- Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives
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Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of α-l-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was important to enhance cytotoxicity, and introducing more sugar residues at C3-OH of compound 12 with C-28 carboxylic acid is a favorable modification to ameliorate the anticancer activity. Furthermore, α-l-rhamnosyl moiety linked to C2-OH of the first monosaccharide (α-l-alabinose, β-d-xylose, β-d-galactose or β-d-glucose) in C3-OH of oleanolic acid was helpful to improve the cytotoxicity. According to the predicted log P values, lipophilicity of the synthesized saponins was not an important factor for cytotoxicity.
- Liu, Qingchao,Liu, Hongchun,Zhang, Lei,Guo, Tiantian,Wang, Peng,Geng, Meiyu,Li, Yingxia
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- TRITERPENE GLYCOSIDES AND THEIR GENINS FROM Thalictrum foetidum. I. THE STRUCTURE OF FOETOSIDE C
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A new glycoside - foetoside C - has been isolated from the epigeal part of Thalictrum foetidum L. and, on the basis of chemical transformations and spectral characteristics its structure has been established as oleanolic acid 28-6)-O-β-D-glucopyranoside> 3-O-3)-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside>.
- Ganenko, T. V.,Isaev, M. I.,Gorovits, T. T.,Gromova, A. S.,Lutskii, V. I.,et al.
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p. 433 - 438
(2007/10/02)
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- SELECTIVE CLEAVAGE OF ESTER TYPE GLYCOSIDE-LINKAGES AND ITS APPLICATION TO STRUCTURE DETERMINATION OF NATURAL OLIGOGLYCOSIDES
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On treatment with anhydrous LiI, 2,6-lutidine and anhydrous methanol, an ester type glycosyl linkage of acidic tri- and di-terpenes was selectively cleaved without decomposition of a reducing terminal of the resulting sugar moiety to give an anomeric mixture of methyl glycosides along with an aglycone or a pro-aglycone in quantitative yield.In this reaction, no hydrolysis of any other glycoside linkages took place.
- Ohtani, Kazuhiro,Mizutani, Kenji,Ryoji, Kasai,Tanaka, Osamu
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p. 4537 - 4540
(2007/10/02)
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