Product Name: Bavachinin
Synonym name: Bavachinin A; 7-O-Methylbavachin; 4′-Hydroxy-7-methoxy-6-prenylflavanone
Catalogue No.: BP0240
Cas No.: 19879-30-2
Formula: C₂₁H₂₂O₄
Mol Weight: 338.403
Botanical Source: 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:

Bavachinin is a novel natural pan-PPAR agonist , it shows stronger activities with PPAR-γ than with PPAR-α and PPAR-β/δ (EC50 = 0.74 μmol/l, 4.00 μmol/l and 8.07 μmol/l in 293T cells, respectively). Bavachinin possesses anti-asthma, anti-angiogenic , anti-inflammatory, antipyretic and analgesic properties, it also exhibits glucose-lowering properties without inducing weight gain and hepatotoxicity.

References:

Indian J. Exp. Biol., 1978, 16(11):1216-7.    

Antiinflamatory, antipyretic & analgesic properties of bavachinin-a flavanone isolated from seeds of Psoralea corylifolia Linn. (Babchi).   

Antiinflamatory, antipyretic & analgesic properties of Bavachinin-a flavanone isolated from seeds of Psoralea corylifolia Linn. (Babchi).    

Eur J Pharmacol. 2012 Sep 15;691(1-3):28-37.    

Anti-angiogenic and anti-tumor activity of Bavachinin by targeting hypoxia-inducible factor-1α.  

Hypoxia-inducible factor-1 (HIF-1) consists of two subunits, the HIF-1β, which is constitutively expressed, and HIF-1α, which is oxygen-responsive. HIF-1α is over-expressed in response to hypoxia, increasing transcriptional activity linked to tumor progression, angiogenesis, metastasis, and invasion. This study aimed to demonstrate that the natural compound, Bavachinin, has potent anti-angiogenic activity in vitro and in vivo. 

METHODS AND RESULTS:

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. Furthermore, Bavachinin decreased transcription of genes associated with angiogenesis and energy metabolism that are regulated by HIF-1, such as vascular endothelial growth factors (VEGF), Glut 1 and Hexokinase 2. Bavachinin also inhibited tube formation in human umbilical vein endothelial cells (HUVECs) as well as in vitro migration of KB cells. In vivo studies showed that injecting Bavachinin thrice weekly for four weeks significantly reduced tumor volume and CD31 expression in nude mice with KB xenografts. 

CONCLUSIONS:

These data indicate that Bavachinin could be used as a therapeutic agent for inhibiting tumor angiogenesis.    

HPLC of Bavachinin

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Psoralea dihydroflavone ether (Bavachinin) is a natural flavonoid compound derived from the traditional Chinese medicine Psoralea corylifolia L. In recent years, it has attracted widespread attention due to its multi-target and multifunctional pharmacological activity. As an agonist of the pan-peroxisome proliferator-activated receptor (PPAR) family, psoralene dihydroflavone methyl ether demonstrates unique advantages in regulating metabolism, inflammation, and the tumor microenvironment. Additionally, its inhibitory effect on hypoxia-inducible factor-1α (HIF-1α) endows its antitumor potential, especially its value in non-small cell lung cancer (NSCLC) is becoming increasingly prominent. This paper aims to systematically review the chemical structure, origin, pharmacological activity, mechanism of action, druggability, and clinical application prospects of psoralene dihydroflavone methyl ether, providing a theoretical basis and scientific guidance for subsequent research and development.

Chemical structure and physicochemical properties

Psoralea dihydroflavone methyl ether has the molecular formula C21H20O5, molecular weight 340.40, CAS number 19879-30-2. Its structure belongs to the dihydroflavonoid class, with a core backbone consisting of a flavonoid ring containing methoxy substituents, exhibiting high hydrophobicity (LogP about 4.15), which is beneficial for cell membrane permeability. Its topological pole surface area (TPSA) is 55.12 Ų, and it has 4 hydrogen bond acceptors, indicating certain polarity and hydrophilicity in intermolecular interactions, facilitating binding to protein targets. Psoralea dihydroflavone methyl ether has good oral bioactivity and high permeability of the blood-brain barrier, suggesting its potential role in central nervous system diseases. Its physicochemical properties showed no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition; Ames-induced mutagenic tests were negative, indicating relatively high safety.

