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MedKoo Cat#: 584586 | Name: Daphnetin
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Description:

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

Daphnetin is a coumarin derivative that has been isolated from plants of the genus Daphne and has diverse biological activities, including kinase inhibitory, anti-proliferative, and antioxidative properties.

Chemical Structure

Daphnetin
Daphnetin
CAS#486-35-1

Theoretical Analysis

MedKoo Cat#: 584586

Name: Daphnetin

CAS#: 486-35-1

Chemical Formula: C9H6O4

Exact Mass: 178.0266

Molecular Weight: 178.14

Elemental Analysis: C, 60.68; H, 3.40; O, 35.92

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
250mg USD 650.00 2 Weeks
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Synonym
Daphnetin; 7,8-Dihydroxycoumarin; Daphnetol; Ruixiangsu; NSC 633563; NSC633563; NSC-633563;
IUPAC/Chemical Name
7,8-dihydroxy-2H-1-benzopyran-2-one
InChi Key
ATEFPOUAMCWAQS-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H
SMILES Code
O=C1C=CC2=CC=C(O)C(O)=C2O1
Appearance
Solid powder
Purity
>95% (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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Daphnetin (7,8-dihydroxycoumarin), one coumarin derivative isolated from plants of the Genus Daphne, is a protein kinase inhibitor, with IC50s of 7.67 μM, 9.33 μM and 25.01 μM for EGFR, PKA and PKC in vitro, respectively.
In vitro activity:
The aim of the present study was to explore the function of daphnetin in DN (diabetic nephropathy) and the underlying mechanism in vitro. Daphnetin alleviated cell proliferation induced by high glucose (HG) in human mesangial cells (MCs). Daphnetin strikingly reduced reactive oxygen species (ROS) and malonaldehyde (MDA) levels, and induced the superoxide dismutase (SOD) activity in HG-stimulated MCs. Besides, the production of TNF-α, IL-1β, IL-6, fibronectin (FN) and collagen IV (Col IV) was also inhibited by daphnetin in HG-stimulated MCs. In addition, daphnetin enhanced the expression of nuclear factor-erythroid 2-related factor 2 (Nrf2) and inhibited the levels of p-Akt and p-p65 in HG-stimulated MCs. The results indicated that daphnetin inhibited HG-induced oxidative stress, inflammatory response, and ECM accumulation in human MCs. The effect is partially mediated by Nrf2/keap1 and Akt/NF-κB pathways. The findings suggested that daphnetin might be a therapeutic or preventive agent for DN. Reference: J Pharmacol Sci. 2019 Feb;139(2):91-97. https://pubmed.ncbi.nlm.nih.gov/30595336/
In vivo activity:
The present study aimed to investigate the potential therapeutic effect of daphnetin on inflammation in the NZB/W F1 systemic lupus erythematosus (SLE) murine model. Female NZB/WF1 mice (age, 16-18 weeks) were intraperitoneally injected with daphnetin once a day for 12 weeks. The survival rate of the NZB/WF1 mice in the SLE group was lower than that of the BALB/c mice in the control group (Fig. 2). Of note, daphnetin treatment clearly increased the survival of NZB/WF1 mice with SLE (Fig. 2). Daphnetin treatment significantly reduced BUN levels and therefore renal damage in NZB/WF1 mice. ZB/WF1 mice in the SLE group had significantly higher serum levels of TNF-α and IL-6 than the BALB/c mice in the control group (Fig. 5). Furthermore, daphnetin significantly reduced the serum levels of TNF-α and IL-6 in NZB/WF1 mice as compared with those in the SLE group (Fig. 5). Furthermore, daphnetin significantly reduced the SLE-induced NFAT protein expression in NZB/WF1 mice. In conclusion, daphnetin inhibited inflammation in the NZB/W F1 murine SLE model via inhibition of NF-κB mediated by upregulation of A20. Reference: Exp Ther Med. 2017 Feb;13(2):455-460. https://pubmed.ncbi.nlm.nih.gov/28352315/
Solvent mg/mL mM
Solubility
DMSO 43.0 241.38
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 178.14 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.

