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Licoisoflavone A

$1,120

  • Brand : BIOFRON

  • Catalogue Number : BD-P0197

  • Specification : 95.0%(HPLC)

  • CAS number : 66056-19-7

  • Formula : C20H18O6

  • Molecular Weight : 354.35

  • PUBCHEM ID : 5281789

  • Volume : 25mg

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Catalogue Number

BD-P0197

Analysis Method

HPLC,NMR,MS

Specification

95.0%(HPLC)

Storage

2-8°C

Molecular Weight

354.35

Appearance

Powder

Botanical Source

Structure Type

Flavonoids

Category

SMILES

CC(=CCC1=C(C=CC(=C1O)C2=COC3=CC(=CC(=C3C2=O)O)O)O)C

Synonyms

3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxychromen-4-one

IUPAC Name

3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxychromen-4-one

Applications

Development of a dual screening strategy to identify pro-angiogenic compounds from natural products: application on Tongmai Yangxin Pills PUMID/DOI:DOI:10.1039/c6ra19212b Li L, Liu N, Dai X, et al. Development of a dual screening strategy to identify pro-angiogenic compounds from natural products: application on Tongmai Yangxin Pills[J]. Rsc Advances, 2016, 6(116):115308-115316. Therapeutic angiogenesis was regarded as a potential treatment for ischemic diseases, and natural products are invaluable resources to identify novel compounds with pro-angiogenic activities. However, reliable and rapid strategies to identify pro-angiogenic compounds from natural products with high-throughput screening still need to be developed. We first established a dual-screening strategy by integrating a proliferation assay of human umbilical vein endothelial cells (HUVECs) in vitro with an angiogenesis assay of Tg (Fli1 alpha: EGFP) transgenic zebra fishes in vivo to screen pro-angiogenic compounds. The active components from natural products were further identified via high performance liquid chromatography coupled with mass spectrometry. The proposed dual-screening strategy was applied to Tongmai Yangxin Pills (TMYXPs). Four active flavonoid compounds (glyasperin A, glycycoumarin, licorisoflavan A and licoisoflavone A) from TMYXPs were identified and were found for the first time to have satisfactory bioactivities for promoting HUVECs proliferation and angiogenesis in zebra fishes. Based on these results, this dual screening strategy was established to rapidly screen and identify bioactive components from natural products; this offers a novel screening assay for compounds isolated from complex natural products. Isoflavones in Lupinus albus and Lupinus angustifolius: Quantitative determination by capillary zone electrophoresis, evolution of their concentration during plant development and effect on anthracnose causing fungus Colletotrichum lupini PUMID/DOI: Anthracnose, caused by Colletotrichum lupini is the disease that causes more damage in lupins around the world. Previously, we evaluated the relationship between alkaloid content and anthracnose tolerance in different varieties and breeding lines of L. albus. In the present work, an appropriate method to assess lupin isoflavones by Capillary Zone Electrophoresis (CZE) using berate alkaline buffer was developed. Genistin, licoisoflavone A, genistein and 2'-hydroxygenistein were detected in leaf, stem, bud and root of Lupins. We report amounts of these isoflavones in leaves of anthracnose tolerant and not tolerant L. albus and L. angustifolius at different development stages during the season 1998/99. Using two in-vitro bioassays against Colletotrichum lupini lupin isoflavones were tested. Our results show that licoisoflavone A, lupinalbin A, 2'-hydroxygenistein, licoisoflavone B, genistein and wighteone exerts from mild to strong fungitoxic activity. Indeed isoflavones, as natural protection, could play an important role in the resistance and tolerance of lupins against anthracnose. Inhibitory effects of Isoflavones in Sophora mooracrotiana on lipid peroxidation by superoxide PUMID/DOI:DOI:10.1076 / phbi.40.6.422.8447 S. Toda, Y. Shirataki. Inhibitory Effects of Isoflavones in Sophora mooracrotiana on Lipid Peroxidation by Superoxide[J]. Pharmaceutical Bulletin of Josai University, 2002, 40(6):422-424. The possible inhibitory effects were investigated for three isoflavones: sophoraisoflavone A, and licoisoflavones A and B, isolated from Sophora mooracrotiana Benth ex Baker, on lipid peroxidation by superoxide anion. They inhibited the production of lipid peroxidation each by superoxide, anion and the generation of superoxide anion by the xanthine-xanthine oxidase system. Their effects were similar to superoxide dismutase as a superoxide anion scavenger. These results demonstrate that these isoflavones have inhibitory effects on oxidative stress. Monitoring of MRP-like activity in human erythrocytes: inhibitory effect of isoflavones. PUMID/DOI:DOI:10.1006 / bcmd.2001.0459 Blood Cells Mol Dis. 2001 Sep-Oct;27(5):894-900. A method to fluorometrically monitor efflux of 2',7'-bis-(carboxypropyl)-5(6)-carboxyfluorescein (BCPCF) from human erythrocytes was developed. Genistein, daidzein, sophoraisoflavone A, and licoisoflavone A induced 50% inhibition (IC(50)) of BCPCF efflux at 15-70 microM. The IC(50) value of the most efficient isoflavone, licoisoflavone A (15-25 microM), was comparable to that of indomethacin (approximately 10 microM) and markedly lower than for probenecid (100-200 microM), both known MRP1 inhibitors. Our results indicate that the human erythrocyte is a useful cell model in screening potential MRP inhibitors, that BCPCF is a good substrate for MRP, and that some isoflavones at low concentrations inhibit MRP-mediated efflux.

