Monoterpenoid Indole Alkaloids from Alstonia yunnanensis and Their Cytotoxic and Anti-inflammatory Activities

被引：33
作者：
Cao, Peng [1 ]
Liang, Yong [1 ]
Gao, Xu [1 ]
Li, Xiao-Ming [1 ]
Song, Zhen-Quan [1 ]
Liang, Guobiao [1 ]
机构：
[1] Shenyang No Hosp, Shenyang Mil Area Command, Gen Hosp, Dept Neurosurg,Inst Neurol, Shenyang 110018, Peoples R China
来源：
MOLECULES | 2012年 / 17卷 / 11期
关键词：
Alstonia yunnanensis; Apocynaceae; monoterpenoid indole alkaloids; cytotoxicity; anti-inflammatory activities; A-D; SCHOLARIS; LEAVES; MACROPHYLLA; BISINDOLE; MACROLINE; ANGUSTIFOLIA; ACID;
D O I：
10.3390/molecules171113631
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The 80% ethanol extract of Alstonia yunnanensis afforded five new monoterpenoid indole alkaloids: 11-hydroxy-6,7-epoxy-8-oxo-vincadifformine (1), 14-chloro-15-hydroxy-vincadifformine (2), perakine N-4-oxide (3), raucaffrinoline N-4-oxide (4), and vinorine N-1,N-4-dioxide (5), together with three known compounds: 11-methoxy-6,7-epoxy-8-oxo-vincadifformine (6), vinorine N-4-oxide (7) and vinorine (8). The structures of the isolated compounds were established based on 1D and 2D (H-1-H-1-COSY, HMQC, HMBC, and ROESY) NMR spectroscopy, in addition to high resolution mass spectrometry. The isolated compounds were tested in vitro for cytotoxic potential against seven tumor cell lines and anti-inflammatory activities. Compounds 3, 4 and 7 exhibited weak cytotoxicity against the tested cell lines and selective inhibition of Cox-2 (>85%).
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页码：13631 / 13641
页数：11
相关论文
共 34 条
  • [1] [Anonymous], [No title captured]
  • [2] Alstiphyllanines E-H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter
    Arai, Hiroko
    Hirasawa, Yusuke
    Rahman, Abdul
    Kusumawati, Idha
    Zaini, Noor Cholies
    Sato, Seizo
    Aoyama, Chihiro
    Takeo, Jiro
    Morita, Hiroshi
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (06) : 2152 - 2158
  • [3] Actinophyllic acid, a potent indole alkaloid inhibitor of the coupled enzyme assay carboxypeptidase U hippuricase from the leaves of Alstonia actinophylla (Apocynaceae)
    Carroll, AR
    Hyde, E
    Smith, J
    Quinn, RJ
    Guymer, G
    Forster, PI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) : 1096 - 1099
  • [4] Evaluation of Alstonia scholaris leaves for broncho-vasodilatory activity
    Channa, S
    Dar, A
    Ahmed, S
    Atta-ur-Rahman
    [J]. JOURNAL OF ETHNOPHARMACOLOGY, 2005, 97 (03) : 469 - 476
  • [5] ALKALOIDS FROM ROOTS OF ALSTONIA-YUNNANENSIS
    CHEN, WM
    YAN, YP
    LIANG, XT
    [J]. PLANTA MEDICA, 1983, 49 (01) : 62 - 62
  • [6] Cyclooxygenase inhibitors not inhibit resting lung cancer A549 cell proliferation
    Duan, Weigang
    Zhang, Luyong
    [J]. PROSTAGLANDINS LEUKOTRIENES AND ESSENTIAL FATTY ACIDS, 2006, 74 (05): : 317 - 321
  • [7] Monoterpenoid Indole Alkaloids from Alstonia yunnanensis
    Feng, Tao
    Li, Yan
    Cai, Xiang-Hai
    Gong, Xun
    Liu, Ya-Ping
    Zhang, Rong-Ting
    Zhang, Xiang-Yun
    Tan, Qin-Gang
    Luo, Xiao-Dong
    [J]. JOURNAL OF NATURAL PRODUCTS, 2009, 72 (10): : 1836 - 1841
  • [8] PRELIMINARY EVALUATION OF EXTRACTS OF ALSTONIA-SCHOLARIS BARK FOR INVIVO ANTIMALARIAL ACTIVITY IN MICE
    GANDHI, M
    VINAYAK, VK
    [J]. JOURNAL OF ETHNOPHARMACOLOGY, 1990, 29 (01) : 51 - 57
  • [9] INDOLE ALKALOIDS FROM THE LEAVES OF ALSTONIA SCHOLARIS
    Hirasawa, Yusuke
    Miyama, Saori
    Kawahara, Nobuo
    Goda, Yukihiro
    Rahman, Abdul
    Ekasari, Wiwied
    Widyawaruyanti, Aty
    Indrayanto, Gunawan
    Zaini, Noor Cholies
    Morita, Hiroshi
    [J]. HETEROCYCLES, 2009, 79 : 1107 - 1112
  • [10] Alstiphyllanines A-D, Indole Alkaloids from Alstonia macrophylla
    Hirasawa, Yusuke
    Arai, Hiroko
    Zaima, Kazumasa
    Oktarina, Rice
    Rahman, Abdul
    Ekasari, Wiwied
    Widyawaruyanti, Aty
    Indrayanto, Gunawan
    Zaini, Noor Cholies
    Morita, Hiroshi
    [J]. JOURNAL OF NATURAL PRODUCTS, 2009, 72 (02): : 304 - 307
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