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Artemetin

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-A4005

  • Specification : 98%(HPLC)

  • CAS number : 479-90-3

  • Formula : C20H20O8

  • Molecular Weight : 388.38

  • PUBCHEM ID : 5320351

  • Volume : 25mg

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Catalogue Number

BF-A4005

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

388.38

Appearance

Yellow powder

Botanical Source

herbs of Achillea millefolium L.

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)OC)OC)O)OC)OC

Synonyms

3,3',4',7-tetra-O-methylpatuletin/5-hydroxy-3',4',3,6,7-pentamethoxy-flavone/5-Hydroxy-3,3',4',6,7-pentamethoxyflavone/4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-/Flavone, 5-hydroxy-3,3',4',6,7-pentamethoxy-/2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-4H-chromen-4-one/Artemetin/Artemisetin

IUPAC Name

2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxychromen-4-one

Applications

Artemitin is a flavonol found in Laggera pterodonta (DC.) Benth., with antioxidative, anti-inflammatory, and antiviral activity[1].

Density

1.4±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

208.9±23.6 °C

Boiling Point

588.8±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C20H20O8/c1-23-11-7-6-10(8-12(11)24-2)18-20(27-5)17(22)15-13(28-18)9-14(25-3)19(26-4)16(15)21/h6-9,21H,1-5H3

InChl Key

RIGYMJVFEJNCKD-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:479-90-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30073671

Abstract

Artemitin, a significant flavonol compound existing in Laggera pterodonta (DC.) Benth., Artemisia rupestris L, etc., is the subject of attention by researchers owing to its pharmacological activities (such as antioxidative, anti-inflammatory and antiviral). In this work, a highly sensitive and specific high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (HPLC-ESI-MS/MS) assay combined with protein precipitation has been established and validated for determining artemitin concentration in rat plasma. Both artemitin and warfarin sodium (internal standard, IS) were separated on an Agela Venusil XBP Phenyl column through the isocratic elution mode of methanol-water containing 0.1% formic acid (80:20, v/v), at a flow rate of 0.4 mL/min. The MS/MS system was operated in a positive ion and ESI multiple reaction monitoring mode, and the multiple reaction monitoring transition was optimized as m/z 389.0 → 373.0 for artemitin and 309.2 → 163.0 for IS. The method showed good linearity in the range of 2.5-2000 ng/mL (R2 = 1.0000) and high sensitivity for artemitin with the lower limit of quantification of 2.5 ng/mL. The intra- and inter-day accuracies were 97.4-100.9 and 93.4-100.3%, respectively. The intra- and inter-day precisions were <4.8 and 6.5%, respectively. The extraction efficiency and absolute recovery were >66.5 and 71.3%, respectively. In addition, a good matrix effect of <9.5% was obtained. As a result, the method developed herein was successfully applied for the pharmacokinetic study of artemitin after an intravenous administration in rats.

© 2018 John Wiley & Sons, Ltd.

KEYWORDS

HPLC-ESI-MS/MS; artemitin; pharmacokinetics; rat plasma

Title

Development of an LC-MS/MS-based assay to determine artemitin in rat plasma and its application in a pharmacokinetic study.

Author

Han X1,2, He J3, Chen Q1,2, Sun Y1,2, Zhang X1,2, Gu Z3, Sha X1,2.

Publish date

2018 Dec

PMID

28167052

Abstract

A heme-binding assay based on mass spectrometry was performed on P. monodiana Maire (Asteraceae) extracts to identify metabolites able to form adducts with heminic part of haemoglobin, as potential antimalarial drugs. Main adducts were characterized and their stability was measured. Isolation of main constituents of P. monodiana Maire lead to identification of the two methoxyflavones 3′-O-methyleupatorin (7) and artemetin (8) involved in the adducts formation. Four seco-tanapartholides (1-4), a guaianolide (5), a germacranolide (6) and two other methoxyflavones (9, 10) were also characterized. Evaluation of isolated compounds on P. falciparum and T. brucei brucei showed a moderate antiprotozoal activity of the two methoxyflavones.

Copyright © 2017. Published by Elsevier B.V.

Title

Heme-binding activity of methoxyflavones from Pentzia monodiana Maire (Asteraceae).

Author

Ortiz S1, Dali-Yahia K2, Vasquez-Ocmin P3, Grougnet R4, Grellier P5, Michel S6, Maciuk A7, Boutefnouchet S8.

Publish date

2017 Apr

PMID

27314303

Abstract

5,6-Dihydroxy-3,7,4′-trimethoxyflavonol (AH5), 5,6,3′-trihydroxy-3,7,4′-trimethoxyflavonol (AH22), artemetin, and oroxylin A are four flavonoids with the same 2-phenyl-chromone skeleton isolated from the Chinese herb Aster himalaicus. The aim of this study was to evaluate the structure-activity relationship of these four analogs and the mediation of AH5 cytotoxicity via G2/M arrest and apoptosis in human hepatocellular carcinoma (HCC) cells. 3-(4,5-Dimethythiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay indicated AH5 showed the better potency to inhibit proliferation in human HCC cells, which suggested hydroxyl binding to C6 is necessary to anticancer properties, whereas binding to C3′ attenuated the activities and increased toxicity in tested cells. Flow cytometry analysis revealed that AH5-induced G2/M arrest and significantly apoptosis in these cell lines. HepG-2 cells were used to further evaluate the antitumor effects and mechanisms of AH5. AH5-induced apoptosis was further confirmed by 4′,6-diamidino-2-phenylindole (DAPI) staining and the increased ratio of Bax/Bcl-2. Moreover, AH5 induced the release of cytochrome C and the activation of caspase-9 and caspase-3, thus suggesting mitochondria activation might be involved. Western blot showed that AH5 induced the phosphorylation of Cdc2 and decreased the level of Cyclin B1. These results demonstrated that AH5 could be a proapoptotic leading compound for developing novel anticancer drugs.

KEYWORDS

5,6-dihydroxy-3,7,4′-trimethoxyflavonol; G2/M arrest; Keywords; apoptosis; hepatocellular carcinoma

Title

5,6-Dihydroxy-3,7,4'-trimethoxyflavonol induces G2/M cell cycle arrest and apoptosis in human hepatocellular carcinoma cells.

Author

Zhao XX1, Chang JJ1, Wang QL1, Lu R1, Li LJ1, Sun X1, Xie WD1, Li X1,2.

Publish date

2016 Nov