Properties of astaxanthin/Ca2+ complex formation in the deceleration of Cis/trans isomerization

Chien Sheng Chen; Shih Hsiung Wu; Ying Ying Wu; Jim Min Fang; Tzu Hua Wu

doi:10.1021/ol0709533

Properties of astaxanthin/Ca²⁺ complex formation in the deceleration of Cis/trans isomerization

Chien Sheng Chen, Shih Hsiung Wu, Ying Ying Wu, Jim Min Fang, Tzu Hua Wu

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

Abstract

Deceleration of the regioselective cis/trans isomerization of all-trans-astaxanthin (ASTX) in the presence of Ca²⁺ was shown by HPLC analysis. The NMR and ITC analyses provided evidence for complexation of ASTX with Ca²⁺ in 1:2 stoichiometry via chelation at both carbonyl and hydroxyl groups. The rotation across torsion ω6 (C5-C6-C7-C8) upon complexation is consistent with the NOE between 7-H and 5-CH₃. This study supports the inhibitory effect of ASTX on calcium-induced turbidity of lens crystallins.

Original language	English
Pages (from-to)	2985-2988
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	16
DOIs	https://doi.org/10.1021/ol0709533
Publication status	Published - Aug 2 2007

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Properties of astaxanthin/Ca2+ complex formation in the deceleration of Cis/trans isomerization",

abstract = "Deceleration of the regioselective cis/trans isomerization of all-trans-astaxanthin (ASTX) in the presence of Ca2+ was shown by HPLC analysis. The NMR and ITC analyses provided evidence for complexation of ASTX with Ca2+ in 1:2 stoichiometry via chelation at both carbonyl and hydroxyl groups. The rotation across torsion ω6 (C5-C6-C7-C8) upon complexation is consistent with the NOE between 7-H and 5-CH3. This study supports the inhibitory effect of ASTX on calcium-induced turbidity of lens crystallins.",

author = "Chen, {Chien Sheng} and Wu, {Shih Hsiung} and Wu, {Ying Ying} and Fang, {Jim Min} and Wu, {Tzu Hua}",

year = "2007",

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T1 - Properties of astaxanthin/Ca2+ complex formation in the deceleration of Cis/trans isomerization

AU - Chen, Chien Sheng

AU - Wu, Shih Hsiung

AU - Wu, Ying Ying

AU - Fang, Jim Min

AU - Wu, Tzu Hua

PY - 2007/8/2

Y1 - 2007/8/2

N2 - Deceleration of the regioselective cis/trans isomerization of all-trans-astaxanthin (ASTX) in the presence of Ca2+ was shown by HPLC analysis. The NMR and ITC analyses provided evidence for complexation of ASTX with Ca2+ in 1:2 stoichiometry via chelation at both carbonyl and hydroxyl groups. The rotation across torsion ω6 (C5-C6-C7-C8) upon complexation is consistent with the NOE between 7-H and 5-CH3. This study supports the inhibitory effect of ASTX on calcium-induced turbidity of lens crystallins.

AB - Deceleration of the regioselective cis/trans isomerization of all-trans-astaxanthin (ASTX) in the presence of Ca2+ was shown by HPLC analysis. The NMR and ITC analyses provided evidence for complexation of ASTX with Ca2+ in 1:2 stoichiometry via chelation at both carbonyl and hydroxyl groups. The rotation across torsion ω6 (C5-C6-C7-C8) upon complexation is consistent with the NOE between 7-H and 5-CH3. This study supports the inhibitory effect of ASTX on calcium-induced turbidity of lens crystallins.

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Properties of astaxanthin/Ca²⁺ complex formation in the deceleration of Cis/trans isomerization

Abstract

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