- Isolation and characterization of dioscin-α-l-rhamnosidase from bovine liver
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A novel dioscin-α-l-rhamnosidase was isolated and purified from fresh bovine liver. The activity of the enzyme was tested using diosgenyl-2,4-di-O- α-l-rhamnopyranosyl-β-d-glucopyranoside as a substrate. It was cleaved by the enzyme to two compounds, rhamnoses and diosgenyl-O-β-d- glucopyranoside. The optimal conditions for enzyme activity were that temperature was at 42 C, pH was at 7, reaction time was at 4 h, and the substrate concentration was at 2%. Furthermore, metal ions such as Fe 3+, Cu2+, Zn2+, Ca2+ and Mg 2+ showed different effects on the enzyme activity. Mg2+ acted as an activator whereas Cu2+, Fe3+, and Zn 2+ acted as strong inhibitors in a wide range of concentrations from 0 to 200 mM. It was interesting that Ca2+ played a role as an inhibitor when its concentration was at 10 mM and acted as an activator at the other concentrations for the enzyme. Moreover, the molecular weight of enzyme was determined as 75 kDa.
- Qian, Siriguleng,Wang, Hongying,Zhang, Chunzhi,Yu, Hongshan
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- STRUCTURE CHARACTERIZATION OF HAEMOSTATIC DIOSGENIN GLYCOSIDES FROM PARIS POLYPHYLLA
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Key Word Index - Paris polyphylla; Liliaceae; polyphyllin D; pariphyllin; yunnan paiyao; haemostatic and cytotoxic diosgenin glycosides. - From Paris polyphylla var. chinensis Hare (Liliaceae), four diosgenin glycosides with haemostatic effects were isolated.The structure of the major component was elucidated by chemical and spectroscopic methods as 3-(Rha -> 2Glu)>-Ara -> 4Glu)>-β-D-glucopyranosyl)-25(R)-spirost-5-en-3β-ol.This saponin was found to be identical to three previously reported compounds to which other structures were originally assigned, namely the major component from P. polyphylla Smith, the major cytotoxic component of yunnan paiyao, and polyphyllin D from P. polyphylla grown in the Himalaya region.
- Ma, James C. N.,Lau, F. W.
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- The microbiological transformation of steroidal saponins by Curvularia lunata
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The microbiological transformation of polyphyllin I (compound I), polyphyllin III (compound II), polyphyllin V (compound III) and polyphyllin VI (compound IV) by Curvularia lunata into their corresponding subsaponins, for example, diosgenin-3-O-α-l-arabinofuranosyl (1→4)-β-d- glucopyranoside (compound V), diosgenin-3-O-α-l-rhamnopyranosyl (1→4)-β-d-glucopyranoside (compound VI), diosgenin-3-O-β-d- glucopyranoside (compound VII) and pennogenin-3-O-β-d-glucopyranoside (compound VIII), were studied in this paper. Curvularia lunata is able to hydrolyze terminal rhamnosyls that are linked by 1→2 C- bond to sugar residues of steroidal saponins at C-3 position with high activity and regioselectivity.
- Feng, Bing,Ma, Bai-Ping,Kang, Li-Ping,Xiong, Cheng-Qi,Wang, Sheng-Qi
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- A biocatalytic synthesis of diosgenyl-β-d-glucopyranoside by the use of four recombinant enzymes in one pot
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A system for the one-pot synthesis of diosgenyl-β-d-glucopyranoside (trillin) using multiple recombinant enzymes is developed. The enzymes maltodextrin phosphorylase (E1), glucose-1-phosphate thymidylyltransferase (E2), inorganic pyrophosphatase (E3), and solanidine glucosyltransferase (E4) involved in the work have been cloned and expressed in Escherichia coli. Under the optimized reaction conditions, the yield of trillin reached 28% (ca. 15.8 mg/l). The recovery yield of trillin after purification was 89%.
