Jump to main content
Jump to site search

Issue 43, 2016
Previous Article Next Article

Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

Author affiliations

Abstract

A practical synthesis of 28a-homo-28a-selenolupane triterpenes and the corresponding selenosaponins containing D-mannose, L-arabinose, L-rhamnose, and D-idose moieties is described. Selenium containing triterpenes were obtained from the readily available 3-O-allyl-homobetulin mesylate by nucleophilic substitution with the selenocyanate ion which upon reduction of the –SeCN group afforded the free selenol. Glycosylation using classical Schmidt donors gave 1,2-trans selenosaponins as the main product as well as minute amounts of 1,2-cis isomers. This is one of the very few examples of the synthesis of selenoglycosides by direct glycosylation of free selenols. The studied selenol showed high resistance to air oxidation resulting in good stability during the synthesis of selenolupane derivatives. Cytotoxic activities of new homoselenolupane derivatives were also evaluated in vitro and revealed that some triterpenes exhibited an interesting profile against human cancer cell lines.

Graphical abstract: Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Sep 2016, accepted on 07 Oct 2016 and first published on 07 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01938B
Citation: Org. Biomol. Chem., 2016,14, 10238-10248
  • Open access: Creative Commons BY license
  •   Request permissions

    Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

    K. Sidoryk, L. Rárová, J. Oklešťková, Z. Pakulski, M. Strnad, P. Cmoch and R. Luboradzki, Org. Biomol. Chem., 2016, 14, 10238
    DOI: 10.1039/C6OB01938B

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements