3615-37-0Relevant articles and documents
Pro-apoptotic activity of new triterpenoid saponins from the roots of Albizia adianthifolia (Schumach.) W.Wight
Noté, Olivier Placide,Kamto, Eutrophe Le Doux,Toukea, Daniel Djou,Aouazou, Sarah Ali,Mbing, Joséphine Ngo,Muller, Christian Dominique,Guillaume, Dominique,Pegnyemb, Dieudonné Emmanuel
, p. 34 - 41 (2018)
As part of our study of the proapoptotic function of saponins from Cameroonian's Albizia genus, phytochemical investigation of the roots of Albizia adianthifolia led to the isolation of three new triterpenoid saponins, named adianthifoliosides G–I (1–3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid-28-O-β-D-xylopyranosyl-(1 → 3)-[5-O-acetyl-α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (1), 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (2), and 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-β-D-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (3). The apoptotic effect of saponins 1–3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1–3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner.
Three new spirostanol glycosides from Helleborus thibetanus
Li, Zhang-Peng,Su, Yan-Fang,Wei, Zi-Ye,Yang, Feng-Ying,Zhang, Hui
, p. 975 - 980 (2020)
An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1–3). Their structures were elucidated by extensive analysis of 1 D, 2 D NMR spectra, together with IR and MS met
Glycosides of polygalacic acid from the stem barks of Piper guineense Schum and Thonn
Le Doux Kamto, Eutrophe,Noté, Olivier Placide,Kinyok, Mc Jesus,Wilhelm, Anke,Mbing, Joséphine Ngo,Antheaume, Cyril,de Théodore Atchadé, Alex,Pegnyemb, Dieudonné Emmanuel,Ndinteh, Derek Tantoh,Haddad, Mohamed,Bonnet, Susan L.
, (2021)
In a continuation of our study on constituents of P. guineense now focusing on the search for saponins, phytochemical investigation of the n-BuOH fraction of P. guineense stem bark led to the isolation of three previously undescribed triterpenoid saponins, named guineenosides A─C (1─3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (1), 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (2), and 3-O-{α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-[α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (3). This is the first report of triterpenoid saponins from P. guineense.
Dolabellane diterpene and three cycloartane glycosides from Thalictrum squarrosum
Yoshimitsu, Hitoshi,Miyashita, Hiroyuki,Nishida, Makiko,Mineno, Tomoko,Nohara, Toshihiro
, p. 1043 - 1046 (2010)
A new dolabellane diterpene glycoside, named squoside A, and three new cycloartane glycosides, named squarrosides V, VI, and VII, have been isolated from the dried aerial parts of Thalictrum squarrosum (Ranunculaceae). Their structures were determined by
Flavonoids isolated from the fresh sweet fruit of Averrhoa carambola, commonly known as star fruit
Jia, Xuchao,Xie, Haihui,Jiang, Yueming,Wei, Xiaoyi
, p. 156 - 162 (2018)
Thirteen flavonoids were isolated from the fresh sweet fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit, and their structures were determined by spectroscopic and chemical methods. 8-Carboxymethyl-(+)-epicatechin methyl ester, pinobanksin 3-O-β-D-glucoside, and carambolasides M–Q were undescribed structures. (+)-Epicatechin, aromadendrin 3-O-β-D-glucoside, helicioside A, taxifolin 3′-O-β-D-glucoside, galangin 3-O-rutinoside, and isorhamnetin 3-O-rutinoside were reported from this species for the first time. Pinobanksin 3-O-β-D-glucoside and carambolasides M–Q showed more potent 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation scavenging activity (IC50 = 5.3–2.3 μM) than L-ascorbic acid (10.5 μM). Further, (+)-epicatechin, pinobanksin 3-O-β-D-glucoside, isorhamnetin 3-O-rutinoside, and carambolasides O–Q exhibited weak porcine pancreatic lipase inhibitory activity.
Bisdesmosidic saponins from securidaca longepedunculata roots: Evaluation of deterrency and toxicity to coleopteran storage pests
Stevenson, Philip C.,Dayarathna, Thamara K.,Belmain, Steven R.,Veitch, Nigel C.
, p. 8860 - 8867 (2009)
Powdered dry root bark of Securidaca longepedunculata was mixed with maize and cowpea and effectively reduced the numbers of Sitophilus zeamais and Callosobruchus maculatus emerging from these commodities, respectively, more than 9 months after treatment.