- Dong, Qing,Ouyang, Li-Ming,Yu, Hui-Lei,Xu, Jian-He,Lin, Guo-Qiang
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- Small molecular weight PEGylation of diosgenin in an in vivo animal study for diabetic auditory impairment treatment
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Diosgenin was modified to control its in vivo bioavailability by conjugating a hydrophilic unit, tetraethylene glycol. The diosgenin- tetraethylene glycol conjugate (TE) was orally administered in streptozotocin induced diabetic mice for this auditory protection study. The bioactivity improvement of TE for in vivo diabetic auditory impairment treatment was clearly observed in three different auditory tests and compared with that of diosgenin. The improvement in in vivo efficacy suggests that the small molecular weight PEGylation of diosgenin is a synthetically robust and systematically applicable strategy to reform the poor pharmacokinetics of a hydrophobic aglycone.
- Kim, Dong-Hwan,Hong, Bin Na,Le, Hoa Thi,Hong, Ha Na,Lim, Choon Woo,Park, Keun Ha,Kim, Tae Woo,Kang, Tong Ho
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- The substrate specificity of a glucoamylase with steroidal saponin-rhamnosidase activity from Curvularia lunata
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In previous work, we studied and reported that an enzyme from Curvularia lunata 3.4381 had the novel specificity to hydrolyze the terminal rhamnosyl at C-3 position of steroidal saponin and obtained four transformed products; the enzyme was purified and ascertained as glucoamylase (EC 3.2.1.3 GA). In this work, the enzyme exhibiting steroidal saponin-rhamnosidase activity was systematically studied on 21?steroidal saponins and 6 ginsenosides. The results showed that the α-1,2-linked end-rhamnosyl residues at C-3 position of steroidal saponins could be hydrolyzed to corresponding secondary steroidal saponins, among which 18 compounds were isolated and identified, including 3 new secondary compounds. For the furostanosides having glucosyl residues at the C-26 position, hydrolysis occurred first at end-rhamnosyl at C-3 position to produce secondary furostanosides. The reaction of hydrolyzing glucosyl at C-26 position depended considerably on longer reaction times yielding the corresponding secondary spirostanosides (without rhamnosyl and glucosyl residues). The enzyme had the strict specificity for the terminal α-1,2-linked rhamnosyl residues of linear chain, or the terminal α-1,2-linked rhamnosyl residues with branched chain of 1,4-linked glycosyl residues of sugar chain at C-3 position of steroidal saponins, it was not specific for different aglycones, different glycons, and the number of glycon of sugar chain of steroidal saponin. The end-rhamnosyl of ginsenosides and p-nitrophenyl-α-l-rhamnopyranoside (pNPR) could not be hydrolyzed by the enzyme from C. lunata.
- Feng, Bing,Kang, Li-ping,Ma, Bai-ping,Quan, Bo,Zhou, Wen-bin,Wang, Yong-ze,Zhao, Yu,Liu, Yi-xun,Wang, Sheng-qi
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- Pathways of biotransformation of zingiberen newsaponin from Dioscorea zingiberensis C. H. Wright to diosgenin
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A new steroidal saponin-β-glucosidase from Aspergillus flavus that specifically hydrolyzed the terminal β-d-glucosyl group at the C-3 position of zingiberen newsaponin, deltonin and trillin from Dioscorea zingiberensis C. H. Wright (DZW) was purified, and characterized. The optimal temperature and pH for the new steroidal saponin-β-glucosidase was 50 C and pH 5.0. The steroidal saponin-β-glucosidase was stable at 30-60 C, and retained more than 80% activity. Further, the purified protein was analyzed by ESI-Q-TOF proteomic analyzer. The results indicated that this enzyme is a β-glucosidase of the type glycosidase hydrolase 3 (GH3). Using a combination of the steroidal saponin-β-glucosidase and steroidal saponin-α-1,2-rhamnosidase from Curvularia lunata obtained previously in our lab, the saponins zingieren newsaponin and deltonin could be converted to diosgenin. The pathways of converting zingiberen newsaponin and deltonin into diosgenin by the two key enzymes were elucidated in this study.
