Steroidal Glycosides from the Underground Parts of Solanum sodomaeum

Abstract

Solanum sodomaeum L. is a solanaceous plant native to wide areas of the Libyan desert. In a previous paper, the antineoplastic activity of the mixture of glycoalkaloids extracted from the fruits of S. sodomaeum L. against Sarcoma 180 in mice was reported.1) The glycoalkaloids extracted from the fruits, leaves and stems of this plant were investigated using MS and HPLC analyses, and solamargine and solasonine were identified in all the plant materials.2) Furthermore, it was reported that a cream formulation containing purified glycoalkaloids from the fruits of the title plant was effective in the treatment of malignant human skin tumours; basal cell carcinomas, squamous cell carcinomas and benign tumours; keratoses and keratoacanthomas.3) Regarding another constituents of the fruits of S. sodomaeum L., two new pyrrole alkaloids were studied. 4) Here we describe the isolation and structural elucidation of a new steroidal glycoside from the underground parts of S. sodomaeum L., along with seven known steroidal glycosides, one of whose structures was corrected. Additionally, we report their antiproliferative activity against human promyelocytic leukemia (HL-60) cells.The MeOH extract of the underground parts of S. sodomaeum L. was successively subjected to Diaion HP20, silica gel, Sephadex LH20 and Chromatorex ODS column chromatographies, as well as HPLC on ODS, to afford eight steroidal glycosides (1-8).Compounds 3-8 were identified as solamargine (3),7) and protodioscin (8), 9) respectively, based on their physical and spectral data.Compound 1 was obtained as an amorphous powder, and its positive FAB-MS showed [MϩNa] ϩ ion peak at m/z 1053. The molecular formula of 1 was determined to be C 51 C-NMR spectrum of the aglycone (Ag) moiety of 1 gave signals similar to those of 6, apart from the appearance of the signals due to one methoxyl carbon (d 55.6) and one hemiacetal carbon (d 103.1) and the lack of the signal due to one oxygenated methylene carbon. These NMR signals were assigned in detail with the aid of 1 H-1 H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser and exchange spectroscopy (NOESY) spectra. The HMBC correlations and the coupling constant value for H-26 of Ag (d, Jϭ8 Hz) indicated 1 to be a tetraglycoside of 26b-methoxy diosgenin as shown in Fig. 1. On acidic hydrolysis, 1 afforded D-glucose, L-rhamnose and D-xylose. Furthermore, the 13 C-NMR data of the Ag moiety and the sugar moiety were quite similar to those of (25R,26R)-26-methoxyspirost-5-en-3b-ol10) and xylosyl-b-solamarine, 11) respectively. Based on these data, 1 was defin- A new steroidal glycoside has been isolated from the underground parts of Solanum sodomaeum L., along with seven known steroidal glycosides. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence, and the structure of one known pregnane type glycoside was corrected. In addition, their antiproliferative activity against huma...

Curaderm<sup>BEC5</sup> for Skin Cancers, Is It? An Overview

“…In Vivo single dose studies in mice with the lethal Sarcoma 180 cells have similarly shown that the LD 50 and ED 50 resulted in a TI of 3.3. Figure 5 shows the lethal toxicity in normal untreated mice of single i.p.…”

“…Ex Vivo studies have demonstrated that BEC is effecttive against a wide spectrum of human cancers and that BEC is, in a dose dependent manner, selectively killing cancer cells without harming normal cells [11][12][13][14][15][16]32,34,47,[49][50][51][52]. Figure 4 illustrates the specificity of BEC on cancer cells and lack of effect on normal cells.…”

“…BEC [11][12][13][14][15][16][17][18][19][20][50][51][52][53]. Table 1 shows at what concentrations solamargine kills cancer cells and normal cells.…”

Five New Steroidal Glycosides from the Stems of Solanum sodomaeum

“…Additionally, we had reported on the antiproliferative activity of these eight steroidal glycosides against human promyelocytic leukemia (HL-60) cells. 5) As a continuation to this study, we now describe the isolation and structural elucidation of 5 new steroidal glycosides obtained from the MeOH extract of the stems of S. sodomaeum L., along with 12 known glycosides. In the process, the structure of one of these glycosides was corrected.…”

“…On acidic hydrolysis, 1 afforded L-rhamnose, D-xylose, and D-glucose, which were confirmed by optical rotation using chiral detection in HPLC analysis. The 1 H-and 13 C-NMR data of the sugar moiety and of the C-1-C-11 of the aglycone moiety of 1 were superimposable on those of 14, 5) indicating that the sugar chain attached to the b-hydroxyl group at C-3 of aglycone was identical to the sugar chain of 14. The stereochemistry at C-16, C-17, and C-20 of aglycone was defined on the basis of the nuclear Overhauser and exchange spectroscopy (NOESY) spectrum, in which key nuclear Overhauser effects (NOEs) were observed between respective protons, as shown in Fig.…”