tabernaemontanine | 2134-98-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 沃巴桑生物碱
• 英文名称: tabernaemontanine
• 英文别名: vobasine；methyl (1S,14S,15S,18S)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate
• CAS: 2134-98-7
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: FFVRRQMGGGTQRH-DTPILHQWSA-N

物化性质

• 熔点：
  217-219 °C(Solv: methanol (67-56-1))
• 沸点：
  515.9±50.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tabernaemontanine 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以36%的产率得到tabernaemontanine hydrazone
  参考文献：
  名称：

  Monoterpene indole alkaloid hydrazone derivatives with apoptosis inducing activity in human HCT116 colon and HepG2 liver carcinoma cells

  摘要：

  The derivatization of dregamine (1) and tabernaemontanine (2), two epimeric monoterpene indole alkaloids isolated from the methanol extract of the roots of Tabernaemontana elegans, with several hydrazines and hydroxylamine gave rise to ten new derivatives (3-12). Their structures were assigned by spectroscopic methods, including 2D NMR experiments. The compounds were tested for their ability to induce apoptosis in HCT116 colon and HepG2 liver cancer cells. Firstly, the cytotoxicity of all compounds (1-12) was evaluated in both cell lines by the MTS assay. The most active compounds (6, 9, 10) along with 1 and 2 were further investigated for their apoptosis induction capability by Guava ViaCount flow cytometry assays, nuclear morphology evaluation by Hoechst staining, and caspase-3/7 activity assays. Compounds 9 and 10 showed promising apoptosis induction profile, displaying higher activities than 5-fluorouracil, the mainstay in colon cancer treatment. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.084
• 作为产物：
  描述：

  vobasine 生成 dregamine 、 tabernaemontanine
  参考文献：
  名称：

  Terpenoid indole alkaloid biotransformation capacity of suspension cultures of Tabernaemontana divaricata

  摘要：

  Two cell lines of Tabernaemontana divaricata derived from the same suspension culture were compared with respect to their biotransformation capacity. One is a high indole alkaloid-producing culture which accumulated mainly O-acetylvallesamine. The other cell line biosynthesizes terpehoid indole alkaloids in much lower amounts. Both cell lines were cultured in medium containing either conopharyngine, coronaridine, vobasine or tabersonine. Chemical breakdown was followed in fresh and used culture medium in the absence of cell culture. All the alkaloids investigated underwent chemical transformation. Most of the biotransformation products accumulated by the cultures have been reported to occur in intact plants. Since all the alkaloids added were transformed in the same way by both cultures, the two cell lines seem to have the same biotransformation potential.

  DOI：

  10.1016/s0031-9422(00)90584-3

文献信息

• Vobatensines A–F, Cytotoxic Iboga-Vobasine Bisindoles from <i>Tabernaemontana corymbosa</i>
  作者：Dawn Su-Yin Sim、Wuen-Yew Teoh、Kae-Shin Sim、Siew-Huah Lim、Noel F. Thomas、Yun-Yee Low、Toh-Seok Kam

  DOI：10.1021/acs.jnatprod.5b01117

  日期：2016.4.22

  Six new bisindole alkaloids of the iboga-vobasine type, vobatensines A–F (1–6), in addition to four known bisindoles (8–11), were isolated from a stem bark extract of a Malayan Tabernaemontana corymbosa. The structures of these alkaloids were determined based on analysis of the spectroscopic data and in the case of vobatensines A (1), B (2), and 16′-decarbomethoxyvoacamine (8) also confirmed by partial

  所述iboga-vobasine类型的六个新的双吲哚生物碱，vobatensines A-F（1 - 6）中，除了已知的四种双吲哚（8 - 11），是从一个马来亚的树皮提取物中分离狗牙花属伞房。这些生物碱的结构是根据光谱数据分析确定的，在伏巴滕斯汀A（1），B（2）和16'-脱甲氧甲氧胺（8）的情况下，也通过部分合成得到了证实。这些生物碱（九1 - 5，8 - 11）显示出对人KB，PC-3，LNCaP，HCT 116，HT-29，MCF7，MDA-MB-231和A549癌细胞的显着体外生长抑制活性。
• Monoterpene indole alkaloid hydrazone derivatives with apoptosis inducing activity in human HCT116 colon and HepG2 liver carcinoma cells
  作者：Angela Paterna、Pedro M. Borralho、Sofia E. Gomes、Silva Mulhovo、Cecília M.P. Rodrigues、Maria-José U. Ferreira

  DOI：10.1016/j.bmcl.2015.06.084

  日期：2015.9

  The derivatization of dregamine (1) and tabernaemontanine (2), two epimeric monoterpene indole alkaloids isolated from the methanol extract of the roots of Tabernaemontana elegans, with several hydrazines and hydroxylamine gave rise to ten new derivatives (3-12). Their structures were assigned by spectroscopic methods, including 2D NMR experiments. The compounds were tested for their ability to induce apoptosis in HCT116 colon and HepG2 liver cancer cells. Firstly, the cytotoxicity of all compounds (1-12) was evaluated in both cell lines by the MTS assay. The most active compounds (6, 9, 10) along with 1 and 2 were further investigated for their apoptosis induction capability by Guava ViaCount flow cytometry assays, nuclear morphology evaluation by Hoechst staining, and caspase-3/7 activity assays. Compounds 9 and 10 showed promising apoptosis induction profile, displaying higher activities than 5-fluorouracil, the mainstay in colon cancer treatment. (C) 2015 Elsevier Ltd. All rights reserved.
• Terpenoid indole alkaloid biotransformation capacity of suspension cultures of Tabernaemontana divaricata
  作者：Denise Dagnino、Jan Schripsema、Robert Verpoorte

  DOI：10.1016/s0031-9422(00)90584-3

  日期：1994.2

  Two cell lines of Tabernaemontana divaricata derived from the same suspension culture were compared with respect to their biotransformation capacity. One is a high indole alkaloid-producing culture which accumulated mainly O-acetylvallesamine. The other cell line biosynthesizes terpehoid indole alkaloids in much lower amounts. Both cell lines were cultured in medium containing either conopharyngine, coronaridine, vobasine or tabersonine. Chemical breakdown was followed in fresh and used culture medium in the absence of cell culture. All the alkaloids investigated underwent chemical transformation. Most of the biotransformation products accumulated by the cultures have been reported to occur in intact plants. Since all the alkaloids added were transformed in the same way by both cultures, the two cell lines seem to have the same biotransformation potential.