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Details

Stereochemistry RACEMIC
Molecular Formula C12H16O4
Molecular Weight 224.2535
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SENKYUNOLIDE I

SMILES

CCC/C(/[H])=C\1/C2=C([C@@]([H])([C@]([H])(CC2)O)O)C(=O)O1

InChI

InChIKey=DQNGMIQSXNGHOA-JXQVETIVSA-N
InChI=1S/C12H16O4/c1-2-3-4-9-7-5-6-8(13)11(14)10(7)12(15)16-9/h4,8,11,13-14H,2-3,5-6H2,1H3/b9-4-/t8-,11+/m0/s1

HIDE SMILES / InChI

Molecular Formula C12H16O4
Molecular Weight 224.2535
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21235591

Senkyunolide I is an active ingredient of Rhizoma Chuanxiong, a Chinese medicinal herb commonly used for the treatment of cardiovascular ailments. Senkyunolide I is presentative metabolite of ligustilide in vivo and in vitro, is one of the most important bioactive constituents of chuanxiong. It was fount, that it could treat migraines, although the mechanism is unclear.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Senkyunolide I protects rat brain against focal cerebral ischemia-reperfusion injury by up-regulating p-Erk1/2, Nrf2/HO-1 and inhibiting caspase 3.
2015 Apr 24
Preparation and structural determination of four metabolites of senkyunolide I in rats using ultra performance liquid chromatography/quadrupole-time-of-flight tandem mass and nuclear magnetic resonance spectra.
2016 Dec 5
Elucidation of Transport Mechanism of Paeoniflorin and the Influence of Ligustilide, Senkyunolide I and Senkyunolide A on Paeoniflorin Transport through Mdck-Mdr1 Cells as Blood-Brain Barrier in Vitro Model.
2016 Mar 2
Senkyunolide I attenuates oxygen-glucose deprivation/reoxygenation-induced inflammation in microglial cells.
2016 Oct 15
Patents

Sample Use Guides

in rats: oral administration at a dose of 100 mg*kg−1/body weight
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: It was found, that senkyunolide I (SEI) suppressed the activation of NF-κB pathway induced by oxygen-glucose deprivation/reoxygenation (OGD/R) and the MAPK pathway was shown not to be involved. Furthermore, SEI significantly down-regulated TLR4/MyD88 pathway with specifically improving inducible Hsp70 level through increasing HSF-1/DNA binding activity. SEI exerted similar influence on Hsp70/TLR4/NF-κB pathway in rat primary microglial cells. The results suggested that SEI had a potent effect against stroke-induced neuroinflammation through suppressing the TLR4/NF-κB pathway by up-regulating Hsp70 dependent on HSF-1.
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:02:58 UTC 2021
Edited
by admin
on Sat Jun 26 14:02:58 UTC 2021
Record UNII
12PJ07292V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SENKYUNOLIDE I
Common Name English
LIGUSTILIDIOL
Common Name English
LIGUSTILIDIOL, (Z)-
Common Name English
(Z)-LIGUSTILIDIOL
Common Name English
1(3H)-ISOBENZOFURANONE, 3-BUTYLIDENE-4,5,6,7-TETRAHYDRO-6,7-DIHYDROXY-, (3Z,6.ALPHA.,7.BETA.)-
Common Name English
TRANS-6,7-DIHYDROXYLIGUSTILIDE
Common Name English
1(3H)-ISOBENZOFURANONE, 3-BUTYLIDENE-4,5,6,7-TETRAHYDRO-6,7-DIHYDROXY-, (3Z,6R,7R)-REL-
Systematic Name English
Code System Code Type Description
FDA UNII
12PJ07292V
Created by admin on Sat Jun 26 14:02:58 UTC 2021 , Edited by admin on Sat Jun 26 14:02:58 UTC 2021
PRIMARY
CAS
88551-87-5
Created by admin on Sat Jun 26 14:02:58 UTC 2021 , Edited by admin on Sat Jun 26 14:02:58 UTC 2021
ALTERNATIVE
PUBCHEM
11521428
Created by admin on Sat Jun 26 14:02:58 UTC 2021 , Edited by admin on Sat Jun 26 14:02:58 UTC 2021
PRIMARY
CAS
94596-28-8
Created by admin on Sat Jun 26 14:02:58 UTC 2021 , Edited by admin on Sat Jun 26 14:02:58 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Senkyunolide I, coniferyl ferulate, senkyunolide A, 3-butylphthalide, Z-butylidenephthalide and levistolide A were isolated from essential oil of Angelica sinensis.