Geniposide

Names

[ Name ]:
Geniposide

[Synonym ]:
Olea europaea L
Methyl (1S)-1-(β-D-glucopyranosyloxy)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Geniposide
Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-
Geniposidic
Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S)-
Cyclopenta(c)pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-
Jasminoidin
Methyl (1S,4aS,7aS)-1-(β-D-glucopyranosyloxy)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Genipin 1-glucoside
MFCD00016659

Biological Activity

[Description]:

Geniposide is an iridoid glucoside extracted from Gardenia jasminoides Ellis fruits; exhibits a varity of biological activities such as anti-diabetic, antioxidative, antiproliferative and neuroprotective activities.

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Amyloid-β

Research Areas >> Neurological Disease

Natural Products >> Terpenoids and Glycosides

[In Vitro]

Geniposide exhibits a variety of activities, such as on antithrombosis, anti-inflammation, anti-diabetes, anti-atherosclerosis, antidepression, healing Alzheimer’s disease (AD), anti-hypertension, toxicology, and untoward reaction are summarized[1]. Geniposide markedly declines the production of IL-8, IL-1β and MCP-1 in OGD-induced brain microvascular endothelial cells, the expression of P2Y14 receptor is significantly down-regulated, the phosphorylation of RAF-1, MEK1/2, ERK1/2 are suppressed[2].

[In Vivo]

Geniposide (200 and 400 mg/kg) significantly decreases the blood glucose, insulin and TG levels in diabetic mice in a dose-dependent manner. This compound also decreases the expression of GP and G6Pase at mRNA and immunoreactive protein levels, as well as enzyme activity[3]. Geniposide (20.0, 40.0, or 80 mg/kg) significantly reverses the excessive, alcohol-induced elevation in both serum ALT/AST and hepatic LPO levels. Geniposide upregulates the expression of heme oxygenase-1 (HO-1) to attenuate the cell apoptosis induced by 3-morpholinosydnonimine hydrochloride (SIN-1) in primary cultured hippocampal neurons[4]. Geniposide inhibits photochemistry-induced thromboembolism model in vivo. Geniposide are very effective depressants on NF-κB by interrupting IκB degradation[1].

[Cell Assay]

The third passages of brain microvascular endothelial cells (BMECs) are used for the experiment. The BMECs are divided into four groups: (1)normal control group: the normal cultured BMECs without treatment; (2)OGD group: the BMECs injured by OGD according to the above method; (3) geniposide group: the OGD-injured BMECs treated with 33.2 μg/mL geniposide for 6 h; (4)PTX group: the OGD-injured BMECs administrated with 100 ng/mL PTX. PTX, known as an inhibitor of Gi-coupled receptor is used to assess the activation of P2Y14 receptor induced by OGD in this experiment[2].

[Animal admin]

Mice: Type 2 diabetic mice, induced by a high-fat diet and streptozotocin injection, are treated with or without geniposide for 2 weeks. Blood glucose levels are monitored by a glucometer. Insulin concentrations are analyzed by the ELISA method. Total cholesterol (TC) and triglyceride (TG) levels are measured using Labassay kits. Activities of hepatic GP and G6Pase are measured by glucose-6-phosphate dehydrogenase-coupled reaction. Real-time RT-PCR and Western blotting are used to determine the mRNA and protein levels of both enzymes[3].

[References]

[1]. Liu H, et al. Fructus Gardenia (Gardenia jasminoides J. Ellis) phytochemistry, pharmacology ofcardiovascular, and safety with the perspective of new drugs development. J Asian Nat Prod Res. 2013;15(1):94-110.

[2]. Li F, et al. Geniposide attenuates inflammatory response by suppressing P2Y14 receptor and downstream ERK1/2 signaling pathway in oxygen and glucose deprivation-induced brain microvascular endothelial cells. J Ethnopharmacol. 2016 Jun 5;185:77-86.

[3]. Wu SY, et al. Effect of geniposide, a hypoglycemic glucoside, on hepatic regulating enzymes in diabetic mice induced by a high-fat diet and streptozotocin. Acta Pharmacol Sin. 2009 Feb;30(2):202-8.

[4]. Wang J, et al. Geniposide protects against acute alcohol-induced liver injury in mice via up-regulating the expression of the main antioxidant enzymes. Can J Physiol Pharmacol. 2015 Apr;93(4):261-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
641.4±55.0 °C at 760 mmHg

[ Melting Point ]:
161-162ºC

[ Molecular Formula ]:
C₁₇H₂₄O₁₀

[ Molecular Weight ]:
388.366

[ Flash Point ]:
231.5±25.0 °C

[ Exact Mass ]:
388.136932

[ PSA ]:
155.14000

[ LogP ]:
-1.92

[ Vapour Pressure ]:
0.0±4.3 mmHg at 25°C

[ Index of Refraction ]:
1.621

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26-S36/37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3.0

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

The effects of notoginsenoside R₁ on the intestinal absorption of geniposide by the everted rat gut sac model.

J. Ethnopharmacol. 142(1) , 136-43, (2012)

Geniposide is derived from Gardenia jasminoides Ellis (Rubiaceae). Its anti-inflammatory, antithrombotic effects as well as its preventive effect against ischemic stroke have been reported. Radix noto...

[Effects of geniposide on SNP-induced apoptosis of chondrocyte and cell cycle].

Zhongguo Gu Shang 26(3) , 232-5, (2013)

To study the effects of Geniposide on SNP(sodium nitroprusside)-induced apoptosis of chondrocyte in vitro and cell cycle.The chondrocyte of three-week-old SD rats were separated and cultivated. The se...

Pharmacokinetics of geniposide by monoclonal antibody-based icELISA in mice after oral administration of Huanglian-Jiedu-Tang.

Biol. Pharm. Bull. 37(9) , 1525-33, (2014)

Geniposide, Geniposide, the main active component in extracts of Gardenia jasminoides ELLIS., is one of the main components of Huanglian-Jiedu-Tang (HJT). This study aimed to validate an indirect comp...