Citation: Wu-Wu LI, Min-Yan ZHENG, Yi-Hong GAO, Zun-Ting ZHANG. Argentum 5-Hydroxy-7-methoxy-2-phenyl- 4H-chromen-4-one-6-sulfonate: Synthesis, Crystal Structure and Antitumor Activity[J]. Chinese Journal of Structural Chemistry, ;2020, 39(10): 1898-1905. doi: 10.14102/j.cnki.0254–5861.2011–2791 shu

Argentum 5-Hydroxy-7-methoxy-2-phenyl- 4H-chromen-4-one-6-sulfonate: Synthesis, Crystal Structure and Antitumor Activity

a.
College of Chemistry & Chemical Engineering, Xianyang Normal University, Xianyang 712000, China
b.
Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China

Corresponding author: Wu-Wu LI, langyuan2012@126.com
Received Date: 2 March 2020
Accepted Date: 27 April 2020

Fund Project: Scientific Research Program Funded by Shaanxi Provincial Education Department 18JK0837Natural Science Basic Research Plan Funded by Shaanxi Province of China 2018JM2045Science and Technology Projects of Xianyang City 2017k02-19Scientific Research Project Funded by Xianyang Normal University XSYK18006Qing-Lan Talents Project Funded by Xianyang Normal University XSYQL201904

Figures(5)

