- Symphytoxide A, a triterpenoid saponin from the roots of Symphytum officinale.
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A new triterpenoidal saponin of hederagenin named symphytoxide A has been isolated from the ethanolic extract of the roots of Symphytum officinale and characterized on the basis of chemical investigations and spectroscopic studies as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)- alpha-L-arabinopyranosyl] hederagenin. The structure of this new saponin was established on the basis of 1D and 2D NMR experiments including heteroCOSY, COSY-45 degrees as well as HMBC measurements and other spectroscopic techniques. The saponin exhibited hypotensive activity in anesthetized rats.
- Ahmad,Noorwala,Mohammad,Sener,Gilani,Aftab
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- Triterpenoid saponins of pulsatilla koreana root have inhibition effects of tumor necrosis factor-α secretion in lipopolysaccharide-induced RAW264.7 cells
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In the present study, a new oleanane-type triterpenoid saponin, pulsatilloside F (1), along with 21 known compounds (2-22), were isolated from the root of Pulsatilla koreana. Their chemical structures were elucidated by mass, 1H-, 13C-NMR, correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC) spectroscopy. Anti-inflammatory effects of the compounds were evaluated in terms of inhibitory of tumor necrosis factor a (TNF-α) secretion in the lipopolysaccharide (LPS)-stimulated murine RAW264.7 macrophage cell line. Compounds 19 and 20 exhibited particularly inhibitory effects with respective IC50 values of 0.32 and 0.65 μm. Compounds 1-4, 7 and 10-13 exhibited inhibitory effects with inhibition rates up to 41.55-73.76% at a concentration of 5 μm, respectively.
- Li, Wei,Ding, Yan,Sun, Ya Nan,Yan, Xi Tao,Yang, Seo Young,Choi, Chun Whan,Cha, Ji Yun,Lee, Young Mi,Kim, Young Ho
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- A BISDESMOSIDIC TRITERPENE SAPONIN FROM CEPHALARIA TRANSSYLVANICA
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The structure of cephalaria saponin B, isolated from Cephalaria transsylvanica was eluciated as 3-O-4)-α-L-rhamnopyranosyl(1->2)-β-D-xylopyranosyl>->-3β,24-dihydroxy-12(13)-oleanene-28-oic acid. - Key words: Cephalaria transsylvanica; Dipsacaceae; flowers; cephalaria saponin B; hederagenin.
- Alankus-Caliskan, Oezgen,Anil, Hueseyin
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- Triterpene glucosides from the leaves of aralia elata and their cytotoxic activities
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Three new triterpene glucosides, named congmuyenosides C-E (1-3, resp.), along with four known ones, were isolated from an EtOH extract of Aralia elata (Miq.) Seem. leaves. The structures of the new compounds were identified as 3-O-{β-D-glucopyranosyl-(1→
- Kuang, Hai-Xue,Wang, Zhi-Bin,Wang, Qiu-Hong,Yang, Bing-You,Xiao, Hong-Bin,Okada, Yoshihito,Okuyama, Tohru
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- TRITERPENE GLYCOSIDES OF Hedera colchica. STRUCTURE OF HEDERACOLCHISIDES E AND F
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The leaves of Colchis ivy (family Araliaceae) have yielded polar glycosides - hederacolchisides E and F - and their structures have been established.It has been shown on the basis of the results of methylation and of acid and alkaline hydrolysis that these glycosides are hexaosides of oleanolic acid and of hederagenin.
- Dekanosidze, G. E.,Dzhikiya, O. D.,Vugal'ter, M. M.,Kemertelidze, E. P.
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- Interconversion of hederagenin and gypsogenin and accessing 4-epi-hedragonic acid
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Gypsogenin (1) and hederagenin (2) were isolated by extracting the powdered roots of Saponaria officinalis and the pericarp of Sapindus saponaria, respectively. While the gypsophila derived saponin can be obtained easily and in large quantities as a technical product, the plant material from Sapindus saponaria is difficult to obtain in Europe and the North-Americas, whereas in Latin America it is readily available (unlike the gypsophila saponin). In order to achieve a better accessibility of both aglycones, gypsogenin (1) and hederagenin (2), a simple synthesis for their interconversion was developed. Modification of the reaction conditions led to the first synthesis of 4-epi-hedragonic acid (3).
- Csuk, René,Serbian, Immo,Str?hl, Dieter
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- Eranthisaponins A and B, two new bisdesmosidic triterpene saponins from the tubers of Eranthis cilicica
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The present investigation aimed at the glycoside constituents of the tubers of Eranthis cilicica has resulted in the isolation of two new bisdesmosidic triterpene saponins based upon hederagenin, named eranthisaponins A (1) and B (2), along with four known triterpene saponins. The structures of the new saponins 1 and 2 were determined on the basis of spectroscopic analysis, including extensive 1D and 2D NMR data, and acid hydrolysis followed by chromatographic analysis. This is the first report concerning the secondary metabolites of E. cilicica.
