title: Isolation, chemotaxonomic significance and cytotoxic effects of quassinoids from Brucea javanica.
abstract: A new quassinoid, bruceene A (1) along with seventeen known quassinoids (2-18) was isolated from the fruits of Brucea javanica. The structure of 1 was elucidated by extensive spectroscopic methods, and was further confirmed by single-crystal X-ray diffraction analysis. Isolation of similar quassinoids 1-3 as those in genus Ailanthus from genus Brucea, indicated the close chemotaxonomic relationship between these two genera, which further supported the phylogenetic study by DNA analysis. Compounds 5, 7, 10 and 12 with a 3-hydroxy-3-en-2-one moiety showed potent inhibitory activities against the MCF-7 and MDA-MB-231 cells with IC50 values in the ranges 0.063-0.182 μM and 0.081-0.238 μM, respectively; while glycosidation at 3-OH significantly decreased the cytotoxicity. It was also found that the most potent compound 7 induced apoptosis in MCF-7 cells via the intrinsic mitochondrial apoptotic pathway.
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China; Department of Pharmacy, Hainan General Hospital, Haikou 570311, PR China.
authors.forename: Qing-Mei
authors.initials: QM
authors.lastname: Ye
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors.forename: Liang-Liang
authors.initials: LL
authors.lastname: Bai
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors.forename: Shu-Zhi
authors.initials: SZ
authors.lastname: Hu
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors.forename: Hai-Yan
authors.initials: HY
authors.lastname: Tian
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors.forename: Li-Jun
authors.initials: LJ
authors.lastname: Ruan
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors.forename: Ya-Fang
authors.initials: YF
authors.lastname: Tan
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors.forename: Li-Ping
authors.initials: LP
authors.lastname: Hu
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors.forename: Wen-Cai
authors.initials: WC
authors.lastname: Ye
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China; Shenzhen Engineering Laboratory of Lingnan Medicinal Resources Development and Application, Shenzhen Institute for Drug Control, Shenzhen 518057, PR China. Electronic address: dmzhang701@gmail.com.
authors.forename: Dong-Mei
authors.initials: DM
authors.lastname: Zhang
authors.affiliation: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China; Shenzhen Engineering Laboratory of Lingnan Medicinal Resources Development and Application, Shenzhen Institute for Drug Control, Shenzhen 518057, PR China. Electronic address: trwjiang@jnu.edu.cn.
authors.forename: Ren-Wang
authors.initials: RW
authors.lastname: Jiang
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification; D017209:Apoptosis; D032269:Brucea / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D061986:MCF-7 Cells; D015394:Molecular Structure; D036702:Quassins / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D036702:Quassins
keywords: Breast cancer; Brucea javanica; Bruceene A; Chemotaxonomics; Quassinoids