Caucasicosides E–M, furostanol glycosides from Helleborus caucasicus

Novel Steroidal Glycosides from the Whole Plants of <i>Helleborus foetidus</i>

“…Plants from the genus Helleborus are perennials belonging to the Ranunculaceae family, and are widely distributed throughout Europe. 1) Helleborus species are poisonous plants and a series of bufadienolides have been isolated from H. caucasicus, 2,3) H. odorus, 4,5) H. thibetanus, [6][7][8] and H. torquatus. 9) Recently, various bufadienolides from H. orientalis and H. foetidus were isolated and identified, some of which showed significantly potent cytotoxic activity and induced apoptosis via a mitochondria dependent pathway in cultured tumor cells.…”

“…10,11) Because Helleborus species has been reported to concomitantly contain the glycoside derivatives of C 27 steroids (spirostanols and furostanols), [12][13][14][15][16][17][18] further phytochemical examination of the methanolic extract of H. foetidus was performed using whole plants with a specific focus on steroidal glycosides. The isolation of 28 steroidal glycosides , including 20 novel spirostanol glycosides (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) and a novel furostanol glycoside (21) was achieved. The structures of the newly identified compounds were determined from their two-dimensional NMR spectra and hydrolytic cleavage.…”

Steroidal Saponins from the Rhizomes of Smilacina henryi

“…Full assignments of the H-and C-atoms of the aglycone (Tables 1 and 2) were achieved based on the combined analysis of 1 H-and 13 C-NMR, COSY, DEPT, HSQC, HMBC, TOCSY, and NOESY data. The C(25) configuration was deduced as (S) on the basis of NOESY cross-peaks d(H) 1.02 (Me(27))/d(H) 1.90 (H a ÀC(23)), d(H) 1.31 (H b ÀC(24))/d(H) 3.24 (H b ÀC(26)) [11] and of the difference of chemical shifts of the CH 2 (26) protons, i.e., d(H) 4.00 (H a ÀC(26)) and d(H) 3.24 (H b ÀC(26)) [12]. Besides, the C-atom resonances related to ring F, d(C) 26.8 (C(23)), d(C) 26.0 (C(24)), d(C) 27.7 (C(25)), d(C) 65.4 (C(26)), and d(C) 16.5 (C(27)), verified the (25S) configuration [13].…”