Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H16O5 |
| Molecular Weight | 336.338 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=CCC1=CC2=C(OC(=O)C3=C2OC4=C3C=CC(O)=C4)C=C1O
InChI
InChIKey=YABIJLLNNFURIJ-UHFFFAOYSA-N
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
| Molecular Formula | C20H16O5 |
| Molecular Weight | 336.338 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Psoralidin (1) was first isolated from seeds of Psoralea corylifolia Linn. It was found to be an active ingredient of many Indian and Chinese traditional herbal medicines. Psoralidin exhibits a variety of biological activities like antineoplastic, antioxidant, antibacterial, antidepressant activities. Psoralidin inhibits protein tyrosine phosphatase 1B activity. Psoralidin may act as a estrogen receptor agonist. In addition psoralidin showed potent and noncompetitive inhibition against UDP- glucuronosyltransferase (UGT) or cytochrome p450 (CYP450) enzymes.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25719303 | https://www.ncbi.nlm.nih.gov/pubmed/18006202
Curator's Comment: Psoralidin is CNS active in animals. No human data available.
Originator
Sources: Chakravarti KK, Bose AK, Siddiqui S. J Sci Ind Res. 1948;7B:24–26.
Curator's Comment: Psoralidin was first isolated from seeds of Psoralea corylifolia Linn in 1948 by Chakravarti et al. and later its structure was corrected by Khastgir et al. in 1961. reference was retrieved from https://www.ncbi.nlm.nih.gov/pubmed/19254011
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Isolation of antioxidants from Psoralea corylifolia fruits using high-speed counter-current chromatography guided by thin layer chromatography-antioxidant autographic assay. | 2010-08-20 |
|
| Inhibiting TNF-mediated signaling: a novel therapeutic paradigm for androgen independent prostate cancer. | 2010-02 |
|
| Psoralea corylifolia Linn.-"Kushtanashini". | 2010-01 |
|
| Induction of quinone reductase activity by psoralidin isolated from Psoralea corylifolia in mouse hepa 1c1c7 cells. | 2009-07 |
|
| Total synthesis of psoralidin, an anticancer natural product. | 2009-04-03 |
|
| Psoralidin, an herbal molecule, inhibits phosphatidylinositol 3-kinase-mediated Akt signaling in androgen-independent prostate cancer cells. | 2009-03 |
|
| Identification of a potent herbal molecule for the treatment of breast cancer. | 2009-01-30 |
|
| [Studies on chemical constituents from seed of Psoralea corylifolia]. | 2008-06 |
|
| Transcriptional regulation of corticotrophin releasing factor gene by furocoumarins isolated from seeds of Psoralea corylifolia. | 2008-05-23 |
|
| Antidepressant-like effects of psoralidin isolated from the seeds of Psoralea Corylifolia in the forced swimming test in mice. | 2008-02-15 |
|
| Chemical fingerprint and quantitative analysis of fructus psoraleae by high-performance liquid chromatography. | 2007-04 |
|
| Bioactive constituents from Chinese natural medicines. XX. Inhibitors of antigen-induced degranulation in RBL-2H3 cells from the seeds of Psoralea corylifolia. | 2007-01 |
|
| [Isolation and structure identification of a new isoflavone from Psoralea corylifolias]. | 2006-01 |
|
| Fingerprint analysis of Psoralea corylifolia L. by HPLC and LC-MS. | 2005-07-05 |
|
| In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia. | 2005-01 |
|
| Cytotoxic constituents of Psoralea corylifolia. | 2001-06 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: In vivo, psoralidin effectively suppressed CTPE xenografts growth, without any observable toxicity.
Unknown
Route of Administration:
Oral
A cytotoxic coumestan derivative, psoralidin was isolated from the seed of Psoralea corylifolia. The IC50 values of 1 against SNU-1 and SNU-16 carcinoma cell lines were 53 and 203 micrograms/ml, respectively, indicating cytotoxic activity against stomach carcinoma cell lines.
Psoralidin was found to be a cytotoxic 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, respectively.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
G16ZUQ069L
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| Record Status |
Validated (UNII)
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Psoralidin
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