- Watanabe, Kazuki,Mimaki, Yoshihiro,Sakuma, Chiseko,Sashida, Yutaka
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- TRITERPENE GLYCOSIDES OF Climacoptera transoxana. I.
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Two tripene glycosides - copterosides B and C -have been isolated from the epigeal part of Climacoptera transoxana (Iljin) Botsch.On the basis of chemical transformations and physicochemical characteristics, copteroside B has been identified as hedaragenin 3-O-β-D-glucopyranosiduric acid while copteroside C has the structure of hederagenin 3-O-.
- Annaev, Ch.,Isamukhamedova, M.,Abubakirov, N. K.
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- Utility of coupled-HSQC experiments in the intact structural elucidation of three complex saponins from Blighia sapida
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The structures of three complex saponins from the fruit pods of Blighia sapida have been elucidated and their 1H and 13C NMR spectra assigned employing a variety of one- and two-dimensional NMR techniques without degradative chemistry. The saponins have either four or six monosaccharide units linked to a triterpene aglycone. High-resolution, proton-coupled-HSQC spectra were important for determining both the identities of the intact monosaccharide units and coupling constants in strongly coupled proton spin systems. These NMR experiments will prove crucial as the complexity of saponin structures reaches the limit that can be determined solely by NMR.
- Mazzola, Eugene P.,Parkinson, Ainsley,Kennelly, Edward J.,Coxon, Bruce,Einbond, Linda S.,Freedberg, Darón I.
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- Triterpene glycosides from the whole plant of Anemone hupehensis var. japonica and their cytotoxic activity
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Three new triterpene glycosides (1-3), together with eight known triterpene glycosides (4-11), were isolated from the whole plant of Anemone hupehensis var. japonica (Ranunculaceae). The structures of the new compounds were determined on the basis of spec
- Yokosuka, Akihito,Sano, Tomoe,Hashimoto, Ken,Sakagami, Hiroshi,Mimaki, Yoshihiro
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- Triterpenoid saponins and others glycosides from the stem barks of Pancovia turbinata Radlk
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In our continuing search of saponins from the plant of Sapindaceae family, phytochemical investigation of the stem barks of Pancovia turbinata Radlk., led to the isolation and structural characterization of two new triterpenoid saponins, named turbinatosi
- Moffi Biang, Armand Emmanuel,Messi, Lin Marcellin,Le Doux Kamto, Eutrophe,Simo, Line Made,Lavedan, Pierre,Vedrenne, Marc,Mbing, Josephine Ngo,Pegnyemb, Dieudonné Emmanuel,Haddad, Mohamed,Noté, Olivier Placide
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- Separation and quantification of selected sapogenins extracted from nettle, white dead-nettle, common soapwort and washnut
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Saponins are an important group of secondary metabolites naturally occurring in plants with important properties like: antibacterial, antiviral and antifungal. Moreover, they are widely used in the cosmetic industry and household chemistry. The sapogenins
- Buszewski, Bogus?aw,Kie?basa, Anna,Ligor, Magdalena,Ratiu, Ileana-Andreea
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- New triterpenoid saponin glycosides from the fruit fibers of: Trichosanthes cucumerina L.
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Five new triterpenoid saponin glycosides, trichocucumerisides A-E (1-5), together with eleven known compounds (6-16) were isolated from Trichosanthes cucumerina fruit fibers. The structures of the new compounds were elucidated by detailed analysis of NMR and mass spectroscopic data as well as chemical reactions. The anti-inflammatory study against nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells shows that compounds 7 and 9 exhibited stronger NO inhibitory activity, with IC50 values of 3.0 and 2.7 μM, respectively, with comparison to positive references Celecoxib and aminoguanidine (IC50 values 75.7 and 75.0 μM, respectively). Compounds 7 and 9 also possessed a greater selectivity index (SI) of approximately 3-4-fold activity than that of the positive references.
- Chulrik, Wanatsanan,Chunglok, Warangkana,Li, Jian-Xin,Suebsakwong, Parichat,Suksamrarn, Apichart,Yao, Zhu-Jun
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p. 10461 - 10470
(2020/03/27)
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- Cycloartane and oleanane glycosides from the tubers of Eranthis cilicica
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Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1-11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.
- Watanabe, Kazuki,Mimaki, Yoshihiro,Fukaya, Haruhiko,Matsuo, Yukiko
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- Antibacterial activity of a triterpenoid saponin from the stems of Caesalpinia pulcherrima Linn.
