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Home > Products >  Geniposide

Geniposide CAS NO.24512-63-8

  • Min.Order: 10 Milligram
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Keywords

  • Geniposide
  • 24512-63-8
  • standard supplier in China

Quick Details

  • ProName: Geniposide
  • CasNo: 24512-63-8
  • Molecular Formula: C17H24O10=388.4
  • Appearance: detailed see specifications
  • Application: analysis,activity test,Botanical Refer...
  • DeliveryTime: 1-3?working?days?after?confirming?the?...
  • PackAge: According to the clients requirement.
  • Port: China main port
  • ProductionCapacity: 1 Metric Ton/Day
  • Purity: ≥98%
  • Storage: Store at 2~8°C
  • Transportation: by air or by ocean shipping
  • LimitNum: 10 Milligram
  • Plant of Origin: Chinese herbal medicine
  • Testing Method: NMR/MS/HPLC
  • Product Ecification: 1mg-1kg
  • Heavy Metal: <10ppm
  • Voluntary Standards: company standard
  • Storage: Store in dry, dark and ventilated plac...
  • PackAge: Brown vial HDPE plastic bottle

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers. 
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.
 
Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library
 

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

General tips:For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging:1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition:Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Details

Chemical Properties of Geniposide

Cas No. 24512-63-8 SDF  
PubChem ID 107848 Appearance White powder
Formula C17H24O10 M.Wt 388.4
Type of Compound Iridoids Storage Desiccate at -20°C
Solubility DMSO : 100 mg/mL (257.49 mM; Need ultrasonic)
Chemical Name methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILES COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)CO)O)O)O
Standard InChIKey IBFYXTRXDNAPMM-BVTMAQQCSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Geniposide

1 Cornus sp. 2 Eucommia sp. 3 Euphrasia sp. 4 Gardenia sp. 5 Rehmannia sp.

Biological Activity of Geniposide

Description Geniposide exhibits anti-diabetic, antidepressant-like, antioxidative, anti-apoptotic, antiproliferative and neuroprotective activities. Geniposide is an agonist for GLP-1 receptor, it regulates expression of anti-oxidative proteins including HO-1 and Bcl-2 by activating the transcriptor of p90RSK via MAPK signaling pathway in PC12 cells. Geniposide may suppress TGF-β1-induced EMT in hepatic fibrosis by inhibiting the TGFβ/Smad and ERK-mitogen-activated protein kinase (MAPK) signaling pathways.
Targets TLR | p53 | Bcl-2/Bax | Caspase | TGF-β/Smad | ERK | p38MAPK | HO-1 | MEK | Raf | Beta Amyloid | BACE | TNF-α | IL Receptor | JNK | ROS | NF-kB | IkB | IKK
In vitro

Geniposide, a novel agonist for GLP-1 receptor, prevents PC12 cells from oxidative damage via MAP kinase pathway.[Pubmed: 17629357]

Neurochem Int. 2007 Nov-Dec;51(6-7):361-9.

Alzheimer's disease (AD) is the most common form of dementia. Glucagon-like peptide-1 (GLP-1) gives a new genre in therapeutic targets for intervention in AD with its neurotrophic and neuroprotective functions. In previous work, we identified that Geniposide is a novel agonist for GLP-1 receptor, which shows neurotrophic characteristics to induce the neuronal differentiation of PC12 cells.
METHODS AND RESULTS:
The aim of this study is to determine whether Geniposide prevents neurons from oxidative damage, and to explore its signaling pathways. The results demonstrated that Geniposide increased the expression of anti-apoptotic proteins, including Bcl-2 and heme oxygenase-1 (HO-1), to antagonize the oxidative damage in PC12 cells induced by hydrogen peroxide. LY294002 (a PI3K inhibitor) inhibited the effect of Geniposide increasing of Bcl-2 level by activation of MAPK, MEK and c-Raf phosphorylation in hydrogen peroxide treated PC12 cells. U0126 (a selective inhibitor of MEK) also attenuated the enhancement of Geniposide on Bcl-2 level by inhibiting the phosphorylation of p90RSK in the hydrogen peroxide treated PC12 cells.
CONCLUSIONS:
All these data demonstrate that Geniposide, an agonist for GLP-1 receptor, regulates expression of anti-oxidative proteins including HO-1 and Bcl-2 by activating the transcriptor of p90RSK via MAPK signaling pathway in PC12 cells.

