- BESHORNIN AND BESHORNOSIDE, STEROIDAL SAPONINS OF BESHORNERIA YUCCOIDES
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Two new saponins beshornin and beshornoside have been isolated from the methanolic extract of Beshorneria yuccoides leaves and their structures elucidated.Beshornin is 3-O-4)-β-D-glucopyranosyl-(1->2)->-4)-β-D-glucopyranosyl-(1->3)>-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl>-(25R)-5α-spirostan-3β-ol, hereas beshornoside is 3-O-4)-β-D-glycopyranosyl-(1->2)>-4)-β-D-glucopyranosyl-(1->3)>-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl>-26-O--(25R)-5α-furostan-3β,22α,26-triol. - Key Word Index:Beshorneria yuccoides; spirostanol glycosides; furastanol glycosides; beshornin; beshornoside.
- Kintia, Pavel K.,Bobeyko, Valentin A.,Dragalin, Ivan P.,Shvets, Stepan A.
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- BIOLOGICAL ACTIVITIES OF FUROSTANOL SAPONINS FROM NICOTIANA TABACUM
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Two new furostanol saponins, tobacco saponin A and B were isolated from Nicotiana tabacum seeds.The 26-desgluco derivative of saponin B showed hemolytic and fungicidal activity, whereas the monodesmolide derivative of the minor saponin A had no such effects.Both saponins accumulate during ripening and are degraded during germination of the seeds.They were not found in any other part of the plant.Several Nicotiana species possess the same saponin pattern as recorded for N. tabacum.
- Gruenweller, Sabine,Schroeder, Ernst,Kesselmeier, Juergen
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- Structure of a steroid saponin from Digitalis ciliata
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A new steroid glycoside was isolated from leaves of Digitalis ciliata (Scrophulariaceae) by fractionation of the total extracted substances. Its structure was determined as (25R)-5α-spirostan-3β-ol 3-O-β-D-glucopyranosyl-(1→3)[β-D-fucopyranosyl-(1→2)] -β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside based on chemical transformations, physical constants, and spectral data.
- Gvazava,Kikoladze
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- α-Hydroxylation at C-15 and C-16 in Cholesterol: Synthesis of (25R)-5α-Cholesta-3β,15α,26-triol and (25R)-5α-Cholesta- 3β,16α,26-triol from Diosgenin
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(Matrix presented) (25R)-5α-Cholesta-3β,16α,26-triol 7b and (25R)-5α-cholesta-3β,15α,26-triol 10b were synthesized, via (25R)-5α-cholesta-3β,16β26-triol 5a, from diosgenin 3 in 52% yield over six steps and 47% yield over eight steps, respectively. An efficient method for inversion of a C-16β hydroxyl to the C-16α position and a short method for transposition of a C-16β hydroxyl to the C-15α position via the unexpected β-reduction of a C-15 ketone in a steroid are reported.
- Williams, John R.,Gong, Hua,Hoff, Nathan,Olubodun, Olaoluwa I.,Carroll, Patrick J.
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- Synthesis and antifungal activity of functionalized 2,3-spirostane isomers
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Invasive fungal infections are a major complication for individuals with compromised immune systems. One of the most significant challenges in the treatment of invasive fungal infections is the increased resistance of many organisms to widely used antifungals, making the development of novel antifungal agents essential. Many naturally occurring products have been found to be effective antimicrobial agents. In particular, saponins with spirostane glycosidic moieties - isolated from plant or marine species - have been shown to possess a range of antimicrobial properties. In this report, we outline a novel approach to the synthesis of a number of functionalized spirostane molecules that can be further used as building blocks for novel spirostane-linked glycosides and present results from the in vitro screenings of the antifungal potential of each derivative against four fungal species, including Candida albicans, Cryptococcus neoformans, Candida glabrata, and the filamentous fungus Aspergillus fumigatus.
- Upadhyay, Sunil Kumar,Creech, Clinton C.,Bowdy, Katharine L.,Stevens, Edwin D.,Jursic, Branko S.,Neumann, Donna M.
