ZerumboneCAS# 471-05-6 |
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| Cas No. | 471-05-6 | SDF | Download SDF |
| PubChem ID | 5470187 | Appearance | White-off white powder |
| Formula | C15H22O | M.Wt | 218.3 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in DMSO and ethan | ||
| Chemical Name | (2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one | ||
| SMILES | CC1=CCC(C=CC(=O)C(=CCC1)C)(C)C | ||
| Standard InChIKey | GIHNTRQPEMKFKO-SKTNYSRSSA-N | ||
| Standard InChI | InChI=1S/C15H22O/c1-12-6-5-7-13(2)14(16)9-11-15(3,4)10-8-12/h7-9,11H,5-6,10H2,1-4H3/b11-9+,12-8+,13-7+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Zerumbone is a potential antimicrobial and antibiofilm agent indicated for the therapeutic management of nosocomial medical device-related infections induced by dual-species biofilms of C. albicans and S. aureus. Zerumbone protects the neuronal injury and ameliorates the cognitive function by stimulating the proliferation of endogenous neural stem cells; it suppresses enterotoxigenic bacteroides fragilis infection-induced colonic inflammation through inhibition of NF-κΒ. Zerumbone exhibits a hepatoprotective effect against ALI through its antioxidant and anti-inflammatory activities and the possible mechanism might be mediated by the TLR4/NF-κB/COX-2 pathway. Zerumbone can be a potential candidate for development of immunosuppressive agent. |
| Targets | NF-κB | TLR4 | COX | Notch-1 | Hes-1 | NOS | TNF-α | TLR |
| In vitro | Efficacy of zerumbone against dual-species biofilms of Candida albicans and Staphylococcus aureus.[Pubmed: 31585154 ]Microb Pathog. 2019 Oct 1;137:103768.Candida albicans and Staphylococcus aureus are the most common opportunistic pathogens that co-exist as mixed biofilms. Dual-species biofilms of C. albicans and S. aureus cause nosocomial medical device-related infections that are strongly resistant to antibiotics and host immune responses compared with mono-species biofilms. The purpose of this study was to describe the efficacy of Zerumbone derived from Zingiber zerumbet (L.) Smith, on dual-species biofilm formation. |
| In vivo | Zerumbone promotes proliferation of endogenous neural stem cells in vascular dementia by regulating Notch signalling.[Pubmed: 31588714 ]Folia Neuropathol. 2019;57(3):277-284.Present investigation determines the effect of Zerumbone on the proliferation of stem cells in vascular dementia (VD) rats.
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| Animal Research | Zerumbone Protects against Carbon Tetrachloride (CCl4)-Induced Acute Liver Injury in Mice via Inhibiting Oxidative Stress and the Inflammatory Response: Involving the TLR4/NF-κB/COX-2 Pathway.[Pubmed: 31121820 ]Zerumbone from Zingiber zerumbet inhibits innate and adaptive immune responses in Balb/C mice.[Pubmed: 31177081]Zerumbone Suppresses Enterotoxigenic Bacteroides fragilis Infection-Induced Colonic Inflammation through Inhibition of NF-κΒ.[Pubmed: 31540059 ]Int J Mol Sci. 2019 Sep 14;20(18). pii: E4560.Enterotoxigenic Bacteroides fragilis (ETBF) is human intestinal commensal bacterium and a potent initiator of colitis through secretion of the metalloprotease Bacteroides fragilis toxin (BFT). BFT induces cleavage of E-cadherin in colon cells, which subsequently leads to NF-κB activation. Zerumbone is a key component of the Zingiber zerumbet (L.) Smith plant and can exhibit anti-bacterial and anti-inflammatory effects. However, whether Zerumbone has anti-inflammatory effects in ETBF-induced colitis remains unknown. The aim of this study was to determine the anti-inflammatory effect of orally administered Zerumbone in a murine model of ETBF infection.
