Biogenesis of cyclobuxine-D and cyclovirobuxine-D in Buxus sempervirens |
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Authors: | David Abramson Furn F Knapp LJohn Goad Trevor W Goodwin |
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Institution: | Department of Biochemistry, The University of Liverpool, Liverpool L69 3BX, U.K. |
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Abstract: | Two major alkaloids from Buxus sempervirens, cyclovirobuxine-D and cyclobuxine-D, were found to be radioactively labelled following administration of mevalonic acid 2-14C,(4R)-4-3H1] to freshly-harvested shoots. The 3H: 14C atomic ratio of 3:4 in cyclovirobuxine-D indicated a biosynthetic pathway from cycloartenol involving 3-ketone and 20-ketone intermediates. A 3H: 14C atomic ratio of ca 3:3 in cyclobuxine-D suggests that the 4α-methyl group of cycloartenol is lost in its formation, and this conforms with current theories of the sequence of C-4 demethylation of sterols. |
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Keywords: | Buxaceae boxwood biosynthesis steroidal alkaloids cyclovirobuxine-D cyclobuxine-D C-4 demethylation |
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