17184-21-3Relevant academic research and scientific papers
A TRITERPENOID SAPONIN FROM FICARIA RANUNCULOIDES TUBERS
Texier, O.,Ahond, A.,Regerat, F.,Pourrat, H.
, p. 2903 - 2906 (1984)
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.
Cytotoxic and immunomodulator potential of hederagenin saponins from Cephalaria tchihatchewii
Sarikahya, Nazli Boke,Mkouboi, Mohamed Chanfiou,Nalbantsoy, Ayse,Elibol, Murat
, p. 216 - 221 (2021)
Two newly described oleanane-type saponins (1–2), named tchihatchewosides A–B, along with thirteen known compounds, were isolated from the aerial parts of Cephalaria tchihatchewii using several type of chromatography processes. The structures of all compounds (1-15) were determined by spectroscopic (1D- and 2D-NMR, HR-ESI/MS) and chemical methods. The cytotoxic activities on CCD 34Lu, A549, CRL5807, CRL 5826, HTB-177 and HeLa cell lines of newly described compounds 1–2 and 1a-2a were evaluated by MTT method using doxorubicin as positive control. Immunomodulatory activity was performed with PMA plus ionomycin in stimulated whole blood cells treated with saponins. The supernatant was analyzed for IL-4, IFN-γ and IL1β cytokines by ELISA. DMSO was considered as the negative control. The results showed that the only compound 1a was exhibited moderate cytotoxicity against CRL 5826 and CCD 34Lu cells. The compounds 1–2 and prosapogenins 1a-2a stimulated IL1β cytokine release, indicating that they might potentially stimulate the innate immune response.
Antibacterial activity of a triterpenoid saponin from the stems of Caesalpinia pulcherrima Linn.
Asati, Nidhi,Yadava
, p. 499 - 507 (2017/09/30)
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.
Impact of Scaffold Exploration on Novel Dual-Acting Histone Deacetylases and Phosphodiesterase 5 Inhibitors for the Treatment of Alzheimer’s Disease
Sánchez-Arias, Juan A.,Rabal, Obdulia,Cuadrado-Tejedor, Mar,De Miguel, Irene,Pérez-González, Marta,Ugarte, Ana,Sáez, Elena,Espelosin, Maria,Ursua, Susana,Haizhong, Tan,Wei, Wu,Musheng, Xu,Garcia-Osta, Ana,Oyarzabal, Julen
, p. 638 - 661 (2017/03/20)
A novel systems therapeutics approach, involving simultaneous inhibition of phosphodiesterase 5 (PDE5) and histone deacetylase (HDAC), has been validated as a potentially novel therapeutic strategy for the treatment of Alzheimer’s disease (AD). First-in-class dual inhibitors bearing a sildenafil core have been very recently reported, and the lead molecule 7 has proven this strategy in AD animal models. Because scaffolds may play a critical role in primary activities and ADME-Tox profiling as well as on intellectual property, we have explored alternative scaffolds (vardenafil- and tadalafil-based cores) and evaluated their impact on critical parameters such as primary activities, permeability, toxicity, and in vivo (pharmacokinetics and functional response in hippocampus) to identify a potential alternative lead molecule bearing a different chemotype for in vivo testing.
Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis
Wang, Xiao-Yang,Gao, Hui,Zhang, Wei,Li, Yuan,Cheng, Guang,Sun, Xiao-Li,Tang, Hai-Feng
, p. 5714 - 5720 (2013/10/01)
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.
Drug to genome to drug: Discovery of new antiplasmodial compounds
Beghyn, Terence B.,Charton, Julie,Leroux, Florence,Laconde, Guillaume,Bourin, Arnaud,Cos, Paul,Maes, Louis,Deprez, Benoit
, p. 3222 - 3240 (2011/06/27)
Figure Presented. The dominant strategy for discovery of new antimalarial drugs relies on cell-free assays on specific biochemical pathways of Plasmodium falciparum. However, it appears that screening directly on the parasite is a more rewarding approach. The drug to genome to drug approach consists of testing a small set of structural analogues of a drug acting on human proteins that have plasmodial orthologues. Both man and plasmodium possess cyclic nucleotide phosphodiesterases (PDEs) that are key players of cell homeostasis. We synthesized and tested 40 analogues of tadalafil, a human PDE5 inhibitor, on P. falciparum in culture and obtained potent inhibitors of parasite growth. We discuss the structure-activity relationships, which support the hypothesis that our compounds kill the parasite via inhibition of plasmodial PDE activity. We also prove that antiplasmodial derivatives inhibit the hydrolysis of cyclic nucleotides of the parasite, validating the cAMP/cGMP pathways as therapeutic targets against Plasmodium falciparum.
Triterpene glycosides from the underground parts of caulophyllum thalictroides
Matsuo, Yukiko,Watanabe, Kazuki,Mimaki, Yoshihiro
experimental part, p. 1155 - 1160 (2011/03/21)
A total of 22 triterpene glycosides, including 10 new compounds (1-10), were isolated from the underground parts of Caulophyllum thalictroides. The structures of the new glycosides were determined on the basis of extensive spectroscopic analyses, including two-dimensional (2D) NMR data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. All 22 compounds were evaluated for cytotoxicity against HL-60 human leukemia cells. The triterpene monodesmosides based on oleanolic acid (1 and 11-16) showed cytotoxic activity against HL-60 cells with IC50 values that ranged from 3.4 to 15.9 μg/mL.
PDE5 inhibitors: An original access to novel potent arylated analogues of tadalafil
Beghyn, Terence,Hounsou, Candide,Deprez, Benoit P.
, p. 789 - 792 (2007/10/03)
A method to access totally new analogues of tadalafil was explored. The Buchwald reaction was adapted and used to replace the methyl group of tadalafil by various aryl groups. Inhibition potencies on PDE5 of these analogues were determined and proved to be comparable to the one of tadalafil. Using the same route, compounds with the same level of activity but improved water solubility were produced by introducing a pyridine or a pyrimidine ring. This original route also opens access to new unpatented compounds.
Triterpene glycosides from Kalopanax septemlobum. 1. Glycosides A, B, C, F, G1, G2, I2, H, and J from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea
Grishkovets,Panov,Kachala,Shashkov
, p. 194 - 199 (2008/02/01)
Eight known glycosides of hederagenin and the new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2) -O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin were isolated by chromatographic methods from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea. The known 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin was observed for the first time in Kalopanax septemlobum. 2005 Springer Science + Business Media, Inc.
Two new antifungal saponins from the Tibetan herbal medicine Clematis tangutica
Du, Zhizhi,Zhu, Na,Ze-Ren-Wang-Mu, Na,Shen, Yuemao
, p. 547 - 551 (2007/10/03)
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.
