465-00-9Relevant articles and documents
New triterpenoid saponin glycosides from the fruit fibers of: Trichosanthes cucumerina L.
Chulrik, Wanatsanan,Chunglok, Warangkana,Li, Jian-Xin,Suebsakwong, Parichat,Suksamrarn, Apichart,Yao, Zhu-Jun
, p. 10461 - 10470 (2020/03/27)
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.
Artefact formation during acid hydrolysis of saponins from Medicago spp.
Tava, Aldo,Biazzi, Elisa,Mella, Mariella,Quadrelli, Paolo,Avato, Pinarosa
, p. 116 - 127 (2017/04/13)
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.
A new biologically active triterpenoid saponin from the aerial parts of Neanotis wightiana
Das, Niranjan,Ghosh, Partha Sarathi,Das, Manash Chandra,Dinda, Biswanath
, p. 270 - 273 (2013/08/25)
Phytochemical investigation of the aerial parts of Neanotis wightiana for the first time has led to the isolation of one new triterpenoid saponin, neanoside A (1), along with seven known compounds, oleanolic acid (2), ursolic acid (3), β-sitosterol (4) and its glucoside (5), stigmasterol (6) and its glucoside (7) and hexacosanoic acid (8). The structures of these compounds were elucidated by means of spectroscopic (NMR, MS and other) and chemical techniques as well as comparison with literature data. The structure of 1 was elucidated as 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl (1 → 3)-β-d-glucopyranosyl bayogenin. The in vitro biochemical analysis of compound 1 against the activity of human serum liposomal enzymes, SGOT (serum glutamate oxaloacetate transaminase), SGPT (serum glutamate pyruvate transaminase) and ALP (alkaline phosphatase) and glycerol kinase showed significant reduction of their activity.
Oleanane saponins from Bellis sylvestris Cyr. and evaluation of their phytotoxicity on Aegilops geniculata Roth
Scognamiglio, Monica,D'Abrosca, Brigida,Fiumano, Vittorio,Chambery, Angela,Severino, Valeria,Tsafantakis, Nikolaos,Pacifico, Severina,Esposito, Assunta,Fiorentino, Antonio
, p. 125 - 134,10 (2012/12/12)
Six oleanane saponins were isolated for the first time from leaves of Bellis sylvestris Cyr., the southern daisy. Their structures were established by the extensive use of 2D-NMR experiments, including COSY, TOCSY, NOESY, HSQC, HMBC, CIGAR, H2BC, and HSQC-TOCSY, along with Q-TOF HRMS2 analysis. All of the compounds are constituted by bayogenin as aglycone, and characterized by the presence of an oligosaccharide moiety, consisting of two to four sugar unities esterified at the C-28 carboxyl carbon. One of the isolated compounds is a bisdesmoside containing an additional sugar moiety at the C-3 carbon. The phytotoxic activity assayed against Aegilops geniculata Roth., a coexisting test species, has been evaluated revealing that all the compounds, at the highest concentrations, showed strong phytotoxicity against the leaf development.
A new complex triterpenoid saponin from Samanea saman with haemolytic activity and adjuvant effect
Barbosa, Antony De Paula,Da Silva, Bernadete Pereira,Parente, José Paz
experimental part, p. 626 - 631 (2012/10/07)
A new complex triterpenoid saponin was isolated from the stem bark of Samanea saman by using chromatographic methods. Its structure was established as 3-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]-2,23-dihydroxy- (2β,3β,4α)-olean-12-en-28-oic acid O-β-d-glucopyranosyl-(1 → 3)-O-[O-β-d-glucopyranosyl-(1 → 4)]-O-6-deoxy-α-l- mannopyranosyl-(1 → 2)-6-O-[4-O-[(2E,6S)-2,6-dimethyl-1-oxo-2,7-octadienyl] -6-deoxy-α-l-mannopyranosyl)oxy]-β-d-glucopyranosyl ester (1). Structural elucidation was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques and chemical conversions. The haemolytic activity of the saponin was evaluated using in vitro assays, and its adjuvant potential on the cellular immune response against ovalbumin antigen was investigated using in vivo models.
Medicinal flowers. XXXII.1) Structures of oleanane-type triterpene saponins, perennisosides VIII, IX, X, XI, and XII, from the flowers of Bellis perennis
Morikawa, Toshio,Li, Xuezheng,Nishida, Eriko,Nakamura, Seikou,Ninomiya, Kiyofumi,Matsuda, Hisashi,Hamao, Makoto,Muraoka, Osamu,Hayakawa, Takao,Yoshikawa, Masayuki
experimental part, p. 889 - 895 (2011/08/21)
Five new triterpene saponins perennisosides VIII (1), IX (2), X (3), XI (4), and XII (5) were isolated from the MeOH-eluated fraction of the methanolic extract from the flowers of Bellis perennis. The MeOH-eluted fraction of the methanolic extract from the flowers of B. perennis was found to inhibit gastric emptying in olive oil-loaded mice at a dose of 200 mg/kg, per os (p.o.). The stereostructures of 1-5 were elucidated on the basis of chemical and spectroscopic evidence.
Triterpene glycosides from the tubers of Anemone coronaria
Mimaki, Yoshihiro,Watanabe, Kazuki,Matsuo, Yukiko,Sakagami, Hiroshi
experimental part, p. 724 - 729 (2010/02/28)
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
Cytotoxic 16-β-[(d-xylopyranosyl)oxy]oxohexadecanyl triterpene glycosides from a Malagasy plant, Physena sessiliflora
Inoue, Masaki,Ohtani, Kazuhiro,Kasai, Ryoji,Okukubo, Mayu,Andriantsiferana, Marta,Yamasaki, Kazuo,Koike, Tohru
experimental part, p. 1195 - 1202 (2010/06/21)
Brine shrimp lethality assay-guided separation of the MeOH extract of leaves of Physena sessiliflora, which is endemic to Madagascar, afforded eight triterpene glycosides, Physenoside S1-4 and 16-β-[(d-xylopyranosyl)oxy]oxohexadecanyl homologues, Physenos
New saponins from Sechium mexicanum
Hernandez-Carlos, Beatriz,Carmona-Pineda, Miriam,Villanueva-Canongo, Claudia,Lopez-Olguin, Jesus F.,Aragon-Garcia, Agustin,Joseph-Nathan, Pedro
experimental part, p. 994 - 1003 (2010/06/15)
The chemical study of Sechium mexicanum roots led to the isolation of the two new saponins {3-0-β-d-glucopyranosyl (1→3)-β-d- glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-0-α-l-rhamnopyranosyl-(1→3)-β-d- xylopyranosyl-(1→4)- α-l-rham
New triterpenic saponins from the aerial parts of Medicago arabica (L.) Huds
Tava, Aldo,Mella, Mariella,Avato, Pinarosa,Biazzi, Elisa,Pecetti, Luciano,Bialy, Zbigniew,Jurzysta, Marian
experimental part, p. 2826 - 2835 (2010/06/11)
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.
