
0.2,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylangelate
0.2
geijerene
36,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylangelate
11,
pregeijerene
9,
epoxypseudoisoeugenyl
2-‐
methylbutyrate
2,
traginone
1*,
dictamnol
1
trans-‐anethole
96
trans-‐anethole
79-‐95
trans-‐anethole
85-‐92
trans-‐anethole
85,
methyl
chavicol
16
Ref.
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Baser,
2002
Arslan
et
al.,
2004
Ozel,
2009
Sampson
et
al.,
2005
trans-‐anethole
77,
methyl
chavicol
22
Baser
et
al.,
1999a
trans-‐anethole
81,
methyl
chavicol
16,
4-‐ Tabanca
et
al.,
methoxy-‐2-‐(prop-‐(1E)-‐enyl)phenyl
angelate
2006
0.2
trans-‐anethole
54,
epoxypseudoisoeugenyl
Tabanca
et
al.,
2-‐methylbutyrate
24,
methyl
chavicol
13,
4-‐ 2006
methoxy-‐2-‐3-‐methyloxiranyl)-‐
phenylangelate
5,
4-‐methoxy-‐2-‐(prop-‐(1E)-‐
enyl)phenyl
angelate
0.2,
dictamnol
0.2
trans-‐anethole
55,
methyl
chavicol
42
Baser,
2002
trans-‐anethole
83,
methyl
chavicol
15
Tepe
et
al.,
2006
epoxypseudoisoeugenyl
2-‐methylbutyrate
Tabanca
et
al.,
56,
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐
2006
phenylangelate
8,
dictamnol
0.5,
methyl
chavicol
92,
trans-‐anethole
7
Baser
et
al.,
1996b
trans-‐epoxypseudoeugenyl-‐2-‐
Baser
et
al.,
methylbutyrate
40,
4,10-‐dihydro-‐1,4-‐ 1996b
dimethylazulene
17,
1,4-‐dimethylazulene
9,
pregeijerene
5
aureane
34*,
β-‐bisabolene
33,
4-‐(prop-‐(1E)-‐
Tabanca
et
al.,
enyl)phenyl
tiglate
2.5,
4-‐(3-‐
2006
methyloxiranyl)phenyl-‐2-‐methylbutyrate*
1.2,
4-‐[(2R,3R)-‐3-‐methyloxiranyl]phenyl
tiglate
0.3
aureane
20*,
sabinene
20,α-‐pinene
12,
b-‐
Tabanca
et
al.,
bisabolene
9,
4-‐(prop-‐(1E)-‐enyl)phenyl
2006
tiglate
1.2,
4-‐(3-‐methyloxiranyl)phenyl-‐2-‐
methylbutyrate*
0.4
epoxypseudoisoeugenyl
2-‐methylbutyrate
Tabanca
et
al.,
39,
aureane
10*,
4-‐(3-‐
2006
methyloxiranyl)phenyl-‐2-‐methylbutyrate*
2,
4-‐(prop-‐(1E)-‐enyl)phenyl
tiglate
1.6
10
P.
cappadocica
Fruit
var.
cappadocica
(E)
P.
corymbosa
P.
flabellifolia
(E)
P.
isaurica
(E)
0.3
2.06
Stem+Leaf
0.14
Herba
Root
0.7
0.18
Fruit
0.2
0.3
Herba
Stem+Leaf
0.1
0.2
Root
0.2
Fruit
1.88
Stem+Leaf
0.85
Herba
Root
2.61
1.43
Herba
Stem+Leaf
1.3
0.3
Fruit
1.43
Root
0.31
caryophyllene
oxide
26
bicyclogermacrene
12,
γ-‐himachalene
9,
β-‐
caryophyllene
9,
dehydrocostuslactone
8,
sabinene
6,
epoxypseudoisoeugenyl
2-‐
methylbutyrate
0.1
sabinene
17,
germacrene
D
6,
epoxypseudoisoeugenyl
2-‐methylbutyrate
0.6,
himachalol
16
epoxypseudoisoeugenyl
2-‐methylbutyrate
43,
4-‐(1-‐propenyl)-‐phenyl-‐2-‐methylbutyrate
19,
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylangelate
3,
traginone
0.1*,
4-‐(prop-‐
(1E)-‐enyl)phenyl
tiglate
0.1,
dictamnol
0.1
β-‐caryophyllene
14,
caryophyllene
oxide
11
β-‐caryophyllene
33,
germacrene
D
9,
12-‐
hydroxy-‐β-‐caryophyllene
acetate
5,
4,6-‐
guaiadiene
0.6,
β-‐caryophyllene
38,
caryophyllene
oxide
17
β-‐caryophyllene
33,
germacrene
D
12,
12-‐
hydroxy-‐β-‐caryophyllene
acetate
3,
4-‐(1-‐
prop-‐(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
0.4,
epoxypseudoisoeugenyl
2-‐
methylbutyrate
0.1
epoxypseudoisoeugenyl-‐2-‐methylbutyrate
43,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐
methylbutyrate
33,
4-‐(prop-‐(1E)-‐enyl)phenyl
isobutyrate
0.5,
12-‐hydroxy-‐β-‐caryophyllene
acetate
0.04
trans-‐anethole
64,
limonene
28,
trans-‐anethole
41,
limonene
17,
trans-‐
isoosmorhizole
0.1
limonene
47,
trans-‐anethole
38
trans-‐anethole
68,
limonene
17,
trans-‐
isoosmorhizole
2
chavicyl
angelate
44
4-‐(prop-‐2-‐enyl)phenyl
angelate*
43,
4-‐(prop-‐
(1E)-‐enyl)phenyl
tiglate
13,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylangelate
3,
4-‐
methoxy-‐2-‐(prop-‐(1E)-‐enyl)phenyl
angelate
0.5,
α-‐zingiberene
16,
4-‐(prop-‐2-‐enyl)phenyl
angelate*
14,
4-‐(prop-‐(1E)-‐enyl)phenyl
tiglate
1.4,
alismol
0.4,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylangelate
0.1
γ-‐terpinene
17,
4-‐(prop-‐(1E)-‐enyl)phenyl
tiglate
16,
4-‐(prop-‐2-‐enyl)phenyl
angelate*
11,
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylangelate
7,
4-‐methoxy-‐2-‐(prop-‐(1E)-‐
enyl)phenyl
angelate
0.2
Baser,
2002
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Baser,
2002
Tabanca
et
al.,
2006
Baser,
2002
Tabanca
et
al.,
2005
Baser,
2002
Tabanca
et
al.,
2005
Tabanca
et
al.,
2005
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tepe
et
al.,
2006
Tabanca
et
al.,
2006
Baser,
2002
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
11
P.kotschyana
P.
nudicaulis
P.
oliveiroides
P.
peregrina
Fruit
1.02
Stem+Leaf
0.06
Root
0.10
Fruit
5.10
Stem+Leaf
1.29
Root
0.31
Fruit
0.20
Stem+Leaf
0.27
Root
0.06
Fruit
1.1
Stem+Leaf
0.1
Root
0.1
β-‐caryophyllene
49,
12-‐hydroxy-‐β-‐
caryophyllene
acetate
12,α-‐humulene
11,
4,6-‐guaiadiene
2.1,
4-‐(Prop-‐(1E)-‐enyl)phenyl
isobutyrate
0.3,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
0.1,
dictamnol
0.01
β-‐caryophyllene
40,
α-‐humulene
9,
12-‐
hydroxy-‐β-‐caryophyllene
acetate
5,
4,6-‐
guaiadiene
2.4,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
0.3,
dictamnol
0.1
epoxypseudoisoeugenyl
2-‐methylbutyrate
36,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐
methylbutyrate
34,
4-‐(Prop-‐(1E)-‐enyl)phenyl
isobutyrate
0.8,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylisobutyrate
0.7,
4,6-‐
guaiadiene
0.6,
dictamnol
0.3,
12-‐hydroxy-‐b-‐
caryophyllene
acetate
0.04
trans-‐anethole
64,
trans-‐isoosmorhizole
21,
aureane
0.02*
trans-‐anethole
28,
α-‐pinene
17,
β-‐pinene
15,
trans-‐isoosmorhizole
12,
sabinene
11,
aureane
0.1*
trans-‐isoosmorhizole
79,
trans-‐anethole
13,
aurean
0.1*
methyl
eugenol
71,
cis-‐isoelemicine
14,
4-‐(1-‐
prop-‐(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
0.1,
epoxypseudoisoeugenyl
2-‐
methylbutyrate
0.03
methyl
eugenol
52,
cis-‐isoelemicine
5,
epoxypseudoisoeugenyl
2-‐methylbutyrate
0.5
4-‐(1-‐Prop-‐(1E)-‐enyl)phenyl
(2S)-‐
methylbutyrate
39,
epoxypseudoisoeugenyl
2-‐methylbutyrate
33,
4,10-‐dihydro-‐1,4-‐
dimethylazulene
6
trans-‐β-‐bergamotene
41,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylisobutyrate
4,
aureane*
1,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐
methylbutyrate
0.3
trans-‐β-‐bergamotene
70,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylangelate
8,
4-‐
methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylisobutyrate
6,
aureane*
3,
4-‐(1-‐prop-‐
(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
2,
trans-‐isoosmorhizole
0.3,
4,6-‐guaiadiene
0.1
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylisobutyrate
45,
epoxypseudoisoeugenyl-‐2-‐methylbutyrate
27,
β-‐sesquiphellandrene
10,
4-‐(3-‐
methyloxiranyl)phenyl-‐2-‐methylbutyrate
*
0.3,
aureane*
0.2,
4-‐(1-‐prop-‐(1E)-‐
enyl)phenyl
(2S)-‐methylbutyrate
0.1,
4-‐
methoxy-‐2-‐(3-‐methyloxiranyl)-‐
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2005
Tabanca
et
al.,
2005
Tabanca
et
al.,
2005
12
P.
peucedanifolia
P.
puberula
P.
rhodantha
P.
saxifraga
Fruit
0.23
Stem+Leaf
0.01
Root
0.13
Fruit
0.3
Stem+Leaf
0.2
Fruit
0.41
Stem+Leaf
0.06
Root
0.10
Fruit
1.67
Stem+Leaf
0.32
Root
0.17
phenylangelate
8,
undecane
77,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
2,
4-‐(prop-‐(1E)-‐
enyl)phenyl
isobutyrate
1.8,
alismol
0.3
undecane
65,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
3,
epoxypseudoisoeugenyl
2-‐methylbutyrate
0.8,
dictamnol
0.3,
4-‐(Prop-‐(1E)-‐enyl)phenyl
isobutyrate
0.1
epoxypseudoisoeugenyl
2-‐methylbutyrate
83,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐
methylbutyrate
6,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylisobutyrate
2.4,
4-‐(3-‐
methyloxiranyl)
phenyl-‐2-‐methylbutyrate*1
limonene
63,
methyl
eugenol
23,
dictamnol
0.6,
traginone*
0.2
limonene
37,
methyl
eugenol
30,
dictamnol
3,
traginone*
1,
epoxypseudoisoeugenyl
2-‐
methylbutyrate
0.1
(Z)-‐β-‐farnesene
35,
β-‐bisabolene
33,
γ-‐
himachalene
9,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylangelate
0.8,
4-‐Methoxy-‐2-‐(prop
(1E)-‐enyl)phenyl
tiglate
0.2
germacrene
D
17,
(Z)-‐β-‐farnesene
13,
4-‐
methoxy-‐2-‐(3-‐methyloxiranyl)-‐phenyltiglate
6,
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylangelate
2.5,
alismol
1.4,
epoxypseudoisoeugenyl
2-‐methylbutyrate
0.5,
4-‐Methoxy-‐2-‐(prop
(1E)-‐enyl)phenyl
tiglate
0.5,
dictamnol
0.4
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenyltiglate
29,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylangelate
29,
β-‐eudesmol
9,
4-‐Methoxy-‐2-‐(prop
(1E)-‐
enyl)phenyl
tiglate
2,
alismol
0.7,
dictamnol
0.2,
epoxypseudoisoeugenyl
2-‐
methylbutyrate
0.2,
traginone*
0.1
sabinene
41,
β-‐pinene
21,
myrcene
14,
4-‐(1-‐
prop-‐(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
1.5,
4-‐(3-‐methyloxiranyl)phenyl-‐2-‐
methylbutyrate*
1,
epoxypseudoisoeugenyl
2-‐methylbutyrate
0.2
β-‐pinene
28,
myrcene
19,
sabinene
14,
limonene
11,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
1.3,
epoxypseudoisoeugenyl
2-‐methylbutyrate
0.6,
4-‐(3-‐methyloxiranyl)phenyl-‐2-‐
methylbutyrate*
0.3,
trans-‐isoosmorhizole
0.1
epoxypseudoisoeugenyl
2-‐methylbutyrate
67,
4-‐(3-‐methyloxiranyl)phenyl-‐2-‐
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2005
Tabanca
et
al.,
2005
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
13
P.
tragium
ssp.
Fruit
lithophila
0.73
Stem+Leaf
0.22
Root
0.17
P.
tragium
subsp.
Fruit
polyclada
0.92
Stem+Leaf
0.10
Root
0.22
P.
tragium
subsp.
Fruit
pseudotragium
1.87
*New
compunds
Stem+Leaf
0.08
Root
0.11
methylbutyrate*
4,
4-‐(1-‐prop-‐(1E)-‐
enyl)phenyl
(2S)-‐methylbutyrate
3.3,
dictamnol
0.2
β-‐bisabolene
30,
geijerene
23,
epoxypseudoisoeugenyl
2-‐methylbutyrate
2.5,
traginone*
1,
4-‐(1-‐prop-‐(1E)-‐enyl)phenyl
(2S)-‐methylbutyrate
0.2,
aureane
0.1*
geijerene
32,
pregeijerene
8,
dictamnol
6,
traginone*
5,
epoxypseudoisoeugenyl
2-‐
methylbutyrate
4,
4,6-‐guaiadiene
0.3,
aureane*
0.2
geijerene
27,
4,10-‐dihydro-‐1,4-‐
dimethylazulene
14,
4,6-‐guaiadiene
7,
traginone*
1,
aureane*
0.2
(Z)-‐β-‐farnesene
57,
epoxypseudoisoeugenyl
2-‐methylbutyrate
20,
4-‐methoxy-‐2-‐[(2R,3R)-‐
3-‐methyloxiranyl]phenyl
tiglate
6,
4-‐
methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylangelate
0.5
(Z)-‐β-‐farnesene
23,
epoxypseudoisoeugenyl
2-‐methylbutyrate22,
α-‐pinene
12,
4-‐
methoxy-‐2-‐[(2R,3R)-‐3-‐methyloxiranyl]phenyl
tiglate
5,
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylangelate
1.5,
4-‐Methoxy-‐2-‐(prop
(1E)-‐
enyl)phenyl
tiglate
0.5
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylangelate
40,
epoxypseudoisoeugenyl
2-‐methylbutyrate
16,
4-‐methoxy-‐2-‐[(2R,3R)-‐
3-‐methyloxiranyl]phenyl
tiglate
12,
4-‐
Methoxy-‐2-‐(prop
(1E)-‐enyl)phenyl
tiglate
0.4
β-‐bisabolene
19,
α-‐pinene
16,
epoxypseudoisoeugenyl-‐2-‐methylbutyrate
10,
α-‐zingiberene
8,
4-‐(prop-‐(1E)-‐
enyl)phenyl
tiglate
0.8,
4-‐methoxy-‐2-‐(3-‐
methyloxiranyl)-‐phenylangelate
0.8,
trans-‐
isoosmorhizole
0.6,
4-‐(1-‐prop-‐(1E)-‐
enyl)phenyl
(2S)-‐methylbutyrate
0.2
α-‐pinene
31,
β-‐bisabolene
6,
epoxypseudoisoeugenyl
2-‐methylbutyrate
6,
4-‐(prop-‐(1E)-‐enyl)phenyl
tiglate
0.4,
trans-‐
isoosmorhizole
0.3,
4-‐(1-‐prop-‐(1E)-‐
enyl)phenyl
(2S)-‐methylbutyrate
0.2,
4-‐
methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylangelate
0.2
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐
phenylangelate
31,
epoxypseudoisoeugenyl-‐
2-‐methylbutyrate
19,
traginone*
1,
trans-‐
isoosmorhizole
0.8,
dictamnol
0.6,
4-‐(prop-‐
(1E)-‐enyl)phenyl
tiglate
0.5
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
Tabanca
et
al.,
2006
14
SCALIGERIA
OILS
Scaligeria
is
represented
in
Turkey
by
seven
species
of
which
two
are
endemic.