Geniposide, from Gardenia jasminoides Ellis, inhibits the inflammatory response in the primary mouse macrophages and mouse models.[Pubmed: 22878137 ]

Int Immunopharmacol. 2012 Dec;14(4):792-8.

Geniposide, a main iridoid glucoside component of gardenia fruit, has been known to exhibit antibacterial, anti-inflammatory and other important therapeutic activities. The objective of this study was to investigate the protective effects of Geniposide on inflammation in lipopolysaccharide (LPS) stimulated primary mouse macrophages in vitro and LPS induced lung injury model in vivo.
METHODS AND RESULTS:
The expression of pro-inflammatory cytokines was determined by enzyme-linked immunosorbent assay (ELISA). Nuclear factor-kappa B (NF-κB), inhibitory kappa B (IκBα) protein, p38, extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK) and Toll-like receptor 4 (TLR4) were determined by Western blot. Further analysis was carried out in mTLR4 and mMD-2 co-transfected HEK293 cells. The results showed that Geniposide markedly inhibited the LPS-induced TNF-α, IL-6 and IL-1β production both in vitro and in vivo. Geniposide blocked the phosphorylation of IκBα, p65, p38, ERK and JNK in LPS stimulated primary mouse macrophages. Furthermore, Geniposide inhibited the expression of TLR4 in LPS stimulated primary mouse macrophages and inhibited the LPS-induced IL-8 production in HEK293-mTLR4/MD-2 cells. In vivo study, it was also observed that Geniposide attenuated lung histopathologic changes in the mouse models.
CONCLUSIONS:
These results suggest that Geniposide exerts an anti-inflammatory property by down-regulating the expression of TLR4 up-regulated by LPS. Geniposide is highly effective in inhibiting acute lung injury and may be a promising potential therapeutic reagent for acute lung injury treatment.

In vivo

Antidepressant-like effect of geniposide on chronic unpredictable mild stress-induced depressive rats by regulating the hypothalamus-pituitary-adrenal axis.[Pubmed: 25914157]

Eur Neuropsychopharmacol. 2015 Apr 17.

Geniposide as the major active component of Gardenia jasminoides Ellis has neuroprotective activity.
METHODS AND RESULTS:
This study elucidated the potential antidepressant-like effect of Geniposide and its related mechanisms using a depression rat model induced by 3 consecutive weeks of chronic unpredictable mild stress (CUMS). Sucrose preference test, open field test (OFT) and forced swimming test (FST) were applied to evaluate the antidepressant effect of Geniposide. We found that Geniposide (25, 50, 100mg/kg) treatment reversed the CUMS-induced behavioral abnormalities, as suggested by increased sucrose intake, improved crossing and rearing behavior in OFT, shortened immobility and prolonged swimming time in FST. Additionally, Geniposide treatment normalized the CUMS-induced hyperactivity of HPA axis, as evidenced by reduced CORT serum level, adrenal gland index and hypothalamic CRH mRNA expression, with no significant effect on ACTH serum level. Moreover, Geniposide treatment upregulated the hypothalamic GRα mRNA level and GRα protein expression in PVN, suggesting Geniposide could recover the impaired GRα negative feedback on CRH expression and HPA axis.
CONCLUSIONS:
These aforementioned therapeutic effects of Geniposide were essentially similar to fluoxetine.
Our results indicated that Geniposide possessed potent antidepressant-like properties that may be mediated by its effects on the HPA axis.

