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1-Methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone
1-Methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone
ChemFaces products have been cited in many studies from excellent and top scientific journals
Product Name 1-Methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone
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CAS No.: 120693-52-9
Catalog No.: CFN91687
Molecular Formula: C25H35NO
Molecular Weight: 365.6 g/mol
Purity: >=98%
Type of Compound: Alkaloids
Physical Desc.: Oil
Source: The fructus of Evodia rutaecarpa
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download: COA    MSDS
Similar structural: Comparison (Web)  (SDF)
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries
Biological Activity
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.
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.
1-Methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone Description
Source: The fructus of Evodia rutaecarpa
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

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After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7352 mL 13.6761 mL 27.3523 mL 54.7046 mL 68.3807 mL
5 mM 0.547 mL 2.7352 mL 5.4705 mL 10.9409 mL 13.6761 mL
10 mM 0.2735 mL 1.3676 mL 2.7352 mL 5.4705 mL 6.8381 mL
50 mM 0.0547 mL 0.2735 mL 0.547 mL 1.0941 mL 1.3676 mL
100 mM 0.0274 mL 0.1368 mL 0.2735 mL 0.547 mL 0.6838 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Cell Research:
Nat Prod Res . 2021 Jan;35(2):222-227.
A new quinolone alkaloid from the fruits of Tetradium ruticarpum[Pubmed: 31273999]
A rare new quinolone alkaloid containing three degrees of unsaturation in the side chain, named as 1-methyl-2-[(6Z,9Z,12Z)-6,9,12-pentadecatriene]-4(1H)-quinolone (1), together with three known quinolone alkaloids 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone (2), 1-methyl-2-[(4Z,7Z)-4,7-tridecadienyl]-4(1H)-quinolone (3), 1-methyl-2-[(Z)-8-tridecenyl]-4(1H)-quinolone (4), were isolated from the fruits of Tetradium ruticarpum (A.Juss.) T.G.Hartley. Their structures were elucidated by physicochemical properties and spectroscopic data. All compounds were evaluated for their cytotoxic activities against three human tumor cell lines, including Lovo, MDA-MB-231, HeLa cells, by MTT method in 96-well microplates, and compounds 1 exhibited potent activity against MDA-MB-231 cells with IC50 values of 7.95 μM.
Structure Identification:
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.
J Chromatogr A . 2005 May 13;1074(1-2):139-144.
Preparative isolation and purification of alkaloids from the Chinese medicinal herb Evodia rutaecarpa (Juss.) Benth by high-speed counter-current chromatography[Pubmed: 15941049]
High-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water system (5:5:7:5, v/v) was applied to the isolation and purification of alkaloids from the Chinese medicinal plant Evodia rutaecarpa (Juss.) Benth. Five kinds of alkaloids were obtained and yielded 28 mg of evodiamine (I), 19 mg of rutaecarpine (II), 21 mg of evocarpine (III), 16mg of 1-methy-2-[(6Z,9Z)]-6,9-pentadecadienyl-4-(1H)-quinolone (IV), 12 mg of 1-methyl-2-dodecyl-4-(1H)-quinolone (V) from 180 mg of crude extract in a one-step separation, with the purity of 98.7%, 98.4%, 96.9%, 98.0%, 97.2%, respectively, as determined by high performance liquid chromatography (HPLC). The structures of these compounds were identified by 1H NMR and 13CNMR.
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