Echinatine

For research use only. Not for therapeutic Use.

  • CAT Number: I026679
  • CAS Number: 480-83-1
  • Molecular Formula: C15H25NO5
  • Molecular Weight: 299.37
  • Purity: ≥95%
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Echinatine (Cat.No:I026679) is a natural alkaloid derived from the Echinacea plant. It possesses immunomodulatory properties and is often used in traditional medicine. Echinatine is believed to enhance immune function, boost resistance to infections, and reduce inflammation. Further research is underway to explore its potential therapeutic applications and mechanisms of action.


Catalog Number I026679
CAS Number 480-83-1
Synonyms

Echinatine; NSC 89937; NSC-89937; NSC89937

Molecular Formula C15H25NO5
Purity ≥95%
Target Plants
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
IUPAC Name Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (1S-(1-alpha,7(2R,3S),7a-alpha))-
InChI InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12-,13-,15+/m0/s1
InChIKey SFVVQRJOGUKCEG-GZCFXPHUSA-N
SMILES C=1([C@@H]2[N@@](CC1)CC[C@@H]2O)COC([C@@](C(C)C)([C@H](C)O)O)=O
Reference

1: Ke Z, Su Z, Zhang X, Cao Z, Ding Y, Cao L, Ding G, Wang Z, Liu H, Xiao W. Discovery of a potent angiotensin converting enzyme inhibitor via virtual screening. Bioorg Med Chem Lett. 2017 Aug 15;27(16):3688-3692. doi: 10.1016/j.bmcl.2017.07.016. Epub 2017 Jul 5. PubMed PMID: 28712707.
2: Ji S, Li Z, Song W, Wang Y, Liang W, Li K, Tang S, Wang Q, Qiao X, Zhou D, Yu S, Ye M. Bioactive Constituents of Glycyrrhiza uralensis (Licorice): Discovery of the Effective Components of a Traditional Herbal Medicine. J Nat Prod. 2016 Feb 26;79(2):281-92. doi: 10.1021/acs.jnatprod.5b00877. Epub 2016 Feb 3. PubMed PMID: 26841168.
3: Veríssimo CJ, D’Agostino SM, Pessoa FF, de Toledo LM, Santos IK. Length and density of filiform tongue papillae: differences between tick-susceptible and resistant cattle may affect tick loads. Parasit Vectors. 2015 Nov 16;8:594. doi: 10.1186/s13071-015-1196-4. PubMed PMID: 26573922; PubMed Central PMCID: PMC4647628.
4: Mudge EM, Jones AM, Brown PN. Quantification of pyrrolizidine alkaloids in North American plants and honey by LC-MS: single laboratory validation. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(12):2068-74. doi: 10.1080/19440049.2015.1099743. Epub 2015 Oct 20. PubMed PMID: 26482059.
5: Brown AW, Stegelmeier BL, Colegate SM, Gardner DR, Panter KE, Knoppel EL, Hall JO. The comparative toxicity of a reduced, crude comfrey (Symphytum officinale) alkaloid extract and the pure, comfrey-derived pyrrolizidine alkaloids, lycopsamine and intermedine in chicks (Gallus gallus domesticus). J Appl Toxicol. 2016 May;36(5):716-25. doi: 10.1002/jat.3205. Epub 2015 Jul 14. PubMed PMID: 26177929.
6: Janeš D, Kreft S. TLC densitometric method for screening of lycopsamine in comfrey root (Symphytum officinale L.) extracts using retrorsine as a reference compound. Acta Pharm. 2014 Dec;64(4):503-8. doi: 10.2478/acph-2014-0031. PubMed PMID: 25531790.
7: Appadurai P, Rathinasamy K. Indicine N-oxide binds to tubulin at a distinct site and inhibits the assembly of microtubules: a mechanism for its cytotoxic activity. Toxicol Lett. 2014 Feb 10;225(1):66-77. doi: 10.1016/j.toxlet.2013.11.030. Epub 2013 Dec 1. PubMed PMID: 24300171.
