Synthesis, characterization and antiproliferative activity of regioselectively reduced and aminated derivatives of gambogic acid

doi:10.7503/cjcu20250320

Chem. J. Chinese Universities

• Article • Previous Articles Next Articles

Synthesis, characterization and antiproliferative activity of regioselectively reduced and aminated derivatives of gambogic acid

FENG Junjun^1,3，QI Mingli¹，MAO Weilong¹，WANG Jingxuan¹， CHEN Li^1,2

1. State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University 2. Haihe Laboratory of Sustainable Chemical Transformations 3. School of Pharmaceytical Engineering Jiangsu Food and Pharmaceutical Science College

Received:2025-10-31 Revised:2025-12-03 Online First:2025-12-03 Published:2025-12-03
Supported by:
Supported by the Natural Science Foundation of Tianjin(No. 23JCZDJC00260)

1. ESM to 20250320.pdf(4874KB)

Abstract

Abstract: We synthesized derivatives selectively reduced at the carboxyl group and the isolated carbonyl group for the first time, along with derivatives with an isomerized 27,28 carbon–carbon double bond and several reductively aminated compounds, which have different acid-base properties than gambogic acid. The structures and absolute configurations of all the compounds were determined by NMR and IR spectroscopy and HRMS. In in vitro cell proliferation assays against three human cancer cell lines (HL-60, BEL-7402, and A-549), all the tested compounds showed similar inhibitory activity as that of gambogic acid. This work may facilitate the development of structurally modified derivatives as potential anticancer drugs.

Key words: Gambogic acid, Aminated derivatives, Regioselective reduction, Antitumor activities, Cytotoxicity

CLC Number:

O629

TrendMD:

FENG Junjun, QI Mingli, MAO Weilong, WANG Jingxuan, CHEN Li. Synthesis, characterization and antiproliferative activity of regioselectively reduced and aminated derivatives of gambogic acid[J]. Chem. J. Chinese Universities, doi: 10.7503/cjcu20250320.

[1]	HE Rongrong, YOU Xin, ZHENG Xing, YANG Menghan, CHANG Tianjun. Engineering Stimuli-responsive RNA-cleaving DNAzymes in Organic Cosolvents [J]. Chem. J. Chinese Universities, 2025, 46(7): 20250010.
[2]	LIU Dongmei, XU Yuanqiang, XIA Chao, ZHENG Jingjing, SU Xianbin. Continuous Flow Liquid Phase Synthesis of Thymopentin Using Fluoride-labile Hydrophobic Tag [J]. Chem. J. Chinese Universities, 2025, 46(4): 20240544.
[3]	WANG Shihao, SHI Wanrui, LIU Yi, ZHANG Hao. Research Progress and Mechanism of cGAS-STING Pathway in Tumor Immunotherapy [J]. Chem. J. Chinese Universities, 2025, 46(1): 20240241.
[4]	ZHANG Nan, DENG Changxuan, LIN Hanlin, GAO Yangguang. Optimized Synthesis of Natural Product Penasulfate A， a Dual Inhibitor Against α -Glucosidase and Human Cancer Cells [J]. Chem. J. Chinese Universities, 2024, 45(12): 20240363.
[5]	LIU Hao, LIU Dongmei, SUN Haotian, XIA Chao, SU Xianbin. Continuous Flow Liquid-phase Vialox Peptide Synthesis Using Hydrophobic Silyl Tag [J]. Chem. J. Chinese Universities, 2024, 45(7): 20240024.
[6]	DONG Yuan, MA Yangmin, MA Siyue, SUN Renwei. Catalytic Synthesis of N-methylindopregnenolone Compounds Based on Diosgenin and Their Anti-tumor Activity [J]. Chem. J. Chinese Universities, 2024, 45(4): 20230449.
[7]	CUI Li, LI Suhui, ZHENG Xing, CHANG Tianjun, BING Tao. Effect of Metal Ions on the Catalytical Activity of a DMSO-dependent RNA-cleaving DNAzyme [J]. Chem. J. Chinese Universities, 2024, 45(4): 20240004.
[8]	MAN Lijuan, YE Jiajia, ZHANG Defeng, ZOU Zihua, HUANG Linjuan, WANG Zhongfu, WANG Chengjian. Preparative Release and Mass Spectrometric Analysis of Tn and T Antigens Existing in Sericin [J]. Chem. J. Chinese Universities, 2023, 44(12): 20230378.
[9]	MA Yifan, ZHANG Yamin, GAN Shengmin, ZHANG Yuchen, FEI Xian, WANG Ting, ZHANG Zeqi, GONG Xuezhu, ZHANG Haoli. Ternary Organic Photovoltaic Devices Based on Wide-band Gap Small Molecule Donor Third Component [J]. Chem. J. Chinese Universities, 2023, 44(9): 20230170.
[10]	HUANG Dingmin, SUN Haotian, WANG Zhenwei, LIU Hao, SU Xianbin. 3-Quinoline Boric Acid as an Efficient Catalyst for the Direct Amidation of Carboxylic Acids at Room Temperature [J]. Chem. J. Chinese Universities, 2023, 44(6): 20230004.
[11]	XU Yongbin, FENG Shuaixia, CHEN Jie, GONG Huan, SHI Songshan, WANG Huijun, WANG Shunchun. Structural Characterization of a Homogeneous Polysaccharide Isolated from the Flower of Carthamus Tinctorius L. and Its Inhibitory Activity on HepG2 Proliferation [J]. Chem. J. Chinese Universities, 2023, 44(4): 20220600.
[12]	CAO Shujie, LI Hongjun, GUAN Wenli, REN Mengtian, ZHOU Chuanzheng. Progress on the Stereocontrolled Synthesis of Phosphorothioate Oligonucleotides [J]. Chem. J. Chinese Universities, 2023, 44(3): 20220304.
[13]	HUAN Xinyu, LAI Ganqiang, HUANG Yue, YANG Caiguang. Research Progress on Chemical Intervention of N⁶-Methyladenosine Modification [J]. Chem. J. Chinese Universities, 2023, 44(3): 20220340.
[14]	ZHANG Kaisong, WANG Shaoru, ZHANG Yutong, TIAN Tian. Study of Epigenetic Modifications of Nucleic Acids Based on Supramolecular Chemistry [J]. Chem. J. Chinese Universities, 2023, 44(3): 20220335.
[15]	CHANG Liying, LING Xinyu, CHEN Heqi, WANG Xue, LIU Tao. Applications of Gene Editing in Mitochondrial Diseases [J]. Chem. J. Chinese Universities, 2023, 44(3): 20220363.

Synthesis, characterization and antiproliferative activity of regioselectively reduced and aminated derivatives of gambogic acid

PDF (PC)

Supplement

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments