Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals
In order to determine the absolute configuration of naturally occurring alloxanthin, a HPLC analytical method for three stereoisomers 1a–c 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...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2014-05-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/12/5/2623 |
| _version_ | 1828115670378741760 |
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| author | Yumiko Yamano Takashi Maoka Akimori Wada |
| author_facet | Yumiko Yamano Takashi Maoka Akimori Wada |
| author_sort | Yumiko Yamano |
| collection | DOAJ |
| description | In order to determine the absolute configuration of naturally occurring alloxanthin, a HPLC analytical method for three stereoisomers 1a–c 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 1a–c. |
| first_indexed | 2024-04-11T12:44:04Z |
| format | Article |
| id | doaj.art-3ef7283e1d374c18b1759f83557cd528 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T12:44:04Z |
| publishDate | 2014-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-3ef7283e1d374c18b1759f83557cd5282022-12-22T04:23:25ZengMDPI AGMarine Drugs1660-33972014-05-011252623263210.3390/md12052623md12052623Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic AnimalsYumiko Yamano0Takashi Maoka1Akimori Wada2Kobe Pharmaceutical University, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, JapanResearch Institute for Production Development, 15 Shimogamo-morimoto-cho, Sakyo-ku, Kyoto 606-0805, JapanKobe Pharmaceutical University, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, JapanIn order to determine the absolute configuration of naturally occurring alloxanthin, a HPLC analytical method for three stereoisomers 1a–c 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 1a–c.http://www.mdpi.com/1660-3397/12/5/2623carotenoidalloxanthinsynthesischiral HPLC separationabsolute configuration |
| spellingShingle | Yumiko Yamano Takashi Maoka Akimori Wada Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals Marine Drugs carotenoid alloxanthin synthesis chiral HPLC separation absolute configuration |
| title | Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals |
| title_full | Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals |
| title_fullStr | Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals |
| title_full_unstemmed | Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals |
| title_short | Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals |
| title_sort | synthesis of 3s 3 s and meso stereoisomers of alloxanthin and determination of absolute configuration of alloxanthin isolated from aquatic animals |
| topic | carotenoid alloxanthin synthesis chiral HPLC separation absolute configuration |
| url | http://www.mdpi.com/1660-3397/12/5/2623 |
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