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A new compound 1 was isolated from the methanolic extract of the stems of the Caesalpinia pulcherrima Linn. along with a reported compound (2) 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. The new compound 1 has m.p. 272–274°C, m.f. C46H74O17, [M]+ m/z 898. It was characterised as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl ester by various colour reactions, chemical degradations and spectral analyses. Antibacterial activity of compound 1 was screened against various Gram-positive and Gram-negative bacteria and showed significant results.
- Asati, Nidhi,Yadava
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p. 499 - 507
(2017/09/30)
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- Artefact formation during acid hydrolysis of saponins from Medicago spp.
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Artefact compounds obtained during acid hydrolysis of saponins from Medicago spp. (Fabaceae), have been monitored and evaluated by GC-FID. Their identification has been performed by GC-MS and 1H and 13C NMR. Saponins with different substituents on the triterpenic pentacyclic aglycones were considered, and their hydrolysis products were detected and quantified during 10?h of time course reaction. From soyasapogenol B glycoside the well known soyasapogenols B, C, D and F were obtained together with a previously undescribed sapogenol artefact identified as 3β,22β,24-trihydroxyolean-18(19)-en and named soyasapogenol H. From a zanhic acid saponin two major artefact compounds identified as 2β,3β,16α-trihydroxyolean-13(18)-en-23,28-dioic acid and 2β,3β,16α-trihydroxyolean-28,13β-olide-23-oic acid were obtained, together with some zanhic acid. Other compounds, detected in very small amount in the reaction mixture, were also tentatively identified based on their GC-MS and UV spectra. The other most characteristic saponins in Medicago spp., hederagenin, bayogenin and medicagenic acid glycosides, under acidic condition of hydrolysis, released instead the correspondent aglycones and generated a negligible amount of artefacts. Nature of artefacts and mechanism of their formation, involving a stable tertiary carbocation, is here proposed and discussed for the first time.
- Tava, Aldo,Biazzi, Elisa,Mella, Mariella,Quadrelli, Paolo,Avato, Pinarosa
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p. 116 - 127
(2017/04/13)
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- Anticancer and antiviral estimation of three Ulmus pravifolia extracts and their chemical constituents
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Anticancer and antiviral activity of methanol, chloroform and butanol extracts of Ulmus pravifolia were tested on three cytokines of the human ascites fluid, TNF-alpha, Interferonsgamma and NO. Chloroform and butanol extracts showed a significant curative effect. Both butanol and chloroform extract undergo chromatographic fractionation to yield five compounds identified as Hederagenin 3-O-β-D-glucopyranoside (1), Kaempferol 3-O-β-D-glucopyranosyl- (1→2)-α -L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-7-O-β-D-glucopyranoside (2), 24-hydroxy-24-methylcycloartanol trans-ferulate (3), lupeol caffeate (4) and UlmicinD (5). All compounds were isolated from the plant for the first time. The five compounds showed significant curative effect.
- Hamed, Manal M.,El-Amin, Samir M.,Refahy, Laila A.,Soliman, El-Sayed A.,Mansour, Wafaa A.,Abu Taleb, Hoda M.,Morsi, Eman A.
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p. 1621 - 1634
(2016/01/26)
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- Triterpene glycosides from the stems and leaves of Lonicera japonica
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Five new triterpene glycosides, namely lonicerosides F-J (1-5), together with five known ones, were isolated from the stems and leaves of Lonicera japonica. Based on extensive spectroscopic analysis, including twodimensional (2D)-NMR experiments, and the
- Kuroda, Minpei,Shizume, Takaaki,Mimaki, Yoshihiro
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- Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis
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Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1-5), together with seven known saponins (6-12). Their structures were determined by the extensive use of 1D and 2D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1-12, prosapogenins 4a, 5a, 10a-12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6-8, 5a, 10a-12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC 50 values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1-4 and 9 showed selective cytotoxicity against the U87MG cells.
- Wang, Xiao-Yang,Gao, Hui,Zhang, Wei,Li, Yuan,Cheng, Guang,Sun, Xiao-Li,Tang, Hai-Feng
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p. 5714 - 5720
(2013/10/01)
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- Three new triterpene saponins from Clematis chinensis
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Three new triterpene saponins, clematochinenosides H-J (1-3), were isolated from the roots and rhizomes of Clematis chinensis. Their structures were elucidated on the basis of spectroscopic means including 1D and 2D NMR experiments and hydrolysis products
- Fu, Qiang,Zan, Ke,Zhao, Ming-Bo,Zhou, Si-Xiang,Shi, She-Po,Jiang, Yong,Tu, Peng-Fei
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p. 610 - 618
(2013/07/26)
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- Cytotoxic triterpene saponins from the stem bark of Kalopanax pictus
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Three new compounds, 3β,6β,23-trihydroxyolean-12-en-28-oic acid 3-O-α-l-arabinopyranoside (1), kalopanaxsaponin L (2), and kalopanaxsaponin M (13), as well as eleven known compounds (3-12 and 14), were isolated from the stem bark of Kalopanax pictus. Their structures were determined on the basis of extentive spectroscopic analyses and acid hydrolysis. The cytotoxicity of the compounds was evaluated in three human carcinoma cell lines, including HL-60, HCT-116, and MCF-7. Compounds 1, 5-8, 10, and 11 exhibited significantly cytotoxic activity toward HL-60 cells, with IC 50 values ranging from 0.1 to 6.9 μM. Compounds 4-7 and 14 showed significant cytotoxicity against HCT-116 cells, with IC50 values ranging from 0.4 to 9.2 μM. Remarkably, the cytotoxic activities of compounds 5-7 against HCT-116 cells were greater than that of the anticancer chemotherapy drug, mitoxantrone (IC50 = 3.7 μM). Compounds 1, 3, 5, and 14 were cytotoxic toward MCF-7 cells with IC50 values in a range of 7.4-14.5 μM.
