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

Micheliolide Usage And Synthesis

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].

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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