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- Steroidal saponins from Hosta longipes and their inhibitory activity on tumour promoter-induced phospholipid metabolism of HeLa cells
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Three new spirostanol saponins and two new furostanol saponins were isolated from the underground parts of Hosta longipes. Their structures were determined to be (25R)-5α-spirostane-2α,3β-diol (gitogenin) 3-O-{O-α-L- rhamnopyranosyl-(1 → 2)-β-D-galactopyranoside}, gitogenin 3-O-{O-α-L- rhamnopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 4)]-β-D- galactopyranoside}, (25R)-5α-spirostan-3β-ol (tigogenin) 3-O-{O-α-L- rhamnopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 4)]-β-D- galactopyranoside}, 26-O-β-D-glucopyranosyl-22-O-methyl-(25R)-5α- furostane-2α,3β,22ξ,26-tetrol 3-O-{O-α-L-rhamnopyranosyl-(1 → 2)-β-D- galactopyranoside} and 26-O-β-D-glucopyranosyl-22-O-methyl-(25R)-5α- furostane-2α,3β,22ε,26-tetrol 3-O-{O-α-L-rhamnopyranosyl-(1 → 2)-O- [β-D-glucopyranosyl-(1 → 4)]-β-D-galactopyranoside}, respectively. The isolated saponins and their derivatives were examined for inhibitory activity on 12-O-tetradecanoylphorbor-13-acetate-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to find new antitumour-promoter compounds.
- Mimaki, Yoshihiro,Kanmoto, Toshihiro,Kuroda, Minpei,Sashida, Yutaka,Satomi, Yoshiko,Nishino, Atsuko,Nishino, Hoyoku
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- Cytotoxic triterpene and steroidal glycosides from the seeds of Digitalis purpurea and the synergistic cytotoxicity of steroidal glycosides and etoposide in SBC-3 cells
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The phytochemical investigations of the seeds of Digitalis purpurea have revealed their richness in cardenolide and pregnane glycosides exhibiting potent cytotoxicity; further chemical examinations of the D. purpurea seeds have achieved the isolation of s
- Fukaya, Haruhiko,Kuroda, Minpei,Matsuo, Yukiko,Mimaki, Yoshihiro,Takatori, Kazuhiro,Tsuchihashi, Hiroko
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- Concise large-scale synthesis of tomatidine, a potent antibiotic natural product
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Tomatidine has recently generated a lot of interest amongst the pharmacology, medicine, and biology fields of study, especially for its newfound activity as an antibiotic agent capable of targeting multiple strains of bacteria. In the light of its low natural abundance and high cost, an efficient and scalable multi-gram synthesis of tomatidine has been developed. This synthesis uses a Suzuki–Miyaura-type coupling reaction as a key step to graft an enantiopure F-ring side chain to the steroidal scaffold of the natural product, which was accessible from low-cost and commercially available diosgenin. A Lewis acid-mediated spiroketal opening followed by an azide substitution and reduction sequence is employed to generate the spiroaminoketal motif of the natural product. Overall, this synthesis produced 5.2 g in a single pass in 15 total steps and 15.2% yield using a methodology that is atom economical, scalable, and requires no flash chromatography purifications.
- Boudreault, Pierre-Luc,Normandin, Chad
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- Steroidal constituents isolated from the seeds of Withania somnifera
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A new withanolide glycoside (1), two new ergostanol glycosides (2 and 3), and a new furostanol glycoside (4), along with nine known steroidal derivatives (5–12) were isolated from the seeds of Withania somnifera. The structures of the new compounds were determined using spectroscopic analysis and hydrolysis. The cytotoxic activities of the isolated compounds were evaluated against Ca9-22 human gingival carcinoma cells, HSC-2 human mouth carcinoma cells, and HL-60 human promyelocytic leukemia cells. Only 12 exhibited cytotoxic activity against these cell lines with IC50 values of 0.38, 0.54, and 1.5 μM, respectively.
- Iguchi, Tomoki,Kuroda, Minpei,Ishihara, Mai,Sakagami, Hiroshi,Mimaki, Yoshihiro
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supporting information
p. 2205 - 2210
(2019/11/03)
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- Gram-Scale Synthesis of Tomatidine, a Steroid Alkaloid with Antibiotic Properties Against Persistent Forms of Staphylococcus aureus
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We herein describe the first diastereoselective synthesis of the Solanum alkaloid tomatidine 1. The synthesis has been accomplished in 11 steps and 24.9 % overall yield (longest linear sequence). This methodology, which involves a convergent synthon insertion followed by a sequence of ring opening/nitrogen substitution/ring closing, allowed the generation of 1 on > 2 g scale. The synthetic challenge with the diastereoselective generation of the unusual spiroaminoketal moiety was solved through a combined azide reduction/addition sequence. The first diastereoselective synthesis of the phytosteroid yamogenin is also reported. Tomatidine has shown promising antibiotic properties against persistent forms of Staphylococcus aureus (S. aureus) and methicillin-resistant S. aureus (MRSA). In particular, it possesses the unique ability to kill persistent forms of S. aureus and MRSA while simultaneously potentiating the antibiotic efficacy of aminoglycoside antibiotics against wild type strains of the bacteria.
