Synonym name:
Catalogue No.: BP0989
Cas No.: 41060-15-5
Formula: C20H18O4
Mol Weight: 322.36
Botanical Source: Erythrina sigmoidea and Psoralea corylifolia
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Description:
Neobavaisoflavone, 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.
References:
Phytomedicine. 2014 Apr 15;21(5):682-8.
Activity of three cytotoxic isoflavonoids from Erythrina excelsa and Erythrina senegalensis (neobavaisoflavone, sigmoidin H and isoneorautenol) toward multi-factorial drug resistant cancer cells.
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.
Life Sci. 2014 Jan 30;95(2):101-7.
Neobavaisoflavone sensitizes apoptosis via the inhibition of metastasis in TRAIL-resistant human glioma U373MG cells.
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.
Molecules. 2011 May 3;16(5):3701-12.
Inhibition of inflammatory mediators by neobavaisoflavone in activated RAW264.7 macrophages.
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.
HPLC of Neobavaisoflavone
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Neobavaisoflavone (CAS number: 41060-15-5) is a natural flavonoid product isolated from the seeds of traditional Chinese medicine Psoralea corylifolia. As an important member of the flavonoid family, new fructooligosaccharides have received widespread attention due to their diverse biological activities, especially in the fields of anti-inflammatory, antioxidant, and anti-tumor effects, showing significant pharmacological potential. In recent years, with the advancement of natural product pharmacology and molecular biology techniques, the mechanism of action of new flavonoids and their interactions with various molecular targets have gradually been revealed, laying a solid foundation for their development as potential drug candidate molecules. This article provides a systematic review of the chemical structure and physicochemical properties, plant sources and extraction methods, pharmacological activity, mechanism of action, pharmacological evaluation, and clinical application prospects of the novel fructooligosaccharides, aiming to provide theoretical basis and reference for related research and drug development.
The new flavonoids from Fructus Psorale belong to the flavonoid class, with a molecular formula of C20H18O5 and a molecular weight of 322.36. Its structural characteristics are a typical isoflavone skeleton, containing a 3-phenylisoflavone core and multiple hydroxyl and methoxy substituents in the molecule, endowing it with certain polarity and biological activity. According to calculations, its lipid solubility index LogP is 3.6639, indicating that it has good lipid solubility and is conducive to cell membrane penetration. The topological polar surface area (TPSA) is 70.67 Å ², indicating moderate solubility of the molecule in polar environments. The low water solubility (0.0240 mg/mL) to some extent limits its oral bioavailability, but also provides direction for the improvement of drug formulations.
The chemical stability of New Psoralen Isoflavones is good, with no significant hERG channel inhibition effect. The Ames mutagenicity test result is 0.6, indicating a low risk of genotoxicity. In addition, its blood-brain barrier permeability is low, indicating limited distribution of the compound in the central nervous system, which may reduce central nervous system related side effects.
The main source of new flavonoids in Psoralea corylifolia L. is the mature seeds of the leguminous plant Psoralea corylifolia L. Psoralea, as a traditional Chinese medicine, is widely used in the field of traditional Chinese medicine and has the effects of tonifying the kidneys, strengthening yang, dispelling wind and dampness. Its seeds contain abundant isoflavone compounds, among which the new psoralen isoflavone is one of the important active ingredients.
The common methods for extracting new flavonoids from Fructus Psorale include solvent extraction, ultrasound assisted extraction, and high-performance liquid chromatography (HPLC) separation and purification. Generally, ethanol or methanol is used as the extraction solvent, and the extraction efficiency is optimized by adjusting the solvent polarity and extraction time. Ultrasound assisted extraction can significantly improve the extraction yield and shorten the extraction time. After concentration, separation, and chromatographic separation of the extract, it is purified using HPLC or preparative liquid chromatography techniques to obtain high-purity new fructooligosaccharides.
In recent years, with the development of green extraction technology, supercritical CO2 extraction and microwave-assisted extraction have also been attempted to be applied to the extraction of new flavonoids from Fructus Psorale, aiming to improve extraction efficiency and environmental friendliness.
