Psoralidin

Psoralidin
Names
	Preferred IUPAC name 3,9-Dihydroxy-2-(3-methylbut-2-en-1-yl)-6H-[1]benzofuro[3,2-c][1]benzopyran-6-one
	Other names 3,9-Dihydroxy-2-prenylcoumestan
Identifiers
CAS Number	18642-23-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8616 ;
ChemSpider	4445118;
ECHA InfoCard	100.208.688
PubChem CID	5281806;
UNII	G16ZUQ069L ;
CompTox Dashboard (EPA)	DTXSID20171903 ;
	InChI 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 Key: YABIJLLNNFURIJ-UHFFFAOYSA-N; InChI=1/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 Key: YABIJLLNNFURIJ-UHFFFAOYAK;
	SMILES OC1=CC(O2)=C(C=C1)C3=C2C(C=C(C/C=C(C)/C)C(O)=C4)=C4OC3=O;
Properties
Chemical formula	C20H16O5
Molar mass	336.343 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Psoralidin is a natural phenolic compound found in the seeds of Psoralea corylifolia.

Chemical synthesis

Psoralidin production starts with a based catalyzed condensation between phenyl acetate and acid chloride. To form the ring of psoralidin, an intramolecular cyclization occurs, finished off by a microwave assisted cross metathesis reaction.^[1]

Pharmacology

Psoralidin inhibits forskolin-induced corticotrophin releasing factor gene transcription. Recently, it has shown activity in vitro against gastric, colon, prostate, and breast cancer lines. It has the capability to inhibit protein tyrosine phosphatase 1B, a key metabolite involved in insulin signaling.^[1]

Psoralidin has shown positive results in the forced swim test, a mouse model of antidepressant activity. Psoralidin raised 5-hydroxytryptamine and 5-hydroxyindoleacetic acid levels in the brain. Dopamine levels changed as well as a result of psoralidin consumption. Stress hormones in mice such as serum corticotropin releasing factor, adrenal corticotropin releasing hormone, and corticosterone were reduced after psoralidin administration.^[2]

Structure

Structurally, psoralidin is a coumestan derivative; it has an isopentenyl group at the second carbon position of coumestrol. Psoralidin is insoluble in water, making in vivo studies difficult.^[1]

References

^ ^a ^b ^c Pahari, Pallab & Rohr, Jürgen (2009). "Total Synthesis of Psoralidin, an Anticancer Natural Product". Journal of Organic Chemistry. 74 (7): 2750–2754. doi:10.1021/jo8025884. PMC 2662043. PMID 19254011.
^ Li-Tao Yi; Yu-Cheng Li; Ying Pan; Jian-Mei Li; Qun Xu; Shi-Fu Mo; Chun-Feng Qiao; Fu-Xin Jiang; Hong-Xi Xu; Xiao-Bo Lu; Ling-Dong Kong; Hsiang-Fu Kung (February 2008). "Antidepressant-like effects of psoralidin isolated from the seeds of Psoralea Corylifolia in the forced swimming test in mice". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 32 (2): 510–519. doi:10.1016/j.pnpbp.2007.10.005. PMID 18006202.

[Pahari-1] Pahari, Pallab & Rohr, Jürgen (2009). "Total Synthesis of Psoralidin, an Anticancer Natural Product". Journal of Organic Chemistry. 74 (7): 2750–2754. doi:10.1021/jo8025884. PMC 2662043. PMID 19254011.

[2] Li-Tao Yi; Yu-Cheng Li; Ying Pan; Jian-Mei Li; Qun Xu; Shi-Fu Mo; Chun-Feng Qiao; Fu-Xin Jiang; Hong-Xi Xu; Xiao-Bo Lu; Ling-Dong Kong; Hsiang-Fu Kung (February 2008). "Antidepressant-like effects of psoralidin isolated from the seeds of Psoralea Corylifolia in the forced swimming test in mice". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 32 (2): 510–519. doi:10.1016/j.pnpbp.2007.10.005. PMID 18006202.

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