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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
1 Kobe Pharmaceutical University, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan 2 Research Institute for Production Development, 15 Shimogamo-morimoto-cho, Sakyo-ku, Kyoto 606-0805, Japan
* Author to whom correspondence should be addressed.
Received: 20 March 2014 / Revised: 15 April 2014 / Accepted: 15 April 2014 / Published: 8 May 2014
(This article belongs to the Special Issue Marine Carotenoids (Special Issue))
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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 (CC BY 3.0).

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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.

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