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Shanzhiside methylester

CAS# 64421-28-9

Shanzhiside methylester

Catalog No. BCN4187----Order now to get a substantial discount!

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Quality Control of Shanzhiside methylester

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Chemical structure

Shanzhiside methylester

3D structure

Chemical Properties of Shanzhiside methylester

Cas No. 64421-28-9 SDF Download SDF
PubChem ID 3085296 Appearance White powder
Formula C17H26O11 M.Wt 406.4
Type of Compound Iridoids Storage Desiccate at -20°C
Solubility Soluble in methan
Chemical Name methyl (1S,5R,7S)-5,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
SMILES CC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)O
Standard InChIKey KKSYAZCUYVRKML-QDXNKOLPSA-N
Standard InChI InChI=1S/C17H26O11/c1-17(24)3-7(19)9-6(14(23)25-2)5-26-15(10(9)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5,7-13,15-16,18-22,24H,3-4H2,1-2H3/t7-,8-,9?,10?,11-,12+,13-,15+,16+,17+/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.
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.
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.

Source of Shanzhiside methylester

1 Lippia sp. 2 Phlomis sp.

Biological Activity of Shanzhiside methylester

DescriptionShanzhiside methylester reduces neuropathic pain by activating spinal GLP-1 receptors and subsequently stimulating microglial β-endorphin expression via the p38 MAPK signaling.
Targetsp38MAPK | GLP-1 receptor
In vivo

Shanzhiside methylester, the principle effective iridoid glycoside from the analgesic herb Lamiophlomis rotata, reduces neuropathic pain by stimulating spinal microglial β-endorphin expression.[Pubmed: 26363192 ]

Neuropharmacology. 2016 Feb;101:98-109

Lamiophlomis rotata (L. rotata, Duyiwei) is an orally available Tibetan analgesic herb widely prescribed in China. Shanzhiside methylester (SM) is a principle effective iridoid glycoside of L. rotata and serves as a small molecule glucagon-like peptide-1 (GLP-1) receptor agonist. This study aims to evaluate the signal mechanisms underlying SM anti-allodynia, determine the ability of SM to induce anti-allodynic tolerance, and illustrate the interactions between SM and morphine, or SM and β-endorphin, in anti-allodynia and anti-allodynic tolerance.
METHODS AND RESULTS:
Intrathecal SM exerted dose-dependent and long-lasting (>4 h) anti-allodynic effects in spinal nerve injury-induced neuropathic rats, with a maximal inhibition of 49% and a projected ED50 of 40.4 μg. SM and the peptidic GLP-1 receptor agonist exenatide treatments over 7 days did not induce self-tolerance to anti-allodynia or cross-tolerance to morphine or β-endorphin. In contrast, morphine and β-endorphin induced self-tolerance and cross-tolerance to SM and exenatide. In the spinal dorsal horn and primary microglia, SM significantly evoked β-endorphin expression, which was completely prevented by the microglial inhibitor minocycline and p38 mitogen-activated protein kinase (MAPK) inhibitor SB203580. SM anti-allodynia was totally inhibited by the GLP-1 receptor antagonist exendin(9-39), minocycline, β-endorphin antiserum, μ-opioid receptor antagonist CTAP, and SB203580. SM and exenatide specifically activated spinal p38 MAPK phosphorylation.
CONCLUSIONS:
These results indicate that SM reduces neuropathic pain by activating spinal GLP-1 receptors and subsequently stimulating microglial β-endorphin expression via the p38 MAPK signaling. Stimulation of the endogenous β-endorphin expression may be a novel and effective strategy for the discovery and development of analgesics for the long-term treatment of chronic pain.

Protocol of Shanzhiside methylester

Structure Identification
Biomed Chromatogr. 2012 Dec;26(12):1543-51.

Simultaneous determination of four shanzhiside methylester derivatives in rabbit plasma by liquid chromatography/tandem mass spectrometry.[Pubmed: 22422345]


METHODS AND RESULTS:
A simple and sensitive high-performance liquid chromatography/tandem mass spectrometry (LC/MS/MS) method was developed and validated for simultaneous determination of Shanzhiside methylester and its three derivatives in rabbit plasma. The method showed good linearity and no endogenous material interfered with the marked compounds and internal standard (IS) capatol peaks. Samples were processed by acetonitrile precipitation. Chromatography was performed using a C₁₈ column (150 × 3.9 mm i.d., 4 μm). The mobile phase consisted of methanol and water (60:40, v/v) during a total run time of 7 min. The main mass parent ions and daughter ions pairs (m/z) for monitoring were: Shanzhiside methylester, 429.0/267.4; 8-O-acetyl Shanzhiside methylester, 470.9/411.3; loganin, 413.2/251.4; phloyoside II, 479.2/281.3; and IS 385.2/203.3.
CONCLUSIONS:
Finally, the method was applied to a pharmacokinetic study of rabbits following intravenous administration of iridoid glycosides extracted from traditional herb Lamiophlomis rotata.

