Daphnoretin
(Synonyms: 西瑞香素,Dephnoretin; Thymelol) 目录号 : GC38186
A coumarin with diverse biological activities
Cas No.:2034-69-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Daphnoretin is a coumarin that has been found in W. indica and has diverse biological activities.1,2,3 It induces aggregation of washed rabbit platelets (EC50 = 17.2 μM), an effect that is reversed by the protein kinase C (PKC) inhibitor staurosporine .1 Daphnoretin is active against respiratory syncytial virus (RSV) in a plaque reduction assay using HEp-2 cells (IC50 = 5.87 μg/ml).2 It halts the cell cycle at the G2/M phase, induces apoptosis, and inhibits proliferation of human osteosarcoma (HOS) cells (IC50 = 3.89 μM).3 Daphnoretin also reduces proliferation, invasion, and migration of HCT116 colon cancer cells in a concentration-dependent manner.4
1.Feng, N.K.O., Chang, Y.L., Kuo, Y.H., et al.Daphnoretin, a new protein kinase C activator isolated from Wikstroemia indica C.A. MeyBiochem J.295(Pt 1)321-327(1993) 2.Ho, W.-S., Xue, J.-Y., Sun, S.S.M., et al.Antiviral activity of daphnoretin isolated from Wikstroemia indicaPhytother. Res.24(5)657-661(2010) 3.Gu, S., and He, J.Daphnoretin induces cell cycle arrest and apoptosis in human osteosarcoma (HOS) cellsMolecules17(1)598-612(2012) 4.Yu, S., Guo, H., Gao, X., et al.Daphnoretin: An invasion inhibitor and apoptosis accelerator for colon cancer cells by regulating the Akt signal pathwayBiomed. Pharmacother.1111013-1021(2019)
| Cas No. | 2034-69-7 | SDF | |
| 别名 | 西瑞香素,Dephnoretin; Thymelol | ||
| Canonical SMILES | O=C1C(OC2=CC=C(C(O3)=C2)C=CC3=O)=CC4=CC(OC)=C(O)C=C4O1 | ||
| 分子式 | C19H12O7 | 分子量 | 352.29 |
| 溶解度 | DMF: 25 mg/ml,DMSO: 25 mg/ml,Ethanol: partially soluble,PBS (pH >10.2): Partially soluble | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.8386 mL | 14.1929 mL | 28.3857 mL |
| 5 mM | 0.5677 mL | 2.8386 mL | 5.6771 mL |
| 10 mM | 0.2839 mL | 1.4193 mL | 2.8386 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Daphnoretin Arrests the Cell Cycle and Induces Apoptosis in Human Breast Cancer Cells
J Nat Prod 2022 Oct 28;85(10):2332-2339.PMID:36154031DOI:10.1021/acs.jnatprod.2c00504.
Emerging evidence has shown that Daphnoretin, one of the main active ingredients of Daphne giraldii Nitsche, processes antitumor activities in several tumor cells (e.g., colon cancer, lung cancer, cervical cancer, and osteosarcoma). However, the antitumor effect and its mechanism in breast cancer are unexplored. In this study, our data indicated that Daphnoretin obviously suppressed the proliferation of breast cancer MCF-7 and MDA-MB-231 cells. Further studies showed that Daphnoretin remarkably increased the p21 level, decreased cyclin E and CDK2 levels, and then arrested the cell cycle at the S phase. Moreover, Daphnoretin obviously lowered the BCL-2 level and raised the levels of BAX and cleaved caspase-9 and -3, leading to cell apoptosis. Furthermore, Daphnoretin remarkably decreased the ratio of p-PI3K/PI3K and p-AKT/AKT in breast cancer cells. Collectively, these findings demonstrated that Daphnoretin could suppress breast cancer cell proliferation through cell cycle arrest and inducing apoptosis, which is related to the PI3K/AKT pathway.
Daphnoretin induces reactive oxygen species-mediated apoptosis in melanoma cells
Oncol Lett 2021 Jun;21(6):453.PMID:33907563DOI:10.3892/ol.2021.12714.
Research suggests that Daphnoretin exhibits a diverse array of antitumor mechanisms and pharmacological activities. However, there is no definitive explanation for the antitumor mechanisms of Daphnoretin in malignant melanoma. In the present study, MTT and colony formation assays demonstrated that Daphnoretin significantly inhibited the proliferation of melanoma A375 and B16 cells. Following treatment with Daphnoretin, apoptotic bodies were observed in A375 and B16 cells via Hoechst 33258 staining. Furthermore, western blot analysis revealed that the apoptosis-related proteins cleaved caspase-3, cleaved caspase-9, Bax, cytochrome c and apoptotic protease-activating factor 1 were significantly upregulated, while the expression levels of caspase-3, caspase-9 and Bcl-2 were downregulated in A375 and B16 cells. Flow cytometry and fluorescence microscopy revealed that Daphnoretin induced higher levels of reactive oxygen species (ROS). Therefore, the results of the present study indicated that Daphnoretin induced ROS-mediated mitochondria apoptosis in human (A375) and murine (B16) malignant melanoma cells.
