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Geniposide

Cat No.:V21547 Purity: ≥98%
Geniposide is an iridoid glycoside found in gardenia flowers; possesses diverse biological effects like antidiabetic, antioxidant, antiproliferation, and neuro-protective (neuro-protection) activities.
Geniposide
Geniposide Chemical Structure CAS No.: 24512-63-8
Product category: Beta Amyloid
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Geniposide is an iridoid glycoside found in gardenia flowers; possesses diverse biological effects like antidiabetic, antioxidant, antiproliferation, and neuro-protective (neuro-protection) activities.
Geniposide (CAS#: 24512-63-8, molecular weight 388.37, molecular formula C17H24O10) is an iridoid glycoside with a variety of biological activities including neuroprotective, anti-diabetic, antiproliferative, and antioxidative activity. It is a major iridoid found in fruit and is widely used in Asian countries for its anti-inflammatory and anti-apoptotic activities. Geniposide demonstrates multifaceted bioactivities including antithrombotic, anti-inflammatory, antidiabetic, anti-atherosclerotic, antidepressant effects, and therapeutic potential for Alzheimer's disease. The compound significantly reduces IL-8 production.
Biological Activity I Assay Protocols (From Reference)
Targets
Geniposide targets multiple pathways and molecules involved in inflammation, apoptosis, and oxidative stress. Its anti-apoptotic activity is due to modulation of p53, Bax, Bcl-2, and Caspase-3-related factors. The compound's neuroprotective effects are mediated through its ability to reduce oxidative stress and inflammation. Its antithrombotic, anti-inflammatory, and antidiabetic activities involve modulation of various signaling pathways. The compound's specific molecular targets are being elucidated through ongoing research.
ln Vitro
Anti-thrombotic, anti-inflammatory, anti-diabetic, anti-atherosclerotic, anti-depressant, anti-hypertensive, toxicological, and adverse reaction properties are just a few of the actions of geniposide [1]. The production of IL-8, IL-1β, and MCP-1 in brain microvascular endothelial cells induced by OGD is significantly reduced by geniposide. This results in a significant inhibition of P2Y14 receptor expression and phosphorylation of RAF-1, MEK1/2, and ERK1/2[2].
Geniposide exhibits a variety of in vitro activities including antithrombotic, anti-inflammatory, anti-diabetic, anti-atherosclerotic, antidepressant, and neuroprotective effects. It significantly reduces IL-8 production. The compound's anti-apoptotic activity is mediated through modulation of p53, Bax, Bcl-2, and Caspase-3. Its antioxidant and antiproliferative activities have been demonstrated in various cell lines. The compound's effects on Alzheimer's disease-related pathology have been observed in vitro.
ln Vivo
In a dose-dependent way, geniposide (200 and 400 mg/kg) dramatically lowered insulin, TG, and blood glucose levels in diabetic patients. A considerable reduction in alcohol-induced blood ALT/AST and excessive rise of liver LPO levels can be achieved by using geniposide (20.0, 40.0, or 80 mg/kg), which also lowers immune protein response levels and GP and G6Pase expression at mRNA levels. By increasing the production of heme oxygenase-1 (HO-1), geniposide alleviates the transplantation-induced stress on primary cultured hippocampus neuron cells caused by 3-modenoimine hydrochloride (SIN-1) [4]. prevents IκB from degrading and turns into an extremely powerful NF-κB coupling [1].
Geniposide (100 mg/kg) prevents increases in apoptosis and decreases in the number of dopaminergic neurons in the substantia nigra in a mouse model of MPTP-induced Parkinson's disease. The compound is highly effective in inhibiting acute lung injury and may be a promising therapeutic reagent for acute lung injury treatment. Its neuroprotective, hepatoprotective, antithrombotic, and anti-inflammatory effects have been demonstrated in various in vivo models.
Enzyme Assay
In vitro enzyme assays for geniposide involve measuring its effects on enzymes involved in inflammation and oxidative stress. The compound's antioxidant activity is assessed using standard cell-free assays such as DPPH radical scavenging, ABTS, or FRAP. Its anti-inflammatory activity can be evaluated by measuring inhibition of inflammatory enzymes such as COX-2 or iNOS. The compound's effects on apoptosis-related proteins can be assessed using purified proteins or cell lysates. These assays provide mechanistic insights into the compound's biological activities.
Cell Assay
In vitro cell-based assays for geniposide involve treating various cell lines (neuronal cells, immune cells, cancer cells) with the compound to assess its effects on cell viability, apoptosis, inflammation, and oxidative stress. Apoptosis is quantified by measuring caspase activity, Bax/Bcl-2 ratio, and p53 expression. Cytokine production (IL-8, TNF-α, IL-6) is measured by ELISA. Oxidative stress is assessed by measuring reactive oxygen species levels and antioxidant enzyme activities. Cell viability is measured using MTT or similar assays. These cellular studies characterize the compound's pharmacological activities.
Animal Protocol
In vivo animal experiments for geniposide have been conducted in mouse models of MPTP-induced Parkinson's disease. Mice are treated with geniposide (100 mg/kg) and dopaminergic neuron loss and apoptosis in the substantia nigra are assessed. Acute lung injury models evaluate the compound's anti-inflammatory effects. Models of diabetes, depression, and Alzheimer's disease have also been used to assess efficacy. Efficacy endpoints include histopathological analysis, biomarker measurement, and behavioral assessments.
ADME/Pharmacokinetics
Geniposide has a molecular weight of 388.37 and a molecular formula of C17H24O10. It is an iridoid glycoside with good aqueous solubility due to its glycosidic structure. The compound is typically extracted from fruit sources. Specific pharmacokinetic data such as absorption, distribution, metabolism, and elimination have been characterized in preclinical studies. The compound is typically stored under recommended conditions for natural products.
Toxicity/Toxicokinetics
Specific toxicity data for geniposide is not extensively reported. As a natural compound from fruit sources with a history of use in traditional medicine, it is generally considered to have a favorable safety profile. However, toxicological effects and adverse reactions have been summarized in the literature. Comprehensive toxicological studies would be required for therapeutic development. Standard safety precautions should be taken when handling the compound in research settings.
References

