Chemistry Reference
In-Depth Information
Topography of the MP
0
mm
Eccentricity
-2.75
-1.25
+1.25
+2.75
9.4
°
4.3
°
4.3
°
9.4
°
degrees
2.5 mm
5.5 mm
D
C
A
a
a: Foveola
A: Fovea
C: Parafovea
D: Perifovea
1.5 mm
0.35 mm
0.4 μm
-0.75
-0.175
+0.175
+0.75
mm
Eccentricity
degrees
2.6
°
0.6
°
0.6
°
2.6
°
0
FIGURE 13.4 (See color insert following page 336.)
Topography of the MP. This i gure schematically
shows the distribution of the yellow MP across the retina: horizontally (top) and vertically (bottom). (From
Gass, J.D.,
Stereoscopic Atlas of Macular Diseases Diagnosis and Treatment
, Vol. 1, Mosby - Year Book Inc.,
3, 1997. With permission.)
As already mentioned, macular zeaxanthin comprises two stereoisomers, the normal dietary
(3
R
,3
S
)-zeaxanthin(=(
meso
)-zeaxanthin), of which the latter is not normally
a dietary component (Bone et al. 1993) and is not found in any other compartment of the body except in
the retina. The concentration of (
meso
)-zeaxanthin in the retina decreases from a maximum within the
central fovea to a minimum in the peripheral retina, similar to the situation with (3
R
,3
′
R
)-zeaxanthin and (3
R
,3
′
R
)-zeaxanthin.
This distribution inversely rel ects the relative concentration of lutein in the retina and gave rise to
a hypothesis (Bone et al. 1997) that (
meso
)-zeaxanthin is formed in the retina from lutein. This was
coni rmed by an experiment in which xanthophyll-depleted monkeys had been supplemented with
chemically pure lutein or (3
R
,3
′
R
)-zeaxanthin (Johnson et al. 2005). (
Meso
)-Zeaxanthin was exclu-
sively detected in the retina of lutein-fed monkeys but not in retinas of zeaxanthin-fed animals, dem-
onstrating that it is a retina-specii c metabolite of lutein only. The mechanism of its formation has not
been established but may involve oxidation-reduction reactions that are mediated photochemically,
enzymatically, or both. Thus, (
meso
)-zeaxanthin is a metabolite unique to the primate macula.
The observation that lutein in the retina is converted to (
meso
)-zeaxanthin appears to be physio-
logically plausible: due to the presence of, in comparison to lutein, one additional conjugated double
bond, it has a stronger singlet oxygen quenching capability (Cantrell et al. 2003). Furthermore, it has
been reported that (
meso
)-zeaxanthin provides a somewhat better protection against the oxidation
′
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