New Steroidal Glycosides from Rhizomes ofClintonia udensis

Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity

“…Compound 8 , which is the corresponding furostanol glycoside of 1 , was only cytotoxic to the adherent cell lines of A549, HSC-4, and HSC-2 cells, with IC 50 values of 2.97 ± 0.06 μM, 11.04 ± 0.25 μM, and 8.25 ± 0.20 μM, respectively ( Table 3 ). As we previously reported [ 11 , 12 ], the cytotoxicity of 1 compared to those of 2 , 4 , 5 , and 6 and of 8 compared to those of 9 and 10 indicated that the introduction of polar substituents to the steroidal nuclei resulted in reduced the cytotoxicity. Compound 1 was cytotoxic to tumor cells, whereas 3 , having the diglycoside did not show cytotoxic activity.…”

Four New Furostanol Saponins from the Rhizomes and Roots of Smilax scobinicaulis and Their Cytotoxicity

“…Thus, the α-configurations of H-17 and the methoxy at C-22 position were unambiguously deduced based on the strong NOE correlations of H-21/H-17 and H-21/OCH 3 . The 14α configuration was further confirmed by the NOE correlations of H-14/H-16 and H-16/OCH 3 [11]. However, the C-25 configuration of 1 was assigned as 25 R based on the observed difference (∆ ab = δ a − δ b = 0.35) of the 1 H-NMR chemical shifts of the H 2 -26 geminal protons, which was in agreement with that of 25 R furostane-type steroidal saponins (∆ ab < 0.48 for 25 R ; ∆ ab > 0.57 for 25 S ) [12].…”

“…The sugars were determined to be d -glucose and l -arabinose by acid hydrolysis of 1 and then trimethylsilylation and GC analysis on a chiral column in comparison with an authentic sample. Furthermore, the location of the glucopyranosyl was found to be C-26 of the aglycon on the basis of a glycosylation shift of C-26 at δ C 74.6 and the HMBC correlation peak between H-1''' of glucopyranosyl at δ H 4.26 and C-26 of the aglycone at δ C 74.6, which is a structural feature in plant furostanol saponins [11]. The attachments of sugar chain were deduced from the HMBC spectrum, in which the long range correlation between glc-H-1' at δ H 4.42 with C-3 at δ C 76.8 of the aglycone and ara-H-1'' at δ H 4.34 with C-6' at δ C 68.2 of the glucopyranosyl were observed (Figure 2), respectively.…”

Open-chain steroidal glycosides, a diverse class of plant saponins

“…17,46 All of these are D 24(25) unsaturated analogues of alliosterol glycosides that co-occur in the same plant species, specically of 40, 34, 37, and 50, respectively. The corresponding 5a aglycone, (22S)-1b,3b,16b,22-tetrahydroxy-5a-cholest-24-ene (65), is represented by four glycosides 66-69 isolated from O. thyrsoides. 39,45 Compounds 66 and 69 correspond to the 5a, D 24(25) -unsaturated analogues of alliosterol glycosides 34 and 40, respectively, while 67 and 68 correspond to the D 24 (25) -unsaturated versions of the 5a-alliosterol saponins 56 and 59, respectively.…”

“…Galtonia candicans), 17,46,138 Ruscus hypophyllum, 33 Allium jesdianum, 31 Polianthes tuberosa, 37 Cordyline terminalis, 107 and Clintonia udensis. 65 Though this is the most common bioactivity assay performed on open-chain plant glycosides, cytotoxicity against other human cancer cell lines has been assessed for saponins isolated from Dioscorea septemloba, 60,105 D. bulbifera, 73,74 Ornithogalum thyrsoides, 39 Allium nigrum, 29 A. macrostemon, 139 Tribulus macropterus, 75 Chamaelirium luteum, 23 Camassia leichtinii, 112 and Cestrum nocturnum. 116 Plant openchain saponins have also been evaluated for activity against mouse cancer cell lines, 38 as well as inhibition of cyclic AMP phosphodiesterase, 30,36,45,76,102 cyclooxygenase-2 (COX-2), 115 Review NPR sodium-potassium adenosine triphosphatase (Na + /K + -ATPase).…”