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Neobavaisoflavone

CAS# 41060-15-5

Neobavaisoflavone

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Chemical structure

Neobavaisoflavone

3D structure

Chemical Properties of Neobavaisoflavone

Cas No. 41060-15-5 SDF Download SDF
PubChem ID 5320053 Appearance White powder
Formula C20H18O4 M.Wt 322.4
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility DMSO : ≥ 31 mg/mL (96.17 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 7-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]chromen-4-one
SMILES CC(=CCC1=C(C=CC(=C1)C2=COC3=C(C2=O)C=CC(=C3)O)O)C
Standard InChIKey OBGPEBYHGIUFBN-UHFFFAOYSA-N
Standard InChI InChI=1S/C20H18O4/c1-12(2)3-4-14-9-13(5-8-18(14)22)17-11-24-19-10-15(21)6-7-16(19)20(17)23/h3,5-11,21-22H,4H2,1-2H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Neobavaisoflavone

1 Psoralea sp.

Biological Activity of Neobavaisoflavone

DescriptionNeobavaisoflavone, exhibits inhibitory activity against DNA polymerase and platelet aggregation, it also has striking anti-inflammatory and anti-cancer effects, Neobavaisoflavone can significantly inhibit the production of reactive oxygen species (ROS), reactive nitrogen species (RNS) and cytokines: IL-1β, IL-6, IL-12p40, IL-12p70, TNF-α in LPS+IFN-γ- or PMA- stimulated RAW264.7 macrophages.
TargetsROS | IL Receptor | TNF-α | IFN-γ | p53 | Caspase | Bcl-2/Bax | p38MAPK
In vitro

Activity of three cytotoxic isoflavonoids from Erythrina excelsa and Erythrina senegalensis (neobavaisoflavone, sigmoidin H and isoneorautenol) toward multi-factorial drug resistant cancer cells.[Pubmed: 24252341 ]

Phytomedicine. 2014 Apr 15;21(5):682-8.

Resistance of cancer cells to chemotherapy has become a worldwide concern. Naturally occuring isoflavonoids possess a variety of biological activities including anti-cancer effects. The present study was aimed at investigating the cytotoxicity and the modes of action of three naturally occuring isoflavonoids, Neobavaisoflavone (1), sigmoidin H (2) and a pterocarpan that is a special type of isoflavonoid, isoneorautenol (3) against a panel of nine cancer cell lines, including various sensitive and drug-resistant phenotypes.
METHODS AND RESULTS:
The cytotoxicity of the compounds was determined using a resazurin reduction assay, whereas the caspase-Glo assay was used to detect the activation of caspases 3/7, caspase 8 and caspase 9 in cells treated with compounds 3. Flow cytometry was used for cell cycle analysis and detection of apoptotic cells, analysis of mitochondrial membrane potential (MMP) as well as measurement of reactive oxygen species (ROS). Compounds 3 showed significant cytotoxicity toward sensitive and drug-resistant cancer cell lines. Compounds 1 and 2 were selectively active, and IC50 values below 115 μM were obtained on 6/9 and 4/9 cell lines respectively with values ranging from 42.93 μM (toward CCRF-CEM cells) to 114.64 μM [against HCT116 (p53(+/+)) cells] for 1 and 25.59 μM (toward U87MG) to 110.51 μM [against HCT116 (p53(+/+)) cells] for 2. IC50 values ranging from 2.67 μM (against MDA-MB 237BCRP cells) to 21.84 (toward U87MG) were measured for compound 3 and between 0.20 μM (toward CCRF-CEM cells) and 195.12 μM (toward CEM/ADR5000 cells) for doxorubicin as control drug. BCRP-transfected MDA-MB-231 cells, HCT116 (p53(+/+)) and U87MG.ΔEGFR cells were hypersensitive (collateral sensitive) to compound 3 as compared to their counterpart cell lines. Compound 3 induced apoptosis in CCRF-CEM cells via activation of caspases 3/7, 8 and 9 as well as the loss of MMP and increased ROS production.
CONCLUSIONS:
The cytotoxicity of the studied isoflavonoids and especially the pterocarpan 3 deserve more detailed exploration in the future to develop novel anticancer drugs against sensitive and otherwise drug-resistant phenotypes.

