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Keywords:

  • pericosine B, C;
  • natural product;
  • fungal metabolite;
  • carbasugar;
  • enantiomeric mixture;
  • 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. Chirality 2011. © 2011 Wiley Periodicals, Inc.

Featured Compounds

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  1. 1 - 18
Compound 1
Molecular Weight:222.623
Molecular Formula:C8H11ClO5
InChIKey:AEDMWQPFIPNFCS-ZTYPAOSTSA-N
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Compound 2
Molecular Weight:218.2039
Molecular Formula:C9H14O6
InChIKey:VUQJXZNNVAWIKZ-DKXJUACHSA-N
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Compound 3
Molecular Weight:218.2039
Molecular Formula:C9H14O6
InChIKey:VUQJXZNNVAWIKZ-WCTZXXKLSA-N
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Compound 4
Molecular Weight:222.623
Molecular Formula:C8H11ClO5
InChIKey:AEDMWQPFIPNFCS-DBRKOABJSA-N
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Compound 5
Molecular Weight:408.785
Molecular Formula:C16H21ClO10
InChIKey:ASEVULJAKVHVDT-UQHZVBSCSA-N
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Compound 6
Molecular Weight:154.1632
Molecular Formula:C8H10O3
InChIKey:OZONFNLDQRXRGI-REJBHVJUSA-N
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Compound 7
Molecular Weight:188.1779
Molecular Formula:C8H12O5
InChIKey:KWZUWJOXBGYZBH-JWMKEVCDSA-N
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Compound 8
Molecular Weight:268.3056
Molecular Formula:C14H20O5
InChIKey:GWVWUDJUXCCJDW-FGLXMSFASA-N
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Compound 9
Molecular Weight:268.3056
Molecular Formula:C14H20O5
InChIKey:WXHNAVBCFPZHBX-GRYCIOLGSA-N
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Compound 10
Molecular Weight:400.367
Molecular Formula:C15H19F3O7S
InChIKey:YBKWJKOOTYVFSC-TUAOUCFPSA-N
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Compound 11
Molecular Weight:250.2903
Molecular Formula:C14H18O4
InChIKey:QVFBWTZXUZGAEI-NEPJUHHUSA-N
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Compound 12
Molecular Weight:347.202
Molecular Formula:C14H19BrO5
InChIKey:HHBZVESRUWAALW-YFKTTZPYSA-N
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Compound 13
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:AACNZPMBVVZNTR-WHOHXGKFSA-N
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Compound 14
Molecular Weight:298.3316
Molecular Formula:C15H22O6
InChIKey:ZAGGVWSNVBWVQN-LPWJVIDDSA-N
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Compound 15
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:AACNZPMBVVZNTR-BJDJZHNGSA-N
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Compound 16
Molecular Weight:298.3316
Molecular Formula:C15H22O6
InChIKey:KFPVEYKDIURNAQ-RVMXOQNASA-N
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Compound 17
Molecular Weight:296.3157
Molecular Formula:C15H20O6
InChIKey:QWRWEYKVGGJJAW-UHTWSYAYSA-N
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Compound 18
Molecular Weight:298.3316
Molecular Formula:C15H22O6
InChIKey:KFPVEYKDIURNAQ-LOWDOPEQSA-N
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  1. 1 - 18