title: New monoterpenoid oxindole alkaloid derivatives from the stems of Uncaria hirsuta Havil. and their cytotoxicity and tandem mass spectrometric fragmentation.
abstract: Four new alkaloids, comprising three 3-oxo-3,7-seco-oxindole alkaloids (hirsutanine D-F, 1-3) and one oxindole alkaloid N-oxide (uncarine B N-oxide, 4), together with four known heteroyohimbine-type oxindole alkaloids, were isolated from the stems of Uncaria hirsuta Havil. Structures of 1-4 were elucidated by extensive NMR and HR-ESIMS data analyses. Compound 3 is the first 3-oxo-3,7-seco-oxindole alkaloid with ring B opened and degraded isolated from the Uncaria genus. Compounds 1-3 exhibited slight inhibition effect on the proliferation of the breast cancer cell MDA-MB-231. The positive mode collision-induced dissociation of the 3-oxo-3,7-seco-oxindole alkaloids (1-3) was featured by the β-cleavage and α-cleavage of the amido bond, while the N-oxide (4) showed characteristic neutral eliminations of ·OH and H2O.
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Haike Road 501, Shanghai 201203, People's Republic of China; University of Chinese Academy of Sciences, No.19A Yuquan Road, Beijing 100049, People's Republic of China.
authors.forename: Hui-Qin
authors.initials: HQ
authors.lastname: Pan
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Haike Road 501, Shanghai 201203, People's Republic of China.
authors.forename: Wen-Zhi
authors.initials: WZ
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
authors.forename: Dan
authors.initials: D
authors.lastname: Zhao
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
authors.forename: Cheng
authors.initials: C
authors.lastname: Luo
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Haike Road 501, Shanghai 201203, People's Republic of China; University of Chinese Academy of Sciences, No.19A Yuquan Road, Beijing 100049, People's Republic of China.
authors.forename: Chang-Liang
authors.initials: CL
authors.lastname: Yao
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Haike Road 501, Shanghai 201203, People's Republic of China.
authors.forename: Xiao-Jian
authors.initials: XJ
authors.lastname: Shi
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Haike Road 501, Shanghai 201203, People's Republic of China.
authors.forename: Yi-Bei
authors.initials: YB
authors.lastname: Zhang
authors.affiliation: Beijing Institute of Genomics, Chinese Academy of Sciences, No. 1 Beichen West Road, Chaoyang District, Beijing 100101, China.
authors.forename: Shi-You
authors.initials: SY
authors.lastname: Li
authors.affiliation: Beijing Institute of Genomics, Chinese Academy of Sciences, No. 1 Beichen West Road, Chaoyang District, Beijing 100101, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Bi
authors.affiliation: Beijing Institute of Genomics, Chinese Academy of Sciences, No. 1 Beichen West Road, Chaoyang District, Beijing 100101, China.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Wang
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Haike Road 501, Shanghai 201203, People's Republic of China.
authors.forename: Shuai
authors.initials: S
authors.lastname: Yao
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Haike Road 501, Shanghai 201203, People's Republic of China. Electronic address: wanyingwu@simm.ac.cn.
authors.forename: Wan-Ying
authors.initials: WY
authors.lastname: Wu
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Haike Road 501, Shanghai 201203, People's Republic of China. Electronic address: daguo@simm.ac.cn.
authors.forename: De-An
authors.initials: DA
authors.lastname: Guo
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D045744:Cell Line, Tumor; D006801:Humans; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry* / Q000302:isolation & purification; D000078183:Oxindoles; D018547:Plant Stems / Q000737:chemistry; D032070:Uncaria / Q000737:chemistry
chemical_list: D000470:Alkaloids; D007211:Indoles; D039821:Monoterpenes; D000078183:Oxindoles; C022960:2-oxindole
keywords: Collision-induced dissociation; MDA-MB-231; Monoterpenoid oxindole alkaloid; Uncaria hirsuta