Xanthatin CAS NO.26791-73-1

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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.
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.
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.

Chemical Properties of Xanthatin

Cas No.	26791-73-1
PubChem ID	5281511	Appearance	Powder
Formula	C15H18O3	M.Wt	246.3
Type of Compound	Sesquiterpenoids	Storage	Desiccate at -20°C
Solubility	Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name	(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
SMILES	CC1CC2C(CC=C1C=CC(=O)C)C(=C)C(=O)O2
Standard InChIKey	RBRPTFMVULVGIC-ZTIIIDENSA-N
Standard InChI	InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14-/m0/s1
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.
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.
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.

Source of Xanthatin

The fruits of Xanthium sibiricum

Biological Activity of Xanthatin

Description	Xanthatin is a novel potent inhibitor of VEGFR2 signaling, has significant antitumor activity against a variety of cancer cells through cell cycle arrest and apoptosis induction, it can inhibit angiogenesis and tumor growth in breast cancer cells. Xanthatin has bactericidal and fungicidal activity, including against Colletotrichum gloesporoides, Trichothecium roseum, Bacillus cereus and Staphylococcus aureus.
Targets	Wnt/β-catenin | GSK-3 | STAT | Bcl-2/Bax | p65 | NF-kB | Chk | Antifection | VEGFR
In vitro	Antimicrobial activity of xanthatin from Xanthium spinosum L.[Reference: WebLink] Lett. Appl. Microbiol., 1994, 18(4): 206-8. METHODS AND RESULTS: Dichloromethane extracts from Xanthium spinosum L. were fractionated and the fractions tested for their bactericidal and fungicidal activity. From the active fraction, a compound was isolated and identified as Xanthatin (I). CONCLUSIONS: Xanthatin was active against Colletotrichum gloesporoides, Trichothecium roseum, Bacillus cereus and Staphylococcus aureus. Xanthatin, a novel potent inhibitor of VEGFR2 signaling, inhibits angiogenesis and tumor growth in breast cancer cells.[Pubmed: 26617743 ] Int J Clin Exp Pathol. 2015 Sep 1;8(9):10355-64. Anti-angiogenesis targeting vascular endothelial growth factor receptor 2 (VEGFR2) has emerged as an important tool for cancer treatment. METHODS AND RESULTS: In this study, we described a novel VEGFR2 inhibitor, Xanthatin, which inhibits tumor angiogenesis and growth. The biochemical profiles of Xanthatin were investigated using kinase assay, migration assay, tube formation, Matrigel plug assay, western blot, immunofluorescence and human tumor xenograft model. Xanthatin significantly inhibited growth, migration and tube formation of human umbilical vascular endothelial cell as well as inhibited vascular endothelial growth factor (VEGF)-stimulated angiogenesis. In addition, it inhibited VEGF-induced phosphorylation of VEGFR2 and its downstream signaling regulator. Moreover, Xanthatin directly inhibit proliferation of breast cancer cells MDA-MB-231. Oral administration of Xanthatin could markedly inhibit human tumor xenograft growth and decreased microvessel densities (MVD) in tumor sections. CONCLUSIONS: Taken together, these preclinical evaluations suggest that Xanthatin inhibits angiogenesis and may be a promising anticancer drug candidate.
In vivo	Characterization of xanthatin: anticancer properties and mechanisms of inhibited murine melanoma in vitro and in vivo.[Pubmed: 23664560] Phytomedicine. 2013 Jul 15;20(10):865-73. Anti-cancer investigations on Xanthatin mainly focus on in vitro experiments. We herein reported the anti-tumor effects of Xanthatin both in vitro and in vivo. METHODS AND RESULTS: MTS assay results showed that Xanthatin had a remarkable anti-proliferative effect on B16-F10 cells. Moreover, the expression of β-catenin was up-regulated both in vitro and in vivo. Animal studies further revealed that Xanthatin killed the tumor cells around the blood vessels which contributes to reduce microvascular density extremely. CONCLUSIONS: All these results indicate that Xanthatin inhibited murine melanoma B16-F10 cell proliferation possibly associated with activation of Wnt/β-catenin pathway and its activity against melanoma tumor might also be relevant to inhibition of angiogenesis.

