(-)-Eburnamonine - CAS 4880-88-0
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
(-)-Eburnamonine
Catalog Number:
4880-88-0
Synonyms:
Vinburnine; Vincamone; 1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine Eburnamenin-14(15H)-one Derivative;
CAS Number:
4880-88-0
Description:
(-)-Eburnamonine is a vinca alkaloid shows protective effects on mice.
Molecular Weight:
294.39
Molecular Formula:
C19H22N2O
Quantity:
Milligrams-Grams
Quality Standard:
Enterprise Standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=O)C2
InChI:
1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m1/s1
InChIKey:
WYJAPUKIYAZSEM-MOPGFXCFSA-N
Targets:
Others
Chemical Structure
CAS 4880-88-0 (-)-Eburnamonine

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Reference Reading


1.Anti-cholinergic alkaloids as potential therapeutic agents for Alzheimer's disease: an in silico approach.
Naaz H1, Singh S, Pandey VP, Singh P, Dwivedi UN. Indian J Biochem Biophys. 2013 Apr;50(2):120-5.
Alzheimer's disease (AD), a progressive neurodegenerative disorder with many cognitive and neuropsychiatric symptoms is biochemically characterized by a significant decrease in the brain neurotransmitter acetylcholine (ACh). Plant-derived metabolites, including alkaloids have been reported to possess neuroprotective properties and are considered to be safe, thus have potential for developing effective therapeutic molecules for neurological disorders, such as AD. Therefore, in the present study, thirteen plant-derived alkaloids, namely pleiocarpine, kopsinine, pleiocarpamine (from Pleiocarpa mutica, family: Annonaceae), oliveroline, noroliveroline, liridonine, isooncodine, polyfothine, darienine (from Polyalthia longifolia, family: Apocynaceae) and eburnamine, eburnamonine, eburnamenine and geissoschizol (from Hunteria zeylanica, family: Apocynaceae) were analyzed for their anti-cholinergic action through docking with acetylcholinesterase (AChE) as target.
2.Monoterpene indole alkaloids from the twigs of Kopsia arborea.
Cheenpracha S, Raksat A, Ritthiwigrom T, Laphookhieo S. Nat Prod Commun. 2014 Oct;9(10):1441-3.
The phytochemistry of Kopsia arborea Blume has received considerable attention, which has resulted in the isolation of a number of new unusual indole alkaloids with intriguing structures. In this study, a new eburnane-type alkaloid, phutdonginin (1), together with eight known alkaloids: 19-OH-(-)- eburnamonine (2), melodinine E (3), kopsinine (4), kopsilongine (5), kopsamine (6), (-)-methylenedioxy-1 1,12-kopsinaline (7), decarbomethoxykopsiline (8), and vincadifformine (9), were isolated from the twigs of K. arborea. Their structures were characterized extensively by 1D and 2D NMR spectroscopy and HR-ESI-MS. All compounds were submitted to TLC screening for acetylcholinesterase inhibitory activities. Only kopsamine and decarbomethoxykopsiline showed AChE inhibition with MIR values of 12.5 and 6.25 μg, respectively, compared with galanthamine (positive control, 0.004 μg). In addition, compounds 1 and 2 inhibited moderate antibacterial activity against E.
3.Exploiting the facile release of trifluoroacetate for the α-methylenation of the sterically hindered carbonyl groups on (+)-sclareolide and (-)-eburnamonine.
Riofski MV1, John JP, Zheng MM, Kirshner J, Colby DA. J Org Chem. 2011 May 20;76(10):3676-83. doi: 10.1021/jo102114f. Epub 2011 Apr 14.
An efficient method for the α-methylenation of carbonyl groups is reported, and this transformation is accomplished by a facile elimination of trifluoroacetate during the formation of the olefin. This method represents an improvement beyond existing protocol in cases of steric hindrance, and we have demonstrated the utility of the process across a series of ketones, lactams, and lactones. Additionally, we have applied this method to produce semisynthetic derivatives of the natural products (+)-sclareolide and (-)-eburnamonine, in which the carbonyl group is proximal to bulky functional groups. Mechanistic insight is also provided from a time course of (19)F NMR. Biological evaluation of the natural-product-derived enones led to the identification of a derivative of (-)-eburnamonine with significant cytotoxicity (LC(50) = 14.12 μM) in drug-resistant MDA-MB-231 breast cancer cells.
4.In vitro characterization of transport and metabolism of the alkaloids: vincamine, vinpocetine and eburnamonine.
Fandy TE1, Abdallah I2,3, Khayat M4, Colby DA5, Hassan HE6,7. Cancer Chemother Pharmacol. 2016 Feb;77(2):259-67. doi: 10.1007/s00280-015-2924-3. Epub 2015 Dec 14.
PURPOSE: Vincamine, vinpocetine and eburnamonine are alkaloids known for their neuroprotective attributes, enhancement of cerebrovascular blood flow and antitumor effect of their derivatives. However, the relative metabolic stability of these alkaloids and their extrusion by the drug efflux transporters expressed at the blood-brain barrier (BBB) are not clear. In this study, we developed rapid and sensitive methods for the detection of these alkaloids and investigated their relative metabolic stability and their interaction with drug efflux transporters.