Ungeremine
(Synonyms: 石蒜碱内铵盐) 目录号 : GC49308
A betaine-type alkaloid with diverse biological activities
Cas No.:2121-12-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Ungeremine is a betaine-type alkaloid that has been found in C. zeylanicum and has diverse biological activities.1,2,3,4 It is an inhibitor of acetylcholinesterase (AChE; IC50 = 0.35 µM).2 Ungeremine acts as a topoisomerase poison, inducing double-strand breaks in DNA by stabilizing the linkage between topoisomerase IIβ and DNA.3 It inhibits the relaxation of supercoiled DNA by human topoisomerase I and -IIα and E. coli topoisomerase I and -IV (IC50s = 6.1, 25.8, 15, and 7.3 µM, respectively).4 Ungeremine inhibits the growth of HL-60, MOLT-4, K562, U937, and LXFL 529L cells (IC50s = 1.3, 0.7, 0.8, 2.5, and 1.2 µM, respectively). It is cytotoxic to a variety of drug-sensitive and -resistant cancer cells (IC50s = 4.89-6.45 and 3.67-75.24 µM, respectively) and induces ferroptosis, necroptosis, apoptosis, and autophagy in CCRF-CEM leukemia cells. Ungeremine (60 mg/kg twice per week) also reduces tumor growth in a GXF251L mouse xenograft model.3
1.Mbaveng, A.T., Bitchagno, G.T.M., Kuete, V., et al.Cytotoxicity of ungeremine towards multi-factorial drug resistant cancer cells and induction of apoptosis, ferroptosis, necroptosis and autophagyPhytomedicine60152832(2019) 2.Rhee, I.K., Appels, N.M.G.M., Hofte, B., et al.Isolation of the acetylcholinesterase inhibitor ungeremine from Nerine bowdenii by preparative HPLC coupled on-line to a flow assay systemBiol. Pharm. Bull.27(11)1804-1809(2004) 3.Barthelmes, H.U., Niederberger, E., Roth, T., et al.Lycobetaine acts as a selective topoisomerase IIβ poison and inhibits the growth of human tumour cellsBr. J. Cancer85(10)1585-1591(2001) 4.Casu, L., Cottiglia, F., Leonti, M., et al.Ungeremine effectively targets mammalian as well as bacterial type I and type II topoisomerasesBioorg. Med. Chem. Lett.21(23)7041-7044(2011)
| Cas No. | 2121-12-2 | SDF | |
| 别名 | 石蒜碱内铵盐 | ||
| Canonical SMILES | OC1=CC2=C(C(CC3)=C1)[N+]3=CC4=CC5=C(OCO5)C=C24 | ||
| 分子式 | C16H12NO3 | 分子量 | 266.3 |
| 溶解度 | Methanol: 10 mg/ml | 储存条件 | -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.7552 mL | 18.7758 mL | 37.5516 mL |
| 5 mM | 0.751 mL | 3.7552 mL | 7.5103 mL |
| 10 mM | 0.3755 mL | 1.8776 mL | 3.7552 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Ungeremine and Its hemisynthesized analogues as bactericides against Flavobacterium columnare
J Agric Food Chem 2013 Feb 13;61(6):1179-83.PMID:23331165DOI:10.1021/jf304586j.
The Gram-negative bacterium Flavobacterium columnare is the cause of columnaris disease, which can occur in channel catfish ( Ictalurus punctatus ). In a previous study, the betaine-type alkaloid Ungeremine, 1, obtained from Pancratium maritimum L. was found to have strong antibacterial activity against F. columnare. In this study, analogues of 1 were evaluated using a rapid bioassay for activity against F. columnare to determine if the analogues might provide greater antibacterial activity and to determine structure-activity relationships of the test compounds. Several Ungeremine analogues were prepared by hydrochlorination of the alkaloid and by selenium dioxide oxidation of both lycorine, 7, and pseudolycorine, 8, which yielded the isomer of Ungeremine, 3, and zefbetaine, 4, respectively. The treatment of lycorine with phosphorus oxychloride allowed the synthesis of an anhydrolycorine lactam, 5, showing, with respect to 1, the deoxygenation and oxygenation of C-2 and C-7 of the C and B rings, respectively. The results of the structure-activity relationship studies showed that the aromatization of the C ring and the oxidation to an azomethine group of C-7 of the B ring are structural features important for antibacterial activity. In addition, the position of the oxygenation of the C ring as well as the presence of the 1,3-dioxole ring joined to the A ring of the pyrrolo[de]phenanthridine skeleton also plays a significant role in imparting antibacterial activity. On the basis of 24-h 50% inhibition concentration (IC(50)) results, Ungeremine hydrochloride, 2, was similar in toxicity to 1, whereas 5 had the lowest activity. Analogue 2 is soluble in water, which may provide the benefit for use as an effective feed additive or therapeutant compared to Ungeremine.
