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Trifolirhizin

$178

  • Brand : BIOFRON

  • Catalogue Number : BF-T2018

  • Specification : 98%

  • CAS number : 6807-83-6

  • Formula : C22H22O10

  • Molecular Weight : 446.4

  • PUBCHEM ID : 442827

  • Volume : 20mg

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Catalogue Number

BF-T2018

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

446.4

Appearance

White crystal

Botanical Source

Sophora flavescens,Trifolium pratense,Picrasma quassioides,Piptanthus nepalensis,Sophora davidii

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1C2C(C3=C(O1)C=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC5=CC6=C(C=C25)OCO6

Synonyms

(6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-3-yl β-D-glucopyranoside/β-D-Glucopyranoside, (6aR,12aR)-6a,12a-dihydro-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-yl/n1959

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-yl]oxy]oxane-3,4,5-triol

Density

1.6±0.1 g/cm3

Solubility

Methanol

Flash Point

352.2±31.5 °C

Boiling Point

658.7±55.0 °C at 760 mmHg

Melting Point

142-144ºC

InChl

InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/m0/s1

InChl Key

VGSYCWGXBYZLLE-QEEQPWONSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:6807-83-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

27666116

Abstract

Trifolirhizin is a compound isolated from Sophora flavescens. It has been shown to exert cytotoxicity on several cancer cell lines. However, the underlying mechanism remains unknown. MKN45 cells were used as a research model. We assessed the cytotoxicity of trifolirhizin to MKN45 by MTT. Hoechst staining and TUNEL method were used to demonstrate apoptosis. Flow cytometry was used to determine cell cycle and ratio of apoptosis. Caspase activity assay was used to examine the activation of caspase cascade pathways. Western blotting was used to explore the protein levels. Consistently, trifolirhizin inhibited MKN45 xenograft tumor growth in vivo. Trifolirhizin caused a significantly decreased proliferation of MKN45 cells in a time- and dose-dependent manner, with IC50 values of 33.27±2.06 µg/ml at 48 h. Western blot assay manifested that trifolirhizin activated the EGFR-MAPK signaling pathways. This study indicated that trifolirhizin may be a therapeutic application in human gastric cancer therapy.

Title

Anti-proliferation effects of trifolirhizin on MKN45 cells and possible mechanism.

Author

Lu X1, Ma J2, Qiu H1, Yang L3, Cao L4, Shen J5.

Publish date

2016 Nov

PMID

31424667

Abstract

PURPOSE:
To investigate the anticancer effects of Trifolirhizin in SNU-5 human gastric cancer cells along with evaluation of its effects on autophagy, apoptosis, cell cycle phase distribution and m-TOR/PI3K signalling pathway.

METHODS:
The antiproliferative effect on gastric cancer cells was assessed by MTT assay. Autophagy was detected by electron microscopy and western blot. Apoptotic cell death was revealed by acridine orange (AO)/ethidium bromide (EB) and annexin V/propidium iodide (PI) staining using flow cytometry. Cell cycle analysis was carried out by flow cytometry. Protein expression was determined by immunoblotting. Xenografted mice models were used to evaluate in vivo the anticancer effects of Trifolirhizin.

RESULTS:
Trifolirhizin could significantly inhibit the proliferation of the gastric cancer cells. The anticancer activity of Trifolirhizin against the gastric cancer cells was found to be due to induction of autophagy and mitochondrial-mediated apoptosis. It was further observed that both apoptosis and autophagy-related protein expressions sere significantly altered. Further, it was found that Trifolirhizin could inhibit the m-TOR/PI3K/AKT signalling pathway. In vivo evaluation in xenografted mice indicated that Trifolirhizin inhibited significantly both tumor weight and tumor volume.

CONCLUSIONS:
In conclusion, it can be safely stated that Trifolirhizin has the potential to be developed as a potent anticancer agent against gastric carcinoma provided further in depth evaluation of this compound is performed.

Title

In vitro and in vivo human gastric cancer inhibition by Trifolirhizin is facilitated via autophagy, mitochondrial mediated programmed cell death, G2/M phase cell cycle arrest and inhibition of m-TOR/PI3K/AKT signalling pathway.

Author

Zhang K1, Liu W, Qu Z, Liu Q, Chen J, Tao R, Deng Y, Zhang Y.

Publish date

2019 May-Jun

PMID

25880690

Abstract

In this study, a simple, sensitive, and robust analytical method based on ultra-performance liquid chromatography (UPLC) has been developed for the determination of trifolirhizin in rat plasma using pirfenidone as internal standard (IS). After sample preparation by a simple liquid-liquid extraction, chromatography was performed on an Acquity UPLC BEH C18 column (2.1mm×50mm, 1.7μm particle size) and ultraviolet detection set at a wavelength of 366nm. The method was linear over the concentration range 25-1000ng/mL with a lower limit of quantification (LLOQ) of 25ng/mL. Inter- and intra-day precision (RSD%) were all within 10.2% and the accuracy (RE%) was equal or lower than 9.3%. The recovery was in the range of 78.5-86.4% for trifolirhizin and 87.4% for IS. Stability studies showed that trifolirhizin was stable under a variety of storage conditions. The method was successfully applied to a pharmacokinetic study involving oral administration of trifolirhizin to rats.

Copyright © 2015 Elsevier B.V. All rights reserved.

KEYWORDS

Pharmacokinetic; Rat plasma; Trifolirhizin; UPLC

Title

Determination of trifolirhizin in rat plasma by UPLC: Application to a pharmacokinetic study.

Author

Ni KH1, Wen ZD2, Huang XC2, Wang CX3, Ye TT3, Hu GX4, Zhou MT5.

Publish date

2015 May 15


Description :

Trifolirhizin is a pterocarpan flavonoid isolated from the roots of Sophora flavescens. Trifolirhizin possesses potent tyrosinase inhibitory activity with an IC50 of 506 μM[1]. Trifolirhizin exhibits potential anti-inflammatory and anticancer activities[2].