toralactone Chemical Properties

Melting point:

250-252 °C

Boiling point:

480.2±45.0 °C(Predicted)

Density 

1.432±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

form 

Solid

pka

4.65±0.20(Predicted)

color 

Off-white to yellow

InChI

InChI=1S/C15H12O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h3-6,16-17H,1-2H3

InChIKey

WEHXAEGTVPWKDY-UHFFFAOYSA-N

SMILES

C1(=O)OC(C)=CC2=CC3C(C(O)=C12)=C(O)C=C(OC)C=3

CAS DataBase Reference

41743-74-2

toralactone Usage And Synthesis

Uses

Toralactone, isolated from Cassia obtusifolia, mediates hepatoprotection via an Nrf2-dependent anti-oxidative mechanism[1].

Definition

ChEBI: An organic heterotricyclic compound that is 9,10-dihydroxy-1H-benzo[g]isochromen-1-one substituted at positions 3 and 7 by methyl and methoxy groups respectively.

Synthesis

The cassia lactone was prepared as follows:

1) Take cassia seeds (seeds of Cassiaobtusifolis and Cassiatora, from Anhui Province, China) 1 kg, crushed into coarse powder, extracted with 10 liters of ethanol by heating and refluxing, and recovered solvent under reduced pressure, obtaining 210 g of extract (A). The dregs were discarded;

2) take the extract (A) 210 grams, with 1000 grams of porous resin D101, D201, D061 (Tianjin Pesticide Factory production) equal amount of mixed porous resin adsorption, first washed with 10 liters of water, and then eluted with 5 liters of ethanol, the collection of eluent, decompression recovery of solvents, to get the extract (B) 10 grams; 3) take 10 grams of the extract (B), with 1000 grams of silica gel H (manufacturer, the brand, specification) for column chromatography, using chloroform as eluent, segmented collection, TLC detection, after combining the same components, the solvent was recovered; and then recrystallized with methanol, respectively, to obtain the compound (1) (0.02g), compound (2) (2.42g), compound (3) (1.05g), compound (4) (0.5g), and compound (5) (0.32g). It is yellow needle-like crystals with a melting point of 187-189??C (methanol).

References

[1] YongtaekSeo, et al. Toralactone glycoside in Cassia obtusifolia mediates hepatoprotection via an Nrf2-dependent anti-oxidative mechanism. Food Research International. Volume 97, July 2017, Pages 340-346.
[2] Salwa D. Alqahtani, et al. Abstract 1205: Rubrofusarin and toralactone sensitize resistant MCF-7adr cell line to paclitaxel via inhibiting P-glycoprotein efflux activity. AACR Annual Meeting 2017; April 1-5, 2017; Washington, DC.

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