Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596556
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

Autoxidation of betulonaldehyde

S Ayers
1   Pharmaceutical Development, Bristol-Myers Squibb Co., 1 Squibb Dr., New Brunswick, NJ 08903, USA
,
T Benkovics
1   Pharmaceutical Development, Bristol-Myers Squibb Co., 1 Squibb Dr., New Brunswick, NJ 08903, USA
,
J Marshall
1   Pharmaceutical Development, Bristol-Myers Squibb Co., 1 Squibb Dr., New Brunswick, NJ 08903, USA
,
Y Tan
1   Pharmaceutical Development, Bristol-Myers Squibb Co., 1 Squibb Dr., New Brunswick, NJ 08903, USA
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Publikationsdatum:
14. Dezember 2016 (online)

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    Betulonaldehyde is a pentacyclic triterpenoid found in Betula sp. as a minor constituent along with the major secondary metabolites betulin and betulinic acid. In a stability study, betulonaldehyde was stirred in acetone at room temperature under air. Three major degradants were detected, and were isolated after 12 days. HRMS showed that for one of the degradants, a single oxygen atom had been added, and this product was confirmed by HPLC (retention time match to an authentic standard) and NMR to be betulonic acid. The remaining two degradants also gained oxygen, but lost a carbon. HRMS and NMR data showed that these degradants were C17 hydroperoxide epimers. The identity of the stereochemical configuration at C17 for each these hydroperoxides was deduced by 2D-NOESY correlations and the coupling pattern for H18.

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    Acknowledgements: Drs. Charles Pathirana and Scott Miller are acknowledged for helpful discussions.

    Keywords: betulonaldehyde, autoxidation, hydroperoxide.


     

    Die Autoren geben an, dass kein Interessenkonflikt besteht.

     
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