Neobavaisoflavone sensitizes apoptosis via the inhibition of metastasis in TRAIL-resistant human glioma U373MG cells.[Pubmed: 24231449]

Life Sci. 2014 Jan 30;95(2):101-7.

Neobavaisoflavone (NBIF), an isoflavone isolated from Psoralea corylifolia (Leguminosae), has striking anti-inflammatory and anti-cancer effects. Neobavaisoflavone inhibits the proliferation of prostate cancer in vitro and in vivo.
METHODS AND RESULTS:
In this study, we found that Neobavaisoflavone sensitizes human U373MG glioma cells to TRAIL-mediated apoptosis. Co-treatment of TRAIL and Neobavaisoflavone effectively induced Bid cleavage and activated caspases 3, 8, and 9. Importantly, DR5 expression was upregulated by Neobavaisoflavone. We also observed that the combination Neobavaisoflavone and TRAIL increased expression of BAX. We further demonstrate that Neobavaisoflavone induced TRAIL-mediated apoptosis in human glioma cells by suppressing migration and invasion, and by inhibiting anoikis resistance.
CONCLUSIONS:
Taken together, our results suggest that Neobavaisoflavone reduces the resistance of cancer cells to TRAIL and that the combination of Neobavaisoflavone and TRAIL may be a new therapeutic strategy for treating TRAIL-resistant glioma cells.

Inhibition of inflammatory mediators by neobavaisoflavone in activated RAW264.7 macrophages.[Pubmed: 21540797]

Molecules. 2011 May 3;16(5):3701-12.

Flavonoids and coumarins are the major bioactive constituents identified in Psoralea corylifolia. The active fraction isolated from fruits, seeds and roots possesses antibacterial, antioxidative and immunomodulatory properties. Neobavaisoflavone is one of the flavonoids found in Psoralea corylifolia. In the present study we investigated in vitro the anti-inflammatory activity of Neobavaisoflavone.
METHODS AND RESULTS:
Macrophages play an important role in inflammation through the release of inflammatory mediators involved in the immune response. Inappropriate and prolonged macrophage activation is largely responsible for the pathology of acute and chronic inflammatory conditions. Neobavaisoflavone significantly inhibited the production of reactive oxygen species (ROS), reactive nitrogen species (RNS) and cytokines: IL-1β, IL-6, IL-12p40, IL-12p70, TNF-α in LPS+IFN-γ- or PMA- stimulated RAW264.7 macrophages.

Protocol of Neobavaisoflavone

Kinase Assay

Neobavaisoflavone stimulates osteogenesis via p38-mediated up-regulation of transcription factors and osteoid genes expression in MC3T3-E1 cells.[Pubmed: 22397994]

Phytomedicine. 2012 Apr 15;19(6):551-61.

Neobavaisoflavone (NBIF) is an isoflavone isolated from Psoralea corylifolia L, a plant claimed to have osteogenic activity and used to treat bone fractures, osteomalacia and osteoporosis.
METHODS AND RESULTS:
The present results showed that Neobavaisoflavone concentration-dependently promoted osteogenesis in MC3T3-E1cells, demonstrated by notable enhancement of alkaline phosphatase (ALP) activity, increase of bone-specific matrix proteins expression including type I collagen (Col-I), osteocalcin (OCN) and bone sialoprotein (BSP), and formation of bone nodules. However, cell proliferation in the presence of Neobavaisoflavone was not affected. Results also demonstrated that Neobavaisoflavone up-regulated the expression of runt-related transcription factor 2 (Runx2) and Osterix (Osx), the bone-specific transcription factors participating in regulation of bone marker genes expression. Application of p38 inhibitor SB203580 repressed not only Neobavaisoflavone-induced activation of ALP, the expression of Col-I, OCN and BSP, but also the matrix proteins mineralization. Western blot analysis further revealed that Neobavaisoflavone increased the phosphorylated level of p38 concentration-dependently. Additionally, inhibition of p38 abolished the stimulatory effect of Neobavaisoflavone on the expression of Runx2 and Osx. Taken together, the osteogenic activity of Neobavaisoflavone might probably act through activation of p38-dependent signaling pathway to up-regulate the mRNA levels of Runx2 and Osx then stimulate bone matrix proteins expression.
CONCLUSIONS:
The beneficial effect of Neobavaisoflavone on mineralization demonstrated that Neobavaisoflavone represented as an active component existed in P. corylifolia and might be a potential anabolic agent to treat bone loss-associated diseases.

