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Cerberin Sale

(Synonyms: 海果苷) 目录号 : GC49706

A cardiac glycoside with cytotoxic and cardiac modulatory activities

Cerberin Chemical Structure

Cas No.:25633-33-4

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2.5 mg
¥4,585.00
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产品描述

Cerberin is a cardiac glycoside that has been found in C. odollam and has cytotoxic and cardiac modulatory activities.1,2 It is cytotoxic to KB and NCI H187 cancer cells (IC50s = 1.92 and 1.24 µg/ml).1 Cerberin inhibits Na+/K+-ATPase, increasing intracellular sodium levels and action potential duration in cardiac cells.2

1.Laphookhieo, S., Cheenpracha, S., Karalai, C., et al.Cytotoxic cardenolide glycoside from the seeds of Cerbera odollamPhytochemistry65(4)507-510(2004) 2.Menezes, R.G., Usman, M.S., Hussain, S.A., et al.Cerbera odollam toxicity: A reviewJ. Forensic Leg. Med.58113-116(2018)

Chemical Properties

Cas No. 25633-33-4 SDF Download SDF
别名 海果苷
Canonical SMILES O[C@@]12[C@@]3([H])[C@@](CC[C@@]1([C@](C(CO4)=CC4=O)([H])CC2)C)([H])[C@@]5([C@](C[C@H](CC5)O[C@H]6[C@H]([C@@H]([C@H]([C@@H](O6)C)O)OC)OC(C)=O)([H])CC3)C
分子式 C32H48O9 分子量 576.7
溶解度 Chloroform: slightly soluble,Methanol: slightly soluble 储存条件 -20°C
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1 mg 5 mg 10 mg
1 mM 1.734 mL 8.67 mL 17.34 mL
5 mM 0.3468 mL 1.734 mL 3.468 mL
10 mM 0.1734 mL 0.867 mL 1.734 mL
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Research Update

Cardiac glycoside Cerberin exerts anticancer activity through PI3K/AKT/mTOR signal transduction inhibition

Cancer Lett 2019 Jul 1;453:57-73.PMID:30930233DOI:10.1016/j.canlet.2019.03.034.

Natural products possess a significant role in anticancer therapy and many currently-used anticancer drugs are of natural origin. Cerberin (CR), a cardenolide isolated from the fruit kernel of Cerbera odollam, was found to potently inhibit cancer cell growth (GI50 values < 90 nM), colony formation and migration. Significant G2/M cell cycle arrest preceded time- and dose-dependent apoptosis-induction in human cancer cell lines corroborated by dose-and time-dependent PARP cleavage and caspase 3/7 activation, in addition to reduced Bcl-2 and Mcl-1 expression. CR potently inhibited PI3K/AKT/mTOR signalling depleting polo-like kinase 1 (PLK-1), c-Myc and STAT-3 expression. Additionally, CR significantly increased the generation of reactive oxygen species (ROS) producing DNA double strand breaks. Preliminary in silico biopharmaceutical assessment of CR predicted >60% bioavailability and rapid absorption; doses of 1-10 mg/kg CR were predicted to maintain efficacious unbound plasma concentrations (>GI50 value). CR's potent and selective anti-tumour activity, and its targeting of key signalling mechanisms pertinent to tumourigenesis support further preclinical evaluation of this cardiac glycoside.

Cerbera odollam toxicity: A review

J Forensic Leg Med 2018 Aug;58:113-116.PMID:29778924DOI:10.1016/j.jflm.2018.05.007.

Cerbera odollam is a plant species of the Apocynaceae family. It is often dubbed the 'suicide tree' due to its strong cardiotoxic effects, which make it a suitable means to attempt suicide. The plant grows in wet areas in South India, Madagascar, and Southeast Asia; and its common names include Pong-Pong and Othalanga. The poison rich part of the plant is the kernel which is present at the core of its fruit. The bioactive toxin in the plant is Cerberin, which is a cardiac glycoside of the cardenolide class. Cerberin has a mechanism of action similar to digoxin; hence, Cerbera odollam toxicity manifests similar to acute digoxin poisoning. Ingestion of its kernel causes nausea, vomiting, hyperkalemia, thrombocytopenia, and ECG abnormalities. Exposure to high doses of Cerbera odollam carries the highest risk of mortality. Initial management includes supportive therapy and administration of atropine followed by temporary pacemaker insertion. Administration of digoxin immune Fab may be considered in severe cases, although efficacy is variable and data limited to isolated case reports.

