Ardisiacrispin B
(Synonyms: 百两金皂苷B) 目录号 : GC65163Ardisiacrispin B在多因素耐药癌细胞中显示细胞毒性作用,通过铁中毒和凋亡细胞死亡。
Cas No.:112766-96-8
Sample solution is provided at 25 µL, 10mM.
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Ardisiacrispin B displays cytotoxic effects in multi-factorial drug resistant cancer cells via ferroptotic and apoptotic cell death[1].
[1]. Armelle T Mbaveng, et al. A naturally occuring triterpene saponin ardisiacrispin B displayed cytotoxic effects in multi-factorial drug resistant cancer cells via ferroptotic and apoptotic cell death. Phytomedicine. 2018 Apr 1;43:78-85.
Cas No. | 112766-96-8 | SDF | Download SDF |
别名 | 百两金皂苷B | ||
分子式 | C53H86O22 | 分子量 | 1075.24 |
溶解度 | 储存条件 | Store at -20°C, away from moisture and light | |
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1 mg | 5 mg | 10 mg | |
1 mM | 0.93 mL | 4.6501 mL | 9.3002 mL |
5 mM | 0.186 mL | 0.93 mL | 1.86 mL |
10 mM | 0.093 mL | 0.465 mL | 0.93 mL |
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A naturally occuring triterpene saponin Ardisiacrispin B displayed cytotoxic effects in multi-factorial drug resistant cancer cells via ferroptotic and apoptotic cell death
Phytomedicine 2018 Apr 1;43:78-85.PMID:29747757DOI:10.1016/j.phymed.2018.03.035.
Introduction: Multidrug resistance of cancer cells constitutes a serious problem in chemotherapy and a challenging issue in the discovery of new cytotoxic drugs. Many saponins are known to display anti-cancer effects. In this study, the cytotoxicity and the modes of action of a naturally occuring oleanane-type tritepene saponin, Ardisiacrispin B isolated from the fruit of Ardisia kivuensis Taton (Myrsinaceae) was evaluated on a panel of 9 cancer cell lines including various sensitive and drug-resistant phenotypes. Methods: Resazurin reduction assay was used to evaluate cytotoxicity and ferroptotic cell death of samples; caspase-Glo assay was used to detect the activation of caspases in CCRF-CEM leukemia cells. Flow cytometry was used for cell cycle analysis and detection of apoptotic cells by annexin V/PI staining, analysis of mitochondrial membrane potential (MMP) and measurement of reactive oxygen species (ROS). Results: Ardisiacrispin B displayed significant cytotoxic effects in the 9 tested cancer cell lines with IC50 values below 10 µM. The IC50 values ranges were 1.20 µM (towards leukemia CCRF-CEM cells) to 6.76 µM [against heptocarcinoma HepG2 cells] for Ardisiacrispin B and 0.02 µM (against CCRF-CEM cells) to 122.96 µM (against resistant CEM/ADR5000 leukemia cells) for doxorubicin. Collateral sensitivity of resistant HCT116p53-/- colon adenocarcinoma cells to ardisiacripsin B was observed. Ardisiacrispin B induced apoptosis in CCRF-CEM cells via activation of inititator caspases 8 and 9 and effector caspase 3/7, alteration of MMP and increase in ROS production. Ferroptosis also contributed to the cytotoxicity of Ardisiacrispin B. Conclusions: The studied oleanane-type triterpene saponin is a good cytotoxic molecule that deserve more detailed exploration in the future, to develop novel cytotoxic drugs to combat both sensitive and drug-resistant cancers.
Cytotoxic triterpenoid saponins from Lysimachia foenum-graecum
Phytochemistry 2017 Apr;136:165-174.PMID:28173950DOI:10.1016/j.phytochem.2017.01.021.
