We Offer Worldwide Shipping
Login Wishlist

Shanzhiside methyl ester

$178

  • Brand : BIOFRON

  • Catalogue Number : BF-S1010

  • Specification : 98%

  • CAS number : 64421-28-9

  • Formula : C17H26O11

  • Molecular Weight : 406.38

  • PUBCHEM ID : 13892722

  • Volume : 20mg

In stock

Quantity
Checkout Bulk Order?

Catalogue Number

BF-S1010

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

406.38

Appearance

Lamiophlomis rotata (Benth.) Kudo.

Botanical Source

Angelica polymorpha,Notopterygium franchetii,Notopterygium incisum,Toddalia asiatica,Lamiophlomis rotata

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)O

Synonyms

Methyl (1S,4aS,5R,7S,7aS)-1-(β-D-glucopyranosyloxy)-5,7-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate/shanziside Me-ester/shanziside methyl ester/shanzhiside methy ester/Shanzhiside methylester/Shanzhiside methyl ester/hanzhiside Methyl ester/Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5,7-dihydroxy-7-methyl-, methyl ester, (1S,4aS,5R,7S,7aS)-/Shaniside methyl ester/shanzhiside Me ester

IUPAC Name

methyl (1S,4aS,5R,7S,7aS)-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

Density

1.6±0.1 g/cm3

Solubility

Methanol; Ethanol; Water

Flash Point

233.0±25.0 °C

Boiling Point

651.4±55.0 °C at 760 mmHg

Melting Point

90ºC (dec.)

InChl

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

InChl Key

KKSYAZCUYVRKML-QDXNKOLPSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:64421-28-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

27023158

Abstract

A rapid, sensitive and specific ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method for the quantification of shanzhiside methyl ester, 8-O-acetylshanzhiside methyl ester and luteolin-7-O-β-D-glucopyranoside of Lamiophlomis rotata Pill in rat plasma was developed and validated. After liquid-liquid extraction with n-butyl alcohol/ethyl acetate (70:30, v/v), analytes and paeoniflorin (internal standard, IS) were separated on an Acquity BEH UPLC C18 column (100 × 2.1 mm, 1.7 μm) with gradient elution at a flow rate of 0.2 mL/min. All calibration curves had good linearity (r>0.9929) over the concentration ranges of 1-1000 ng/mL for shanzhiside methyl ester and 8-O-acetylshanzhiside methyl ester, 0.3-150 ng/mL for luteolin-7-O-β-D-glucopyranoside. The intra- and inter-day precisions were all within 11.1% and the accuracy (relative error, RE%) all ranged from -13.6% to 5.3%. The method also guaranteed an acceptable selectivity, recovery and stability, which was successfully applied to a pharmacokinetic study of the three analytes in rats after oral administration of Lamiophlomis rotata Pill.

Copyright © 2016 Elsevier B.V. All rights reserved.

KEYWORDS

Lamiophlomis rotata pill; Pharmacokinetics; Rat plasma; UPLC-MS/MS

Title

Simultaneous determination of shanzhiside methyl ester, 8-O-acetylshan- zhiside methyl ester and luteolin-7-O-β-D-glucopyranoside in rat plasma by ultra performance liquid chromatography-tandem mass spectrometry and its application to a pharmacokinetic study after oral administration of Lamiophlomis rotata Pill.

Author

Chen J1, Wang Y1, Liang X1, Sun T1, Luo J1, Guo X1, Zhao L2.

Publish date

2016 May 1

PMID

31704416

Abstract

ETHNOPHARMACOLOGICAL RELEVANCE:
The aerial parts of Barleria prionitis Linn. (BP) (Acanthaceae) plant has long been used to treat inflammatory disorders such as toothache, swellings, arthritis and gout.

AIM OF THE STUDY:
The purpose of this study was to evaluate the effects of shanzhiside methyl ester (SME), 8-O-acetyl shanzhiside methyl ester (ASME) and iridoid glycosides rich monoterpenoidal fraction (IFBp), isolated from the aerial part of BP, on the pro-inflammatory mediators in stimulated rat neutrophils.

MATERIALS AND METHODS:
Rat neutrophils were incubated with or without test drugs. The influence of laboratory isolated and identified SME, ASME and IFBp on the production and release of pro-inflammatory mediators i.e. myeloperoxidase (MPO), elastase, matrix metalloproteinase-9 (MMP-9), interleukin 8 (IL-8), tumor necrosis factor alpha (TNF-α) and leukotriene B4 (LTB4) was evaluated in the formyl-met-leu-phenylalanine (f-MLP) and lipopolysaccharide (LPS) stimulated rat neutrophils using enzyme-linked immunosorbent assay (ELISA) methods. IFBp was also standardized with the high performance thin layer chromatography by simultaneous determination of SME and ASME marker compounds.

RESULTS:
SME, ASME and IFBp displayed concentration-dependent inhibitory effects on the MPO, elastase and MMP-9 enzymes release, and IL-8, TNF-α and LTB4 cytokines production in the f-MLP and LPS stimulated rat neutrophils. The content of SME and ASME was found to be 17.32 ± 1.98 and 11.30 ± 1.06% w/w, respectively, in IFBp by HPTLC method.

CONCLUSION:
Altogether, the present results suggest that the iridoidal glycosides of BP may be considered as therapeutic strategy against neutrophil-mediated inflammatory diseases. Developed and validated HPTLC method for the standardization of IFBp of BP can be used as a quality control tool for the routine qualitative and quantitative analysis of Barleria species containing SME and/or ASME.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Acetyl shanzhiside methyl ester; Barleria prionitis; Iridoid glycosides; Proinflammatory mediators; Shanzhiside methyl ester

Title

Inhibition of the pro-inflammatory mediators in rat neutrophils by shanzhiside methyl ester and its acetyl derivative isolated from Barleria prionitis.

Author

Ghule BV1, Kotagale NR2, Patil KS3.

Publish date

2020 Mar 1


Description :

Shanzhiside methylester, the principle effective iridoid glycoside from the analgesic herb Lamiophlomis rotata, reduces neuropathic pain by stimulating spinal microglial β-endorphin expression. PUMID/DOI: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. 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. 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.