Daphnoretin | CAS#2034-69-7 | anti-cancer

Daphnoretin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 471028

CAS#: 2034-69-7

Description: Daphnoretin, also know as NSC291852, is an active constituent of Wikstroemia indica C. A. Meys which possesses anti-cancer activity. Inhibitory effect on mitosis. Daphnoretin also reduces proliferation, invasion, and migration of HCT116 colon cancer cells in a concentration-dependent manner

Chemical Structure

Daphnoretin

CAS# 2034-69-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 471028
Name: Daphnoretin
CAS#: 2034-69-7
Chemical Formula: C19H12O7
Exact Mass: 352.06
Molecular Weight: 352.298
Elemental Analysis: C, 64.78; H, 3.43; O, 31.79

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 320
25mg	USD 620
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Daphnoretin, NSC 291852, NSC291852, NSC-291852, BRN 1299325, BRN1299325, BRN-1299325

IUPAC/Chemical Name: 7-hydroxy-6-methoxy-3-((2-oxo-2H-chromen-7-yl)oxy)-2H-chromen-2-one

InChi Key: JRHMMVBOTXEHGJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H12O7/c1-23-16-6-11-7-17(19(22)26-15(11)9-13(16)20)24-12-4-2-10-3-5-18(21)25-14(10)8-12/h2-9,20H,1H3

SMILES Code: O=C1OC2=C(C=C1)C=CC(OC3=CC4=C(OC3=O)C=C(C(OC)=C4)O)=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

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Biological target:	Daphnoretin (Dephnoretin), isolated from Wikstroemia indica, possesses antiviral activity and directly activates protein kinase C which in turn activates NADPH oxidase and elicits respiratory burst.
In vitro activity:	To investigate the apoptosis-inducing effect of daphnoretin, A549 cells were treated with various concentrations of daphnoretin. Following treatment with daphnoretin (0 and 10 μmol/l) for 24 h, cells were analyzed using fluorescent microscopy with Hoechst 33324 staining. As shown in Fig. 3, chromatin condensation, nuclear fragmentation and apoptotic bodies were observed in the treated cells. The results revealed that when exposed to daphnoretin, A549 cells underwent the typical morphological changes that are associated with apoptosis. The ratio of apoptotic cells induced by daphnoretin was measured using flow cytometry. A549 cells were treated with various concentrations of daphnoretin (0, 5, 10 and 15 μmol/l) for 24 h and analyzed using flow cytometry with Annexin V and PI staining. As shown in Fig. 4, the ratio of early and late apoptotic cells was observed to be significantly increased in the daphnoretin-treated cells compared with the cells in the control group. The results show that when treated with daphnoretin for 24 h, the ratio of apoptotic cells significantly increased in a concentration-dependent manner. Reference: Oncol Lett. 2014 Sep; 8(3): 1139–1142. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4114638/
In vivo activity:	In disease model related to maturation of DCs (dendritic cells), daphnoretin suppressed the acute rejection of skin allografts in mice. These results suggest that daphnoretin modulated differentiation and maturation of DCs toward a state of atypical maturation with impaired allostimulatory function and this effect may go through down-regulation of phosphorylated JNK. Reference: Int Immunopharmacol. 2017 Oct;51:25-30. https://pubmed.ncbi.nlm.nih.gov/28772243/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	283.85

