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Asatone

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Asatone Basic information

Product Name:
Asatone
Synonyms:
  • Asatone
  • 1,4-Ethanonaphthalene-6,10(4H)-dione, 1,4a,5,8a-tetrahydro-1,5,5,7,9,9-hexamethoxy-3,8a-di-2-propen-1-yl-, (1R,4S,4aS,8aS)-rel-
  • Asatone USP/EP/BP
  • Asatone A
  • NF-κB,inhibit,Asatone,Nuclear factor-κB,Inhibitor,Nuclear factor-kappaB
  • rel-(1R,4S,4aS,8aS)-3,8a-Diallyl-1,5,5,7,9,9-hexamethoxy-1,4a,5,8a-tetrahydro-1,4-ethanonaphthalene-6,10(4H)-dione
  • Asatone, 10 mM in DMSO
CAS:
38451-63-7
MF:
C24H32O8
MW:
448.51
Mol File:
38451-63-7.mol
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Asatone Chemical Properties

Boiling point:
536.1±50.0 °C(Predicted)
Density 
1.19±0.1 g/cm3(Predicted)
storage temp. 
4°C, protect from light
solubility 
Soluble in DMSO
form 
Solid
color 
White to off-white
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Asatone Usage And Synthesis

Chemical Properties

Blocky white crystals, soluble in methanol, ethanol, DMSO and other organic solvents, derived from AsarumsieboldiiMiq.

Uses

Asatone is an active component isolated from Radix et Rhizoma Asari, with anti-inflammatory effect via activation of NF-κB and donwn regulation of p-MAPK (ERK, JNK and p38) pathways[1].

Biological Activity

Asatone, an active ingredient isolated from Asarum, has anti-inflammatory activity by activating NF-κB and downregulating p-MAPK (ERK, JNK and p38) pathways.

Synthesis

Asatone was prepared as follows: air-dried whole powdered air-dried powder (28 kg) of the whole plant of Asarum was extracted with 70% ethanol (3?? 150 L) under reflux for a total of 6 h, and then the solvent was removed under reduced pressure. The 70% ethanol extract (4360 g) was suspended in water and sequentially partitioned with light petroleum (60-90oC), CHCl3, EtOAc and n-butyl OH. The light petroleum layer (260 g) was subjected to silica gel CC elution and gradient elution with n-hexane-EtOAc (30:1 to 0:1) to give 32 fractions (P-fractions 1-32). Semi-preparative HPLC (85% MeOH in H2O) was performed on P-fraction 6 to give asatone (25 mg).

target

NF-κB

References

[1] Chang HY, et al. Asatone Prevents Acute Lung Injury by Reducing Expressions of NF-[Formula: see text]B, MAPK and Inflammatory Cytokines. Am J Chin Med. 2018;46(3):651-671. DOI:10.1142/S0192415X18500349

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