Cell Research

Enhanced TRAIL-mediated apoptosis in prostate cancer cells by the bioactive compounds neobavaisoflavone and psoralidin isolated from Psoralea corylifolia.[Pubmed: 21441621]

Pharmacol Rep. 2011;63(1):139-48.

Numerous compounds detected in medical plants and dietary components or supplements possess chemopreventive, antitumor and immunomodulatory properties. Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is an important endogenous anticancer factor that induces apoptosis selectively in cancer cells. However, some tumor cells are resistant to TRAIL-mediated apoptosis. Naturally occurring agents could sensitize TRAIL-resistant cancer cells and augment their apoptotic activity.
METHODS AND RESULTS:
We examined the cytotoxic and apoptotic effects of Neobavaisoflavone and psoralidin in combination with TRAIL on LNCaP prostate cancer cells. The cytotoxicity was evaluated by MTT and LDH assays. The apoptosis was detected using Annexin V-FITC by flow cytometry and fluorescence microscopy. The LNCaP cells were shown to be resistant to TRAIL-induced apoptosis. Our study demonstrated that Neobavaisoflavone and psoralidin sensitized TRAIL-resistant cells and markedly augmented TRAIL-mediated apoptosis and cytotoxicity in prostate cancer cells. Cotreatment of LNCaP cells with 100 ng/ml TRAIL and 50 μM Neobavaisoflavone or 50 μM psoralidin increased the percentage of the apoptotic cells to 77.5±0.5% or 64.4±0.5%, respectively.
CONCLUSIONS:
The data indicate the potential role of the bioactive compounds isolated from the medicinal plant Psoralea corylifolia (Neobavaisoflavone and psoralidin) in prostate cancer chemoprevention through enhancement of TRAIL-mediated apoptosis.

Neobavaisoflavone Dilution Calculator

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Preparing Stock Solutions of Neobavaisoflavone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1017 mL 15.5087 mL 31.0174 mL 62.0347 mL 77.5434 mL
5 mM 0.6203 mL 3.1017 mL 6.2035 mL 12.4069 mL 15.5087 mL
10 mM 0.3102 mL 1.5509 mL 3.1017 mL 6.2035 mL 7.7543 mL
50 mM 0.062 mL 0.3102 mL 0.6203 mL 1.2407 mL 1.5509 mL
100 mM 0.031 mL 0.1551 mL 0.3102 mL 0.6203 mL 0.7754 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Neobavaisoflavone

Neobavaisoflavone, an isoflavone isolated from Psoralea corylifolia, has striking anti-inflammatory and anti-cancer effects. IC50 value: 42.93 μM (toward CCRF-CEM cells); 114.64 μM [against HCT116 (p53(+/+)) cells] [2] Target: In vitro: In the cancer cells, neobavaisoflavone sensitizes human U373MG glioma cells to TRAIL-mediated apoptosis; upregulated DR5 expression; induced TRAIL-mediated apoptosis in human glioma cells by suppressing migration and invasion, and by inhibiting anoikis resistance [1]. In caner cell lines, neobavaisoflavone is selectively active, and IC50 values below 115 μM were obtained on 6/9 cell lines, with values ranging from 42.93 μM (toward CCRF-CEM cells) to 114.64 μM [against HCT116 (p53(+/+)) cells] [2]. In vivo:

References:
[1]. Kim YJ, et al. Neobavaisoflavone sensitizes apoptosis via the inhibition of metastasis in TRAIL-resistant human glioma U373MG cells. Life Sci. 2014 Jan 30;95(2):101-7. [2]. Kuete V, Activity of three cytotoxic isoflavonoids from Erythrina excelsa and Erythrina senegalensis (neobavaisoflavone, sigmoidin H and isoneorautenol) toward multi-factorial drug resistant cancer cells. Phytomedicine. 2014 Apr 15;21(5):682-8. [3]. Ming-Jaw Don, et al. Neobavaisoflavone stimulates osteogenesis via p38-mediated up-regulation of transcription factors and osteoid genes expression in MC3T3-E1 cells. Phytomedicine Volume 19, Issue 6, 15 April 2012, Pages 551–561

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References on Neobavaisoflavone

Enhanced TRAIL-mediated apoptosis in prostate cancer cells by the bioactive compounds neobavaisoflavone and psoralidin isolated from Psoralea corylifolia.[Pubmed:21441621]

Pharmacol Rep. 2011;63(1):139-48.