- Normandin, Chad,Malouin, Fran?ois,Marsault, Eric
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p. 2693 - 2698
(2020/05/04)
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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 0173-0176
(2020/05/23)
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- Diosgenin derivatives, and pharmaceutical compositions thereof and application thereof
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The invention relates to diosgenin derivatives. The structural formula of the diosgenin derivatives is as shown in a general formula (1) which is described in the specification. The invention also provides pharmaceutical compositions of the diosgenin derivatives and application thereof. According to the invention, systematic structural modification directed at double bonds at position 3 and position 5/6 of a lead compound is performed for the first time so as to synthesize a series of novel compounds; and the results of activity tests of the novel compounds at related targets show that most ofthe novel compounds have better activity than the activity of the lead compound and are very valuable for the treatment of neurodegenerative diseases. Thus, the diosgenin derivatives overcome defectsof conventional diosgenin derivatives and have important significance.
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Paragraph 0108-0110; 0113
(2019/01/24)
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- Structural characterization of a new steroidal saponin from Agave angustifolia var. Marginata and a preliminary investigation of its in vivo antiulcerogenic activity and in vitro membrane permeability property
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A new furostane steroidal saponin was isolated from the leaves of Agave angustifolia var. marginata. On the basis of chemical conversions and spectroscopic analyses, its structure was established as 3-[O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→3)-O]-[O-6-deoxy-α-L-mannopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl)oxy]-(3β,5α,22α,25R)-26-(β-D-glucopyranosyloxy)-22-methoxy-furostane (1). Results of preliminary biological investigations indicated that compound 1 showed significant protective effects against induced gastric ulcers using in vivo experimental models and demonstrated negligible toxicity on membrane integrity in the in vitro assays.
- Pereira, Gabriela Moysés,Ribeiro, Marcela Gon?alves,da Silva, Bernadete Pereira,Parente, José Paz
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p. 4345 - 4349
(2017/09/12)
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- Steroidal Saponins from Furcraea hexapetala Leaves and Their Phytotoxic Activity
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Four new steroidal saponins (1-4) along with 13 known saponins were isolated from the leaves of Furcraea hexapetala. The new compounds were identified as (20R,22R,25R)-3β-hydroxy-5α-spirostan-12-one 3-O-{α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (1), (25R)-3β-hydroxy-5α-spirost-20(21)-en-12-one 3-O-{α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (2), (25R)-5α-spirostan-3β-ol 3-O-{β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (3), and (25R)-5β-spirostan-3β-ol 3-O-{β-d-glucopyranosyl-(1→6)-O-β-d-galactopyranoside} (4) by spectroscopic analysis, including one- and two-dimensional NMR techniques, mass spectrometry, and chemical methods. The phytotoxicity of the isolated compounds against the standard target species Lactuca sativa was evaluated. Structure-activity relationships for these compounds with respect to phytotoxic effects are discussed.
- Calle, Juan M.,Pérez, Andy J.,Simonet, Ana M.,Guerra, José O.,Macías, Francisco A.
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p. 2903 - 2911
(2016/12/07)
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- Steroidal glycosides from the bulbs of Bessera elegans and their cytotoxic activities
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Examination of the bulbs of Bessera elegans (Liliaceae) led to isolation of nine new and five known steroidal glycosides. The structures of the nine compounds were determined based on the results of spectroscopic analysis, including two-dimensional NMR, and hydrolysis followed by chromatographic and spectroscopic analysis. The isolated compounds and derivatives were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human diploid fibroblasts. One compound, the pseudo-furostanol glycoside, induced apoptosis in HL-60 and A549 cells in a time-dependent manner and cell-cycle arrest at the G0/G1 phase in A549 cells.
- Matsuo, Yukiko,Akagi, Nana,Hashimoto, Chisato,Tachikawa, Fumito,Mimaki, Yoshihiro
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p. 244 - 256
(2014/01/06)
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- TIMOSAPONIN COMPOUNDS
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Provided herein are timosaponin compounds of Frmula I, II, IIΙ, I', II' and IIΙ', pharmaceutical compositions comprising the coumpounds, and processes of preparation thereof. Also provided are uses of said timosaponin compounds for preparing medicament for the treatment of diseases associated with beta-amyloid in hosts or subjects in need thereof.
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Paragraph 00249
(2013/10/22)
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- Desmettianosides A and B, bisdesmosidic furostanol saponins with molluscicidal activity from Yucca desmettiana
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Bioactivity-guided separation of the aqueous methanolic extract of Yucca desmettiana leaves, which in a preliminary screening exhibited significant molluscicidal activity, led to the isolation and structure elucidation of two new steroidal saponins (1 and 2). The structures of desmettianosides A and B, identified as bisdesmosidic furostanol glycosides with six and five sugar units, respectively, were established by detailed spectroscopic analyses of their NMR and MS data. Compounds 1 and 2 exhibited high molluscicidal activity against Biomphalaria alexandrina snails with LC100 values of 6 and 11 mg/L, respectively.
