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18 β-Glycyrrhetintic Acid

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-G2002

  • Specification : 98%

  • CAS number : 471-53-4

  • Formula : C30H46O4

  • Molecular Weight : 470.68

  • PUBCHEM ID : 10114

  • Volume : 20mg

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Catalogue Number

BF-G2002

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

470.68

Appearance

White crystalline powder

Botanical Source

Glycyrrhiza uralensis

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C

Synonyms

(3β)-3-Hydroxy-11-oxoolean-12-en-30-oic acid/Glycyrrhetinic acid/(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-Hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-2-picenecarboxylic acid/18-beta-Glycyrrhetinic acid/Arthrodont/18-β-Glycyrrhetinic Acid/glycyrrhetin/GM 1658/Uralenic acid/3β-Hydroxy-11-oxoolean-12-en-30-oic acid/18b-Glycyrrhetic acid/Biosone/Olean-12-en-30-oic acid, 3β-hydroxy-11-oxo-/18β-Glycyrrhetinic acid/STX 352/Glycyrrhetic Acid/PO 12/Olean-12-en-30-oic acid, 3-hydroxy-11-oxo-, (3β)-/3b-Hydroxy-11-oxoolean-12-en-30-oic Acid/18b-Glycyrrhetinic Acid/Glycyrrhetinate/(3b,20b)-3-Hydroxy-11-oxoolean-12-en-29-oic Acid/ENOLOXONE/enoxolone

IUPAC Name

(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid

Density

1.1±0.1 g/cm3

Solubility

Methanol; Water; DMSO

Flash Point

323.7±26.6 °C

Boiling Point

588.3±50.0 °C at 760 mmHg

Melting Point

292 - 295ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2918990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:471-53-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31894688

Title

[Effect of glycyrrhetinic acid on apoptosis of thyroid cancer cell line SW579 and its mechanism].

Author

Li FY, Chen YG, Lin DY, Bai J.

Publish date

2019 Sep

PMID

31884095

Abstract

Accumulating evidence suggests that aberrant DNA methylation and gene silencing of tumor suppressors are pervasive in gastric malignancies, supporting reactivation of tumor suppressors through DNA demethylation as a potential therapeutic opportunity. Atp4a is an important tumor suppressor gene, encoding H+, K+-ATPase, and mediating gastric acid secretion in the stomach. Using transgenic gastric cancer model K19-Wnt1/C2mE (Gan) mice, by combining the transcriptome and MeDIP (methylated DNA immunoprecipitation) sequencing, together with qRT-PCR, we showed that Atp4a was expressed at low levels in tumor tissues and multiple GC cells, while both 5-aza-CdR and 18β-glycyrrhetinic acid (GRA) pharmacological treatment triggered Atp4a activation with downregulation of DNMT1. In addition, CpG island (CGI) search showed that the CpG rich region is absent in the promoter region but present in exons 9-14 of Atp4a. Methylation specific PCR (MSP) indicated that Atp4a was fully or partly methylated in multiple GC cells. Further MassArray suggested that the demethylation in the CpG site 75, 183, 196, 262-268 might be responsible for the reactivation of Atp4a. Our research identified that GRA, a bioactive component found in abundance in Radix Glycyrrhiza, reactivated Atp4a expression and inhibited gastric tumorigenesis as a potential demethylation agent.

Copyright © 2019. Published by Elsevier Inc.

KEYWORDS

18β-glycyrrhetinic acid; Atp4a; DNA methylation; Gastric cancer

Title

Reactivation of Atp4a concomitant with intragenic DNA demethylation for cancer inhibition in a gastric cancer model.

Author

Cao D1, Zhao D1, Jia Z1, Su T2, Zhang Y1, Wu Y1, Wu M2, Tsukamoto T3, Oshima M4, Jiang J1, Cao X5.

Publish date

2020 Feb 1

PMID

31883490

Abstract

Semisynthetic 18β-glycyrrhetinic acid (GA) analogues bearing 1-en-2-cyano-3-oxo substitution on ring A have enhanced antitumor effects with reduced levels of HDAC3 and HDAC6 proteins. Aiming to inhibit both HDAC protein and activity, we developed a hybrid molecule by tethering active GA analogue methyl 2-cyano-3,11-dioxo-18β-olean-1,12-dien-30-oate (CDODA-Me) and Vorinostat (SAHA). We tested the proper hybrid approaches of GA with hydroxamic acid and turned out that GA conjugated with SAHA by a piperazine linker was the best. The conjugate (15) of CDODA-Me and SAHA linked through a piperazine group was a potent cytotoxic agent against cancer cells with apoptosis induction. Compound 15 was more effective than the simple combination of CDODA-Me and SAHA to induce apoptosis. Mechanistic studies revealed that 15 was less effective than SAHA to inhibit HDAC activity, but was more effective than CDODA-Me to decrease the levels of HDAC3 and HDAC6 proteins with upregulated levels of acetylated H3 and acetylated α-tubulin. Compound 15 represents a new HDAC3 and HDAC6 inhibitor by reducing protein levels.

Copyright © 2019. Published by Elsevier Masson SAS.

KEYWORDS

18β-glycyrrhetinic acid; Anticancer; Conjugate; HDAC

Title

A 18β-glycyrrhetinic acid conjugate with Vorinostat degrades HDAC3 and HDAC6 with improved antitumor effects.

Author

Huang M1, Xie X2, Gong P2, Wei Y1, Du H1, Xu Y1, Xu Q1, Jing Y3, Zhao L4.

Publish date

2020 Feb 15


Description :

18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhizae Radix and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties.