+86-28-82633987
Product name: Dephnoretin
Synonym name: Thymelol
Catalogue No.: BP0484
Cas No.: 2034-69-7
Formula: C19H12O7
Mol Weight: 352.298
Botanical Source: Wikstroemia indica (Linn.) C. A. Mey
Physical Description:
Type of Compound: Coumarins
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
Description:
Daphnoretin has strong antiviral activity, mainly on the later phase of the replication cycle. Daphnoretin has anticancer effects on leukemia, osteosarcoma and uterine cervix cancer cells, might through promoting apoptosis in a mitochondria-mediated way; it causes death of HOS cells by blocking cells successively in G2/M phases and activating the caspase-3 pathway.
References:
Oncol Lett. 2014 Sep;8(3):1139-1142.
Effect of daphnoretin on the proliferation and apoptosis of A549 lung cancer cells in vitro.
Daphnoretin is an active constituent of Wikstroemia indica C.A. Mey., which is widely distributed in the northwest and southwest regions of China. Previous studies have shown that Daphnoretinhas anticancer effects on leukemia, osteosarcoma and uterine cervix cancer cells. However, the effect of Daphnoretin on human lung cancer cells has yet to be elucidated.
METHODS AND RESULTS:
In the present study, Daphnoretin was observed to inhibit A549 lung cancer cell proliferation in a concentration- and time-dependent manner. Fluorescent microscopy and flow cytometric analysis showed that Daphnoretin induced A549 cell apoptosis in a concentration-dependent manner. Western blot analysis also revealed that Daphnoretin induced apoptosis through the regulation of the B-cell lymphoma-2 gene family in A549 cells.
CONCLUSIONS:
These findings indicate that Daphnoretin may have potential as a therapeutic agent for the management of lung cancer.
Molecules. 2012 Jan 9;17(1):598-612.
Daphnoretin induces cell cycle arrest and apoptosis in human osteosarcoma (HOS) cells.
In this study antiproliferation, cell cycle arrest and apoptosis induced by Daphnoretin in human osteosarcoma (HOS) cells were investigated.
METHODS AND RESULTS:
Antiproliferative activity was measured with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The IC(50) value of Daphnoretin was 3.89 μM after 72 h treatment. Induction of apoptosis was evidenced by apoptotic body appearance and Annexin V-FITC/PI apoptosis detection kit. Flow cytometric analysis indicated Daphnoretin arrested the cell cycle in the G2/M phase. Western-blot assay showed that the G2/M phase arrest was accompanied by down-regulation of cdc2, cyclin A and cyclin B1. Moreover, Daphnoretin inhibited Bcl-2 expression and induced Bax expression to desintegrate the outer mitochondrial membrane and causing cytochrome c release. Mitochondrial cytochrome c release was associated with the activation of caspase-9 and caspase-3 cascade.
CONCLUSIONS:
Our results demonstrated that Daphnoretin caused death of HOS cells by blocking cells successively in G2/M phases and activating the caspase-3 pathway.
Phytother Res. 2010 May;24(5):657-61.
Antiviral activity of daphnoretin isolated from Wikstroemia indica.
METHODS AND RESULTS:
The ethanol extract of Wikstroemia indica was fractionated with organic solvents of different polarities, and various fractions were screened for their antiviral activity against respiratory syncytial virus (RSV) using a cytopathic effect (CPE) reduction assay. The ethyl acetate fraction was most active against RSV with 50% inhibition concentration (IC(50)) value < 3.9 microg/mL and a selectivity index (SI) > 64.1. Further isolation and purification of the fraction led to a purified compound, Daphnoretin. Daphnoretin was tested for its anti-RSV activity using a plaque reduction assay and found active against RSV, with an IC(50 )value of 5.87 microg/mL and SI value of 28.17.
CONCLUSIONS:
The mode of antiviral action study revealed that Daphnoretin could slightly inhibit the early events of the viral infection but its effect was mainly on the later phase of the replication cycle.