- Huang, Hongzhi,Zhao, Min,Lu, Li,Tan, Dawei,Zhou, Wenbin,Xiong, Chengqi,Zhao, Yang,Song, Xinbo,Yu, Liyan,Ma, Baiping
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- Purification and characterization of dioscin-α-L-rhamnosidase from pig liver
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Dioscin-α-L-rhamnosidase was isolated, purified and partially characterized from pig liver. The maximum activity was reached at pH 7, 42°C, 24 h, and 2% of substrate concentration. Fe3+ and Cu 2+ inhibited the enzyme; the ion Ca2+ activated it. Mg2+ was an inhibitor at 100 mM, but it was an activator at 200 mM. Zn2+ could be a weak activator of the enzyme. The molecular weight of dioscin-α-L-rhamnosidase was about 47 kDa as determined by the method of SDS-polyacrylamide gel electrophoresis.
- Qian, Srguleng,Yu, Hongshan,Zhang, Chunzhi,Lu, Mingchun,Wang, Hongying,Jin, Fengxie
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- STEROIDAL SAPONINS FROM THE BULBS OF TRITELEIA LACTEA AND THEIR INHIBITORY ACTIVITY ON CYCLIC AMP PHOSPHODIESTERASE
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The chemical compounds in the bulbs of Triteleia lactea have been analysed as a part of our systematic study of plants of the subfamily Allioideae in Liliaceae.Thirteen steroidal saponins, seven of which appeared to be new compounds, were isolated.The structures of the new saponins were elucidated on the basis of the spectroscopic analysis, including two-dimensional NMR techniques, and hydrolysis.Inhibitory activity of the isolated saponins on cyclic AMP phosphodiesterase was evaluated to identify new compounds with medicinal potential. - Key words: triteleia lactea; Allioideae; Liliaceae; bulbs; steroidal saponins; spirostanol saponins; cyclic AMP phosphodiesterase inhibition.
- Mimaki, Yoshihiro,Nakamura, Osamu,sashida, Yutaka,Nikaido, Tamotsu,Ohmoto, taichi
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- N-Pentenyl-Type Glycosides for Catalytic Glycosylation and Their Application in Single-Catalyst One-Pot Oligosaccharide Assemblies
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We have developed a new type of n-pentenyl-type glycosides that can be activated by catalytic amounts of promoter, Hg(NTf2)2 or PPh3AuCl/AgNTf2, at room temperature. The mild activation conditions and outstanding stability of common protection/deprotection manipulations enable the enynyl donors to have broad applications in constructing various glycosidic bonds. Furthermore, under the Hg(NTf2)2-catalyzed conditions, the sequential activation of different types of donors was achieved, based on which a gentiotetrasaccharide was synthesized via the newly developed single-catalyst one-pot strategy.
- Zu, Yujia,Cai, Chenglin,Sheng, Jingyuan,Cheng, Lili,Feng, Yingle,Zhang, Shengyong,Zhang, Qi,Chai, Yonghai
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supporting information
p. 8270 - 8274
(2019/10/14)
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- Novel steroid -based amphiphiles and uses thereof
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The present invention relates to a newly developed steroid-based amphiphilic compound, a preparation method thereof and a method for extracting, solubilizing, stabilizing, crystallizing or analyzing membrane proteins using the same. In addition, the compound, compared to the conventional compounds, can efficiently extract membrane proteins having various structures and properties from cell membranes and store the same in an aqueous solution for a long time, and thus can be used for functional analysis and structural analysis. Membrane protein structure and function analysis thereof is one of the areas of greatest interest in current biology and chemistry by being closely related to drug development.COPYRIGHT KIPO 2020
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Paragraph 0165; 0170-0171; 0173; 0185-0187; 0239-0241
(2020/05/23)
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- STEROID SAPONINS WITH ANTI-CANCER ACTIVITY
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The present invention relates to a new class of steroid saponins that have interesting biological activity. In particular the present invention relates to a class of steroid saponins in which the sugar moiety has been selectively functionalised to introdu
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- A kind of modified Fischer-type glycosidation reaction in constructing a saponin in the application of the glycosidic bond
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The invention belongs to the field of organic synthesis, and involves a synthesis method of saponin, and in particular a method to construct glycosidic bond in saponin. The method includes the following steps: directly reacting an excessive amount of aldose or ketose with aglycone in an appropriate organic solvent under the action of an acid catalyst and reflux temperature of 30 DEG C to obtain the target product of saponin.
