U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O11
Molecular Weight 414.3607
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASPERULOSIDE

SMILES

[H][C@]12OC(=O)C3=CO[C@@H](O[C@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@]([H])(C(COC(C)=O)=C1)[C@]23[H]

InChI

InChIKey=IBIPGYWNOBGEMH-DILZHRMZSA-N
InChI=1S/C18H22O11/c1-6(20)25-4-7-2-9-12-8(16(24)27-9)5-26-17(11(7)12)29-18-15(23)14(22)13(21)10(3-19)28-18/h2,5,9-15,17-19,21-23H,3-4H2,1H3/t9-,10+,11+,12-,13+,14-,15+,17-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H22O11
Molecular Weight 414.3607
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including

Asperuloside, an iridoid glycoside found in Herba Paederiae, is a component from traditional Chinese herbal medicine. Asperuloside is extracted from many traditional Chinese medicinal plants, including Herba Paederiae, Asperula odorata, Goldhair Hedyotis Herb and Hedyotis diffusa. It has been proved that there are many kinds of pharmacological effects such as anti-tumor and anti-obesity activities. Asperuloside can significantly downregulate tumor necrosis factor alpha (TNF-α), interleukin (IL)-1β, and IL-6 levels in vitro and in vivo, and treatment with asperuloside significantly reduced the lung wet-to-dry weight, histological alterations and myeloperoxidase activity in a murine model of LPS-induced acute lung injury (ALI). Asperuloside exerts its anti-inflammatory effect in correlation with inhibition of a pro-inflammatory mediator through suppressing nuclear factor kappa-B (NF-κB) nuclear translocation and MAPK phosphorylation. Asperuloside can be a potential treatment for ALI and can be used as a clinical anti-infective drug.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Three new and antitumor anthraquinone glycosides from Lasianthus acuminatissimus MERR.
2006 Mar
Patents

Sample Use Guides

20, 40, and 80 mg/kg, given intraperitoneally
Route of Administration: Intraperitoneal
Asperuloside ((20–80 mg/L) significantly downregulates tumor necrosis factor alpha (TNF-α), interleukin (IL)-1β, and IL-6 levels in RAW 264.7 cells
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:32:51 UTC 2023
Edited
by admin
on Fri Dec 15 18:32:51 UTC 2023
Record UNII
V3CFI02X39
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASPERULOSIDE
MI  
Common Name English
ASPERULOSIDE [MI]
Common Name English
(2AS,4AS,5S,7BS)-4-((ACETYLOXY)METHYL)-5-(.BETA.-D-GLUCOPYRANOSYLOXY)-2A,4A,5,7B-TETRAHYDRO-1H-2,6-DIOXACYCLOPENT(CD)INDEN-1-ONE
Common Name English
NSC-31760
Code English
RUBICHLORIC ACID
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
238-137-5
Created by admin on Fri Dec 15 18:32:51 UTC 2023 , Edited by admin on Fri Dec 15 18:32:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID70878339
Created by admin on Fri Dec 15 18:32:51 UTC 2023 , Edited by admin on Fri Dec 15 18:32:51 UTC 2023
PRIMARY
PUBCHEM
84298
Created by admin on Fri Dec 15 18:32:51 UTC 2023 , Edited by admin on Fri Dec 15 18:32:51 UTC 2023
PRIMARY
CAS
14259-45-1
Created by admin on Fri Dec 15 18:32:51 UTC 2023 , Edited by admin on Fri Dec 15 18:32:51 UTC 2023
PRIMARY
NSC
31760
Created by admin on Fri Dec 15 18:32:51 UTC 2023 , Edited by admin on Fri Dec 15 18:32:51 UTC 2023
PRIMARY
FDA UNII
V3CFI02X39
Created by admin on Fri Dec 15 18:32:51 UTC 2023 , Edited by admin on Fri Dec 15 18:32:51 UTC 2023
PRIMARY
MERCK INDEX
m2104
Created by admin on Fri Dec 15 18:32:51 UTC 2023 , Edited by admin on Fri Dec 15 18:32:51 UTC 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT