title: A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle.
abstract: The present investigation of the chemical constituents of the stem barks of Ailanthus altissima has resulted in the isolation of six canthinone-type alkaloids, including a new compound, (R)-5-(1-hydroxyethyl)-canthine-6-one (1), and five known compounds (2-6). Moreover, four phenyl propanoids (7-10), two lignans (11 and 12), two triterpenoids (13 and 14) and a fatty acid (15) having previously known chemical structures were isolated during the same course of this study. The structure of the new compound was elucidated by physical (m.p., [α]D) and spectroscopic data (¹H-NMR, (13)C-NMR, 2D NMR, and HR-DART-MS) interpretation and its absolute configuration was determined by electronic circular dichroism (ECD) data and quantum chemical calculations. The inflammatory activities of the isolates were screened on lipopolysaccharide (LPS)-induced nitric oxide (NO), a proinflammatory mediator, in RAW 264.7 cells. Among these isolated compounds, six compounds exhibited significant inhibition of NO production, with IC50 values in the range of 5.92 ± 0.9 to 15.09 ± 1.8 μM.
authors.affiliation: College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea. hyemi586@gmail.com.
authors.forename: Hye Mi
authors.initials: HM
authors.lastname: Kim
authors.affiliation: Department of Life &amp; Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea. lee2649318@naver.com.
authors.forename: Jin Su
authors.initials: JS
authors.lastname: Lee
authors.affiliation: College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea. jurdas30@gmail.com.
authors.forename: Jurdas
authors.initials: J
authors.lastname: Sezirahiga
authors.affiliation: Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 136-713, Korea. kjwkjy1207@gmail.com.
authors.forename: Jaeyoung
authors.initials: J
authors.lastname: Kwon
authors.affiliation: Department of Life &amp; Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea. jeongmiran@hanmail.net.
authors.forename: Miran
authors.initials: M
authors.lastname: Jeong
authors.affiliation: Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 136-713, Korea. dongholee@korea.ac.kr.
authors.forename: Dongho
authors.initials: D
authors.lastname: Lee
authors.affiliation: College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea. jchoi@khu.ac.kr.|Department of Life &amp; Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea. jchoi@khu.ac.kr.
authors.forename: Jung-Hye
authors.initials: JH
authors.lastname: Choi
authors.affiliation: College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea. dsjang@khu.ac.kr.|Department of Life &amp; Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea. dsjang@khu.ac.kr.
authors.forename: Dae Sik
authors.initials: DS
authors.lastname: Jang
mesh_terms: D032268:Ailanthus / Q000737:chemistry*; D000470:Alkaloids / Q000008:administration & dosage / Q000737:chemistry* / Q000302:isolation & purification; D000818:Animals; D007249:Inflammation / Q000139:chemically induced / Q000188:drug therapy*; D017705:Lignans / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D000067996:RAW 264.7 Cells / Q000187:drug effects; D014315:Triterpenes / Q000737:chemistry
chemical_list: D000470:Alkaloids; D017705:Lignans; D010936:Plant Extracts; D020005:Propanols; D014315:Triterpenes; C439395:1-phenylpropanol
keywords: Ailanthus altissima; canthinone type alkaloids; inflammation; nitric oxide; simaroubaceae