A New Spirostanol Glycoside from Yucca aloifolia

Specialization in the yucca–yucca moth obligate pollination mutualism: A role for antagonism?

“…The importance of selective abscission in regulating moth larval loads within flowers is a testament to this dynamic (Pellmyr et al, 1996; Pellmyr and Leebens‐Mack, 1999; Marr and Pellmyr, 2003). One of the major overlooked aspects of this interaction, however, is the fact that yucca leaves, inflorescences, and seeds are chemically defended primarily by saponins, a class of amphiphilic glycosides that are bitter, soapy feeding deterrents (Bahuguna et al, 1991; Hostettmann and Marston, 1995; Zhang et al, 2008). The dry mass of seeds of some Yucca species can be up to 18% saponins (Wall and Fenske, 1961; Stohs and Obrist, 1975; Hostettmann and Marston, 1995) and at least two species, Y. schidigera and Y. gloriosa are grown commercially for this resource (Piacente et al, 2005; Skhirtladze et al, 2011).…”

Structure, Bioactivity and Analytical Methods for the Determination of Yucca Saponins

“…To date, 33 aglycones have been described as part of the saponins found in the Yucca genus [6,7,11,12,14,16,[18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37], including spirostanic and furostanic saponins (Figure 2).…”

“…In addition to glucose, 22 different sugar chains have been described in Yucca. These are linked to aglycones on the C-3 position [6,7,11,12,14,16,[18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37]. The chains described in this genus possess up to seven monosaccharides.…”

“…Ten of them have the same core, which consists of a β-D-galactopyranose and two β-D-glucopyranoses, to which β-D-glucopyranoses, β-D-xylopyranoses or α-L-ramnopyranoses are linked at different positions to form the actual polysaccharide. On the other hand, other polysaccharides, such as S4C [25], S4D [18], S5G [24] and S5H [26], which present structures that do not follow this pattern have also been described (Figure 8), however their characterization was carried out, in some cases, using the non-fully developed structural elucidation techniques that were available for saponins before the early 1990s. Hence, the sugar chains S4C, S5G and S5H were reported in different publications on the saponins present in Y. aloifolia [24][25][26].…”

“…On the other hand, other polysaccharides, such as S4C [25], S4D [18], S5G [24] and S5H [26], which present structures that do not follow this pattern have also been described (Figure 8), however their characterization was carried out, in some cases, using the non-fully developed structural elucidation techniques that were available for saponins before the early 1990s. Hence, the sugar chains S4C, S5G and S5H were reported in different publications on the saponins present in Y. aloifolia [24][25][26]. The structures of these saponins are very different from each other, which leads us to suspect errors in their identification.…”