Int Immunopharmacol. 2019 Aug;73:552-559.Zerumbone exhibited various biological properties including in vitro immunosuppressive effects. However, its modulatory activity on the immune responses in experimental animal model is largely unknown. Molecules. 2019 May 22;24(10). pii: E1964.The natural compound Zerumbone (hereinafter referred to as ZER), a monocyclic sesquiterpenoid, has been reported to possess many pharmacological properties, including antioxidant and anti-inflammatory properties. This study aimed to investigate the underlying mechanism of ZER against acute liver injury (ALI) in CCl4-induced mice models.
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Zerumbone Dilution Calculator
Zerumbone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.5809 mL | 22.9043 mL | 45.8085 mL | 91.617 mL | 114.5213 mL |
| 5 mM | 0.9162 mL | 4.5809 mL | 9.1617 mL | 18.3234 mL | 22.9043 mL |
| 10 mM | 0.4581 mL | 2.2904 mL | 4.5809 mL | 9.1617 mL | 11.4521 mL |
| 50 mM | 0.0916 mL | 0.4581 mL | 0.9162 mL | 1.8323 mL | 2.2904 mL |
| 100 mM | 0.0458 mL | 0.229 mL | 0.4581 mL | 0.9162 mL | 1.1452 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Hepatoprotective Effects of Zerumbone against Paracetamol-Induced Acute Hepatotoxicity in Rats.[Pubmed:30918456]
Malays J Med Sci. 2018 Mar;25(2):64-71.
Background: Zerumbone (ZER) is a major bioactive compound of Zingiber zerumbet, a wild ginger plant that has been documented to have anti-proliferative, anti-inflammatory and anti-oxidant properties. To investigate its hepatoprotective potential, this study was designed to determine the treatment effects of ZER on acute hepatotoxicity induced by paracetamol (PCM) in rats. Methods: The control group was administered with phosphate buffer solution (PBS) while the other two groups received PCM alone (1000 mg/kg) and PCM + 25 mg/kg ZER, respectively, at 0 h and 4 h after PCM injection. After 24 h, the blood and liver were collected for differential white blood cell count, liver histological observation and biochemical analysis including alanine aminotransferase (ALT), aspartate aminotransferase (AST), and total protein concentration in serum and liver. Results: Treatment with ZER was found to significantly reduce ALT (P = 0.041), AST (P = 0.044) and total hepatic protein (P = 0.045) in comparison to PCM-induced rats. Rats treated with ZER exhibited the normal structure of hepatocytes with no vacuolisation or necrosis and showed significantly reduced neutrophil count (P = 0.037). This finding suggests its ability to suppress the inflammatory processes caused by PCM overdosage and decrease the hepatocytes tendency to go through necrotic processes. Conclusion: ZER possessed protective activity against PCM-induced acute hepatotoxicity in a rat model.
Dietary zerumbone, a sesquiterpene, ameliorates hepatotoxin-mediated acute and chronic liver injury in mice.[Pubmed:30868670]
Phytother Res. 2019 Mar 14.
Acute liver injury (ALI) is a life-threatening clinical syndrome. Long-lasting liver injury can lead to chronic hepatic inflammation and fibrogenic responses. Zerumbone (ZER), the main constituent of rhizomes of Zingiber zerumbet Smith, has a variety of functions including anticancer activity. We investigated the role of ZER on the progression of hepatotoxin-induced liver injury. Single or repeated injection of CCl4 was used to induce acute or chronic liver injury, respectively. Mice were orally administered with ZER (10, 50 mg/kg) during the experimental period. Histopathologic analysis and serum biochemical levels revealed that ZER had hepatoprotective activities against ALI. Similar effects of ZER on injured livers were confirmed by analyses of inflammation and apoptosis-related genes. Western blot analysis showed that protein levels of apoptotic molecules were decreased, whereas antiapoptotic protein levels were conversely increased in injured livers treated with ZER. Furthermore, chronic liver injury and its associated fibrogenesis in mice were reduced by ZER treatment. These findings from our in vivo experiments further indicate that ZER could alleviate hepatocellular toxicity and inhibit activation of primary hepatic stellate cells. Our results suggest that ZER might have potential as a safe and prophylactic alternative to prevent acute and chronic liver injury.
Potential of Zerumbone as an Anti-Cancer Agent.[Pubmed:30781671]
Molecules. 2019 Feb 18;24(4). pii: molecules24040734.