8: Yue XP, Chang TC, DeJarnette JM, Marshall CE, Lei CZ, Liu WS. Copy number variation of PRAMEY across breeds and its association with male fertility in Holstein sires. J Dairy Sci. 2013;96(12):8024-34. doi: 10.3168/jds.2013-7037. Epub 2013 Oct 11. PubMed PMID: 24119816.
9: Sodhi M, Mukesh M, Kishore A, Mishra BP, Kataria RS, Joshi BK. Novel polymorphisms in UTR and coding region of inducible heat shock protein 70.1 gene in tropically adapted Indian zebu cattle (Bos indicus) and riverine buffalo (Bubalus bubalis). Gene. 2013 Sep 25;527(2):606-15. doi: 10.1016/j.gene.2013.05.078. Epub 2013 Jun 19. PubMed PMID: 23792016.
10: Furusawa J, Funakoshi-Tago M, Mashino T, Tago K, Inoue H, Sonoda Y, Kasahara T. Glycyrrhiza inflata-derived chalcones, Licochalcone A, Licochalcone B and Licochalcone D, inhibit phosphorylation of NF-kappaB p65 in LPS signaling pathway. Int Immunopharmacol. 2009 Apr;9(4):499-507. PubMed PMID: 19291859.
11: Narberhaus I, Theuring C, Hartmann T, Dobler S. Uptake and metabolism of pyrrolizidine alkaloids in Longitarsus flea beetles (Coleoptera: Chrysomelidae) adapted and non-adapted to alkaloid-containing host plants. J Comp Physiol B. 2003 Aug;173(6):483-91. Epub 2003 Jun 12. PubMed PMID: 12802610.
12: Kim HY, Stermitz FR, Coulombe RA Jr. Pyrrolizidine alkaloid-induced DNA-protein cross-links. Carcinogenesis. 1995 Nov;16(11):2691-7. PubMed PMID: 7586188.
13: Kim HY, Stermitz FR, Molyneux RJ, Wilson DW, Taylor D, Coulombe RA Jr. Structural influences on pyrrolizidine alkaloid-induced cytopathology. Toxicol Appl Pharmacol. 1993 Sep;122(1):61-9. PubMed PMID: 8378933.
14: Miser JS, Smithson WA, Krivit W, Hughes CH, Davis D, Krailo MD, Hammond GD. Phase II trial of indicine N-oxide in relapsed acute leukemia of childhood. A report from the Childrens Cancer Study Group. Am J Clin Oncol. 1992 Apr;15(2):135-40. PubMed PMID: 1553901.
15: Miser JS, Smithson WA, Krivit W, Hughes C, Davis D, Krailo M, Hammond D. Phase II trial of indicine N-oxide in relapsed pediatric solid tumors. A report from the Childrens Cancer Study Group. Invest New Drugs. 1991 Nov;9(4):339-42. PubMed PMID: 1804809.
16: Whitehead VM, Bernstein ML, Vega R, Vats T, Dyment P, Vietti TJ, Krischer J. Phase I trial of indicine-N-oxide in children with leukemia and solid tumors: a Pediatric Oncology Group study. Cancer Chemother Pharmacol. 1990;26(5):377-9. PubMed PMID: 2208580.
17: Moore DJ, Batts KP, Zalkow LL, Fortune GT Jr, Powis G. Model systems for detecting the hepatic toxicity of pyrrolizidine alkaloids and pyrrolizidine alkaloid N-oxides. Toxicol Appl Pharmacol. 1989 Nov;101(2):271-84. PubMed PMID: 2815083.
18: Cragg G, Suffness M. Metabolism of plant-derived anticancer agents. Pharmacol Ther. 1988;37(3):425-61. Review. PubMed PMID: 3290912.
19: Anderson WK, Milowsky AS. 3-Pyrroline N-oxide bis(carbamate) tumor inhibitors as analogues of indicine N-oxide. J Med Chem. 1987 Nov;30(11):2144-7. PubMed PMID: 3669020.
20: King SA, Suffness M, Leyland-Jones B, Hoth DF, O’Dwyer PJ. Indicine N-oxide: clinical use of a pyrrolizidine alkaloid. Cancer Treat Rep. 1987 May;71(5):517-23. Review. PubMed PMID: 3552221. H

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