- Quang, Tran Hong,Ngan, Nguyen Thi Thanh,Minh, Chau Van,Kiem, Phan Van,Boo, Hye-Jin,Hyun, Jin-Won,Kang, Hee-Kyoung,Kim, Young Ho
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experimental part
p. 177 - 182
(2012/05/05)
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- Anti-inflammatory triterpenoid saponins from the stem bark of Kalopanax pictus
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Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3-2-en-28-oic acid 28-O-β-d-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-l- arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(→4)-β-d- glucopyranosyl-(→6)-β-d-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl- α-l-arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(→4)- β-d-glucopyranosyl-(→6)-β-d-glucopyranoside (5), as well as 10 known compounds (6-15), were isolated from the stem bark of Kalopanax pictus. Compounds 1-5 and 7-14 inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 0.6to 16.4 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure-activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.
- Quang, Tran H.,Ngan, Nguyen T.T.,Minh, Chau V.,Kiem, Phan V.,Nhiem, Nguyen X.,Tai, Bui H.,Thao, Nguyen P.,Tung, Nguyen H.,Song, Seok B.,Kim, Young H.
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experimental part
p. 1908 - 1915
(2011/11/11)
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- Effect of triterpenes and triterpene saponins from the stem bark of Kalopanax pictus on the transactivational activities of three PPAR subtypes
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Kalopanax pictus (Araliaceae) is a deciduous tree that grows in East Asian countries. Its stem bark and leaves have been used in traditional medicine to treat rheumatic arthritis, neurotic pain, and diabetes mellitus. A phytochemical study on a methanol extract of the stem bark of K. pictus resulted in the isolation of three new compounds, 6β,16α-dihydroxy-hederagenin 3-O-β-d-glucuronopyranoside (1), 3-O-β-d-glucuronopyranosyl-28-O- β-d-glucopyranosyl-6β,16α-dihydroxy-oleanolic acid (2), and 3-O-β-d-galactopyranosyl(1→3)-α-l-arabinopyranosyl hederagenin 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester (3), along with eight known compounds (4-11). Their structures were established on the basis of chemical and spectroscopic methods (IR, 1D and 2D NMR, and HRESITOFMS). Compounds 1-6 and 8-10 upregulated PPARs transcriptional activity in a dose-dependent manner in HepG2 cells, with EC50 values in the range 0.20-15.5 μM. Moreover, the specific PPAR transactivational effects of compounds 1-6 and 8-10 on separate PPAR subtypes, PPARα, -γ, and -β(δ) were further investigated. Compounds 4, 5, 8, and 10 showed significant PPARα transactivational activity, with EC50 values of 7.8, 8.0, 10.3, and 17.3 μM, respectively. Compounds 2, 4, 6, and 8-10 exhibited PPARγ dose-dependent transactivational activity, with EC 50 values of 14.7, 15.5, 14.8, 10.9, 17.1, and 16.3 μM, whereas compounds 8 and 10 significantly upregulated PPARβ(δ) transcriptional activity, with EC50 values of 15.7 and 17.7 μM, respectively.
- Quang, Tran Hong,Ngan, Nguyen Thi Thanh,Minh, Chau Van,Kiem, Phan Van,Thao, Nguyen Phuong,Tai, Bui Huu,Nhiem, Nguyen Xuan,Song, Seok Bean,Kim, Young Ho
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experimental part
p. 2567 - 2575
(2011/12/02)
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- Triterpene saponins from clematis chinensis and their potential anti-inflammatory activity
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Seven new triterpene saponins, clematochinenosides A-G (1-7), together with 17 known saponins (8-24), were isolated from the roots and rhizomes of Clematis chinensis. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1, 3-7, and 20-24 showed inhibitory activities against COX-1 and COX-2 enzymes.
