| Description: |
Methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone9 is an antagonist of angiotensin II receptor (IC50=48.2 μM). Methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone9 is a quinolone alkaloid from Evodia rutaecarpa.1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone is an MAO-B inhibitor.1-Methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone exhibits potent anti-Helicobacter pylori activity with a minimum inhibitory concentration (MIC) value of 10-20 μg/ml. 1-Methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone exhibits dose-dependent DGAT inhibition with IC 50 of 13.5 μ. |
| In vitro: |
| Phyotherapy Resarch, VOL. 12, 212–214 (1998). | | Inhibition of Angiotensin II Receptor Binding by Quinolone Alkaloids from Evodia rutaecarpa. [Reference: WebLink] | | The renin–angiotensin system (RAS) is recognized as a key factor in blood pressure regulation and electrolyte homeostasis (Smith et al., 1992). The RAS constitutes a proteolytic cascade in which angiotensinogen from the liver is cleaved by the renin to produce a decapeptide,angiotensin I. Angiotensin I is converted to the octapeptide, angiotensin II (ang II) by angiotensin converting enzyme (ACE). Angiotensin II, the active hormone of the RAS, is a powerful arterial vasoconstrictor that exerts its action by interacting with specific receptors located on the cell membranes of various target organs (Smith et al., 1992; Valloton, 1987). Despite the fact that inhibition of ACE represents a prevalent class of therapeutics for hypertension and congestive heart failure ACE is a
nonspecific protease which is also responsible for the degradation of bradykinin as well as peptides such as substance P and enkephalins (Erdoes and Skidgel, 1986; Skidgel and Erdoes, 1987). Therefore, selective antagonism of ang II receptor may allow more precise therapeutic intervention. In this paper, we report the isolation of the active principle and the inhibitory effect on angiotensin II
receptor binding of quinolone alkaloids from Evodia rutaecarpa. | | Arch Pharm Res . 2007 Apr;30(4):397-401. | | Quinolone alkaloids from evodiae fructus and their inhibitory effects on monoamine oxidase[Pubmed: 17489352] | | 1-Methyl-2-undecyl-4(1H)-quinolone (1) was previously isolated as a selective MAO-B inhibitor from the Evodiae Fructus. Further bioassay-guided purification led to the identification of five known quinolone alkaloids, 1-methyl-2-nonyl-4(1H)-quinolone (2), 1-methyl-2-[(Z)-6-undecenyl]-4(1H)-quinolone (3), evocarpine (4), 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone (5), and dihydroevocarpine (6). All the isolates showed more potent inhibitory effects against MAO-B compared to MAO-A. The most MAO-B selective compound 5 among the isolates inhibited MAO-B in a competitive manner, according to kinetic analyses by Lineweaver-Burk reciprocal plots. | | Biol Pharm Bull . 1999 Oct;22(10):1141-1143. | | Anti-Helicobacter pylori activity of quinolone alkaloids from Evodiae fructus[Pubmed: 10549874] | | A biologically monitored fractionation of methanol extract of the fruit of Evodia rutaecarpa led to the isolation of six quinolone alkaloids, evocarpine (1), 1-methyl-2-[(4Z,7Z)-4,7-tridecadienyl]-4(1H)-quinolone (2), 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolo ne (3), 1-methyl-2-undecyl-4(1H)-quinolone (4), dihydroevocarpine (5), 1-methyl-2-pentadecyl-4(1H)-quinolone (6). They showed potent anti-Helicobacter pylori activity with the minimum inhibitory concentration (MIC) value of 10-20 microg/ml. However, they had no effect on Helicobacter pylori urease activity at the concentration of 300 microg/ml. | | Planta Med . 2002 Dec;68(12):1131-1133. | | Quinolone alkaloids, diacylglycerol acyltransferase inhibitors from the fruits of Evodia rutaecarpa[Pubmed: 12494344] | | From the diacylglycerol acyltransferase (DGAT) activity-guided fractionation, a new quinolone alkaloid, 1-methyl-2-tetradecyl-4(1H)-quinolone (1) was isolated from the fruits of Evodia rutaecarpa together with three known quinolone alkaloids, evocarpine (2), 1-methyl-2-[(4 Z,7 Z)-4,7-decadienyl]-4(1H)-quinolone (3) and 1-methyl-2-[(6 Z,9 Z)-6,9-pentadecadienyl]-4(1 H)-quinolone (4). They showed a dose-dependent DGAT inhibition with IC 50 values of 69.5 microM ( 1), 23.8 microM (2), 20.1 microM (3) and 13.5 mu (4). | | Planta Med . 2004 Oct;70(10):904-908. | | Inhibition of leukotriene biosynthesis by quinolone alkaloids from the fruits of Evodia rutaecarpa[Pubmed: 15490316] | | The n-hexane extract of the fruits of Evodia rutaecarpa showed a considerable inhibiting effect on leukotriene biosynthesis in human granulocytes. Bioassay-guided fractionation of the extract led to the isolation of the 5 quinolone alkaloids: 1-methyl-2-nonyl-4(1H)-quinolinone, 1-methyl-2-(6Z)-6-undecenyl-4(1H)-quinolinone, 1-methyl-2-(4Z,7Z)-4,7-tridecadienyl-4(1H)-quinolinone, evocarpine and 1-methyl-2-(6Z,9Z)-6,9-pentadecadienyl-4(1H)-quinolinone. The compounds exhibited inhibitory activity on leukotriene biosynthesis in a bioassay using human polymorphonuclear granulocytes, with IC50 values of 12.1, 10.0, 10.1, 14,6 and 12.3 microM, respectively. Structure elucidation of the compounds was achieved by 1D and 2D NMR experiments and comparison of spectral data with literature data. |
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| In vivo: |
| Biomed Chromatogr . 2016 Dec;30(12):1975-1983. | | Screening and identification of hepatotoxic component in Evodia rutaecarpa based on spectrum-effect relationship and UPLC-Q-TOFMS[Pubmed: 27239783] | | Evodia rutaecarpa (E. rutaecarpa) has been used to treat aches, vomiting and dysentery in traditional Chinese medicine. However, as a mildly toxic herb its toxic components have not been elucidated. An attempt was made to illuminate the hepatotoxic constituents of E. rutaecarpa. The 50% ethanol extracts of E. rutaecarpa from 19 different sources were used to establish UPLC fingerprints and administered to mice at a dose of 35 g/kg (crude medicine weight/mouse weight) once daily for 14 days. Serum levels of alanine transaminase, aspartate aminotransferase and liver coefficient were used as indices of liver injury. Additionally, the characteristic peaks of 19 fingerprints were identified. Spectrum-effect relationships between fingerprints and hepatotoxic indicators were analyzed using bivariate correlation analysis (BCA). The UPLC fingerprints were established and a total of 28 main compounds were identified. Because of the inherent variations in chemical compositions, the liver injury levels were different among the E. rutaecarpa samples from 19 sites of production. BCA results indicated that compounds dihydrorutaecarpine, 6-acetoxy-5-epilimonin, goshuyuamide I, 1-methyl-2-[(Z)-5-undecenyl]-4(1H)-quinolone, 1-methyl-2-[(4Z,7Z)-4,7-tridecadienyl]-4(1H)-quinolone, evocarpine and 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone were tentatively determined as the primary hepatotoxic components. The present study provides a valuable method for the discovery of hepatotoxic constituents by combination of fingerprints and hepatotoxicity index. |
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