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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

Molecular Formula C17H24O10
Molecular Weight 388.3665
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rats: 228.00 mg/kg geniposide by gavage
Route of Administration: Oral
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
145295QLXY
Record Status Validated (UNII)
Record Version