Cholestane steroid glycosides from the rhizomes of Dioscorea villosa (wild yam)

Abstract

Phytochemical investigation of the MeOH extract of Dioscorea villosa root resulted in the isolation of two new bidesmosidic cholestane steroid glycosides, dioscoreavillosides A and B (1 and 2). In addition, the extract yielded 12 previously known furostane and spirostane steroid glycosides (3-14), along with diosgenin (15). Compounds 3-7, 9, 14, and 15 were isolated for the first time from D. villosa. The structures of the isolated compounds were determined using spectroscopic and chemical methods including 1D and 2D NMR. The antimicrobial action of most of these compounds was tested against five fungal and five bacterial strains.

Characterization of Steroidal Saponins from Dioscorea villosa and D. cayenensis Using Ultrahigh Performance Liquid Chromatography/Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry

“…Under the developed chromatographic conditions, the retention times of compounds 1 and 2 (cholestane-type compounds) were found to be 3.01 and 4.3 min, compounds 3-9 (furostan-type saponins) were found to be 3.61, 3.96 . So, compound 7 was identified as huangjiangsu A, which had been isolated from D. villosa [31]. The fragment ion at m/z 885.48 resulted from the loss of a hexose as the terminal unit [M -Glu + H] + .…”

“…Compounds 10 and 14 were chosen as an example to discuss the fragmentation patterns for these saponins in detail. Compound [15,31]. The elimination of 144 Da (formula C 8 H 16 O 2 ) might be produced by cleavage of the E-ring of the aglycone [23,31], and the 18 Da unit was derived from the loss of a molecule of water.…”

Evaluation of wild yam (Dioscorea villosa) root extract as a potential epigenetic agent in breast cancer cells

“…The methanolic extract of the authenticated dried root powder of D. villosa L (NCNPR code #9800) was obtained from the National Center for Natural Products Research (NCNPR), University of Mississippi (Ali et al 2013). Chromatographic profiling (UHPLC-QToF-MS) of the root extract is presented in supplementary Figure 1.…”

“…The components of wild yam root extract (WYRE) belonging to steroidal saponins and sapogenins are found to be noncarcinogenic (Hooker 2004). To our knowledge, 14 steroidal saponins, 2 flavan-3-ol glycosides, and 14 diarylheptanoids have been reported from wild yam (Sautour et al 2006;Dong et al 2007;Hayes et al 2007;Yoon et al 2010;Ali et al 2013); among them diosgenin and dioscin exhibit anticancer activity (Jagadeesan et al 2012). WYRE was able to reduce cell proliferation, increase the expression of progesterone receptor and pS2 mRNA and down regulate ERα protein (Park et al 2009).…”

Chemical fingerprint analysis and quantitative determination of steroidal compounds from Dioscorea villosa, Dioscorea species and dietary supplements using UHPLC‐ELSD

“…The steroidal saponins, parvifloside ( 1 ), protodeltonin ( 2 ), protobioside ( 4 ), huangjiangsu A ( 5 ), pseudoprotodioscin ( 6 ), 26‐ O‐β ‐ d ‐glucopyranosyl‐3 β ,26‐diol‐25( R )‐furost‐5,20(22)‐dien‐3‐ O‐α ‐ l ‐rhamnopyranosyl(1 → 2)‐ O‐β ‐ d ‐glucopyranoside ( 7 ), zingiberensis saponin I ( 8 ), deltonin ( 9 ), dioscin ( 10 ) and progenin III ( 11 ) were isolated at the National Center for Natural Products Research (NCNPR, University of Mississippi, University, MS, USA). The identity and purity of these compounds was confirmed by chromatographic (TLC, UHPLC) methods and the analysis of the spectral data (IR, 1D‐ and 2D‐NMR, ESI‐HRMS), as well as comparison with published spectral data (Munafo et al ., ; Yoshikawa et al ., ; Shao et al ., ; Dong et al ., ; Wang et al ., ; Shen et al ., ; Silva et al ., ; Hu et al ., ; Zheng et al ., ; Ali et al ., , ). The purity of these compounds was found to be >90%.…”