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Synonym name: Corylifolin
Catalogue No.: BP0239
Cas No.: 19879-32-4
Formula: C20H20O4
Mol Weight: 324.376
Botanical Source:
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:
Bavachin is a phytoestrogen that activates the estrogen receptors ERα and ERβ with EC50s of 320 and 680 nM, respectively. It is a cholesterol acyltransferase inhibitor, may have therapeutic potential for type 2 diabetes by activating insulin signaling pathways. Bavachin can stimulate the genetic expression of VEGF in PB,and directly help the fracture healing, and potentially protect cartilage from inflammation-mediated damage in joints of osteoarthritis patients through decreasing IL-1β-induced activation of IKK-IκBα-NF-κB signaling pathway. Bavachin has suppressive effects against pigmentation by melanin in the skin.
References:
Int J Mol Sci. 2016 Apr 8;17(4):527.
Bavachin from Psoralea corylifolia Improves Insulin-Dependent Glucose Uptake through Insulin Signaling and AMPK Activation in 3T3-L1 Adipocytes.
The fruit of Psoralea corylifolia L. (Fabaceae) (PC), known as "Bo-Gol-Zhee" in Korea has been used as traditional medicine. Ethanol and aqueous extracts of PC have an anti-hyperglycemic effect by increasing plasma insulin levels and decreasing blood glucose and total plasma cholesterol levels in type 2 diabetic rats.
METHODS AND RESULTS:
In this study, we purified six compounds from PC and investigated their anti-diabetic effect. Among the purified compounds, Bavachin most potently accumulated lipids during adipocyte differentiation. Intracellular lipid accumulation was measured by Oil Red-O (ORO) cell staining to investigate the effect of compounds on adipogenesis. Consistently, Bavachin activated gene expression of adipogenic transcriptional factors, proliferator-activated receptorγ (PPARγ) and CCAAT/enhancer binding protein-α (C/EBPα). Bavachin also increased adiponectin expression and secretion in adipocytes. Moreover, Bavachin increased insulin-induced glucose uptake by differentiated adipocytes and myoblasts. In differentiated adipocytes, we found that Bavachin enhanced glucose uptake via glucose transporter 4 (GLUT4) translocation by activating the Akt and 5'AMP-activated protein kinase (AMPK) pathway in the presence or absence of insulin.
CONCLUSIONS:
These results suggest that Bavachin from Psoralea corylifolia might have therapeutic potential for type 2 diabetes by activating insulin signaling pathways.
Journal of Emergency in Traditional Chinese Medicine, 2014, 23(9):1585-8.
Effect of Brain Injury and Bavachin on 5-HT and VEGF of Rats with Tibial Fracture.
To observe the influence of brain injury and Bavachin on 5-HT and VEGF during the healing of rats′ tibial fracture.
METHODS AND RESULTS:
42 healthy male SD rats were selected and randomly divided into 7groups.For normal control group,blood was drawn on the third day.For the other groups,blood was drawn on postoperative day 3,7,14,21,28,and 35.And then centrifuged supernatant was acquired to determine the amount of VEGF and 5-HT by ELISA.(1) 5-TH:The concentration in the brain injury group and facture +brain injury group peaked in the first week,before it gradually declined in the following week.It reached a plateau 3 weeks later.Comparisons between the three fracture + Bavachin groups(all three doses) and the fracture group in one and two weeks have shown no significance(P 0.05).(2)VEGF:The concentrations in all treatment groups were higher than those in the control group.The concentration in fracture + brain injury group was higher than that in fracture group or brain injury group.After a week,the concentration of VEGF was in direct proportion to those of the Bavachin in the 3 facture + Bavachin groups.5 weeks later,they headed to similar concentration.
CONCLUSIONS:
The brain injury can induce increased VEGF content in peripheral blood to promote fracture healing.Bavachin in the blood can stimulate the genetic expression of VEGF in PB,and directly help the fracture healing.Also,the high does and the middle dose have better healing efficacy.At the beginning of brain injury,5-HT increases and is released into the cerebrum capillaries,accelerating the healing of fracture.However later 5-HT goes through the blood cerebrospinal fluid barrier and its concentration in the nervous centralis declines,resulting in the slowdown of fracture healing.Bavachin has no significant influence on the 5-HT concentration during the fracture healing.
