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Key Documents

SMB01076

Sigma-Aldrich

Glycycoumarin

≥90% (LC/MS-ELSD)

Synonyme(s) :

3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)chromen-2-one

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About This Item

Formule empirique (notation de Hill):
C21H20O6
Numéro CAS:
Poids moléculaire :
368.38
Numéro MDL:
Code UNSPSC :
12352205
Nomenclature NACRES :
NA.25

Source biologique

plant

Pureté

≥90% (LC/MS-ELSD)

Forme

solid

Poids mol.

368.38

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

InChI

1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3

Clé InChI

NZYSZZDSYIBYLC-UHFFFAOYSA-N

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Description générale

Glycycoumarin, a major bioactive coumarin, is an aromatic ether and a member of resorcinols. This bioactive natural product is commonly derived from Glycyrrhiza Sp. (G. glabra, G. uralensis and G. radix) plants. Existing research suggests that this plant-derived metabolite exerts various biological activities, including anti-spasmodic, hepatoprotective, anticancer, neuroprotective, antioxidant and anti-inflammatory activities.

Application

It is a natural product derived from plant source that finds application in compound screening libraries, metabolomics, phytochemical, and pharmaceutical research.

Actions biochimiques/physiologiques

According to the existing research, Glycycoumarin serves as an estrogen agonist while also exhibiting moderate inhibitory effects on enzymes CYP1A2 and CYP2B6. Notably, Glycycoumarin demonstrates potent anti-hepatitis C virus (HCV) activity, with an IC(50) value of 8.8 µg/mL. Furthermore, it effectively inhibits smooth muscle contraction induced by various stimuli by targeting PDEs, especially isozyme 3, which leads to the accumulation of intracellular cAMP, a vital component of cellular signaling. Additionally, Glycycoumarin acts as a potent antispasmodic through the inhibition of phosphodiesterase 3, further underscoring its significance in modulating cellular responses and health. Moreover, it plays a crucial role in inhibiting hepatocyte lipoapoptosis by activating autophagy and inhibiting the ER stress/GSK-3-mediated mitochondrial pathway, showcasing its importance in cellular function.
Glycycoumarin exhibits antispasmodic activity and has a role as an antispasmodic drug and a plant metabolite. It has been demostrated to be a novel active component of licorice against non-alcoholic fatty liver disease (NAFLD).

Caractéristiques et avantages

  • High quality compound suitable for multiple research applications
  • Compatible with HPLC and mass spectrometry techniques

Autres remarques

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Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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