Protocol of Geniposide

Kinase Assay

Geniposide inhibits high glucose-induced cell adhesion through the NF-kappaB signaling pathway in human umbilical vein endothelial cells.[Pubmed: 20686520 ]

Effects of geniposide on hepatocytes undergoing epithelial-mesenchymal transition in hepatic fibrosis by targeting TGFβ/Smad and ERK-MAPK signaling pathways.[Pubmed: 25818617]

Geniposide inhibited lipopolysaccharide-induced apoptosis by modulating TLR4 and apoptosis-related factors in mouse mammary glands.[Pubmed: 25445441]

Life Sci. 2014 Dec 5;119(1-2):9-17.

Geniposide, a major iridoid glycoside found in gardenia fruit, is widely used in Asian countries for its anti-inflammatory, anti-tumor and anti-apoptotic activities. Although the anti-inflammatory effect of Geniposide has been widely reported, its anti-apoptotic role in mastitis remains unclear. In the present study, we investigated whether Geniposide exerts anti-apoptotic activity in lipopolysaccharide (LPS)-induced mouse mammary glands.
METHODS AND RESULTS:
We established a LPS-induced mouse mastitis model and LPS-stimulated primary mouse mammary epithelial cells (mMECs) model to investigate the anti-apoptotic effect of Geniposide and the underlying mechanism of action.Geniposide alleviated mammary gland apoptosis, down-regulated Bax expression, inhibited Caspase-3 cleavage and p53 phosphorylation and up-regulated Bcl-2 expression in vivo. In vitro, Geniposide decreased the ratio of dead cells in a dose-dependent manner. Geniposide inhibited Bax expression and Caspase-3 cleavage, and up-regulated the expression of Bcl-2. Moreover, Geniposide down-regulated the expression of TLR4 and repressed the phosphorylation of p53.
CONCLUSIONS:
These results demonstrate that the anti-apoptotic property of Geniposide is due to its modulation of TLR4 and apoptosis-related factors (p53, Bax, Bcl-2 and Caspase-3) in LPS-induced mouse mastitis.

Biochimie. 2015 Jun;113:26-34.

Liver fibrosis results from increased deposition of type-I collagen within the hepatic extracellular space and constitutes a common cardinal signature in all forms of liver injury, regardless of etiology. Transforming growth factor β1 (TGF-β1) plays a crucial role in the pathogenesis of liver fibrosis. Geniposide is recognized as being useful against hyperlipidemia and fatty liver. However, its cellular mechanism and anti-fibrotic effect in TGF-β1-induced hepatocytes have not been explored.
METHODS AND RESULTS:
In the present study, we investigated its anti-epithelial-mesenchymal transition (EMT) mechanism by examining the effect of Geniposide on TGF-β1-induced hepatocytes. The effect of Geniposide on TGF-β1-induced AML12 cells was assessed using Western blotting, quantitative real-time PCR, immunofluorescence staining and DNA binding activity. We found that Geniposide significantly inhibited TGF-β1-induced mRNA and protein expression of type-I collagen. Cells treated concurrently with TGF-β1 and Geniposide retained high levels of localized E-cadherin expression with no increase in vimentin. Treatment with Geniposide almost completely blocked the phosphorylation of Smad2/3, extracellular signal-regulated kinase (ERK) and Akt in AML12 cells.
CONCLUSIONS:
Taken together, these results suggest that Geniposide may suppress TGF-β1-induced EMT in hepatic fibrosis by inhibiting the TGFβ/Smad and ERK-mitogen-activated protein kinase (MAPK) signaling pathways. Our results may help researchers better understand the pathogenesis of liver fibrosis so they can develop novel therapeutic strategies for treatment of liver diseases.

Acta Pharmacol Sin. 2010 Aug;31(8):953-62.