Cylindroside A, a new triterpenoid saponin from Cylindrokelupha dalatensis and its cytotoxic activity
Zhou, Wen-Bin,Liu, Jie,Xing, Shuang,Zhang, Yun,Xiong, Guo-Ling,Luo, Qing-Liang,Ma, Bai-Ping,Yang, Ming-Hui,Liu, Ping
, p. 1277 - 1283 (2013)
A new triterpenoid saponin, named cylindroside A (1), was isolated from the seeds of Cylindrokelupha dalatensis (Kosterm.) T.L. Wu by using chromatographic method. The structure of 1 was established by comprehensive spectroscopic analysis and chemical degradation. Compound 1 displayed significant antitumor activity in vitro against BCG and MCF-7 cancer cell lines and IC50 values were 4.17 ± 0.23 and 3.07 ± 0.66 μM by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method, respectively.
Heptyl vicianoside and methyl caramboside from sour star fruit
Yang, Dan,Jia, Xuchao,Xie, Haihui
, p. 1 - 4 (2018)
Two new alkyl glycosides, heptyl vicianoside (1) and methyl 2-O-β-d-fucopyranosyl-α-l-arabinofuranoside (methyl caramboside, 4), were isolated from the sour fruit of Averrhoa carambola L. (Oxalidaceae), along with octyl vicianoside (2), cis-3-hexenyl rutinoside (3), and methyl α-d-fructofuranoside (5). Their structures were determined by spectroscopic and chemical methods. Compounds 2, 3, and 5 were obtained from the genus Averrhoa for the first time. All the compounds were evaluated for in vitro α-glucosidase, pancreatic lipase, and acetylcholinesterase inhibitory activities, but none of them were potent.
Three new cytotoxic oleanane triterpenoid saponins from Cylindrokelupha dalatensis
Yan, Meng-Yun,Liu, Jie,Xing, Shuang,Xiong, Guo-Ling,Pei, Ling-Peng,Ma, Bai-Ping,Liu, Ping,Zhou, Wen-Bin
, p. 770 - 780 (2018)
Three new minor oleanane triterpenoid saponins, cylindrosides B (1), C (2), and D (3), were isolated from the seed of Cylindrokelupha dalatensis using chromatographic method. Their structures were established on the basis of the chemical and spectroscopic evidences. They displayed significant antitumor activity in vitro against HL60 cancer cell lines and IC50 values were 7.15?±?0.63, 10.07?±?0.97, and 4.74?±?0.57?μM, respectively, by MTT method.
New acylated triterpene saponins from the roots of Securidaca inappendiculata Hassk
Zha, Haiyan,Wang, Zhi,Yang, Xuedong,Jin, Daqing,Hu, Licui,Zheng, Wenfeng,Xu, Lizhen,Yang, Shilin
, p. 108 - 113 (2015)
Two new acylated triterpene saponins, named as securioside C (1), securioside D (2), and one pair of isomers 3/4, the (Z)-isomer securioside E (3) being new, together with a known triterpene saponin polygalasaponin XLIV (4) were isolated from the roots of Securidaca inappendiculata Hassk. Their structures were established by HRESIMS, 1D and 2D NMR experiments and comparison of their NMR data with previous reported data. In addition, Compounds 1-2, 3/4, 4 were evaluated for cytotoxicities against LLC (Lewis lung carcinoma) and MCF-7 (human breast cancer) cell lines. Compounds 1 and 2 exhibited moderate cytotoxic activities against LLC cells with IC50 values of 45.56 μM and 85.98 μM.
Isolation of chemical constituents with anti-inflammatory activity from Reineckia carnea herbs
Xu, Xu,Tan, Ting,Zhang, Jing,Li, Zhi-Feng,Yang, Shi-Lin,Wen, Quan,Feng, Yu-Lin
, p. 303 - 315 (2020)
Three new saponins (1–3), a new natural product (4) and six other known compounds (5–10) were isolated from the whole Reineckia carnea plant. Their structures were established by comparison of their NMR spectra and MS data with literature data. In addition, all the isolated compounds were evaluated in vitro for anti-inflammatory activities against LPS-stimulated nitric oxide (NO) production in RAW 264.7 macrophages. Compounds 1–4 exhibited anti-inflammatory activities with IC50 values of 37.5 μM, 31.4 μM, 34.6 μM, and 56.1 μM, respectively. Furthermore, compounds 5–10 showed anti-inflammatory activities with IC50 values ranging from 20.3 to 42.9 μM.
Three new steroidal saponins from Helleborus thibetanus
Zhang, Hui,Su, Yan-Fang,Yang, Feng-Ying
, p. 1724 - 1730 (2016)
Three new steroidal saponins including two spirostanol glycosides (1–2) and one furostanol glycoside 1-sulphate (3) were isolated from the dried roots and rhizomes of Helleborus thibetanus. Structures of the compounds were determined on the basis of extensive use of 1-D and 2-D NMR experiments, together with HR–ESI–MS and IR measurements, as well as the results of acid hydrolysis. Compounds 1–2 represented steroidal saponins with an unusual substitution pattern, which possessed a double bond at C-25 and were glycosylated at 1-OH.