Scaligeria
lazica
is
an
endemic
species.
Herbaal
parts
of
this
species
has
a
strong
smell
of
aniseeds
due
to
the
presence
of
trans-‐anethole
in
its
oil.
Fruit
oil
of
the
same
species
was
found
as
a
rich
source
of
(Z)-‐b-‐Farnesene.
After
removal
of
the
oil,
aqueous
distillate
of
the
Herba
was
extracted
with
hexane.
It
contained
phenolic
aldehydes
as
main
constituents
(Baser
et
al.,
1993;
1995).
Scaligeria
tripartita
fruit
oil
was
rich
in
geijerenes
and
its
root
oil
contained
epoxypseudoisoeugenylangelate
and
geijerene
(Tabanca,
et
al.,
2007).
Chemical
proximity
of
Pimpinella
and
Scaligeria
species
is
striking.
Table
9.
Scaligeria
oils
of
Turkey
Plant
name
Part
%
yield
Main
components
(%)
Ref.
Scaligeria
lazica
(E)
Herba
0.7
trans-‐anethole
(50)
Baser
et
al.,
1993.
Fruit
2.2
(Z)-‐β-‐farnesene
89
Baser
et
al.,
1995.
Scaligeria
tripartita
Aqueous
distillate
of
the
Herba
extracted
with
hexane
2-‐hydroxy-‐5-‐
Baser
et
al.,
1993.
methoxybenzaldehyde
22,
phenylacetaldehyde
14
Stem
tr
Fruit
2.24
geijerene
37,
(Z)-‐β-‐
farnesene
9,
β-‐bisabolene
9,
dictamnol
9,
lavandulyl
acetate
9,
pregeijerene
5,
geijerene
isomer
5
geijerene
55,
geijerene
isomer
12,
β-‐bisabolene
7,
pregeijerene
6,
dictamnol
5
Tabanca,
2007.
et
al.,
Tabanca,
2007.
et
al.,
ECHINOPHORA
OILS
Herbaal
parts
of
all
six
species
growing
in
Turkey
have
been
studied.
Fresh
and
dried
leaves
of
Echinophora
tenuifolia
L.
ssp.
sibthorpiana
(Guss.)
Tutin
which
is
known
as
“Çörtük,
Turşu
otu
or
Tarhana
otu”
in
Turkish
are
added
to
meaty
meals,
pickles
and
soups
for
flavouring.
According
to
previous
as
well
as
our
studies,
the
oil
of
this
species
is
characterised
with
a
high
percentage
of
methyl
eugenol
(18-‐59%)
(Baser,
et
al.,
1994).
α-‐Phellandrene
is
another
important
compound
also
for
the
two
endemic
species
E.
chrysantha
Freyn
et
Sint.
(Baser
et
al.,
1996a;
Baser
et
al.,
1998f)
and
E.
lamondiana
(Baser
et
al.,
2000a).
The
latter
is
a
recently
described
new
species
of
Echinophora
(Yıldız
&
Bahcecioglu,
1997).
Main
constituent
of
its
oil
was
δ-‐3-‐carene
(48%).
The
oil
of
E.
orientalis
revealed
the
occurrence
of
monoterpene
hydrocarbons
as
main
constituents.
E.
trichophylla
J.E.Smith,
endemic
in
Turkey,
yielded
1.4%
oil
with
sabinene
(27%),
terpinen-‐4-‐ol
(16%)
and
(E,E)-‐cosmene
(14%)
as
main
constituents.
Cosmene
(2,6-‐dimethyl-‐1,3(E),5(E),7-‐octatetraene)
was
previously
reported
as
a
constituent
of
Cosmos
bipinnatus
Cav.
several
other
Compositae
plants
and
Echinophora
spinosa,
an
European
species
(Kubeczka,
1988).
This
compound
(2.1%)
was
also
found
in
the
oil
of
E.
orientalis
Hedge
et
Lamond
which
contained
myrcene
(34%)
and
p-‐cymene
(19%)
as
main
constituents.
(E,Z)-‐
15
isomer
of
cosmene
was
found
in
the
oil
of
E.
trichophylla
(Baser
et
al.,
1998f).
Oil
poor
species
E.
tournefortii
Jaub.
et
Spach.
and
E.
carvifolia
Boiss.
et
Bal.
(E)
yielded
oils
rich
in
sesquiterpenes
and
the
status
of
the
latter
has
been
transformed
to
the
genus
Thecocarpus
as
T.
carvifolius
(Duran,
2014)
(Table
10).
Table
10.
Echinophora
oils
of
Turkey
Plant
name
E.
carvifolia
(E)
Thecocarpus
carvifolius
E.
chrysantha
(E)
Part
Herba
%
yield
tr
Herba
0.65
E.
lamondiana
(E)
Herba
1.6
E.
orientalis
Herba
0.5
E.
tenuifolia
1.6
E.
tenuifolia
subsp.
sibthorpiana
Herba
1.0-‐1.7
Herba
0.76-‐2.4
Leaf
0.77
E.
trichophylla
(E)
Herba
1.4
E.
tournefortii
Herba
0.2
Herba
0.18
Main
components
(%)
germacrene
D
31,
β-‐caryophyllene
5
Ref.
Baser
et
al.,
1998f
α-‐phellandrene
48-‐61,
β-‐phellandrene
7-‐8
Baser
et
al.,
1996a
Baser
et
al.,
1998f
δ-‐3-‐carene
48,
α-‐phellandrene
28,
p-‐ Baser
et
al.,
2000a
cymene
7
myrcene
34,
p-‐cymene
19,
(E,E)-‐cosmene
Baser
et
al.,
2
1998f
α-‐phellandrene
46,
eugenol
30,
p-‐cymene
Aridogan
et
24
al.,
2002
methy
leugenol
18-‐59,
α-‐phellandrene
16-‐ Baser
et
al.,
52,
p-‐cymene
11-‐15
1998f
Baser
et
al.,
1994
methyl
eugenol
10-‐81,
γ-‐3-‐carene
2-‐63,
α-‐
Chalchat
et
phellandrene
11-‐30,
p-‐cymene
tr-‐10,
β-‐ al.,
2007
Ozcan
et
al.,
phellandrene
3-‐5
2002
Ozcan
&
Akgul,
2003
Gokbulut
et
δ-‐3-‐carene
18,
methyl
eugenol
16,
α-‐
al.,
2013
phellandrene
9,
p-‐cymene
9
sabinene
27,
terpinen-‐4-‐ol
16,
2,6-‐
Baser
et
al.,
dimethyl-‐1,3(E),5(E),7-‐octatetraene
[(E,E)-‐ 1998f
cosmene]
14
caryophyllene
oxide
13,
α-‐pinene
10
Baser
et
al.,
1998f
myrcene
30,
α-‐pinene
27
Demirci,
B.,
et
al.,
2010a
FERULA
OILS
Ferula
is
represented
in
the
world
by
around
185
species.
According
to
latest
counts,
Ferula
taxa
in
Turkey
numbers
24
with
23
species,
14
being
endemic
(Kurtoglu
et
al.,
2013;
Pimenov
&
Kljuykov,
2013;
Duran,
2014).
17
taxa
have
been
studied
for
their
essential
oils
(Table
11)
Fruit
oil
yields
varied
between
trace
and
3.8%.
High
oil
yielding
species
were
as
follows:
F.
drudeana
3.7-‐3.8%,
F.
elaeochytris
0.3-‐3.5%,
F.
duranii
2.6%,
F.
coskunii
2%,
F.
mervynii
2%,
F.
parva
2%,
F.
brevipedicellata
1.87%,
F.
hermonis
0.4-‐1.75%.
16
Fruit
oils
of
most
Ferula
species
are
characterized
by
the
high
content
of
monoterpenes,
especially
α-‐
pinene
[F.
mervynii
80%,
F.
elaeochytris
13-‐73%,
F.
hermonis
72%,
F.
lycia
15-‐69%,
F.
brevipedicellata
65%,
F.
communis
60%,
F.
rigidula
13-‐60%,
F.
coskunii
37%,
F.
tingitana
5-‐36%,
F.
parva
34%,
F.
haussknechtii
32%];
β-‐phellandrene
F.
halophila
14-‐72%,
F.
orientalis
24%
(Herba)].
Sesquiterpenes
are
main
constituents
in
the
fruit
oils
of
F.
anatolica
(germacrene
D
30%),
F.
duranii
(germacrene
D
25%),
F.
szowitsiana
[β
and
α-‐eudesmol
32+18
%
(leaf);
30+17%
(stem)],
F.
drudeana
(shyobunone
+
epishyobunone
+
diepishyobunone
67%).
Fruit
oil
of
F.
szowitsiana
was
rich
in
naphthalene
(28%)
and
an
unknown
constituent
(7%).
Naphthalene
was
also
encountered
in
a
number
of
Ferula
oils.
F.
drudeana
and
F.
szowitsiana
stand
out
by
their
different
chemical
composition
of
their
oils
among
the
Ferula
species
studied
so
far.
Table
11.
Ferula
oils
Plant
name
F.
anatolica
(E)
Part
Fruit
%
yield
tr
F.
brevipedicellata
(E)
Fruit
1.87
F.
communis
Fruit
0.09
Main
components
%
germacrene
D
30,
naphthalene
22,
germacrene
D-‐4-‐ol
4,
δ-‐cadinene
3
α-‐pinene
65,
β-‐phellandrene
7,
β-‐pinene
7,
naphthalene
4
α-‐pinene
60,
β-‐pinene
17,
naphthalene
4
F.
coskunii
(E)
Fruit
2.0
sabinene
38,
α-‐pinene
37,
β-‐pinene
11
F.
drudeana
(E)
Fruit
3.7
Fruit
3.8
F.
duranii
(E)
Fruit
2.6
F.
elaeochytris
Fruit
0.27
6-‐epi-‐isoshyobunone
38,
shyobunone
25,
diepishyobunone
6
shyobunone
44,
6-‐epi-‐isoshyobunone
13,
epi-‐shyobunone
10,
β-‐pinene
6
germacrene
D
25,
naphthalene
10,
α-‐
copaene
6
nonane
27,
α-‐pinene
13,
germacrene
B
10
Fruit
3.5
α-‐pinene
73,
β-‐pinene
15
Fruit
0.35
β-‐phellandrene
14,
eremophilene
9
Fruit
0.62
β-‐phellandrene
38,
eremophilene
7
cFr.
1.3
β-‐phellandrene
72,
eremophilene
5
F.
haussknechtii
Fruit
0.88
F.
hermonis
Fruit
F.
lycia
(E)
Herba
F.
halophila
(E)
α-‐pinene
32,
camphene
31,
myrcene
7,
bornyl
acetate
7,
β-‐pinene
5
0.41-‐1.75
α-‐pinene
72
α-‐pinene
60,
β-‐pinene
19,
limonene
3,
bornyl
acetate
2
Ref.
Baser
et
al.,
2007a
Baser
et
al.,
2007a
Baser
et
al.,
2007a
Baser
et
al.,
2007a
Baser
et
al.,
2007a
Miski
et
al.,
2012
Baser
et
al.,
2007a
Baser
et
al.,
2000c
Baser
et
al.,
2007a
Baser
et
al.,
2007a
Miski
et
al.,
2013b
Miski
et
al.,
2013b
Baser
et
al.,
2007a
Baser
et
al.,
2007a
Kose
et
al.,
2010
17
Fruit
F.
mervynii
(E)
Fruit
F.
orientalis
Herba
F.
parva
(E)
Fruit
F.
rigidula
Fruit
cFr.
F.
szowitsiana
Fruit
Leaf
Stem
F.
tingitana
Fruit
0.58-‐1.35
1)
naphthalene
27,
α-‐pinene
26,
β-‐pinene
Baser
et
al.,
26,
caryophyllene
oxide
5
2007a
2)
naphthalene
17,
α-‐pinene
15,
caryophyllene
oxide
11,
germacrene
B
4
3)
α-‐pinene
69,
β-‐pinene
4
4)
α-‐pinene
67,
β-‐phellandrene
5,
β-‐
caryophyllene
5,
β-‐pinene
3
5)
α-‐pinene
60,
caryophyllene
oxide
3,
β-‐
pinene
3,
naphthalene
3
2
α-‐pinene
80,
sabinene
12,
β-‐pinene
9
Baser
et
al.,
2007a
0.51
β-‐phellandrene
24,
(E)-‐β-‐ocimene
14,
α-‐ Kartal
et
al.,
pinene
13,
α-‐phellandrene
12,
2007
dehydrosesquicineole
10
2
α-‐pinene
34,
eremophilene
9,
Baser
et
al.,
naphthalene
5
2007a
1)
camphene
15,
α-‐pinene
13,
δ-‐cadinene
Baser
et
al.,
2007a
13,
α-‐cadinol
10,
germacrene
D-‐4-‐ol
10
2)
α-‐pinene
60,
tricyclene
8,
β-‐pinene
4,
eremophilene
3
3)
α-‐pinene
68,
tricyclene
9,
β-‐pinene
4
0.8
α-‐pinene
24,
camphene
20,
germacrene
Miski
et
al.,
2013a
D-‐4-‐ol
8,
δ-‐cadinene
6,
α-‐cadinol
5
naphthalene
28,
unknown
9,α-‐pinene
7,
Baser
et
al.,
β-‐pinene
4,
α-‐copaene
4,
sabinene
4
2007a
0.40
β-‐eudesmol
32,
α-‐eudesmol
18,
α-‐pinene
Ozek,
G.,
et
9
al.,
2008
0.05
β-‐eudesmol
30,
α-‐eudesmol
17,
α-‐pinene
Ozek,
G.,
et
6
al.,
2008
1)
naphthalene
15,
α-‐pinene
11,
unknown
Baser
et
al.,
7,
daucene
6,
(Z)-‐β-‐farnesene
5,
β-‐pinene
2007a
5
2)
α-‐pinene
36,
β-‐pinene
14,
naphthalene
14,
germacrene
D
5,
(Z)-‐β-‐farnesene
4,
daucene
3
cFr:
Crushed
fruit;
FERULAGO
OILS
Ferulago
is
represented
by
35
taxa
including
34
species
19
of
which
are
endemic
in
the
flora
of
Turkey
(Davis
et
al.,1988;
Duran
2014).
19
of
them
including
12
endemics
were
investigated
by
our
group.
The
results
of
essential
oil
analyses
are
tabulated
in
Table
7.
Percentage
oil
yields
from
some
Ferulago
fruits
are
quite
high:
F.
isaurica
12%,
F.
trachycarpa
7.3%,
F.
asparagifolia
7%,
F.
longistylis
6.4%,
F.
syriaca
4.8%,
F.
thirkeana
4.1%,
F.
humilis
3.9%,
F.
sandrasica
3.9%,
F.
pachyloba
1.5%.
Due
to
paucity
of
study
materials,
some
species
were
subjected
to
microdistillation.
2,3,6-‐trimethylbenzaldehyde
was
the
main
constituent
in
the
fruit
oils
of
F.
asparagifolia
39-‐42%,
F.
platycarpa
30%,
F.
longistylis
29%,
F.
idaea
14%,
F.
syriaca
9%,
F.
setifolia
6%.
In
the
oil
of
F.
setifolia
2,3,5-‐trimethylbenzaldehyde
78%
was
the
main
constituent.
Herbal
parts
of
F.
longistylis
contained
2,3,6-‐trimethylbenzaldehyde
33%
in
the
oil.
p-‐Cymene
and
its
2,3-‐dimethoxy
derivative
were
main
constituents
of
the
fruit
oils
of
F.
sylvatica
(86%),
F.
confusa
(87%),
F.
humilis
(E)
(92%)
and
F.
idaea
(E)
18
(31%).
Carvacrol
methylether,
on
the
other
hand,
was
the
main
constituent
of
the
fruit
oil
of
F.
macrosciadia
(E)
together
with
p-‐cymene.
They
were
also
among
the
main
constituents
is
the
oil
of
F.
idaea
(E).
trans-‐Chrysanthenylacetate
was
the
main
constituent
of
the
fruit
oils
of
F.
galbanifera
17%
and
F.
silaifolia
(E)
84%.
Oils
of
F.
sandrasica
5-‐12%
and
F.
humilis
12%
also
contained
it.