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.PMID:36384642DOI:10.1186/s13018-022-03316-w.
Background: Osteoarthritis (OA), mainly caused by severe joint degeneration, is often accompanied by joint pain and dysfunction syndrome. Inflammatory mediators and apoptosis play key roles in the evolution of OA. It is reported that Daphnoretin has significant antiviral and anti-tumor values. The present study aims at investigating the role of Daphnoretin in OA. Methods: The OA mouse model was constructed by performing the destabilization of the medial meniscus through surgery, and the OA cell model was induced in ATDC5 chondrocytes with IL-1β (10 ng/mL) in vitro. Chondrocyte viability and apoptosis were measured by 3-(4,5)-dimethylthiahiazo (-z-y1)-3,5-di-phenytetrazoliumromide (MTT), Caspase-3 activity, and flow cytometry. The levels of COX-2, iNOS, TNF-α, IL-6, Bax, Bcl2, cleaved-Caspase3, endoplasmic reticulum stress (ERS) proteins (GRP78, CHOP, ATF6, and Caspase-12), and NLRP3-ASC-Caspase1 inflammasome were determined by quantitative real-time PCR or western blot. The concentrations of TNF-α, IL-6, and PGE2 were tested by enzyme-linked immunosorbent assay. The content of nitrates was detected by the Griess method. In vivo, morphologic differences in knee joint sections and the thickness of the subchondral bone density plate in mice were observed by hematoxylin-eosin (H&E) staining and safranin O-fast green staining. Results: Daphnoretin effectively choked IL-1β-induced chondrocyte apoptosis and facilitated cell viability. Daphnoretin dose-dependently abated ERS, inflammatory mediators, and the activation of NLRP3 inflammasomes in IL-1β-induced chondrocytes. What's more, in vivo experiments confirmed that Daphnoretin alleviated OA progression in a murine OA model by mitigating inflammation and ERS. Conclusion: Daphnoretin alleviated IL-1β-induced chondrocyte apoptosis by hindering ERS and NLRP3 inflammasome.
Naturally Occurring Bicoumarin Compound Daphnoretin Inhibits Growth and Induces Megakaryocytic Differentiation in Human Chronic Myeloid Leukemia Cells
Cells 2022 Oct 16;11(20):3252.PMID:36291120DOI:10.3390/cells11203252.
Daphnoretin extracted from the stem and roots of Wikstroemia indica (L.) C.A. Mey has been shown to possess antiviral and antitumor activities. Herein, we hypothesized that Daphnoretin might induce megakaryocytic differentiation, thereby inhibiting the proliferation of cells and serving as a differentiation therapy agent for chronic myeloid leukemia (CML). Daphnoretin-treated K562 and HEL cells were examined for growth inhibition, cell morphology, and megakaryocyte-specific markers. Potential mechanisms of megakaryocytic differentiation of daphnoretin-treated K562 cells were evaluated. The results showed that Daphnoretin inhibited the growth of K562 and HEL cells in a dose- and time-dependent manner. Flow cytometry analyses revealed that Daphnoretin treatment slightly increased the proportion of sub-G1 and polyploid cells compared to that of dimethyl sulfoxide (DMSO)-treated control cells. Morphological examination showed that daphnoretin-treated K562 and HEL cells exhibited enlarged contours and multinucleation as megakaryocytic characteristics compared to DMSO-treated control cells. Daphnoretin treatment also dramatically enhanced the expression of megakaryocytic markers CD61 and CD41. Under optimal megakaryocytic differentiation conditions, Daphnoretin increased the phosphorylation of STAT3 but not STAT5. In summary, Daphnoretin inhibited cell growth and induced megakaryocytic differentiation in K562 and HEL cells. The efficacy of Daphnoretin in vivo and in patients with CML may need further investigations for validation.
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.PMID:28772243DOI:10.1016/j.intimp.2017.07.021.
Daphnoretin, an active constituent of Wikstroemia indica C.A. Meys, has been shown possessing anti-cancer activity. In this study, we examined the effect of Daphnoretin on differentiation and maturation of human myeloid dendritic cells (DCs). After treatment with Daphnoretin (0, 1.1, 3.3, 10 and 30μM) to initiate monocytes, the recovery rate of DCs was reduced in a dose-dependent manner. The mature DCs differentiated in the presence of Daphnoretin had fewer and shorter dendrites. Daphnoretin modulated DCs differentiation and maturation in terms of lower expression of CD1a, CD40, CD83, DC-SIGN, and HLA-DR. Daphnoretin inhibited the allostimulatory activity of DCs on proliferation of naive CD4+CD45+RA+ T cell. On the mitogen-activated protein kinase, Daphnoretin down-regulated the lipopolysaccharide-augmented expression of phosphorylated c-Jun N-terminal kinase (pJNK), but not p38 and extracellular signal-regulated kinase 1/2 (ERK1/2). Activation of JNK by anisomycin reversed the effect of Daphnoretin on daphnoretin-inhibited pJNK expression and dendrite formation of DCs. In disease model related to maturation of DCs, Daphnoretin suppressed the acute rejection of skin allografts in mice. Our 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.