| Size | Price | Stock | Qty |
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| 10mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg | |||
| Other Sizes |
| Targets |
Monotropein inhibits the expression of inflammatory mediators via NF-κB inactivation. It also modulates the mitogen-activated protein kinase (MAPK) signaling pathway and activates the Nrf2/HO-1 pathway while inhibiting NF-κB signaling. The compound exerts anti-apoptotic and anti-catabolic activity in chondrocytes and has antinociceptive action.
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| ln Vitro |
In vitro, monotropein exerts anti-apoptosis and anti-catabolic activity in chondrocytes. It protects against IL-1β-induced apoptosis and catabolic responses in osteoarthritis chondrocytes. The compound inhibits the expression of inflammatory mediators and has antioxidant properties. It also stimulates osteoblastic bone formation.
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| ln Vivo |
In vivo, monotropein has anti-inflammatory effects due to its ability to inhibit the expression of inflammatory mediators via NF-κB inactivation. It alleviates cisplatin-induced acute kidney injury by inhibiting oxidative damage, inflammation, and apoptosis through activation of Nrf2/HO-1 pathway and inhibition of NF-κB signaling. The compound increases osteoblastic bone formation and prevents bone loss in ovariectomized mice. It also inhibits inflammatory mediators in DSS-induced colitis mouse models.
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| Enzyme Assay |
For in vitro enzyme/receptor binding assays, monotropein can be evaluated for its effects on NF-κB signaling. Cell-free assays can be used to assess NF-κB DNA binding activity using electrophoretic mobility shift assays or ELISA-based kits. The compound is incubated with nuclear extracts and labeled NF-κB consensus oligonucleotides, and binding is quantified.
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| Cell Assay |
For in vitro cell-based assays, monotropein is typically tested on chondrocytes or osteoblasts. Cells are treated with the compound at various concentrations (typically 1-100 μM) in the presence or absence of inflammatory stimuli (such as IL-1β). Apoptosis is assessed by flow cytometry or TUNEL staining. Inflammatory mediator expression is measured by ELISA or qPCR. Osteogenic differentiation is assessed by alkaline phosphatase staining and mineralization assays.
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| Animal Protocol |
For in vivo animal experiments, monotropein is typically administered orally or intraperitoneally to mouse models of colitis (DSS-induced), osteoarthritis, or osteoporosis (ovariectomized mice). In colitis models, disease activity index, colon length, and histological scores are assessed. In osteoporosis models, bone mineral density and microarchitecture are assessed by micro-CT. Inflammatory markers and signaling pathway proteins are measured in tissues.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for monotropein are limited. As an iridoid glycoside with a molecular weight of 390.34 g/mol, it is expected to have moderate oral bioavailability. The compound may undergo metabolism in the gastrointestinal tract and liver. Standard pharmacokinetic studies would be required to determine its absorption, distribution, metabolism, and excretion profile.
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| Toxicity/Toxicokinetics |
Toxicological data for monotropein are limited. As a natural product isolate, it is generally considered to have low toxicity at pharmacological doses. However, comprehensive toxicological studies have not been extensively reported. The compound is classified as a research-grade reagent and is not for human use.
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| References | |
| Additional Infomation |
Monotropein glycosides are a class of iridoid monoterpenes with the structure 1,4a,7,7a-tetrahydrocyclopentano[c]pyran, substituted at position 1 with a β-D-glucopyranoyl group, position 4 with a carboxylic acid group, and position 7 with a hydroxyl and hydroxymethyl group, respectively (1S,4aS,7R,7aS diastereomers). They possess metabolites and anti-inflammatory activity. They are a cyclopentanopyran, monocarboxylic acid, iridoid monoterpene, β-D-glucoside, and monosaccharide derivative. Monotropein glycosides have been reported to exist in Galium rivale, Pyrola japonica, and several other organisms with relevant data. See also: Galium aparine (whole plant, part).
Monotropein is a research-use only compound and has not been approved for clinical applications. The compound is an iridoid glycoside, cyclopentanopyran, monocarboxylic acid, iridoid monoterpene, β-D-glucoside, and monosaccharide derivative. It is isolated from Morinda officinalis and Pyrola incarnata. Its molecular weight is 390.34. It is available from various research chemical suppliers. |
| Molecular Formula |
C16H22O11
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|---|---|
| Molecular Weight |
390.3393
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| Exact Mass |
390.116
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| Elemental Analysis |
C, 49.23; H, 5.68; O, 45.09
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| CAS # |
5945-50-6
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| Related CAS # |
Monotropein; 5945-50-6
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| PubChem CID |
73466
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| Appearance |
Off-white to yellow solid powder
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
717.6±60.0 °C at 760 mmHg
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| Flash Point |
262.0±26.4 °C
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| Vapour Pressure |
0.0±5.2 mmHg at 25°C
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| Index of Refraction |
1.686
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| Source |
Originated from plants: Pyrolaceae Pyrola calliantha H. Andr.
Originated from plants: Rubiaceae Morinda officinalis How |
| LogP |
-4.43
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
27
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| Complexity |
634
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| Defined Atom Stereocenter Count |
9
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| SMILES |
O([C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])[C@@]1([H])[C@@]2([H])[C@@]([H])(C(C(=O)O[H])=C([H])O1)C([H])=C([H])[C@@]2(C([H])([H])O[H])O[H]
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| InChi Key |
HPWWQPXTUDMRBI-NJPMDSMTSA-N
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| InChi Code |
InChI=1S/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23)/t6-,8-,9-,10-,11+,12-,14+,15+,16+/m1/s1
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| Chemical Name |
(1S,4aS,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid
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| Synonyms |
NSC 88926; NSC 291303; Monotropein
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
H2O : ~31.25 mg/mL (~80.06 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5619 mL | 12.8093 mL | 25.6187 mL | |
| 5 mM | 0.5124 mL | 2.5619 mL | 5.1237 mL | |
| 10 mM | 0.2562 mL | 1.2809 mL | 2.5619 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.
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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