Four new 26-aminocholestane-type glycosides from Solanum abutiloides

From the fresh roots of Solanum abutiloides, four new 26-aminocholesteryl glycosides were obtained, and their structures were characterized by analysis of their spectra data, including two-dimensional (2D) NMR spectroscopy. These compounds were regarded as key intermediates in the biogenesis of steroidal alkaloids.     

Cholestane glycosides from the bulbs of Galtonia candicans and their cytotoxicity

Further search for cytotoxic compounds contained in the bulbs of Galtonia candicans (Liliaceae) led to the isolation of four potent cytotoxic cholestane glycosides (1-4) based upon 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one, three of which (2-4) have not been reported previously. A new cholestane bisdesmoside (5) and a new rearranged cholestane glycoside (6) were also isolated. The structural assignment of the new constituents was carried out by spectroscopic analysis and a few chemical transformations.     

Steroidal glycosides from the underground parts of Solanum sodomaeum

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 human promyelocytic leukemia (HL-60) cells was investigated, and five compounds exhibited stronger activity than cisplatin.     

Steroid glycosides of Solanum tuberosum II. Tuberoside F

Institute of Ecological Genetics, Moldavian Academy of Sciences, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 730–731, September–October, 1991.     

Steroid glycosides from Solanum tuberosum seeds tuberosides C and D

Institute of Ecological Genetics of the Moldavian SSR, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 586–587, July–August, 1991.     

Two New Cholestane Bisdesmosides from Reineckia carnea

Three cholestane bisdesmosides, together with the corresponding aglycone, were isolated from the whole plant of Reineckia carnea. By detailed analysis of the 1D‐ and 2D‐NMR spectra, chemical methods, and comparison with spectral data of known compounds, the structures were determined to be (1β,3β,16β,22S)‐cholest‐5‐ene‐1,3,16,22‐tetrol ( 1 ), (1β,3β,16β,22S)‐cholest‐5‐ene‐1,3,16,22‐tetrol 1,16‐di(β‐D ‐glucopyranoside) ( 2 ), (1β,3β,16β,22S)‐cholest‐5‐ene‐1,3,16,22‐tetrol 1‐[O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranoside] 16‐(β‐D ‐glucopyranoside) ( 3 ), (1β,3β,16β,22S)‐cholest‐5‐ene‐1,3,16,22‐tetrol 1‐(β‐D ‐glucopyranoside) 16‐(3‐O‐acetyl‐β‐D ‐glucopyranoside) ( 4 ). Compounds 3 and 4 appeared to be new compounds, while compound 1 was isolated for the first from a natural source. Compound 2 was isolated from the genus Reineckia for the first time.     

Triterpene glycosides of alfalfa. III. Medicoside I

On the basis of chemical transformations and with the aid of physicochemical results, the structure of glycoside I isolated from the roots of the plantMedicago sativa has been established as hederagin 3-O-[O-α-L-arabinopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 2)-α-L-arabinopyranoside] 28-O-β-D-glucopyranoside. Compound (I), C₅₂H₈₄O₂₂, mp 210–212°C, [α] _D ²¹ +38.4° (c 1.48; methanol). Acid hydrolysis of (I) led to hederogenin (II) — C₃₀H₄₈O₄, mp 326–330°C, [α] _D ²³ +84.2° (c 0.19; pyridine. The Hakomorimethylation of glycoside (I) yielded the permethylate (IV) — C₆₅H₁₁O₂₂ [α] _D ²³ +41.6° (c 1.79; methanol). The GLC analysis of the products of the methanolysis of compound (IV) showed the presence of 3,4,6-tri-O-methyl-D-glucopyranose, 2,3,4,6-tetra-O-methyl-D-glucopyranose, 3,4-di-O-methyl-L-O-arabinopyranose, and 2,3,4-tri-o-methyl-L-arabinopyranose. The alkaline hydrolysis of glycoside I gave compound (III) with mp 230–233°C, [α] _D ²¹ +35.2° (c 0.21; methanol), which was identified as medicoside C. Details of the PMR spectrum are given for compound (IV) and of the IR spectrum for compound (I).     

Triterpene glycosides of alfalfa. III. Medicoside I

On the basis of chemical transformations and with the aid of physicochemical results, the structure of glycoside I isolated from the roots of the plantMedicago sativa has been established as hederagin 3-O-[O--L-arabinopyranosyl-(1 2)--D-glucopyranosyl-(1 2)--L-arabinopyranoside] 28-O--D-glucopyranoside. Compound (I), C₅₂H₈₄O₂₂, mp 210–212°C, [] _D ²¹ +38.4° (c 1.48; methanol). Acid hydrolysis of (I) led to hederogenin (II) — C₃₀H₄₈O₄, mp 326–330°C, [] _D ²³ +84.2° (c 0.19; pyridine. The Hakomorimethylation of glycoside (I) yielded the permethylate (IV) — C₆₅H₁₁O₂₂ [] _D ²³ +41.6° (c 1.79; methanol). The GLC analysis of the products of the methanolysis of compound (IV) showed the presence of 3,4,6-tri-O-methyl-D-glucopyranose, 2,3,4,6-tetra-O-methyl-D-glucopyranose, 3,4-di-O-methyl-L-O-arabinopyranose, and 2,3,4-tri-o-methyl-L-arabinopyranose. The alkaline hydrolysis of glycoside I gave compound (III) with mp 230–233°C, [] _D ²¹ +35.2° (c 0.21; methanol), which was identified as medicoside C. Details of the PMR spectrum are given for compound (IV) and of the IR spectrum for compound (I).Institute of the Chemistry of Plant Substances of the Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 607–610, September–October, 1986.     

Isolation of steroidal glycosides from Solanum xanthocarpum and studies on their antifungal activities

Isolation of the methanol extract of Solanum xanthocarpum resulted in the isolation and characterization of carpesterol (1) and four steroidal glycosides (2, 3, 4, and 5). The structures of these compounds were established by spectroscopic analysis. The antifungal activity of the steroidal compounds extracted from the fruits of S. xanthocarpum was investigated against Aspergillus niger and Trichoderma viride. The isolated compounds 1, 2, 3, 4, and 5 exhibited inhibitory effects on the radial growth of A. niger and Trichoderma viride.     

Triterpene glycosides ofHedera helix III. Structure of the triterpene sulfates and their glycosides

From the leaves of English ivyHedera helix L. we have isolated the known 3-sulfates of oleanolic and echinocystic acids and their 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters and the new 3-sulfate of 28-O--gentiobiosyl oleanolate — helicoside L-8a. The structures of the compounds isolated were deduced from the results of chemical transformations and NMR spectroscopy.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 87–90, January–February, 1999.     

Structure elucidation and complete NMR spectral assignments of new furostanol glycosides from Solanum torvum

Two new furostanol glycosides, torvosides O (1) and P (2), were isolated from leaves of Solanum torvum. Their structures were completely and unambiguously assigned by one‐ and two‐dimensional NMR techniques (¹H NMR, ¹³C NMR, TOCSY, HSQC, ROESY and HMBC), ESI‐MS spectrometry and chemical methods. Copyright © 2009 John Wiley & Sons, Ltd.