- Diab, Yasser,Ioannou, Efstathia,Emam, Ahmed,Vagias, Constantinos,Roussis, Vassilios
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experimental part
p. 686 - 690
(2012/06/01)
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- Novel approach to determining the absolute configurations at the C3-positions of various types of sterols based on an induced circular dichroism
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Circular dichroism (CD) spectra of the 2,2′-binaphthyl ester derived from Δ5-sterols showed not bisignate CD but diagnostic CD bands at around 210 and 240 nm. These bands might be attributable to an interaction between an olefinic chromophore and a binaphthyl one. Various types of unsaturated sterols were thus derivatized followed by complete hydrogenation, to give saturated sterols. As a result, CD spectra of the binaphthyl derivatives of the saturated sterols showed bisignate curves centered at 240 nm (3S(β): positive chirality; 3R(α): negative one). This suggested a straightforward and practical method for discriminating the absolute stereogenic center at the C-3 positions of sterols based on an induced CD. This finding should contribute significantly to the analysis of metabolites of various types of sterols.
- Fujiwara, Toshio,Taniguchi, Yuka,Katsumoto, Yukiteru,Tanaka, Takeyuki,Ozeki, Minoru,Iwasaki, Hiroki,Node, Manabu,Yamashita, Masayuki,Hosoi, Shinzo
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p. 1198 - 1204
(2012/11/07)
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- Furostane-type steroidal saponin from digitalis ciliata
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A new furostane-type steroidal glycoside and derivative of tigogenin (1) was isolated from aqueous wastes from production of the cardiac drug acetyldigitoxin from leaves of Digitalis ciliata Trautv. (Scrophulariaceae) and characterized. The structure of the glycoside was established using physical constants, chemical transformations, and spectral data as 3-O-β-D- glucopyranosyl-(1→3) [β-D-fucopyranosyl-(1→2)-β- Dglucopyranosyl-(1→4)-β-D-galactopyranosyl-(25R)-5α-furostan- 3β,22α,26-triol-26-O-β-Dglucopyranoside.
- Gvazava,Kikoladze
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experimental part
p. 246 - 249
(2010/09/15)
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- Structure and activities of a steroidal saponin from Chlorophytum nimonii (Grah) Dalz
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A new steroidal saponin, chloragin (1), was isolated and characterised from the aerial part of Chlorophytum nimonii. The structure of chloragin (1) was established as tigogenin-3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-β-D-xylopyranosyl-(
- Lakshmi, Vijai,Kumar, Rajesh,Pandey, Kartikey,Joshi, Bhawani Shanker,Roy, Raja,Madhusudanan, Kunnath Padamnabham,Tiwari, Priti,Srivastava, Arvind Kumar
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experimental part
p. 963 - 972
(2010/08/19)
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- Synthesis of the cytotoxic gitogenin 3β-O-[2-O-(α-L- rhamnopyranosyl)-β-D-galactopyranoside] and its congeners
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(25R)-5a-Spirostan-2a,3b-diol (gitogenin) 3β-O-[2-O-(α-L- rhamnopyranosyl)-β-D-galactopyranoside] (1), a cytotoxic spirostan saponin isolated from the underground parts of Hosta longipes (Liliaceae), was concisely synthesized. In this context, its congeners 2-4 were also prepared. All four compounds showed comparable potency to dioscin in inhibition against the growth of tumor cells. Georg Thieme Verlag Stuttgart.
- Li, Yingxia,Zhang, Yichun,Guo, Tiantian,Guan, Huashi,Hao, Yan,Yu, Biao
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p. 775 - 782
(2007/10/03)
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- Practical Procedures for the Preparation of N-tert-Butyldimethylsilylhydrazones and Their Use in Modified Wolff-Kishner Reductions and in the Synthesis of Vinyl Halides and gem-Dihalides
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In this work we develop practical chemistry for the preparation of N-tert-butyldimethylsilylhydrazone (TBSH) derivatives from carbonyl-containing compounds and show that these products serve as superior alternatives to simple hydrazones in Wolff-Kishner-type reduction reactions, in the Barton vinyl iodide preparation, in the synthesis of vinyl bromides, and in the synthesis of gem-diiodides, gem-dibromides, and gem-dichlorides. In our new procedure for silyl hydrazone synthesis, aliphatic and aromatic ketones and aldehydes are shown to undergo highly efficient coupling (typically >95% yield) to form the corresponding TBSH derivatives when combined with equimolar amounts of 1,2-bis(tert-butyldimethylsilyl)-hydrazine (BTBSH) and a catalytic quantity of scandium trifluoromethanesulfonate (typically, 0.01 mol %), neat, or in solvent. Optimized procedures are provided for the use of TBSH derivatives in a Wolff-Kishner-type reduction protocol that proceeds at low temperature (23-100 °C) and in a single reaction flask. Similarly, protocols for the use of TBSH derivatives as precursors to vinyl halides and gem-dihalides are described in detail.
