Literature DB >> 21793522

Revision of the absolute configurations of bethosides B and C and their aglycone.

Victoria L Challinor1, Patricia Y Hayes, Paul V Bernhardt, William Kitching, Reginald P Lehmann, James J De Voss.   

Abstract

The absolute stereochemistry of the steroidal saponins bethosides B and C was previously assigned as (22R,25R) on the basis of work that employed Horeau's method. Our studies of helosides A and B created doubt about both the original assignment and consequently our conclusion that relied upon it. The absolute configurations of bethosides B and C are revised to (22S,25R) following X-ray crystallographic analysis of their aglycone. Synthesis and full spectral characterization of both the 22R and 22S aglycones is reported to facilitate future stereochemical assignments in this series of saponins.

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Year:  2011        PMID: 21793522     DOI: 10.1021/jo2012797

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  New cholestane glycosides and sterols from the underground parts of Chamaelirium luteum and their cytotoxic activity.

Authors:  Akihito Yokosuka; Kenichi Takagi; Yoshihiro Mimaki
Journal:  J Nat Med       Date:  2012-11-16       Impact factor: 2.343

2.  Cholestane steroid glycosides from the rhizomes of Dioscorea villosa (wild yam).

Authors:  Zulfiqar Ali; Troy J Smillie; Ikhlas A Khan
Journal:  Carbohydr Res       Date:  2013-01-09       Impact factor: 2.104

  2 in total

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