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    Bavachin
    Information
    CAS No. 19879-32-4 Price $90 / 20mg
    Catalog No.CFN98007Purity>=98%
    Molecular Weight324.4 Type of CompoundFlavonoids
    FormulaC20H20O4Physical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    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.
    Targets: NF-kB | p65 | IkB | VEGFR | IL Receptor | AP-1 | AMPK | PPAR | GLUT | Akt | IKK | Estrogen receptor α | Estrogen receptor β
    In vivo:
    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.[Pubmed: 27070585]
    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.[Reference: WebLink]
    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.
    Bavachin Description
    Source: The fruits of Psoralea corylifolia L.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.0826 mL 15.4131 mL 30.8261 mL 61.6523 mL 77.0654 mL
    5 mM 0.6165 mL 3.0826 mL 6.1652 mL 12.3305 mL 15.4131 mL
    10 mM 0.3083 mL 1.5413 mL 3.0826 mL 6.1652 mL 7.7065 mL
    50 mM 0.0617 mL 0.3083 mL 0.6165 mL 1.233 mL 1.5413 mL
    100 mM 0.0308 mL 0.1541 mL 0.3083 mL 0.6165 mL 0.7707 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Kinase Assay:
    Biomol Ther (Seoul). 2012 Mar;20(2):183-8.
    Activation of Estrogen Receptor by Bavachin from Psoralea corylifolia.[Pubmed: 24116293]
    In this study, we examined the estrogenic activity of Bavachin, a component of Psoralea corylifolia that has been used as a traditional medicine in Asia.
    METHODS AND RESULTS:
    Bavachin was purified from ethanolic extract of Psoralea corylifolia and characterized its estrogenic activity by ligand binding, reporter gene activation, and endogenous estrogen receptor (ER) target gene regulation. Bavachin showed ER ligand binding activity in competitive displacement of [(3)H] E2 from recombinant ER. The estrogenic activity of Bavachin was characterized in a transient transfection system using ERα or ERβ and estrogen-responsive luciferase plasmids in CV-1 cells with an EC50 of 320 nM and 680 nM, respectively. Bavachin increased the mRNA levels of estrogen-responsive genes such as pS2 and PR, and decreased the protein level of ERα by proteasomal pathway. However, Bavachin failed to activate the androgen receptor in CV-1 cells transiently transfected with the corresponding receptor and hormone responsive reporter plasmid.
    CONCLUSIONS:
    These data indicate that Bavachin acts as a weak phytoestrogen by binding and activating the ER.
    Cell Research:
    Eur J Pharmacol. 2010 Jun 25;636(1-3):181-8.
    Phytoestrogen bavachin mediates anti-inflammation targeting Ikappa B kinase-I kappaB alpha-NF-kappaB signaling pathway in chondrocytes in vitro.[Pubmed: 20361957]
    The pro-inflammatory cytokine interleukin-1 beta (IL-1 beta) plays critical roles in pathogenesis of osteoarthritis. Although estrogen is protective for cartilage in osteoarthritis patients, it also potentially increases the risk of stroke and cancer. Phytoestrogens acting as natural estrogen receptor modulators may serve as alternatives.
    METHODS AND RESULTS:
    This study aimed to identify medicinal phytoestrogens that preserve anti-inflammatory property and may function as potential chondro-protective compounds. Both human chondrocytes and chondrocytic cell line CHON-002 were used for this study. Protein concentrations or expressions were measured by ELISA or Western blot, respectively. The DNA-binding activity and transcriptional activity of transcription factors were evaluated by electrophoretic mobility shift assay and dual-luciferase reporter assay, respectively. Cell migration was analyzed by chemotaxis assays. We found that among screened phytoestrogens, Bavachin could potently decrease IL-1 beta-induced nuclear factor-kappa B (NF-kappaB) but not activator protein-1 (AP-1) DNA-binding activity. Bavachin also inhibited I kappaB alpha degradation, increased nuclear translocation of p65 and p50 as well as decreased I kappaB alpha kinase (IKK) activity. Furthermore, Bavachin inhibited IL-1 beta-induced chemokine production that resulted in reduced migration of THP-1 monocytic cells.
    CONCLUSIONS:
    Our results suggest that through decreasing IL-1 beta-induced activation of IKK-I kappaB alpha-NF-kappaB signaling pathway, Bavachin potentially protects cartilage from inflammation-mediated damage in joints of osteoarthritis patients.
    Animal Research:
    Biosci Biotechnol Biochem. 2010;74(7):1504-6.
    Inhibitory effects of bakuchiol, bavachin, and isobavachalcone isolated from Piper longum on melanin production in B16 mouse melanoma cells.[Pubmed: 20622433]

    METHODS AND RESULTS:
    An EtOH extract of fruits of Piper longum was found to exhibit a potent inhibitory effect against alpha-melanocyte-stimulating hormone (alpha-MSH)-induced melanin production in B16 mouse melanoma cells. Bioassay-directed fractionation led to the isolation of prenylated phenolic compounds bakuchiol, Bavachin, and isobavachalcone.
    CONCLUSIONS:
    These compounds and the crude extract of the fruits of P. longum may have suppressive effects against pigmentation by melanin in the skin.
    Structure Identification:
    Arch Pharm Res. 2008 Nov;31(11):1419-23.
    Bavachin and isobavachalcone, acyl-coenzyme A: cholesterol acyltransferase inhibitors from Psoralea corylifolia.[Pubmed: 19023538]
    Acyl-coenzyme A: cholesterol acyltransferase (ACAT) catalyzes cholesterol esterification and plays important roles in intestinal absorption of cholesterol, hepatic production of lipoproteins and accumulation of cholesteryl ester within macrophages and smooth muscle cells.
    METHODS AND RESULTS:
    Ethanol extract of Psoralea corylifolia showed a significant inhibition of ACAT enzyme. Via bioactivity-guided fractionation of the ethanol extract of Psoralea corylifolia, two prenylated flavonoids were isolated. Their structures were determined as Bavachin (1) and isobavachalcone (2) by spectroscopic analysis ((1)H-, (13)C-NMR, 2DNMR, and ESI-MS). The IC(50) values were 86.0 (1) and 48.0 (2) microM in the ACAT assay system using rat liver microsome. Compound 2 also decreased cholesteryl ester formations in HepG2 cells. In addition, this compound showed a noncompetitive type of inhibition of ACAT.