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Micheliolide

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Micheliolide Basic information

Product Name:
Micheliolide
Synonyms:
  • (3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one
  • Micheliolide
  • [3aS-(3aalpha,9alpha,9aalpha,9bbeta)]-3a,4,5,7,8,9,9a,9b-Octahydro-9-hydroxy-6,9-dimethyl-3-methylene-azuleno[4,5-b]furan-2(3H)-one
  • Micheliolide, BR
  • CS-1321
  • Micheliolide 68370-47-8
  • Mecheliolide
  • Azuleno[4,5-b]furan-2(3H)-one, 3a,4,5,7,8,9,9a,9b-octahydro-9-hydroxy-6,9-dimethyl-3-methylene-, (3aS,9R,9aS,9bS)-
CAS:
68370-47-8
MF:
C15H20O3
MW:
248.32
Mol File:
68370-47-8.mol
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Micheliolide Chemical Properties

Melting point:
131-133 °C
Boiling point:
426.1±45.0 °C(Predicted)
Density 
1.17±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
pka
14.65±0.40(Predicted)
color 
Off-White
InChI
InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1
InChIKey
RDJAFOWISVMOJY-PWNZVWSESA-N
SMILES
O1C(=O)C(=C)[C@]2([H])CCC(C)=C3[C@@]([H])([C@@]12[H])[C@@](O)(C)CC3
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Micheliolide Usage And Synthesis

Chemical Properties

Off-white powder, soluble in methanol, ethanol, DMSO and other organic solvents.

Uses

Micheliolide, a sesquiterpene lactone is used in the inhibition of resistant acute leukemic cells. Selectively targets cancer stem and progenitor cells.

Definition

ChEBI: Micheliolide is a sesquiterpene lactone.

Biological Activity

Micheliolide (MCL) is a sesquiterpene lactone isolated from Michelia compressa and Michelia champaca. Previous studies have demonstrated that MCL exerted various therapeutic effects in cancer, inflammation, immunomodulatory acute myelogenous leukemia and renal fibrosis through numerous signaling pathways, including PI3K/Akt, NF-kB and MAPK signaling. Dimethylaminomicheliolide (DMAMCL), the prodrug of MCL, has been approved by the US Food and Drug Administration for its apparent efficacy in treating pleomorphic glioblastoma. In China, DMAMCL is currently undergoing clinical trials to treat several advanced or metastatic solid carcinomas, including gliomas[2].

in vivo

Micheliolide (10 or 20 mg/kg, i.p., a single dose for 2 h) attenuates the secretion of serum cytokines and protects against lung and liver tissue damage in LPS (10mg/kg, i.p., a single dose for 2 h)-challenged mice[2].
Micheliolide (10 or 20 mg/kg, i.p., a single dose for 6 days) enhances the survival rate in mice following lethal septic shock[2].
Micheliolide (30 mg/kg, i.p., every two days for 63 days) reduces swelling of the paws and suppresses the degeneration of articular cartilage in collagen-induced arthritis mice[4].

Animal Model:Acute peritonitis mouse model[2]
Dosage:10 or 20 mg/kg
Administration:i.p., a single dose for 2 h
Result:Suppressed LPS-induced production of proinflammatory cytokines, chemokines and IFN in macrophages and DCs, showing clearer alveolar wall and less inflammatory cell infiltration.
Animal Model:Septic shock mouse model[2]
Dosage:10 or 20 mg/kg
Administration:i.p., a single dose for 6 days
Result:Protected mice against septic shock following lethal LPS challenge.
Animal Model:Collagen-induced arthritis mice[4]
Dosage:30 mg/kg
Administration:i.p., every two days for 63 days
Result:Remited the pathological changes of collagen-induced arthritis and recovered the expression levels of M-CSF, TIMP-1 and C5/C5a in collagen-induced arthritis mice.

Source

Micheliolide (MCL) is a potentially stable sesquiterpene lactone, which can be isolated from Magnolia grandiflora L., Michelia champaca L., and Michelia compressa (Maxim.) Sarg. MCL and its Michael adduct dimethylaminomicheliolide (DMAMCL) display significant cytotoxicity against tumours. MCL is known to be firstly isolated by Ogura, Cordell from Michelia compressa (Maxim.) Sarg. as a cytotoxic active component. MCL is also a main biologically active constituent of Michelia champaca L., Magnolia grandiflora L., and Tanacetum parthenium Sch. Bip., Anthemis scrobicularis Yavin, and Michelia compressa (Maxim.) Sarg[1].
  

References

[1] Jalal Uddin. “Pharmacological potential of micheliolide: A focus on anti-inflammatory and anticancer activities.” Heliyon 10 6 (2024): e27299.
[2] Dingkun Feng. “Micheliolide suppresses the viability, migration and invasion of U251MG cells via the NF-κB signaling pathway.” Oncology Letters 20 4 (2020): 67.

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