- Furrow, Michael E.,Myers, Andrew G.
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p. 5436 - 5445
(2007/10/03)
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- Medicinal foodstuffs. VIII.1 Fenugreek seed. (2) : Structures of six new furostanol saponins, trigoneosides IVa, Va, Vb, VI, VIIb, and VIIIb, from the seeds of indian trigonella foenum-graecum L
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Following the characterization of trigoneosides Ia, Ib, IIa, IIb; IIIa, and IIIb, seven new steroidal saponins called trigoneosides IVa, Va, Vb, VI, VIIb, VIIIb, and IX were isolated from a medicinal foodstuff fenugreek seed, the seeds of Trigonella foenum-graecum L. (Leguminosae) originating from India. The structures of trigoneosides IVa, Va, Vb, VI, VIIb, and VIIIb were elucidated on the basis of chemical and physicochemical evidence.
- Yoshikawa, Masayuki,Murakami, Toshiyuki,Komatsu, Hajime,Yamahara, Johji,Matsuda, Hisashi
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p. 397 - 405
(2007/10/03)
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- Medicinal foodstuffs. IV. Fenugreek seed. (1): Structures of trigoneosides Ia, Ib, IIa, IIb, IIIa, and IIIb, new furostanol saponins from the seeds of indian Trigonella foenum-graecum L.
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Six new furostanol saponins called trigoneosides Ia, Ib, IIa, IIb, IIIa, and IIIb were isolated from a medicinal foodstuff, fenugreek seed, the seed of Trigonella foenum-graecum L. (Leguminosae) originating from India, together with two known saponins, glycoside D and trigofoenoside A. The structures of trigoneosides Ia, Ib, IIa, IIb, IIIa, and IIIb were determined on the basis of chemical and physicochemical evidence as 26-O-β-D- glucopyranosyl-(25S)5α-furostane-2α,3β,22ξ,26-tetraol 3-O-[β-D- xylopyranosyl(1→6)]-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25R)- 5α-furostane-2α-3β,22ξ,26-tetraol 3-O-[β-D-xylopyranosyl (1→6)]-β-D- glucopyranoside, 26-O-β-D-glucopyranosyl-(25S)-5β-furostane-3β,22ξ,26- triol 3-O-[β-D-xylopyranosyl (1→6)]-β-D-glucopyranoside, 26-O-β-D- glucopyranosyl-(25R)-5β-furostane-3β,22ξ,26-triol 3-O-[β-D-xylopyranosyl (1→6)]-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25S)-5α-furostane- 3β,22ξ,26-triol 3-O-[α-L-rhamnopyranosyl(1→2)]-β-D-glucopyranoside, and 26-O-β-D-glucopyranosyl-(25R)-5α-furostane-3β,22ξ,26-triol 3-O-[α-L- rhamnopyranosyl (1→2)]-β-D-glucopyranoside, respectively.
- Yoshikawa, Masayuki,Murakami, Toshiyuki,Komatsu, Hajime,Murakami, Nobutoshi,Yamahara, Johji,Matsuda, Hisashi
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- Steroidal saponins from Smilax officinalis
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Three new steroidal saponins were isolated from the rhizomes of Smilax officinalis. The structures of these saponins were established by extensive spectral data, hydrolysis and chemical correlation as sarsasapogenin 3-O-β- D-glucopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 6)]-β-D- glucopyranoside, neotigogenin 3-O-β-D-glucopyranosyl-(1 → 4)-[α-L- arabinopyranosyl-(1 → 6)]-β-D-glucopyranoside and 25S-spirostan-6β-ol 3- O-β-D-glucopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 6)]-β-D- glucopyranoside. Acid hydrolysis of the latter compound gave a sapogenin which has a new orientation of an hydroxyl on the steroidal skeleton. A route is proposed for the biogenesis of the latter sapogenin which is an uncommon steroidal aglycone.
- Bernardo, Robson Roney,Ventura Pinto, Antonio,Paz Parente, Jose
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p. 465 - 469
(2007/10/03)
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- Formation of ketones from alkyl nitrites in the solid state
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Alkyl nitrites selectively afforded the corresponding ketones upon photoirradiation in the solid state. It was suggested by the X-ray crystallographic analysis that the cavity in crystal and the initial conformation of the nitroso group had an influence on the yield of the ketones.
