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Bavachinin A

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-B2005

  • Specification : 98%

  • CAS number : 19879-30-2

  • Formula : C21H22O4

  • Molecular Weight : 338.4

  • PUBCHEM ID : 10337211

  • Volume : 20mg

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Catalogue Number

BF-B2005

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

338.4

Appearance

Yellow crystalline powder

Botanical Source

Cullen corylifolium

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=CCC1=CC2=C(C=C1OC)OC(CC2=O)C3=CC=C(C=C3)O)C

Synonyms

2-(4-Hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-2,3-dihydro-4H-chromen-4-one/2-(4-Hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-2,3-dihydro-4H-chromen-4-on/2-(4-Hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one/2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydro-4H-chromen-4-one/Bavachinin/4H-1-Benzopyran-4-one, 2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-/2-(4-Hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-2,3-dihydro-4H-chromen-4-one/7-O-Methylbavachin/4'-Hydroxy-7-methoxy-6-(3-methyl-2-butenyl)flavanone/Bavachinin A

IUPAC Name

(2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

Density

1.2±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate

Flash Point

190.3±23.6 °C

Boiling Point

537.1±50.0 °C at 760 mmHg

Melting Point

139-145ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2942000000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:19879-30-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31322235

Abstract

Bavachinin (BNN), one of the main active ingredients of Psoraleacorylifolia, can activate peroxisome proliferator‑activated receptor γ (PPARγ). PPARγ has become a promising therapeutic target in cancer. The aim of the present study was to explore the antitumor effects of BNN in non‑small cell lung cancer (NSCLC). Cell Counting Kit‑8 and lactate dehydrogenase release assays were performed to measure cell toxicity. Western blotting and immunofluorescence were used to analyze the expression of apoptosis‑related factors and PPARγ. The ability of PPARγ to bind to BNN was evaluated by drug affinity responsive target stability (DARTS) and cellular thermal shift assay (CETSA). A reactive oxygen species (ROS) assay kit was used to detect the ROS level. The results revealed that the survival rates and cell viability of A549 cells were reduced by BNN in a dose‑dependent manner. The present results also demonstrated that BNN dose‑dependently changed the expression of Bcl‑2, Bax, caspases‑3/9 and PPARγ. In addition, through the cytotoxic and anti‑proliferative effects, the apoptosis‑related proteins’ inhibitive properties of BNN were completely inhibited by the PPARγ antagonists T0070907 and GW9662. The DARTS and CETSA results confirmed the protein binding activity of PPARγ. Furthermore, it was demonstrated that the BNN‑induced ROS generation was dependent on PPARγ activation. Taken together, the present study demonstrated that BNN induced the death of A549 cells by activating PPARγ, an effect mediated by the increased ROS level. These results highlighted the potential role of BNN as a chemotherapeutic agent against NSCLC.

Title

Bavachinin exhibits antitumor activity against non‑small cell lung cancer by targeting PPARγ.

Author

Ge LN1, Yan L2, Li C2, Cheng K2.

Publish date

2019 Sep

PMID

30041726

Abstract

T helper type 2 (Th2) cytokines, such as interleukin (IL)-4, IL-5, and IL-13, are the central therapeutic targets in the development of drugs against asthma. Recently, it was found that bavachinin, an essential small molecule in Psoralea corylifolia, has very efficient therapeutic function in asthma treatment in a murine model via the selective inhibition of Th2 cytokine production. However, the clinical potential of bavachinin is limited by its extremely low water solubility (<30 ng/mL). Here, we fabricated a nanoparticle delivery system for the oral administration of bavachinin to treat asthma, with the aim of solving its administration problem. In this study, bavachinin-loaded PEG5000-PLGA NPs were prepared through an emulsion-solvent evaporation technique, and their physical properties were carefully characterized. These NPs showed strong enrichment capability towards inflamed lung tissues. Through oral administration, these NPs showed very good anti-asthma therapeutic effects in murine asthma model, as demonstrated by a histological analysis of lung sections, enzyme-linked immunosorbent assay (ELISA) analysis of Th2 cytokine expressions, and fluorescence-activated cell sorting (FACS) analysis of Th1/Th2 cell differentiation. This system has the potential to be used for the oral delivery of bavachinin to treat asthma and may have potential for the oral delivery of other drugs that have limited pharmacokinetic efficacy.

Title

Oral Delivery of Bavachinin-Loaded PEG-PLGA Nanoparticles for Asthma Treatment in a Murine Model.

Author

Wang K, Feng Y, Li S, Li W, Chen X, Yi R, Zhang H, Hong Z.

Publish date

2018 Oct 1

PMID

29782651

Abstract

Bavachinin (BVC), one of the main bioactive prenylated flavonoids derived from Psoralea corylifolia Linn, has a wide variety of pharmacological effects, such as antiangiogenic, antitumor, antiallergic, anti-inflammatory and antibacterial activities, especially as a pan-peroxisome proliferator-activated receptors agonist. A rapid and sensitive method for quantifying BVC in rat plasma was developed and validated through ultra-high-performance liquid chromatography coupled with electrospray-ionization tandem mass spectrometry. Furthermore, a complete metabolic investigation of BVC was performed through ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. In the pharmacokinetic analysis, BVC exhibited rapid oral absorption (Tmax = 0.68 ± 0.21 h), good elimination (T1/2 = 2.27 ± 1.63 h) following oral administration and poor absolute bioavailability (5.27%). Moreover, 11 metabolites of BVC in plasma, urine, bile and feces were characterized. The main metabolic pathways of BVC involved isomeriszation, glucuronidation, sulfonation, hydroxylation, methoxylation and reduction. In conclusion, the present study provides a sensitive quantitative method with a lower limit of quantification of 1 ng/mL and an improved comprehension of the physiological disposition of BVC.

Copyright © 2018 John Wiley & Sons, Ltd.

KEYWORDS

Liquid chromatography coupled with mass spectrometry; metabolism; pharmacokinetics; prenylated flavonoid

Title

Pharmacokinetic and metabolism studies of bavachinin through ultra-high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.

Author

Qian J1, Xie F1, Shi Y1, Li J1, Zhang L1, Li Y1, Guo F1, Wang R1.

Publish date

2018 Oct 8


Description :

Bavachinin(7-O-Methylbavachin) is a natural compound isolated from the Chinese herb Fructus Psoraleae;has potent anti-angiogenic activity.IC50 value:Target:in vitro: Isobavachalcone significantly inhibits both oligomerization and fibrillization of Aβ42, whereas bavachinin inhibits fibrillization and leads to off-pathway aggregation. Both of the compounds attenuated Aβ42-induced toxicity in a SH-SY5Y cell model [1]. Bavachinin, has potent anti-angiogenic activity in vitro and in vivo. Bavachinin inhibited increases in HIF-1α activity in human KB carcinoma (HeLa cell derivative) and human HOS osteosarcoma cells under hypoxia in a concentration-dependent manner, probably by enhancing the interaction between von Hippel-Lindau (VHL) and HIF-1α [2].in vivo: significantly inhibited Th2 cytokine production, including IL-4, IL-5 and IL-13. Notably, this compound almost completely blocked inflammation in the ovalbumin (OVA)-sensitized animal asthma model [3].