title: Novel tirucallane triterpenoids from the stem bark of Toona sinensis.
abstract: Phytochemical investigation on the stem bark of Toona sinensis was carried out by various chromatographic techniques resulting in the isolation and elucidation of two novel tirucallane triterpenoids, named (20S)-3-oxo-tirucalla-25-nor-7-en-24-oic acid (1) and (20S)-5α,8α-epidioxy-3-oxo-24-nor-6.9(11)-dien-23-oic acid (2), along with fifteen known triterpenoids (3-17), their structures were determined by extensive spectroscopic methods, including 1D-, 2D-NMR and HR-ESI-MS experiments. Compound 2 is uncommon in nature, which possesses a peroxide bridge cross C-5 and C-8 in the triterpenoid skeleton. All isolated compounds were evaluated for cytotoxicity against five human tumor cell lines (A-549, Hela, HepG2, SGC-7901 and SW-480), among them, compound 17 displayed strongest cytotoxic activity against A-549 cells and the results indicated that its cytotoxicity against A-549 cells was mediated by the intrinsic mitochondrial apoptotic pathway. In addition, ROS production-inhibitory activities were also evaluated, but none of them was active.
authors.affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Tang
authors.affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
authors.forename: Jian
authors.initials: J
authors.lastname: Xu
authors.affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China; Key Laboratory of Biomedical Functional Materials, China Pharmaceutical University, Nanjing 211198, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Drug Quality Control and Pharmacovigilance, Ministry of Education, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China.
authors.forename: Wen-Yuan
authors.initials: WY
authors.lastname: Liu
authors.affiliation: Jiangxi Qingfeng Pharmaceutical Corporation, Ganzhou 341000, China.
authors.forename: Ning
authors.initials: N
authors.lastname: Xie
authors.affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Chen
authors.affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China; Key Laboratory of Biomedical Functional Materials, China Pharmaceutical University, Nanjing 211198, China.
authors.forename: Feng
authors.initials: F
authors.lastname: Feng
authors.affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China; Key Laboratory of Biomedical Functional Materials, China Pharmaceutical University, Nanjing 211198, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Qu
mesh_terms: D000072283:A549 Cells; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification; D017209:Apoptosis; D045744:Cell Line, Tumor; D006801:Humans; D029582:Meliaceae / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry*; D017382:Reactive Oxygen Species / Q000378:metabolism; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D017382:Reactive Oxygen Species; D014315:Triterpenes; C514393:tirucallane
keywords: (20S,24R)-epoxydammarane-1225-diol-3-one (PubChem CID: 14038588); (20S,24R)-epoxydammarane-3β,25-diol (PubChem CID: 11385662); 20-hydroxy-24-dammaren-3-one (PubChem CID: 441676); Cytotoxic activity; ROS production-inhibitory activity; Tirucallane triterpenoids; Toona sinensis; bourjotinolone B (PubChem CID: 101280173); cabralealactone (PubChem CID: 44421647); cylindrictone D (PubChem CID: 25104959); methyl shoreate (PubChem CID: 44421646); ocotillone (PubChem CID: 12313665); richenone (PubChem CID: 101599479); shoreic acid (PubChemCID: 12315515)