HarpagideCAS# 6926-08-5 |
- 6-Epiharpagide
Catalog No.:BCN4563
CAS No.:86362-16-5
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 6926-08-5 | SDF | Download SDF |
| PubChem ID | 93045 | Appearance | Colorless-light yellow powder |
| Formula | C15H24O10 | M.Wt | 364.35 |
| Type of Compound | Iridoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in methanol and water | ||
| Chemical Name | (1S,4aS,5R,7S,7aR)-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-4a,5,7-triol | ||
| SMILES | CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)O | ||
| Standard InChIKey | XUWSHXDEJOOIND-YYDKPPGPSA-N | ||
| Standard InChI | InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3/t6-,7-,8-,9+,10-,11-,12+,13+,14+,15-/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. |
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| 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. |
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| 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. | ||
| Description | Harpagide has neuroprotective effect, it can obviously protect acute cerebral ischemia in mice,its therapeutical effects are approached to protecting the activity of brain mitochondria and decreasing protein expression level of caspase-3; harpagide also has a potential for prevention of bone loss in ovariectomized (OVX) mice by regulating the stimulation of osteoblast differentiation and the suppression of osteoclast formation. Harpagide may have anti-inflammatory efficacy. |
| Targets | TNF-α | NO | COX | Caspase | Calcium Channel | ATPase |
| In vitro | Effects of β-glucosidase hydrolyzed products of harpagide and harpagoside on cyclooxygenase-2 (COX-2) in vitro.[Pubmed: 21775152 ]Bioorg Med Chem. 2011 Aug 15;19(16):4882-6.Harpagide (1) and harpagoside (2) are two iridoid glycosides existing in many medicinal plants. Although they are believed to be the main bioactive compounds related to the anti-inflammatory efficacy of these plants, the mechanisms of their anti-inflammatory activities remain unclear. |
| In vivo | Neuro-protective effect of harpagide on acute cerebral ischemic injury in mice and its mechanism involving mitochondria.[Reference: WebLink]Journal of Chinese Pharmaceutical Sciences, 2015, 50(12):1026-31.To observe the neuro-protective effects of Harpagide on acute cerebral ischemic injury in mice and its mechanism involving mitochondria. |
| Cell Research | Protective effects of Harpagide and Harpagoside on human vascular endothelial cells injury induced by hydrogen peroxide.[Reference: WebLink]Medical Research & Education, 2009, 26(2):11-2.To investigate protective effects of Harpagide and Harpagoside on human vascular endothelial cells(HUVECS) injury induced by hydrogen peroxide(H2O2). |
| Animal Research | Anti-osteoporotic activity of harpagide by regulation of bone formation in osteoblast cell culture and ovariectomy-induced bone loss mouse models.[Pubmed: 26712566 ]J Ethnopharmacol. 2016 Feb 17;179:66-75.Harpagide, an iridoid glucoside, is a constituent of the root of Harpagophytum procumbens var. sublobatum (Engl.) Stapf, Devil's claw which has been used in patients with osteoarthritis (OA). In the present study, we investigated the anti-osteoporotic potential of Harpagide and its underlying mechanism of action in in vitro cell culture and in vivo bone loss animal models.
Harpagide was obtained from the alkalic hydrolysis of harpagoside, a major constituent of H. procumbens var. sublobatum Analysis of biomarkers for bone formation in osteoblastic MC3T3-E1 cells and bone resorption in osteoclast cells derived from mouse bone marrow cells was performed to evaluate the mechanism of action. |
Harpagide Dilution Calculator
Harpagide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7446 mL | 13.7231 mL | 27.4461 mL | 54.8923 mL | 68.6153 mL |
| 5 mM | 0.5489 mL | 2.7446 mL | 5.4892 mL | 10.9785 mL | 13.7231 mL |
| 10 mM | 0.2745 mL | 1.3723 mL | 2.7446 mL | 5.4892 mL | 6.8615 mL |
| 50 mM | 0.0549 mL | 0.2745 mL | 0.5489 mL | 1.0978 mL | 1.3723 mL |
| 100 mM | 0.0274 mL | 0.1372 mL | 0.2745 mL | 0.5489 mL | 0.6862 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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Anti-osteoporotic activity of harpagide by regulation of bone formation in osteoblast cell culture and ovariectomy-induced bone loss mouse models.[Pubmed:26712566]
J Ethnopharmacol. 2016 Feb 17;179:66-75.
