Chem. Pharm. Bull. 54(2) 230—233 (2006)
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چکیده
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. 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. 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. Regarding another constituents of the fruits of S. sodomaeum L., two new pyrrole alkaloids were studied. 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), pregna-5,16-dien-3b-ol-20-one 3-O-a-L-rhamnopyranosyl(1→2)-[a -L-rhamnopyranosyl-(1→4)]-b -D-glucopyranoside (4), diosgenin 3-O-b-solatrioside (5), dioscin (6), indioside D (7) and protodioscin (8), respectively, based on their physical and spectral data. Compound 1 was obtained as an amorphous powder, and its positive FAB-MS showed [M Na] ion peak at m/z 1053. The molecular formula of 1 was determined to be C51H82O21 by high-resolution (HR) positive FAB-MS. The H-NMR spectrum of 1 showed signals due to two tertiary methyl groups (d 1.06, 0.83), four secondary methyl groups [d 1.76 (d, J 6.0 Hz), 1.56 (d, J 6.0 Hz), 1.14 (d, J 7.5 Hz), 0.96 (d, J 6.0 Hz)], one methoxyl group (d 3.52), one olefinic proton [d 5.34 (d like, J 5.0 Hz)], and four monosaccharide groups, two of which were considered to be rhamnosyl groups. The 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 H–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, J 8 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 C-NMR data of the Ag moiety and the sugar moiety were quite similar to those of (25R,26R)-26-methoxyspirost-5-en-3b-ol 3-O-{O-a -L-rhamnopyranosyl-(1→2)-O-[b -D-glucopyranosyl-(1→4)]-b-D-glucopyranoside} and xylosyl-b-solamarine, respectively. Based on these data, 1 was defined as (25R,26R)-26-methoxyspirost-5-en-3b-ol 3-O-{O-a-Lrhamnopyranosyl-(1→2)-O-[b-D-xylopyranosyl-(1→2)-O-aL-rhamnopyranosyl-(1→4)]-b-D-glucopyranoside}, which is tentatively named solasodoside A.
منابع مشابه
Antiinflammatory Constituents of Teramnus labialis
1. Alagarsamy, V., Raja Salomon, V., Vanikavitha, G., Paluchamy, V., Ravichandran, M., Arnold Sujin, A., Thangathirupathy, A., Amuthalakshmi, S. and Revathi R., Biol. Pharm. Bull., 2002, 25, 1432. 2. Alagarsamy, V., Muthukumar, V., Pavalarani, N., Vasanthanathan, P. and Revathi R., Biol. Pharm. Bull., 2003, 26(4), 557. 3. Chaurasia, M.R. and Sharma, S.K., Arch. Pharm., 1982, 315, 377. 4. Manabu...
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تاریخ انتشار 2006