| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 100mg |
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| Targets |
Harpagoside exerts its anti-inflammatory and analgesic effects through multiple mechanisms. It has been reported to inhibit the production of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-α), interleukin-1β (IL-1β), and interleukin-6 (IL-6). Harpagoside also inhibits the activation of nuclear factor-kappa B (NF-κB), a key transcription factor in inflammatory signaling. Additionally, it modulates the arachidonic acid pathway by inhibiting cyclooxygenase-2 (COX-2) expression and activity.
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| ln Vitro |
In vitro, harpagoside demonstrates anti-inflammatory activity in various cellular models. It inhibits the production of pro-inflammatory cytokines such as TNF-α, IL-1β, and IL-6 in LPS-stimulated macrophages. The compound also reduces the expression of COX-2 and inducible nitric oxide synthase (iNOS) in inflammatory cells. Harpagoside has been shown to inhibit the activation of NF-κB and mitogen-activated protein kinases (MAPKs). It also exhibits antioxidant activity by scavenging free radicals and reducing oxidative stress in cultured cells.
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| ln Vivo |
In vivo, harpagoside has demonstrated anti-inflammatory and analgesic effects in animal models. In rodent models of acute inflammation (carrageenan-induced paw edema), harpagoside reduces paw swelling. In models of chronic inflammation, such as adjuvant-induced arthritis, the compound reduces joint inflammation and pain. Harpagoside also exhibits analgesic effects in models of nociceptive pain, such as the hot plate test and the acetic acid-induced writhing test. These effects are consistent with its traditional use in the treatment of inflammatory and painful conditions.
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| Enzyme Assay |
Cell-free biochemical assays for harpagoside typically involve measuring its effects on enzyme activities and receptor binding. The compound's ability to inhibit COX-2 activity can be assessed using enzymatic assays with purified enzyme and specific substrates. Its antioxidant activity can be measured by its ability to scavenge free radicals, such as DPPH or ABTS radicals. The compound's effects on NF-κB DNA binding activity can be assessed using electrophoretic mobility shift assays (EMSAs) or ELISA-based assays.
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| Cell Assay |
In vitro cellular assays for harpagoside use various cell types, including macrophages, chondrocytes, and synoviocytes. For anti-inflammatory studies, cells are stimulated with LPS or other inflammatory agents in the presence or absence of harpagoside. Pro-inflammatory cytokine levels are measured by ELISA. The expression of COX-2, iNOS, and other inflammatory mediators is assessed by Western blot or RT-PCR. NF-κB activation is evaluated by measuring the nuclear translocation of the p65 subunit or by reporter gene assays.
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| Animal Protocol |
In vivo animal studies for harpagoside typically use rodent models of inflammation and pain. In the carrageenan-induced paw edema model, rats are treated with harpagoside via oral or intraperitoneal administration, and paw volume is measured using a plethysmometer. In the adjuvant-induced arthritis model, rats are injected with Freund's complete adjuvant, and harpagoside is administered daily. Joint inflammation, pain, and histological changes are assessed. In analgesic studies, the hot plate test and acetic acid-induced writhing test are used to evaluate pain relief.
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| ADME/Pharmacokinetics |
Harpagoside has a molecular formula of C₂₄H₃₀O₁₁ and a molecular weight of 494.49. It is an iridoid glycoside with good solubility in water and polar organic solvents. The compound is the main active constituent of Harpagophytum procumbens and is used as a chemical marker for quality control of devil's claw extracts. Its oral bioavailability is moderate, and it is metabolized primarily by the liver. The compound has a relatively short half-life and is excreted in urine.
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| References | |
| Additional Infomation |
Harpagoside is a terpene glycoside. Harpagoside has been reported in Scrophularia ningpoensis, Verbena officinalis, and other organisms for which data are available. See also: Harpagophytum procumbens root (part); Harpagophytum zeyheri root (part).
Harpagoside is a bitter-tasting iridoid glycoside that is the main active constituent of devil's claw (Harpagophytum procumbens), a plant traditionally used for the treatment of inflammatory conditions and pain. The compound is used in research to study the mechanisms of inflammation and pain. It is also used as a reference standard for the quality control of herbal preparations containing devil's claw. Harpagoside is for research use only and not for human therapeutic use. Its anti-inflammatory and analgesic effects have been validated in various preclinical studies, supporting its traditional use. |
| Molecular Formula |
C24H30O11
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|---|---|
| Molecular Weight |
494.49
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| Exact Mass |
494.178
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| CAS # |
19210-12-9
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| PubChem CID |
5281542
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
720.7±60.0 °C at 760 mmHg
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| Melting Point |
120ºC (dec.)
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| Flash Point |
244.3±26.4 °C
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| Vapour Pressure |
0.0±2.4 mmHg at 25°C
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| Index of Refraction |
1.660
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| LogP |
-0.92
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
35
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| Complexity |
811
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| Defined Atom Stereocenter Count |
10
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| SMILES |
C[C@@]1(C[C@H]([C@]2([C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)OC(=O)/C=C/C4=CC=CC=C4
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| InChi Key |
KVRQGMOSZKPBNS-FMHLWDFHSA-N
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| InChi Code |
InChI=1S/C24H30O11/c1-23(35-16(27)8-7-13-5-3-2-4-6-13)11-15(26)24(31)9-10-32-22(20(23)24)34-21-19(30)18(29)17(28)14(12-25)33-21/h2-10,14-15,17-22,25-26,28-31H,11-12H2,1H3/b8-7+/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1
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| Chemical Name |
[(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate
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| Synonyms |
AC1NQYLY; Eharpagoside; SMR001233395
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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 : ~62.5 mg/mL (~126.39 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 6.25 mg/mL (12.64 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 62.5 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: ≥ 6.25 mg/mL (12.64 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 62.5 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0223 mL | 10.1114 mL | 20.2229 mL | |
| 5 mM | 0.4045 mL | 2.0223 mL | 4.0446 mL | |
| 10 mM | 0.2022 mL | 1.0111 mL | 2.0223 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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