Recalculate based on batch purity %
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. Wang Y, Li CF, Pan LM, Gao ZL. 7,8-Dihydroxycoumarin inhibits A549 human lung adenocarcinoma cell proliferation by inducing apoptosis via suppression of Akt/NF-κB signaling. Exp Ther Med. 2013 Jun;5(6):1770-1774. doi: 10.3892/etm.2013.1054. Epub 2013 Apr 9. PMID: 23837071; PMCID: PMC3702713. 2. Xu K, Guo L, Bu H, Wang H. Daphnetin inhibits high glucose-induced extracellular matrix accumulation, oxidative stress and inflammation in human glomerular mesangial cells. J Pharmacol Sci. 2019 Feb;139(2):91-97. doi: 10.1016/j.jphs.2018.11.013. Epub 2018 Dec 7. PMID: 30595336. 3. Wang Y, Li CF, Pan LM, Gao ZL. 7,8-Dihydroxycoumarin inhibits A549 human lung adenocarcinoma cell proliferation by inducing apoptosis via suppression of Akt/NF-κB signaling. Exp Ther Med. 2013 Jun;5(6):1770-1774. doi: 10.3892/etm.2013.1054. Epub 2013 Apr 9. PMID: 23837071; PMCID: PMC3702713 4. Xu K, Guo L, Bu H, Wang H. Daphnetin inhibits high glucose-induced extracellular matrix accumulation, oxidative stress and inflammation in human glomerular mesangial cells. J Pharmacol Sci. 2019 Feb;139(2):91-97. doi: 10.1016/j.jphs.2018.11.013. Epub 2018 Dec 7. PMID: 30595336.
In vitro protocol:
1. Wang Y, Li CF, Pan LM, Gao ZL. 7,8-Dihydroxycoumarin inhibits A549 human lung adenocarcinoma cell proliferation by inducing apoptosis via suppression of Akt/NF-κB signaling. Exp Ther Med. 2013 Jun;5(6):1770-1774. doi: 10.3892/etm.2013.1054. Epub 2013 Apr 9. PMID: 23837071; PMCID: PMC3702713. 2. Xu K, Guo L, Bu H, Wang H. Daphnetin inhibits high glucose-induced extracellular matrix accumulation, oxidative stress and inflammation in human glomerular mesangial cells. J Pharmacol Sci. 2019 Feb;139(2):91-97. doi: 10.1016/j.jphs.2018.11.013. Epub 2018 Dec 7. PMID: 30595336.
In vivo protocol:
1. Du J, Zhao Q, Zhang Y, Wang Y, Ma M. 7, 8-dihydroxycoumarin improves neurological function in a mouse model of sciatic nerve injury. Neural Regen Res. 2012 Feb 25;7(6):445-50. doi: 10.3969/j.issn.1673-5374.2012.06.007. PMID: 25774187; PMCID: PMC4350131. 2. Li M, Shi X, Chen F, Hao F. Daphnetin inhibits inflammation in the NZB/W F1 systemic lupus erythematosus murine model via inhibition of NF-κB activity. Exp Ther Med. 2017 Feb;13(2):455-460. doi: 10.3892/etm.2016.3971. Epub 2016 Dec 13. PMID: 28352315; PMCID: PMC5348691.
1: Gao J, Chen F, Fang H, Mi J, Qi Q, Yang M. Daphnetin inhibits proliferation and inflammatory response in human HaCaT keratinocytes and ameliorates imiquimod-induced psoriasis-like skin lesion in mice. Biol Res. 2020 Oct 20;53(1):48. doi: 10.1186/s40659-020-00316-0. PMID: 33081840; PMCID: PMC7576854. 2: Hang S, Wu W, Wang Y, Sheng R, Fang Y, Guo R. Daphnetin, a Coumarin in Genus Stellera Chamaejasme Linn: Chemistry, Bioactivity and Therapeutic Potential. Chem Biodivers. 2022 Sep;19(9):e202200261. doi: 10.1002/cbdv.202200261. Epub 2022 Aug 17. PMID: 35880614. 3: Javed M, Saleem A, Xaveria A, Akhtar MF. Daphnetin: A bioactive natural coumarin with diverse therapeutic potentials. Front Pharmacol. 2022 Sep 29;13:993562. doi: 10.3389/fphar.2022.993562. PMID: 36249766; PMCID: PMC9556945. 4: Gao P, Wang Z, Lei M, Che J, Zhang S, Zhang T, Hu Y, Shi L, Cui L, Liu J, Noda M, Peng Y, Long J. Daphnetin ameliorates Aβ pathogenesis via STAT3/GFAP signaling in an APP/PS1 double-transgenic mouse model of Alzheimer's disease. Pharmacol Res. 2022 Jun;180:106227. doi: 10.1016/j.phrs.2022.106227. Epub 2022 Apr 20. PMID: 35452800. 5: Lv H, Zhu C, Wei W, Lv X, Yu Q, Deng X, Ci X. Enhanced Keap1-Nrf2/Trx-1 axis by daphnetin protects against oxidative stress-driven hepatotoxicity via inhibiting ASK1/JNK and Txnip/NLRP3 inflammasome activation. Phytomedicine. 2020 Jun;71:153241. doi: 10.1016/j.phymed.2020.153241. Epub 2020 May 17. PMID: 32454347. 