Eleven oleanane-type triterpenoid saponins, foegraecumosides A-K, and eight known ones, were isolated from the aerial parts of Lysimachia foenum-graecum. Their structures were elucidated by spectroscopic data analyses and chemical methods. All isolated saponins were evaluated for their cytotoxicity against four human cancer cell lines (NCI-H460, MGC-803, HepG2, and T24). Seven saponins containing the aglycone cyclamiretin A exhibited moderate cytotoxicity against all tested human cancer cell lines, with IC50 values of 9.3-24.5 μM. Simultaneously, the cytotoxic activities of foegraecumosides A and B, lysichriside A, ardisiacrispins A and B, cyclaminorin, and 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-α-l-arabinopyranosyl-cyclamiretin A were tested on drug-resistant lung cancer cell lines (A549 and A549/CDDP, respectively). Ardisiacrispin B displayed moderate cytotoxicity against A549/CDDP, with an IC50 value of 8.7 μM and a resistant factor (RF) of 0.9.
Cytotoxic saponins from New Zealand Myrsine species
J Nat Prod 1994 Oct;57(10):1354-60.PMID:7807121DOI:10.1021/np50112a004.
The observed biological activity in two New Zealand Myrsine species has been shown to be due to the presence of triterpene saponins. From Myrsine australis a series of eight oleanane-type saponins was obtained, with compounds 1-4 and 7 and 8 being novel. Also isolated were ardisiacrispin A [5] and Ardisiacrispin B [6]. The structures of the new compounds were determined by chemical and spectroscopic techniques. Extracts of Myrsine salicina yielded only one saponin, 5. Saponins 1-8 were shown to be combinations of four oleanane triterpenes bonded to beta-D-xylp(1-->2)-beta-D-glcp(1-->4)-[beta-D-glcp(1-->2)]-alpha-L -arap (compounds 1, 3, 5, 7) and this same tetrasaccharide with alpha-L-rhap replacing the beta-D-xylp unit (compounds 2, 4, 6, 8).
Triterpenoid saponins from Ardisia pusilla and their cytotoxic activity
Planta Med 2009 Jan;75(1):70-5.PMID:19039733DOI:10.1055/s-0028-1088369.
Three new triterpenoid saponins 3, 4 and 5, together with two known saponins, Ardisiacrispin B (1) and ardisiacrispin A (2), were isolated from the whole plants of Ardisia pusilla A. DC. Their structures were elucidated by extensive spectral analysis and chemical evidence. Compound 3 is a hexaglycoside with a 13,28-epoxyoleanane type aglycone, while both 4 and 5 are triterpenoid tetraglycosides related to the olean-12-ene skeleton. Saponins 1-4 exhibited significant cytotoxicity against human glioblastoma U251MG cells, but did not affect the growth of primary cultured human astrocytes.
Molecular phylogeny, structure modeling and in silico screening of putative inhibitors of aerolysin of Aeromonas hydrophila EUS112
J Biomol Struct Dyn 2022;40(19):8840-8849.PMID:33931004DOI:10.1080/07391102.2021.1918254.
Aeromonas hydrophila, a Gram-negative bacterium, causes diseases in fish, resulting in excessive loss to the aquaculture industry. Aeromonas is a highly heterogeneous group of bacteria, and the heterogeneity of the genus is attributed to variation and diversity in the virulence factors and toxins among various Aeromonas strains. One of the major toxins aerolysin, secreted by the bacterium, causes hemorrhagic-septicemia and diarrhea and can serve as a drug target. Here, we describe characterization, molecular phylogeny, and homology modeling of the aerolysin of A. hydrophila strain EUS112 (AhEUS112) cloned in our lab. The encoded aerolysin is 485 amino acids long with an N-terminal signal sequence of 23 amino acids. Phylogenetic analysis of the aerolysin of AhEUS112 revealed that it belongs to a diverse group of toxins, showing maximum similarity with aerolysins of other Aeromonas strains followed by Vibrio toxin. The homology model of the mature aerolysin of AhEUS112 was generated using the crystal structure of a mutant aerolysin (PDB#3g4n) as the template, which showed that the encoded aerolysin exists as a channel protein. Validation of the generated model using bioinformatics tool confirmed it to be a good quality model that can be used for drug design. Molecular dock analysis revealed that drugs, aralia-saponin I, cyclamin, Ardisiacrispin B, and aralia-saponin II bind to aerolysin with a higher affinity as compared to other drugs and at functionally important amino acids of aerolysin. Hence, these molecules can act as an effective therapeutics for inhibiting the aerolysin pore formation and curtail the severity of Aeromonas infection.Communicated by Ramaswamy H. Sarma.