ETHNOPHARMACOLOGICAL RELEVANCE: Harpagide, an iridoid glucoside, is a constituent of the root of Harpagophytum procumbens var. sublobatum (Engl.) Stapf, Devil's claw which has been used in patients with osteoarthritis (OA). In the present study, we investigated the anti-osteoporotic potential of Harpagide and its underlying mechanism of action in in vitro cell culture and in vivo bone loss animal models. MATERIAL AND METHODS: Harpagide was obtained from the alkalic hydrolysis of harpagoside, a major constituent of H. procumbens var. sublobatum Analysis of biomarkers for bone formation in osteoblastic MC3T3-E1 cells and bone resorption in osteoclast cells derived from mouse bone marrow cells was performed to evaluate the mechanism of action. The protective activity of Harpagide against bone loss was also evaluated in ovariectomized (OVX) mouse model. RESULTS: Harpagide improved bone properties by stimulating the process of differentiation and maturation of osteoblast cells and suppressing the process of RANKL-induced differentiation of osteoclast cells. In OVX-induced bone loss mouse model, oral administration of Harpagide significantly improved recovery of bone mineral density, trabecular bone volume, and trabecular number in the femur. Harpagide also prevented increase of trabecular separation and structure model index induced by OVX. Harpagide effectively inhibited the serum levels of biochemical markers of bone loss, including alkaline phosphatase, osteocalcin, C-terminal telopeptide, and tartrate-resistant acid phosphatase. CONCLUSION: Taken together, the present study demonstrates that Harpagide has a potential for prevention of bone loss in OVX mice by regulating the stimulation of osteoblast differentiation and the suppression of osteoclast formation. Therefore, these findings suggest that Harpagide might serve as a bioactive compound derived from H. procumbens var. sublobatum for improvement of age-dependent bone destruction disease.
Effects of beta-glucosidase hydrolyzed products of harpagide and harpagoside on cyclooxygenase-2 (COX-2) in vitro.[Pubmed:21775152]
Bioorg Med Chem. 2011 Aug 15;19(16):4882-6.
Harpagide (1) and harpagoside (2) are two iridoid glycosides existing in many medicinal plants. Although they are believed to be the main bioactive compounds related to the anti-inflammatory efficacy of these plants, the mechanisms of their anti-inflammatory activities remain unclear. The results of our present study showed that 1 and 2 had no effects on inhibitions of cyclooxygenase (COX)-1/2 enzyme activity, tumor necrosis factor-alpha (TNF-alpha) release, and nitric oxide (NO) production in vitro. However, the hydrolyzed products of 1 and 2 with beta-glucosidase treatment showed a significant inhibitory effect on COX-2 activity at 2.5-100 muM in a concentration-dependent manner. Our further study revealed that the hydrolyzed 2 product was structurally the same as the hydrolyzed 1 product (H-Harpagide (3)). The structure of 3 was 2-(formylmethyl)-2,3,5-trihydroxy-5-methylcyclopentane carbaldehyde, with a backbone similar to prostaglandins and COX-2 inhibitors such as celecoxib. All of them have a pentatomic ring with two adjacent side chains. The result of molecular modeling and docking study showed that 3 could bind to the COX-2 active domain well through hydrophobic and hydrogen-bonding interactions, whereas 1 and 2 could not, implying that the hydrolysis of the glycosidic bond of 1 and 2 is a pre-requisite step for their COX-2 inhibitory activity.
