8-O-AcetylharpagideCAS# 6926-14-3 |
- 6-Epi-8-O-acetylharpagide
Catalog No.:BCN4550
CAS No.:97169-44-3
Quality Control & MSDS
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Chemical structure
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| Cas No. | 6926-14-3 | SDF | Download SDF |
| PubChem ID | 5459146 | Appearance | Powder |
| Formula | C17H26O11 | M.Wt | 406.4 |
| Type of Compound | Iridoids | Storage | Desiccate at -20°C |
| Synonyms | Harpagide 8-acetate | ||
| Solubility | Soluble in DMSO and methanol; insoluble in water | ||
| Chemical Name | [(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] acetate | ||
| SMILES | CC(=O)OC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)C | ||
| Standard InChIKey | CAFTUQNGDROXEZ-CDZVNVNZSA-N | ||
| 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 | 8-O-Acetylharpagide has anti-inflammatory, vasoconstrictor, antibacteria and antiviral activities, it also has a biological activity on isolated smooth muscle preparations from guinea pig. 8-O-Acetylharpagide presents the obvious inhibition on Epstein-Barr virus(EBV) infection, it not only apparently inhibits EBV-VCA,but also alleviates the hyperfunction and effusion of capillary permeability at the early inflammation. |
| Targets | Antifection |
| In vitro | Vasoconstrictor activity of 8-O-acetylharpagide from Ajuga reptans.[Pubmed: 1431938]J Nat Prod. 1992 Aug;55(8):1145-8.The traditional therapeutic indications for the use of Ajuga reptans (Labiatae) have been investigated. The H2O-soluble part of a crude and partially purified MeOH extract and two isolated iridoids (8-O-Acetylharpagide and harpagide), were tested for a biological activity on isolated smooth muscle preparations from guinea pig. 8-O-acetylharpagide is not an ecdysteroid agonist.[Pubmed: 11520686]Insect Biochem Mol Biol. 2001 Oct;31(11):1077-82.
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| In vivo | Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens extract in beagle dog.[Pubmed: 24066603]Zhongguo Zhong Yao Za Zhi. 2013 Jun;38(12):2015-8.8-O-Acetylharpagide and harpagide are two kinds of effective component of Ajuga decumbens extract. A sensitive LC-MS/MS method has been established for pharmacokinetics of 8-O-Acetylharpagide and harpagide in beagle dog after oral administration of from A. decumbens extract.
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| Animal Research | In Vivo and In Vitro Pharmacodynamics Study of 8-O-Acetylharpagide in the Prevention and Treatment of EB Viral Infection.[Reference: WebLink]World Journal of Integrated Traditional & Western Medicine, 2013, 8(4):351-4.To assess the pharmacodynamic effects of 8-O-Acetylharpagide in the prevention and treatment of Epstein-Barr virus(EBV)by in vivo and in vitro trial. |
8-O-Acetylharpagide Dilution Calculator
8-O-Acetylharpagide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.4606 mL | 12.3031 mL | 24.6063 mL | 49.2126 mL | 61.5157 mL |
| 5 mM | 0.4921 mL | 2.4606 mL | 4.9213 mL | 9.8425 mL | 12.3031 mL |
| 10 mM | 0.2461 mL | 1.2303 mL | 2.4606 mL | 4.9213 mL | 6.1516 mL |
| 50 mM | 0.0492 mL | 0.2461 mL | 0.4921 mL | 0.9843 mL | 1.2303 mL |
| 100 mM | 0.0246 mL | 0.123 mL | 0.2461 mL | 0.4921 mL | 0.6152 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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Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens Thunb extract in rats.[Pubmed:23545457]
J Ethnopharmacol. 2013 May 20;147(2):503-8.
