A new ergostanol saponin from Dioscorea deltoidea Wall var. orbiculata

Abstract

From the fresh rhizomes of Dioscorea deltoidea Wall var. orbiculata, a novel ergostanol saponin, orbiculatoside A (1), was isolated and identified as 3-O-beta-D-glucopyranosyl-ergost-5-ene-3beta, 26-diol-26-O-beta-D-glucopyranosyl(1-->3)-[beta-D-glucopyranosyl(1-->2)-beta-D-glucupyranosyl(1-->6)]-beta-D-glucopyranoside by various NMR techniques in combination with chemical methods. The new saponin showed strong activity against Pyricularia oryzae, with a MMDC (minimum morphological deformation concentration) value of 28.04 micromol/l and was cytotoxic to cancer cell line K562, HCT-15, A549, HT1080, and A2780a in vitro.

The Dioscorea genus: a review of bioactive steroid saponins

“…These saponins presented mainly a 25(R) position (1-18, 20, 21, 26-30), or a 25(S) (22)(23)(24)(25). About the E ring, a satured one can be found (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12), or with insaturations in the positions 20 (22) (13)(14)(15)(16)(17)(18) or 22 (23) on the open F ring (26). A seco-furostane skeleton is equally described (27)(28)(29)(30).…”

“…Moreover, in the same plant, pairs of furostanol saponins can be found constituted by the native molecule and its methyl derivative, like protoneodioscin (24) and Me protoneodioscin (25), protogracillin (3) and Me protogracillin (4), protoneogracillin (22) and Me protoneogracillin (23), from D. futschauensis. The methyl derivative may be described as an artifact [14]. In the same way, furostanol glycosides and their spirostanol analogs are sometimes isolated from the same plant as protodioscin (7) and dioscin (32) from D. futschauensis, D. panthaica, and D. villosa, asperoside (1) and parrisaponin (33) from D. cayenensis, protogracillin (3) and gracillin (34) from D. futschauensis and D. spongiosa, parvifloside (9) and 37, and deltoside (11) and deltonin (38) from D. parviflora.…”

“…hypoglauca [8][9][10][11][12][13], D. deltoidea var. orbiculata [14], D. futschauensis [15][16][17][18][19][20], D. nipponica [21], D. panthaica [22][23][24], D. parviflora [25], D. polygonoides [26,27], D. pseudojaponica [28], D. spongiosa [29], D. villosa [30], and D. zingiberensis [31] (Table 1). The structures of the aglycons of the isolated saponins belonged to three skeleton types: furostane, a pentacyclic ABCDE-ring system with a sixth open F ring (1-30); spirostane, a hexacyclic ABCDEF-ring system (31)(32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42)(43)(44)(45)(46); and pregnane, a tetracyclic ABCD-ring system (47-58) (Figs.…”

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

“…In the first-order APCI mass spectra, saponin G yielded an intense proton adduct ion 76 and orbiculatoside B 75 are isomers whose molecular weight is 884 Da. To identify its structure, APCI-MS/MS experiment was carried out.…”

Plant Growth–A Note on the Vegetative Growth in Dioscorea deltoidea

“…orbiculata was isolated via bioactivity-guided fractionation, the compound being identified as isonarthogenin [19].…”