Synthesis and Mass Spectral Fragmentation Patterns of Brassinolide Early Biosynthetic Precursors Labeled at C-26

Khripach V. A., Tarkowská D., Zhabinskii V. N., Gulyakevich O. V., Ermolovich Y. V., Drašar P., Strnad M.
NATURAL PRODUCT COMMUNICATIONS 8: 771-774, 2013

Keywords: Brassinosteroids, Brassinolide, Biosynthesis, 6-Deoxoteasterone, 3-Dehydro-6-deoxoteasterone, Isotope labeling, Mass spectrometry.
Abstract: New analogues of brassinolide biosynthetic precursors with three deuterium atoms at non-exchangeable positions have been synthesized to be used as standards for quantification of natural brassinosteroids by liquid chromatography-mass spectrometry. [26-2H3](22R,23R,24S)-22,23-Dihydroxy-6-methoxy-24-methyl-3,5-cyclo-5-cholestane was used as a starting material for the preparation of campestane derivatives having a 22R,23R-diol functionality and either a hydroxy or keto group at C-3 and labeled at C-26. The mass spectrometric behavior of the newly synthesized compounds has been studied.
DOI: IEB authors: Miroslav Strnad, Danuše Tarkowská