phellopterin Chemical Properties

Melting point:

102-103℃

Boiling point:

480.4±45.0 °C(Predicted)

Density 

1.243

storage temp. 

Store at -20°C

solubility 

Soluble in acetonitrile and chloroform

form 

powder

color 

Light yellow

LogP

2.867 (est)

phellopterin Usage And Synthesis

Description

Phellopterin is a commonly used yin-nourishing medicine in clinical practice. Indications: Dryness of the lungs, dry cough, fever injury, thirst and other symptoms. It is found that the preparation methods of coralline mostly use organic reagent extraction and silica gel column separation.

Uses

Phellopterin is a natural product isolated from Angelica dahurica. Phellopterin reduces TNF-alpha-induced VCAM-1 expression through regulation of the Akt and PKC pathway, which contributes to inhibit the adhesion of monocytes to endothelium[1].

Definition

ChEBI: Phellopterin is a member of psoralens.

Biological Activity

Phellopterin is a natural product isolated from P. trifoliata. It inhibits monocyte-endothelial cell adhesion by reducing TNF-alpha-induced VCAM-1 expression by regulating Akt and PKC pathways.

Synthesis

Procedure for the synthesis of Phellopterin (32): 50 mg (0.22 mmol) of compound 26 was dissolved in 2 mL of anhydrous DMF under argon protection, and 46 mg of K2CO3 and 33 μL (0.29 mmol) of 1-bromo-3-methyl-2-butene were added sequentially. The reaction mixture was heated to reflux and after 1 h of reaction, the mixture was poured into 20 mL of cold water and acidified with 1 M aqueous HCl. The product was extracted with ethyl acetate (3 x 5 mL), the organic layers were combined, and the solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by column chromatography (eluent: ethyl acetate/hexane=1:1). The fraction containing the target compound was collected, concentrated and dried to give 32 as a pale yellow powder (50 mg, 77% yield). The structure of the product was confirmed by 1H NMR, 13C NMR and HR-FABMS.1H NMR (CDCl3, 500 MHz) δ 8.12 (1H, d, J = 9.7 Hz, H-4), 7.62 (1H, d, J = 2.2 Hz, H-9), 6.99 (1H, d, J = 2.2 Hz, H-10), 6.28 (1H, d, J = 9.7 Hz, H-10), 6.28 (1H, d, J = 9.7 Hz, H-10). = 9.7 Hz, H-3), 5.61 (1H, m, H-2'), 4.85 (2H, d, J = 7.5 Hz, H-1'), 4.18 (3H, s, OCH3), 1.74 (3H, brs, H-4'), 1.70 (3H, brs, H-5'); 13C NMR (CDCl3, 125 MHz) δ 160.5 (C, C-2), 150.8 (C, C-7), 145.1 (CH, C-9), 144.4 (C, C-5 or 8a), 144.3 (C, C-5 or 8a), 139.7 (C, C-3'), 139.4 (CH, C-4), 126.9 (C, C-8), 119.8 (CH, C-2'), 114.6 (C C-6), 112.8 (CH, C-3), 107.6 (C, C-4a), 105.0 (CH, C-10), 70.4 (CH2, C-1'), 60.8 (CH3, OCH3), 25.8 (CH3, C-4'), 18.1 (CH3, C-5'); HR-FABMS (pos) m/z 301.3174 [M + H]+ (calculated value C17H17O5, 301.3156).

References

[1] Nizamutdinova IT, et al. Hesperidin, hesperidin methyl chalone and phellopterin from Poncirus trifoliata (Rutaceae) differentially regulate the expression of adhesion molecules in tumor necrosis factor-alpha-stimulated human umbilical vein endothelial cells. Int Immunopharmacol. 2008 May;8(5):670-8. DOI:10.1016/j.intimp.2008.01.011

phellopterin(2543-94-4)Related Product Information

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