Bintaro (Cerbera odollam and Cerbera manghas): an overview of its eco-friendly use, pharmacology, and toxicology

Environ Sci Pollut Res Int 2022 Aug 31;1-14.PMID:36044149DOI:10.1007/s11356-022-22585-w.

Bintaro is a tropical mangrove plant often used as a shade tree found in Asia, Australia, Madagascar, and the Islands of the Western Pacific Ocean. The word Bintaro is also often pinned to its closest relative species, the Cerbera odollam. Flower color is one of the distinguishing features between these two species. Human poisoning with the cardiotoxic plant Bintaro is common in Southeast Asia because it bears a fruit that yields a powerful poison that has been used for suicide and homicide, hence it is also called the "Indian suicide tree". The seeds of Bintaro contain Cerberin, a cardiac glycoside toxin of the heart that blocks the calcium ion channels in heart muscles, resulting in disruption of the heartbeat most often fatally. The bio-active compound in the kernels of Bintaro varies due to which plant possesses other properties as well. The plant may also be used for medicinal purposes as it shows many pharmaceutical properties. The seeds of the plant have auspicious anticancer properties through apoptotic activity and the leaf extract of the plant was screened for its antioxidant activities. In addition, it is also used as an insecticide, pesticide, or antifungal agent. This review highlights the Pharmaceutical, toxicological, and environmentally friendly approaches of Bintaro.

The principal toxic glycosidic steroids in Cerbera manghas L. seeds: identification of Cerberin, neriifolin, tanghinin and deacetyltanghinin by UHPLC-HRMS/MS, quantification by UHPLC-PDA-MS

J Chromatogr B Analyt Technol Biomed Life Sci 2014 Jul 1;962:1-8.PMID:24878878DOI:10.1016/j.jchromb.2014.05.014.

The toxicity of the sea mango (Cerbera manghas L.) is well known. The plant is ranked as one of the deadliest of the southern Asian coastline. Cardenolidic heterosides are responsible for the cardiotoxicity of trees of the Cerbera genus. We have identified and determined the concentration of the principal glycosidic steroids present in the seeds of sea mangos (Thailand). Drug screening of an extract of the seeds was carried out using ultra-high performance liquid chromatography coupled to photodiode array detection and mass spectrometry (UHPLC-PDA-MS) with quantification at 219nm. Identification was confirmed by UHPLC-HRMS. Deacetyltanghinin (m/z 549.3055±2ppm), neriifolin (m/z 535.3259±2ppm), tanghinin (m/z 591.3169±2ppm) and Cerberin (577.3375±2ppm) were the most abundant glycosidic steroids present in the sea mango seeds. A seed of the dried ripe fruit had concentrations of 1209.1, 804.2, 621.4 and 285.9μg/g, respectively. A seed of the fresh unripe fruit had concentrations of 49.4, 47.0, 3.5 and 2.3μg/g.

Molluscicidal activity of cardiac glycosides isolated from Adenium obesum

Pest Manag Sci 2019 Oct;75(10):2770-2775.PMID:30838743DOI:10.1002/ps.5388.

Background: Terrestrial mollusks are one of most important agricultural pests worldwide. Natural phytochemicals have an extended history as a source of pesticides. This study was planned to isolate molluscicidal active compounds from the stems of Adenium obesum. Results: The benzene-soluble fraction of the hydroethanolic extract displayed the most potent molluscicidal activity against Monacha obstructa among different solvent fractions with a median lethal dose (LD50 ) of 4.91 µg g-1 body weight (bw). The bioactivity-guided chemical exploration of the benzene-soluble fraction led to the isolation of two known cardiac glycosides, Cerberin and neriifolin which showed significant molluscicidal activity with LD50 values of 5.39 and 4.3 µg g-1 bw, respectively. Conclusion: Isolation of the cardiac glycoside neriifolin from A. obesum and the molluscicidal activity of Cerberin and neriifolin against terrestrial snails are reported for the first time. © 2019 Society of Chemical Industry.