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Mar. Drugs 2014, 12(5), 2623-2632; doi:10.3390/md12052623
Article

Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals

1,* , 2
 and 1
Received: 20 March 2014; in revised form: 15 April 2014 / Accepted: 15 April 2014 / Published: 8 May 2014
(This article belongs to the Special Issue Marine Carotenoids)
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Abstract: In order to determine the absolute configuration of naturally occurring alloxanthin, a HPLC analytical method for three stereoisomers 1ac was established by using a chiral column. Two authentic samples, (3S,3′S)- and meso-stereoisomers 1b and 1c, were chemically synthesized according to the method previously developed for (3R,3′R)-alloxanthin (1a). Application of this method to various alloxanthin specimens of aquatic animals demonstrated that those isolated from shellfishes, tunicates, and crucian carp are identical with (3R,3′R)-stereoisomer 1a, and unexpectedly those from lake shrimp, catfish, biwa goby, and biwa trout are mixtures of three stereoisomers of 1ac.
Keywords: carotenoid; alloxanthin; synthesis; chiral HPLC separation; absolute configuration carotenoid; alloxanthin; synthesis; chiral HPLC separation; absolute configuration
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Yamano, Y.; Maoka, T.; Wada, A. Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals. Mar. Drugs 2014, 12, 2623-2632.

AMA Style

Yamano Y, Maoka T, Wada A. Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals. Marine Drugs. 2014; 12(5):2623-2632.

Chicago/Turabian Style

Yamano, Yumiko; Maoka, Takashi; Wada, Akimori. 2014. "Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals." Mar. Drugs 12, no. 5: 2623-2632.



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