Preparing Stock Solutions

The following data is based on the product molecular weight 352.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Gu S, He J. Daphnoretin induces cell cycle arrest and apoptosis in human osteosarcoma (HOS) cells. Molecules. 2012 Jan 9;17(1):598-612. doi: 10.3390/molecules17010598. PMID: 22231496; PMCID: PMC6268824. 2. Jiang HF, Wu Z, Bai X, Zhang Y, He P. Effect of daphnoretin on the proliferation and apoptosis of A549 lung cancer cells in vitro. Oncol Lett. 2014 Sep;8(3):1139-1142. doi: 10.3892/ol.2014.2296. Epub 2014 Jun 30. PMID: 25120673; PMCID: PMC4114638. 3. Jegal J, Park NJ, Lee SY, Jo BG, Bong SK, Kim SN, Yang MH. Quercitrin, the Main Compound in Wikstroemia indica, Mitigates Skin Lesions in a Mouse Model of 2,4-Dinitrochlorobenzene-Induced Contact Hypersensitivity. Evid Based Complement Alternat Med. 2020 Jul 9;2020:4307161. doi: 10.1155/2020/4307161. PMID: 32695208; PMCID: PMC7368186 4. Chen CA, Liu CK, Hsu ML, Chi CW, Ko CC, Chen JS, Lai CT, Chang HH, Lee TY, Lai YL, Chen YJ. Daphnoretin modulates differentiation and maturation of human dendritic cells through down-regulation of c-Jun N-terminal kinase. Int Immunopharmacol. 2017 Oct;51:25-30. doi: 10.1016/j.intimp.2017.07.021. Epub 2017 Aug 1. PMID: 28772243.
In vitro protocol:	1. Gu S, He J. Daphnoretin induces cell cycle arrest and apoptosis in human osteosarcoma (HOS) cells. Molecules. 2012 Jan 9;17(1):598-612. doi: 10.3390/molecules17010598. PMID: 22231496; PMCID: PMC6268824. 2. Jiang HF, Wu Z, Bai X, Zhang Y, He P. Effect of daphnoretin on the proliferation and apoptosis of A549 lung cancer cells in vitro. Oncol Lett. 2014 Sep;8(3):1139-1142. doi: 10.3892/ol.2014.2296. Epub 2014 Jun 30. PMID: 25120673; PMCID: PMC4114638.
In vivo protocol:	1. Jegal J, Park NJ, Lee SY, Jo BG, Bong SK, Kim SN, Yang MH. Quercitrin, the Main Compound in Wikstroemia indica, Mitigates Skin Lesions in a Mouse Model of 2,4-Dinitrochlorobenzene-Induced Contact Hypersensitivity. Evid Based Complement Alternat Med. 2020 Jul 9;2020:4307161. doi: 10.1155/2020/4307161. PMID: 32695208; PMCID: PMC7368186. 2. Chen CA, Liu CK, Hsu ML, Chi CW, Ko CC, Chen JS, Lai CT, Chang HH, Lee TY, Lai YL, Chen YJ. Daphnoretin modulates differentiation and maturation of human dendritic cells through down-regulation of c-Jun N-terminal kinase. Int Immunopharmacol. 2017 Oct;51:25-30. doi: 10.1016/j.intimp.2017.07.021. Epub 2017 Aug 1. PMID: 28772243.

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1: Xie Q, Fan X, Han Y, Wu BX, Zhu B. Daphnoretin Arrests the Cell Cycle and Induces Apoptosis in Human Breast Cancer Cells. J Nat Prod. 2022 Oct 28;85(10):2332-2339. doi: 10.1021/acs.jnatprod.2c00504. Epub 2022 Sep 26. PMID: 36154031.

2: Wang H, Hu X, Li M, Pan Z, Li D, Zheng Q. Daphnoretin induces reactive oxygen species-mediated apoptosis in melanoma cells. Oncol Lett. 2021 Jun;21(6):453. doi: 10.3892/ol.2021.12714. Epub 2021 Apr 8. PMID: 33907563; PMCID: PMC8063224.

3: Zhou J, Wang Q. Daphnoretin relieves IL-1β-mediated chondrocytes apoptosis via repressing endoplasmic reticulum stress and NLRP3 inflammasome. J Orthop Surg Res. 2022 Nov 16;17(1):487. doi: 10.1186/s13018-022-03316-w. PMID: 36384642; PMCID: PMC9670399.

4: Huang YC, Huang CP, Lin CP, Yang KC, Lei YJ, Wang HP, Kuo YH, Chen YJ. Naturally Occurring Bicoumarin Compound Daphnoretin Inhibits Growth and Induces Megakaryocytic Differentiation in Human Chronic Myeloid Leukemia Cells. Cells. 2022 Oct 16;11(20):3252. doi: 10.3390/cells11203252. PMID: 36291120; PMCID: PMC9600978.

5: Chen CA, Liu CK, Hsu ML, Chi CW, Ko CC, Chen JS, Lai CT, Chang HH, Lee TY, Lai YL, Chen YJ. Daphnoretin modulates differentiation and maturation of human dendritic cells through down-regulation of c-Jun N-terminal kinase. Int Immunopharmacol. 2017 Oct;51:25-30. doi: 10.1016/j.intimp.2017.07.021. Epub 2017 Aug 1. PMID: 28772243.

6: Yang ZY, Kan JT, Cheng ZY, Wang XL, Zhu YZ, Guo W. Daphnoretin-induced apoptosis in HeLa cells: a possible mitochondria-dependent pathway. Cytotechnology. 2014 Jan;66(1):51-61. doi: 10.1007/s10616-013-9536-8. Epub 2013 Oct 4. PMID: 24091880; PMCID: PMC3886545.

7: Yu S, Guo H, Gao X, Li M, Bian H. Daphnoretin: An invasion inhibitor and apoptosis accelerator for colon cancer cells by regulating the Akt signal pathway. Biomed Pharmacother. 2019 Mar;111:1013-1021. doi: 10.1016/j.biopha.2019.01.003. Epub 2019 Jan 10. PMID: 30841414.