The new fructooligosaccharides exhibit significant anti-inflammatory activity. In vitro and in vivo studies have shown that this compound can inhibit the release of various inflammatory mediators, such as tumor necrosis factor alpha (TNF - α), interleukin-6 (IL-6), and nitric oxide (NO). Its anti-inflammatory mechanism mainly involves regulating the nuclear factor kappa B (NF - κ B) signaling pathway, inhibiting the expression of inflammation related genes, and thereby reducing the inflammatory response. In addition, new flavonoids from Fructus Psorale can also inhibit the activation and migration of inflammatory cells, reducing tissue damage.
As a natural flavonoid, New Psoralen Isoflavones have excellent free radical scavenging ability. The phenolic hydroxyl groups in its structure can effectively capture reactive oxygen species (ROS) and prevent cell damage caused by oxidative stress. Multiple in vitro antioxidant experiments have shown that the new fructooligosaccharides can significantly increase the activity of intracellular antioxidant enzymes (such as superoxide dismutase (SOD) and glutathione peroxidase (GSH Px)), reduce the generation of lipid peroxidation products, and protect cells from oxidative damage.
New flavonoids from Fructus Psorale have shown good inhibitory effects in various tumor cell lines. Research has shown that its anti-tumor activity involves multiple mechanisms such as cell cycle arrest, induction of cell apoptosis, inhibition of tumor cell migration and invasion. Especially at medium to high concentrations, new fructooligosaccharides can inhibit DNA polymerase activity, block DNA replication processes, and hinder tumor cell proliferation.
In addition, the new fructooligosaccharides also exhibit inhibitory effects on platelet aggregation, which has potential significance for the prevention of tumor associated thrombosis. Platelets play an important role in the process of tumor cell metastasis, and inhibiting platelet aggregation helps to block the blood flow spread of tumor cells.
The multi-target mechanism of action of new fructooligosaccharides is the basis for their diverse pharmacological activities. The current research reveals that its main targets include:
Through the synergistic effect of multiple targets mentioned above, the novel fructooligosaccharides can effectively regulate the tumor microenvironment, inhibit tumor growth and metastasis.
The pharmacological evaluation of new fructooligosaccharides shows that they have certain potential for drug development. Its molecular weight is moderate (322.36), meeting the basic requirements of Lipinski's rule. The LogP value of 3.66 indicates that it has good lipid solubility, which is beneficial for absorption by cell membranes. However, its lower water solubility (0.0240 mg/mL) may limit oral absorption and bioavailability, which needs to be improved through pharmaceutical means.
The low permeability of the blood-brain barrier suggests that the compound mainly acts on peripheral tissues, reducing the risk of central nervous system side effects. The hERG channel inhibition experiment showed a negative result, indicating a low risk of cardiac toxicity. The Ames test result is 0.6, indicating a low risk of genotoxicity.
In terms of pharmacokinetics, existing research is relatively limited. Preliminary in vivo experiments have shown that the absorption of new fructooligosaccharides is slow after oral administration, and their bioavailability is limited. They are mainly metabolized through the liver, and the activity and safety of metabolites need further research. In the future, systematic pharmacokinetic and toxicological evaluations are needed to guide preclinical development.
Due to its multiple pharmacological activities, especially in the fields of anti-tumor and anti-inflammatory effects, the new fructooligosaccharides have good clinical development prospects. Its ability to regulate multiple tumor related targets makes it a powerful candidate for developing novel anti-cancer drugs. In addition, its antioxidant and anti-inflammatory effects provide new ideas for the treatment of chronic inflammatory diseases, immune regulation, and age-related diseases.
However, the clinical research on new fructooligosaccharides is still in its infancy and lacks systematic clinical trial data. Future research should focus on the following aspects:
In summary, as a natural product with multiple targets and functions, the novel fructooligosaccharides have strong potential for drug development and are expected to become important candidate drugs in the field of anti-tumor and anti-inflammatory therapy in the future.
As an important flavonoid active ingredient in the seeds of Fructus Psorale, new flavonoids have become a hot topic in natural product pharmacology research due to their significant anti-inflammatory, antioxidant, and anti-tumor activities. Its multi-target mechanism of action provides a theoretical basis for the development of new multifunctional drugs. Although there are still certain challenges in pharmacokinetics and clinical application, with the support of modern medicinal chemistry and formulation technology, the new psoralen isoflavones are expected to overcome existing limitations and exert greater clinical value. Future systematic research will further promote its clinical translation and assist in the innovative development of natural product drugs.
