Cytotoxic Oleanane-Type Triterpenoid Saponins from the Rhizomes of Anemone rivularis var. flore-minore

Abstract

Phytochemical investigation of the n-BuOH extract of the rhizomes of Anemone rivularis var. flore-minore led to the isolation of five new oleanane-type triterpenoid saponins 1-5, together with five known saponins 6-10. Their structures were determined by the extensive use of 1D and 2D NMR experiments, along with ESIMS analyses and acid hydrolysis. The aglycone of 4 and 5 was determined as 21α-hydroxyoleanolic acid, which was reported in this genus for the first time. The cytotoxicity of these compounds was evaluated against four human cancer cell line, including HL-60 (promyelocytic leukemia), HepG2 (hepatocellular carcinoma), A549 (lung carcinoma) and HeLa (cervical carcinoma). The monodesmosidic saponins 6-8 exhibited cytotoxic activity toward all tested cancer cell lines, with IC 50 values in the 7.25-22.38 μM range.

New triterpenoidal saponins from Koelreuteria paniculata

“…2) showed a set of correlations which confirmed the attachment of sugars in three positions of the aglycone; the correlation of the proton resonated at δ 5.09 (H-1‵) with the carbon signal resonated at δ 81.7 (C-3) confirmed the attachment of xylose-1 to C-3 of hederagenin, while the correlation of the proton resonated at δ 5.01 (H-1‵‵‵‵) with the carbon signal resonated at δ 64.7 (C-23) confirmed the attachment of glucose-1 to C-23 of hederagenin, and the correlation of the proton resonated at δ 6.24 (H-1‵‵‵‵‵) with the carbon signal resonated at δ 177.3 (C-28) confirmed the attachment of glucose-2 to C-28 of hederagenin. The down-fielded carbon signals at δ 76.2 and at δ 83.3 for both of C-3‵ of xylose-1 and C-3‘‵ of rhamnose-1 moiety respectively, confirmed that the C-3‵ positions for both sugars are attached to another sugar moieties, as well as the HMBC correlations of protons resonated at δ 6.33 (H-1‵‵) and at δ 5.35 (H-1‵‵‵) with the carbon signal resonated at δ 83.3 (C-3‵‵) confirmed the attachment of xylose-2 to rhamnose-1 was by C-3‵ of rhamnose-1 (Borges et al, 2009; Wang et al, 2014). The up-fielded carbon signals at δ 73.2 and 74.5 for C-3‵ and C-4‵ of rhamnose-2, confirmed that the rhamnose-2 is terminal and not attached to another sugars (Wang et al, 2014).…”

Triterpenoid Saponins from Anemone rivularis var. Flore-Minore and Their Anti-Proliferative Activity on HSC-T6 Cells

“…The gypsogenin aglycone saponins ( 1 and 2 ) and monodesmosidic ones ( 6 and 7 ) were inactive, which suggested that the aldehyde functional group at C-23 and the free carboxyl functional group at C-28 had negative effects on anti-proliferative activity (Figure 3). It is worth mentioning that the monodesmosidic saponins (the sugar chain attached at C-3 and a free carboxylic acid at C-28) were cytotoxic against tumor cells in previous studies [10,14,15,17]. These opposing effects may be due to their different mechanisms against different types of cells.…”

“…The assignments of the NMR signals of the aglycone moiety were derived from 1 H- 1 H COSY, TOCSY, HSQC, HMBC, and NOESY spectra (Table 1). The aglycone of 1 was thus elucidated as gypsogenin [17,18,19]. The 13 C-NMR shifts of C-3 at δ C 81.9 and C-28 at δ C 176.6 implied that sugar linkages were at both C-3 and C-28.…”

“…[9]. As part of our continuing study to explore bioactive natural products from the genus Anemone [10,11,12,13,14,15,16,17], we continued the investigation of this plant. In our present study, five new triterpenoid saponins ( 1 – 5 ), together with eight known ones ( 6 – 1 3 ) (Figure 1) were isolated, among which lupane-type saponins ( 3 and 12 ) were first reported from the Anemone genus.…”

Two new triterpenoid saponins from the aerial parts ofAnemone taipaiensis

“…Several species of this genus, such as A. flaccida, A. raddeana, A. tomentosa, A. anhuiensis, and A. altaica, have been used as Chinese folk medicines for a long time [1,2]. Anemone taipaiensis is an endemic species in Shaanxi Province of China and the rhizomes of this plant have been used for the treatment of rheumatism and phlebitis [3].…”