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SML0582

Sigma-Aldrich

Hispidulin

≥98% (HPLC)

Synonym(s):

4′,5,7-Trihydroxy-6-methoxyflavone, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one, 6-Methoxyapigenin, 6-Methylscutellarein, Dinatin, Salvitin, Scutellarein 6-methyl ether

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About This Item

Empirical Formula (Hill Notation):
C16H12 O6
CAS Number:
1447-88-7
Molecular Weight:
300.26
MDL number:
MFCD00143504
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

OC1=C(OC)C(O)=C(C(C=C(C2=CC=C(O)C=C2)O3)=O)C3=C1

InChI

1S/C16H12O6/c1-21-16-11(19)7-13-14(15(16)20)10(18)6-12(22-13)8-2-4-9(17)5-3-8/h2-7,17,19-20H,1H3

InChI key

IHFBPDAQLQOCBX-UHFFFAOYSA-N

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Application

Hispidulin has been used as a calibration standard:
  • in high-performance liquid chromatography (HPLC) for quantification of Clerodendrum petasites flavonoids
  • in liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) analysis
  • in reverse-phase high-performance liquid chromatography with a diode-array detector (HPLC-DAD) and high-performance thin-layer chromatography (HPTLC)

Biochem/physiol Actions

Hispidulin also exhibits antiosteoporotic anti-atheromatous, antispasmodic and anticancer functionality. It exhibits inhibition on α-glucosidase enzymatic activity. Hispidulin inhibits platelet aggregation and is more effective than theophylline. It also acts as a modulator of the γ-aminobutyric acid receptor (GABA) and blocks the release of glutamate synaptosomes associated with cortical neurons.
Hispidulin is a bioactive flavonoid with a variety of effects including antiproliferative, antifungal, anti-inflammatory, antioxidative and antiepileptic activity. Like EGCG, hispidulin appears to activate AMPK and inhibit the PI3K/Akt/mTOR pathway. The antiepileptic activity may be due to additional activity as a benzodiazepine (BZD) receptor ligand.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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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Chun-xiang Fu et al.
Applied biochemistry and biotechnology, 134(1), 89-96 (2006-08-08)
Cell cultures of Saussurea medusa produce valuable secondary metabolites, and jaceosidin and hispidulin are the major bioactive compounds. In the present study, the cultures were challenged by methyl jasmonate (MJ). The highest jaceosidin and hispidulin concentrations (65.2 +/- 3.67 mg/L
Laurie P Sutton et al.
The international journal of neuropsychopharmacology, 15(7), 965-979 (2011-07-23)
The dopamine D2 receptor (D2DR) regulates Akt and may also target the Wnt pathway, two signalling cascades that inhibit glycogen synthase kinase-3 (GSK-3). This study examined whether the Wnt pathway is regulated by D2DR and the role of Akt and
Flavonoids: some of the wisdom of sage?
G A R Johnston et al.
British journal of pharmacology, 142(5), 809-810 (2004-07-03)
Priscila Dabaghi-Barbosa et al.
Free radical research, 39(12), 1305-1315 (2005-11-22)
Hispidulin (6-methoxy-5,7,4'-trihydroxyflavone) and eupafolin (6-methoxy-5,7,3',4'-tetrahydroxyflavone), are flavonoids found in the leaves of Eupatorium litoralle. They have recognized antioxidant and antineoplastic properties, although their action mechanisms have not been previously described. We now report the effects of hispidulin on the oxidative
L D Zhou et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 26(2), 114-117 (2003-01-15)
To study the chemical constituents the roots of Chirita fimbrisepala. The constituents were extracted with solvent, separated and purified with chromatographic methods, identified by NMR, MS, UV, IR and physical-chemical constants. Three flavonoids mahuangchiside(I), hispidulin (II) and kaempferol(III) were isolated
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