Plant Origins and Extraction Methods

Psoralea dihydroflavone methyl ether is mainly found in the seeds and rhizomes of Psoralea corylifolia L. Psoralea, as a traditional Chinese medicinal material, has long been used to treat osteoporosis, skin diseases, and sexual dysfunction. Psoralea dihydroflavone methyl ether extraction is commonly done using organic solvent extraction methods, with common solvents including ethanol, methanol, and ethyl acetate. The general steps are: first, crush the dried psoralea seeds and extract them by reflux with 70% ethanol. After concentration, the extract is separated by silica gel column chromatography, and purified and quantified using high-performance liquid chromatography (HPLC). In recent years, ultrasound-assisted extraction and supercritical CO2 extraction technologies have also been applied to improve extraction efficiency and purity. During extraction, attention must be paid to controlling temperature and pH to prevent degradation of flavonoid compounds.

Pharmacological activity research

1. PPAR agonist activity

Psoralea dihydroflavone methyl ether, as an agonist in the PPAR family, exhibited varying degrees of activation for PPAR-α, PPAR-β/δ, and PPAR-γ, with IC50s of 21.043 μM, 12.819 μM, and 0.622 μM respectively, indicating the strongest affinity for PPAR-γ. PPARs are members of the nuclear receptor superfamily and are involved in regulating lipid metabolism, glucose metabolism, inflammatory responses, and cell proliferation. Psoralea dihydroflavone ether activates PPAR-γ, regulates adipocyte differentiation, inhibits inflammatory factor expression, and has potential anti-diabetic, anti-inflammatory, and anti-atherosclerotic effects.

2. Antitumor activity

Psoralea dihydroflavone methyl ether demonstrates significant antitumor activity by targeting PPAR-γ and RRAR-γ (Retinoic acid receptor-related orphan receptor gamma). It has the effect of inhibiting proliferation and inducing apoptosis in non-small cell lung cancer cells. Psoralea dihydroflavone methyl ether can also inhibit HIF-1α expression, block tumor cell adaptation mechanisms in hypoxic environments, suppress tumor angiogenesis, and weaken tumor growth and metastasis ability. Moreover, its anti-inflammatory and anti-angiogenic activities further enhance its anti-tumor potential.

3. Anti-inflammatory and anti-angiogenic effects

Psoralea dihydroflavone methyl ether can inhibit the release of various inflammatory mediators, such as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6), thereby reducing inflammatory responses. It downregulates the nuclear factor-κB (NF-κB) signaling pathway by activating PPAR-γ, blocking inflammatory cascades. Additionally, psoralene dihydroflavone methyl ether inhibits the proliferation and migration of vascular endothelial cells, reduces the expression of vascular endothelial growth factor (VEGF), exerts anti-angiogenesis effects, and helps suppress tumor and inflammation-related angiogenesis.

4. Benign prostatic hyperplasia and related effects

Psoralea dihydroflavone methyl ether targets benign prostatic hyperplasia (BPH) such as monoamine oxidase A (MAOA), estrogen receptor β (ESR2), DNA repair enzyme APEX1, ATP binding cassette transporter G2 (ABCG2), lipoxygenase 5 (ALOX5), transient receptor potential vanillin receptor 1 (TRPV1), topoisomerase IIα (TOP2A), estrogen receptor α (ESR1), Monoamine oxidase B (MAOB) and androgen receptor (AR) both have potential regulatory effects, suggesting that they may coordinately regulate prostate tissue proliferation and inflammation through multiple targets, showing potential for development as BPH treatments.

