PSORALIDIN

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

Structure Search

SMILES

CC(C)=CCC1=C(O)C=C2OC(=O)C3=C(OC4=CC(O)=CC=C34)C2=C1

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19254011 | https://www.ncbi.nlm.nih.gov/pubmed/18006202 | https://www.ncbi.nlm.nih.gov/pubmed/27428458 | https://www.ncbi.nlm.nih.gov/pubmed/15678382 | https://www.ncbi.nlm.nih.gov/pubmed/24507928

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein-tyrosine phosphatase 1B 34 Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15678382	Inhibitor 8297		9.4 µM [IC50]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24507928	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: http://www.ukjpb.com/article_details.php?id=285	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cytotoxic constituents of Psoralea corylifolia.	2001 Jun	11440079
In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia.	2005 Jan	15678382
Fingerprint analysis of Psoralea corylifolia L. by HPLC and LC-MS.	2005 Jul 5	15905140
[Isolation and structure identification of a new isoflavone from Psoralea corylifolias].	2006 Jan	16683532
Bioactive constituents from Chinese natural medicines. XX. Inhibitors of antigen-induced degranulation in RBL-2H3 cells from the seeds of Psoralea corylifolia.	2007 Jan	17202711
Total synthesis of psoralidin, an anticancer natural product.	2009 Apr 3	19254011
Induction of quinone reductase activity by psoralidin isolated from Psoralea corylifolia in mouse hepa 1c1c7 cells.	2009 Jul	19641888
Psoralidin, an herbal molecule, inhibits phosphatidylinositol 3-kinase-mediated Akt signaling in androgen-independent prostate cancer cells.	2009 Mar	19223576
Isolation of antioxidants from Psoralea corylifolia fruits using high-speed counter-current chromatography guided by thin layer chromatography-antioxidant autographic assay.	2010 Aug 20	20663508
Inhibiting TNF-mediated signaling: a novel therapeutic paradigm for androgen independent prostate cancer.	2010 Feb	19851870
Psoralea corylifolia Linn.-"Kushtanashini".	2010 Jan	22228944

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

PSORALIDIN

Common Name

English

6H-BENZOFURO(3,2-C)(1)BENZOPYRAN-6-ONE, 3,9-DIHYDROXY-2-(3-METHYL-2-BUTENYL)-

Systematic Name

English

PSORALIDIN [MI]

Common Name

English

3-BENZOFURANCARBOXYLIC ACID, 2-(2,4-DIHYDROXY-5-(3-METHYL-2-BUTENYL)PHENYL)-6-HYDROXY-, .DELTA.-LACTONE

Systematic Name

English

Code System Code Type Description

FDA UNII

G16ZUQ069L