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Paragraph 0034-0036
(2018/05/24)
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- Solasodine-3-O-β-D-glucopyranoside kills Candida albicans by disrupting the intracellular vacuole
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The increasing incidence of fungal infections and emergence of drug resistance underlie the constant search for new antifungal agents and exploration of their modes of action. The present study aimed to investigate the antifungal mechanisms of solasodine-3-O-β-D-glucopyranoside (SG) isolated from the medicinal plant Solanum nigrum L. In vitro, SG displayed potent fungicidal activity against both azole-sensitive and azole-resistant Candida albicans strains in Spider medium with its MICs of 32 μg/ml. Analysis of structure and bioactivity revealed that both the glucosyl residue and NH group were required for SG activity. Quantum dot (QD) assays demonstrated that the glucosyl moiety was critical for SG uptake into Candida cells, as further confirmed by glucose rescue experiments. Measurement of the fluorescence intensity of 2′,7'-dichlorofluorescin diacetate (DCFHDA) by flow cytometry indicated that SG even at 64 μg/ml just caused a moderate increase of reactive oxygen species (ROS) generation by 58% in C. albicans cells. Observation of vacuole staining by confocal microscopy demonstrated that SG alkalized the intracellular vacuole of C. albicans and caused hyper-permeability of the vacuole membrane, resulting in cell death. These results support the potential application of SG in fighting fungal infections and reveal a novel fungicidal mechanism.
- Chang, Wenqiang,Li, Ying,Zhang, Ming,Zheng, Sha,Li, Yan,Lou, Hongxiang
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p. 139 - 146
(2017/06/05)
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- IMPROVED SYNTHESIS
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The present invention provides an improved synthesis of a class of steroid saponins. Furthermore, the present invention provides a method of selectively discriminating between the C2 and C3 hydroxyl groups of a mono-glycosylated steroid saponin – a key step in the preparation of this class of compounds. Additionally, the present invention provides a range of steroid saponin derivatives, and methods of making them.
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- An improved synthesis of methyl protodioscin. II. A direct E-ring opening by BF3-Et2O/Ac2O from dioscin ester
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A direct E-ring opening of dioscin ester by BF3-Et 2O/Ac2O was studied, and methyl protodioscin was synthesized from dioscin ester in three steps with a total yield of 44%. The details of the E-ring opening reaction was di
- Wang, Bo,Liu, Yang,Liu, Xin,Cheng, Mao-Sheng
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p. 1015 - 1017,3
(2012/12/11)
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- Synthesis of novel spirostanic saponins and their cytotoxic activity
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This study was carried out to assess the cytotoxicity of several new synthetic steroidal saponins against the human myeloid leukemia cell lines (HL-60 and U937) and against human melanoma cells (SK-MEL-1). Several diosgenyl glycosides analyzed showed strong cell growth inhibition which was associated with alterations in cell cycle progression and induction of apoptosis. Studies of cytochrome c release and caspase-9 activation suggest a main role of the intrinsic pathway of apoptosis in the mechanism of cytotoxicity caused by this kind of compounds.
- Hernandez, Juan C.,Leon, Francisco,Brouard, Ignacio,Torres, Fernando,Rubio, Sara,Quintana, Jose,Estevez, Francisco,Bermejo, Jaime
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p. 2063 - 2076
(2008/09/21)
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- Synthesis and antitumor activity of icogenin and its analogue
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Natural saponin icogenin, namely 25(S)-22-O-methyl-furost-5-en-3β,26- dio-3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranoside, and one of its analogues, 25(S)-22-O-methyl-furost-5-en-3β,26-dio-3-O-α-l-rhamnopyranosyl-(1 → 2)-[
- Hou, Shujie,Xu, Peng,Zhou, Liang,Yu, Dequan,Lei, Pingsheng
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p. 2454 - 2458
(2007/10/03)
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- Facile sythesis of dioscin and its analogues
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Three representative spirostanol saponins that have typical structure of the sugar moiety, diosgenyl 2,3-di-O-α-L-rhamnopyranosyl-β-D- glucopyranoside, diosgenyl 2,4-di-O-α-L-rhamnopyranosyl-β-D- glucopyranoside (dioscin), and diosgenyl 2,6-di-O-α-L-rhamnopyranosyl- β-D-glucopyranoside, were synthesized in a facile way. An approach to selectively mask the C3-hydroxyl of diosgenyl 4,6-O-benzylidene β-D-glucopyranoside was described. A procedure using cerium(IV) ammonium nitrate for selective removal of tert-butyldimethylsilyl group while retaining levulinyl group is afforded. Copyright
- Hou, Shujie,Zou, Chuanchun,Zhou, Liang,Lei, Pingsheng,Yu, Dequan
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p. 1220 - 1221
(2007/10/03)
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- Glycosyl trifluoroacetimidates. 2. Synthesis of dioscin and Xiebai saponin I
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Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin I (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.