HPLC of Dephnoretin
HNMR of Dephnoretin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
99.1100
2.9635
2.8524
.0004
4.5308
23.1850
High
90.0381
2.4755
Yes
No
Yes
No
Yes
Yes
0.9
No
No
Yes
Yes
Dephnoretin, CAS number 2034-69-7, is an important natural coumarin-type compound, attracting attention for its unique chemical structure and diverse biological activities. As a coumarin-derived derivative, Xiruinin demonstrates broad pharmacological potential in pharmacological research of traditional Chinese medicine and modern natural products, especially in antiviral, anti-tumor, and metabolic disease regulation. In recent years, with advances in molecular biology and medicinal chemistry, the mechanism of xilaixiangin and its interactions with various disease-related molecular targets have become clearer, laying a solid foundation for its development as a novel drug. This article will systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of cyrin, aiming to provide researchers in the field of natural product pharmacology with comprehensive and in-depth reference.
Cyromanin belongs to the coumarin-class compounds, with a molecular formula C20H16O6 and a molecular weight of 352.2980. Its structural feature is the substitution of a 7-position hydroxyl group, 6-position methoxy group, and 3-position (2-oxo-2H-chromen-7-yl) oxygen group, forming a composite structure of aromatic ether and hydroxycoumarin. This structure gives sirypoxin strong biological activity and good drug compatibility.
In terms of physicochemical properties, the LogP value of cyroprinis is about 2.96, indicating moderate lipid solubility that facilitates cell membrane penetration. The polarized surface area (TPSA) is 99.11 Ų, indicating moderate polarity and favorable binding to biological macromolecules. Low water solubility (0.0004 mg/mL) suggests limited solubility in the aqueous phase, which may affect bioavailability. The high penetration ability of the blood-brain barrier suggests its potential application in central nervous system diseases. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames mutagenic test score was 0.9, indicating low genotoxicity risk and good safety.
Cysaifen is mainly found in various plants, especially certain Chinese medicinal herbs and aromatic plants rich in coumarins. Common source plants include Daphne spp. and certain Umbelliferae plants. The content of sisanchuin in plants varies depending on species, geographical environment, and harvest time.
In terms of extraction methods, traditional methods have used organic solvent extraction and separation technology. Common extraction solvents include ethanol, methanol, and ethyl acetate, combined with ultrasound-assisted extraction or reflux extraction to improve extraction efficiency. The extract is purified by liquid-liquid distribution, column chromatography (silica gel, C18 reversed phase column), and high-performance liquid chromatography (HPLC), ultimately obtaining high-purity cyrox. In addition, modern green extraction technologies such as supercritical CO2 extraction and microwave-assisted extraction are gradually being applied to the extraction of cyroxin, balancing efficiency and environmental protection.
Numerous in vivo and in vitro experiments have shown that Siricinol possesses a variety of significant pharmacological activities, covering antiviral, anti-tumor, and metabolic regulation fields.
Antiviral activity
Cyrixiang indigo exhibits inhibitory effects on various viruses, especially showing significant inhibitory effects against hepatitis B virus (HBV) and herpesvirus infections. By regulating host immune responses and viral replication-related signaling pathways, it reduces viral load and expression of virus-related proteins, demonstrating good antiviral potential.
Antitumor activity
In various tumor models such as breast and lung cancer, sirikanthin has demonstrated the ability to inhibit tumor cell proliferation, induce apoptosis, and suppress tumor metastasis. Its effects involve regulating apoptosis-related proteins (such as BCL2), signal-transducting molecules (such as STAT3, MAPK1), and multidrug resistance-related proteins (such as ABCB1, ABCG2), and have regulatory effects on the tumor microenvironment and tumor cell drug resistance.
Metabolic regulation
Cyroxin-sifolin has shown potential in the treatment of diabetes and metabolic syndrome. By activating the AMPK signaling pathway and regulating glucose transporter (SGLT2) and glucose metabolism enzyme (GCK), it helps improve insulin sensitivity and blood glucose control. In addition, it also has a positive effect on lipid metabolism and the regulation of oxidative stress.
Other pharmacological effects
Cyroxinin also exhibits anti-inflammatory, antioxidant, and neuroprotective effects, possibly related to its regulation of inflammatory and oxidative stress-related factors such as NFKB and NFE2L2. These effects provide a theoretical basis for its application in chronic inflammatory diseases and neurodegenerative disorders.
The multi-target mechanism of siridesin forms the basis of its broad pharmacological activity. Through molecular docking, gene expression analysis, and proteomics studies, its main targets have been identified as covering key proteins in multiple signaling pathways.