Protocol of Xanthatin

Kinase Assay	Concerted suppression of STAT3 and GSK3β is involved in growth inhibition of non-small cell lung cancer by Xanthatin.[Pubmed: 24312384] PLoS One. 2013 Nov 28;8(11):e81945. Xanthatin, a sesquiterpene lactone purified from Xanthium strumarium L., possesses prominent anticancer activity. METHODS AND RESULTS: We found that disruption of GSK3β activity was essential for Xanthatin to exert its anticancer properties in non-small cell lung cancer (NSCLC), concurrent with preferable suppression of constitutive activation of STAT3. Interestingly, inactivation of the two signals are two mutually exclusive events in Xanthatin-induced cell death. Moreover, we surprisingly found that exposure of Xanthatin failed to trigger the presumable side effect of canonical Wnt/β-Catenin followed by GSK3β inactivation. We further observed that the downregulation of STAT3 was required for Xanthatin to fine-tune the risk. CONCLUSIONS: Thus, the discovery of Xanthatin, which has ability to simultaneously orchestrate two independent signaling cascades, may have important implications for screening promising drugs in cancer therapies.
Cell Research	Xanthatin induces G2/M cell cycle arrest and apoptosis in human gastric carcinoma MKN-45 cells.[Pubmed: 22532019] Planta Med. 2012 Jun;78(9):890-5. Xanthatin, a natural bioactive compound of sesquiterpene lactones, was isolated and purified from air-dried aerial part of Xanthium sibiricum Patrin ex Widder. In the present study, we demonstrated the significant antiproliferative and proapoptotic effects of Xanthatin on human gastric carcinoma MKN-45 cells. METHODS AND RESULTS: MTS assay showed that Xanthatin produced obvious cytotoxicity in MKN-45 cells with IC50 values of 18.6, 9.3, and 3.9 μM for 12, 24, and 48 h, respectively. Results of flow cytometry analysis indicated that the antiproliferative activity induced by Xanthatin might be executed via G2/M cell cycle arrest and proapoptosis in MKN-45 cells. Western blot analysis elucidated that: a) Xanthatin downregulated expression of Chk1 and Chk2 and phosphorylation of CDC2, which are known as key G2/M transition regulators; b) Xanthatin increased p53 activation, decreased the bcl-2/bax ratio and the levels of downstream procaspase-9 and procaspase-3, which are key regulators in the intrinsic apoptosis pathway; c) Xanthatin blocked phosphorylation of NF-κB (p65 subunit) and of IκBα, which might contribute to its proapoptotic effects on MKN-45 cells. CONCLUSIONS: In conclusion, our results suggest that Xanthatin may have therapeutic potential against human gastric carcinoma.
Structure Identification	Eur J Med Chem. 2015 Jan 27;90:491-6. Optimization of xanthatin extraction from Xanthium spinosum L. and its cytotoxic, anti-angiogenesis and antiviral properties.[Pubmed: 25481815] METHODS AND RESULTS: The aqueous extraction of the sesquiterpene lactone Xanthatin from Xanthium spinosum L. favours the conversion of xanthinin (1) to Xanthatin (2) via the loss of acetic acid. The cytotoxic (Hep-G2 and L1210 human cell lines) and antiviral activities of isolated Xanthatin are established. This natural compound shows significant cytotoxicity against the Hep-G2 cell line and our experimental results reveal its strong anti-angiogenesis capacity in vitro. CONCLUSIONS: The structure of Xanthatin is determined by spectroscopic methods and for the first time confirmed by X-ray diffraction.

Preparing Stock Solutions of Xanthatin

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	4.0601 mL	20.3004 mL	40.6009 mL	81.2018 mL	101.5022 mL
5 mM	0.812 mL	4.0601 mL	8.1202 mL	16.2404 mL	20.3004 mL
10 mM	0.406 mL	2.03 mL	4.0601 mL	8.1202 mL	10.1502 mL
50 mM	0.0812 mL	0.406 mL	0.812 mL	1.624 mL	2.03 mL
100 mM	0.0406 mL	0.203 mL	0.406 mL	0.812 mL	1.015 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.

