Psoralidin

Names

[ Name ]:
Psoralidin

[Synonym ]:
6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-2-(3-methyl-2-buten-1-yl)-
Psoralidin
3,9-dihydroxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one
3,9-Dihydroxy-2-prenylcoumestan
3,9-Dihydroxy-2-(3-methyl-2-buten-1-yl)-6H-[1]benzofuro[3,2-c]chromen-6-one
3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one
6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-2-(3-methyl-2-butenyl)-
3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro(3,2-c)(1)benzopyran-6-one
6-(3-Methylbut-2-enyl)coumestrol
3,9-Dihydroxy-2-(3-methylbut-2-en-1-yl)-6H-[1]benzofuro[3,2-c]chromen-6-one

Biological Activity

[Description]:

Psoralidin, a natural furanocoumarin, is isolated from Psoralea corylifolia L. possessing anti-cancer properties.IC50 value:Target: Anticancer natural compoundin vitro: PSO dramatically decreased the cell viabilities in dose- and time-dependent manner. Autophagy inhibitor 3-MA blocked the production of LC3-II and reduced the cytotoxicity in response to PSO. Furthermore, PSO increased intracellular ROS level which was correlated to the elevation of LC3-II [1]. Psoralidin at 10 μM was able to induce the maximum reporter gene expression corresponding to that of E2-treated cells and such activation of the ERE-reporter gene by psoralidin was completely abolished by the cotreatment of a pure ER antagonist, implying that the biological activities of psoralidin are mediated by ER [2]. Psoralidin enhanced TRAIL-induced apoptosis in HeLa cells through increased expression of TRAIL-R2 death receptor and depolarization of mitochondrial membrane potential [3]. Psoralidin inhibited the IR-induced COX-2 expression and PGE(2) production through regulation of PI3K/Akt and NF-κB pathway. Also, psoralidin blocked IR-induced LTB(4) production, and it was due to direct interaction of psoralidin and 5-lipoxygenase activating protein (FLAP) in 5-LOX pathway. IR-induced fibroblast migration was notably attenuated in the presence of psoralidin [4].in vivo: Moreover, in vivo results from mouse lung indicate that psoralidin suppresses IR-induced expression of pro-inflammatory cytokines (TNF-α, TGF-β, IL-6 and IL-1 α/β) and ICAM-1[4].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> Notch

Natural Products >> Phenylpropanoids

Research Areas >> Cancer

[References]

[1]. Hao W, et al. Psoralidin induces autophagy through ROS generation which inhibits the proliferation of human lung cancer A549 cells. PeerJ. 2014 Sep 9;2:e555.

[2]. Liu X, et al. Psoralidin, a coumestan analogue, as a novel potent estrogen receptor signaling molecule isolated from Psoralea corylifolia. Bioorg Med Chem Lett. 2014 Mar 1;24(5):1403-6.

[3]. Bronikowska J, et al. The coumarin psoralidin enhances anticancer effect of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL). Molecules. 2012 May 29;17(6):6449-64.

[4]. Yang HJ, et al. Psoralidin, a dual inhibitor of COX-2 and 5-LOX, regulates ionizing radiation (IR)-induced pulmonary inflammation. Biochem Pharmacol. 2011 Sep 1;82(5):524-34.

[Related Small Molecules]

RO4929097 | Crenigacestat(LY3039478) | YO-01027 | LY-411575 | Tangeretin | FLI-06 | Avagacestat | IMR-1 | BMS-983970 | Semagacestat(LY450139) | Z-Ile-Leu-aldehyde | tCFA15

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
458.8±34.0 °C at 760 mmHg

[ Melting Point ]:
290-292°

[ Molecular Formula ]:
C₂₀H₁₆O₅

[ Molecular Weight ]:
336.338

[ Flash Point ]:
231.3±25.7 °C

[ Exact Mass ]:
336.099762

[ PSA ]:
83.81000

[ LogP ]:
5.03

[ Appearance of Characters ]:
white to beige

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.689

[ Storage condition ]:
?20°C

[ Water Solubility ]:
DMSO: soluble5mg/mL, clear (warmed)

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

[Study on effect of psoralidin on anti-experimental postmenopausal osteoporosis and its mechanism].

Zhongguo Zhong Yao Za Zhi 38(11) , 1816-9, (2013)

To observe the effect of psoralidine in rats with ovariectomy, and preliminarily study its mechanism.Sixty female Sprague-Dawley rats were divided into 5 groups: the sham operation group, the model gr...

[Study on the chemical constituents of Psoralea corylifolia].

Zhong Yao Cai 34(8) , 1211-3, (2011)

To study the chemical constituents of Psoralea corylifolia.Column chromatography was used in the isolation procedure. The structures of isolated compounds were elucidated by spectral data.Seven compou...

Psoralidin, a dual inhibitor of COX-2 and 5-LOX, regulates ionizing radiation (IR)-induced pulmonary inflammation.

Biochem. Pharmacol. 82(5) , 524-34, (2011)

Radiotherapy is the most significant non-surgical cure for the elimination of tumor, however it is restricted by two major problems: radioresistance and normal tissue damage. Efficiency improvement on...