Numerous compounds detected in medical plants and dietary components or supplements possess chemopreventive, antitumor and immunomodulatory properties. Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is an important endogenous anticancer factor that induces apoptosis selectively in cancer cells. However, some tumor cells are resistant to TRAIL-mediated apoptosis. Naturally occurring agents could sensitize TRAIL-resistant cancer cells and augment their apoptotic activity.We examined the cytotoxic and apoptotic effects of Neobavaisoflavone and psoralidin in combination with TRAIL on LNCaP prostate cancer cells. The cytotoxicity was evaluated by MTT and LDH assays. The apoptosis was detected using Annexin V-FITC by flow cytometry and fluorescence microscopy. The LNCaP cells were shown to be resistant to TRAIL-induced apoptosis. Our study demonstrated that Neobavaisoflavone and psoralidin sensitized TRAIL-resistant cells and markedly augmented TRAIL-mediated apoptosis and cytotoxicity in prostate cancer cells. Cotreatment of LNCaP cells with 100 ng/ml TRAIL and 50 muM Neobavaisoflavone or 50 muM psoralidin increased the percentage of the apoptotic cells to 77.5+/-0.5% or 64.4+/-0.5%, respectively. The data indicate the potential role of the bioactive compounds isolated from the medicinal plant Psoralea corylifolia (Neobavaisoflavone and psoralidin) in prostate cancer chemoprevention through enhancement of TRAIL-mediated apoptosis.

Activity of three cytotoxic isoflavonoids from Erythrina excelsa and Erythrina senegalensis (neobavaisoflavone, sigmoidin H and isoneorautenol) toward multi-factorial drug resistant cancer cells.[Pubmed:24252341]

Phytomedicine. 2014 Apr 15;21(5):682-8.

INTRODUCTION: Resistance of cancer cells to chemotherapy has become a worldwide concern. Naturally occuring isoflavonoids possess a variety of biological activities including anti-cancer effects. The present study was aimed at investigating the cytotoxicity and the modes of action of three naturally occuring isoflavonoids, Neobavaisoflavone (1), sigmoidin H (2) and a pterocarpan that is a special type of isoflavonoid, isoneorautenol (3) against a panel of nine cancer cell lines, including various sensitive and drug-resistant phenotypes. METHODS: The cytotoxicity of the compounds was determined using a resazurin reduction assay, whereas the caspase-Glo assay was used to detect the activation of caspases 3/7, caspase 8 and caspase 9 in cells treated with compounds 3. Flow cytometry was used for cell cycle analysis and detection of apoptotic cells, analysis of mitochondrial membrane potential (MMP) as well as measurement of reactive oxygen species (ROS). RESULTS: Compounds 3 showed significant cytotoxicity toward sensitive and drug-resistant cancer cell lines. Compounds 1 and 2 were selectively active, and IC50 values below 115 muM were obtained on 6/9 and 4/9 cell lines respectively with values ranging from 42.93 muM (toward CCRF-CEM cells) to 114.64 muM [against HCT116 (p53(+/+)) cells] for 1 and 25.59 muM (toward U87MG) to 110.51 muM [against HCT116 (p53(+/+)) cells] for 2. IC50 values ranging from 2.67 muM (against MDA-MB 237BCRP cells) to 21.84 (toward U87MG) were measured for compound 3 and between 0.20 muM (toward CCRF-CEM cells) and 195.12 muM (toward CEM/ADR5000 cells) for doxorubicin as control drug. BCRP-transfected MDA-MB-231 cells, HCT116 (p53(+/+)) and U87MG.DeltaEGFR cells were hypersensitive (collateral sensitive) to compound 3 as compared to their counterpart cell lines. Compound 3 induced apoptosis in CCRF-CEM cells via activation of caspases 3/7, 8 and 9 as well as the loss of MMP and increased ROS production. CONCLUSIONS: The cytotoxicity of the studied isoflavonoids and especially the pterocarpan 3 deserve more detailed exploration in the future to develop novel anticancer drugs against sensitive and otherwise drug-resistant phenotypes.

Neobavaisoflavone sensitizes apoptosis via the inhibition of metastasis in TRAIL-resistant human glioma U373MG cells.[Pubmed:24231449]

Life Sci. 2014 Jan 30;95(2):101-7.

