Regioisomeric Lutein Esters
J. Agric. Food Chem., Vol. 55, No. 13, 2007 4971
ACKNOWLEDGMENT
Table 4. NMR Chemical Shifts of C-3 and C-3′ Protons in Lutein and
Its Palmitate Esters
We acknowledge the able assistance of John Nikiforuk in
determining the H NMR spectra.
chemical shift (ppm)
C-3′
1
compound
lutein
lutein 3
C-3
3.85
3.85
5.01
5.01
4.12
5.26
4.12
5.26
LITERATURE CITED
′
-O-palmitate
lutein 3-O-palmitate
lutein dipalmitate
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Table 5. Ester Composition of a Commercial Lutein Supplement
(
(
(
compound relative
composition %
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lutein 3
′
-O-myristate (5a)
0.2
0.1
0.8
0.3
±
±
±
±
0.02a
0.01
0.02
0.03
Arch. Gefuegelk. 2000, 64, 45-54.
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lutein 3-O-myristate (5b)
lutein 3 -O-palmitate (6a)
′
lutein 3-O-palmitate (6b)
homogeneous diesters
lutein dimyristate (10)
lutein dipalmitate (14)
lutein distearate (17)
mixed diesters
9.2
39.9
1.1
±
±
±
0.93
0.78
0.07
(
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lutein 3
lutein 3
lutein 3
lutein 3
lutein 3
lutein 3
lutein 3
lutein 3
lutein 3
′
′
′
′
′
′
′
′
′
′
-O-laurate-3-O-myristate (9a)
-O-myristate-3-O-laurate (9b)
-O-laurate-3-O-palmitate (11a)
-O-palmitate-3-O-laurate (11b)
-O-myristate-3-O-palmitate (12a)
-O-palmitate-3-O-myristate (12b)
-O-myristate-3-O-stearate (15a)
-O-stearate-3-O-myristate (15b)
-O-palmitate-3-O-stearate (16a)
-O-stearate-3-O-palmitate (16b)
0.7
0.7
1.3
±
±
±
±
±
±
±
±
±
±
0.04
0.04
0.12
0.06
0.25
0.58
0.24
0.11
0.29
0.43
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1.0
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12.5
2.0
1.4
4.4
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a
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Average of triplicate determinations
± standard deviation.
for the in vitro isomers. General agreement was observed
between the values of diesters taken from the lutein supplement
and averages of literature values for native marigold esters (10-
2). In the present and previous studies (10-12), lutein
dipalmitate is present at the highest level (39.9 vs 36.5%,
(
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4
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respectively), followed by lutein 3′-O-myristate-3-O-palmitate
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(
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(
two mixed diesters were observed as one compound in the
previous studies (10-12) averaging 24.7%, which is close to
the sum of the two mixed regioisomeric diesters (31.2%). The
fourth highest compound in the present and previous studies is
lutein dimyristate (9.2 vs 12.8%, respectively).
(
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There is growing evidence for the role of lutein in the health
of eyes and skin, which has led to increasing demands for lutein
supplements and product. This study provides analytical tech-
niques for the identification and quantification of lutein esters
in lutein supplements and lutein-containing products using
synthetic lutein esters. From mass spectrometric and NMR
properties of 20 synthetic lutein esters, it was possible to assign
unequivocal structures to the regioisomers in order of LC
elution. These compounds were then used to identify 17 lutein
esters found in a commercial lutein supplement. The present
method would help to improve quality control of lutein
supplements and other lutein-based products.
(
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(
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(
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APCI+ve, atmospheric pressure chemical ionization
positive ion mode; LC, liquid chromatography; MS, mass
spectrometry; NMR, nuclear magnetic resonance; UV-vis,
ultraviolet-visible.
(
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