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Merck
CN

02187

Isoorientin

≥98.0% (HPLC)

Synonym(s):

Homoorientin, Luteolin 6-C-β-D-glucoside, Luteolin 6-C-glucoside

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About This Item

Empirical Formula (Hill Notation):
C21H20O11
CAS Number:
4261-42-1
Molecular Weight:
448.38
UNSPSC Code:
12352201
PubChem Substance ID:
329747399
MDL number:
MFCD00017433

Key Documents

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InChI

1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)c2c(O)cc3OC(=CC(=O)c3c2O)c4ccc(O)c(O)c4

InChI key

ODBRNZZJSYPIDI-VJXVFPJBSA-N

assay

≥98.0% (HPLC)

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Biochem/physiol Actions

C-glycosyl flavone with anti-inflammatory, antimicrobial and antioxidant properties. Induces antioxidant response through PI3K singaling.
Luteolin, a common flavonoid, has been shown to inhibit secretion of ET-1 by porcine aortic endothelial cells at a 10 uM concentration. However, the luteolin glycoside compound, luteolin 6-C-glucoside, showed very weak inhibition of ET-1 release and inhibition only occurred at higher concentrations of luteolin 6-C-glucoside.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBQ4981V
BCBP9553V
BCBP2245V
BCBM6958V
BCBK3045V

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Luteolin inhibits endothelin-1 secretion in cultured endothelial cells.
Kozakai, T.
Biosciences, Biotechnology Research Asia, 69, 1613-1615 (2005)
Jinyong Peng et al.
Journal of chromatography. A, 1074(1-2), 111-115 (2005-06-09)
High-speed counter-current chromatography (HSCCC) with a solvent system composed of ethyl acetate-n-butanol-water (2:1:3, v/v/v) was used to isolate and separate two C-glycosylflavones from Patrinia villosa Juss, a traditional Chinese medicine. The separation produced 42.9 mg isovitexin and 20.1 mg isoorientin
Roxana Orrego et al.
Molecules (Basel, Switzerland), 14(10), 3906-3913 (2009-11-20)
This study assessed the inhibitory effect of three C-glycosylflavonoids from Cymbopogon citratus leaves--isoorientin (1), swertiajaponin (2) and isoorientin 2"-Orhamnoside (3)--on human LDL oxidation. Isolated LDL was incubated with compounds 1-3 and the kinetics of lipid peroxidation were assessed by conjugated
Li Yuan et al.
Toxicology and applied pharmacology, 265(1), 83-92 (2012-10-03)
Isoorientin (ISO) is a flavonoid compound that can be extracted from several plant species, such as Phyllostachys pubescens, Patrinia, and Drosophyllum lusitanicum; however, its biological activity remains poorly understood. The present study investigated the effects and putative mechanism of apoptosis
Severina Pacifico et al.
Journal of natural products, 73(12), 1973-1978 (2010-11-18)
Eight flavonoid C-glycosides, including three new analogues, have been isolated from leaf and root methanolic extracts of Petrorhagia velutina, a Mediterranean herbaceous plant. The antiproliferative activity against human hepatoblastoma cancer cell line HepG2 has been analyzed by the MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium
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