Saponarioside

Jia Z, Koike K, Nikaido T (1999) Saponarioside C, the First a-D-Galactose Containing Triterpenoid Saponin, and Five Related Compounds from Saponaria officinalis. J Nat Prod 62 449... 

Fig. (2). The HOHAHA spectrum (tm = 150 ms) for the sugar moiety of saponarioside C from Saponaria officinalis showing the sub-spectra corresponding to each anomeric proton. Note that for the glucose (G, G G") and xylose (X) units, the correlations were observed from the anomeric protons till terminals. However, the correlation stopped at H-4 of the galactose (G" ) moiety due to the small coupling between H-4 and H-5. Spectrum measured at 500 MHz in pyridine-. ...

Fig. (3). Phase-sensitive NOESY spectrum of saponarioside C from Saponaria officinalis (the mixing time was 600 msec). Note that both the inter-residue (bold labeled) and intra-residue NOEs were observed. For the a-D-galactose moiety, the only intra-residue NOE noted is between H, and H2. For all other sugar units, the intra-residue NOEs between H,/H3 and H,/H5 are observed.

This has been found to be of wide applicability for the structure determination of the naturally occurring glycosides. An example of a NOESY spectrum is given in the section on the structural study of saponarioside C isolated from Saponaria officinalis (Fig. 3) [21]. Both the inter-residue NOEs and the intra-residue NOEs were observed. 

The MeOH extract of the freshly collected whole plant of S. officinalis was suspended in water and partitioned successively with EtOAc and n-BuOH. The aqueous part, on chromatography over Diaion HP-20 followed by repeated MPLC and HPLC purification afforded two major triterpenoid saponins, saponariosides A and B. Similarly, the -BuOH soluble fraction afforded six triterpenoid saponins designated as saponariosides C-H. Investigation of the plant material collected from different geographical locations led to the isolation of previously reported saponariosides C, E, F and G along with five more new saponins, saponariosides I-M (Fig. 7), from which two new sapogenins have been characterized as VIII and XII (Fig. 1). However, saponarioside D, the major constituent of the -BuOH soluble fraction as reported previously by us [21], could not be detected. 

Fig. (9). HOHAHA (im=150 ms) spectra (part) of saponarioside A (500 MHz in pyridine-rf5) showing the subspectra corresponding to each anomeric proton (upper) and methyl group (lower). Note that the resonances for anomeric protons of E and F, G and H overlapped.

The data in this column were taken from saponarioside A. 

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