We Offer Worldwide Shipping
Login Wishlist

Glycycoumarin

$1,076

  • Brand : BIOFRON

  • Catalogue Number : BD-P0949

  • Specification : 98.0%(HPLC)

  • CAS number : 94805-82-0

  • Formula : C21H20O6

  • Molecular Weight : 368.38

  • PUBCHEM ID : 5317756

  • Volume : 25mg

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

BD-P0949

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

368.38

Appearance

Powder

Botanical Source

Licorice

Structure Type

Coumarins

Category

Standards;Natural Pytochemical;API

SMILES

CC(=CCC1=C(C2=C(C=C1O)OC(=O)C(=C2)C3=C(C=C(C=C3)O)O)OC)C

Synonyms

3-(2,4-Dihydroxy-phenyl)-7-hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-one/3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-buten-1-yl)-2H-chromen-2-one/glycycoumarin/2H-1-Benzopyran-2-one, 3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-buten-1-yl)-/3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)chromen-2-one

IUPAC Name

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

Applications

Glycycoumarin is a major bioactive coumarin of licorice. Glycycoumarin inhibits hepatocyte lipoapoptosis through activation of autophagy and inhibition of ER stress-mediated JNK and GSK-3-mediated mitochondrial pathway. Glycycoumarin exerts anti-liver cancer activity by directly targeting T-LAK cell-originated protein kinase [1] [2].

Density

1.3±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

232.0±25.0 °C

Boiling Point

646.9±55.0 °C at 760 mmHg

Melting Point

243.5-244.5℃

InChl

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

InChl Key

NZYSZZDSYIBYLC-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932200000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:94805-82-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30024038

Abstract

BACKGROUND AND PURPOSE:
Acetaminophen-induced acute liver injury (AILI) is the most frequent cause of acute liver failure in developed countries. Given the significant limitations associated with N-acetyl cysteine, the only antidote used to treat AILI, the development of novel therapeutic approaches that can offer a wide range of therapeutic time-windows is clearly needed. Glycycoumarin (GCM), a natural coumarin purified from liquorice, has been previously demonstrated to possess potent hepatoprotective effects. In the present study, we aimed to investigate the therapeutic potential of GCM against AILI.

EXPERIMENTAL APPROACH:
Acetaminophen (300 mg·kg-1 ) was administered to male C57BL/6 mice, with and without GCM. Serum transaminases, haematoxylin and eosin staining and Western blot were used to assess hepatic damage.

KEY RESULTS:
GCM (50 mg·kg-1 ) was highly effective against acetaminophen-induced hepatotoxicity. Moreover, GCM was superior to N-acetyl cysteine, in terms of the dosage and the therapeutic time-windows. Further mechanistic investigations revealed that the therapeutic action of GCM was not a result of inhibition of acetaminophen metabolic activation or associated with Nrf2. Instead, the protective effect of GCM appeared to be predominantly dependent on sustained activation of autophagy, which attenuated acetaminophen-induced mitochondrial oxidative stress and JNK activation.

CONCLUSIONS AND IMPLICATIONS:
Collectively, our results indicate that GCM alleviated acetaminophen-induced oxidative stress through activating autophagy, thereby protecting against AILI. Our findings suggest that GCM has potential as a novel therapeutic agent for treating AILI.

© 2018 The British Pharmacological Society.

Title

Glycycoumarin protects mice against acetaminophen-induced liver injury predominantly via activating sustained autophagy.

Author

Yan M1, Ye L1, Yin S1, Lu X1, Liu X1, Lu S1, Cui J1, Fan L2, Kaplowitz N3, Hu H1.

Publish date

2018 Oct

PMID

31840883

Abstract

Licorice, an edible and medicinal plant, has long been used to treat various diseases, including liver diseases. Glycycoumarin (GCM) is a representative coumarin compound in licorice with favorable bioavailability feature. Recent studies by us demonstrated that GCM is highly effective against alcoholic liver disease, nonalcoholic fatty liver disease, acetaminophen-induced hepatotoxicity, and liver cancer through mechanisms involved in activation of Nrf2 antioxidant system, stimulation of AMPK-mediated energy homeostasis, induction of autophagy degradation process, and inhibiting oncogenic kinase T-lymphokine-activated killer cell-originated protein kinase activity. In this review, we summarize the findings on the hepatoprotective effect of GCM, discuss the signaling pathways underlying GCM-induced protective effect on liver diseases, and propose the issues that need to be addressed to promote further development of GCM as a clinically useful hepatoprotective agent.

© 2019 John Wiley & Sons, Ltd.

KEYWORDS

AILI; ALD; NAFLD; glycycoumarin; licorice; liver cancer

Title

Protective effects of glycycoumarin on liver diseases.

Author

Zhang E1, Yin S1, Zhao S1, Zhao C1, Yan M1, Fan L2, Hu H1.

Publish date

2019 Dec 16

PMID

29543705

Abstract

Glycycoumarin (GCM) is a representative of bioactive coumarin compounds isolated from licorice, an edible and medicinal plant widely used for treating various diseases including liver diseases. The purpose of the present study is to examine the possibility of GCM as a sensitizer to improve the efficacy of BH3 mimetic ABT-737 against liver cancer. Three liver cancer cell lines (HepG2, Huh-7 and SMMC-7721) were used to evaluate the in vitro combinatory effect of ABT-737/GCM. HepG2 xenograft model was employed to assess the in vivo efficacy of ABT-737/GCM combination. Results showed that GCM was able to significantly sensitize liver cancer cells to ABT-737 in both in vitro and in vivo models. The enhanced efficacy by the combination of ABT-737 and GCM was attributed to the inactivation of T-LAK cell-originated protein kinase (TOPK)-survivin axis and inhibition of de novo lipogenesis. Our findings have identified induction of TOPK-survivin axis as a novel mechanism rendering cancer cells resistant to ABT-737. In addition, ABT-737-induced platelet toxicity was attenuated by the combination. The findings of the present study implicate that bioactive coumarin compound GCM holds great potential to be used as a novel chemo-enhancer to improve the efficacy of BH3 mimetic-based therapy.

KEYWORDS

ABT-737; BH3 mimetics; Glycycoumarin; TOPK; de novo lipogenesis; liver cancer; sensitization; survivin

Title

Glycycoumarin Sensitizes Liver Cancer Cells to ABT-737 by Targeting De Novo Lipogenesis and TOPK-Survivin Axis.

Author

Zhang E1, Yin S2, Lu X3, Ye L4, Fan L5, Hu H6.

Publish date

2018 Mar 15