AMPK（PRKAA1）
As a core regulator of energy metabolism, AMPK activation is an important mechanism for cyclogenin to regulate metabolism and anti-tumor effects. Cyroprin promotes AMPK phosphorylation, enhances cellular energy metabolism, and inhibits tumor cell proliferation and metabolic adaptation.
BCL2 family proteins
Cyroxinin regulates BCL2 expression, promotes tumor cell apoptosis, reverses anti-apoptotic signaling, and enhances sensitivity to chemotherapy drugs.
STAT3 signaling pathway
STAT3, as a key factor in tumor cell proliferation and immune evasion, is inhibited by siridene, blocking tumor cell growth signals.
SGLT2 and GCK
In diabetes models, cyroxin-mediated glucose reabsorption and GCK glucose metabolism activity are regulated by SGLT2, improving glycemic metabolism.
NFKB1, TNF, IL6, and NLRP3
Cyrinin exerts anti-inflammatory effects by inhibiting the NFKB signaling pathway, reducing the expression of inflammatory factors TNF and IL6, and inhibiting activation of NLRP3 inflammasomes.
ABCB1、ABCG2、ABCA1
As a multidrug resistance-related transporter, sirikin regulates these targets, helping to reverse tumor cell resistance.
TLR3, TLR4, and IRF3
In antiviral immunity, cyroxin-like hormone enhances the body's antiviral response by modulating the toll-like receptor signaling pathway.
In summary, Cyrofen achieves its broad pharmacological effects through multi-target and multi-pathway synergistic effects, demonstrating the advantages of natural product multi-target drugs.
Druggability evaluation of sirixiangin indicates it has promising potential for drug development. Molecular weight 352.3 complies with Lipinski's rule, with moderate LogP, which is beneficial for cell membrane penetration and distribution in vivo. Its high blood-brain barrier penetration ability gives it an advantage in treating central nervous system diseases.
Low water solubility may limit its oral bioavailability, so formulation modifications (such as nanocarriers and solid dispersions) are needed to enhance solubility and absorption. Negative hERG channel inhibition suggests a low risk of cardiotoxicity, and Ames trial results support its genetic safety.
Pharmacokinetic studies have shown that siridesin has good stability and distribution characteristics in the body, but its metabolic pathways and clearance mechanisms still require further research. Preliminary data suggest it may be metabolized via the hepatic CYP450 enzyme system, posing potential drug interaction risks that require further systematic evaluation.
Thanks to its multi-target and multifunctional pharmacological activity, cyrindistinct shows broad clinical application prospects in the treatment of various diseases.
Metabolic diseases
Cyribanin is expected to become a novel treatment for diabetes and metabolic syndrome by modulating AMPK and sugar-related targets, especially suitable for combining with existing therapies to improve metabolic disorders.
Tumor treatment
Its antitumor activity and reversal of drug resistance in solid tumors such as breast and lung cancer offer new ideas for comprehensive tumor treatment. In the future, targeted drugs and immunotherapy can be combined to enhance treatment outcomes.
Antiviral therapy
For hepatitis B and herpes virus infections, cyrixiang has the potential to develop new antiviral drugs by regulating immune and viral replication mechanisms, especially in the prevention and control of drug-resistant strains.
Inflammation and neuroprotection
Its anti-inflammatory and neuroprotective effects offer potential for the treatment of chronic inflammatory and neurodegenerative diseases, and are worth conducting related preclinical and clinical studies.
Future research should focus on optimizing the dosage form of siruin, improving pharmacokinetics, systematic evaluation of toxicology, and designing clinical trials, promoting its transition from the laboratory to clinical application.
As a natural coumarin-type compound with multiple biological activities, Xiruin, with its unique chemical structure and multi-target mechanism, shows broad application prospects in the fields of antiviral, anti-tumor, and metabolic disease treatment. Its excellent druggability parameters and safety evaluation lay the foundation for further drug development. In the future, through in-depth mechanistic research, pharmacokinetic optimization, and clinical validation, Cyrintin is expected to become an important representative of natural product drug development, contributing new therapeutic approaches to human health. The field of natural product pharmacology should continue to monitor research progress on sirikin and promote its clinical translation.
Shenshuai
Wenjing
Hedandan
