Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C24H28O4 |
| Molecular Weight | 380.4767 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC3=C(C(=O)O\C3=C/CCC)[C@]1([H])[C@@]45CC[C@@H]2C=C4C(=O)O\C5=C/CCC
InChI
InChIKey=UBBRXVRQZJSDAK-ZJHGLIIDSA-N
InChI=1S/C24H28O4/c1-3-5-7-18-16-10-9-15-14-11-12-24(21(15)20(16)23(26)27-18)17(13-14)22(25)28-19(24)8-6-4-2/h7-8,13-15,21H,3-6,9-12H2,1-2H3/b18-7-,19-8-/t14-,15+,21-,24+/m1/s1
Levistolide A is a naturally occurring compound isolated from Ligusticum chuanxiong Hort, which is used in traditional Chinese medicine to treat cancer. Levistolide has been studied in vitro against cell models for colon cancer and breast cancer. It was effective at inducing ER programmed apoptosis in colon cancer cells. In a cell model for breast cancer, levistolide was shown to enhance the apoptotic effects of adriamycin and vincristine. The effect of levistomide is correlated with cleavage of poly(ADP-ribose) polymerase PARP and up-regulation of caspase-3.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3390820 |
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Target ID: P42574 Gene ID: 836.0 Gene Symbol: CASP3 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Secondary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Studies on chemical constituents of the rhizomae of Ligusticum chuanxiong]. | 2002 Jul |
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| Ligusticum chuanxiong Hort: a review of chemistry and pharmacology. | 2011 Nov |
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| Screening anti-tumor compounds from Ligusticum wallichii using cell membrane chromatography combined with high-performance liquid chromatography and mass spectrometry. | 2015 Sep |
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| The variation in the major constituents of the dried rhizome of Ligusticum chuanxiong (Chuanxiong) after herbal processing. | 2016 |
Sample Use Guides
Rats were treated with Levistolide A at the doses of 20mk/kg
Route of Administration:
Oral
HCT116 and HCT116 p53-/- colon cancer cells were maintained in DMEM with 10% FBS, 100 U/mL penicilin, and 100 micro-g/mL streptomycin at 37 deg-C and an atmosphere with 5% CO2. Cells were treated with different concentrations (0, 25, 50, 100 and 200 µM) of Levistolide A for 24 h and 48 h. Cell viability was assessed by use of an MTT assay. The viability of HCT116 cells was inhibited by Levistolide A in a time- and dose-dependent manner through induction of apoptosis via the Endoplasmic Reticulum Stress Pathway, mediated by the presence of reactive oxygen species.
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SUBSTANCE RECORD