Mechanism of action and molecular targets

The pharmacological action of psoralea dihydroflavone methyl ether mainly depends on its activation of the nuclear receptor PPAR family. Activation of PPAR-γ not only regulates lipid and glucose metabolism but also suppresses tumor cell proliferation and apoptosis by inhibiting the expression of inflammatory factors and cyclins. Its activation of PPAR-α and PPAR-β/δ is involved in fatty acid oxidation and energy metabolism regulation. Psoralea dihydroflavone methyl ether inhibits HIF-1α expression, blocks tumor cells' adaptation to hypoxic environments, reduces angiogenesis factor secretion, and inhibits tumor angiogenesis. Its regulation of RRAR-γ further influences cell differentiation and immune responses, enhancing antitumor effects.

In benign prostatic hyperplasia, psoralen dihydroflavone methyl ether influences proliferation and apoptosis of prostate cells by regulating androgen receptor (AR) and estrogen receptor (ERs) signaling pathways. Its regulation of MAOA and MAOB may affect neurotransmitter metabolism and regulate prostate nerve function. Additionally, regulation of ALOX5 and TRPV1 helps alleviate local inflammation and pain responses.

Druggability evaluation and pharmacokinetics

Psoralea dihydroflavone methyl ether has a moderate molecular weight (340.4 Da) and a LogP value of 4.15, indicating good lipid solubility that facilitates cell membrane penetration. TPSA is 55.12 Ų; its low polarity aids oral absorption and allows the blood-brain barrier to permeate. It has 4 hydrogen bond receptors, which meets Lipinski's rule and suggests good drug compatibility. In vitro and in vivo safety evaluations showed that psoralene dihydroflavone ether showed no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition, negative Ames test, and relatively high safety.

Pharmacokinetic studies have shown that psoralene dihydroflavone methyl ether has good oral bioavailability, moderate plasma protein binding rate, and a half-life suitable for clinical administration. Its high blood-brain barrier permeability suggests its potential for treating central nervous system-related diseases. The metabolic pathway mainly involves oxidative and methylation metabolism through the hepatic cytochrome P450 enzyme system, with good safety of the metabolites.

Prospects and outlooks for clinical applications

Psoralea dihydroflavone methyl ether, as a multi-target, multifunctional natural product, has broad clinical application potential. It shows promising therapeutic prospects in metabolic diseases (such as diabetes and lipid metabolism disorders), tumors (especially non-small cell lung cancer), and benign prostatic hyperplasia. Future research should focus on:

1. Preclinical efficacy and safety evaluation: Systematic pharmacodynamic and toxicological studies in animal models are conducted to clarify therapeutic dose windows and long-term safety.
2. In-depth analysis of the mechanism of action: combining genomics and proteomics techniques, revealing its multi-target coordinated regulatory network to facilitate the formulation of precise drug strategies.
3. Drug formulation optimization: Develop oral sustained-release formulations or targeted delivery systems to improve bioavailability and targetability, reducing potential side effects.
4. Clinical trial design: Conduct early-stage clinical trials to evaluate efficacy and safety in patients with metabolic syndrome, tumors, and BPH, and promote clinical application.

In addition, Psoralea dihydroflavone methyl ether has the potential to be further explored in central nervous system diseases such as neurodegenerative disorders. Based on its excellent blood-brain barrier penetration and anti-inflammatory properties, it is expected to become a new type of neuroprotective agent.

Conclusion

Psoralea dihydroflavone methyl ether, as a natural flavonoid compound with multiple pharmacological activities, demonstrates significant anti-inflammatory, anti-tumor, and metabolic regulatory functions due to its stimulating action on the PPAR family and inhibition of HIF-1α. Its excellent druggability and safety lay a solid foundation for its development as a novel therapeutic drug. In the future, through systematic mechanistic research and clinical translation, the application of psoralene dihydroflavone methyl ether in the treatment of various diseases will be further promoted, fostering innovative development of natural product drugs and benefiting a wide range of patients.