To investigate whether Geniposide, an iridoid glucoside extracted from gardenia jasminoides ellis fruits, inhibits cell adhesion to human umbilical vein endothelial cells (HUVECs) induced by high glucose and its underlying mechanisms.
METHODS AND RESULTS:
HUVECs were isolated from human umbilical cords and cultured. The adhesion of monocytes to HUVECs was determined using fluorescence-labeled monocytes. The mRNA and protein levels of vascular cell adhesion molecule-1 (VCAM-1) and endothelial selectin (E-selectin) were measured using real-time RT-PCR and ELISA. Reactive oxygen species (ROS) production was measured using a fluorescent probe. The amounts of nuclear factor-kappa B (NF-kappaB) and inhibitory factor of NF-kappaB (IkappaB) were determined using Western blot analysis. The translocation of NF-kappaB from the cytoplasm to the nucleus was determined using immunofluorescence. Geniposide (10-20 mumol/L) inhibited high glucose (33 mmol/L)-induced adhesion of monocytes to HUVECs in a dose-dependent manner. This compound (5-40 mumol/L) also inhibited high glucose-induced expression of VCAM-1 and E-selectin at the gene and protein levels. Furthermore, Geniposide (5-20 micromol/L) decreased ROS production and prevented IkappaB degradation in the cytoplasm and NF-kappaB translocation from the cytoplasm to the nucleus in HUVECs.
CONCLUSIONS:
Geniposide inhibits the adhesion of monocytes to HUVECs and the expression of CAMs induced by high glucose, suggesting that the compound may represent a new treatment for diabetic vascular injury. The mechanism underlying this inhibitory effect may be related to the inhibition of ROS overproduction and NF-kappaB signaling pathway activation by Geniposide.

Animal Research

Geniposide attenuates insulin-deficiency-induced acceleration of β-amyloidosis in an APP/PS1 transgenic model of Alzheimer's disease.[Pubmed: 25882165]

Neurochem Int. 2015 Oct;89:7-16.

Our previous studies have shown that Geniposide plays an essential role in glucose-stimulated insulin secretion from pancreatic β cells and also antagonizesAβ1-42-induced cytotoxicity examined using a primary cortical neuron assay. However, the mechanism by which Geniposide appears to regulate insulin signaling in the brain is presently not well understood.
METHODS AND RESULTS:
In this study, we administered streptozotocin (STZ) to induce insulin-deficiency in an AD transgenic mouse model, and investigated the effects of Geniposide on the β-amyloidogenic processing of amyloid precursor protein (APP) using in vitro and in vivo models. Our results indicate that treatment with STZ (90 mg/kg, i.p., once daily for two consecutive days) induced significant reduction in peripheral and brain insulin levels in both wild-type and APP/PS1 transgenic mice. Administration of Geniposide for 4 weeks significantly decreased the concentrations of cerebral β-amyloid peptides (Aβ1-40 and Aβ1-42) in STZ-treated AD mice. Further experiments showed that Geniposide up-regulated the protein levels of β-site APP cleaving enzyme (BACE1) and insulin-degrading enzyme (IDE), and decreased the protein levels of ADAM10 when examined using a primary cultured cortical neuron assay and in STZ-induced AD mice. Meanwhile, Geniposide also directly enhanced the effects of insulin by reducing Aβ1-42 levels in primary cultured cortical neurons.
CONCLUSIONS:
Taken together, our findings provide a mechanistic link between diabetes and AD, and is consistent with the notion that Geniposide might play an important role on APP processing via enhancing insulin signaling and may convey a therapeutic benefit in AD.

Preparing Stock Solutions of Geniposide

  1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5747 mL 12.8733 mL 25.7467 mL 51.4933 mL 64.3666 mL
5 mM 0.5149 mL 2.5747 mL 5.1493 mL 10.2987 mL 12.8733 mL
10 mM 0.2575 mL 1.2873 mL 2.5747 mL 5.1493 mL 6.4367 mL
50 mM 0.0515 mL 0.2575 mL 0.5149 mL 1.0299 mL 1.2873 mL
100 mM 0.0257 mL 0.1287 mL 0.2575 mL 0.5149 mL 0.6437 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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