(Z)-‐β-‐ocimene
was
found
as
main
constituent
in
the
fruit
oil
of
F.
trachycarpa
31%,
F.
pachyloba
26%,
F.
sandrasica
(E)
41%,
F.
longistylis
16%
and
another
sample
of
F.
humilis
32%.
A
second
sample
of
F.
sandrasica
fruits
yielded
an
oil
rich
in
α-‐pinene
and
sesquiterpenoids
like
the
fruit
oils
of
F.
aucheri
(E)
and
F.
mughlae
(E).
While
herb
oil
of
F.
trachycarpa
contained
(Z)-‐β-‐ocimene
as
main
constituent
like
its
fruit,
acyclic
aldehydes
were
constituents
of
the
root
oil
(Baser
et
al.,
1998a).
Table
12.
Ferulago
oils
of
Turkey
Plant
name
Part
%
F.
asparagifolia
Fruit
7.0
dist
n
WD
MD
MD
MD
F.
aucheri
(E)
Fruit
F.
confusa
Fruit
MD
F.
galbanifera
Fruit
MD
1.3
WD
MD
MD
3.9
WD
F.
humilis
(E)
Fruit
F.
idaea
(E)
Fruit
MD
F.
isaurica
(E)
Fruit
12
WD
Herb
0.08
WD
Root
0.7
WD
Main
components
(%)
2,3,6-‐trimethylbenzaldehyde
39,
myrcene
18
Ref.
Baser
et
al.,
2001
Demirci,
F.,
et
al.,
2000
2,3,6-‐trimethylbenzaldehyde
42,
α-‐
Baser
et
al.,
pinene
11
2002a
α-‐pinene
21,
caryophyllene
oxide
8,
Baser
et
al.,
spathulenol
7
2002a
α-‐pinene
36,
humulene
epoxide
II
7,
Baser
et
al.,
trans-‐verbenol
6
2002a
2,5-‐dimethoxy
p-‐cymene
63,
p-‐cymene
Kurkcuoglu
et
24
al.,
2010
trans-‐chrysanthenyl
acetate
17,
p-‐
Baser
et
al.,
cymene
12,
α-‐phellandrene
11,
limonene
2002a
10
α-‐pinene
32,
sabinene
16,
limonene
7,
α-‐ Demirci,
F.,
et
phellandrene
6
al.,
2000
(Z)-‐β-‐ocimene
32,
limonene
31
Baser
et
al.,
2002a
2,5-‐dimethoxy
p-‐cymene
76,
p-‐cymene
Baser,
2002
16
(Z)-‐β-‐ocimene
32,
limonene
17,
α-‐pinene
Demirci,
F.,
et
12,
trans-‐chrysanthenyl
acetate
12
al.,
2000
p-‐cymene
18,
α-‐pinene
16,
2,3,6-‐
Baser
et
al.,
trimethylbenzaldehyde
14,
carvacrol
2002a
methylether
13,
2,5-‐dimethoxy
p-‐
cymene
13
α-‐pinene
32,
limonene
24,
myrcene
17
Erdurak
et
al.,
2006
nonacosane
26,
hexadecanoic
acid
15
Kilic
et
al.,
2010a
terpinolene
42,
myrcene
27
Erdurak
et
al.,
2006
19
F.
longistylis
(E)
Fruit
6.4
WD
Herb
0.16
WD
F.
macrosciadia
(E)
Fruit
MD
F.
mughlae
(E)
Fruit
MD
F.
pachyloba
(E)
Herba
1.5
WD
F.
platycarpa
(E)
Herba
0.07
WD
F.
sandrasica
(E)
Fruit
3.9
WD
MD
F.
setifolia
Herba
0.6
0.26
WD
WD
F.
silaifolia
(E)
Fruit
MD
F.
sylvatica
Fruit
MD
F.
syriaca
Fruit
4.8
WD
Root
1.1
WD
Fruit
4.1
WD
MD
Fruit
7.3
WD
Herba
0.6
WD
Root
Fruit
0.02
WD
MD
F.
thirkeana
(E)
F.
trachycarpa
*
New
compounds
2,3,6-‐trimethylbenzaldehyde
29,
α-‐
pinene
17,
(Z)-‐β-‐ocimene
16,
sabinene
6,
myrcene
6,
bornyl
acetate
4
2,3,6-‐trimethylbenzaldehyde
33,
bornyl
acetate
13
carvacrol
methylether
72-‐78,
p-‐cymene
19-‐38
α-‐pinene
25,
cubenol
13,
β-‐phellandrene
6
(Z)-‐β-‐ocimene
26,
α-‐pinene
10
Ozkan
et
al.,
2008
Kilic
et
a.,l
2010a
Baser
et
al.,
2002a
Baser
et
al.,
2002a
Kilic
et
al.,
2010a
2,3,6-‐trimethylbenzaldehyde
30,
cis-‐
Kilic
et
al.,
chrysanthenylacetate
24
2010a
(Z)-‐β-‐ocimene
32,
limonene
17,
α-‐pinene
Baser,
2002
12,
trans-‐chrysanthenyl
acetate
12
α-‐pinene
41,
germacrene
D
8,
α-‐
Baser
et
al.,
humulene
6,
trans-‐chrysanthenyl
acetate
2002a
5
ocimene
31,
δ-‐3-‐carene
27,
α-‐pinene
18
Celik
et
al.,
2013
2,4,5-‐trimethylbenzaldehyde
78,
2,3,6-‐
Baser
et
al.,
trimethylbenzaldehyde
6
2002a
trans-‐chrysanthenyl
acetate
84,
α-‐pinene
Baser
et
al.,
6
2002a
p-‐cymene
46,
2,5-‐dimethoxy
p-‐cymene
Baser
et
al.,
40
2002a
myrcene
15,
terpinolene
13,
4,6-‐
Erdurak
et
al.,
guaiadiene
11,
cubenol
9,
2,3,6-‐
2006
trimethylbenzaldehyde
9
bornyl
acetate
69,
terpinolene
13
Erdurak
et
al.,
2006
ferulagone
64*,
germacrene
D
14,
α-‐
Baser
et
al.,
pinene
9
2002a
ferulagone
56*,
germacrene
D
13,
α-‐
Baser
et
al.,
pinene
10
2002a
(Z)-‐β-‐ocimene
31,
myrcene
28
Baser
et
al.,
1998b
(Z)-‐β-‐ocimene
34,
α-‐pinene
8
Demirci,
F.,
et
al.,
2000
octanal
10,
(E)-‐2-‐decenal
7
Baser,
2002
Baser
et
al.,
γ-‐terpinene
28,
p-‐cymene
22,
myrcene
2002a
20
HERACLEUM
OILS
Heracleum
is
represented
in
Turkey
by
21
taxa
comprising
17
species
including
7
endemics.
Essential
oil
compositions
of
the
fruits
of
five
species
have
been
investigated.
Heracleum
fruits
are
characterised
with
high
oil
yield
and
high
proportion
of
aliphatic
esters
in
their
oils.
Octyl
acetate
was
the
main
constituent
in
the
oils
of
H.
crenatifolium
(19-‐95%),
H.
platytaenium
(73-‐88%),
H.
paphlagonicum
(27-‐
95%).
Hexyl
butyrate
was
the
main
compound
in
the
oil
of
H.
argaeum
(39%).
Octyl
butyrate
and
20
octanol
were
the
main
constituents
of
the
oils
of
H.
sphondylium
subsp.
ternatum
(25-‐43%
and
39-‐
50%,
resp.)
Table
13.
Heracleum
oils
of
Turkey
Plant
name
Part
H.
argaeum
(E)
Fruit
H.
crenatifolium
(E)
%
yield
1.24
Fruit
3.66
Fruit
5.5
H.
paphlagonicum
(E)
Fruit
4.9-‐7.4
H.
platytaenium
(E)
Fruit
5.2-‐6.8
Fruit
5.33
Herba
Fruit
3.7
Fruit
MD
Fruit
2.0
H.
sphondylium
subsp.
ternatum
Main
components
(%)
Ref.
hexyl
butyrate
39,
octyl
hexanoate
9,
Baser
et
al.,
octyl
acetate
7,
octylbutyrate
6
1998c
octyl
acetate
19-‐95,
octanol
1-‐5,
Ozek,
T.,
et
al.,
octyl
isovalerate
1-‐6,
decyl
acetate
1-‐ 2005
4
Iscan
et
al.,
2004
octyl
acetate
88,
octanol
3,
(Z)-‐4
Tosun
et
al.,
octenyl
acetate
1
2008
octyl
acetate
27-‐95,
hexyl
butyrate
Baser
et
al.,
17-‐25
2000e
octyl
acetate
73-‐77,
octyl
butyrate
Kurkcuoglu
et
12-‐17
al.,
1995
octyl
acetate
88,
octyl
hexanoate
3-‐ Ozek,
T.,
et
al.,
5,
(Z)-‐4-‐octenyl
acetate
2,
octanol
1,
2005
decanal
1
Iscan
et
al.,
2004
octyl
acetate
86,
octyl
hexanoate
13,
Akcin
et
al.,
(Z)-‐4-‐octyl
acetate
2,
octyl
octanoate
2013
1
octanol
39-‐50,
octyl
butyrate
25-‐27,
Ozek,
T.,
et
al.,
octyl
acetate
7-‐11
2002
Iscan
et
al.,
2003
octyl
butyrate
43,
octyl
acetate
31,
Ozek,
T.,
et
al.,
octanol
9
2002
octyl
butyrate
35-‐41,
apiole
5-‐20,
(Z)-‐ Ozek,T.,
et
al.,
4-‐octenyl
acetate
2-‐4,
(Z)-‐4-‐octenyl
2005
butyrate
3
Iscan
et
al.,
2004
Fruits
of
Zosima
absinthifolia
(Baser
et
al.,
2000c)
and
Malabaila
secacul
(Demirci,
B.,
et
al.,
2006)
yielded
oils
also
rich
in
aliphatic
esters.
The
former
which
is
the
only
Zosima
species
recorded
in
Turkey
is
a
close
relative
of
the
genus
Heracleum
and
contains
octanol
esters
as
main
constituents.
Likewise,
Pastinaca
sativa
subsp.
urens
fruit
oil
also
contained
octanol
esters
as
main
constituents
(Kurkcuoglu
et
al.,
2006a).
Pastinaca
is
represented
in
Turkey
by
4
taxa
including
3
species
comprising
one
endemic.
Main
constituents
of
the
Malabaila
oil
were
hexanol
esters.
Malabaila
is
represented
in
the
flora
of
Turkey
by
six
species.
21
Table
14.
Zosima,
Pastinaca
and
Malabaila
oils
of
Turkey
Plant
name
Zosima
absinthifolia
Part
Fruit
%
yield
0.9
Pastinaca
sativa
subsp.
urens
Fruit
2.5
Malabaila
secacul
Fruit
1.05
Main
components
(%)
octyl
acetate
38,
octyl
hexanoate
32
Ref.
Baser
et
al.,
2000c
octyl
butyrate
80,
octyl
hexanoate
5,
Kurkcuoglu
et
al.,
phenylethyl
butyrate
2
2006a
hexyl
hexanoate
73,
hexyl
octanoate
Demirci,
B.,
et
al.,
9
2006
TORDYLIUM
OILS
Tordylium
is
represented
in
Turkey
by
17
species,
nine
being
endemic.
Fruit
oils
of
nine
species
have
been
investigated.
Except
for
T.
aegyptiacum
in
which
hexadecanoic
acid
(40%)
was
the
main
component,
oils
of
all
the
other
species
investigated
contained
octanol
esters
as
main
constituents
like
in
the
case
of
Heracleum
oils.
Octyl
hexanoate
predominated
the
oils
of
T.
apulum
(44%),
T.
hasselquistiae
(73%),
T.
lanatum
(E)
(59%),
T.
pestalozzae
(E)
(56%),
T.
pustulosum
(E)
(73%),
T.
syriacum
(46-‐81%),
while
octyl
octanoate
was
a
major
constituent
in
the
oils
of
T.
ketenoglui
(E)
(73%),
T.
trachycarpum
(80%),
T.
apulum
(35%).
Table
15.
Tordylium
oils
of
Turkey
Plant
name
Part
yield
%
T.
aegyptiacum
Fruit
<0.1
T.
apulum
Fruit
MD
T.
hasselquistiae
Fruit
0.5
T.
ketenoglui
(E)
Fruit
0.3
T.
lanatum
(E)
Fruit
0.15
T.
pestalozzae
(E)
T.
pustulosum
(E)
Fruit
0.3
Fruit
MD
Fruit
3.3
T.
syriacum
Fruit
0.1-‐0.7
T.
trachycarpum
Fruit
1.85
Main
component
%
Ref.
hexadecanoic
acid
40,
β-‐caryophyllene
11,
octyl
octanoate
9,
caryophyllene
oxide
9
octyl
hexanoate
44,
octyl
octanoate
35,
octanol
17
octyl
hexanoate
73,
octyl
octanoate
13,
octanol
3
octyl
octanoate
29,
octanol
12,
bornyl
acetate
7
octyl
hexanoate
59,
octanol
22
Tosun
et
al.,
2010
Baser
et
al.,
2002b
Ozek,
T.,
et
al.,
2007a
Tosun
et
al.,
2007
octyl
hexanoate
56,
octyl
octanoate
16,
octanol
15,
hexadecanoic
acid
6
octyl
hexanoate
73,
octanol
10
octyl
hexanoate
69,
octyl
2-‐methylbutyrate
18,
octanol
4
octyl
hexanoate
46-‐81,
octanol
1-‐8,
α-‐humulene
2-‐7,
2,3,4-‐trimethylbenzaldehyde
1-‐5
octyl
octanoate
80,
octanol
11,
octanoic
acid
3
Tosun
et
al.,
2006b
Tosun
et
al.,
2006b
Baser
et
al.,
2002b
Tosun
et
al.,
2006b
Kurkcuoglu
et
al.,
2012
Ozek,
T.,
et
al.,
2007a
22
SMYRNIUM
OILS
Seven
Smyrnium
species
are
recorded
in
the
flora
of
Turkey.
Three
of
them
have
been
investigated
for
essential
oils.
The
results
are
summarised
in
Table
16.
Root
oils
of
S.
olusatrum
and
S.
perfoliatum
were
investigated
by
our
group
(Baser,
2002).
Furanosesquiterpenes
are
characteristic
constituents
of
Smyrnium
oils.
Isofuranogermacrene
was
found
as
main
constituent
in
the
root
oils
of
S.
olusatrum
and
S.
perfoliatum
and
the
fruit
oil
of
S.
rotundifolium.
Furanodiene
was
a
major
constituent
in
the
root
and
fruit
oils
of
S.
perfoliatum
and
fruit
oil
of
S.
rotundifolium.
Fruit
oils
of
S.
perfoliatum
from
two
different
locations
yielded
germacrene
D
and
α-‐selinene
as
main
constituents,
respectively.
The
former
also
contained
acetoxy-‐
furanoeudesmenes
(Kubeczka
&
Molleken,
1999;
Molleken
et
al.,
1998).
Table
16.
Smyrnium
oils
of
Turkey
Plant
name
Part
%
yield
S.
olusatrum
Root
S.
perfoliatum
S.
rotundifolium
Fruit
0.7
Fruit
0.2
Root
Fruit
Main
components
(%)
isofuranogermacrene
51
Ref.
Baser,
2002
germacrene
D
45-‐47,
1β-‐acetoxyfuranoeudesm-‐3-‐ene
9
α-‐selinene
31,
furanodiene
20,
germacrene
D
9
Kubeczka
&
Molleken,
1999;
Molleken
et
al.,
1998
Baser,
2002
isofuranogermacrene
48,
isofuranogermacrene
35-‐45,
furanodiene
28-‐39
Kubeczka
&
Molleken,
1999
PRANGOS
OILS
The
genus
Prangos
is
represented
by
19
taxa
including
19
species
in
the
flora
of
Turkey
and
ten
of
them
are
endemic.
Essential
oils
of
nine
species
were
subjected
to
analysis.
Results
are
listed
in
Table
17.
The
endemic
P.
denticulata
root
yielded
3.2%
oil.
P.
platychlaena
(E)
and
P.
euchtritzii
(E)
fruits
yielded
1.4-‐2.7%
and
0.7-‐2.1%
oils,
resp.
Oil
yields
of
the
other
species
investigated
gave
<1%
essential
oil.
