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SMB00174

Sigma-Aldrich

Cirsimaritin

≥90% (LC/MS-ELSD)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C17H14O6
CAS Number:
6601-62-3
Molecular Weight:
314.29
MDL number:
MFCD00238561
UNSPSC Code:
12352200
PubChem Substance ID:
329824840
NACRES:
NA.25

Assay

≥90% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

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

InChI key

ZIIAJIWLQUVGHB-UHFFFAOYSA-N

Related Categories

General description

Natural product derived from plant source.

Biochem/physiol Actions

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.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301,H410

Precautionary Statements

P273 - P301 + P310 + P330

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (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
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
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
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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