- Kinbara, Kazushi,Takezaki, Hiroshi,Kai, Akiyoshi,Saigo, Kazuhiko
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p. 217 - 218
(2007/10/03)
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- STEROIDAL SAPONINS FROM THE TUBERS OF DICHELOSTEMMA MULTIFLORUM AND THEIR INHIBITORY ACTIVITY ON CYCLIC-AMP PHOSPHODIESTERASE
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Phytochemical examination of the tubers of Dichelostemma multiflorum led to the isolation of three new steroidal saponins together with two known saponins.The structures of the new compounds were determined by spectral data and a new chemical transformations to the (25R)-5α-spirostane-1β,3β-diol (brisbagenin) 1-O-3)-4-O-acetyl-α-L-arabonopyranoside>, brisbagenin 1-O-2)-O-3)>-4-O-acetyl-α-L-arabinopyranoside> and (22S,25S)-5α-spirostan-3β-ol 3-O-2)-O-3)>-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside).The known compounds were identified as desglucolanatigonin II and gitonin, with certain amounts of the corresponding C-25S isomers.Inhibitory activity of the isolated saponins and their derivatives on cAMP phosphodiesterase was evaluated to identify new compounds with medicinal potential.
- Inoue, Toshihiro,Mimaki, Yoshihiro,Sashida, Yutaka,Nakaido, Tamotsu,Ohmoto, Taichi
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p. 1103 - 1110
(2007/10/02)
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- TRANSFORMATIONS OF SOLASODINE AND DERIVATIVES OF HECOGENIN BY CUNNINGHAMELLA ELEGANS
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Incubation of (25R)-5α-spirostane-3β,12β-diol (rickogenin) with the fungus Cunninghamella elegans led to the formation of (25R)-7β,12β-dihydroxy-5α-spirostan-3-one, (25R)-5α-spirostan-3β,7β,12β-triol and (25R)-5α-spirostan-3β,7α,12α-triol.Incubation of (25R)-5α-spirostan-3,12-dione (hecogenone) with the same fungus gave rise to (25R)-5α-spirostan-3,7,12-trione.When the (22R,25R)-spirosolane, solasod-5-en-3β-ol (solasodine) was incubated with C. elegans, solasod-5-ene-3β,7β-diol, solasod-5-ene-3β,7α-diol and 3β-hydroxysolasod-5-en-7-one were produced.In contrast, incubation of solasodine with Penicillium patulum gave solasod-4-en-3-one and the 6-methylsalicylic acid salt of solasodine.
- Patel, Asmita V.,Blunden, Gerald,Crabb, Trevor A.
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p. 125 - 134
(2007/10/02)
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- A tigogenin pentasaccharide from Cestrum diurnum.
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A new steroidal saponin named diurnoside 1 has been isolated from a methanolic extract of fresh leaves of Cestrum diurnum and the structure, (25 R)-5 alpha-spirostan-3beta-yl-4-O-[2-O-(beta-D-gluco pyranosyl)-beta-D-glucopyranosyl]-3-O-[beta-D-xylopyranosyl]-beta-D- glucopyranosyl]-beta-D-galactopyranoside, was determined by modern NMR technique and chemical reactions.
- Ahmad,Baqai,Ahmad
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p. 511 - 515
(2007/10/02)
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- Synthesis of CP-88,818 (Tiqueside), An Internal Standard For A Quantitative HPLC/MS Assay System
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A polydeuterated form of CP-88,818 (1, tiqueside) was needed as an internal standard for a quantitative HPLC/MS assay system. CP-88,818 (11) with undetectable D0 content was synthesized in five steps from tigogenin (2).The low D0 content was achieved through two sequential incorporation procedures which gave results superior to those achieved through a single incorporation procedure.A preparatively useful procedure for removing spirostane impurities found in natural occurring tigogenin was also discovered.
- Zawistoski, Michael P.,Kiplinger, Jeffrey P.,McCarthy, Peter A.
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p. 4799 - 4808
(2007/10/02)
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- STEROIDAL SAPONINS FROM SMILAX RIPARIA AND S. CHINA
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Two new neotigogenin glycosides were isolated from the rhizomes and roots of Smilax riparia and a new isonarthogenin glycoside from those of S. china.The structures were elucidated by a combination of spectroscopic analysis and hydrolysis followed by spectral and chromatographic analysis.Several known saponins were also isolated and identified.The inhibitory activity of the saponins on cAMP phosphodiesterase was examined. Key Word Index - Smilax riparia; Smilax china; Liliaceae; steroidal saponins; neotigogenin glycosides; isonarthogenin glycoside; cAMP phosphodiesterase.
- Sashida, Yutaka,Kubo, Satoshi,Mimaki, Yoshihiro,Nikaido, Tamotsu,Ohmoto, Taichi
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p. 2439 - 2444
(2007/10/02)
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- Spirostanol saponins from Yucca aloifolia rhizomes
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From the rhizomes of Yucca aloifolia two spirostanol saponins (A and B) have been isolated and characterized as 3-O-[β-d-glucopyranosyl(1→2)-β-d-glucopyranosyl]-25R-5α-spirostane-3β-ol and.
