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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H24O10
Molecular Weight 388.3665
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENIPOSIDE

SMILES

[H][C@]12CC=C(CO)[C@@]1([H])[C@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(=O)OC

InChI

InChIKey=IBFYXTRXDNAPMM-BVTMAQQCSA-N
InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26976766 https://www.ncbi.nlm.nih.gov/pubmed/26496899

Geniposide, a key component extracted from the fruit of Gardenia jasminoides Ellis, is a major iridoid glycoside considered to be responsible for various biological effects of the herbs, and its aglycon is genipin. Gardenia is a widely used Chinese herb for the treatment of hepatic disease, inflammation disorders, contusions and brain disorders. Increasing studies have focused on the neuroprotective effect of geniposide in brain diseases, especially neurodegenerative disorders. Its protective effect from memory impairment and the normalization of objection recognition has been shown in animal behavioral experiments. Using a high-throughput screen for GLP-1R agonists, geniposide was identified as an agonist for GLP-1R. It has been shown that the activation of GLP-1R by geniposide induces neurotrophic and neuroprotective effects in cells. Geniposide exerted anti-inflammatory effects by interfering with the expression of P2Y14 receptor, which subsequently inhibits the downstream ERK1/2 signaling pathways and the release of the pro-inflammatory cytokines IL-8, MCP-1, IL-1β.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O35881
Gene ID: 171108.0
Gene Symbol: P2ry14
Target Organism: Rattus norvegicus (Rat)
Conditions
PubMed

PubMed

TitleDatePubMed
Differential induction of the expression of GST subunits by geniposide in rat hepatocytes.
2004 Jan
Biotransformation of geniposide by human intestinal microflora on cytotoxicity against HepG2 cells.
2012 Mar 25
Glucagon-like peptide 1 receptor plays an essential role in geniposide attenuating lipotoxicity-induced β-cell apoptosis.
2012 Oct
Patents

Sample Use Guides

Rats: 228.00 mg/kg geniposide by gavage
Route of Administration: Oral
Geniposide (0.01-100 umol/L) increased insulin secretion from INS-1 cells in a concentration-dependent manner. Geniposide (10 umol/L) enhanced acute insulin secretion in response to both the low (5.5 mmol/L) and moderately high levels (11 mmol/L) of glucose.
Name Type Language
GENIPOSIDE
Common Name English
JASMINOIDIN
Common Name English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)- 1,4A,5,7A-TETRAHYDRO-7-(HYDROXYMETHYL)-, METHYL ESTER, (1S,4AS,7AS)-
Systematic Name English
Code System Code Type Description
PUBCHEM
107848
Created by admin on Fri Dec 15 19:52:25 GMT 2023 , Edited by admin on Fri Dec 15 19:52:25 GMT 2023
PRIMARY
WIKIPEDIA
Geniposide
Created by admin on Fri Dec 15 19:52:25 GMT 2023 , Edited by admin on Fri Dec 15 19:52:25 GMT 2023
PRIMARY
CAS
24512-63-8
Created by admin on Fri Dec 15 19:52:25 GMT 2023 , Edited by admin on Fri Dec 15 19:52:25 GMT 2023
PRIMARY
FDA UNII
145295QLXY
Created by admin on Fri Dec 15 19:52:25 GMT 2023 , Edited by admin on Fri Dec 15 19:52:25 GMT 2023
PRIMARY
MESH
C007835
Created by admin on Fri Dec 15 19:52:25 GMT 2023 , Edited by admin on Fri Dec 15 19:52:25 GMT 2023
PRIMARY
CAS
169799-41-1
Created by admin on Fri Dec 15 19:52:25 GMT 2023 , Edited by admin on Fri Dec 15 19:52:25 GMT 2023
NO STRUCTURE GIVEN
EPA CompTox
DTXSID101318419
Created by admin on Fri Dec 15 19:52:25 GMT 2023 , Edited by admin on Fri Dec 15 19:52:25 GMT 2023
PRIMARY