- Fu, Qiang,Zan, Ke,Zhao, Mingbo,Zhou, Sixiang,Shi, Shepo,Jiang, Yong,Tu, Pengfei
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experimental part
p. 1234 - 1239
(2010/11/04)
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- Bidesmoside triterpenoid glycosides from Stauntonia chinensis and relationship to anti-inflammation
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Ten triterpenoid glycosides, yemuoside YM26-35 (1-9 and 12), were isolated from a traditional Chinese medicine known as "Ye Mu Gua" (Stauntonia chinensis DC.) along with two known ones, kalopanax saponin C (10) and sieboldianoside A (11). Their
- Gao, Hao,Zhao, Feng,Chen, Guo-Dong,Chen, Shao-Dan,Yu, Yang,Yao, Zhi-Hong,Lau, Brad W.C.,Wang, Zhao,Li, Jin,Yao, Xin-Sheng
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experimental part
p. 795 - 806
(2010/05/17)
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- New triterpenic saponins from the aerial parts of Medicago arabica (L.) Huds
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The reinvestigation of saponin composition from Medicago arabica from Italy allowed the detection of nineteen (1-19) saponins. All of them were purified by reverse-phase chromatography and their structures elucidated by spectroscopic and spectrometric (1D and 2D NMR; ESI-MS/MS) and chemical methods. Fourteen were known saponins, previously found in other plants including other Medicago species. They have been identified as glycosides of oleanolic acid, 2β,3β-dihydroxyolean-12-en-28-oic acid, hederagenin, bayogenin and soyasapogenol B. Five saponins, identified as 3-O-[-α-L- arabinopyranosyl(1→2)-β-D-glucuronopyranosyl]-30-O-β-D- glucopyranosyl 2β,3β,30-trihydroxyolean-12-en-28-oic acid (1), 3-O-[α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyl] -30-O-[β-D-glucopyranosyl]3β,30-dihydroxyolean-12-en-28-oic acid (2), 3-O-|β-D-glucuronopyranosyl]-30-O-[α-L-arabinopyranosyl(1→2) -β-D-glucopyranosyl] 2β,3β,30-trihydroxyolean-12-en-28-oic acid (3), 3-O-[β-D-glucuronopyranosyl]-30-O-[α-L- arabinopyranosyl(1→2)-β-D-glucopyranosyl] 3β,30-dihydroxyolean- 12-en-28-oic acid (4) and 3-O-[β-D-glucuronopyranosyl]-30-O-[β-D- glucopyranosyl] 2β,3β,30-trihydroxyolean-12-en-28-oic acid (5), are reported here as new natural compounds. These new saponins, possessing a hydroxy group at the 30-methyl position of the triterpenic skeleton, have never been previously found in the genus Medicago.
- Tava, Aldo,Mella, Mariella,Avato, Pinarosa,Biazzi, Elisa,Pecetti, Luciano,Bialy, Zbigniew,Jurzysta, Marian
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experimental part
p. 2826 - 2835
(2010/06/11)
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- Triterpene glycosides from the tubers of Anemone coronaria
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Six new triterpene glycosides (1-6), together with 11 known ones (7-17), have been isolated from a glycoside-enriched fraction prepared from the tubers of Anemone coronaria L. (Ranunculaceae). On the basis of extensive spectroscopic analysis, including 2D
- Mimaki, Yoshihiro,Watanabe, Kazuki,Matsuo, Yukiko,Sakagami, Hiroshi
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experimental part
p. 724 - 729
(2010/02/28)
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- Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A
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(Chemical Equation Presented) Hyptatic acid-A (32), a 2α,3β,24- trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.
- Garcia-Granados, Andres,Lopez, Pilar E.,Melguizo, Enrique,Parra, Andres,Simeo, Yolanda
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p. 3500 - 3509
(2008/02/03)
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- Two new antifungal saponins from the Tibetan herbal medicine Clematis tangutica
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Bioassay-guided fractionation of the ethanol extract of the aerial parts of Clematis tangutica led to the isolation of two new antifungal triterpene saponins. Their structures were determined to be 3-O-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl ester (1) and 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl ester (2) on the basis of spectral data and chemical evidence. Inhibitory activities of the two saponins against seven fungal strains were evaluated. Compounds 1 and 2 showed evident antifungal activity (MIA ≈ 2.5 μg/disc) against Saccharomyces cerevisiae, similar to the positive control amphotericin B and ordinary activities (MIA ≈ 10 μg/disc) against Penicillium avellaneum UC-4376, Candida glabrata, Trichosporon beigelii and Pyricularia oryzae. Compound 2 is a better antifungal agent than compound 1 against most of the fungal strains that were tested.
- Du, Zhizhi,Zhu, Na,Ze-Ren-Wang-Mu, Na,Shen, Yuemao
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p. 547 - 551
(2007/10/03)
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- Metabolism of kalopanaxsaponin K by human intestinal bacteria and antirheumatoid arthritis activity of their metabolites.
