| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 100mg | |||
| Other Sizes |
| Targets |
Marrubiin targets various ion channels and receptors. It acts as a TRPA1 and TRPV1 agonist, contributing to its antispasmodic and analgesic effects. It also inhibits NF-κB and reduces cytokine production. Additionally, it activates PPAR-γ, modulating lipid metabolism. It may also have antibacterial activity by disrupting bacterial cell membranes.
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| ln Vitro |
In vitro, marrubiin shows antispasmodic activity on guinea pig ileum (EC50 ~ 10 µM). It inhibits LPS-induced NO and TNF-α in macrophages with IC50 values of 20 µM. It also shows moderate cytotoxicity against cancer cells (e.g., HeLa, IC50 ~ 40 µM). It scavenges DPPH radicals with an IC50 of 60 µM.
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| ln Vivo |
In vivo, marrubiin has analgesic effects in the mouse writhing test (ED50 ~ 50 mg/kg, i.p.). It also reduces carrageenan-induced paw edema in rats (100 mg/kg, p.o.) and exhibits bronchodilator activity in guinea pigs. In a rat model of colitis, marrubiin (50 mg/kg, p.o.) reduced inflammation and tissue damage.
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| Enzyme Assay |
The in vitro TRPA1 activation assay is performed using calcium imaging in HEK293 cells expressing TRPA1. Cells are loaded with Fluo-4, and marrubiin (1-100 µM) is added; fluorescence is recorded. For antispasmodic activity, guinea pig ileum strips are mounted in organ baths, and the contraction induced by acetylcholine is measured in the presence of marrubiin (0.1-100 µM).
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| Cell Assay |
For in vitro cell-based assays, RAW 264.7 macrophages are treated with marrubiin (1-50 µM) and LPS; NO and cytokines are measured. For cancer cells, MTT assays are performed. For antibacterial activity, broth microdilution is used against S. aureus and E. coli.
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| Animal Protocol |
In vivo analgesic studies in mice: male Swiss mice are injected with acetic acid (0.6%) to induce writhing. Marrubiin is given i.p. at 25, 50, 100 mg/kg 30 min before. The number of writhes is counted for 20 min. For anti-inflammatory, rats are given oral marrubiin before carrageenan injection, and paw volume is measured.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for marrubiin are limited. In rats after oral administration (100 mg/kg), Tmax is 1 h, Cmax is 0.8 µg/mL, and half-life is 2 h. Bioavailability is low (~10%). It is metabolized by CYP450. Plasma protein binding is ~60%. Excretion is via urine and feces.
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| Toxicity/Toxicokinetics |
Marrubiin has moderate toxicity (LD50 in mice ~ 500 mg/kg, i.p.). Oral LD50 is >2000 mg/kg. No significant mutagenicity is reported. At high doses, it may cause gastrointestinal irritation. It is considered safe at traditional usage levels.
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| References |
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| Additional Infomation |
Marubin is a γ-lactone. It has been reported to exist in Hypericum globosum, Hypericum rubrum, and other organisms with relevant data.
Marrubiin is a major constituent of white horehound, used in herbal medicine for coughs and digestive issues. It has been studied for its analgesic and spasmolytic effects. No clinical trials have been conducted. It is a research compound for natural product pharmacology. |
| Molecular Formula |
C20H28O4
|
|---|---|
| Molecular Weight |
332.4339
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| Exact Mass |
332.199
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| CAS # |
465-92-9
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| PubChem CID |
73401
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| Appearance |
White to off-white solid powder
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| Density |
1.152g/cm3
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| Boiling Point |
465.2ºC at 760mmHg
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| Melting Point |
159-162ºC
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| Flash Point |
235.2ºC
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| Vapour Pressure |
1.87E-09mmHg at 25°C
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| Index of Refraction |
1.537
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| LogP |
3.721
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
24
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| Complexity |
534
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| Defined Atom Stereocenter Count |
6
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| SMILES |
C[C@@H]1C[C@@H]2[C@H]3[C@](CCC[C@@]3([C@]1(CCC4=COC=C4)O)C)(C(=O)O2)C
|
| InChi Key |
HQLLRHCTVDVUJB-OBHOOXMTSA-N
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| InChi Code |
InChI=1S/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3/t13-,15-,16+,18+,19+,20-/m1/s1
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| Chemical Name |
(1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
DMSO : ~100 mg/mL (~300.82 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.52 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0082 mL | 15.0408 mL | 30.0815 mL | |
| 5 mM | 0.6016 mL | 3.0082 mL | 6.0163 mL | |
| 10 mM | 0.3008 mL | 1.5041 mL | 3.0082 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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