P.
denticulata
(E),
P.
ferulacea,
P.
ilanae,
P.
platychlaena
(E)
and
P.
uechtritzii
(E)
oils
were
rich
in
monoterpenes
while
P.
heyniae
(E),
P.
pabularia,
P.
turcica
(E)
and
P.
sp.
nova
(E)
oils
were
predominated
by
sesquiterpenes.
The
oil
from
intact
and
crushed
fruits
of
P.
ferulacea
contained
the
same
monoterpene
hydrocarbons
as
major
components
with
γ-‐terpinene
as
the
main
constituent.
However,
the
distilled
oil
from
fruits
crushed
after
distillation
contained
sesquiterpenes,
germacrene
B
and
germacrene
D
as
main
constituents
together
with
γ-‐terpinene
(Baser
et
al.,
1996c).
Prangos
heyniae
is
a
recently
described
species
(Duman
&
Watson,
1999).
Oils
from
fruits
collected
from
two
nearly
localities
yielded
β-‐bisabolene
and
its
alcohol
and
aldehyde
(Baser
et
al.,
2000b).
β-‐
Bisabolenal
and
β-‐bisabolenol
were
first
reported
as
constituents
of
Neocallitropis
pancheri
(Carriere)
de
Laubeufels
(Cupressaceae)
(Raharivelomanana
et
al.,
1993).
This
is
the
second
report
on
the
occurrence
of
these
rare
sesquiterpenes
in
nature.
Main
component
in
the
oil
of
P.
uechtritzii
fruits
was
a
new
monoterpene
7-‐epi-‐1,2-‐
dehydrosesquicineole
(13%).
Acetylenic
compound
3,5-‐nonadiyn-‐2-‐ene
and
its
esters
were
among
the
23
main
components
of
the
fruit
oil
of
P.
platychlaena;
and
3,5-‐nonadiyn-‐7-‐ene
in
the
root
oil
of
P.
denticulata.
The
status
of
Prangos
bornmuelleri
has
recently
been
changed
to
a
new
genus,
hence
renamed
as
Ekimia
bornmuelleri
(Duman,
H.
&
Watson,
1999).
Steam
volatiles
of
the
fruits
of
this
species
were
published
(Baser
et
al.,
1999).
The
results
are
summarised
in
Table
28
under
Ekimia
bornmuelleri.
Table
17.
Prangos
oils
of
Turkey
Plant
name
P.
denticulata
(E)
Part
Fruit
Root
Fruit
yield
%
tr
3.2
0.36
cFr
0.97
Frcad
0.98
Herba
P.
heyniae
(E)
Fruit
0.3-‐
0.9
P.
ilanae
Herba
0.2
P.
pabularia
Fruit
0.2
P.
platychlaena
(E)
P.
platychlaena
subsp
platychlaena
(E)
Fruit
Fruit
0.4
1.4-‐2.7
P.
turcica
(E)
Fruit
0.37
P.
uechtritzii
(E)
Fruit
0.76
Fruit
MD
Fruit
2.1
Herba
0.7
Fruit
0.65
P.
ferulacea
P.
sp.
nova
(E)
Main
component
%
sabinene
26,
p-‐cymene
20
δ-‐3-‐carene
49,
(Z)-‐3,5-‐nonadiyn-‐7-‐ene
20
γ-‐terpinene
33,
α-‐pinene
13,
p-‐cymene
11,
(E)-‐β-‐
ocimene
8,
(Z)-‐β-‐ocimene
4
γterpinene
30,
α-‐pinene
18,
p-‐cymene
10,
(E)-‐β-‐
ocimene
8,
(Z)-‐β-‐ocimene
7
germacrene
B
30,
γ-‐terpinene
17,
germacrene
D
8,
α-‐pinene
5,
p-‐cymene
5,
(E)-‐β-‐ocimene
4,
(Z)-‐
β-‐ocimene
4
2,3,6-‐trimethylbenzaldehyde
67,
chrysanthenyl
acetate
15,
p-‐mentha-‐1,5-‐dien-‐8-‐ol
4,
β-‐ocimene
4,
α-‐pinene
3
β-‐bisabolenal
18-‐53,
β-‐bisabolenol
2-‐15,
β-‐
bisabolene
10-‐12,
germacrene
D
3-‐14,
germacrene
B
2-‐
9
α-‐phellandrene
31,
p-‐cymene
19,
β-‐phellandrene
13,
limonene
4,
α-‐pinene
3
α-‐humulene
17,
bicyclogermacrene
16,
spathulenol
11,
germacrene
D
6,
α-‐pinene
4
α-‐pinene
70,
β-‐phellandrene
11
3,5-‐nonadiyn-‐2-‐yl
acetate
11-‐45,
3,5-‐nonadiyne
6-‐25,
3,5-‐nonadiyn-‐2-‐yl
acetate
isomer
4,
β-‐
phellandrene
4-‐23,
α-‐phellandrene
0.1-‐18,
α-‐
pinene
7-‐13
α-‐humulene
11,
germacrene
D
11,
naphthalene
9,
terpinolene
8,
bornyl
acetate
7,
germacrene
D-‐4-‐ol
5,
α-‐pinene
4,
p-‐cymene
4
7-‐epi-‐1,2-‐dehydrosesquicineole
13*,
α-‐pinene
8,
β-‐phellandrene
7,
α-‐bisabolol
5
α-‐pinene
11,
β-‐phellandrene
8,
p-‐cymene
6,
14-‐
hydroxy-‐δ-‐cadinene
5
α-‐pinene
41,
nonene
17,
β-‐phellandrene
8,
δ-‐3-‐
carene
7,
p-‐cymene
5
p-‐cymene
11,
γ-‐terpinene
7,
β-‐phellandrene
8,
α-‐
phellandrene
6,
(Z)-‐β-‐ocimene
5
germacrene
D
50,
α-‐cadinol
9,
δ-‐cadinene
6
Ref.
Kilic
et
al.,
2010b
Kilic
et
al.,
2010b
Baser
et
al.,
1996c
Baser
et
al.,
1996c
Baser
et
al.,
1996c
Sumer
Ercan
et
al.,
2013
Baser
et
al.,
2000b
Kurkcuoglu&Baser
personal
comm.
Ozek,
G.,
et
al.,
2007b
Uzel
et
al.,
2006
Tabanca
et
al.,
2009
Ozek,
G.,
et
al.,
2006a
Baser
et
al.,
2000f
Baser
et
al.,
2000f
Uzel
et
al.,
2006
Ozcan
et
al.,
2000
Duran
and
Duman
personal
comm.
cFr:
Crushed
fruit;
Frcad:
Crushed
after
distillation
of
the
whole
fruit;
MD:
Microdistillation;
*
New
Compound
24
SESELI
OILS
14
taxa
belonging
to
13
species
including
four
endemics
are
recorded
in
the
Flora
of
Turkey,
seven
being
endemic.
Seven
taxa
including
three
endemics
have
been
investigated
for
essential
oils.
Main
constituents
are
listed
in
Table
18.
Oil
yields
over
1%
were
as
follows:
S.
petraeum
(Herb-‐3.4%),
S.
resinosum
(Herb-‐2.3%;
Fruit-‐2.1%),
S.
tortuosum
(Fruit-‐2.2%),
S.
campestre
(Fruit-‐1.5%;
Herb-‐1%).
Three
species
yielded
sesquiterpene-‐rich
oils:
S.
andronakii
(E),
S.
libanotis,
S.
gummiferum
subsp.
corymbosum
(E).
In
the
oils
of
five
species,
monoterpenes
and
sesquiterpenes
were
mixed
major
constituents:
S.
campestre,
S.
gummiferum
subsp.
corymbosum
(E),
S.
petraeum,
S.
resinosum
(E),
S.
tortuosum.
In
the
oils
of
S.
campestre
and
S.
tortuosum,
α-‐pinene
and
(E)-‐sesquilavandulol
were
mixed
major
constituents.
Table
18.
Seseli
oils
of
Turkey
Plant
name
Part
%
yield
Main
components
(%)
Ref.
S.
andronakii
(E)
Fruit
2.1
carotol
53,
germacrene
D
9
Tosun
et
al.,
2006a
S.
campestre
Herba
1.0
α-‐pinene
36,
myrcene
6,
sabinene
6,
Baser
et
al.,
limonene
6,
bornyl
acetate
5
2000d
Fruit
1.5
α-‐pinene
26,
(E)-‐sesquilavandulol
12,
Baser
et
al.,
myrcene
9
2000d
Fruit
1
Herba
0.8
Herba
bicyclogermacrene
12,
germacrene
B
14
Tosun
et
al.,
2005
S.
gummiferum
subsp.
gummiferum
Herba
spathulenol
20
Tosun
et
al.,
2005
S.
libanotis
Herba
β-‐caryophyllene
20,
spathulenol
12,
Ozturk
&
Ercisli,
caryophyllene
oxide
12,
euasarone
11,
2006
δ-‐cadinene
9
S.
petraeum
Herba
3.4
carotol
21,
γ-‐terpinene
11,
sabinene
10,
Tosun
et
al.,
2006a
germacrene
D
8
S.
resinosum
(E)
Herba
2.3
4α-‐hydroxy
germacra-‐1(10)-‐
5-‐diene
30,
Baser,
2002
β-‐pinene
16,
germacrene
D
14
Fruit
2.1
Fruit
2.2
Herba
0.32
β-‐pinene
38,
4α-‐hydroxy
germacra-‐
1(10)-‐
5-‐diene
22,
α-‐pinene
14
(E)-‐sesquilavandulol
37,
sabinene
20,
α-‐
pinene
14,
β-‐phellandrene
8
α-‐pinene
36,
sabinene
19,
(E)-‐
sesquilavandulol
8,
β-‐pinene
7
S.
gummiferum
subsp.
corymbosum
(E)
S.
tortuosum
α-‐pinene
36,
(E)-‐sesquilavandulol
3
Baser
et
al.,
2000d
α-‐pinene
9,
sabinene
7,
β-‐elemene
6,
Baser,
2002
spathulenol
6
Dogan
et
al.,
2006
Dogan
et
al.,
2006
Kaya
et
al.,
2003
25
LASERPITIUM
OILS
There
are
five
species
of
Laserpitium
of
which
two
are
endemic
in
Turkey.
Main
constituents
are
listed
in
Table
19.
Root
oil
of
L.
hispidum
yielded
myristicin
as
the
main
constituent
along
with
monoterpenes.
Herba
oil
of
the
endemic
species
L.
petrophyllum
contained
monoterpene
hydrocarbons
as
main
constituents
(Baser
&
Duman,
1997)
(Table
19).
Table
19.
Laserpitium
oils
of
Turkey
Plant
name
Part
L.
hispidum
Root
L.
petrophyllum
(E)
Herba
%
yield
0.4
1.3
Main
components
(%)
Ref.
myristicin
25,
γ-‐terpinene
Baser,
2002
15,
sabinene
13,
terpinolene
12
α-‐pinene
49,
sabinene
26
Baser
&
Duman,
1997
JOHRENIA
OILS
Johrenia
is
represented
in
the
Flora
of
Turkey
with
7
species
comprising
3
endemics.
Five
of
them
have
been
studied
for
their
essential
oils.
Main
constituents
are
listed
in
Table
20.
Essential
oils
of
the
endemic
species
J.
alpina,
J.
polyscias
and
J.
silenoides
were
rich
in
monoterpenes
while
sesquiterpenes
were
the
predominating
components
in
the
oils
of
J.
dichotoma
and
J.
tortuosa.
Methylfarnesoate,
a
sesquiterpene,
was
present
in
the
fruit
oils
of
J.
tortuosa
(43%),
J.
dichotoma
(17%)
and
J.
silenoides
(9%).
Table
20.
Johrenia
oils
of
Turkey
Plant
name
Part
yield
%
J.
alpina
(E)
Fruit
Herba
0.03
J.
dichotoma
Fruit
0.02
J.
polyscias
(E)
Fruit
0.02
Herba
Fruit
0.1
Herba
Fruit
0.02
Herba
J.
silenoides
(E)
J.
tortuosa
Main
component
%
Ref.
α-‐pinene
39,
β-‐pinene
5
dodecanoic
acid
24,
α-‐pinene
12,
β-‐
bisabolene
6,
β-‐caryophyllene
5,
hexadecanoic
acid
4
methylfarnesoate
17,
bicyclogermacrene
13,
hexadecanoic
acid
7,
β-‐caryophyllene
6,
spathulenol
5,
α-‐pinene
3
α-‐pinene
23,
β-‐pinene
14,
hexadecanoic
acid
9,
bicyclogermacrene
6,
α-‐pinene
19,
β-‐pinene
18,
limonene
7,
spathulenol
6,
hexadecanoic
acid
5
spathulenol
15,
α-‐pinene
34,
β-‐pinene
14,
methylfarnesoate
9,
germacrene
D
5
spathulenol
13,
α-‐pinene
8,
β-‐pinene
5,
p-‐
cymene
4,
limonene
3,
methylfarnesoate
43,
α-‐pinene
7,
β-‐
pinene
5,
β-‐caryophyllene
5,
bicyclogermacrene
5,
hexadecanoic
acid
3
hexadecanoic
acid
9,
unknown
6,
unknown
5,
pentacosane
5,
tetradecanoic
acid
4
Ozek,
T.,
et
al.,
2009
Ozek,
T.,
et
al.,
2009
Ozek,
T.,
et
al.,
2009
Ozek,
T.,
et
al.,
2009
Ozek,
T.,
et
al.,
2009
Ozek,
T.,
et
al.,
2009
Ozek,
T.,
et
al.,
2009
Ozek,
T.,
et
al.,
2009
Ozek,
T.,
et
al.,
2009
26
BUPLEURUM
OILS
Bupleurum
is
represented
in
Turkey
by
49
taxa
comprising
47
species
including
21
endemics.
Flower,
fruit
and
root
essential
oil
of
12
of
them
have
been
analyzed.
Main
constituents
are
listed
in
Table
21.
Bupleurum
is
an
oil
poor
genus
of
Apiaceae.
Alkanes
were
the
predominating
volatiles
in
majority
of
Bupleurum
oils.
Undecane
was
the
main
constituent
in
B.
cappadocicum
(Fruit
50%;
Root
23%),
B.
croceum
(Fruit
13%),
B.
gerardii
(Flower
37%;
Fruit
49%),
B.
intermedium
(Root
63%),
B.
sulphureum
(Flower
14%;
Fruit
20%);
tridecane
in
B.
lycaonicum
(Flower
15%;
Fruit
37%),
B.
rotundifolium
(Root
12%);
pentacosane
in
B.
turcicum
(Root
9%);
hexacosane
in
B.
lancifolium
(Fruit
13%).
Hexadecanoic
acid
was
the
main
constituent
in
the
oil
of
B.
croceum
(Root
35%),
B.
heldreichii
(Root
46%),
B.
lancifolium
(Root
14%),
B.
rotundifolium
(Flower
12%).
Heptanal
was
the
main
constituent
in
the
oils
of
B.
cappadocicum
(Flower
47%),
B.
turcicum
(Flower
33%;
Fruit
24%)
and
hexanal
in
B.
gerardii
(Root
22%).
Methyl
linoleate
was
the
main
constituent
in
the
flower
oil
of
B.
intermedium
(21%).
Monoterpenes
were
present
in
the
oils
of
the
following
species
as
main
constituents:
a-‐pinene
in
B.
falcatum
subsp.
cernuum
(Flower
41%;
Fruit
42%),
B.
rotundifolium
(Flower
9-‐28%;
Fruit
11%),
b-‐
phellandrene
in
B.
rotundifolium
(Flower
7-‐19%).
Sesquiterpenes
were
the
main
constituent
in
the
oils
of
a
number
of
Bupleurum
species.
Germacrene
D
in
B.
croceum
(Flower
13%),
B.
heldreichii
(Flower
and
Fruit
48%
each),
B.
intermedium
(Fruit
26%),
B.
pauciradiatum
(Flower
12-‐46%);
spathulenol
in
B.
lancifolium
(Flower
15%),
B.
lycaonicum
(Root
14%);
β-‐caryophyllene
in
B.
pauciradiatum
(Flower
10-‐12%);
calarene
in
B.
sulphureum
(Root
27%).
Table
21.
Bupleurum
oils
of
Turkey
Plant
name
Part
yield
%
B.
cappadocicum
Flower
Fruit
Root
B.
croceum
(E)
Flower
Fruit
Root
B.
falcatum
subsp.
