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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Luteolin inhibits endothelin-1 secretion in cultured endothelial cells.
Kozakai, T.
Biosciences, Biotechnology Research Asia, 69, 1613-1615 (2005)
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
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
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
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