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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H28O4
Molecular Weight 380.4776
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of LEVISTOLIDE A

SMILES

CCC/C(/[H])=C\1/C2=C([C@@]3([H])[C@@]([H])(CC2)[C@]4([H])CC[C@]/53C(=C4)C(=O)O\C5=C(\[H])/CCC)C(=O)O1

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

HIDE SMILES / InChI

Molecular Formula C24H28O4
Molecular Weight 380.4776
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.

Originator

Sources: Plantes Medicinales et Phytotherapie (1983), 17, (3), 147-56. CODEN:PLMPA9 ISSN:0032-0994.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Secondary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Studies on chemical constituents of the rhizomae of Ligusticum chuanxiong].
2002 Jul
Levistolide A overcomes P-glycoprotein-mediated drug resistance in human breast carcinoma cells.
2008 Apr
Screening anti-tumor compounds from Ligusticum wallichii using cell membrane chromatography combined with high-performance liquid chromatography and mass spectrometry.
2015 Sep
The variation in the major constituents of the dried rhizome of Ligusticum chuanxiong (Chuanxiong) after herbal processing.
2016
Patents

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:40:37 UTC 2021
Edited
by admin
on Sat Jun 26 02:40:37 UTC 2021
Record UNII
29MRT0H4CE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVISTOLIDE A
Common Name English
(Z,Z)-DILIGUSTILIDE
Common Name English
1H-5,10C-ETHANONAPHTHO(1,2-C:7,8-C')DIFURAN-3,10-DIONE, 1,8-DIBUTYLIDENE-5,5A,6,7,8,10B-HEXAHYDRO-, (1Z,5S,5AS,8Z,10BS,10CS)-
Systematic Name English
LEVISTOLIDE A [INCI]
Common Name English
DILIGUSTILIDE
Common Name English
LEVISTOLID A
Common Name English
Z,Z'-6,6',7,3'A-DILIGUSTILIDE
Common Name English
Code System Code Type Description
FDA UNII
29MRT0H4CE
Created by admin on Sat Jun 26 02:40:37 UTC 2021 , Edited by admin on Sat Jun 26 02:40:37 UTC 2021
PRIMARY
CAS
88182-33-6
Created by admin on Sat Jun 26 02:40:37 UTC 2021 , Edited by admin on Sat Jun 26 02:40:37 UTC 2021
PRIMARY
PUBCHEM
70698035
Created by admin on Sat Jun 26 02:40:37 UTC 2021 , Edited by admin on Sat Jun 26 02:40:37 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Senkyunolide I, coniferyl ferulate, senkyunolide A, 3-butylphthalide, Z-butylidenephthalide and levistolide Awere isolated from essential oil of Angelica sinensis.