Ungeremine effectively targets mammalian as well as bacterial type I and type II topoisomerases
Bioorg Med Chem Lett 2011 Dec 1;21(23):7041-4.PMID:22014547DOI:10.1016/j.bmcl.2011.09.097.
From the methanol extract of the bulbs of Pancratium illyricum L., three phenanthridine type alkaloids, Ungeremine (1), (-)-lycorine (2) and (+)-vittatine (3) were isolated. For the evaluation of their anticancer and antibacterial potential, compounds 1-3 were tested against human (I, IIα) and bacterial (IA, IV) topoisomerases. Our data demonstrated that Ungeremine impairs the activity of both, human and bacterial topoisomerases. Remarkably, Ungeremine was found to largely increments the DNA cleavage promoted by bacterial topoisomerase IA, a new target in antimicrobial chemotherapy.
Cytotoxicity of Ungeremine towards multi-factorial drug resistant cancer cells and induction of apoptosis, ferroptosis, necroptosis and autophagy
Phytomedicine 2019 Jul;60:152832.PMID:31031043DOI:10.1016/j.phymed.2019.152832.
Background: Successful cancer chemotherapy is hampered by resistance of cancer cells to established anticancer drugs. Numerous natural products reveal cytotoxicity towards tumor cells. Purpose: The present study was aimed to determine the cytotoxicity of a betaine-type alkaloid, Ungeremine, towards 9 cancer cell lines including various sensitive and drug-resistant phenotypes. The mode of action of this compound was further investigated. Methods: The cytotoxicity, ferroptotic and necroptotic cell death were determined by the resazurin reduction assay. Caspase activation was evaluated using the caspase-Glo assay. Flow cytometry was applied for the analysis of cell cycle analysis (PI staining), apoptosis (annexin V/PI staining), mitochondrial membrane potential (MMP) (JC-1) and reactive oxygen species (ROS) (H2DCFH-DA). Apoptotic, necroptotic and autophagic markers were determined by Western blotting. CCRF-CEM leukemia cells were used for all mechanistic studies. Results: Ungeremine displayed cytotoxic activity towards the 9 cancer cell lines tested, including drug-sensitive and MDR phenotypes. The IC50values obtained varied from 3.67 µM (in MDA-MB-231-BCRP breast carcinoma cells) to 75.24 µM (against in CEM/ADR5000 leukemia cells) for Ungeremine and from 0.02 µM (against CCRF-CEM cells) to 122.96 µM (against CEM/ADR5000 cells) for doxorubicin (control drug). Ungeremine induced ferroptosis, necroptosis, autophagy as well as apoptosis mediated by caspase activation, MMP alteration and increase ROS production. Conclusion: The present investigation showed that Ungeremine is a promising cytotoxic compoundthat could be further explored in the future to develop new anticancer drugs to fight sensitive and resistant phenotypes.
Effect of pH and TPP concentration on chemico-physical properties, release kinetics and antifungal activity of Chitosan-TPP-Ungeremine microbeads
Carbohydr Polym 2018 Sep 1;195:631-641.PMID:29805021DOI:10.1016/j.carbpol.2018.05.005.
In this study, chitosan based microbeads containing Ungeremine, an antimicrobial alkaloid particularly active against Penicillium roqueforti, a filamentous fungus responsible of the bakery products deterioration, were prepared by external gelation by using sodium tripolyphosphate (TPP) as crosslinking agent. The stability of the beads, as well as the loading efficiency of the bioactive molecule, were assessed at different pH and TPP concentrations resulting particularly enhanced at low pH. All the microbeads evidenced antimicrobial activity against Penicillium roqueforti. The release kinetics of Ungeremine was tailored by opportunely modulating pH and TPP concentrations. Morphological analysis evidenced the improvement of the structural crosslinking density of microbeads including Ungeremine and spectroscopic analysis emphasized the active participation of Ungeremine to the crosslinking process occurring between chitosan and TPP. Finally, thermogravimetric analysis confirmed the increasing of free volume in three-dimensional networks and their liability to thermal degradation.
Isolation of the acetylcholinesterase inhibitor Ungeremine from Nerine bowdenii by preparative HPLC coupled on-line to a flow assay system
Biol Pharm Bull 2004 Nov;27(11):1804-9.PMID:15516727DOI:10.1248/bpb.27.1804.
In an attempt to isolate the active compound while detecting acetylcholinesterase inhibitory activity, we applied a fluorometric flow assay system to an on-line coupled preparative HPLC. The MeOH extract of Nerine bowdenii showed a strong inhibitory peak in the on-line assay, and the active compound was isolated by CPC and HPLC. It was identified as Ungeremine by analysis of its (1)H-NMR, 2D-NMR, and NOESY spectra. The assignment of the active N. bowdenii constituent was also confirmed by co-TLC, co-HPLC, and co-(1)H-NMR experiments using an authentic sample of synthetic Ungeremine. The IC(50) value of Ungeremine was 0.35 microM, showing stronger activity than galanthamine (2.2 microM).