Density

1.4±0.1 g/cm3

Solubility

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

Flash Point

230.9±25.0 °C

Boiling Point

635.7±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C20H18O6/c1-10(2)3-4-13-15(22)6-5-12(19(13)24)14-9-26-17-8-11(21)7-16(23)18(17)20(14)25/h3,5-9,21-24H,4H2,1-2H3

InChl Key

KCUZCRLRQVRBBV-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2914400000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:66056-19-7) 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

32018211

Abstract

Background: Cardiac hypertrophy is a prominent feature of heart remodeling, which may eventually lead to heart failure. Tongmaiyangxin (TMYX) pills are a clinically used botanical drug for treating multiple cardiovascular diseases including chronic heart failure. The aim of the current study was to identify the bioactive compounds in Tongmaiyangxin pills that attenuate cardiomyocytes hypertrophy, and to investigate the underlying mechanism of action.

Methods and results: The anti-hypertrophy effect of TMYX was validated in isoproterenol-induced cardiac hypertrophy model in C57BL/6 mice. After TMYX treatment for 2 weeks, the heart ejection fraction and fractional shortening of the mice model was increased by approximately 20% and 15%, respectively, (p < 0.05). Besides, TMYX dose-dependently reduced the cross section area of cardiomyocytes in the angiotensin-II induced hypertrophy H9c2 model (p < 0.01). Combining high content screening and liquid chromatography mass spectrometry, four compounds with anti-cardiac hypertrophy effects were identified from TMYX, which includes emodin, licoisoflavone A, licoricone and glyasperin A. Licoisoflavone A is one of the compounds with most significant protective effect and we continued to investigate the mechanism. Primary cultures of neonatal rat cardiomyocytes were treated with a hypertrophic agonist phenylephrine (PE) in the presence or absence of licoisoflavone A. After 48 h of treatment, cells were harvested and mitochondrial acetylation was analyzed by western blotting and Image analysis. Interestingly, the results suggested that the anti-hypertrophic effects of licoisoflavone A depend on the activation of the deacetylase Sirt3 (p < 0.01). Finally, we showed that licoisoflavone A-treatment was able to decrease relative ANF and BNP levels in the hypertrophic cardiac cells (p < 0.01), but not in cells co-treated with Sirt3 inhibitors (3-TYP) (p > 0.05).

Conclusion: TMYX exerts its anti-hypertrophy effect possibly through upregulating Sirt3 expression. Four compounds were identified from TMYX which may be responsible for the anti-hypertrophy effect. Among these compounds, licoisoflavone A was demonstrated to block the hypertrophic response of cardiomyocytes, which required its positive regulation on the expression of Sirt3. These results suggested that licoisoflavone A is a potential Sirt3 activator with therapeutic effect on cardiac hypertrophy.

KEYWORDS

High content screening; Hypertrophy; Sirt3; Tongmaiyangxin.

Title

High content screening identifies licoisoflavone A as a bioactive compound of Tongmaiyangxin Pills to restrain cardiomyocyte hypertrophy via activating Sirt3

Author

Rui Guo 1, Ningning Liu 2, Hao Liu 1, Junhua Zhang 3, Han Zhang 3, Yingchao Wang 1, Mirko Baruscotti 4, Lu Zhao 1, Yi Wang 5

Publish date

2020 Mar