[1]. 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]. 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]. 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]. 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.

Additional Infomation
Geniposide is a terpene glycoside. It has been reported to be found in Rehmannia glutinosa, Gardenia jasminoides, and other organisms with relevant data. See also: Gardenia jasminoides (whole plant, part).
Geniposide is an iridoid glycoside with diverse biological activities including neuroprotective, anti-diabetic, antiproliferative, antioxidative, anti-inflammatory, and anti-apoptotic effects. It modulates p53, Bax, Bcl-2, and Caspase-3 in its anti-apoptotic activity. Geniposide has therapeutic potential for Parkinson's disease, acute lung injury, Alzheimer's disease, and metabolic disorders. The compound is a major iridoid found in fruit and is used in Asian traditional medicine.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H24O10
Molecular Weight
388.37
Exact Mass
388.136
CAS #
24512-63-8
PubChem CID
107848
Appearance
White to yellow solid powder
Density
1.5±0.1 g/cm3
Boiling Point
641.4±55.0 °C at 760 mmHg
Melting Point
161-162ºC
Flash Point
231.5±25.0 °C
Vapour Pressure
0.0±4.3 mmHg at 25°C
Index of Refraction
1.621
LogP
-1.92
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
6
Heavy Atom Count
27
Complexity
617
Defined Atom Stereocenter Count
8
SMILES
COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChi Key
IBFYXTRXDNAPMM-BVTMAQQCSA-N
InChi Code
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
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
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~257.49 mM)
H2O : ~50 mg/mL (~128.74 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.75 mg/mL (7.08 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.75 mg/mL (7.08 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.75 mg/mL (7.08 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 100 mg/mL (257.49 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.5749 mL 12.8743 mL 25.7486 mL
5 mM 0.5150 mL 2.5749 mL 5.1497 mL
10 mM 0.2575 mL 1.2874 mL 2.5749 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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