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Scillascillin

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Scillascillin Basic information

Product Name:
Scillascillin
Synonyms:
  • (R)-5,7-Dihydroxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclobuta[f][1,3]benzodioxol]-4-one
  • Scillascillin
  • Scylin
  • Spiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclobuta[f][1,3]benzodioxol]-4-one, 5,7-dihydroxy-, (3R)-
CAS:
52706-07-7
MF:
C17H12O6
MW:
312.27
Mol File:
52706-07-7.mol
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Scillascillin Chemical Properties

Boiling point:
607.3±55.0 °C(Predicted)
Density 
1.69 g/cm3
pka
7.11±0.20(Predicted)
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Scillascillin Usage And Synthesis

Uses

Scillascillin (compound 10) is a homoisoflavanone. Scillascillin can be isolated from S. scilloides. Scillascillin shows anticancer activity towards MCF-7 (breast cancer) and DU-145 (prostate cancer) cells with the IC50 of 9.59 and 11.32 ug/ml, respectively[1][2].

Synthesis

The dried whole herb powder of Mianzhaoer was extracted with 95% industrial ethanol for three times at room temperature for 3 d each time, and about 1,936 g of extract was obtained, which was separated by silica gel column chromatography, and 10 fragments were obtained by petroleum ether-acetone elution (Fr. 1-10), and Fr. 3 (petroleum ether-acetone 90??10) was repeatedly combined with Sephadex LH-20 (chloroform-methanol 1??1) to obtain compound 1 (323 mg), 3 (45 mg), 4 (12 mg), which was white powder. Sephadex LH-20 (chloroform-methanol 1:1) to obtain compounds 1 (323 mg), 3 (45 mg), 4 (12 mg); Compound 1: white powder, NMR data and literature reports are consistent, so the identification of Compound 1 is Mianzhaoeruin.

References

[1] Yoichiro Nishida, et al. A new homostilbene and two new homoisoflavones from the bulbs of Scilla scilloides. Chem Pharm Bull (Tokyo). 56, 7. DOI:10.1248/cpb.56.1022
[2] Chinthala Y, et al. Anticancer Active Homoisoflavone from the Underground Bulbs of Ledebouria hyderabadensis. Pharmacognosy Res. 2014;6(4):303-305. DOI:10.4103/0974-8490.138272

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