Natural pericosines B and C as enantiomeric mixtures: direct evidence by chiral HPLC analysis |
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Authors: | Usami Yoshihide Okada Yusuke Yamada Takeshi |
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Institution: | Department of Pharmaceutical Sciences Laboratory of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, Takatsuki, Osaka, Japan. usami@gly.oups.ac.jp |
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Abstract: | Pericosines are carbasugar-type metabolites of Periconia byssoides OUPS-N133, a fungus that was originally separated from the sea hare Aplysia kurodai. It has been reported that pericosines C and E are enantiomeric mixtures. The difference in specific rotation between natural pericosine C and the synthetic one led to the conclusion that natural pericosine C is an enantiomeric mixture. Meanwhile, the small specific rotation of natural pericosine B compared to that of the synthetic one led to the deduction that natural pericosine B might also be an enantiomeric mixture. Then, racemic pericosines B and C were synthesized, and the direct enantioseparation of these racemic carbasugars was conducted with CHIRALPAK? IA and CHIRALPAK? AY-H, which are suitable columns for racemic pericosines B and C, respectively. Using chiral HPLC, we conclude that natural pericosines B and C exist as enantiomeric mixtures. A rare example of the application of direct chiral HPLC analysis to intact sugars or carbasugars was provided. |
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