Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica

Abstract

Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1–11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.

An integrative taxonomic approach reveals a new species of Eranthis (Ranunculaceae) in North Asia

“…However, data on the significance of these substances for the taxonomy of Eranthis is still insufficient. Only a few studies of the phytochemical characteristics of certain Eranthis species, considered as medicinal plants, have been published (Djafari et al 2018;Hao 2018;Watanabe et al 2003Watanabe et al , 2019.…”

Novel Oleanane-Type Triterpene Glycosides from the Saponaria officinalis L. Seeds and Apoptosis-Inducing Activity via Mitochondria

“…During our ongoing phytochemical investigations of higher plants with a focus on new cytotoxic constituents, we have isolated cytotoxic triterpene glycosides from Dolichos lablab [1], Stryphnodendron fissuratum [2], Eranthis cilicica [3], Larrea tridentata [4], Anemone hupehensis var. japonica [5], Caulophyllum thalictroides [6], and Clematis chinensis [7].…”

“…In our phytochemical investigation of S. officinalis seeds, we focused on triterpene glycosides and isolated 17 glycosides (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17), including seven new ones (1)(2)(3)(4)(5)(6)(7). The structures of 1-7 were elucidated based on extensive analyses of NMR spectroscopic data, and chromatographic and spectroscopic analyses following chemical transformations.…”

Investigation of Chemical Constituents of Eranthis longistipitata (Ranunculaceae): Coumarins and Furochromones

“…Species of this genus have rarely been the subject of phytochemical research. Examination of the literature indicates that triterpene glycosides and saponins have been studied (along with their biological activity) in E. cilicica Schott & Kotschy [ 8 , 9 ]. The set of flavonoids has been investigated in E. sibirica DC., E. stellata Maxim., E. longistipitata Regel., and E. tanhoensis Erst [ 10 , 11 ].…”