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MedKoo Cat#: 465299 | Name: Shanzhiside methyl ester
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Shanzhiside methyl ester is an iridoid glycoside that has been found in L. rotata and has anti-inflammatory and antinociceptive activities. It is a glucagon-like peptide 1 receptor (GLP-1R) agonist.1 Shanzhiside methyl ester (10 µM) inhibits the release of myeloperoxidase (MPO) and elastase from isolated rat neutrophils activated by N-Formyl-Met-Leu-Phe (fMLF). It also inhibits LPS-induced increases in the release of IL-8 and leukotriene B4 (LTB4) from isolated rat neutrophils when used at a concentration of 10 µM. Shanzhiside methyl ester reduces L5/L6 spinal nerve ligation-induced mechanical allodynia in rats (ED50 = 40.4 µg/animal), an effect that can be reversed by the GLP-1R antagonist exendin (9-39).

Chemical Structure

Shanzhiside methyl ester
Shanzhiside methyl ester
CAS#64421-28-9

Theoretical Analysis

MedKoo Cat#: 465299

Name: Shanzhiside methyl ester

CAS#: 64421-28-9

Chemical Formula: C17H26O11

Exact Mass: 406.1475

Molecular Weight: 406.38

Elemental Analysis: C, 50.24; H, 6.45; O, 43.31

Price and Availability

Size Price Availability Quantity
1mg USD 250.00 2 Weeks
5mg USD 500.00 2 Weeks
10mg USD 750.00 2 Weeks
25mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Shanzhiside methyl ester;
IUPAC/Chemical Name
methyl (1S,4aS,5R,7S,7aS)-5,7-dihydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
InChi Key
KKSYAZCUYVRKML-IRDZEPHTSA-N
InChi Code
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
SMILES Code
COC(C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@]3([C@@]1([C@H](O)C[C@]3(C)O)[H])[H])=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Solvent mg/mL mM comments
Solubility
DMF 30.0 73.82
DMSO 30.0 73.82
Ethanol 30.0 73.82
PBS (pH 7.2) 10.0 24.61
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 406.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Xia MY, Wang Y, Zheng YH, Song YN, Liu TL, Zhang C. [Quality changes of Gardeniae Fructus Praeparatus processed by different frying methods: a color- component correlation analysis]. Zhongguo Zhong Yao Za Zhi. 2021 May;46(9):2197-2206. Chinese. doi: 10.19540/j.cnki.cjcmm.20210220.303. PMID: 34047121. 2: Zhang C, Liu C, Qu Y, Cao Y, Liu R, Sun Y, Nyima T, Zhang S, Sun Y. LC-MS- Based Qualitative Analysis and Pharmacokinetic Integration Network Pharmacology Strategy Reveals the Mechanism of Phlomis brevidentata H.W.Li Treatment of Pneumonia. ACS Omega. 2021 Feb 1;6(6):4495-4505. doi: 10.1021/acsomega.0c06201. PMID: 33623855; PMCID: PMC7893793. 3: Zhao X, Jiang S, Dong Q, Dang J, Liu Z, Han H, Tao Y, Yue H. Anti-rheumatoid arthritis effects of iridoid glucosides from Lamiophlomis rotata (Benth.) kudo on adjuvant-induced arthritis in rats by OPG/RANKL/NF-κB signaling pathways. J Ethnopharmacol. 2021 Feb 10;266:113402. doi: 10.1016/j.jep.2020.113402. Epub 2020 Sep 24. PMID: 32980481. 4: Thu VK, Bach NX, Dung CT, Cuong NT, Quang TH, Kim YC, Oh H, Kiem PV. Iridoids and cycloartane saponins from mussaenda pilosissima valeton and their inhibitory NO production in BV2 cells. Nat Prod Res. 2020 Mar 9:1-7. doi: 10.1080/14786419.2020.1737059. Epub ahead of print. PMID: 32146842. 5: Ghule BV, Kotagale NR, Patil KS. Inhibition of the pro-inflammatory mediators in rat neutrophils by shanzhiside methyl ester and its acetyl derivative isolated from Barleria prionitis. J Ethnopharmacol. 2020 Mar 1;249:112374. doi: 10.1016/j.jep.2019.112374. Epub 2019 Nov 5. PMID: 31704416. 6: Kayangar M, Ngansop Nono R, Kühlborn J, Tchuenguem R, Ponou BK, Jenett-Siems K, Teponno RB, Dzoyem JP, Opatz T, Melzig MF, Tapondjou LA. A new ursane-type triterpene oxoglucopyranoside from Crossopteryx febrifuga. Z Naturforsch C J Biosci. 2019 Nov 26;74(11-12):289-293. doi: 10.1515/znc-2019-0113. PMID: 31525160. 