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When kalopanaxsaponin K (KPK) from Kalopanax pictus was incubated for 24 h at 37 degrees C with human intestinal microflora, KPK was mainly metabolized to kalopanaxsaponin I (KPI) via kalopanaxsaponin H (KPH) rather than via kalopanaxsaponin J (KPJ), and then transformed to kalopanaxsaponin A (KPA) and hederagenin. Bacteroides sp., and Bifidobacterium sp. and Fusobacterium sp. transformed KPK to KPI and KPA and hederagenin via KPH or KPJ. However, Lactobacillus sp. and Streptococcus sp. transformed KPK to KPI, KPA, and hederagenin only via KPJ. The metabolite KPA of KPK showed potent antirheumatoid arthritis activity.
- Kim, Dong-Hyun,Bae, Eun-Ah,Han, Myung Joo,Park, Hee-Juhn,Choi, Jong-Won
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- Triterpenoid glycosides of Fatsia japonica. II. Isolation and structure of glycosides from the leaves
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The previously known triterpenoid 3-O-α-L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ethers of the 3-O-α-L-arabinopyranoside of hederagenin, and 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves of Fatsia japonica (Araliaceae). The structures of the glycosides are confirmed by chemical methods and 13C NMR spectroscopy.
- Grishkovets,Sobolev,Shashkov,Chirva
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p. 501 - 505
(2007/10/03)
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- Triterpenoid glycosides from Decaisnea fargesii Franch
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A new triterpenoid glycoside, 3-O-β-D-xylopyranosyl (1 → 3)-α-L- rhamnopyranosyl (1 → 2)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl (1 → 4)-β-D-glucopyranosyl (1 → 6)-β-D-glucopyranoside 1, named decaisoside F, has been isolated from the seeds of Decaisnea fargesii along with two known compounds, decaisoside D 2 and decaisoside E 3. Their structures have been elucidated on basis of chemical methods and spectral data (FABMS, 1H NMR, 13C NMR. DEPT and COSY).
- Kong, Jie,Yang, Xiaohui,Lu, Runhua,Wang, Yunpu,Wang, Hanqing
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p. 882 - 884
(2007/10/03)
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- Metabolism of kalopanaxsaponin B and H by human intestinal bacteria and antidiabetic activity of their metabolites
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To investigate the relationship between the intestinal bacterial metabolism of kalopanaxsaponin B and H from Kalopanax pictus (Araliaceae), and their antidiabetic effect, kalopanaxsaponin B and H were metabolized by human intestinal microflora and the antidiabetic activity of their metabolites was measured. Human intestinal microflora metabolized kalopanaxsaponin B to kalopanaxsaponin A, hederagenin 3-O-α-L- arabinopyranoside and hederagenin. The main metabolites of kalopanaxsaponin B were kalopanaxsaponin A and hederagenin. Kalopanaxsaponin H was metabolized to kalopanaxsaponin A and I, hederagenin 3-O-α-L-arabinopyranoside and hederagenin. The main metabolites of kalopanaxsaponin H were kalopanaxsaponin I and hederagenin. Among kalopanaxsaponin B, H and their metabolites, kalopanaxsaponin A showed the most potent antidiabetic activity, followed by hederagenin. However, the main components, kalopanaxsaponin B and H, in K. pictus were inactive.
- Kim, Dong-Hyun,Yu, Ki-Woong,Bae, Eun-Ah,Park, Hee-Juhn,Choi, Jong-Won
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p. 360 - 365
(2007/10/03)
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- Leonticins A-C three octasaccharide saponins from Leontice kiangnanensis
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Three octasaccharide saponins, leonticins A, B, and C (1-3), were isolated from the tubers of Leontice kiangnanensis. Their structures were elucidated by a combination of chemical degradation and spectral methods including negative FABMS and NMR measurements as 3-O-β-D-glucopyranosyl(1→ 2)-α-L-arabinopyranosylhederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D- glucopyranosyl(1→6)-β-D-glucopyranosyl(1→4)-α-L-rhamnopyranosyl(1→4)- β-D-glucopyranosyl(1→6)-β-D-glucopyranoside (1), 3-O-[β-D- xylopyranosyl(1→3)-β-D-galactopyranosyl(1→4)-β-D- glucopyranosyl(1→3)][β-D-glucopyranosyl(1→2)]-α-L- arabinopyranosyloleanolic acid 28-O-α-L-rhamnopyranosyl(1→4)-β-D- glucopyranosyl(1→6)-β-D-glucopyranoside (2), and 3-O-[β-D- xylopyranosyl(1→3)-β-D-galactopyranosyl(1→4)-β-D- glucopyranosyl(1→3)][β-D-glucopyranosyl(1→2)-α-L- arabinopyranosylechinocystic acid 28-O-α-L-rhamnopyranosyl(1→4)-β-D- glucopyranosyl(1→6)-β-D-glucopyranoside (3), respectively. The complete assignments of the proton and carbon resonances for 1-3 were achieved based on extensive 2D NMR analysis (DQF-COSY, TOCSY, ROESY, HSQC, and HMBC).