HPLC of Bavachin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
66.7600
3.6600
3.3700
High
No
No
No
No
No
No
Psoralea (Bavachin, CAS No.: 19879-32-4) is a flavonoid natural product isolated from the seeds of traditional Chinese medicine Psoralea corylifolia. As a phytoestrogen, psoralen activates estrogen receptors ERα and ERβ, showing strong estrogen-like activity. In recent years, with in-depth research into the pharmacological effects of natural products, psoralen methylene has gradually become an important research subject in the prevention and treatment of adenomas and related diseases due to its multi-target regulatory capabilities and good safety. This paper aims to systematically review the chemical structure and physicochemical properties of Psoralea-methylene, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation and pharmacokinetic characteristics, as well as its clinical application prospects and development trends, providing theoretical basis and reference for subsequent research and clinical translation.
Psoralea methylene is a flavonoid compound with a molecular formula of C20H20O5 and a molecular weight of 324.37. Its structural features include a typical flavonoid backbone, containing multiple hydroxyl and methoxy substituents, which impart strong biological activity. The LogP value of psoralen methylene is 3.66, indicating moderate lipid solubility, which facilitates cell membrane penetration and distribution in the body. The polarized surface area (TPSA) is 66.76 Ų, with 4 hydrogen bond acceptors; these physicochemical parameters support its good bioavailability and pharmacokinetic performance.
Structurally, the flavonoid core structure of psoralen methylene allows it to form stable binding with the ligand domain of estrogen receptors, activating receptor function. Its molecular weight is moderate and lacks obvious structural toxic groups, meeting the ideal characteristics of most oral small molecule drugs. Additionally, psoralen methylene has a high ability to cross the blood-brain barrier, suggesting its potential application value in central nervous system diseases.
Psoralea Methyl Extract mainly comes from Psoralea seeds. Psoralea is the dried mature seed of the leguminous plant Psoralea corylifolia, and is a commonly used herb in traditional Chinese medicine for tonifying the kidneys, enhancing yang, promoting blood circulation, and removing blood stasis. Psoralea seeds contain various active ingredients, including flavonoids, glycosides, volatile oils, and coumarins. Psoralea, as an important flavonoid component, has high levels and biological activity.
Common methods for extracting psoralen methylene include organic solvent extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) purification. Ethanol or methanol is generally used as extraction solvents, with ultrasound assisted to improve extraction efficiency. The extract undergoes steps such as concentration, separation, and silica gel column chromatography, and is finally purified by HPLC to obtain high-purity psoralen methylene. In recent years, green extraction technologies such as supercritical CO₂ extraction and microwave-assisted extraction have also been used to extract psoralen formin, significantly improving extraction efficiency and environmental friendliness.
Research on the pharmacological activity of psoralen covers multiple aspects, including anti-tumor, anti-inflammatory, antioxidant, bone metabolism regulation, and endocrine regulation. As a phytoestrogen, psoralen activates estrogen receptors ERα and ERβ, with EC50 values of 320 nM and 680 nM respectively, indicating high affinity and activation for both receptors.
Psoralein has shown inhibitory effects on tumor cell proliferation and induced apoptosis in various tumor models. Especially in adenomas and related lesions, psoralen methyl inhibits tumor growth and metastasis by regulating multiple signaling pathways. Research shows that psoralen methylene can downregulate the activity of the STAT3 signaling pathway, inhibiting tumor cell proliferation and invasion. Additionally, its regulation of targets related to cell proliferation and DNA repair, such as APP and APEX1, further enhances its anti-tumor effects.
Psoralein can significantly inhibit the production of inflammatory mediators and reduce inflammatory responses. It regulates the expression of lipoxygenases such as ALOX15 and ALOX5, reducing the formation of inflammation-related lipid mediators. At the same time, psoralen activates the NFE2L2 (Nrf2) signaling pathway, enhancing cells' antioxidant defense capacity and reducing tissue damage caused by oxidative stress.
As the main active ingredient in psoralea, psoralen methylene plays an important role in regulating bone metabolism. It activates estrogen receptors, promotes bone formation, inhibits bone resorption, and has potential anti-osteoporosis effects. Additionally, psoralen regulates SIRT1, helping to improve bone cell function and delay degenerative bone changes.
Psoralea, as a plant estrogen, can mimic the biological effects of endogenous estrogen, regulating hormone levels and receptor activity. Its effects on nuclear receptors such as NR1H4 (FXR) suggest its potential role in lipid metabolism and energy balance.