- Yu, Biao,Tao, Houchao
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p. 9099 - 9102
(2007/10/03)
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- A SULFATED GLYCOSIDE FROM THE PREPARATION "TRIBESTAN"
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The chemical composition and structures of the steroid glycosides forming the active principle of the preparation "tribestan", which is used for treating impotence and female infertility, have been studied.It has been shown that together with trillin, prosapogenin A of dioscin, trillarin, dioscin, gracillin, protodioscin and protogracillin, tribestane contains a diosgenin rhamnoglucoside sulfated in position 4 of the glucose residue, the structure of which has been shown by chemical and physicochemical methods.
- Mashchenko, N. E.,Gyulemetova, R.,Kintya, P. K.,Shashkov, A. S.
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p. 552 - 555
(2007/10/02)
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- STEROID GLYCOSIDES OF THE SEEDS OF Solanum melongena. STRUCTURES OF MELONGOSIDES A, B, E, F, AND H
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Three chromatographically individual fractions, each containing tigogenin glycosides and diosgenin glycosides have been isolated by chromatography on a silica gel column from a methanolic extract of eggplant seeds.To separate the mixture of two difficultly separable glycosides into individual components, each fraction was acetylated and epoxidated, and the derivatives obtained were separated chromatographically.The tigogenin glycoside peracetates isolated were saponified, and the diosgenin epoxide glycoside acetates were de-epoxidated and saponified, to give the individual glycosides, melongosides A, B, E, F, and H.The complete chemical structure of each melongoside has been shown with the aid of acid hydrolysis, methylation, and periodate oxidation followed by a study of the products obtained.
- Kintya, P. K.,Shvets, S. A.
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p. 575 - 578
(2007/10/02)
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- Afromontoside. A New Cytotoxic Principle from Dracaena afromontana
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A new cytotoxic principle, steroidal saponin afromontoside (1), has been isolated from a methanolic extract of the twigs of Dracaena afromontana.It was shown to be (25R)-furost-5-ene-3β,22α,26-triol 26-O-α-L-rhamnopyranoside 3-O-(4)>-β-D-glucopyranoside) by spectral and chemical methods.The aglycone of afromotoside, diosgenin, as well as dihydrodiosgenin and severall structurally related compounds have been shown to be cytotoxic to cultured KB cells.
- Reddy, K. Sambi,Shekhani, Mohammed S.,Berry, David E.,Lynn, David G.,Hecht, Sidney M.
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p. 987 - 992
(2007/10/02)
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- A NEW STEROID GLYCOSIDE, TACCAOSIDE, FROM Tacca cheancer
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A new steroid glycoside of the spirostan series - taccaoside (I) - has been isolated from an ethanolic extract of the roots of Tacca cheancer (family Taccaceae).An acid hydrolysate was found to contain the aglycone diosgenin (II) and the sugars D-glucose and L-rhamnose in a ratio of 1:2.By methyletion and hydrolysis of the permethylete (IV) it has been established that the two terminal L-rhamnose residues are attached at C-2 and C-3 of the D-glucose molecule which, in its turn, substitutes the hydroxy group at C-3 of diosgenin.Glycoside (I) has the structure of (25R)-spirost-5-en-3β-ol 3-O-2)>3)>-β-D-glucopyranoside>.
- Ngok, Fam Khoang,Kel'ginbaev, A. N.,Gorovits, M. B.,Abubakirov, N. K.
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p. 262 - 264
(2007/10/02)
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