- Chen, Min,Wu, Wei Wei,Sticher, Otto,Nanz, Daniel
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p. 722 - 728
(2007/10/03)
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- PATENSIN, A SAPONIN FROM PULSATILLA PATENS VAR. MULTIFIDA
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Patensin, a new triterpenoid glycoside, was isolated from the ethanolic extraction of the roots of Pulsatilla patens var. multifida.Its stucture was established as hederagenin 3-O-β-D-galactopyranosyl-(1 --> 2)-β-D- glucopyranoside on the basis of hydrolysis and spectral evidence including 1D and 2D NMR techniques. - Key words: Pulsatilla patens var. multifida; Ranunculaceae; triterpenoid glycoside; patensin.
- Ye, Wen-Cai,Ou, Bo-Xin,Ji, Nine-Ning,Zhao, Shou-Xun,Ye, Tao,et al.
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p. 937 - 940
(2007/10/02)
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- Thermal Degradation of Glycosides, V - Hydrothermolysis of Triterpenoid and Steroid Glycosides
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In this paper the hydrothermolysis of triterpenoid and steroid glycosides is described.By mere heating with water or water/1,4-dioxane solution, the triterpenoid and steroid glycosides 1, 4 and 15, 16, 25, 29, respectively, are converted into their aglycones and prosapogenins.Furthermore, hydrothermolysis of the triterpenoid 3,28-O-bisglycosides 5, 6, 8, 9, 12 affords the corresponding 3-O-glycosides and reduced oligosaccharides formed by selective cleavage of the ester glycosidic linkage.It is expected that this hydrothermolysis is useful for the structure determination of some triterpenoid and steroid glycosides and for yielding new oligosaccharides.The hydrothermolyzed products have been isolated by chromatography and their structures elucidated by spectroscopic methods.Key Words: Degradation, thermal / Thermolysis / Glycosides / Carbohydrates / Triterpenoids / Steroids
- Kim, Youn Chul,Higuchi, Ryuichi,Komori, Tetsuya
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p. 453 - 460
(2007/10/02)
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- Degradation of Cardenolide Glycosides
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The thermal degradation of cardenolide glycosides consisting of different sugar moieties and aglycones was examined.On simple heating, the sugar - aglycone linkage of cardenolide glycosides having 2,6-dideoxy sugar moieties is readily cleaved, to afford their genuine aglycones.On the contrary, cardenolide glycosides possessing 6-deoxy sugar moieties are resistant to the degradative reaction.Besides the fission of the glycosidic linkages, some interesting reactions also took place.The pyrolyzed products were isolated by chromatography, and the structures were elucidated by spectroscopic evidence.
- Kim, Youn Chul,Higuchi, Ryuichi,Komori, Tetsuya,Abe, Fumiko,Yamauchi, Tatsuo
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p. 943 - 947
(2007/10/02)
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- SAPONINS FROM ROOTS OF KALOPANAX SEPTEMLOBUS (THUNB.) KOIDZ., CIQIU: STRUCTURES OF KALOPANAX-SAPONINS C, D, E AND F
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Four new triterpenoid saponins named kalopanax-saponins C (4), D (5), E (6) and F (7) were isolated from the roots of Kalopanax septemlobus (THUNB.) KOIDZ. together with three known saponins, kalopanax-saponins A (1) and B (2), and chikusetsusaponin IV (3).On the basis of chemical and spectral data, the structures of these new saponins were elucidated to be as follows: (4), 3-O-α-rhamnopyranosyl-(1->2)-3)>-α-arabinopyranosyl hederagenin 28-O-α-rhamnopyranosyl-(1->4)-β-glucopyranosyl-(1->6)-β-glucopyranosyl ester; (5), 3-O-α-rhamnopyranosyl-(1->2)-3)>-α-arabinopyranosyl oleanolic acid 28-O-α-rhamnopyranosyl-(1->4)-β-glucopyranosyl-(1->6)-β-glucopyranosyl ester; (6), 3-O-β-glucopyranosyl-(1->3)-β-glucuronopyranosyl oleanolic acid; (7), 3-O-α-arabinopyranosyl-(1->2)-3)>-β-glucuronopyranosyl oleanolic acid 28-O-β-glucopyranosyl ester.Keywords - Kalopanax septemlobus; Araliaceae; saponin; kalopanax-saponin; oleanolic acid glycoside; hederagenin glycoside; Chinese folk medicine; ciqiu
- Shao, Chun-Jie,Kasai, Ryoji,Xu, Jing-Da,Tanaka, Osamu
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p. 311 - 314
(2007/10/02)
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- Thermal Degradation of Glycosides, II. - Thermal Effect on Acetates of Typical Triterpenoid and Steroid Glycosides
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The thermal effect on acetates of triterpenoid and steroid glycosides was examined.Contrary to the case of free glycosides, on heating the acetates of typical triterpenoid and steroid glycosides (including cardiac glycosides) on a melting point apparatus the cleavage reactions of sugar-aglycone and sugar-sugar linkage did not take place, and no aglycones or prosapogenins were obtained.However, two interesting and useful reactions did occur in the course of thermolysis of cardiac glycoside acetates.By taking into account the thermal effect on the glycoside acetates, and their FD mass spectra, an important suggestion on the mechanism of FD mass fragmentation of the glycosidic linkage was obtained.