Cancer is still a major risk factor to public health globally, causing approximately 9.8 million deaths worldwide in 2018. Despite advances in conventional treatment modalities for cancer treatment, there are still few effective therapies available due to the lack of selectivity, adverse side effects, non-specific toxicities, and tumour recurrence. Therefore, there is an immediate need for essential alternative therapeutics, which can prove to be beneficial and safe against cancer. Various phytochemicals from natural sources have been found to exhibit beneficial medicinal properties against various human diseases. Zerumbone is one such compound isolated from Zingiber zerumbet Smith that possesses diverse pharmacological properties including those of antioxidant, antibacterial, antipyretic, anti-inflammatory, immunomodulatory, as well as anti-neoplastic. Zerumbone has shown its anti-cancer effects by causing significant suppression of proliferation, survival, angiogenesis, invasion, and metastasis through the molecular modulation of different pathways such as NF-kappaB, Akt, and IL-6/JAK2/STAT3 (interleukin-6/janus kinase-2/signal transducer and activator of transcription 3) and their downstream target proteins. The current review briefly summarizes the modes of action and therapeutic potential of Zerumbone against various cancers.
Immunomodulation of Zerumbone via Decreasing the Production of Reactive Oxygen Species from Immune Cells.[Pubmed:30724050]
Pak J Biol Sci. 2018 Jan;21(9):475-479.
BACKGROUND AND OBJECTIVE: Zerumbone has been reported to exert anti-inflammatory, anti-ulcer and anti-hyperglycemic effects but the specific mechanism through which Zerumbone exerts its anti-inflammatory action through inhibiting reactive oxygen species was not well studied. Hence, this paper studied the Zerumbone capacity to inhibit intracellular and extracellular Reactive Oxygen Species (ROS) produced by whole blood cell, polymorphoneutrophil (PMNs) and macrophage cells due to the zymogen and phorbolmyristerate acetate (PMA) oxidant effect. MATERIALS AND METHODS: Zymogen and PMA based chemiluminescence assay were used to determine the immunomodulatory effect of Zerumbone at concentrations (100, 10 and 1 mug mL-1) toward production of Reactive Oxygen Species (ROS) from whole blood, PMNs and macrophage. RESULTS: Zerumbone significantly inhibited intracellular and extracellular ROS production by the zymosan/PMA-activated phagocyte cells with IC50 values of (16.3+/-0.1, 23.7+/-0.1 and 4.97+/-0.1 mug mL-1) against whole blood, PMNs and macrophage respectively. CONCLUSION: The anti-inflammatory activity of Zerumbone was so much significant that even strong oxidant (zymogen and PMA) were not able to produce reactive oxygen species when incubated together in phagocytic cells, thus suppress production of ROS. Therefore, it is highly used in herbal medicine as a potent immunomodulatory therapy in various inflammation associated diseases.
Zerumbone Suppresses Human Colorectal Cancer Invasion and Metastasis via Modulation of FAk/PI3k/NFkappaB-uPA Pathway.[Pubmed:30650987]
Nutr Cancer. 2019;71(1):159-171.
The current study explored the basic molecular mechanisms of Zerumbone (ZER), an herbal compound, in inhibiting the migration and invasion of colorectal cancer (CRC) cells in vitro. Two types of CRC cells, namely HCT-116 and SW48, were treated with various concentrations of ZER (8, 16, and 24 microM) for 24, 48, and 72 h, respectively. In vitro assays were performed to determine alterations in proliferation ability, mRNA expression and protein levels, and migration and invasion potential of CRC cells. An SYBR Green-based quantitative polymerase chain reaction (PCR) was utilized to detect the gene expression of focal adhesion kinase (FAK), nuclear factor (NF)-kappaB, and urokinase-type plasminogen activator (uPA) followed by the evaluation of the level of proteins by western blotting. Migration and invasion potentials of HCT-116 and SW48 cells treated by ZER were examined using migration and invasion assay kits, respectively. We compared the results of all experiments with control groups, including FAK inhibitor, ZER + FAK inhibitor-treated cells, NF-beta inhibitor, ZER + NF-beta inhibitor, and untreated cells. The data in the present study suggest that ZER may exert its antimetastatic effects through inhibition of FAk/PI3k/NF-kappaB-uPA signaling pathway, thereby possibly representing a novel class of FAK inhibitors.
