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SMB00174

Sigma-Aldrich

Cirsimaritin

≥90% (LC/MS-ELSD)

Synonyme(s) :

4′,5-Dihydroxy-6,7-dimethoxyflavone, Skrofulein

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About This Item

Formule empirique (notation de Hill):
C17H14O6
Numéro CAS:
6601-62-3
Poids moléculaire :
314.29
Numéro MDL:
MFCD00238561
Code UNSPSC :
12352200
ID de substance PubChem :
329824840
Nomenclature NACRES :
NA.25

Pureté

≥90% (LC/MS-ELSD)

Forme

solid

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

COc1cc2OC(=CC(=O)c2c(O)c1OC)c3ccc(O)cc3

InChI

1S/C17H14O6/c1-21-14-8-13-15(16(20)17(14)22-2)11(19)7-12(23-13)9-3-5-10(18)6-4-9/h3-8,18,20H,1-2H3

Clé InChI

ZIIAJIWLQUVGHB-UHFFFAOYSA-N

Catégories apparentées

Description générale

Natural product derived from plant source.

Actions biochimiques/physiologiques

Cirsimaritin has been shown to inhibit tumor cell growth and induce mitochondrial apoptosis in GBC-SD cells. It was proposed that cirsimaritin-induced reactive oxygen species is the trigger for ER stress and down-regulate the phosphorylation of Akt.

Pictogrammes

Skull and crossbonesEnvironment
GHS06,GHS09

Mention d'avertissement

Danger

Mentions de danger

H301,H410

Conseils de prudence

P273 - P301 + P310 + P330

Classification des risques

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Effects of cirsimaritin, a flavone isolated from Artemisia judaica, on isolated guinea-pig ileum.
S S Abdalla et al.
Planta medica, 53(4), 322-324 (1987-08-01)
J A Hasrat et al.
The Journal of pharmacy and pharmacology, 49(11), 1150-1156 (1997-12-24)
In traditional medicine Microtea debilis is used against proteinuria. In ligand-binding studies extracts of Microtea debilis have been shown to inhibit the binding of [3H]1,3-dipropyl-8-cyclopentylxanthine ([3H]DPCPX) to adenosine-A1 receptors in rat forebrain membranes. Subsequently, cirsimarin, a flavonoid, was isolated as
Jih-Pyang Wang et al.
Naunyn-Schmiedeberg's archives of pharmacology, 366(4), 307-314 (2002-09-19)
In this study, the cellular localization of the inhibitory effect of a natural flavonoid cirsimaritin against formyl-methionyl-leucyl-phenylalanine (fMLP)-induced respiratory burst in rat neutrophils was investigated. Cirsimaritin concentration-dependently inhibited the superoxide anion (O(*-)(2))generation and O(2) consumption (IC(50) 11.5+/-2.2 micro M and
Mohamed Ben Sghaier et al.
Environmental toxicology and pharmacology, 32(3), 336-348 (2011-10-19)
Fractionation of the chloroformic extracts from Teucrium ramosissimum leaves resulted in the isolation of three flavonoids: genkwanin (1), cirsimaritin (2) and 4',7-dimethoxy apigenin (4) and one sesquiterpene: β-eudesmol (3). The structures were determined using data obtained from (1)H and (13)C
Zhiwei Quan et al.
Cancer letters, 295(2), 252-259 (2010-04-03)
In this study, the anticancer effect of cirsimaritin, a natural flavonoid, against human gallbladder carcinoma cell line GBC-SD and the underlying mechanisms were investigated. Cirsimaritin inhibited the growth of tumor cells and induced mitochondrial apoptosis in GBC-SD cells. In addition
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