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
Molecular Formula | C24H28O4 |
Molecular Weight | 380.4767 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 2 |
Optical Activity | UNSPECIFIED |
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 |
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Target ID: GO:0070059 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28662507 |
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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 |
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[Studies on chemical constituents of the rhizomae of Ligusticum chuanxiong]. | 2002 Jul |
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Studies on antiproliferative effects of phthalides from Ligusticum chuanxiong in hepatic stellate cells. | 2007 Jun |
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Levistolide A overcomes P-glycoprotein-mediated drug resistance in human breast carcinoma cells. | 2008 Apr |
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Ligusticum chuanxiong Hort: a review of chemistry and pharmacology. | 2011 Nov |
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Levistolide A Induces Apoptosis via ROS-Mediated ER Stress Pathway in Colon Cancer Cells. | 2017 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25657289
Rats were treated with Levistolide A at the doses of 20mk/kg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28662507
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 19:58:50 UTC 2023
by
admin
on
Sat Dec 16 19:58:50 UTC 2023
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Record UNII |
29MRT0H4CE
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Record Status |
Validated (UNII)
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Record Version |
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88182-33-6
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DTXSID601317628
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Senkyunolide I, coniferyl ferulate, senkyunolide A, 3-butylphthalide, Z-butylidenephthalide and levistolide Awere isolated from essential oil of Angelica sinensis.
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