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SML0932

Sigma-Aldrich

Psoralidin

≥98% (HPLC)

Sinónimos:

3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one, 3,9-Dihydroxy-2-prenylcoumestan

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About This Item

Fórmula empírica (notación de Hill):
C20H16O5
Número de CAS:
18642-23-4
Peso molecular:
336.34
MDL number:
MFCD10566617
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

CC(C)=CCC1=C(C=C(OC2=O)C(C(OC3=C4)=C2C3=CC=C4O)=C1)O

InChI

1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3

InChI key

YABIJLLNNFURIJ-UHFFFAOYSA-N

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Biochem/physiol Actions

Psoralidin is a coumestan derivative extracted from Psoralea corylifolia seeds. It exhibits anti-inflammatory property by inhibiting both cyclooxygenases-2 (COX-2) and 5-lipoxygenase (5-LOX) expression. In addition to its anti-cancer and anti-inflammatory activities, psoralidin also exhibits anti-oxidant, anti-bacterial, and anti-depressant activities. Psoralidin is implicated in the regulation of insulin signaling. It is used as a key ingredient in traditional medicines for bleeding, enuresis, pollakiuria, vitiligo, and psoriasis.
Psoralidin is a furanocoumarin natural product used in Chinese medicine. Psoralidin, a PTP1B inhibitor, has been shown to have anticancer activity with a variety of mechanisms proposed. Psoralidin induces ROS generation in androgen-independent prostate cancer cells, leading to inhibition of cell proliferation. Psoralidin has been found to downregulate NOTCH1 signaling, causing growth arrest in both breast cancer stem cells and breast cancer cells.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Ewelina Szliszka et al.
Pharmacological reports : PR, 63(1), 139-148 (2011-03-29)
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
W Mar et al.
Archives of pharmacal research, 24(3), 211-213 (2001-07-07)
A coumestan derivative, psoralidin (1) was found to be a cytotoxic principle of the seeds of Psoralea corylifolia L. (Leguminosae) with the IC50 values of 0.3 and 0.4 microg/ml against the HT-29 (colon) and MCF-7 (breast) human cancer cell lines
Raj Kumar et al.
Molecular cancer therapeutics, 9(9), 2488-2496 (2010-08-26)
Epidermal growth factor receptor (EGFR) activation is an important event that regulates mitogenic signaling, such as the Raf, mitogen-activated protein kinase (MAPK), and extracellular signal-regulated kinase 1/2 cascades. EGFR activation has been implicated in the transition of prostate cancer from
Luhua Zhao et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 821(1), 67-74 (2005-05-21)
High-performance liquid chromatography (HPLC) was developed for fingerprint analysis of Psoralea corylifolia. Liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MSn) technique was first employed to identify the components of the fingerprint. The samples were separated with an Alltima C18 column (250 mm
Wen-Fei Chiou et al.
European journal of pharmacology, 650(1), 102-109 (2010-10-19)
Psoralidin has been reported to inhibit lipopolysaccharide (LPS)-induced nitric oxide (NO) production, but the mechanisms of the action remain unclear. Thus, the impact of psoralidin on signaling pathways known to be implicated in NO synthesis was explored in LPS-activated RAW264.7
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