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Graveoline - CAS 485-61-0

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Category
ADCs
Product Name
Graveoline
Catalog Number
485-61-0
CAS Number
485-61-0
Description
Graveoline isolated from ethanolic extract of Ruta graveolens triggers apoptosis and autophagy in skin melanoma cells: a novel apoptosis-independent autophagic signaling pathway.
Molecular Weight
279.29
Molecular Formula
C17H13NO3
COA
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MSDS
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Structure
CAS 485-61-0 Graveoline
Specification
Purity
96 % (HPLC).
Melting Point
204-205 °C
Appearance
Solid Powder
Application
ADCs Cytotoxin
Storage
Store at +4 °C, in dark place.
Solubility
well in chloroform and hot alcohol.
Reference Reading
1.Graveoline isolated from ethanolic extract of Ruta graveolens triggers apoptosis and autophagy in skin melanoma cells: a novel apoptosis-independent autophagic signaling pathway.
Ghosh S1, Bishayee K, Khuda-Bukhsh AR. Phytother Res. 2014 Aug;28(8):1153-62. doi: 10.1002/ptr.5107. Epub 2013 Dec 17.
Anti-cancer drugs generally kill cancer cells by apoptosis but fail to do so when they become resistant and escape apoptosis signals. But these resistant cells can still be killed by autophagy. Therefore, drugs having both apoptotic and autophagic abilities are solicited in effective cancer management. In search of such a drug, we examined the efficacy of graveoline, a bioactive compound isolated from Ruta graveolens on skin melanoma A375 cells through the use of specific signaling cascades and their inhibitors. Cytotoxicity of graveoline was tested by conducting MTT assay. Induction of autophagy and apoptosis was checked. Expression of related proteins and their localization were studied by conducting immunoblot assay and through confocal microscopy, respectively. We found graveoline-induced Beclin-1 associated autophagy in A375 cells and 3-methyladenine, an inhibitor of autophagy did not affect apoptosis. Conversely, caspase inhibitor that blocked apoptosis did not affect autophagic cell death, suggesting thereby that these two were independent events.
2.Graveoline Analogs Exhibiting Selective Acetylcholinesterase Inhibitory Activity as Potential Lead Compounds for the Treatment of Alzheimer's Disease.
Li Z1, Mu C2,3, Wang B4, Jin J5. Molecules. 2016 Jan 22;21(2). pii: E132. doi: 10.3390/molecules21020132.
This study designed and synthesized a series of new graveoline analogs on the basis of the structural characteristics of acetylcholinesterase (AChE) dual-site inhibitors. The activity of these analogs was also evaluated. Results showed that the synthesized graveoline analogs displayed stronger inhibitory activity against AChE and higher selectivity than butyrylcholine esterase (BuChE) (Selectivity Index from 45 to 486). When the two sites in the graveoline parent ring substituting phenyl and amino terminal had six chemical bonds (n = 3) and the terminal amino was piperidine, compound 5c showed the best activity. Furthermore, the mechanism of action and binding mode were explored by enzyme kinetic simulation, molecular docking, and thioflavin T-based fluorometric assay. Cytotoxicity assay showed that the low concentration of the analogs did not affect the viability of the neurocyte SH-SY5Y.
3.Phytotoxins from the leaves of Ruta graveolens.
Hale AL1, Meepagala KM, Oliva A, Aliotta G, Duke SO. J Agric Food Chem. 2004 Jun 2;52(11):3345-9.
Bioassay-guided fractionation of the ethyl acetate extract of Ruta graveolens (common rue) leaves led to the isolation of the furanocoumarins 5-methoxypsoralen (5-MOP), 8-methoxypsoralen (8-MOP), and the quinolone alkaloid graveoline as phytotoxic constituents. Graveoline and 8-MOP substantially inhibited growth of Lactuca sativa (lettuce) seedlings and reduced chlorophyll content at 100 microM; this effect was not due to a direct effect on chlorophyll synthesis. Radical growth of L. sativa was inhibited by 10 microM 8-MOP. Graveoline inhibited growth of Lemna paucicostata (duckweed) at 100 microM. This is the first report of the phytotoxic activity of graveoline. Growth of Agrostis stolonifera (bentgrass) was inhibited by 5-MOP at 30 microM. All three compounds substantially reduced cell division in Allium cepa (onion) at or below 100 microM. None of the compounds caused significant cellular leakage of Cucumis sativus (cucumber) cotyledon disks at 100 microM.
4.Synthesis and evaluation of graveoline and graveolinine derivatives with potent anti-angiogenesis activities.
An ZY1, Yan YY, Peng D, Ou TM, Tan JH, Huang SL, An LK, Gu LQ, Huang ZS. Eur J Med Chem. 2010 Sep;45(9):3895-903. doi: 10.1016/j.ejmech.2010.05.043. Epub 2010 May 26.
A series of graveoline and graveolinine derivatives were synthesized. The biological results showed that most of graveoline derivatives possessed higher cytotoxicity and better inhibitive effect against the adhesion and migration of human umbilical vein endothelial cell (HUVEC) than graveolinine derivatives. Among these compounds, 8d was the most potent agents that also showed significant anti-angiogenesis activities in chick embryo chorioallantoic membrane (CAM) assay.
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