Citation: Zhu Jianxun, Lu Xiaofeng, Fan Xiaona, Wu Ruibo, Diao Hongjuan, Yu Rongmin, Xu Hanhong, Zi Jiachen. A new cytotoxic salannin-class limonoid alkaloid from seeds of Azadirachta indica A. Juss[J]. Chinese Chemical Letters, ;2018, 29(8): 1261-1263. doi: 10.1016/j.cclet.2017.11.042 shu

A new cytotoxic salannin-class limonoid alkaloid from seeds of Azadirachta indica A. Juss

Zhu Jianxun ^a,b ,
Lu Xiaofeng ^a,b ,
Fan Xiaona ^c ,
Wu Ruibo ^d ,
Diao Hongjuan ^d ,
Yu Rongmin ^a,d ,
Xu Hanhong ^e ,
Zi Jiachen ^a,b,,

a.
Biotechnological Institute of Chinese Materia Medica, Jinan University, Guangzhou 510632, China
b.
College of Pharmacy, Jinan University, Guangzhou 510632, China
c.
School of Life Sciences, Sun Yat-sen University, Guangzhou 510275, China
d.
School of Pharmaceutical Science, Sun Yat-sen University, Guangzhou 510006, China
e.
State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, South China Agricultural University, Guangzhou 510642, China

Corresponding author: Zi Jiachen, jiachen_zi@163.com
Received Date: 24 September 2017
Revised Date: 28 November 2017
Accepted Date: 30 November 2017
Available Online: 6 August 2017

Figures(3)

A new cytotoxic salannin-class limonoid alkaloid, azadiramide A (1), was isolated from seeds of Azadirachta indica A. Juss. Its structure was elucidated by extensive analysis of spectroscopic data and quantum chemical calculation. Compound 1 is a rare salannin-class limonoid alkaloid. To our best knowledge, only two compounds belonging to this type were so far found. It showed inhibitory activity against human breast cancer MDA-MB-231 cell line with IC₅₀ value of 2.70 0.63 μmol/L.
- Azadirachta indica,
- Limonoid,
- Alkaloid,
- Cytotoxic activity
1. [1]
  V.S. Kumar, V. Navaratnam, Asian Pac. J. Trop. Biomed. 3 (2013) 505-514. doi: 10.1016/S2221-1691(13)60105-7
2. [2]
  S. Senthil-Nathan, Front. Physiol. 4 (2013) 359.
3. [3]
  P. Thakurta, P. Bhowmik, S. Mukherjee, et al., J. Ethnopharmacol. 111 (2007) 607-612. doi: 10.1016/j.jep.2007.01.022
4. [4]
  G. Brahmachari, ChemBioChem 5 (2004) 408-421. doi: 10.1002/cbic.v5:4
5. [5]
  Q.G. Tan, X.D. Lou, Chem. Rev. 111 (2011) 7437-7522. doi: 10.1021/cr9004023
6. [6]
  T. Akihisa, T. Noto, A. Takahashi, et al., J. Oleo Sci. 58 (2009) 581-594. doi: 10.5650/jos.58.581
7. [7]
  A. Alam, S. Haldar, H.V. Thulasiram, et al., J. Biol. Chem. 287 (2012) 24844-24861. doi: 10.1074/jbc.M112.341321
8. [8]
  S.A. Khalid, H. Duddeck, M. Gonzalez-Sierra, J. Nat. Prod. 52 (1989) 922-927. doi: 10.1021/np50065a002
9. [9]
  W. Maneerata, S. Laphookhieoa, S. Koysomboonb, et al., Phytomedicine 15 (2008) 1130-1134. doi: 10.1016/j.phymed.2008.05.004
10. [10]
  R. Subramani, E. Gonzalez, A. Arumugam, et al., Sci. Rep. 6 (2016) 19819. doi: 10.1038/srep19819
11. [11]
  J. Sophia, T.K. Kiran Kishore, J. Kowshik, et al., Sci. Rep. 6 (2016) 22192. doi: 10.1038/srep22192
12. [12]
  S.C. Gupta, S.K. Francis, M.S. Nair, et al., J. Biol. Chem. 288 (2013) 32343-32356. doi: 10.1074/jbc.M113.455188
13. [13]
  W. Kraus, A. Klenk, M. Bokel, et al., Liebigs Ann. Chem. (1987) 337-340.
14. [14]
  L.J. Meng, Q.L. Guo, C.G. Zhu, et al., Chin. Chem. Lett. 29 (2018) 119-122. doi: 10.1016/j.cclet.2017.05.019
15. [15]
  J.H. Li, Y. Li, F.L. An, et al., Tetrahedron 72 (2016) 7481-7487. doi: 10.1016/j.tet.2016.09.061
16. [16]
  S.H. Qi, L. Chen, D.G. Wu, et al., Tetrahedron 59 (2003) 4193-4199. doi: 10.1016/S0040-4020(03)00573-8
17. [17]
  G.Y. Zhu, G. Chen, L. Liu, et al., J. Nat. Prod. 77 (2014) 983-989. doi: 10.1021/np401089h
1. [1]
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2. [2]
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3. [3]
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4. [4]
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5. [5]
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16. [16]
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17. [17]
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18. [18]
  Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
19. [19]
  Xiaoli Deng , Xiangchao Lu , Yang Cao , Qianjin Chen . Electrochemical imaging uncovers the heterogeneity of HER activity by sulfur vacancies in molybdenum disulfide monolayer. Chinese Chemical Letters, 2025, 36(3): 110379-. doi: 10.1016/j.cclet.2024.110379
20. [20]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859

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沈阳化工大学材料科学与工程学院沈阳 110142