Shanzhiside methylester Dilution Calculator

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Shanzhiside methylester Molarity Calculator

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Preparing Stock Solutions of Shanzhiside methylester

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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References on Shanzhiside methylester

Simultaneous determination of four shanzhiside methylester derivatives in rabbit plasma by liquid chromatography/tandem mass spectrometry.[Pubmed:22422345]

Biomed Chromatogr. 2012 Dec;26(12):1543-51.

A simple and sensitive high-performance liquid chromatography/tandem mass spectrometry (LC/MS/MS) method was developed and validated for simultaneous determination of Shanzhiside methylester and its three derivatives in rabbit plasma. The method showed good linearity and no endogenous material interfered with the marked compounds and internal standard (IS) capatol peaks. Samples were processed by acetonitrile precipitation. Chromatography was performed using a C(1)(8) column (150 x 3.9 mm i.d., 4 microm). The mobile phase consisted of methanol and water (60:40, v/v) during a total run time of 7 min. The main mass parent ions and daughter ions pairs (m/z) for monitoring were: Shanzhiside methylester, 429.0/267.4; 8-O-acetyl Shanzhiside methylester, 470.9/411.3; loganin, 413.2/251.4; phloyoside II, 479.2/281.3; and IS 385.2/203.3. Finally, the method was applied to a pharmacokinetic study of rabbits following intravenous administration of iridoid glycosides extracted from traditional herb Lamiophlomis rotata.

Shanzhiside methylester, the principle effective iridoid glycoside from the analgesic herb Lamiophlomis rotata, reduces neuropathic pain by stimulating spinal microglial beta-endorphin expression.[Pubmed:26363192]

Neuropharmacology. 2016 Feb;101:98-109.

Lamiophlomis rotata (L. rotata, Duyiwei) is an orally available Tibetan analgesic herb widely prescribed in China. Shanzhiside methylester (SM) is a principle effective iridoid glycoside of L. rotata and serves as a small molecule glucagon-like peptide-1 (GLP-1) receptor agonist. This study aims to evaluate the signal mechanisms underlying SM anti-allodynia, determine the ability of SM to induce anti-allodynic tolerance, and illustrate the interactions between SM and morphine, or SM and beta-endorphin, in anti-allodynia and anti-allodynic tolerance. Intrathecal SM exerted dose-dependent and long-lasting (>4 h) anti-allodynic effects in spinal nerve injury-induced neuropathic rats, with a maximal inhibition of 49% and a projected ED50 of 40.4 mug. SM and the peptidic GLP-1 receptor agonist exenatide treatments over 7 days did not induce self-tolerance to anti-allodynia or cross-tolerance to morphine or beta-endorphin. In contrast, morphine and beta-endorphin induced self-tolerance and cross-tolerance to SM and exenatide. In the spinal dorsal horn and primary microglia, SM significantly evoked beta-endorphin expression, which was completely prevented by the microglial inhibitor minocycline and p38 mitogen-activated protein kinase (MAPK) inhibitor SB203580. SM anti-allodynia was totally inhibited by the GLP-1 receptor antagonist exendin(9-39), minocycline, beta-endorphin antiserum, mu-opioid receptor antagonist CTAP, and SB203580. SM and exenatide specifically activated spinal p38 MAPK phosphorylation. These results indicate that SM reduces neuropathic pain by activating spinal GLP-1 receptors and subsequently stimulating microglial beta-endorphin expression via the p38 MAPK signaling. Stimulation of the endogenous beta-endorphin expression may be a novel and effective strategy for the discovery and development of analgesics for the long-term treatment of chronic pain.

Description

Shanzhiside methy lester is isolated from L. rotata. Shanzhiside methyl ester is a small molecule glucagon-like peptide-1 (GLP-1) receptor agonist and has the ability to induce anti-allodynic tolerance.

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