title: Natural pericosines B and C as enantiomeric mixtures: direct evidence by chiral HPLC analysis.
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.
authors: Department of Pharmaceutical Sciences Laboratory of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, Takatsuki, Osaka, Japan. usami@gly.oups.ac.jp
authors: Yoshihide
authors: Y
authors: Usami
authors: Yusuke
authors: Y
authors: Okada
authors: Takeshi
authors: T
authors: Yamada
mesh_terms: D000818:Animals; D001048:Aplysia / Q000378:metabolism; D002241:Carbohydrates / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D005658:Fungi / Q000378:metabolism; D008956:Models, Chemical; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D013055:Spectrophotometry, Infrared / Q000379:methods; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; C496389:pericosine B; C544052:pericosine C; D012765:Shikimic Acid