Application of 13C nuclear magnetic resonance spectroscopy to chemistry of glycosides: Structures of paniculosides-I, -II, -III, -IV, and -v, diterpene glucosides of Stevia paniculata Lag.

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Abstract
From the aerial part of Stevia paniculata (Compositae), five new diterpene glucosides, named paniculosides I-V (5-9) were isolated. On comparison of 13C nuclear magnetic resonance spectra of these glucosides with those of the aglycones, ent-15α-hydroxykaur-16-en-19-oic acid (1) [as methyl ester (17)], ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid (2), ent-11α, 15α-dihydroxykaur-16-en-19-oic acid (3), and ent-16β, 17-dihydroxykauran-19-oic acid (4) as well as some model glucosides, paniculosides I-IV (5-8) can be formulated as β-glucopyranosyl ester of 1, 3, 2, and 4, respectively and paniculoside-V (9) can be represented by 15-O-β-glucopyranoside of 5.

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