Immunosuppressive effects of the standardized extract of Zingiber zerumbet on innate immune responses in Wistar rats.[Pubmed:30618097]
Phytother Res. 2019 Jan 8.
Zingiber zerumbet rhizome has been used in traditional medicine mainly for the treatment of various immune-inflammatory related ailments and has been shown to exhibit a wide spectrum of biological effects especially antioxidant and anti-inflammatory activities. The present study was aimed to investigate the immunosuppressive effects of the standardized 80% ethanol extract of Z. zerumbet at 100, 200, and 400 mg/kg on the innate immune responses in male Wistar rats. The immune parameters determined were chemotaxis of neutrophils, Mac-1 expression, engulfment of Escherichia coli by neutrophils, reactive oxygen species production, and plasma lysozyme and ceruloplasmin levels. Zerumbone was qualitatively and quantitatively determined in the extract by using a validated reversed-phase HPLC, whereas liquid chromatography tandem-mass spectrometry (LC -MS/MS) was used to profile the secondary metabolites. Z. zerumbet significantly inhibited the migration of neutrophils, expressions of CD11b/CD18 integrin, phagocytic activity, and production of reactive oxygen species in a dose-dependent manner. The extract also dose-dependently inhibited the expressions of lysozyme and ceruloplasmin in the rat plasma. Z. zerumbet extract possessed strong inhibitory effects on the innate immune responses and has potential to be developed into an effective immunosuppressive agent.
Zerumbone inhibits migration in ESCC via promoting Rac1 ubiquitination.[Pubmed:30551505]
Biomed Pharmacother. 2019 Jan;109:2447-2455.
Zerumbone has been reported to maintain the anti-cancer effects in many malignant cells. However, the effect and mechanism of Zerumbone on esophageal squamous cell carcinomas (ESCC) is rarely investigated. Here we report the inhibitory effect of Zerumbone (hereinafter referred to as ZER) on ESCC migration and the underlying molecular mechanism. ZER could inhibit the migration of human esophageal squamous cancer KYSE-30 cells and KYSE-150 cells. ZER induced Rac1 protein down-regulation in a dose- and time-dependent manner. The reduction of Rac1 protein was crucial for ZER-induced inhibition of cell migration, as Rac1 knockdown could enhance ZER-induced inhibition of cell migration. We further demonstrated that the decrease of Rac1 after ZER treatment is via proteasome-dependent degradation pathway, and ZER treatment drastically enhanced ubiquitination of Rac1, which finally caused Rac1 degradation. Collectively, our results indicated that ZER inhibits cell migration by suppressing Rac1 expression. This suppresion is achieved through promoting Rac1 ubiquitination and degradation. Thus, the study raises the possibility of ZER as a potential drug for ESCC due to its ability to inhibit cell migration.
Zerumbone, a cyclic sesquiterpene, exerts antimitotic activity in HeLa cells through tubulin binding and exhibits synergistic activity with vinblastine and paclitaxel.[Pubmed:30525278]
Cell Prolif. 2019 Mar;52(2):e12558.
OBJECTIVES: The aim of this study was to elucidate the antimitotic mechanism of Zerumbone and to investigate its effect on the HeLa cells in combination with other mitotic blockers. MATERIALS AND METHODS: HeLa cells and fluorescence microscopy were used to analyse the effect of Zerumbone on cancer cell lines. Cellular internalization of Zerumbone was investigated using FITC-labelled Zerumbone. The interaction of Zerumbone with tubulin was characterized using fluorescence spectroscopy. The Chou and Talalay equation was used to calculate the combination index. RESULTS: Zerumbone selectively inhibited the proliferation of HeLa cells with an IC50 of 14.2 +/- 0.5 mumol/L through enhanced cellular uptake compared to the normal cell line L929. It induced a strong mitotic block with cells exhibiting bipolar spindles at the IC50 and monopolar spindles at 30 mumol/L. Docking analysis indicated that tubulin is the principal target of Zerumbone. In vitro studies indicated that it bound to goat brain tubulin with a Kd of 4 mumol/L and disrupted the assembly of tubulin into microtubules. Zerumbone and colchicine had partially overlapping binding site on tubulin. Zerumbone synergistically enhanced the anti-proliferative activity of vinblastine and paclitaxel through augmented mitotic block. CONCLUSION: Our data suggest that disruption of microtubule assembly dynamics is one of the mechanisms of the anti-cancer activity of Zerumbone and it can be used in combination therapy targeting cell division.