Flower
cernuum
(E)
Fruit
Root
B.
gerardii
(E)
Flower
Fruit
Root
B.
heldreichii
(E)
Flower
Fruit
Root
B.
intermedium
(E)
Flower
Fruit
Root
B.
lancifolium
(E)
Flower
Fruit
Root
B.
lycaonicum
(E)
Flower
Main
component
%
Ref.
heptanal
47
undecane
50
undecane
23
germacrene
D
13
undecane
13
hexadecanoic
acid
35
α-‐pinene
41
α-‐pinene
42
amylfuran
23
undecane
37
undecane
49
hexanal
22
germacrene
D
48
germacrene
D
48
hexadecanoic
acid
46
methyl
linoleate
21
germacrene
D
26
undecane
63
spathulenol
15
hexacosane
13
hexadecanoic
acid
14
tridecane
15
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
27
B.
pauciradiatum
(E)
B.
rotundifolium
(E)
B.
sulphureum
(E)
B.
turcicum
(E)
Fruit
Root
Flower
Flower
MD
Flower
Flower
Flower
n-‐hexane
MD
Fruit
Root
Flower
Fruit
Root
Flower
Fruit
Root
n-‐hexane
n-‐hexane
tridecane
37
spathulenol
14
germacrene
D
46,
β-‐
caryophyllene
18
germacrene
D
12,
β-‐
caryophyllene
10
hexadecanoic
acid
12
α-‐pinene
9,
β-‐phellandrene
7
α-‐pinene
28,
β-‐phellandrene
19
α-‐pinene
11
undecane
26,
tridecane
12
undecane
14
undecane
20
calarene
27
heptanal
33
heptanal
24
pentacosane
9
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
&
Akin
2009a
Saracoglu
&
Akin
2009a
Akin
et
al.,
2012
Saracoglu
&
Akin
2009b
Saracoğlu
&
Akin
2009b
Akin
et
al.,
2012
Akin
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
Saracoglu
et
al.,
2012
MD:
Microdistilled
OTHER
APIACEAE
OILS
This
part
of
the
treatise
comprises
the
remaining
Apiaceae
genera
not
covered
in
previous
pages
according
to
main
constituents
in
their
oils.
The
lists
also
contain
species
treated
previously.
Hence,
Apiaceae
oils
rich
in
monoterpene-‐hydrocarbons
(Table
22),
aliphatic
aldehydes
(Table
23),
alkanes
(Table
24),
alkanol
(Table
25),
aliphatic
esters
(Table
26),
phenylpropanoids
(Table
27)
and
sesquiterpenes
(Table
28).
Tables
29-‐37
display
Apiaceae
species
according
to
main
constituents
within
the
groups
of
compounds
contained
in
the
essential
oils.
Table
22.
Monoterpene-‐rich
Oils
Plant
name
Part
Angelica
sylvestris
var.
sylvestris
Artedia
squamata
Fruit
%
yield
0.26
Fruit
trace
Bilacunaria
anatolica
(E)
Fruit
0.17
Herba
0.14
Chaerophyllum
byzantinum
Herba
0.8
(E)
Chaerophyllum
libanoticum
Fruit
1.5
Chaerophyllum
macropodum
(E)
Crithmum
maritimum
Fruit
MD
Herba
0.85
Main
components
(%)
Ref.
α-‐pinene
26,
β-‐phellandrene
9,
bornyl
acetate
7,
p-‐cresol
7
trans-‐verbenol
14,
carvacrol
10,
hexadecanoic
acid
10
α-‐pinene
26,
camphene
19,
β-‐
caryophyllene
11
α-‐pinene
27,
caryophyllene
oxide
14
Ozek,
T.
et
al.,
2008
sabinene
27,
limonene
24,
γ-‐terpinene
19
Baser
et
al.,
2000g
Baser,
2002
Kurkcuoglu&Baser
Personal
Comm.
Kurkcuoglu&Baser
Personal
Comm.
sabinene
30,
p-‐cymen-‐8-‐ol
16,
terpinolene
Kurkcuoglu
et
al.,
12
2006
β-‐phellandrene
18,
limonene
16,
β-‐pinene
Demirci,
B.,
et
al.,
9,
sabinene
9
2007
p-‐cymene
39
Baser
et
al.,
2006
28
Herba
0.18-‐
0.28
Ozcan
et
al.,
2001
Herba
Senatore
et
al.,
2000
Herba
Daucus
littoralis
Diplotaenia
hayri-‐dumanii
(E)
Diplotaenia
cachrydifolia
Herba
Fruit
Leaf
Root
Fruit
Eryngium
campestre
Eryngium
thorifolium
Fuernrohria
setifolia
Herba
Herba
Herba
Fruit
Glaucosciadium
cordifolium
Herba
Lagoecia
cuminoides
Herba
γ-‐terpinene
8-‐35,
methyl
thymol
8-‐30,
p-‐
cymene
5-‐27,
terpinen-‐4-‐ol
1-‐21,
sabinene
0.1-‐21,
dill
apiole
0.1-‐21,
(Z)-‐β-‐ocimene
1-‐
13
0.17
1)
β-‐phellandrene
30,
methylthymol
25
0.19
2)
γ-‐terpinene
24,
dill
apiole
21
0.2
γ-‐terpinene
32-‐36,
β-‐phellandrene
21-‐22,
sabinene
9-‐13
0.2
cis-‐chrysanthenyl
acetate
47
MD
α-‐pinene
26,
2,5-‐dimethoxy-‐p-‐cymene
25,
β-‐pinene
18
1.67
terpinolene
65,
(E)-‐isodillapiole
18,
b-‐
phellandrene
5
0.33
(isomyristicin
21),
α-‐phellandrene
19,
β-‐
phellandrene
10,
methyl
oleate
10,
p-‐
cymene
8,
(E)-‐isodillapiole
6
2.9
terpinolene
69,
(E)-‐isodillapiole
8,
β-‐
phellandrene
7,
(E)-‐β-‐ocimene
5
0.34
α-‐pinene
5
0.68
α-‐pinene
59
MD
limonene
48,
carvon
14,
β-‐elemene
9
MD
limonene
70,
carvone
25
0.7
limonene
40,
α-‐pinene
12,
β-‐pinene
10
0.9-‐1.1
thymol
73-‐95
Laserpitium
petrophilum
(E)
Herba
1.34
α-‐pinene
49,
sabinene
26
Peucedanum
graminifolium
(E)
Peucedanum
palimbioides
Fruit
thymol
63,
carvacrol
23,
β-‐pinene
12
Trachyspermum
copticum
Fruit
Xanthogalum
purpurascens
(Angelica
purpurascens)
Fruit
0.8
L-‐N
Herba
0.53
α-‐pinene
53,
(E)-‐9-‐octadecanoic
acid
24,
β-‐
pinene
20
thymol
61,
p-‐cymene
16,
γ-‐terpinene
12
α-‐phellandrene
32,
β-‐phellandrene
23,
isopropylhexanoate
6,
limonene
5,
p-‐
cymene
4,
α-‐pinene
3,
bicyclogermacrene
12
L-‐N:
Likens-‐Nickerson
simultaneous
distillation-‐extraction;
MD:
Microdistilled
Table
23.
Aliphatic
aldehyde-‐rich
Oils
Plant
name
Part
%
yield
Bifora
radians
Herba
0.4
Cymbocarpum
Fruit
0.3
wiedemannii
Herba
0.6
Eryngium
creticum
Herba
0.21
Main
components
(%)
(E)-‐2-‐tridecenal
47,
(E)-‐2-‐tetradecenal
23
(E)-‐decenal
39,
(E)-‐2-‐dodecenal
16,
(E)-‐2-‐
tetradecenal
9
(E)-‐2-‐decenal
32,
2-‐decenoic
acid
20.
(E)-‐
2-‐dodecenal
11,
decanoic
acid
9
Hexanal
53,
heptanal
14,
octane
9
Ozcan
et
al.,
2006
Baser
et
al.,
2009
Kurkcuoglu&Baser
Personal
Comm.
Ozcan
et
al.,
2004
Ozcan
et
al.,
2004
Ozcan
et
al.,
2004
Celik
et
al.,
2011
Celik
et
al.,
2011
Ozek,
T.
et
al.,
2010
Ozek,
T.
et
al.,
2010
Baser
et
al.,
2000m
Baser
&
Tumen,
1994
Baser
&
Duman,
1997
Baser,
2002
Tepe
et
al.,
2011
Monguzzi
&
Akgül,
1993
Ozek,
G.,
et
al.,
2006b
Ref.
Baser
et
al.,
1998g
Baser
et
al.,
1999b
Baser
et
al.,
1999b
Celik
et
al.,
2011
29
Table
24.
Alkane-‐rich
Oils
Plant
name
Part
Heptaptera
anatolica
Fruit
%
yield
<0.1
Heptaptera
anisoptera
Fruit
<0.1
Heptaptera
cilicica
(E)
Fruit
<0.1
Heptaptera
triquetra
Fruit
<0.1
Hippomarathrum
cristatum
(Cachrys
cristata)
Herba
0.4
Part
Leaf
%
yield
Main
components
(%)
n-‐hexane
1-‐octadecanol
24,
hexadecanoic
acid
19
Ref.
Demirci,
B.,
et
al.,
2013
%
yield
0.74
Ref.
Ozer
et
2007
Main
components
(%)
nonacosane
24,
heptacosane
23
Ref.
Yılmaz
et
al.,
2009
nonacosane
69,
heptacosane
10,
hexadecanoic
Yılmaz
et
al.,
acid
7,
pentacosane
2,
octacosane
2
2009
nonacosane
39,
heptacosane
11,
pentacosane
Yılmaz
et
al.,
6,
hexahydrofarnesylacetone
5,
(E)-‐ 2009
geranylacetone
4
nonacosane
42,
heptacosane
23
Yılmaz
et
al.,
2009
hexadecanoic
acid
12,
nonacosane
8,
Ozek,
G.,
et
al
germacrene
D
6,
myristicin
4
2007a
Table
25.
Alkanol-‐rich
Oil
Plant
name
Actinolema
macrolema
Table
26.
Aliphatic
ester-‐rich
Oils
Plant
name
Part
Hippomarathrum
Herba
microcarpum
(Bilacunaria
microcarpa)
Malabaila
secacul
Fruit
Pastinaca
sativa
subsp.
urens
Zosima
absinthifolia
1.05
Fruit
2.5
Fruit
0.9
Table
27.
Phenylpropanoid-‐rich
Oils
Plant
name
Part
%
yield
Anthriscus
cerefolium
Herba
0.42
Main
components
(%)
Bornyl
acetate
20,
caryophyllene
oxide
8,
β-‐
caryophyllene
6,
trans-‐verbenol
6,
β-‐elemene
4,
germacrene
D
3
Hexyl
hexanoate
73,
hexyl
octanoate
9
Octyl
butyrate
80,
octyl
hexanoate
5,
phenylethyl
butyrate
2
octyl
acetate
38,
octyl
hexanoate
32
Main
components
(%)
methyl
chavicol
83,
1-‐allyl-‐2,4-‐
dimethoxybenzene
15,
undecane
2
methyl
chavicol
74,
1-‐allyl-‐2,4-‐
dimethoxybenzene
12
methyl
chavicol
96
Myrrhoides
nodosa
Herba
0.1
(Physocaulis
nodosa)
Scandix
australis
subsp.
Herba
0.4
grandiflora
Scandix
iberica
Fruit
n-‐hexane
methyl
chavicol
91
Flower
n-‐hexane
methyl
chavicol
86
al.,
Demirci,
B.,
et
al.,
2006
Kurkcuoglu
et
al.,
2006a
Baser
et
al.,
2000c
Ref.
Baser
et
al.,
1998a
Tumen
et
al.,
2005
Tumen
&
Baser
1997
Kaya
et
al.,
2007
Kaya
et
al.,
2007
30
Table
28.
Sesquiterpene-‐rich
Oils
Plant
name
Actinolema
macrolema
Part
Fruit
%
yield
2.3
Bilacunaria
aksekiensis
(E)
Fruit
0.26
Cachrys
alpina
(Prangos
ilanae)
Chaerophyllum
aksekiense
(E)
Fruit
Fruit
MD
1.1
Cnidium
silaifolium
subsp.
orientale
(E)
Ekimia
bornmuelleri
(E)
Grammosciadium
pterocarpum
Herba
0.09
Fruit
L-‐N
Fruit
MD
Leaf
MD
Herba
0.4
Fruit
MD
Herba
MD
Neocryptodiscus
papillaris
Fruit
0.12
Olymposciadium
caespitosum
(E)
(Aegokeras
caespitosa)
Fruit
Tr
Peucedanum
longifolium
Herba
0.75
Rhabdosciadium
microcalycinum
Szovitsia
callicarpa
Herba
Herba
Herba
Herba
Fruit
0.2
MD
0.6
MD
0.6
Trinia
glauca
Fruit
1.1
Xanthogalum
purpurescens
(Angelica
purpurascens)
Fruit
0.2
Hippomarathrum
boissieri
(Bilacunaria
boissieri)
Kundmania
anatolica
(E)
Main
components
(%)
guaia-‐5,7(11)-‐diene
37,
germacrene
B
25,
selina-‐
3,7(11)-‐diene12,
γ-‐guaiene
11
β-‐caryophyllene
41,
caryophyllene
oxide
8,
germacrene
B
8,
α-‐humulene
7
Ref.
Demirci,
B.,
et
al.,
2013
Kurkcuoglu&
Baser
Personal
Comm.
α-‐humulene
33
Baser
et
al.,
2004
(heptacosane
10),
humulene
epoxide
II
8,
(E)-‐β-‐ Baser
et
al.,
farnesene
6,
caryophyllene
oxide
6,
α-‐humulene
2000h
6,
terpinolene
6
kessane
33,
α-‐copaene
11,
β-‐caryophyllene
8,
α-‐ Polat
et
al.,
2011
pinene
8,
δ-‐cadinene
7
germacrene
D-‐4-‐ol
43,
α-‐cadinol
19,
δ-‐cadinene
Baser
et
al.,
1999
11
(Z)-‐β-‐farnesene
57,
β-‐caryophyllene
11,
γ-‐ Ozek,
T.,
et
al.,
2007b
terpinene
10,
β-‐elemene
8
(Z)-‐β-‐farnesene
11,
β-‐caryophyllene
10,
γ-‐ Ozek,
T.,
et
al.,
2007b
terpinene
2,
γ-‐elemene
1
β-‐caryophyllene
26,
caryophyllene
oxide
9,
α-‐ Baser
et
al.,
pinene
9
2000k
Rhabdosciadium
oligocarpum
(E)
caryophyllene
oxide
31,
muurola-‐4,10(14)-‐dien-‐1-‐ Kurkcuoglu&
Baser
Personal
ol
26,
δ-‐cadinene
15
Comm..
caryophyllene
oxide
19,
δ-‐cadinene
14,
β-‐ Kurkcuoglu
&
Baser
Personal
bisabolone
13,
muurola-‐4,10(14)-‐dien-‐1-‐ol
12
Comm..
α-‐humulene
20,
β-‐caryophyllene
17,
germacrene
Ozek,
G.
et
al.,
D
7
2010
germacrene
D
31,
β-‐ylangene
9,
β-‐cubebene
Kurkcuoglu
&
isomer
6,
bicyclosesquiphellandrene
5,
γ-‐ Baser
Personal
gurjunene
3,
eudesma-‐4(15),7-‐dien-‐1β-‐ol
3,
Comm..
octanal
3
8-‐cedren-‐13-‐ol
34,
myristicin
8,
germacrene
D
7,
Tepe
et
al
2011
δ-‐3-‐carene
6
germacrene
D
25
Baser
et
al.,
2006
germacrene
D
33
Baser
et
al.,
2006
germacrene
D
62
Baser
et
al.,
2006
germacrene
D
62
Baser
et
al.,
2006
α-‐kessyl
acetate
65,
longipinene
19
Demirci.
B.,
et
al.,
2010b
Baser
et
al.,
germacrene
D
20,
δ-‐cadinene
13,
α-‐pinene
13
1998d
bicyclogermacrene
12,
β-‐phellandrene
7,
Ozek,
G.,
et
al.,
spathulenol
7,
kessane
7
2006b
31
IMPORTANT
CONSTITUENTS
Table
29.