- Higuchi, Ryuichi,Noguchi, Yuko,Kitamura, Yoichi,Kim, Youn Chul,Komori, Tetsuya
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p. 775 - 780
(2007/10/02)
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- TRITERPENE GLYCOSIDES OF ALFALFA. III. MEDICOSIDE I
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On the basis of chemical transformations and with the aid of physicochemical results, the structure of glycoside I isolated from the roots of the plant Medicago sativa has been established as hederagin 3-O-2)-β-D-glucopyranosyl(1->2)-α-L-arabinopyranoside> 28-O-β-D-glucopyranoside.Compound (I), C52H84O22, mp 210-212 deg C, D21 +38.4 deg (c 1.48; methanol).Acid hydrolysis of (I) led to hederogenin (II) - C30H48O4, mp 326-330 deg C, D23 +84.2 deg (c 0.19; pyridine).The Hakomori methylation of glycoside (I) yielded the permethylate (IV) - C65H11O22 D23 +41.6 deg (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-arabinopyranose, and 2,3,4-tri-O-methyl-L-arabinopyranose.The alkaline hydrolysis of glycoside I gave compound (III) with mp 230-233 deg C, D21 +35.2 deg (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).
- Timbekova, A. E.,Abubakirov, N. K.
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p. 571 - 574
(2007/10/02)
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- On the Structure of Saponins from Astrantia major L. Part 38: On the Knowledge of the Constituents of Some Saniculoideae
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From fresh plant material of Astrantia major L. a complex of saponins was isolated and separated into its main components.The complex comtains mono- and bisdesmosides with triterpene acids as aglycon.The dominating part of glycosides at C-3 of the aglyca is the 3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside linked with hederagenin (α-hederin) or oleanolic acid (β-hederin) and bisdesmosidically as hederagenin-28-O-L-rhamnopyranosylester (hederasaponin C) and as hederagenin-28-O-D-glucopyranosyl-(1->6)-D-glucopyranosylester (diipsacosid B).Furthermore a gypsogenic acid-3-O-D-glucopyranosyl-(1->2)-glucopyranosid was identified.
- Hiller, K.,Adler, Claudia,Galetzka, G.,Franke, P.,Gruendemann, E.,Hille, J.
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p. 343 - 345
(2007/10/02)
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- A TRITERPENOID SAPONIN FROM FICARIA RANUNCULOIDES TUBERS
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One of the minor saponins extracted from the tubers of Ficaria ranunculoides and purified by fermentation may be 3-O-(α-arabinopyranosyl-1')28-O-6''(α-rhamnopyranosyl-1'''->4'')β-glucopyranosyl-1''>-hederagenin.On the basis of chemical degradation and spectral analysis, the structure of this new saponin is proposed. Key Word Index - Ficaria ranunculoides; Ranunculaceae; triterpenoid saponin; 3-O-(α-arabinopyranosyl-1')28-O-6''(α-rhamnopyranosyl-1'''->4'')β-glucopyranosyl 1''>-hederagenin.
- Texier, O.,Ahond, A.,Regerat, F.,Pourrat, H.
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p. 2903 - 2906
(2007/10/02)
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- TRITERPENE GLYCOSIDES OF Climacoptera transoxana. III. THE STRUCTURES OF COPTEROSIDES E AND F
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New triterpene glycosides have been isolated from the epigeal part of Climacoptera transoxana (Iljin) Botsch. - copterosides E and F.According to chemical transformations and physicochemical characteristics, copteroside E has the structure of oleanolic acid 28-O-β-D-glucopyranoside 3-O-2)>-4)>-β-D-glucuronopyranoside> and copteroside F that of hederagenin 28-O-β-D-glucopyranoside 3-O-2)>-4)>-β-D-glucopyranoside>.
- Annaev, Ch.,Isaev, M. I.,Abubakirov, N. K.
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p. 560 - 564
(2007/10/02)
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