 

References on Xanthatin

Xanthatin induces cell cycle arrest at G2/M checkpoint and apoptosis via disrupting NF-kappaB pathway in A549 non-small-cell lung cancer cells.[Pubmed:22450683]

Molecules. 2012 Mar 26;17(4):3736-50.

Xanthatin, a natural sesquiterpene lactone, has significant antitumor activity against a variety of cancer cells, yet little is known about its anticancer mechanism. In this study, we demonstrated that Xanthatin had obvious dose-/time-dependent cytotoxicity against the human non-small-cell lung cancer (NSCLC) cell line A549. Flow cytometry analysis showed Xanthatin induced cell cycle arrest at G2/M phase. Xanthatin also had pro-apoptotic effects on A549 cells as evidenced by Hoechst 33258 staining and annexin V-FITC staining. Mechanistic data revealed that Xanthatin downregulated Chk1, Chk2, and phosphorylation of CDC2, which contributed to the cell cycle arrest. Xathatin also increased total p53 protein levels, decreased Bcl-2/Bax ratio and expression of the downstream factors procaspase-9 and procaspase-3, which triggered the intrinsic apoptosis pathway. Furthermore, Xanthatin blocked phosphorylation of NF-kappaB (p65) and IkappaBa, which might also contribute to its pro-apoptotic effects on A549 cells. Xanthatin also inhibited TNFa induced NF-kappaB (p65) translocation. We conclude that Xanthatin displays significant antitumor effects through cell cycle arrest and apoptosis induction in A549 cells. These effects were associated with intrinsic apoptosis pathway and disrupted NF-kappaB signaling. These results suggested that Xanthatin may have therapeutic potential against NSCLC.

Concerted suppression of STAT3 and GSK3beta is involved in growth inhibition of non-small cell lung cancer by Xanthatin.[Pubmed:24312384]

PLoS One. 2013 Nov 28;8(11):e81945.

Xanthatin, a sesquiterpene lactone purified from Xanthium strumarium L., possesses prominent anticancer activity. We found that disruption of GSK3beta activity was essential for Xanthatin to exert its anticancer properties in non-small cell lung cancer (NSCLC), concurrent with preferable suppression of constitutive activation of STAT3. Interestingly, inactivation of the two signals are two mutually exclusive events in Xanthatin-induced cell death. Moreover, we surprisingly found that exposure of Xanthatin failed to trigger the presumable side effect of canonical Wnt/beta-Catenin followed by GSK3beta inactivation. We further observed that the downregulation of STAT3 was required for Xanthatin to fine-tune the risk. Thus, the discovery of Xanthatin, which has ability to simultaneously orchestrate two independent signaling cascades, may have important implications for screening promising drugs in cancer therapies.

Characterization of xanthatin: anticancer properties and mechanisms of inhibited murine melanoma in vitro and in vivo.[Pubmed:23664560]

Phytomedicine. 2013 Jul 15;20(10):865-73.

Anti-cancer investigations on Xanthatin mainly focus on in vitro experiments. We herein reported the anti-tumor effects of Xanthatin both in vitro and in vivo. MTS assay results showed that Xanthatin had a remarkable anti-proliferative effect on B16-F10 cells. Moreover, the expression of beta-catenin was up-regulated both in vitro and in vivo. Animal studies further revealed that Xanthatin killed the tumor cells around the blood vessels which contributes to reduce microvascular density extremely. All these results indicate that Xanthatin inhibited murine melanoma B16-F10 cell proliferation possibly associated with activation of Wnt/beta-catenin pathway and its activity against melanoma tumor might also be relevant to inhibition of angiogenesis.

Xanthatin, a novel potent inhibitor of VEGFR2 signaling, inhibits angiogenesis and tumor growth in breast cancer cells.[Pubmed:26617743]

Int J Clin Exp Pathol. 2015 Sep 1;8(9):10355-64. eCollection 2015.

