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02187

Sigma-Aldrich

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
MDL number:
MFCD00017433
UNSPSC Code:
12352201
PubChem Substance ID:
329747399

Assay

≥98.0% (HPLC)

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

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

InChI key

ODBRNZZJSYPIDI-VJXVFPJBSA-N

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Biochem/physiol Actions

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.
C-glycosyl flavone with anti-inflammatory, antimicrobial and antioxidant properties. Induces antioxidant response through PI3K singaling.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Luteolin inhibits endothelin-1 secretion in cultured endothelial cells.
Kozakai, T.
Biosciences, Biotechnology Research Asia, 69, 1613-1615 (2005)
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
Dong-Seon Kim et al.
Planta medica, 76(7), 678-682 (2009-12-05)
We aimed to find antiallergic agents from natural sources using mast cells activated during allergic reaction. We screened over 2000 plants for blockade of histamine release and identified two of them, S. baicalenesis and P. edulis. Bioassay-guided fractionation led to
Mala Ranghoo-Sanmukhiya et al.
Phytochemical analysis : PCA, 21(6), 566-574 (2010-09-08)
Aloe tormentorii, A. purpurea and A. macra are used as multipurpose folk medicines in Réunion and Mauritius Islands and are mistaken for the introduced Aloe vera. To compare the phytochemical, antimicrobial and DNA profiles of Aloe endemic to Mauritius and
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
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