Zerumbone from Zingiber zerumbet (L.) smith: a potential prophylactic and therapeutic agent against the cariogenic bacterium Streptococcus mutans.[Pubmed:30424764]
BMC Complement Altern Med. 2018 Nov 13;18(1):301.
BACKGROUND: Essential oil obtained from rhizomes of the Zingiber zerumbet (L.) Smith (popularly known in Brazil as bitter ginger) is mainly constituted by the biomolecule Zerumbone, which exhibit untapped antimicrobial potential. The aim of this study was to investigate the antimicrobial activity of the Zerumbone from bitter ginger rhizomes against the cariogenic agent Streptococcus mutans. METHODS: Firstly, the essential oil from rhizomes of Zingiber zerumbet (L.) Smith extracted by hydrodistillation was submitted to purification and recrystallization process to obtain the Zerumbone compound. The purity of Zerumbone was determined through high-performance liquid chromatography analysis. Different concentrations of Zerumbone were tested against the standard strain S. mutans (ATCC 35668) by using microdilution method. The speed of cidal activity was determined through a time kill-curve assay. The biological cytotoxicity activity of Zerumbone was assessed using Vero cell line through MTT assay. RESULTS: The Zerumbone showed a minimum inhibitory concentration (MIC) of 250 mug/mL and a minimum bactericidal concentration (MBC) of 500 mug/mL against S. mutans. After six hours of bacteria-Zerumbone interaction, all concentrations tested starts to kill the bacteria and all bacteria were killed between 48 and 72 h period at the concentration of 500 mug/mL (99,99% of bacteria were killed in comparison with original inoculum). In addition, Zerumbone showed no cytotoxicity activity on mammalian continuous cells line. CONCLUSIONS: These results draw attention to the potential of Zerumbone as antimicrobial agent against S. mutans infection, indicating its possible use in the phyto-pharmaceutical formulations as new approach to prevent and treat tooth decay disease.
Zerumbone-Loaded Nanostructured Lipid Carrier Induces Apoptosis of Canine Mammary Adenocarcinoma Cells.[Pubmed:30410940]
Biomed Res Int. 2018 Oct 15;2018:8691569.
Canine mammary gland tumor (CMT) is the most common tumor in intact female dog. Zerumbone (ZER) has promising anticancer properties, but plagued with poor water solubility, poor absorption, bioavailability, and delivery to target tissues. To solubilize, ZER was loaded into nanostructured lipid carrier (NLC) to produce ZER-loaded NLC (ZER-NLC). The objectives of this study were to determine the antiproliferative effect and the mode of cell death induced by ZER-NLC and ZER on a canine mammary gland tumor (CMT) adenocarcinoma primary cell line. There was no significant difference (p>0.05) between ZER-NLC and ZER treatments in the inhibition of CMT cell proliferation; thus, the loading of ZER into NLC did not compromise the cytotoxic effect of ZER. Microscopically, ZER-NLC- and ZER-treated CMT cells showed apoptotic cell morphology. ZER-NLC and ZER treatments significantly downregulated the antiapoptotic Bcl-2 and upregulated the proapoptotic Bax gene expressions in CMT cells. Both ZER-NLC and ZER-treated CMT cells showed significant (p<0.0001) increases in caspase-8, -9, and -3/7 protein activities. In conclusion, ZER-NLC induced CMT cell death via regulation of Bcl-2 and Bax gene expressions and caspase activations, indicating the involvement of both the intrinsic and extrinsic pathways of apoptosis. This study provided evidences for the potential of ZER-NLC as an anticanine mammary gland adenocarcinoma chemotherapy.