Anti-angiogenesis targeting vascular endothelial growth factor receptor 2 (VEGFR2) has emerged as an important tool for cancer treatment. In this study, we described a novel VEGFR2 inhibitor, Xanthatin, which inhibits tumor angiogenesis and growth. The biochemical profiles of Xanthatin were investigated using kinase assay, migration assay, tube formation, Matrigel plug assay, western blot, immunofluorescence and human tumor xenograft model. Xanthatin significantly inhibited growth, migration and tube formation of human umbilical vascular endothelial cell as well as inhibited vascular endothelial growth factor (VEGF)-stimulated angiogenesis. In addition, it inhibited VEGF-induced phosphorylation of VEGFR2 and its downstream signaling regulator. Moreover, Xanthatin directly inhibit proliferation of breast cancer cells MDA-MB-231. Oral administration of Xanthatin could markedly inhibit human tumor xenograft growth and decreased microvessel densities (MVD) in tumor sections. Taken together, these preclinical evaluations suggest that Xanthatin inhibits angiogenesis and may be a promising anticancer drug candidate.

Optimization of xanthatin extraction from Xanthium spinosum L. and its cytotoxic, anti-angiogenesis and antiviral properties.[Pubmed:25481815]

Eur J Med Chem. 2015 Jan 27;90:491-6.

The aqueous extraction of the sesquiterpene lactone Xanthatin from Xanthium spinosum L. favours the conversion of xanthinin (1) to Xanthatin (2) via the loss of acetic acid. The cytotoxic (Hep-G2 and L1210 human cell lines) and antiviral activities of isolated Xanthatin are established. This natural compound shows significant cytotoxicity against the Hep-G2 cell line and our experimental results reveal its strong anti-angiogenesis capacity in vitro. The structure of Xanthatin is determined by spectroscopic methods and for the first time confirmed by X-ray diffraction.

Xanthatin induces G2/M cell cycle arrest and apoptosis in human gastric carcinoma MKN-45 cells.[Pubmed:22532019]

Planta Med. 2012 Jun;78(9):890-5.

Xanthatin, a natural bioactive compound of sesquiterpene lactones, was isolated and purified from air-dried aerial part of Xanthium sibiricum Patrin ex Widder. In the present study, we demonstrated the significant antiproliferative and proapoptotic effects of Xanthatin on human gastric carcinoma MKN-45 cells. MTS assay showed that Xanthatin produced obvious cytotoxicity in MKN-45 cells with IC50 values of 18.6, 9.3, and 3.9 microM for 12, 24, and 48 h, respectively. Results of flow cytometry analysis indicated that the antiproliferative activity induced by Xanthatin might be executed via G2/M cell cycle arrest and proapoptosis in MKN-45 cells. Western blot analysis elucidated that: a) Xanthatin downregulated expression of Chk1 and Chk2 and phosphorylation of CDC2, which are known as key G2/M transition regulators; b) Xanthatin increased p53 activation, decreased the bcl-2/bax ratio and the levels of downstream procaspase-9 and procaspase-3, which are key regulators in the intrinsic apoptosis pathway; c) Xanthatin blocked phosphorylation of NF-kappaB (p65 subunit) and of IkappaBalpha, which might contribute to its proapoptotic effects on MKN-45 cells. In conclusion, our results suggest that Xanthatin may have therapeutic potential against human gastric carcinoma.

Description

Xanthatin is isolated from Xanthium strumarium leaves. Xanthatin exhibits strong antitumor activities against a variety of cancer cells through apoptosis persuasion and shows anti-inflammatory activities by inhibiting PGE2 synthesis and 5-lipoxygenase activity. Xanthatin is a potent and orally active inhibitor of VEGFR2 kinase activity with an IC50 of 3.8 μM and prominently blocks the phosphorylation of VEGFR2 at Tyr951 site. Xanthatin inhibits angiogenesis and has the potential for the investigation of breast cancer.

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