8: Wang JP, Raung SL, Kuo YH, Teng CM. Daphnoretin-induced respiratory burst in rat neutrophils is, probably, mainly through protein kinase C activation. Eur J Pharmacol. 1995 Feb 15;288(3):341-8. doi: 10.1016/0922-4106(95)90047-0. PMID: 7774678.

9: Ko FN, Chang YL, Kuo YH, Lin YL, Teng CM. Daphnoretin, a new protein kinase C activator isolated from Wikstroemia indica C.A. Mey. Biochem J. 1993 Oct 1;295 ( Pt 1)(Pt 1):321-7. doi: 10.1042/bj2950321. PMID: 8216237; PMCID: PMC1134857.

10: Gu S, He J. Daphnoretin induces cell cycle arrest and apoptosis in human osteosarcoma (HOS) cells. Molecules. 2012 Jan 9;17(1):598-612. doi: 10.3390/molecules17010598. PMID: 22231496; PMCID: PMC6268824.

11: Jiang HF, Wu Z, Bai X, Zhang Y, He P. Effect of daphnoretin on the proliferation and apoptosis of A549 lung cancer cells in vitro. Oncol Lett. 2014 Sep;8(3):1139-1142. doi: 10.3892/ol.2014.2296. Epub 2014 Jun 30. PMID: 25120673; PMCID: PMC4114638.

12: Yan H, Ouyang T, Yang QL, Xiang B, Xia XH. [Tissue distribution of galactosyl daphnoretin liposomes in rats]. Zhongguo Zhong Yao Za Zhi. 2016 Sep;41(18):3457-3462. Chinese. doi: 10.4268/cjcmm20161823. PMID: 28925132.

13: Lin LC, Yang KY, Chen YF, Wang SC, Tsai TH. Measurement of daphnoretin in plasma of freely moving rat by liquid chromatography. J Chromatogr A. 2005 May 6;1073(1-2):285-9. doi: 10.1016/j.chroma.2004.09.041. PMID: 15909531.

14: Liang Y, Xu L, Yang H, Xu W, Hu R, Fan X, Liu Y. Analysis on the interaction and binding properties of daphnoretin and human serum albumin in the presence of cisplatin: multi-spectroscopic methods and docking simulation. Eur J Pharm Sci. 2021 Apr 1;159:105723. doi: 10.1016/j.ejps.2021.105723. Epub 2021 Jan 19. PMID: 33482316.

15: Zheng L, Yang WW, Guo JY, Jia YR, Sun LX. Stability of daphnoretin in vitro. Pharmazie. 2012 Apr;67(4):277-82. PMID: 22570931.

16: Zhang TZ, Wei CY, Xu GH, Park SW. 7-Hydroxy-6-methoxy-3-[(2-oxo-2H-1-benzopyran-7-yl)oxy]-2H-1-benzopyran-2-one. Acta Crystallogr C. 2006 Feb;62(Pt 2):o86-8. doi: 10.1107/S0108270106000874. Epub 2006 Jan 21. PMID: 16456294.

17: Ho WS, Xue JY, Sun SS, Ooi VE, Li YL. Antiviral activity of daphnoretin isolated from Wikstroemia indica. Phytother Res. 2010 May;24(5):657-61. doi: 10.1002/ptr.2935. PMID: 19610034.

18: Hu YY, Cao SL, Lin LF, Fu J, Dong XX, Yang CJ, Zhang M, Ni J. [Simultaneous determination of daphnetin, daphnoretin, daphneticin in rat plasma by LC-MS/MS and its application in pharmacokinetic study]. Zhongguo Zhong Yao Za Zhi. 2017 May;42(10):1964-1970. Chinese. doi: 10.19540/j.cnki.cjcmm.20170307.003. PMID: 29090558.

19: Liliana Porras-Dávila S, Zamilpa A, Jiménez-Ferrer E, Jiménez-Aparicio A, Alejandra Santillan-Urquiza M, Díaz-Patricio F, Herrera-Ruiz M. Anti- Inflammatory and Neuroprotective Effects of Standardized Fractions in Herniarin and Daphnoretin from Distictis buccinatoria. Chem Biodivers. 2023 May;20(5):e202200969. doi: 10.1002/cbdv.202200969. PMID: 36973180.

20: Zhu G, Wang B, Feng G, Zhou Z, Li W, Liu W, Su H, Wang W, Wang T, Yu XA. A nano-preparation approach to enable the delivery of daphnoretin to potentiate the therapeutical efficacy in hepatocellular cancer. Front Pharmacol. 2022 Sep 28;13:965131. doi: 10.3389/fphar.2022.965131. PMID: 36249790; PMCID: PMC9554561.

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