Citation: Long Zhang, Xing Xin Cao, Hai Xia Jiang, Biao Jiang, Yu Xin Cui. Characterizing some gossypol and gossypolone Schiff's bases by studying their fragmentation patterns with electrospray ionization tandem mass spectra[J]. Chinese Chemical Letters, ;2009, 20(6): 716-719. doi: 10.1016/j.cclet.2008.12.049 shu

Characterizing some gossypol and gossypolone Schiff's bases by studying their fragmentation patterns with electrospray ionization tandem mass spectra

a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Received Date: 10 November 2008

To investigate the structural form of gossypol and gossypolone Schiff's bases, seven relevant Schiff's bases were synthesized and the electrospray ionization-tandem mass spectrometry (ESI-MS/MS) with low-energy collision-induced dissociation was used to analyze their fragmentations. A common fragmentation pathway with the loss of RNH₂ from those schiff's bases quasi-molecular ions was observed and proposed on the basis of their MS/MS spectra data. This common pathway indicated that those Schiff's bases existed mainly as the enamine form not the imine form previously showed in most reports.
- Gossypol Schiff's bases,
- Gossypolone Schiff's bases,
- ESI-MS,
- Enamine form,
- Imine form
1. [1]
  Ke Wu , Xiuqin Ruan , Shuolei Jia , Enyuan Wang , Qingfa Zhou . DABCO-catalyzed [3+4] annulations of Schiff bases with α-substituted allenes: Construction of functionalized benzazepine derivatives. Chinese Chemical Letters, 2025, 36(7): 110646-. doi: 10.1016/j.cclet.2024.110646
2. [2]
  Jun Lu , Jinrui Yan , Yaohao Guo , Junjie Qiu , Shuangliang Zhao , Bo Bao . Controlling solid form and crystal habit of triphenylmethanol by antisolvent crystallization in a microfluidic device. Chinese Chemical Letters, 2024, 35(4): 108876-. doi: 10.1016/j.cclet.2023.108876
3. [3]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
4. [4]
  Ming-Yi Sun , Lu Zhang , Ya Li , Chong-Chen Wang , Peng Wang , Xueying Ren , Xiao-Hong Yi . Recovering Ag⁺ with nano-MOF-303 to form Ag/AgCl/MOF-303 photocatalyst: The role of stored Cl⁻ ions. Chinese Chemical Letters, 2025, 36(2): 110035-. doi: 10.1016/j.cclet.2024.110035
5. [5]
  Jinqi Yang , Xiaoxiang Hu , Yuanyuan Zhang , Lingyu Zhao , Chunlin Yue , Yuan Cao , Yangyang Zhang , Zhenwen Zhao . Direct observation of natural products bound to protein based on UHPLC-ESI-MS combined with molecular dynamics simulation. Chinese Chemical Letters, 2025, 36(5): 110128-. doi: 10.1016/j.cclet.2024.110128
6. [6]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
7. [7]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
8. [8]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
9. [9]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
10. [10]
  Yong-Fang Shi , Sheng-Hua Zhou , Zuju Ma , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . From [Ba3S][GeS4] to [Ba3CO3][MS4] (M = Ge, Sn): Enhancing optical anisotropy in IR birefringent crystals via functional group implantation. Chinese Journal of Structural Chemistry, 2025, 44(1): 100455-100455. doi: 10.1016/j.cjsc.2024.100455
11. [11]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
12. [12]
  Haoyu Tian , Xiaolin Cui , Guiwei Yao , Wenyan Wei , Junchao Lu , Senyao Zheng , Xingjian Wang , Xun Chen , Guangkuan Zhao , Dulin Kong . The sulfenylation of enamine esters with heterocyclic thiols or disulfides in water and application to DNA-compatible chemistry. Chinese Chemical Letters, 2025, 36(12): 111006-. doi: 10.1016/j.cclet.2025.111006
13. [13]
  Jiajie Gu , Jiaxiang Gu , Lei Yu . Selenium and Alzheimer's disease. Chinese Chemical Letters, 2025, 36(8): 110727-. doi: 10.1016/j.cclet.2024.110727
14. [14]
  Yadan SUN , Xinfeng LI , Qiang LIU , Oshio Hiroki , Yinshan MENG . Structures and magnetism of dinuclear Co complexes based on imine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2212-2220. doi: 10.11862/CJIC.20240131
15. [15]
  Weilai Yu , Chuanbiao Bie . Unveiling S-Scheme Charge Transfer Mechanism. Acta Physico-Chimica Sinica, 2024, 40(4): 2307022-0. doi: 10.3866/PKU.WHXB202307022
16. [16]
  Hang Chen , Chengzhi Cui , Hebo Ye , Hanxun Zou , Lei You . Enhancing hydrolytic stability of dynamic imine bonds and polymers in acidic media with internal protecting groups. Chinese Chemical Letters, 2024, 35(5): 109145-. doi: 10.1016/j.cclet.2023.109145
17. [17]
  Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
18. [18]
  Xiaxia Xing , Xiaoyu Chen , Zhenxu Li , Xinhua Zhao , Yingying Tian , Xiaoyan Lang , Dachi Yang . Polyethylene imine functionalized porous carbon framework for selective nitrogen dioxide sensing with smartphone communication. Chinese Chemical Letters, 2024, 35(9): 109230-. doi: 10.1016/j.cclet.2023.109230
19. [19]
  Lulu He , Le Wang , Zhen He , Yiqian Yang , Cheng Heng Pang , Aiguo Wu , Bencan Tang , Juan Li . An imine-linked covalent organic framework with intrinsic photo-induced mitochondrial regulation for breast cancer therapy. Chinese Chemical Letters, 2025, 36(9): 110717-. doi: 10.1016/j.cclet.2024.110717
20. [20]
  Shunyu Wang , Yanan Zhu , Yang Zhao , Wanli Nie , Hong Meng . Steric effects and electronic manipulation of multiple donors on S₀/S₁ transition of D_n-A emitters. Chinese Chemical Letters, 2025, 36(4): 110555-. doi: 10.1016/j.cclet.2024.110555

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1166)
HTML views(15)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return