Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity

Abstract

Phytochemical examination of Convallaria majalis (Liliaceae) whole plants yielded 15 steroidal glycosides (1–15), including nine new compounds (4–6, 10–15) with a lycotetrose unit. The structures of the new compounds were determined using two-dimensional Nuclear magnetic resonance (NMR) analyses and chemical methods. The isolated compounds were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and HSC-4 and HSC-2 human oral squamous cell carcinoma cell lines. Of these, (25S)-spirost-5-en-3β-yl O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (1) exhibited cytotoxic activity against HL-60, A549, HSC-4, and HSC-2 cells with IC50 values ranging from 0.96 to 3.15 μM. The corresponding furostanol glycoside of 1, (25S)-26-[(β-d-glucopyranosyl)oxy]-22α-hydroxyfurost-5-en-3β-yl O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (8), was cytotoxic to the adherent cell lines of A549, HSC-4, and HSC-2 cells with IC50 values of 2.97, 11.04, and 8.25 μM, respectively. The spirostanol lycotetroside (1) caused necrotic cell death in A549 cells in a dose-dependent manner. Alternatively, the furostanol lycotetroside (8) induced apoptotic cell death in A549 cells in a time-dependent manner, as was evident by morphological observations and flow cytometry analyses.

Allelopathic Activity of a Novel Compound, 5,6-Dihydrogen-11α-O-acetyl-12β-O-tigloyl-17β-marsdenin, and a Known Steroidal Glycoside from the Leaves of Marsdenia tenacissima (Roxb.) Moon

“…According to previously reported data [42], our two isolated compounds (steroidal glycosides 1 and 2) belong to a group of C 21 steroidal glycosides. Although a wide range of pharmacological activities (including cytotoxic, anticancer, anti-inflammatory, and antitumor) of different C 21 steroidal glycosides have been documented [37,[43][44][45][46][47], no allelopathic activities of C 21 steroidal glycosides have been reported until now. Thus, this report is the first on the allelopathic activity of steroidal glycosides 1 and 2 from M. tenacissima leaves.…”

“…1 H and13 C-NMR data of compound 1 in CD 3 OD. Measured at 400 MHz.The molecular structure of compound 2 was determined as C45 H 70 O 15 by using HR-ESIMS at m/z 873.4659 [M + Na] + (calcd for C 45 H 70 O 15 Na 873.4612) (Figure…”

Spirostanol Sapogenins and Saponins from Convallaria majalis L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling

“…Figure 2 illustrates the mean RANK value calculated for diols, tetrols and pentols. An earlier study of steroidal glycosides from Convallaria majalis showed that the introduction of polar substituents to the steroidal nuclei resulted in reduced cytotoxicity [ 32 ]. Our docking results suggest that diols (less polar) have a higher affinity to the analyzed targets than tetrols and pentols (more polar).…”

Lycoperoside H, a Tomato Seed Saponin, Improves Epidermal Dehydration by Increasing Ceramide in the Stratum Corneum and Steroidal Anti-Inflammatory Effect

“…3 was purified by reversed-phase HPLC (Cosmosil 5C 18 -MS-Ⅱ, 20 φ × 250 mm) with 50% MeOH–1% acetic acid to obtain astragalin ( 9 , 31.0 mg, 0.0247%), rutin ( 10 , 10.0 mg, 0.0080%), and quercetin 3- O -β-cellobioside ( 11 , 14.6 mg, 0.0112%). The chemical structures of the isolated compounds were identified by a comparison of the 1 H- and 13 C- NMR spectra with References [ 2 , 19 , 20 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ]. The chemical structures of the isolated compounds ( 1 – 11 ) are shown in Figure 1 .…”