NMR spectroscopy of steroidal sapogenins and steroidal saponins: An update

Abstract

The I3C NMR chemical shifts of 126 steroidal sapogenins published between 1983 and 1993 are listed and critical spectral features and advances made in the NMR characterization of these compounds are discussed as a guide for the identification of the parent skeleton and the determination of substitution patterns. The NMR spectroscopic methods applicable to deduce the complete structure of the oligosaccharide moiety and its linkage to the sapogenin residue are also presented to elucidate the structure of steroidal saponins.

ESI‐QqTOF‐MS/MS and APCI‐IT‐MS/MS analysis of steroid saponins from the rhizomes of Dioscorea panthaica

“…14 In addition, the site at which one sugar is attached to another sugar of a saponin can readily be determined by 13 C NMR spectroscopy, and this is perhaps the most significant information contained in the spectrum, which is difficult to obtain by other methods. 15 For workers engaged in the study of bioactive constituents of medicinal plants, one of the most time-consuming steps is the structural elucidation of saponins, after the extraction and isolation of effective components. Although NMR spectral analysis can give much structural information on saponins, it needs purification of the samples.…”

Two New Cytotoxic Spirostane‐Steroidal Saponins from the Roots of Bletilla striata

“…The broad singlet at d(H) 4.66 in the 1 H-NMR spectrum revealed the b-orientation for HÀC(1) [15], since an a-oriented H-atom at C(1) reportedly appears as a double doublet (J ¼ 12.0, 2.0) [16]. This was further confirmed by the cross-peak between HÀC(1) and HÀC (19) in the ROESY spectrum (Fig. 3).…”

Steroidal Sapogenins and Glycosides from the Fibrous Roots of <i>Ophiopogon japonicus</i> and <i>Liriope spicata</i> var. <i>prolifera</i> with Anti-inflammatory Activity

“…The respective EtOAc and n-BuOH parts were loaded on silica gel, Sephadex LH-20, and octadecyl silica (ODS) silica gel to afford compounds 1-34, including five new steroidal saponins (1, 2, 18-20). The twenty nine known compounds were identified as ruscogenin (3), 11) ophiopogonin D (4), 12) ophiopogonin B (5), 12) 15) ophiopogonin D′ (11), 16) ophiogenin (12), 17) 18) prazerigenin A (15), 19) 11) Glycoside B (27), 11) 25(S)- 9) neoruscogenin (31), 22) 8) respectively, by comparison of spectrometric data with the literature (Fig. 1 24) as well as signal at δ H 5.20 (1H, br s, H-6) for an olefinic proton.…”

“…As part of our systematic study on steroidal constituents with biological activities from the fibrous roots of O. japonica and L. spicata var. prolifera, a total phytochemical fractionation led to the isolation of a series of steroidal constituents including two new steroidal saponins (1, 2), eleven known steroidal saponins along with five known steroidal sapogenins from O. japonica, and three new steroidal saponins (18)(19)(20), together with twelve known steroidal saponins and two known steroidal sapogenins from L. spicata var. prolifera.…”