ETHNOPHARMACOLOGICAL RELEVANCE: Ajuga decumbens Thunb is a medicinal plant native to China popularly used to treat chronic pelvic inflammation and hysteromyoma. Its main bioactive components are iridoid glycosides, such as 8-O-Acetylharpagide and harpagide that had presented antibacterial, anti-inflammatory, and antiviral activities. AIM OF THE STUDY: To establish a sensitive LC-MS/MS method and compare the pharmacokinetics of 8-O-Acetylharpagide and harpagide in rats after oral administration of their pure forms and from compounds obtained from Ajuga decumbens extract. MATERIALS AND METHODS: Rats received orally 15 mg/kg (equivalent of 6 mg/kg 8-O-Acetylharpagide and 1.5mg/kg harpagide), 30 mg/kg and 60 mg/kg of Ajuga decumbens Thunb extract and were compared to animals that received 12 mg/kg of 8-O-Acetylharpagide or 3mg/kg of harpagide p.o. Concentrations of 8-O-Acetylharpagide and harpagide in plasma were determined by LC-MS/MS method at different time points and all pharmacokinetic parameters were estimated by non-compartmental analysis. RESULTS: Results showed that the iridoid glycosides were quickly absorbed by oral route and showed a dose-dependence profile. Pharmacokinetic parameters of both glycosides were essentially the same except Tmax when dosed as the extract or pure forms. CONCLUSION: 8-O-Acetylharpagide was metabolized to harpagide, which affected the pharmacokinetic profiles of harpagide when dosed as the extract. This pharmacokinetic study seems to be useful for a further clinical study of Ajuga decumbens Thunb extract.
Vasoconstrictor activity of 8-O-acetylharpagide from Ajuga reptans.[Pubmed:1431938]
J Nat Prod. 1992 Aug;55(8):1145-8.
The traditional therapeutic indications for the use of Ajuga reptans (Labiatae) have been investigated. The H2O-soluble part of a crude and partially purified MeOH extract and two isolated iridoids (8-O-Acetylharpagide and harpagide), were tested for a biological activity on isolated smooth muscle preparations from guinea pig.
[Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens extract in beagle dog].[Pubmed:24066603]
Zhongguo Zhong Yao Za Zhi. 2013 Jun;38(12):2015-8.
8-O-Acetylharpagide and harpagide are two kinds of effective component of Ajuga decumbens extract. A sensitive LC-MS/MS method has been established for pharmacokinetics of 8-O-Acetylharpagide and harpagide in beagle dog after oral administration of from A. decumbens extract. Female beagle dogs received orally 12.9, 25.7 mg x kg(-1) p. o. Concentrations of 8-O-Acetylharpagide and harpagide in plasma were determined by LC-MS/MS method at different time points and all pharmacokinetic parameters were estimated by non-compartment analysis. The mobile phase consisted of 0.1% formic acid in water (A) and acetonitrile (B), which was run at a flow rate of 0.3 mL x min(-1). Chromatographic separation was achieved on an Agilent ZORBAX XDB-C18 column (2.1 mm x 50 mm, 3.5 microm) using a gradient elution of 5% B at 0-2 min, 95% B at 2. 1-5 min and 5% B at 5. 1-10 min. All analytes, including the IS, were monitored under positive ionization conditions and quantified in MRM mode with transitions of m/z 429.2-369.2 for 8-O-Acetylharpagide, m/z 387.2-207.2 for harpagide, and m/z 149.2-103.1 for IS. High purity nitrogen was employed as both the nebulizing and drying gas. Other parameters of the mass spectrometer were optimized as follows: drying gas flow 10.0 L x min(-1); drying gas temperature 300 degrees C; capillary voltage 4 000 V. Results showed that 8-O-Acetylharpagide and harpagide showed a dose-dependence profile. T(max) of 8-O-Acetylharpagide is 1.7 h, and T(max) of harpagide is 1.57 h, which was higher than T(max) of 8-O-Acetylharpagide and harpagide after oral administration of from A. decumbens extract in rats. The different pharmacokinetic parameters may be due to the species differences of rat and beagle dog.
8-O-acetylharpagide is not an ecdysteroid agonist.[Pubmed:11520686]
Insect Biochem Mol Biol. 2001 Oct;31(11):1077-82.
We have reinvestigated the activity of 8-O-Acetylharpagide, an iridoid glucoside, as an ecdysteroid agonist. Elbrecht et al. (Insect Biochem. Mol. Biol. 26 (1996) 519) isolated a preparation of this compound from Ajuga reptans L. and ascribed ecdysteroid agonist activity on the basis of the induction of an ecdysteroid-like response in Drosophila melanogaster KcO cells, the displacement of [3H]ponasterone A from the Drosophila receptor and the activation of an ecdysteroid-regulated gene in a transactivation assay. We provide evidence that the agonist activity derives from contaminating ecdysteroids; A. reptans is a species rich in ecdysteroids. Purified 8-O-Acetylharpagide is not active in the D. melanogaster B(II) cell bioassay, neither as an agonist nor as an antagonist, nor does it displace [3H]ponasterone A from dipteran or lepidopteran ecdysteroid receptor complexes.