The pharmacological effects of psoralen methylene involve multiple molecular targets and signaling pathways, reflecting its multi-target and multi-pathway regulatory characteristics.
Psoralea activates receptor-mediated gene transcription by binding to ERα and ERβ, regulating cell proliferation, differentiation, and metabolism. Its different activation capacities for the two receptors may lead to selective regulatory effects in various tissues and cell types.
As a key transcription factor in various tumor and inflammation-related signaling pathways, STAT3 exerts antitumor and anti-inflammatory effects by inhibiting STAT3 phosphorylation and nuclear translocation, blocking the expression of downstream proliferative and anti-apoptotic genes.
APP plays multiple roles in cell proliferation and apoptosis. Psoranine regulates APP and may influence cell fate determination, especially in adenoma formation and progression.
Psoralein regulates the activity of ALOX15 and ALOX5, influences lipid mediator synthesis, and regulates inflammatory responses and cellular signaling.
Psoralea activates the Nrf2 signaling pathway, promotes the expression of antioxidant enzymes, enhances cells' resistance to oxidative stress, and protects tissues from oxidative damage.
As a key enzyme regulating cellular metabolism and lifespan, activation of SIRT1 helps improve cellular function and slow down the aging process. Psoralea's positive regulation of SIRT1 may be involved in bone metabolism and anti-inflammatory effects.
Psoralea also involves NR1H4 (FXR) regulation, affecting bile acid metabolism and energy homeostasis; Its effect on TYR (tyrosinase) suggests its potential applications in pigment metabolism and related diseases.
The druggability evaluation of psoralen indicates good drug development potential. Its molecular weight is 324.37, meeting the drug affinity criteria of the Lipinski rule. The LogP was 3.66, indicating moderate lipid solubility, which facilitates cell membrane penetration and distribution in vivo. TPSA was 66.76, and the number of hydrogen bond receptors was 4, both supporting good oral absorption.
In terms of toxicological evaluation, Psoralea methylene showed no hepatotoxicity, cardiotoxicity, or hERG channel inhibition. The Ames test was negative, indicating low genotoxicity risk and high safety. Additionally, its high blood-brain barrier cross-passage suggests its potential for treating central nervous system-related diseases.
Pharmacokinetic research is still in its early stages, with in vivo metabolic pathways mainly involving liver enzyme systems, and metabolites still require further identification. Key parameters such as bioavailability, half-life, and clearance rate of psoralen methylene need to be clarified through systematic in vivo and in vitro studies to provide a basis for clinical drug regimen formulation.
Psoralea, as a natural flavonoid compound with multiple biological activities, shows broad application prospects in the prevention and treatment of adenomas and related diseases. By activating estrogen receptors and regulating multiple signaling pathways, it can effectively inhibit tumor cell proliferation, reduce inflammatory responses, and improve abnormal bone metabolism, offering potential multi-target therapeutic advantages.
In the future, psoralen methylene can be developed as a candidate drug for adjunctive therapy for breast adenoma, prostate adenoma, and other hormone-related diseases. At the same time, its anti-inflammatory and antioxidant properties offer new ideas for the treatment of chronic inflammatory and degenerative diseases. Combining modern drug formulation technologies, such as nanocarriers and targeted delivery systems, is expected to improve bioavailability and targeting, enhancing therapeutic outcomes.
Additionally, the potential of psoralen methylene in central nervous system diseases is noteworthy, especially its excellent blood-brain barrier permeability offers possibilities for drug development for neurodegenerative diseases. In the future, it is necessary to strengthen pharmacokinetics, toxicology, and preclinical evaluation to promote clinical translation.
Psoralea, a natural flavonoid compound derived from psoralen, demonstrates significant pharmacological activity and good safety in the prevention and treatment of adenomas and related diseases due to its unique chemical structure and multi-target regulatory capabilities. It activates estrogen receptors and regulates key molecular targets such as STAT3, Nrf2, and SIRT1, providing a new molecular basis for the treatment of various diseases. Druggability evaluation shows that psoradelin has promising potential for drug development, and through in-depth pharmacokinetics and clinical studies, it is expected to be applied in multiple fields in the future. In summary, psoralen methylene is a candidate molecule for natural products with broad application prospects and deserves further systematic research and development.
Shenshuai
Wenjing
Hedandan