Monoterpene
Hydrocarbons
[Taxon
(plant
part)
%]
α-‐Pinene
β-‐Pinene
p-‐cymene
Sabinene
Camphene
Myrcene
α-‐phellandrene
β-‐phellandrene
δ-‐3-‐carene
γ-‐terpinene
Ferula
mervynii
(Fr)
80,
Ferula
elaeochytris
(Fr)
13-‐73,
Ferula
hermonis
(Fr)
72,
Prangos
platychlaena
(Fr)
70,
Ferula
lycia
(Fr)
15-‐69,
(H)
60;
Ferula
brevipedicellata
(Fr)
65,
Ferula
communis
(Fr)
60,
Ferula
rigidula
(Fr)
13-‐60,
Eryngium
thorifolium
(H)
59,
Peucedanum
palimbioides
(H)
53,
Laserpitium
petrophilum
(H)
49,
Bupleurum
falcatum
ssp.
cernuum
(Fl)
41,
(Fr)
42;
Prangos
uechtritzii
(Fr)
11-‐41,
Ferulago
sandrasica
(Fr)
12-‐41,
Johrenia
alpina
(Fr)
39,
Ferula
coskunii
(Fr)
37,
Seseli
campestre
(H)
26-‐36,
(Fr)
26;
Seseli
tourtuosum
(H)
36,
(Fr)
14;
Ferulago
aucheri
(Fr)
21-‐36,
Ferula
tingitana
(Fr)
11-‐36,
Ferula
parva
(Fr)
34,
Johrenia
silenoides
(Fr)
34,
Ferula
haussknechtii
(Fr)
32,
Ferulago
isaurica
(Fr)
32,
Ferulago
galbanifera
(Fr)
32,
Pimpinella
tragium
ssp.
pseudotragium
(S+L)
31,
Bupleurum
rotundifolium
(Fl)
9-‐28,
Echinophora
tournefortii
(H)
10-‐27,
Bilacunaria
anatolica
(H)
27,
(Fr)
26,
Diplotaenia
hayri-‐dumanii
(Fr)
26,
Angelica
sylvestris
var.
sylvestris
(S)
26,
Ferulago
mughlae
25,
Johrenia
polyscias
(Fr)
23,
(H)
19;
Prangos
ferulacea
(Fr)
13-‐18,
Pimpinella
nudicaulis
(H)
17,
Ferulago
longistylis
(Fr)
17,
Ferulago
idaea
(Fr)
16,
Pimpinella
tragium
ssp.
pseudotragium
(S+L)
31,
(Fr)
16;
Trinia
glauca
(Fr)
13,
Ferula
orientalis
(Fr)
13,
Prangos
platychlaena
ssp.
platychlaena
(Fr)
7-‐13,
Pimpinella
tragium
ssp.
polyclada
(S+L)
12,
Glaucosciadium
cordifolium
(H)
12,
Johrenia
alpina
(H)
12,
Pimpinella
aurea
(S+L)
12,
Ferulago
humulis
(Fr)
12,
Bupleurum
rotundifolium
(Fr)
11,
Ferulago
asparagifolia
(Fr)
11,
Ferulago
thirkeana
(Fr)
10,
Ferulago
pachyloba
(H)
10
Seseli
resinosum
(Fr)
38,
Pimpinella
saxifragra
(S+L)
28,
(Fr)
21;
Ferula
lycia
(Fr)
26,
(H)
19;
Peucedanum
palimbioides
(H)
20,
Johrenia
polyscias
(H)
18,
Diplotaenia
hayri-‐dumanii
(Fr)
18,
Ferula
communis
(Fr)
17,
Seseli
resinosum
(H)
16,
Cuminum
cyminum
(Fr)
3-‐16,
Ferula
elaeochytris
(Fr)
15,
Pimpinella
nudicaulis
(S+L)
15,
Ferula
tingitana
(Fr)
5-‐14,
Johrenia
silenoides
(Fr)
14,
Peucedanum
graminifolium
(Fr)
12,
Ferula
coskunii
(Fr)
11,
Glaucosciadium
cordifolium
(H)
10
Ferulago
sylvatica
(Fr)
46,
Chaerophyllum
macropodum
(Fr)
39,
Ferulago
macrosciadia
(Fr)
19-‐38,
Chritmum
maritimum
(H)
5-‐27,
Diplotenia
hayri-‐dumani
(Fr)
25,
Ferulago
confusa
(Fr)
24,
Ferulago
trachycarpa
(Fr)
22,
Prangos
denticulata
(Fr)
20,
Echinophora
orientalis
(H)
19,
Prangos
ilanae
(H)
19,
Ferulago
idea
(Fr)
18,
Cuminum
cyminum
(Fr)
5-‐18,
Ferulago
humilis
(Fr)
16,
Trachyspermum
copticum
(Fr)
16,
Echinophora
tenuifolia
ssp.
sibthorpiana
(H)
11-‐15,
Ferulago
galbanifera
(Fr)
12,
Prangos
uechtritzii
(H)
11,
Prangos
ferulacea
(Fr)
10-‐11
Ferula
coskunii
(Fr)
38,
Chaerophyllum
byzantinum
(H)
30,
Echinophora
trichophylla
(H)
27,
Crithmum
maritimum
(H)
5-‐27,
Laserpitium
petrophilum
(H)
26,
Prangos
denticulata
(Fr)
26,
Ferula
galbanifera
(Fr)
26,
Seseli
tortuosum
(Fr)
20,
(H)
19;
Pimpinella
tragium
ssp.
lithophila
(Fr)
16,
Laserpitium
hispidum
(R)
13,
Ferula
mervynii
(Fr)
12,
Seseli
petraeum
(H)
10
Ferula
haussknechtii
(Fr)
31,
Ferula
rigidula
(Fr)
15-‐20,
Bilacunaria
anatolica
(Fr)
19
Echinophora
orientalis
(H)
34,
Echinophora
tournefortii
(H)
30,
Ferulago
trachycarpa
(Fr)
20-‐
28,
Ferulago
isaurica
(R)
27,
(Fr)
17;
Pimpinella
saxifragra
(S+L)
19,
(Fr)
14;
Ferulago
asparagifolia
(Fr)
18,
Ferulago
syriaca
(Fr)
15,
Seseli
campestre
(Fr)
9
Echinophora
chrysantha
(H)
48-‐61,
Echinophora
tenuifolia
ssp.
sibthorpiana
(H)
16-‐52,
Angelica
purpurascens
(Fr)
32,
Prangos
ilanae
(H)
31,
Echinophora
lamondiana
(H)
28,
Diplotaenia
cachrydifolia
(R)
19,
Prangos
platychlaena
ssp.
platychlaena
(Fr)
0.1-‐18,
Ferula
orientalis
(H)
12,
Ferulago
galbanifera
(Fr)
11
Ferula
halophila
(Fr)
14-‐72,
Crithmum
maritimum
(H)
21-‐30,
Ferula
orientalis
((H)
24,
Prangos
platychlaena
ssp.
platychlaena
(Fr)
4-‐23,
Angelica
purpurascens
(Fr)
23,
Bupleurum
rotundifolium
(Fl)
7-‐19,
Chaerophyllum
libanoticum
(Fr)
18,
Prangos
ilanae
(H)
13,
Prangos
platychlaena
(Fr)
11,
Diplotaenia
cachrydifolia
(R)
10,
Prangos
uechtritzii
(Fr)
7-‐8
Prangos
denticulata
(R)
49,
Echinophora
lamondiana
(H)
48
Apium
graveolens
(H)
39,
Prangos
ferulacea
(Fr)
30-‐33,
Cuminum
cyminum
(Fr)
7-‐32,
Ferulago
trachycarpa
(Fr)
28,
Crithmum
maritimum
(H)
8-‐35,
Laserpitium
hispidum
(R)
15,
Trachyspermum
copticum
(Fr)
12,
Seseli
petraeum
(H)
11,
Grammosciadium
pterocarpum
32
Limonene
Terpinolene
(Z)-‐β-‐ocimene
(Fr)
10
Laser
trilobum
(Fr)
6-‐91,
Fuernrohria
setifolia
(Fr)
70,
(H)
48;
Pimpinella
puberula
(Fr)
63,
(S+L)
37,
Pimpinella
flabellifolia
(S+L)
17-‐47,
(Fr)
28,
(R)
17;
Glaucosciadium
cordifolium
(H)
40,
Ferulago
humilis
(Fr)
31,
Pimpinella
isaurica
(Fr)
24,
Crithmum
maritimum
(H)
24,
Ferulago
sandrasica
(Fr)
17,
Chaerophyllum
libanoticum
(Fr)
16,
Pimpinella
saxifraga
(H)
11,
Foeniculum
vulgare
var.
azoricum
(Fr)
8-‐11,
Ferulago
galbanifera
(Fr)
10
Diplotaenia
cachrydifolia
(Fr)
69,
(L)
65;
Ferulago
isaurica
(R)
42,
Ferulago
syriaca
(Fr)
13,
(R)
13,
Laserpitium
hispidum
(R)
12,
Chaerophyllum
byzantinum
(H)
12
Ferulago
trachycarpa
(H)
34,
Ferulago
humilis
(Fr)
32,
Ferulago
sandrasica
(Fr)
32,
Ferulago
trachycarpa
(Fr)
31,
Ferulago
pachyloba
(H)
26,
Ferulago
longistylis
(Fr)
16,
Crithmum
maritimum
(H)
1-‐13
Ferula
orientalis
(H)
14
(E)-‐β-‐ocimene
Table
30.
Oxygenated
Monoterpenes
Linalool
Coriandrum
sativum
var.
microcarpum
(Fr)
37-‐91Coriandrum
sativum
(Fr)
72-‐83,
Coriandrum
sativum
var.
macrocarpum
(Fr)
79,
Coriandrum
sativum
var.
vulgare
(Fr)
30-‐65,
Terpinen-‐4-‐ol
Crithmum
maritimum
(H)
1-‐21,
Echinophora
trichophylla
(H)
16
trans-‐Verbenol
Artedia
squamata
(Fr)
14
Carvone
Anethum
graveolens
(Fr)
46-‐66,
Fuernrohria
setifolia
(Fr)
25
Fenchone
Foeniculum
vulgare
var.
piperitum
(Fr)
18-‐28
Thymol
Lagoecia
cuminoides
(H)
73-‐95,
Peucedanum
graminifolium
(Fr)
63,
Trachyspermum
copticum
(Fr)
61
Carvacrol
Peucedanum
graminifolium
(Fr)
23,
Artedia
squamata
(Fr)
10
Carvacrol
methyl
ether
Ferulago
macrosciadia
(Fr)
72-‐78,
Ferulago
idaea
(Fr)
13
2,5-‐Dimethoxy-‐p-‐
Ferulago
humilis
(Fr)
76,
Ferulago
confusa
(Fr)
63,
Ferulago
sylvatica
(Fr)
40,
cymene
Diplotaenia
hayri-‐dumanii
(Fr)
25,
Ferulago
idaea
(Fr)
13
trans-‐Chrysanthenyl
Ferulago
silaifolia
(Fr)
84,
Ferulago
galbanifera
(Fr)
17,
Ferulago
sandrasica
(Fr)
12,
acetate
Ferulago
humulis
(Fr)
12
cis-‐Chrysanthenyl
Daucus
littoralis
(H)
47,
Ferulago
platycarpa
(H)
24
acetate
Cuminaldehyde
Cuminum
cyminum
(Fr)
19-‐40
p-‐Mentha-‐1,4-‐dien-‐7-‐al
Cuminum
cyminum
(Fr)
2-‐49
p-‐Mentha-‐1,3-‐dien-‐7-‐al
Cuminum
cyminum
(Fr)
4-‐13
Ferulagone
(NEW)
Ferulago
thirkeana
(Fr)
56-‐64
p-‐cymen-‐8-‐ol
Chaerophyllum
byzantinum
(H)
16
Methyl
thymol
Crithmum
maritimum
(H)
8-‐30
Table
31.
Phenyl
propanoids
1-‐Allyl-‐2,4-‐dimethoxybenzene
trans-‐Anethole
Methyl
chavicol
Chavicyl
angelate
trans-‐Epoxypseudoeugenyl
2-‐
Anthriscus
cerefolium
(H)
15,
Physocaulis
nodosa
(H)
12
Pimpinella
anisum
(Fr)
96-‐94,
Foeniculum
vulgare
var.
dulce
(Fr)
95,
Foeniculum
vulgare
var.
vulgare
(Fr)
65-‐88,
Foeniculum
vulgare
var.
azoricum
(Fr)
59-‐72,
Pimpinella
anisetum
(Fr)
81-‐77,
(S+L)
54;
Pimpinella
flabellifolia
(R)
68,
(Fr)
64,
(S+L)
41,
(H)
38;
Pimpinella
nudicaulis
(Fr)
64,
(S+L)
28,
(R)
13;
Scaligeria
lazica
(H)
50
Scandix
australis
ssp.
grandiflora
(H)
96,
Pimpinella
aromatica
(H)
92,
Scandix
iberica
(Fr)
91,
(Fl)
86;
Anthriscus
cerefolium
(H)
83,
Physocaulis
nodosa
(H)
74,
Foeniculum
vulgare
var.
piperitum
(Fr)
63-‐73,
(L)
25-‐70,
(S)
61,
(R)
59;
Pimpinella
anisetum
(H)
15-‐42,
(Fr)
16-‐22,
(S+L)
13;
Pimpinella
anisum
(Fr)
16,
Foeniculum
vulgare
var.
vulgare
(Fr)
4-‐16
Pimpinella
isaurica
(H)
44
Pimpinella
aromatica
(R)
40
33
methylbutyrate
Epoxypseudoisoeugenyl
2-‐
methylbutyrate
(=
4-‐Methoxy-‐2-‐
[(2R,3R)-‐3-‐
methyloxiranyl]phenyl(2S)-‐
methylbutyrate)
Methyl
eugenol
Myristicin
Isomyristicin
2,3,4,5-‐Tetramethoxy
allylbenzene
4-‐(Prop-‐2-‐enyl)phenyl
angelate
(NEW)
4-‐(3-‐Methyloxiranyl)phenyl-‐2-‐
methylbutyrate
(NEW)
Pimpinella
peucedanifolia
(R)
83,
Pimpinella
saxifraga
(R)
67,
Pimpinella
anisetum
(R)
56,
Pimpinella
cappadocica
(R)
43,
Pimpinella
corymbosa
(R)
43,
Pimpinella
aurea
(R)
39,
Pimpinella
kotschyana
(R)
36,
Pimpinella
olivieroides
(R)
33,
Pimpinella
peregrina
(R)
27,
Pimpinella
anisetum
(S+L)
24,
Pimpinella
tragium
ssp.
polyclada
(Fr)
20,
Pimpinella
tragium
ssp.
pseudotragium
(R)
19,
Pimpinella
tragium
ssp.
polyclada
(R)
16,
Pimpinella
tragium
ssp.
pseudotragium
(Fr)
10
Pimpinella
olivieroides
(Fr)
71,
(S+L)
52,
(R)
1;
Echinophora
tenuifolia
ssp.
sibthorpiana
(H)
18-‐59,
Pimpinella
puberula
(Fr)
30,
(S+L)
23;
Pimpinella
rhodantha
(Fr)
0.2
Laserpitium
hispidum
(R)
25
Diplotaenia
cachrydifolia
(R)
21
Petroselinum
sativum
(Fr)
29
Pimpinella
isaurica
(S+L)
43,
(Fr)
14,
(R)
11
Pimpinella
saxifraga
(R)
4,
(Fr)
0.7,
(S+L)
0.3;
Pimpinella
aurea
(R)
2,
(Fr)
1.2,
(S+L)
0.4;
Pimpinella
peucedanifolia
(R)
1,
Pimpinella
peregrina
(R)
0.3
trans-‐Isoosmorhizole
Pimpinella
nudicaulis
(R)
79,
(Fr)
21,
(S+L)
12;
Pimpinella
flabellifolia
(R)
2,
(H)
0.1;
Pimpinella
tragium
ssp.
pseudotragium
(R)
1,
(Fr)
0.6,
(S+L)
0.3;
Pimpinella
peregrina
(S+L)
0.3,
Pimpinella
saxifraga
(S+L)
0.1
4-‐(1-‐Prop-‐(1E)-‐enyl)phenyl
(2S)-‐
Pimpinella
olivieroides
(R)
39,
(Fr)
0.1;
Pimpinella
kotschyana
(R)
34,
(S+L)
methylbutyrate
(=
Anethol
2-‐
0.3,
(Fr)
0.1;
Pimpinella
corymbosa
(R)
33,
(S+L)
0.4;
Pimpinella
methylbutyrate)
peucedanifolia
(R)
6,
(S+L)
3,
(Fr)
2;
Pimpinella
saxifraga
(R)
3,
(Fr)
1.5,
(S+L)
1.3;
Pimpinella
peregrina
(S+L)
2,
(Fr)
0.3,
(R)
0.1;
Pimpinella
tragium
ssp.