- Bahuguna,Sati
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p. 342 - 343
(2007/10/02)
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- Antifungal Activity of the Saponin Fraction Obtained from Asparagus Officinalis L. and Its Active Principle
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Antifungal activity was detected in the crude saponin fraction obtained from the bottom cut of Asparagus officinalis L.This activity was specific to certain fungi, for example Candida, Cryptococcus, Trichophyton, Microsporum and Epidermophyton.Attempts were made to isolate the active principles from this fraction; in this way a new saponin (AS-1) was isolated, and its structure was estimated to be 3-O-2)>4)>-β-D-glucopyranosyl>-(25S),5β-spirostan-3β-ol.The minimum inhibitory concentration (MIC) ranged from 0.5 μg/ml to more than 8 μg/ml depending upon the nature of the fungi.On the basis of the work carried out here, it is probable that asparagus will contain additional antifungal principles.
- Shimoyamada, Makoto,Suzuki, Masayuki,Sonta, Hiromi,Maruyama, Makiko,Okubo, Kazuyoshi
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p. 2553 - 2557
(2007/10/02)
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- STEROIDAL SAPONINS FROM CHLOROPHYTUM MALAYENSE
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Four new steroidal saponins, chloromalosides A-D, were isolated from the rhizomes of Chlorophytum malayense.On the basis of detailed chemical and spectroscopic evidence, the structures of chloromalosides A-D were elucidated to be neohecogenin 3-O-β-D-glucopyranosyl(1->2)-3)>-β-D-glucopyranosyl(1->4)-β-D-galactopyranoside, 26-β-D-glucopyranosyl-22-hydroxy-25(S)-5α-furostane-3β,26-diol-3-O-β-D-glucopyranosyl(1->2)-3)>-β-D-glucopyranosyl(1->4)-β-D-galactopyranoside, neohecogenin 3-O-β-D-xylopyranosyl(1->3)-2)>-β-D-glucopyranosyl(1->4)-2)>-β-D-galactopyranoside and neotigogenin 3-O-β-D-xylopyranosyl(1->3)-2)>-β-D-glucopyranosyl(1->4)-2)>-β-D-galactopyranoside, respectively.
- Xing-Cong, Li,Wang, De-Zu,Yang, Chong-Ren
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p. 3893 - 3898
(2007/10/02)
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- STEROIDAL SAPONINS FROM DIURANTHERA MAJOR
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In addition to chloromaloside A, three new steroidal saponins, diuranthosides A-C, were isolated from the fresh roots of Diuranthera major.On the basis of chemical and spectroscopic analysis, the structures of diuranthosides A-C were established as neotigogenin 3-O-β-D-glucopyranosyl(1->2)-3)>-β-D-glucopyranosyl(1->4)-β-D-galactopyranoside, neohecogenin 3-O-β-D-glucopyranosyl(1->3)-β-D-xylopyranosyl(1->3)-2)>-β-D-glucopyranosyl(1->4)-β-D-galactopyranoside and neohecogenin 3-O-β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2)-3)-β-D-xylopyranosyl(1->3)>-β-D-glucopyranosyl(1->4)-β-D-galactopyranoside, respectively.
- Li, Xing-Cong,Wang, Yi-Fei,Wang, De-Zu,Yang, Chong-Ren
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p. 3899 - 3901
(2007/10/02)
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- Further Studies on Steroidal Glycosides from Bulbs, Roots and Leaves of Allium sativum L.
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A new furostanol glycoside (2), named sativoside-B1, was isolated from garlic, bulbs of Allium sativum L., along with proto-desgalactotigonin (3).The structure of 2 was established to be (25R)-26-O-β-D-glucopyranosyl-22-hydroxy-5α-furostane-3β,6β,26-triol 3-O-β-D-glucopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-3)-O-β-D-glucopyranosyl-(1->4)-O-β-D-galactopyranoside.From roots of this plant, two new steroidal glycosides, named sativoside-R1 (16) and sativoside-R2 (15) were isolated and their structures were determined to be (25R)-26-O-β-D-glucopyranosyl-22-hydroxy-5α-furostane-3β,26-diol 3-O-β-D-glucopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-3)>-O-β-D-glucopyranosyl-(1->4)-O-β-D-galactopyranosyde (16) and its corresponding spirostanol glycoside (15).Besides these glycosides, three known glycosides, 3, desgalactotigonin (13) and F-gitonin (14) were isolated and identified.In a glycoside fraction of the leaves of A. sativum, steroidal glycosides were not detected by thin layer chromatography analysis.
