Five megastigmane glucosides were isolated from the leaves of Glochidion zeylanicum. One of them was a known compound, blumenol C O-beta-D-glucopyranoside (1), and the structures of the four new compounds, glochidionionosides A-D (2-5), were mainly elucidated by spectroscopic methods, including a modified Mosher's method. The absolute configurations of the six-membered ring of glochidionionoside D (5) were deduced by beta-D-glucopyranosylation-induced shift trends in the (13)C-NMR spectra and confirmed by X-ray analysis as its p-bromobenzoate (5b), and the axis chirality of C-7 was determined to be R.
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Otsuka et al. (2003) studied this question.
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