7: Wang H, Li J, Gao XM, Chang YX. Ionic liquid vortex-simplified matrix solid- phase dispersion for the simultaneous determination of terpenoids, crocins, quinic acid derivatives and flavonoids in Gardeniae fructus by UHPLC. J Sep Sci. 2019 May;42(10):1886-1895. doi: 10.1002/jssc.201801354. Epub 2019 Mar 19. PMID: 30828980. 8: Shan MQ, Wang TJ, Jiang YL, Yu S, Yan H, Zhang L, Wu QN, Geng T, Huang WZ, Wang ZZ, Xiao W. Comparative analysis of sixteen active compounds and antioxidant and anti-influenza properties of Gardenia jasminoides fruits at different times and application to the determination of the appropriate harvest period with hierarchical cluster analysis. J Ethnopharmacol. 2019 Apr 6;233:169-178. doi: 10.1016/j.jep.2019.01.004. Epub 2019 Jan 9. PMID: 30639058. 9: Czerwińska ME, Świerczewska A, Granica S. Bioactive Constituents of Lamium album L. as Inhibitors of Cytokine Secretion in Human Neutrophils. Molecules. 2018 Oct 25;23(11):2770. doi: 10.3390/molecules23112770. PMID: 30366450; PMCID: PMC6278331. 10: Fuji Y, Uchida A, Fukahori K, Chino M, Ohtsuki T, Matsufuji H. Chemical characterization and biological activity in young sesame leaves (Sesamum indicum L.) and changes in iridoid and polyphenol content at different growth stages. PLoS One. 2018 Mar 27;13(3):e0194449. doi: 10.1371/journal.pone.0194449. PMID: 29584748; PMCID: PMC5870955. 11: Senger DR, Hoang MV, Kim KH, Li C, Cao S. Anti-inflammatory activity of Barleria lupulina: Identification of active compounds that activate the Nrf2 cell defense pathway, organize cortical actin, reduce stress fibers, and improve cell junctions in microvascular endothelial cells. J Ethnopharmacol. 2016 Dec 4;193:397-407. doi: 10.1016/j.jep.2016.09.017. Epub 2016 Sep 20. PMID: 27660013; PMCID: PMC5436582. 12: Fan PC, Ma HP, Hao Y, He XR, Sun AJ, Jiang W, Li MX, Jing LL, He L, Ma J, Jia ZP. A new anti-fibrinolytic hemostatic compound 8-O-acetyl shanzhiside methylester extracted from Lamiophlomis rotata. J Ethnopharmacol. 2016 Jul 1;187:232-8. doi: 10.1016/j.jep.2016.04.016. Epub 2016 Apr 13. PMID: 27085939. 13: Chen J, Wang Y, Liang X, Sun T, Luo J, Guo X, Zhao L. 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. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 1;1020:62-6. doi: 10.1016/j.jchromb.2016.03.021. Epub 2016 Mar 19. PMID: 27023158. 14: Wu S, Jin Y, Liu QA, Wu JX, Bi YA, Wang ZZ, Xiao W. Acousto-optic tunable filter near-infrared spectroscopy for in-line monitoring liquid-liquid extraction of Gardenia jasminoides Ellis based on statistical analysis. Pharmazie. 2015 Oct;70(10):640-5. PMID: 26601419. 15: Chen J, Wang Y, Sun G, Ma Y, Guo X. Multi-components determination by single reference standard and HPLC fingerprint analysis for Lamiophlomis rotata Pill. Nat Prod Res. 2016 Jul;30(13):1561-4. doi: 10.1080/14786419.2015.1113530. Epub 2015 Nov 23. PMID: 26595778. 16: Zhong SH, Gu R, Wang LX, Liao YF, Zheng XH, Zheng X, Cao Y. [Simultaneous determination of seven constituents in Lamiophlomis rotata by HPLC]. Zhongguo Zhong Yao Za Zhi. 2014 Nov;39(22):4373-8. Chinese. PMID: 25850270. 17: Zeng R, Hu H, Ren G, Liu H, Qu Y, Hua W, Wang Z. Chemical Profiling Assisted Quality Assessment of Gentianae macrophyllae by High-Performance Liquid Chromatography Using a Fused-Core Column. J Chromatogr Sci. 2015 Sep;53(8):1274-9. doi: 10.1093/chromsci/bmu227. Epub 2015 Feb 2. PMID: 25650276. 18: Tao R, Li MX, Zhang QL, Qiu JG, Zhang JH, Jia ZP. [Isolation and identification of nine iridoid glycosides from Lamiophlomis rotata by HPLC combining PDA and MS]. Zhong Yao Cai. 2014 Mar;37(3):439-42. Chinese. PMID: 25174110. 19: Zhang L, Kan ZC, Zhang XL, Fang H, Jiang WL. 8-O-acetyl shanzhiside methylester attenuates cerebral ischaemia/reperfusion injury through an anti- inflammatory mechanism in diabetic rats. Basic Clin Pharmacol Toxicol. 2014 Dec;115(6):481-7. doi: 10.1111/bcpt.12266. Epub 2014 Jun 10. PMID: 24823762. 20: Xu L, Li YR, Li C, Lin LM, Wang ZM, Luo YM. [Chemical constituents from whole plants of Aconitum tanguticum]. Zhongguo Zhong Yao Za Zhi. 2013 Sep;38(17):2818-25. Chinese. PMID: 24380304.