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MedKoo Cat#: 564495 | Name: Echimidine

Description:

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

Echimidine is one of the natural predominant pyrrolizidine alkaloids (PAs) found in honeys produced in Australia and New Zealand. Echimidine activates PXR and induces PXR-mediated CYP3A4 expression.

Chemical Structure

Echimidine
Echimidine
CAS#520-68-3 (free)

Theoretical Analysis

MedKoo Cat#: 564495

Name: Echimidine

CAS#: 520-68-3 (free)

Chemical Formula: C20H31NO7

Exact Mass: 397.2101

Molecular Weight: 397.47

Elemental Analysis: C, 60.44; H, 7.86; N, 3.52; O, 28.18

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Related CAS #
520-68-3 (free) 41093-89-4 (N-oxide)
Synonym
Echimidine; (+)-Echimidine;
IUPAC/Chemical Name
(1S,7aS)-7-((((S)-2,3-dihydroxy-2-((S)-1-hydroxyethyl)-3-methylbutanoyl)oxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (E)-2-methylbut-2-enoate
InChi Key
HRSGCYGUWHGOPY-ZOSTXFCJSA-N
InChi Code
InChI=1S/C20H31NO7/c1-6-12(2)17(23)28-15-8-10-21-9-7-14(16(15)21)11-27-18(24)20(26,13(3)22)19(4,5)25/h6-7,13,15-16,22,25-26H,8-11H2,1-5H3/b12-6+/t13-,15-,16-,20+/m0/s1
SMILES Code
C/C=C(C(O[C@H]1CCN2CC=C([C@@H]12)COC([C@](C(C)(O)C)(O)[C@@H](O)C)=O)=O)\C
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 397.47 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
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Metabolic Pattern of Hepatotoxic Pyrrolizidine Alkaloids in Liver Cells. Chem Res Toxicol. 2021 Apr 19;34(4):1101-1113. doi: 10.1021/acs.chemrestox.0c00507. Epub 2021 Mar 10. PMID: 33719395. 5: Luckert C, Braeuning A, Lampen A, Hessel-Pras S. PXR: Structure-specific activation by hepatotoxic pyrrolizidine alkaloids. Chem Biol Interact. 2018 May 25;288:38-48. doi: 10.1016/j.cbi.2018.04.017. Epub 2018 Apr 14. PMID: 29665350. 6: Benamar H, Tomassini L, Venditti A, Marouf A, Bennaceur M, Serafini M, Nicoletti M. Acetylcholinesterase inhibitory activity of pyrrolizidine alkaloids from Echium confusum Coincy. Nat Prod Res. 2017 Jun;31(11):1277-1285. doi: 10.1080/14786419.2016.1242000. Epub 2016 Oct 16. PMID: 27748125. 7: Zan K, Wang Z, Hu XW, Li YL, Wang Y, Jin HY, Zuo TT, Ma SC. Pyrrolizidine alkaloids and health risk of three Boraginaceae used in TCM. Front Pharmacol. 2023 Mar 23;14:1075010. doi: 10.3389/fphar.2023.1075010. PMID: 37033649; PMCID: PMC10076571. 8: Hadi NSA, Bankoglu EE, Schott L, Leopoldsberger E, Ramge V, Kelber O, Sievers H, Stopper H. Genotoxicity of selected pyrrolizidine alkaloids in human hepatoma cell lines HepG2 and Huh6. Mutat Res Genet Toxicol Environ Mutagen. 2021 Jan- Feb;861-862:503305. doi: 10.1016/j.mrgentox.2020.503305. Epub 2020 Dec 28. PMID: 33551105. 9: Zhou SF, Xue CC, Yu XQ, Wang G. Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update. Curr Drug Metab. 2007 Aug;8(6):526-53. doi: 10.2174/138920007781368863. PMID: 17691916. 10: Luckert C, Hessel S, Lenze D, Lampen A. Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis. Toxicol In Vitro. 2015 Oct;29(7):1669-82. doi: 10.1016/j.tiv.2015.06.021. Epub 2015 Jun 20. PMID: 26100227. 11: Orantes-Bermejo FJ, Serra Bonvehí J, Gómez-Pajuelo A, Megías M, Torres C. Pyrrolizidine alkaloids: their occurrence in Spanish honey collected from purple viper's bugloss (Echium spp.). Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(10):1799-806. doi: 10.1080/19440049.2013.817686. Epub 2013 Jul 26. PMID: 23886433. 12: Ebmeyer J, Behrend J, Lorenz M, Günther G, Reif R, Hengstler JG, Braeuning A, Lampen A, Hessel-Pras S. Pyrrolizidine alkaloid-induced alterations of prostanoid synthesis in human endothelial cells. Chem Biol Interact. 2019 Jan 25;298:104-111. doi: 10.1016/j.cbi.2018.11.007. Epub 2018 Nov 19. PMID: 30465738. 13: Lucchetti MA, Glauser G, Kilchenmann V, Dübecke A, Beckh G, Praz C, Kast C. Pyrrolizidine Alkaloids from Echium vulgare in Honey Originate Primarily from Floral Nectar. J Agric Food Chem. 2016 Jun 29;64(25):5267-73. doi: 10.1021/acs.jafc.6b02320. Epub 2016 Jun 16. PMID: 27244472. 14: Oberlies NH, Kim NC, Brine DR, Collins BJ, Handy RW, Sparacino CM, Wani MC, Wall ME. Analysis of herbal teas made from the leaves of comfrey (Symphytum officinale): reduction of N-oxides results in order of magnitude increases in the measurable concentration of pyrrolizidine alkaloids. Public Health Nutr. 2004 Oct;7(7):919-24. doi: 10.1079/phn2004624. PMID: 15482618. 15: Mei N, Guo L, Fu PP, Fuscoe JC, Luan Y, Chen T. Metabolism, genotoxicity, and carcinogenicity of comfrey. J Toxicol Environ Health B Crit Rev. 2010 Oct;13(7-8):509-26. doi: 10.1080/10937404.2010.509013. PMID: 21170807; PMCID: PMC5894094. 16: Roncada P, Isani G, Peloso M, Dalmonte T, Bonan S, Caprai E. Pyrrolizidine Alkaloids from Monofloral and Multifloral Italian Honey. Int J Environ Res Public Health. 2023 Apr 5;20(7):5410. doi: 10.3390/ijerph20075410. PMID: 37048023; PMCID: PMC10094242. 17: Kempf M, Wittig M, Reinhard A, von der Ohe K, Blacquière T, Raezke KP, Michel R, Schreier P, Beuerle T. Pyrrolizidine alkaloids in honey: comparison of analytical methods. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2011 Mar;28(3):332-47. doi: 10.1080/19440049.2010.521772. Epub 2010 Nov 12. PMID: 21082464. 18: el-Shazly A, Abdel-All M, Tei A, Wink M. Pyrrolizidine alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae). Z Naturforsch C J Biosci. 1999 May-Jun;54(5-6):295-300. doi: 10.1515/znc-1999-5-601. PMID: 10431383. 19: Huybrechts B, Callebaut A. Pyrrolizidine alkaloids in food and feed on the Belgian market. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(11):1939-51. doi: 10.1080/19440049.2015.1086821. Epub 2015 Oct 15. PMID: 26373269. 20: Gao L, Rutz L, Schrenk D. Structure-dependent hepato-cytotoxic potencies of selected pyrrolizidine alkaloids in primary rat hepatocyte culture. Food Chem Toxicol. 2020 Jan;135:110923. doi: 10.1016/j.fct.2019.110923. Epub 2019 Oct 28. PMID: 31672516.