lithophila
(Fr)
0.2;
Pimpinella
tragium
ssp.
pseudotragium
(S+L)
0.2,
(Fr)
0.2
4-‐(Prop-‐(1E)-‐enyl)phenyl
Pimpinella
peucedanifolia
(Fr)
2,
(S+L)
0.1;
Pimpinella
kotschyana
(R)
1,
isobutyrate
(S+L)
0.3,
(Fr)
0.3;
Pimpinella
corymbosa
(R)
0.5
4-‐(Prop-‐(1E)-‐enyl)phenyl
tiglate
=
Pimpinella
isaurica
(R)
16,
(S+L)
12,
(Fr)
1.4;
Pimpinella
aurea
(Fr)
3,
(R)
2,
anol
tiglate
(S+L)
1;
Pimpinella
tragium
ssp.
pseudotragium
(Fr)
1,
(R)
1,
(S+L)
0.4;
Pimpinella
cappadocica
var.
cappadocica
(R)
0.1
4-‐[(2R,3R)-‐3-‐Methyloxiranyl]phenyl
Pimpinella
aurea
(Fr)
0.3
tiglate
4-‐Methoxy-‐2-‐(prop-‐(1E)-‐enyl)phenyl
Pimpinella
isaurica
(S+L)
0.5,
(R)
0.2;
Pimpinella
anisetum
(S+L)
0.2,
(Fr)
angelate
0.2
4-‐Methoxy-‐2-‐[(2R,3R)-‐3-‐
Pimpinella
tragium
ssp.
polyclada
(R)
12,
(Fr)
6,
(S+L)
5;
Pimpinella
methyloxiranyl]phenyl
tiglate
isaurica
(R)
2,
(S+L)
0.3);
Pimpinella
cappadocica
var.
cappadocica
(R)
1;
Pimpinella
peregrina
(S+L)
1,
(R)
0.04;
Pimpinella
olivieroides
(R)
1,
Pimpinella
anisetum
(S+L)
0.3,
(R)
0.1;
Pimpinella
aurea
(R)
0.2,
Pimpinella
affinis
(R)
0.1
4-‐Methoxy-‐2-‐[(2R,3S)-‐3-‐
Pimpinella
peregrina
(R)
45,
(S+L)
6,
(Fr)
4;
Pimpinella
peucedanifolia
(R)
methyloxiranyl]phenylisobutyrate
2.4,
Pimpinella
kotschyana
(R)
1
4-‐Methoxy-‐2-‐(prop
(1E)-‐enyl)phenyl
Pimpinella
rhodantha
(R)
2,
(S+L)
0.2,
(Fr)
0.2;
Pimpinella
tragium
ssp.
tiglate
polyclada
(S+L)
1,
(R)
0.4
pseudoisoeugenyl
2-‐methylbutyrate
Pimpinella
aurea
(R)
4,
(S+L)
0.1;
Pimpinella
saxifraga
(R)
2,
Pimpinella
tragium
ssp.
polyclada
(S+L)
1,
(Fr)
1,
(R)
0.01;
Pimpinella
tragium
ssp.
pseudotragium
(R)
1,
(Fr)
1,
(S+L)
0.3;
Pimpinella
peregrina
(R)
1,
Pimpinella
anisum
(Fr)
1,
Pimpinella
cappadocica
var.
cappadocica
(R)
1,
Pimpinella
tragium
ssp.
lithophila
(R)
1,
(Fr)
0.1
4-‐Methoxy-‐2-‐[(2R,3R)-‐3-‐
Pimpinella
tragium
ssp.
polyclada
(R)
40,
(S+L)
2,
(Fr)
1;
Pimpinella
34
methyloxiranyl]phenylangelate
tragium
ssp.
pseudotragium
(R)
31,
(Fr)
1,
(S+L)
0.2;
Pimpinella
rhodantha
(R)
29,
(S+L)
3,
(Fr)
1;
Pimpinella
affinis
(R)
11,
(S+L)
0.2;
Pimpinella
anisetum
(R)
8,
(S+L)
5;
Pimpinella
peregrina
(S+L)
8,
Pimpinella
isaurica
(R)
7,
(S+L)
3,
(Fr)
0.1;
Pimpinella
cappadocica
var.
cappadocica
(R)
3
Pimpinella
olivieroides
(Fr)
14,
(H)
5
Crithmum
maritimum
(H)
0.1-‐21
Diplotaenia
cachrydifolia
(L)
18,
(Fr)
8,
(R)
6
cis-‐Isoelemicine
Dill
apiole
(E)-‐Isodillapiole
Table
32.
Aldehydes
2,3,6-‐Trimethylbenzaldehyde
2-‐Hydroxy-‐5-‐methoxy-‐benzaldehyde
Phenylacetaldehyde
(E)-‐2-‐Decenal
Decanal
Octanal
(E)-‐2-‐Dodecenal
(E)-‐2-‐Tridecenal
(E)-‐2-‐Tetradecenal
Heptanal
Hexanal
Table
33.
Alkane
derivatives
2,6-‐Dimethyl-‐1,3(E),5(E),7-‐
octatetraene
(=
(E,E)-‐cosmene)
2-‐Decenoic
acid
Decanoic
acid
Hexadecanoic
acid
Nonane
Nonene
Dodecanoic
acid
Undecane
Methyl
linoleate
Hexacosane
Tridecane
Pentacosane
Methyl
oleate
(E)-‐9-‐octadecanoic
acid
Nonacosane
Heptacosane
Ferulago
asparagifolia
(Fr)
39-‐42,
Ferulago
idaea
(Fr)
14
Scaligeria
lazica
(Hydrosol)22
Scaligeria
lazica
(Hydrosol)
14
Coriandrum
sativum
(H)
11-‐51,
Cymbocarpum
wiedemannii
(Fr)
39,
Cymbocarpum
wiedemannii
(H)
32,
Ferulago
trachycarpa
(R)
7
Coriandrum
sativum
(H)
10-‐23
Ferulago
trachycarpa
(R)
10
Cymbocarpum
wiedemannii
(Fr)
16,
Cymbocarpum
wiedemannii
(H)
11
Bifora
radians
(H)
47
Bifora
radians
(H)
23,
Cymbocarpum
wiedemannii
(Fr)
9
Bupleurum
cappadocicum
(Fl)
47,
Bupleurum
turcicum
(Fl)
33,
(Fr)
24;
Eryngium
creticum
((H)
14
Eryngium
creticum
(H)
53,
Bupleurum
gerardii
(R)
22
Echinophora
trichophylla
(H)
14
Cymbocarpum
wiedemannii
(H)
20
Cymbocarpum
wiedemannii
(H)
9
Bupleurum
heldreichii
(R)
46,
Tordylium
aegypticum
(Fr)
40,
Bupleurum
croceum
(R)
35,
Actinolema
macrolema
(L)
19,
Ferulago
isaurica
(H)
15,
Bupleurum
lancifolium
(R)
14,
Bupleurum
rotundifolium
(Fl)
12,
Cachrys
cristata
(H)
12,
Artedia
squamata
(Fr)
10,
Johrenia
polycias
(Fr)
9,
Johrenia
tortuosa
(H)
9
Ferula
elaeochytris
(Fr)
27
Prangos
uechtritzii
(Fr)
17
Johrenia
alpina
(H)
24,
Pimpinella
peucedanifolia
(Fr)
77,
(S+L)
65,
Bupleurum
intermedium
(R)
63,
Bupleurum
cappadocicum
(Fr)
50,
(R)
23;
Bupleurum
gerardii
(Fr)
49,
(Fl)
37;
Bupleurum
rotundifolium
(R)
26,
Bupleurum
sulphureum
(Fr)
20,
(Fl)
14;
Bupleurum
croceum
(Fr)
13,
Bupleurum
intermedium
(Fl)
21,
Bupleurum
lancifolium
(Fr)
13
Bupleurum
lycaonicum
(Fr)
37,
(Fl)
15;
Bupleurum
rotundifolium
(R)
12
Bupleurum
turcicum
(R)
9
Diplotaenia
cachrydifolia
(R)
10
Peucedanum
palimbioides
(H)
24
Heptaptera
anisoptera
(Fr)
69,
Heptaptera
triquetra
(Fr)
42,
Heptaptera
cilicica
(Fr)
39,
Ferulago
isaurica
(H)
26,
Heptaptera
anatolica
(Fr)
24,
Heptaptera
anatolica
(Fr)
23,
Heptaptera
triquetra
(Fr)
23,
Heptaptera
cilicica
(Fr)
11,
Heptaptera
anisoptera
(Fr)
10,
Chaerophyllum
aksekiense
35
1-‐Octadecanol
Octanol
(Fr)
10
Actinolema
macrolema
(L)
24
Heracleum
sphondylium
ssp.
ternatum
(Fr)
39-‐50,
Tordylium
lanatum
(Fr)
22,
Tordylium
apulum
(Fr)
17,
Tordylium
pestalozzae
(Fr)
15,
Tordylium
ketenoglui
(Fr)
12,
Tordylium
trachycarpum
(Fr)
11,
Tordylium
pustulosum
(Fr)
4-‐10
Table
34.
Sesquiterpene
hydrocarbons
β-‐Caryophyllene
Bilacunaria
aksekiensis
(Fr)
41,
Pimpinella
corymbosa
(H)
38,
(Fr)
14-‐33,
(S+L)
33;
Bilacunaria
boissieri
(H)
26,
Seseli
libanotis
(H)
20,
Bupleurum
pauciradiatum
(Fl)
10-‐
18,
Tordylium
aegypticum
(Fr)
11,
Bilacunaria
anatolica
(Fr)
11,
Grammosciadium
pterocarpum
(Fr)
11,
(L)
10
Germacrene
D
Rhabdosciadium
oligocarpum
(H)
62,
Prangos
sp.
nova
(Fr)
50,
Bupleurum
heldreichii
(Fl)
48,
(Fr)
48;
Smyrnium
perfoliatum
(Fr)
9-‐47,
Bupleurum
pauciradiatum
(Fl)
12-‐46,
Rhabdosciadium
microcalycinum
(H)
25-‐33,
Thecocarpus
carvifolius
(H)
31,
Aegokeras
caespitosa
(Fr)
27-‐31,
Ferula
anatolica
(Fr)
30,
Bupleurum
intermedium
(Fr)
26,
Ferula
duranii
(Fr)
25,
Trinia
glauca
(Fr)
20,
Pimpinella
rhodantha
(S+L)
17,
Seseli
resinosum
(Fr)
14,
Ferula
thirkeana
(Fr)
13-‐14,
Prangos
heyniae
(Fr)
3-‐14,
Bupleurum
croceum
(Fr)
13,
Pimpinella
corymbosa
(S+L)
12,
(Fr)
9,
Prangos
turcica
(Fr)
11,
Germacrene
B
Prangos
ferulacea
(Frcad)
30,
Actinolema
macrolema
(Fr)
19-‐24,
Seseli
gummiferum
ssp.
corymbosum
(H)
14,
Ferula
elaeochytris
(Fr)
10,
Prangos
heyniae
(Fr)
2-‐9
α-‐Humulene
Cachrys
alpina
(Fr)
33,
Neocryptodiscus
papillaris
(Fr)
20,
Prangos
pabularia
(Fr)
17,
Prangos
turcica
(Fr)
11,
Pimpinella
kotschyana
(Fr)
11,
(S+L)
9,
Ferulago
sandrasica
(Fr)
6,
Chaerophyllum
aksekiense
(Fr)
7,
Tordylium
syriacum
(Fr)
2-‐7
Kundmania
anatolica
(Fr)
15,
(H)
14,
Trinia
glauca
(Fr)
13,
Ferula
rigidula
(Fr)
6-‐13,
δ-‐Cadinene
Ekimia
bornmuelleri
(Fr)
11,
Seseli
libanotis
(H)
9
Bicyclogermacrene
Prangos
pabularia
(Fr)
16,
Johrenia
dichotoma
(Fr)
13,
Angelica
purpurascens
(Fr)
12,
Seseli
gummiferum
ssp.
corymbosum
(H)
12,
Pimpinella
cappadocica
var.
cappadocica
(Fr)
12
α-‐Selinene
Smyrnium
perfoliatum
(Fr)
31
(Z)-‐β-‐Farnesene
Scaligeria
lazica
(Fr)
89,
Pimpinella
tragium
ssp.
polyclada
(Fr)
57,
(S+L)
23;
Grammosciadium
pterocarpum
(Fr)
57,
(L)
11,
Pimpinella
rhodantha
(Fr)
35,
(S+L)
13,
Scaligera
tripartita
(S)
9,
Ferula
tingitana
(Fr)
4
(E)-‐β-‐Farnesene
Chaerophyllum
aksekiense
(Fr)
6
Bicyclosesquiphellandre Olymposciadium
caespitosum
(Fr)
5
ne
β-‐Bisabolene
Pimpinella
tragium
ssp.
lithophila
(Fr)
30,
Pimpinella
aurea
(Fr)
33,
Prangos
heyniae
(Fr)
10-‐12
Selina-‐3,7(11)-‐diene
Actinolema
macrolema
(Fr)
12-‐15
Actinolema
macrolema
(Fr)
11
γ-‐Guaiene
1,4-‐Dimethylazulene
Pimpinella
aromatica
(R)
9
4,10-‐Dihydro-‐1,4-‐
Pimpinella
aromatica
(R)
17,
Pimpinella
tragium
ssp.
lithophila
(R)
14,
Pimpinella
dimethylazulene
oliveiroides
(R)
6
4,6-‐Guaiadiene
Ferulago
syriaca
(Fr)
11,
Pimpinella
tragium
ssp.
lithophila
(R)
7,
(S+L)
0.3;
Pimpinella
kotschyana
(S+L)
2,
(Fr)
2,
(R)
1;
Pimpinella
corymbosa
(Fr)
1;
Pimpinella
peregrina
(S+L)
0.1
7-‐Epi-‐1,2-‐
Ferulago
uechtritzii
(Fr)
13
dehydrosesquicineole
(NEW)
Dehydrosesquicineole
Ferula
orientalis
(H)
10
Geijerene
Pimpinella
affinis
(Fr)
59,
(S+L)
40,
(R)
36;
Scaligeria
tripartita
(Fr)
55,
(H)
37;
36
Pregeijerene
Geijerene
isomer
γ-‐Himachalene
α-‐Zingiberene
trans-‐β-‐bergamotene
Eremophilene
Calarene
Guaia-‐5,7(11)-‐diene
Longipinene
Pimpinella
tragium
ssp.
lithophila
(S+L)
32,
(R)
27,
(Fr)
23;
Pimpinella
affinis
(Fr)
20,
(S+L)
11,
(R)
9;
Pimpinella
tragium
ssp.
lithophila
(S+L)
8,
Scaligeria
tripartita
(Fr)
6,
(H)
5,
Pimpinella
aromatica
(R)
5
Scaligeria
tripartita
(Fr)
12,
(H)
5
Pimpinella
cappadocica
var.
cappadocica
(Fr)
9,
Pimpinella
rhodantha
(Fr)
9
Pimpinella
isaurica
(Fr)
16,
Pimpinella
tragium
ssp.
pseudotragium
(Fr)
8
Pimpinella
peregrina
(S+L)
70,
(Fr)
41
Ferula
halophila
(Fr)
5-‐9,
Ferula
parva
(Fr)
9,
Ferula
rigidula
(Fr)
3
Bupleurum
sulphureum
(R)
27
Actinolema
macrolema
(Fr)
37
Szovitsia
callicarpa
(Fr)
19
Table
35.
