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Isoliquiritin apioside

$672

  • Brand : BIOFRON

  • Catalogue Number : BD-P0955

  • Specification : 98.5%(HPLC&TLC)

  • CAS number : 120926-46-7

  • Formula : C26H30O13

  • Molecular Weight : 550.51

  • PUBCHEM ID : 6442433

  • Volume : 25mg

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Catalogue Number

BD-P0955

Analysis Method

HPLC,NMR,MS

Specification

98.5%(HPLC&TLC)

Storage

-20℃

Molecular Weight

550.51

Appearance

Powder

Botanical Source

Glycyrrhiza uralensis Fisch./Glycyrrhiza Radix Et Rhizoma

Structure Type

Chalcones/Dihydrochalcones

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(C(O1)OC2C(C(C(OC2OC3=CC=C(C=C3)C=CC(=O)C4=C(C=C(C=C4)O)O)CO)O)O)O)(CO)O

Synonyms

2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-[4-[[2-O-[(2S,3R,4R)-tetrahydro-3,4-dihydroxy-4-(hydroxymethyl)-2-furanyl]-β-D-glucopyranosyl]oxy]phenyl]-, (2E)-/4-[(1E)-3-(2,4-Dihydroxyphenyl)-3-oxo-1-propen-1-yl]phenyl 2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydro-2-furanyl]-β-D-glucopyranoside/Neolicuroside

IUPAC Name

(E)-3-[4-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1-(2,4-dihydroxyphenyl)prop-2-en-1-one

Applications

Evaluation of antigenotoxic activity of isoliquiritin apioside from Glycyrrhiza glabra L. PUMID/DOI:19490840 Toxicol In Vitro. 2009 Jun;23(4):680-6. Prevention of manifestation of events characteristic of carcinogenesis is being emphasized a rational strategy to combat cancer. Reactive oxygen species (ROS) play an important role in tumor initiation through oxidative damage of DNA. In search for lead molecules in cancer chemoprevention from natural products, a fraction 'Rlicca' isolated from Glycyrrhiza glabra was studied for modulatory effect against hydrogen peroxide and 4-nitroquinoline-N-oxide induced genotoxicity in Escherichiacoli PQ37 using SOS chromotest and in human peripheral blood lymphocytes using the Comet assay. The fraction 'Rlicca' at a concentration of 191 microM decreased the SOS inducing potency (SOSIP) of hydrogen peroxide (1.0mM) and NQO (20 microg/ml) by 83.72% and 68.77%, respectively. In the human blood lymphocytes, 'Rlicca' reduced the tail moment induced by hydrogen peroxide (25 microM) and NQO (5 microg/ml) by 88.04% and 76.64%, respectively, using the Comet assay. The spectroscopic data of 'Rlicca' fraction revealed it to be Isoliquiritin apioside, a chalcone oligoglycoside. This is the first report of Isoliquiritin apioside with marked potential to combat oxidative stress-induced genotoxicity.

Density

1.6±0.1 g/cm3

Solubility

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

Flash Point

301.9±27.8 °C

Boiling Point

901.0±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C26H30O13/c27-10-19-20(32)21(33)22(39-25-23(34)26(35,11-28)12-36-25)24(38-19)37-15-5-1-13(2-6-15)3-8-17(30)16-7-4-14(29)9-18(16)31/h1-9,19-25,27-29,31-35H,10-12H2/b8-3+/t19-,20-,21+,22-,23+,24-,25+,26-/m1/s1

InChl Key

VMMVZVPAYFZNBM-KVFWHIKKSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:120926-46-7) 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

30618749

Abstract

Several components isolated from Glycyrrhizae radix rhizome (GR), including glycyrrhizin, liquiritin, and liquiritigenin, have been shown to induce cancer cell death and inhibit cancer metastasis. Isoliquiritin apioside (ISLA), a component isolated from GR, has been effective for treating tetanic contraction and genotoxicity. However, the effects of ISLA on the metastasis and angiogenesis of malignant cancer cells and endothelial cells (ECs) have not been reported. In this study, we found that up to 100 μM ISLA did not affect cell proliferation but efficiently suppressed the metastatic ability of HT1080 cells, as assessed by scratch-wound migration, Transwell® migration, scratch-wound invasion, Transwell® invasion, and three-dimensional spheroid invasion. ISLA significantly decreased phorbol 12-myristate 13-acetate (PMA)-induced increases in matrix metalloproteinase (MMP) activities and suppressed PMA-induced activation of mitogen-activated protein kinase as well as NF-κB, which are involved in cancer metastasis. In addition, ILSA treatment reduced the production of pro-angiogenic factors in HT1080 cells, including MMP-9, placental growth factor, and vascular endothelial growth factor under normoxia as well as hypoxia conditions, by impairing the hypoxia-inducible factor-1α pathway. We also found that the abilities of human umbilical vein ECs to migrate across the Transwell® and to form tube-like structures were significantly reduced by ISLA treatment. Moreover, using the chorioallantoic membrane assay, vessel formation with or without vascular endothelial growth factor was significantly suppressed by ISLA. These results suggested that ISLA possesses anti-metastatic and anti-angiogenic abilities in malignant cancer cells and ECs, with no cytotoxicity. ISLA may therefore be a safe and effective lead compound to develop anti-cancer drug for limiting the spread of primary tumors to distant organs to form secondary tumors.

