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Dephnoretin

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-D2034

  • Specification : 98%

  • CAS number : 2034-69-7

  • Formula : C19H12O7

  • Molecular Weight : 352.298

  • PUBCHEM ID : 5281406

  • Volume : 20mg

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Catalogue Number

BF-D2034

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

352.298

Appearance

Yellow powder

Botanical Source

Euphorbia fischeriana,Carthamus tinctorius,Apios fortunei,Wikstroemia indica

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=C2C(=C1)C=C(C(=O)O2)OC3=CC4=C(C=C3)C=CC(=O)O4)O

Synonyms

7-hydroxyl-6-methoxy-3,7'-dicoumarylether/7-hydroxy-6-methoxy-3,7'-dicoumaryl ether/Thymelol/7-hydroxy-6-methoxy-3-(2-oxochromen-7-yl)oxychromen-2-one/COUMARIN,7-HYDROXY-6-METHOXY-3,7'-OXYDI/6-methoxy-7-hydroxy-3,7'-dicoumaric ether/2H-1-Benzopyran-2-one, 7-hydroxy-6-methoxy-3-[(2-oxo-2H-1-benzopyran-7-yl)oxy]-/Daphnoretin/7-Hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one

IUPAC Name

7-hydroxy-6-methoxy-3-(2-oxochromen-7-yl)oxychromen-2-one

Density

1.5±0.1 g/cm3

Solubility

Methanol; Ethanol; Dichloromethane

Flash Point

237.8±25.0 °C

Boiling Point

639.6±55.0 °C at 760 mmHg

Melting Point

245-246℃

InChl

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

InChl Key

JRHMMVBOTXEHGJ-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932200000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:2034-69-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

8216237

Abstract

Daphnoretin, a biologically active principle isolated from Wikstroemia indica C.A. Mey., caused platelet aggregation in washed rabbit platelets, platelet-rich plasma and whole blood. The aggregation of and ATP release from platelets induced by daphnoretin were similar to phorbol ester- and diacylglycerol-induced aggregation and release. The EC50 values of daphnoretin-, phorbol 12,13-dibutyrate (PDBu)- and 1-oleoyl-2-acetylglycerol (OAG)-induced platelet aggregation in washed rabbit platelets were 17.2 +/- 2.8 microM, 20.6 +/- 2.1 nM and 38.6 +/- 1.7 microM respectively. Platelet aggregation induced by daphnoretin and PDBu was not inhibited by indomethacin, BN52021 or sodium nitroprusside. ADP-scavenging systems, apyrase and phosphocreatine/creatine kinase, showed weak inhibition of the aggregation, and EGTA, triflavin, verapamil and prostaglandin E1 markedly inhibited the aggregation. Staurosporine, a potent protein kinase C inhibitor, suppressed daphnoretin-, PDBu- and OAG-induced aggregation and ATP release in a concentration-dependent manner. The IC50 values of staurosporine on daphnoretin (50 microM)-, PDBu (100 nM)- and OAG (50 microM)-induced aggregation were 37.7 +/- 8.3, 52.2 +/- 6.3 and 42.8 +/- 8.9 nM respectively. Daphnoretin did not cause significant thromboxane B2 formation in rabbit platelets. Neither daphnoretin nor PDBu caused [3H]inositol monophosphate formation or an increase in intracellular Ca2+ concentration in myo-[3H]inositol-labelled and Fura-2-loaded platelets. Platelet cytosolic protein kinase C was activated by daphnoretin and PDBu in a concentration-dependent manner with an EC50 of 12.4 +/- 1.2 microM and 18.7 +/- 1.4 nM respectively. Membrane-associated protein kinase C activity was increased by either daphnoretin or PDBu. [3H]PDBu binding to washed rabbit platelets was inhibited by daphnoretin in a concentration-dependent manner with an IC50 value of 45.2 +/- 5.2 microM. These results indicate that daphnoretin is a protein kinase C activator in rabbit platelets.

Title

Daphnoretin, a New Protein Kinase C Activator Isolated From Wikstroemia Indica C.A. Mey

Author

F N Ko 1 , Y L Chang, Y H Kuo, Y L Lin, C M Teng

Publish date

1993 Oct 1

PMID

30841414

Abstract

The regulation of Daphnoretin on specific tumours (e.g. cervical cancer, lung cancer, osteosarcoma) has been documented, which still remains unclear for colon cancer cells. Our study explored the suppression of Daphnoretin and its molecular mechanism on the proliferation, apoptosis, invasion and migration of human colon cancer cell line HCT116. Our report showed the activity of HCT116 declined with time- and dose- dependence after Daphnoretin intervention, and a rise in G0/G1 ratio and decrease in G2/M ratio was observed. Daphnoretin-treated HCT116 had declined invasion and migration, increased apoptosis rate, and variations in gene expressions related to the Akt signal pathway. Those results indicated that Daphnoretin can inhibit the proliferation, invasion, and migration of HCT116 and promote its apoptosis by regulating the activity of Akt signal pathway.

Title

Daphnoretin: An Invasion Inhibitor and Apoptosis Accelerator for Colon Cancer Cells by Regulating the Akt Signal Pathway

Author

Suyang Yu 1 , Hong Guo 2 , Xin Gao 3 , Meng Li 1 , Honglei Bian 1

Publish date

2019 Mar

PMID

28772243

Abstract

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.

KEYWORDS

Daphnoretin; Dendritic cell; Differentiation; JNK; Maturation.

Title

Daphnoretin Modulates Differentiation and Maturation of Human Dendritic Cells Through Down-Regulation of c-Jun N-terminal Kinase

Author

Chien-An Chen 1 , Chien-Kuo Liu 2 , Ming-Ling Hsu 3 , Chih-Wen Chi 3 , Chun-Chuan Ko 3 , Jian-Syun Chen 4 , Cheng-Ta Lai 4 , Hen-Hong Chang 5 , Tzung-Yan Lee 6 , Yuen-Liang Lai 7 , Yu-Jen Chen 8

Publish date

2017 Oct


Description :

Daphnoretin (Dephnoretin), isolated from Wikstroemia indica, possesses antiviral activity[1]. Daphnoretin likes PMA, may direct activation of protein kinase C which in turn activated NADPH oxidase and elicited respiratory burst[2].