AIMS: Neobavaisoflavone (NBIF), an isoflavone isolated from Psoralea corylifolia (Leguminosae), has striking anti-inflammatory and anti-cancer effects. NBIF inhibits the proliferation of prostate cancer in vitro and in vivo. MAIN METHODS: Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is a key endogenous molecule that selectively induces apoptosis in cancer cells with little or no toxicity in normal cells. However, some cancer cells, including U373MG cells, are resistant to TRAIL-mediated apoptosis. We demonstrated that the cell viability, migration and invasion assay were used in U373MG glioma cells. KEY FINDINGS: In this study, we found that NBIF sensitizes human U373MG glioma cells to TRAIL-mediated apoptosis. Co-treatment of TRAIL and NBIF effectively induced Bid cleavage and activated caspases 3, 8, and 9. Importantly, DR5 expression was upregulated by NBIF. We also observed that the combination NBIF and TRAIL increased expression of BAX. We further demonstrate that NBIF induced TRAIL-mediated apoptosis in human glioma cells by suppressing migration and invasion, and by inhibiting anoikis resistance. SIGNIFICANCE: Taken together, our results suggest that NBIF reduces the resistance of cancer cells to TRAIL and that the combination of NBIF and TRAIL may be a new therapeutic strategy for treating TRAIL-resistant glioma cells.

Inhibition of inflammatory mediators by neobavaisoflavone in activated RAW264.7 macrophages.[Pubmed:21540797]

Molecules. 2011 May 3;16(5):3701-12.

Flavonoids and coumarins are the major bioactive constituents identified in Psoralea corylifolia. The active fraction isolated from fruits, seeds and roots possesses antibacterial, antioxidative and immunomodulatory properties. Neobavaisoflavone is one of the flavonoids found in Psoralea corylifolia. In the present study we investigated in vitro the anti-inflammatory activity of Neobavaisoflavone. Macrophages play an important role in inflammation through the release of inflammatory mediators involved in the immune response. Inappropriate and prolonged macrophage activation is largely responsible for the pathology of acute and chronic inflammatory conditions. Neobavaisoflavone significantly inhibited the production of reactive oxygen species (ROS), reactive nitrogen species (RNS) and cytokines: IL-1beta, IL-6, IL-12p40, IL-12p70, TNF-alpha in LPS+IFN-gamma- or PMA- stimulated RAW264.7 macrophages.

Neobavaisoflavone stimulates osteogenesis via p38-mediated up-regulation of transcription factors and osteoid genes expression in MC3T3-E1 cells.[Pubmed:22397994]

Phytomedicine. 2012 Apr 15;19(6):551-61.

Neobavaisoflavone (NBIF) is an isoflavone isolated from Psoralea corylifolia L, a plant claimed to have osteogenic activity and used to treat bone fractures, osteomalacia and osteoporosis. The present results showed that NBIF concentration-dependently promoted osteogenesis in MC3T3-E1cells, demonstrated by notable enhancement of alkaline phosphatase (ALP) activity, increase of bone-specific matrix proteins expression including type I collagen (Col-I), osteocalcin (OCN) and bone sialoprotein (BSP), and formation of bone nodules. However, cell proliferation in the presence of NBIF was not affected. Results also demonstrated that NBIF up-regulated the expression of runt-related transcription factor 2 (Runx2) and Osterix (Osx), the bone-specific transcription factors participating in regulation of bone marker genes expression. Application of p38 inhibitor SB203580 repressed not only NBIF-induced activation of ALP, the expression of Col-I, OCN and BSP, but also the matrix proteins mineralization. Western blot analysis further revealed that NBIF increased the phosphorylated level of p38 concentration-dependently. Additionally, inhibition of p38 abolished the stimulatory effect of NBIF on the expression of Runx2 and Osx. Taken together, the osteogenic activity of NBIF might probably act through activation of p38-dependent signaling pathway to up-regulate the mRNA levels of Runx2 and Osx then stimulate bone matrix proteins expression. The beneficial effect of NBIF on mineralization demonstrated that NBIF represented as an active component existed in P. corylifolia and might be a potential anabolic agent to treat bone loss-associated diseases.

Description

Neobavaisoflavone, an isoflavone isolated from Psoralea corylifolia, has striking anti-inflammatory and anti-cancer effects.

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