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LC-MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22.
[lamellar ichthyosis]
CYP
4
F
2
2
and
CYP
4
F
8
are
expressed
in
epidermis
,
and
mutations
of
CYP
4
F
2
2
are
associated
with
lamellar
ichthyosis
.
Epoxyalcohols
(
HEETs
)
and
epoxides
(
EETs
)
of
20
:
4
n-
6
appear
to
be
important
for
the
water
permeability
barrier
of
skin
.
Our
aim
was
to
study
the
MS
/
MS
spectra
and
fragmentation
of
these
compounds
and
to
determine
whether
they
were
oxidized
by
CYP
4
F
2
2
or
CYP
4
F
8
expressed
in
yeast
.
HEETs
were
prepared
from
15
-
hydroperoxyeicosatetraenoic
acid
(
15
-
HPETE
)
,
12
-
HPETE
,
and
their
[
(
2
)
H
(
8
)
]
labeled
isotopomers
,
and
separated
by
normal
phase-
HPLC
with
MS
/
MS
analysis
.
CYP
4
F
2
2
oxygenated
20
:
4
n-
6
at
C-
18
,
whereas
metabolites
of
HEETs
could
not
be
identified
.
CYP
4
F
8
formed
omega
3
hydroxy
metabolites
of
HEETs
derived
from
12
R-HPETE
with
11
,
12
-
epoxy-
10
-
hydroxy
configuration
,
but
not
HEETs
derived
from
15
S-HPETE
.
8
,
9
-
EET
and
11
,
12
-
EET
were
also
subject
to
omega
3
hydroxylation
by
CYP
4
F
8
.
We
conclude
that
CYP
4
F
8
and
CYP
4
F
2
2
oxidize
20
:
4
n-
6
and
that
CYP
4
F
8
selectively
oxidizes
8
,
9
-
EET
,
11
,
12
-
EET
,
and
10
,
11
R
,
12
R-HEET
at
the
omega
3
position
.
Diseases
Validation
Diseases presenting
"lamellar ichthyosis"
symptom
harlequin ichthyosis
lamellar ichthyosis
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