- Matsuura, Hiromichi,Ushiroguchi, Tsuyoshi,Itakura, Yoichi,Fuwa, Toru
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p. 2741 - 2743
(2007/10/02)
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- THE STEROIDAL GLYCOSIDES OF THE FLOWERS OF YUCCA GLORIOSA
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Four steroidal compounds were isolated from the fresh flowers of Yucca gloriosa and their structures were elucidated as tigogenin 3-O-β-D-xylopyranosyl-β-lycotetraoside, gitogenin 3-O-β-D-xylopyranosyl-β-lycotetraoside, gitogenin 3-O-α-rhamnopyranosyl-β-lycotetroside and proto-type of gitogenin 3-O-β-D-xylopyranosyl-β-lycotetraoside, on the basis of physical and chemical investigation.Key Word Index - Yucca gloriosa; Liliaceae; tigogenin glycoside; gitogenin glycosides; furostanol glycoside.
- Nakano, Kimiko,Matsuda, Emi,Tsurumi, Kaori,Yamasaki, Tokushi,Murakami, Kotaro,et al.
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p. 3235 - 3240
(2007/10/02)
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- STEROID GLYCOSIDES OF THE ROOTS OF Capsicum annuum. II. THE STRUCTURE OF THE CAPSICOSIDES
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Two tigogenin glycosides and two diosgenin glycosides have been isolated from a methanolic extract of the roots of bush red pepper.An aattempt to isolate the individual spirostanol glycosides directly was unsuccessful.These compounds have very similar structures.For their separation, acetylation and epoxidation of the double bond of the aglycon, diosgenin, in the corresponding glycosides was performed.The derivatives obtained were purified by chromatography.To establish the complete chemical structure of each capsicoside we used both chemical and physical methods:complete and partial acid hydrolysis, methylation followed by methanolysis, IR spectroscopy, mass spectroscopy, etc.It was shown that capsicoside A2 is (25R)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside, capsicoside B2 is (25R)-5α-spirostan-3β-ol 3-O-4)-β-D-galactopyranoside>, capsicoside A3 is (25R)-spirost-5-en-3β-ol 3-O-β-D-galactopyranoside, and capsicoside B3 is identical with funkioside C.
- Gutsu, E. V.,Kintya, P. K.,Lazur'evskii, G. V.
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p. 202 - 205
(2007/10/02)
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- Steroidal glycosides of Tribulus terrestris Linn.
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Besides β-sitosterol-β-D-glucoside and dioscin, two new steroidal glycosides, neohecogenin glucoside and tribulosin, isolated from the aerial part of Tribulus terrestris Linn. were respectively shown to be neohecogenin-3-O-β-D-glucopyranoside (2) and neotigogenin-3-O-β-D-xylopyranosyl(1->2)-3)>-β-D-glucopyranosyl(1->4)-2)>-β-D-galactopyranoside (7).
- Mahato, Shashi B.,Sahu, Niranjan P.,Ganguly, Amar N.,Miyahara, Kazumoto,Kawasaki, Toshio
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p. 2405 - 2410
(2007/10/02)
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- TOMATOSIDE A FROM THE SEEDS OF Lycopersicum esculentum
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Results are given which confirm the structure of the furostanol glycoside from tomato seeds forming wastes of the preserving industry.From a butanolic extract of the seeds of Lycopersicum esculentum Mill. we have isolated the furostanol glycoside tomatoside A (I) the structure of which has been established as 25(S)-5α-furostan-3β,22α,26-triol 26-O-β-D-glucopyranoside 3-O2)-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside>.At the same time, by enzymatic and chemical transformations three new spirostanol glycosides of neotigogenin have been obtained: tomatoside B (III), which is 25(S)-5α-spirostan-3β-ol 3-O-2)-β-D-galactopyranoside>, 25(S)-5α-spirostan-3β-ol 3-O-4)-β-D-galactopyranoside> (V), and 25(S)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside (IV).
- Shchelochkova, A. P.,Vollerner, Yu. S.,Koshoev, K. K.
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p. 386 - 392
(2007/10/02)
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- ISOLATION AND CHARACTERIZATION OF A FUROSTANOL GLYCOSIDE FROM FENUGREEK
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From the seed of fenugreek, a new glycoside has been isolated and shown to have the structure, (25S)-22-O-methyl-5α-furostan-3β,22,26-triol 3-O-α-rhamnopyranosyl(1-->2)3)>-β-D-glucopyranoside-26-O-β-D-glucopyranoside.Key Word Index - Trigonella foenumgraecum; Fabaceae; fenugreek; furostanol glycoside; spirostanol
- Hardman, Roland,Kosugi, Junzo,Parfitt, Robert T.
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p. 698 - 700
(2007/10/02)
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