6: Zhang M, Yu X, Li D, Ma N, Wei Z, Ci X, Zhang S. Nrf2 Signaling Pathway Mediates the Protective Effects of Daphnetin Against D-Galactose Induced- Premature Ovarian Failure. Front Pharmacol. 2022 Jan 28;13:810524. doi: 10.3389/fphar.2022.810524. PMID: 35153783; PMCID: PMC8832979. 7: Nam G, An SK, Park IC, Bae S, Lee JH. Daphnetin inhibits α-MSH-induced melanogenesis via PKA and ERK signaling pathways in B16F10 melanoma cells. Biosci Biotechnol Biochem. 2022 Apr 21;86(5):596-609. doi: 10.1093/bbb/zbac016. PMID: 35325017. 8: Singh L, Singh AP, Bhatti R. Mechanistic interplay of various mediators involved in mediating the neuroprotective effect of daphnetin. Pharmacol Rep. 2021 Oct;73(5):1220-1229. doi: 10.1007/s43440-021-00261-z. Epub 2021 Apr 16. PMID: 33860917. 9: Pei Q, Hu P, Zhang H, Li H, Yang T, Liu R. Daphnetin exerts an anticancer effect by attenuating the pro-inflammatory cytokines. J Biochem Mol Toxicol. 2021 Jun;35(6):1-8. doi: 10.1002/jbt.22759. Epub 2021 Mar 22. PMID: 33749080. 10: Wang D, Zhu B, Liu X, Han Q, Ge W, Zhang W, Lu Y, Wu Q, Shi L. Daphnetin Ameliorates Experimental Autoimmune Encephalomyelitis Through Regulating Heme Oxygenase-1. Neurochem Res. 2020 Apr;45(4):872-881. doi: 10.1007/s11064-020-02960-0. Epub 2020 Jan 16. PMID: 31950453. 11: Zhi J, Duan B, Pei J, Wu S, Wei J. Daphnetin protects hippocampal neurons from oxygen-glucose deprivation-induced injury. J Cell Biochem. 2019 Mar;120(3):4132-4139. doi: 10.1002/jcb.27698. Epub 2018 Sep 27. PMID: 30260007. 12: Liu C, Pan J, Liu H, Lin R, Chen Y, Zhang C. Daphnetin inhibits the survival of hepatocellular carcinoma cells through regulating Wnt/β-catenin signaling pathway. Drug Dev Res. 2022 Jun;83(4):952-960. doi: 10.1002/ddr.21920. Epub 2022 Feb 7. PMID: 35132666. 13: Wang G, Pang J, Hu X, Nie T, Lu X, Li X, Wang X, Lu Y, Yang X, Jiang J, Li C, Xiong YQ, You X. Daphnetin: A Novel Anti-Helicobacter pylori Agent. Int J Mol Sci. 2019 Feb 15;20(4):850. doi: 10.3390/ijms20040850. PMID: 30781382; PMCID: PMC6412720. 14: Liu X, Gao X, Liu Y, Liang D, Fu T, Song Y, Zhao C, Dong B, Han W. Daphnetin inhibits RANKL-induced osteoclastogenesis in vitro. J Cell Biochem. 2019 Feb;120(2):2304-2312. doi: 10.1002/jcb.27555. Epub 2018 Sep 11. PMID: 30206967. 15: Wang D, Lu Z, Zhang H, Jin SF, Yang H, Li YM, Shi LY. Daphnetin Alleviates Experimental Autoimmune Encephalomyelitis via Regulating Dendritic Cell Activity. CNS Neurosci Ther. 2016 Jul;22(7):558-67. doi: 10.1111/cns.12537. Epub 2016 Mar 25. PMID: 27013083; PMCID: PMC6492777. 16: Gao J, Wang Z, Gao P, Fan Q, Zhang T, Cui L, Shi L, Liu Z, Yang Z, He L, Wang C, Li Y, Qu L, Liu J, Long J. Daphnetin Alleviates Senile and Disuse Osteoporosis by Distinct Modulations of Bone Formation and Resorption. Antioxidants (Basel). 2022 Nov 29;11(12):2365. doi: 10.3390/antiox11122365. PMID: 36552574; PMCID: PMC9774389. 17: Zhou R, Wen W, Gong X, Zhao Y, Zhang W. Nephro-protective effect of Daphnetin in hyperoxaluria-induced rat renal injury via alterations of the gut microbiota. J Food Biochem. 2022 Dec;46(12):e14377. doi: 10.1111/jfbc.14377. Epub 2022 Aug 22. PMID: 35994414. 18: Syed AM, Kundu S, Ram C, Kulhari U, Kumar A, Mugale MN, Mohapatra P, Murty US, Sahu BD. Up-regulation of Nrf2/HO-1 and inhibition of TGF-β1/Smad2/3 signaling axis by daphnetin alleviates transverse aortic constriction-induced cardiac remodeling in mice. Free Radic Biol Med. 2022 Jun;186:17-30. doi: 10.1016/j.freeradbiomed.2022.04.019. Epub 2022 May 2. PMID: 35513128. 19: Fisher L. Retraction: Daphnetin inhibits proliferation and glycolysis in colorectal cancer cells by regulating the PI3K/Akt signaling pathway. RSC Adv. 2021 Jan 26;11(9):5023. doi: 10.1039/d1ra90033a. PMID: 35686057; PMCID: PMC9133850. 20: Li T, Yang G, Hao Q, Zhang X, Zhang X. Daphnetin Ameliorates the Expansion of Chemically Induced Hepatocellular Carcinoma via Reduction of Inflammation and Oxidative Stress. J Oleo Sci. 2022;71(4):575-585. doi: 10.5650/jos.ess21415. PMID: 35370216.