The Arabidopsis At1g45130 and At3g52840 genes encode β-galactosidases with activity toward cell wall polysaccharides
Gantulga, Dashzeveg,Turan, Yusuf,Bevan, David R.,Esen, Asim
, p. 1661 - 1670 (2008)
The Arabidopsis genes At1g45130 and At3g52840 encode the β-galactosidase isozymes Gal-5 and Gal-2 that belong to Glycosyl Hydrolase Family 35 (GH 35). The two enzymes share 60% sequence identity with each other and 38-81% with other plant β-galactosidases that are reported to be involved in cell wall modification. We studied organ-specific expression of the two isozymes. According to our western blot analysis using peptide-specific antibodies, Gal-5 and Gal-2 are most highly expressed in stem and rosette leaves. We show by dot-immunoblotting that Gal-5 and Gal-2 are associated with the cell wall in Arabidopsis. We also report expression of the recombinant enzymes in P. pastoris and describe their substrate specificities. Both enzymes hydrolyze the synthetic substrate para-nitrophenyl-β-d-galactopyranoside and display optimal enzyme activity between pH 4.0 and 4.5, similar to the pH optimum reported for other well-characterized plant β-galactosidases. Both Gal-5 and Gal-2 show a broad specificity for the aglycone moiety and a strict specificity for the glycone moiety in that they prefer galactose and its 6-deoxy analogue, fucose. Both enzymes cleave β-(1, 4) and β-(1, 3) linkages in galacto-oligosaccharides and hydrolyze the pectic fraction of Arabidopsis cell wall. These findings suggest that Gal-5 and Gal-2 could be involved in the modification of cell wall polysaccharides.
Triterpenoid saponins from Albizia lebbeck (L.) Benth and their inhibitory effect on the survival of high grade human brain tumor cells
Noté, Olivier Placide,Jihu, Dong,Antheaume, Cyril,Zeniou, Maria,Pegnyemb, Dieudonné Emmanuel,Guillaume, Dominique,Chneiwess, Hervé,Kilhoffer, Marie Claude,Lobstein, Annelise
, p. 26 - 33 (2015)
As part of our search of new bioactive triterpenoid saponins from Cameroonian Mimosaceae plants, phytochemical investigation of the roots of Albizia lebbeck led to the isolation of two new oleanane-type saponins, named lebbeckosides A-B (1-2). Their structures were established on the basis of extensive 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC, and HMBC) and HRESIMS studies, and by chemical evidence. Compounds 1-2 were evaluated for their inhibitory effect on the metabolism of high grade human brain tumor cells, the human glioblastoma U-87 MG cell lines and the glioblastoma stem-like TG1 cells isolated from a patient tumor, and known to be particularly resistant to standard therapies. The isolated saponins showed significant cytotoxic activity against U-87 MG and TG1 cancer cells with IC50 values of 3.46 μM and 1.36 μM for 1, and 2.10 μM and 2.24 μM for 2, respectively.
A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential
Huang, Linlin,Li, Fei,Li, Quanhong,Liang, Li,Wei, Yunlu,Yu, Guoyong
, (2020/10/02)
The novel natural low-molecular-mass polysaccharide (SLWPP-3) from pumpkin (Cucurbia moschata) was separated from the waste supernatant after macromolecular polysaccharide production and purified using a DEAE cellulose-52 column and gel-filtration chromatography. Chemical and instrumental studies revealed that SLWPP-3 with a molecular mass of 3.5 kDa was composed of rhamnose, glucose, arabinose, galactose and uronic acid with a weight ratio of 1: 1: 4: 6: 15, and primarily contained →3,6)-β-D-Galp-(1→, →4)-α-GalpA-(1→(OMe), →4)-α-GalpA-(1→, →2,4)-α-D-Rhap-(1→, →3)-β-D-Galp-(1→, →4)-α-D-Glcp, and →4)-β-D-Galp residues in the backbone. The branch chain passes were connected to the main chain through the O-4 atom of glucose and O-3 atom of arabinose. Physiologically, the ability of SLWPP-3 to inhibit carbohydrate-digesting enzymes and DPPH and ABTS radicals, as well as protect pancreatic β cells from oxidative damage by decreasing MDA levels and increasing SOD activities, was confirmed. The findings elucidated the structural types of pumpkin polysaccharides and revealed a potential adjuvant natural product with hypoglycemic effects.