KEYWORDS

cancer, metastasis, angiogenesis, HT1080, isoliquiritin apioside, HIF-1α, NF-κB, MAPK

Title

Isoliquiritin Apioside Suppresses in vitro Invasiveness and Angiogenesis of Cancer Cells and Endothelial Cells

Author

Aeyung Kim and Jin Yeul Ma*

Publish date

2018;

PMID

30618749

Abstract

Several components isolated from Glycyrrhizae radix rhizome (GR), including glycyrrhizin, liquiritin, and liquiritigenin, have been shown to induce cancer cell death and inhibit cancer metastasis. Isoliquiritin apioside (ISLA), a component isolated from GR, has been effective for treating tetanic contraction and genotoxicity. However, the effects of ISLA on the metastasis and angiogenesis of malignant cancer cells and endothelial cells (ECs) have not been reported. In this study, we found that up to 100 μM ISLA did not affect cell proliferation but efficiently suppressed the metastatic ability of HT1080 cells, as assessed by scratch-wound migration, Transwell® migration, scratch-wound invasion, Transwell® invasion, and three-dimensional spheroid invasion. ISLA significantly decreased phorbol 12-myristate 13-acetate (PMA)-induced increases in matrix metalloproteinase (MMP) activities and suppressed PMA-induced activation of mitogen-activated protein kinase as well as NF-κB, which are involved in cancer metastasis. In addition, ILSA treatment reduced the production of pro-angiogenic factors in HT1080 cells, including MMP-9, placental growth factor, and vascular endothelial growth factor under normoxia as well as hypoxia conditions, by impairing the hypoxia-inducible factor-1α pathway. We also found that the abilities of human umbilical vein ECs to migrate across the Transwell® and to form tube-like structures were significantly reduced by ISLA treatment. Moreover, using the chorioallantoic membrane assay, vessel formation with or without vascular endothelial growth factor was significantly suppressed by ISLA. These results suggested that ISLA possesses anti-metastatic and anti-angiogenic abilities in malignant cancer cells and ECs, with no cytotoxicity. ISLA may therefore be a safe and effective lead compound to develop anti-cancer drug for limiting the spread of primary tumors to distant organs to form secondary tumors.

KEYWORDS

HIF-1α; HT1080; MAPK; NF-κB; angiogenesis; cancer; isoliquiritin apioside; metastasis

Title

Isoliquiritin Apioside Suppresses in vitro Invasiveness and Angiogenesis of Cancer Cells and Endothelial Cells.

Author

Kim A1, Ma JY1.

Publish date

2018 Dec 10;

PMID

23365791

Abstract

A sensitive HPLC method was developed for the quantitative determination of isoliquiritin apioside (ILA) and isoliquiritin (IL) in rat plasma. After protein precipitation with acetonitrile, chloroform was used to separate lipid-soluble impurities from the plasma samples and remove acetonitrile. A chromatography was carried out on Diamonsil C18 (150 × 4.6 mm; 5 μm) analytical column, using a mobile phase consisting of water (containing phosphoric acid 0.1%, v/v); acetonitrile (72 : 28, v/v) at a flow rate of 1.0 mL/min. The wavelength-switching technology was performed to determine ILA and IL at 360 nm and wogonoside (internal standard, IS) at 276 nm. The calibration curves of ILA and IL were fairly linear over the concentration ranges of 0.060-3.84 μg/mL (r = 0.9954) and 0.075-4.80 μg/mL (r = 0.9968), respectively. The average extract recoveries of ILA, IL, and IS were all over 80%. The precision and accuracy for all concentrations of quality controls and standards were within 15%. The lower limit of quantification (LLOQ) was 0.060 μg/mL for ILA and 0.075 μg/mL for IL. The method was used in pharmacokinetic study after an oral administration of Zhigancao extract to rats.

Title

HPLC method determination of isoliquiritin apioside and isoliquiritin in rat plasma for application in pharmacokinetic study after an oral administration of zhigancao extract.

Author

Yang YY1, Xu L, Hao SY, Li Y, Zhang ZQ.

Publish date

2012;