Oxygenated
sesquiterpenes
Caryophyllene
oxide
Kundmannia
anatolica
(Fr)
31,
(H)
19,
Pimpinella
cappadocica
(Fr)
26,
Pimpinella
corymbosa
(S+L)
17,
(Fr)
11;
Bilacunaria
anatolica
(H)
14,
Echinophora
tournefortii
(H)
13,
Seseli
libanotis
(H)
12,
Ferula
lycia
(Fr)
3-‐10,
Tordylium
aegyptiacum
(Fr)
9,
Bilacunaria
boissieri
(H)
9,
Bilacunaria
microcarpa
(H)
8,
Bilacunaria
aksekiensis
(Fr)
8,
Ferulago
aucheri
(Fr)
8,
Chaerophyllum
aksekiense
(Fr)
6
Germacrene
D-‐4-‐ol
Ekimia
bornmuelleri
(Fr)
43,
Ferula
rigidula
(Fr)
8-‐10,
Prangos
turcica
(Fr)
5
4α-‐Hydroxy
germacra-‐1(10)-‐
Seseli
resinosum
(H)
30,
(Fr)
22,
5-‐diene
Isofuranogermacrene
Smyrnium
olusatrum
(R)
51,
Smyrnium
perfoliatum
(R)
48,
Smyrnium
rotundifolium
(Fr)
35-‐45
Furanodiene
Smyrnium
rotundifolium
(Fr)
28-‐39,
Smyrnium
perfoliatum
(Fr)
20
Acetoxyfuranoeudesm-‐3-‐ene
Smyrnium
perfoliatum
(Fr)
9
β-‐Bisabolenal
Prangos
heyniae
(Fr)
18-‐53
β-‐Bisabolenol
Prangos
heyniae
(Fr)
2-‐15
Cubenol
Ferulago
mughlae
(Fr)
13,
Ferulago
syriaca
(Fr)
9
Carotol
Daucus
carota
(Fr)
27-‐67,
Seseli
andronakii
(Fr)
53,
Seseli
petraeum
(H)
21
α-‐Cadinol
Ekimia
bornmuelleri
(Fr)
19,
Ferula
rigidula
(Fr)
5-‐10,
Prangos
sp.
nova
(Fr)
9
(E)-‐Sesquilavandulol
Seseli
tortuosum
(Fr)
37,
(H)
8;
Seseli
campestre
(Fr)
3-‐12,
Humulene
epoxide
II
Chaerophyllum
aksekiense
(Fr)
8,
Ferulago
aucheri
(Fr)
7
Spathulenol
Seseli
gummiferum
ssp.
gummiferum
(H)
20,
Bupleurum
lancifolium
(Fl)
15,
Johrenia
silenoides
(Fr)
15,
(H)
13;
Bupleurum
lycaonicum
(R)
14,
Seseli
libanotis
(H)
12,
Prangos
pabularia
(Fr)
11,
Ferulago
aucheri
(Fr)
7,
Xanthogalum
purpurascens
(Fr)
7,
Seseli
gummiferum
ssp.
corymbosum
(H)
6,
Johrenia
polyscias
(H)
6,
Johrenia
dichotoma
(Fr)
5
Kessane
Cnidium
silaifolium
ssp.
orientale
(H)
33,
Xanthogalum
purpurascens
(Fr)
7
Kessyl
acetate
Szovitsia
callicarpa
(Fr)
65
1-‐Methyl-‐4-‐(6-‐methylhepta-‐ Pimpinella
aurea
(Fr)
34,
(S+L)
20,
(R)
10;
Pimpinella
peregrina
(S+L)
3,
(Fr)
1,
(R)
1,5-‐dien-‐2-‐yl)-‐7-‐
0.2;
Pimpinella
tragium
ssp.
lithophila
(S+L)
0.2,
(R)
0.2,
(Fr)
0.1;
Pimpinella
oxabicyclo[4.1.0]
heptane
nudicaulis
(S+L)
0.1,
(R)
0.1,
(Fr)
0.02
(“aureane”)
(NEW)
4-‐(6-‐
Pimpinella
tragium
ssp.
lithophila
(S+L)
5,
(Fr)
2,
(R)
1;
Pimpinella
affinis
(S+L)
5,
Methylbicyclo[4.1.0]hept-‐2-‐ (Fr)
1,
(R)
0.6;
Pimpinella
puberula
(R)
1,
(S+L)
0.2;
Pimpinella
tragium
ssp.
en-‐7-‐yl)butan-‐2-‐one
pseudotragium
(R)
1,
Pimpinella
cappadocica
var.
cappadocica
(R)
0.1,
(“traginone”)
(NEW)
Pimpinella
rhodantha
(R)
0.1
Dictamnol
Pimpinella
tragium
ssp.
lithophila
(S+L)
6,
Pimpinella
affinis
(S+L)
4,
(Fr)
2,
(R)
1;
Pimpinella
puberula
(R)
3,
(S+L)
0.6;
Pimpinella
tragium
ssp.
pseudotragium
(R)
0.6;
Pimpinella
anisetum
(R)
0.5,
(S+L)
0.2;
Pimpinella
rhodantha
(S+L)
0.4,
(R)
37
Alismol
12-‐Hydroxy-‐β-‐caryophyllene
acetate
Himachalol
Dehydrocostuslactone
Shyobunone
Epi-‐shyobunone
6-‐Epi-‐shyobunone
β-‐Eudesmol
α-‐Eudesmol
Methylfarnesoate
Muurola-‐4,10(14)-‐dien-‐1-‐ol
8-‐Cedren-‐13-‐ol
Table
36.
Esters
Bornyl
acetate
Octyl
acetate
Octyl
hexanoate
Hexyl
butyrate
Hexyl
hexanoate
Hexyl
octanoate
Octyl
butyrate
Octyl
octanoate
Octyl
2-‐methylbutyrate
Table
37.
Others
Naphthalene
3,5-‐Nonadiyn-‐7-‐ene
3,5-‐Nonadiyn-‐2-‐yl
acetate
3,5-‐Nonadiyn-‐2-‐yl
acetate
isomer
3,5-‐Nonadiyne
Amylfuran
0.2;
Pimpinella
kotschyana
(R)
0.3,
(S+L)
0.1,
(Fr)
0.04;
Pimpinella
peucedanifolia
(S+L)
0.3,
Pimpinella
saxifraga
(R)
0.2,
Pimpinella
cappadocica
var.
cappadocica
(R)
0.1,
Pimpinella
rhodantha
(S+L)
1.4,
(R)
1;
Pimpinella
isaurica
(Fr)
0.4,
Pimpinella
peucedanifolia
(Fr)
0.3
Pimpinella
kotschyana
(Fr)
12,
(S+L)
5,
(R)
0.03;
Pimpinella
corymbosa
(Fr)
5,
(S+L)
3,
(R)
0.04
Pimpinella
cappadocica
var.
cappadocica
(S+L)
16
Pimpinella
cappadocica
var.
cappadocica
(Fr)
8
Ferula
drudeana
(Fr)
25-‐44
Ferula
drudeana
(Fr)
10-‐38
Ferula
drudeana
(Fr)
6-‐13
Ferula
szowitsiana
(L)
32,
(Stem)
30
Ferula
szowitsiana
(L)
18,
(Stem)
17
Johrenia
tortuosa
(Fr)
43,
Johrenia
dichotoma
(Fr)
17,
Johrenia
silenoides
(Fr)
9,
Kundmannia
anatolica
(Fr)
26,
(H)
12
Peucedanum
longifolium
(H)
34
Ferulago
syriaca
(R)
69,
Bilacunaria
macrocarpa
(H)
20,
Ferulago
longistylis
(H)
13,
(Fr)
4;Ferula
haussknechtii
(Fr)
7,
Prangos
turcica
(Fr)
7,
Angelica
sylvestris
var.
sylvestris
(S)
7,
Tordilium
ketenoglu
(Fr)
7,
Prangos
turcica
(Fr)
7,
Seseli
campestre
(H)
5,
Ferula
lycia
(H)
2,
Heracleum
paphlagonicum
(Fr)
27-‐95,
Heracleum
crenatifolium
(Fr)
19-‐95,
Heracleum
platytaenium
(Fr)
73-‐88,
(H)
86,
Zosima
absinthifolia
(Fr)
38,
Heracleum
sphondylium
ssp.
ternatum
(Fr)
7-‐31,
Heracleum
argeum
(Fr)
7
Tordylium
syriacum
(Fr)
46-‐81,
Tordylium
hasselquistiae
(Fr)
73,
Tordylium
pustulosum
(Fr)
69-‐73,
Tordylium
lanatum
(Fr)
59,
Tordylium
pestalozzae
(Fr)
56,
Tordylium
apulum
(Fr)
44,
Zosima
absinthifolia
(Fr)
32,
Heracleum
platytaenium
(H)
13,
(Fr)
3-‐5,
Heracleum
argaeum
(Fr)
9,
Pastinaca
sativa
ssp.
urens
(Fr)
5
Heracleum
argaeum
(Fr)
39,
Heracleum
paphlagonicum
(Fr)
17-‐25
Malabaila
secacul
(Fr)
73-‐86
Malabaila
secacul
(Fr)
9-‐14
Pastinaca
sativa
ssp.
urens
(Fr)
80,
H.
sphondylium
ssp.
ternatum
(Fr)
25-‐43,
Heracleum
platytaenium
(Fr)
12-‐17
Tordylium
trachycarpum
(Fr)
80,
Tordylium
apulum
(Fr)
35,
Tordylium
ketenoglui
(Fr)
29,
Tordylium
pestalozzae
(Fr)
16,
Tordylium
hasselquistiae
(Fr)
13,
Tordylium
aegyptiacum
(Fr)
9
Tordylium
pustulosum
(Fr)
18
Ferula
szowitsiana
(Fr)
28,
Ferula
lycia
(Fr)
3-‐27,
Ferula
anatolica
(Fr)
22,
Ferula
tingitana
(Fr)
14-‐15,
Ferula
duranii
(Fr)
10,
Prangos
turcica
(Fr)
9,
Ferula
parva
(Fr)
5,
Ferula
brevipedicellata
(Fr)
4,
Ferula
communis
(Fr)
4
Prangos
denticulata
(R)
20,
Prangos
platychlaena
ssp.
platychlaena
(Fr)
11-‐45,
Prangos
platychlaena
ssp.
platychlaena
(Fr)
4
Prangos
platychlaena
ssp.
platychlaena
(Fr)
6-‐25,
Bupleurum
falcatum
ssp.
cernuum
(R)
23
38
GENERAL
REMARKS
&
CONCLUSIONS
1.
In
this
paper,
essential
oil
compositions
of
179
Apiaceae
taxa
comprising
172
species
of
Turkey
belonging
to
53
genera
were
presented.
The
study
covered
at
least
392
oil
samples.
2.
All
the
oils
were
obtained
by
standard
procedures
and
analyzed
by
GC/MS
techniques
using
commercial
libraries
as
well
as
the
home-‐made
“Baser
Library
of
Essential
Oil
Constituents”
containing
MS
and
retention
data
of
over
4000
compounds.
3.
Some
Umbelliferae
fruits
were
found
particularly
rich
in
essential
oil,
such
as
Foeniculum
vulgare
var.
vulgare
6-‐12%,
Ferulago
isaurica
(E)
12%,
Foeniculum
vulgare
var.
piperitum
4.3-‐7.7%,
Heracleum
paphlagonicum
(E)
4.9-‐7.4%,
Ferulago
trachycarpa
7.3%,
Ferulago
asparagifolia
7.0%,
Laser
trilobum
5-‐7%,
Heracleum
platytaenium
(E)
5.2-‐6.8%,
Ferulago
longistylis
(E)
6.4%,
Pimpinella
anisetum
(E)
5.0-‐5.3%,
Pimpinella
aurea
5.1%,
Pimpinella
nudicaulis
5.1%,
Ferulago
syriaca
4.8%,
Pimpinella
anisum
1.3-‐4.8%,
Pimpinella
thirkeana
(E)
4.1%,
Ferulago
humilis
(E)
3.9%,
Ferulago
sandrasica
(E)
3.9%,
Ferula
drudeana
(E)
3.7-‐3.8%,
Heracleum
crenatifolium
(E)
3.7%,
Heracleum
sphondylium
subsp.
ternatum
3.7%,
Ferula
elaeochytris
3.5%,
Ferula
duranii
(E)
2.6%,
Anethum
graveolens
2-‐2.5%,
Actinolema
macrolema
2.3%,
Ferula
coskunii
(E)
2%,
Pimpinella
cappadocica
(E)
2%,
Pimpinella
flabellifolia
(E)
1.9%,
Ferula
brevipedicellata
1.9%.
Pimpinella
aromatica
(Herba)
6.1%,
(root)
4.2%.
4.
Chemical
diversity
in
the
family
Umbelliferae
is
evident.
5.
Some
genera
such
as
Pimpinella,
Anthriscus,
Foeniculum,
Petroselinum,
Scaligeria
are
rich
in
phenylpropanoids
and
have
commercial
importance.
•
Cuminum
cyminum,
Laser
trilobum,
Bunium
persicum
are
rich
in
monoterpene
aldehydes
and
possess
similar
odour
properties,
hence
have
commercial
importance.
•
Lagoecia
cuminoides,
Peucedanum
graminifolium,
Trachyspermum
copticum
are
rich
in
thymol.
Only
the
latter
species
is
known
in
commerce.
The
former
is
the
richest
ever
source
of
thymol
(up
to
95%).
Oil
yield
of
this
common
weed
is
over
1%.
In
some
western
parts
of
Turkey
it
is
used
as
Herbaal
tea.
If
cultivated
it
can
become
an
important
source
of
natural
thymol.
6.
Infraspecific
diversity
within
a
genus
is
also
interesting.
Essential
oils
may
have
chemotaxonomic
significance.
Some
marker
compounds
are
genus
or
species
specific,
e.g.,
compounds
such
as
anethole
and
epoxypseudoisoeugenyl-‐2-‐methylbutyrate
in
Pimpinella
and
Scaligeria;
furanosesquiterpenes
in
Smyrnium,
shyobunones
in
Ferula
drudeana,
(+)-‐linalool
in
Coriandrum
sativum.
7.
It
is
quite
frequent
for
Apiaceae
plants
to
show
different
chemical
profile
in
aboveground
and
underground
organs
of
the
same
plant
like
in
Pimpinella
peucedanifolia:
oils
of
fruits
and
leafy
stems
contain
undecane
as
main
constituent
while
root
oil
contains
epoxypseudoisoeugenyl-‐2-‐
methylbutyrate
and
4-‐methoxy-‐2-‐(3-‐methyloxiranyl)-‐phenylisobutyrate.
8.
Process
conditions
can
be
adjusted
to
obtain
aromachemicals
selectively
from
Umbelliferae
fruits
as
shown
in
Cumin
and
Laser
seed
oils.
9.
Taxonomic
studies
in
the
family
Apiaceae
are
ongoing
and
the
statuses
of
many
genera
are
continuously
modified.
Table
38
gives
a
summary
of
our
publications
reporting
essential
oils
of
the
species
whose
status
have
been
modified
39
Table
38.
New
names
of
the
species
studied
for
essential
oils
Old
name
New
name
Cachrys
alpina
M.
Bieb.
Echinophora
carvifolia
Boiss.
et
Balansa
Hippomarathrum
boissieri
Reut.
&
Hausskn.
ex
Boiss.
Hippomarathrum
cristatum
Boiss.
Hippomarathrum
microcarpum
(M.Bieb.)
B.Fedtsch.
Myrrhoides
nodosa
(L.)
Cannon
Olymposciadium
caespitosum
(Sibth.
&
Sm.)
H.Wolff
Xanthogalum
purpurascens
Ave-‐Lall.
Reference
Prangos
ilanae
Pimenov,
Akalın
&
Kljuykov
Baser
et
al.,
2004
Thecocarpus
carvifolius
(Boiss.)
Hedge
&
Baser,
Kurkcuoglu
et
al.,
1998
Lamond
Bilacunaria
boissieri
(Boiss.)
Pimenov
&
Baser
et
al.,
2000k
V.N.Tikhom.
Cachrys
cristata
DC.
Ozek,
G.,
et
al
2007a
Bilacunaria
microcarpa
(M.Bieb.)
Pimenov
Ozer
et
al.,
2007
&
V.N.Tikhom.
Physocaulis
nodosus
(L.)
Tausch
Tumen
et
al.,
2005
Aegokeras
caespitosa
(Sibth.
&
Sm.)
Raf.
Kurkcuoglu
&
Baser
Personal
Comm..
Angelica
purpurascens
(Ave-‐Lall.)
Gilli
Ozek,
G.,
et
al.,
2006b
40
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essential
oils
of
four
Heptaptera
species
growing
in
Turkey,
Chemistry
of
Natural
Compounds,
45(3),
431-‐433.
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Nese Kirimer