In order to improve the water solubility and bioavailability of 5-hydroxy-7-methoxyflavone, argentum 5-hydroxy-7-methoxy-2-phenyl-4H-chromen-4-one-6-sulfonate [Ag₄(H₂O)₆](C₁₆H₁₁O₄SO₃)₄·H₂O (1, C₁₆H₁₁O₄SO₃ = 5-hydroxy-7-methoxy-2-phenyl-4H-chromen-4-one-6-sulfonate) was synthesized by sulfonation reaction. The structure of 1 was characterized by FT-IR, elemental analysis and X-ray single-crystal diffraction. Complex 1 belongs to the triclinic system, space group P\begin{document}$ \overline 1 $\end{document}, a = 8.077(4), b = 12.365(4), c = 17.735(7) Å, V = 1685.0(12) Å³, Z = 1, μ = 1.372 mm^–1, D_c = 1.936 g/cm³, F(000) = 984, the final R = 0.0819 and wR = 0.2332 with I > 2σ(I). 3D structure of 1 exhibits alternating organic and inorganic regions. O–H⋅⋅⋅O hydrogen bonds and Ag–O coordination interactions exist among crystal water, coordinated water and sulfo group, which constructed an organic zone. Flavone skeletons form organic region of 1. Sulfo group is the bridge linking these two regions. The in vitro antitumor activity of 1 against human lymphoma cells U937 and human breast cancer cells MCF-7 were evaluated with CCK-8 assay. The result shows that 1 showed inhibitory activity against tumour cell U937 and MCF-7, and indicated that flavone sulfonate derivatives may be potential leads for further biological screenings and may generate drug-like molecules.
- argentum 5-hydroxy-7-methoxy-2-phenyl-4H-chromen-4-one-6-sulfonate,
- sulfonation reaction,
- crystal structure,
- antitumor activity
1. [1]
  Chen, G. L.; Fan, M. X.; Wu, J. L.; Li, N.; Guo, M. Q. Antioxidant and anti-inflammatory properties of flavonoids from lotus plumule. Food Chem. 2019, 227, 706–712.
2. [2]
  Arts, I. C. W. A review of the epidemiological evidence on tea, flavonoids, and lung cancer. J. Nutr. 2008, 138, 1561S–1566S. doi: 10.1093/jn/138.8.1561S
3. [3]
  Spagnuolo, C.; Moccia, S.; Russo, G. L. Anti-inflammatory effects of flavonoids in neurodegenerative disorders. Eur. J. Med. Chem. 2018; 153, 105–115. doi: 10.1016/j.ejmech.2017.09.001
4. [4]
  Liu, Y. P.; Tong, J. M.; Tong, Y.; Li, P.; Cui, X. L.; Cao, H. B. In vitro anti-influenza virus effect of total flavonoid from Trollius ledebouri Reichb. J. Int. Med. Res. 2018, 46, 1380–1390. doi: 10.1177/0300060517750284
5. [5]
  Raffa, D.; Maggio, B.; Raimondi, M. V.; Plescia, F.; Daidone, G. Recent discoveries of anticancer flavonoids. Eur. J. Med. Chem. 2017, 142, 213–228. doi: 10.1016/j.ejmech.2017.07.034
6. [6]
  Marchand, L. L. Cancer preventive effects of flavonoids–a review. Biomed. Pharmacother. 2002, 56, 296–301. doi: 10.1016/S0753-3322(02)00186-5
7. [7]
  Lim, D. Y.; Jeong, Y.; Tyner, A. L.; Park, J. H. Induction of cell cycle arrest and apoptosis in HT-29 human colon cancer cells by the dietary compoundluteolin. Am. J. Physiol-Gastrointest Liver Physiol. 2007, 292, G66–G75. doi: 10.1152/ajpgi.00248.2006
8. [8]
  Tang, Q.; Ji, F. L.; Guo, J. L.; Wang, J. Y.; Li, Y. C.; Bao, Y. M. Directional modification of chrysin for exerting apoptosisand enhancing significantly anti-cancer effects of 10-hydroxycamptothecin. Biomed. Pharmacother 2016, 82, 693–703. doi: 10.1016/j.biopha.2016.06.008
9. [9]
  Pichichero, E.; Cicconi, R.; Mattei, M.; Muzi, M. G.; Canini, A. Acacia honey and chrysin reduce proliferation of melanomacells through alterations in cell cycle progression. Int. J. Oncol. 2010, 37, 973–981.
10. [10]
  Salah, N. M.; Souleman, A. M. A.; Shaker K. H.; Hawary S. E.; Elhady F. K. A. Acetylcholinesterase, alpha-Glucosidase and tyrosinase inhibitors from egyptian propolis. Int. J. Pharmacognosy and Phytochem. Res. 2017, 9, 528–536.
11. [11]
  Thao, N. P.; Luyen, B. T. T.; Kim, J. H.; Jo, A. R.; Yang, S. Y.; Dat, N. T.; Minh, C. V.; Kim, Y. H. Soluble epoxide hydrolase inhibitory activity by rhizomes of Kaempferia parviflora Wall. ex Baker. Med. Chem. Res. 2016, 25, 704–711. doi: 10.1007/s00044-016-1525-y
12. [12]
  Chen, F.; Li, H. L.; Tan, Y. F.; Li, Y. H.; Lai, W. Y.; Guan, W. W.; Zhang, J. Q.; Zhao, Y. S.; Qin, Z. M. Identification of known chemicals and their metabolites from Alpinia oxyphylla fruit extract in rat plasma using liquid chromatography/tandem mass spectrometry (LC-MS/MS) with selected reaction monitoring. J. Pharm. Biomed. Anal. 2014, 97, 166–177. doi: 10.1016/j.jpba.2014.04.037
13. [13]
  Kuo, W. L.; Liao, H. R.; Chen, J. J. Biflavans, flavonoids, and a dihydrochalcone from the stem wood of Muntingia calabura and their inhibitory activities on neutrophil pro-inflammatory responses. Molecules 2014, 19, 20521–20535. doi: 10.3390/molecules191220521
14. [14]
  Cao, X. D.; Ding, Z. S.; Jiang, F. S.; Ding, X. H.; Chen, J. Z.; Chen, S. H.; Lv, G. Y. Antitumor constituents from the leaves of Carya cathayensis. Nat. Prod. Res. 2012, 26, 2089–2094.
15. [15]
  Zhang, Q.; Cui, C.; Chen, C. Q.; Hu, X. L.; Liu, Y. H.; Fan, Y. H.; Meng, W. H.; Zhao, Q. C. Anti-proliferative and pro-apoptotic activities of Alpinia oxyphylla on HepG2 cells through ROS-mediated signaling pathway. J. Ethnopharmacol. 2015, 169, 99–108. doi: 10.1016/j.jep.2015.03.073
16. [16]
  Ahmed-Belkacem, A.; Pozza, A.; Muñoz-Martínez, F.; Bates, S. E.; Castanys, S.; Gamarro, F.; Di-Pietro, A.; Pérez-Victoria, J. M. Flavonoid structure-activity studies identify 6-prenylchrysin and tectochrysin as potent and specific inhibitors of breast cancer resistance protein ABCG2. Cancer Res. 2005, 65 4852–4860. doi: 10.1158/0008-5472.CAN-04-1817
17. [17]
  Oh, S. B.; Hwang, C. J.; Song, S. Y.; Jung, Y. Y.; Yun, H. M.; Sok, C. H.; Sung, H. C.; Yi, J. M.; Park, D. H.; Ham, Y. W.; Han, S. B.; Hwang, B. Y.; Hong, J. T. Anti-cancer effect of tectochrysin in NSCLC cells through overexpression of deathreceptor and inactivation of STAT3. Cancer Lett. 2014, 353, 95–103. doi: 10.1016/j.canlet.2014.07.007
18. [18]
  Park, M. H.; Hong, J. E.; Park, E. S.; Yoon, H. S.; Seo, D. W.; Hyun, B. K.; Han, S. B.; Ham, Y. W.; Hwang, B. Y.; Hong, J. T. Anticancer effect of tectochrysin in coloncancer cell via suppression of NF-kappaB activityand enhancement of death receptor expression. Mol. Cancer 2015, 14, 1–12.
19. [19]
  Hou, R.; Han, Y. X.; Fei, Q. L.; Gao, Y.; Qi, R. J.; Cai, R. L.; Qi, Y. Dietary flavone tectochrysin exerts anti-inflammatory action by directly inhibiting MEK1/2 in PS-primed macrophages. Mol. Nutr. Food Res. 2018, 62, 1700288. doi: 10.1002/mnfr.201700288
20. [20]
  Petrov, K. G.; Zhang, Y. M.; Carter, M.; Cockerill, G. S.; Dickerson, S.; Gauthier, C. A.; Guo, Y.; Mook-Jr, R. A.; Rusnak, D. W.; Walker, A. L.; Wood, E. R.; Lackey, K. E. Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series. Bioorg. Med. Chem. Lett. 2006, 16, 4686–4691. doi: 10.1016/j.bmcl.2006.05.090
21. [21]
  Sheldrick, G. M. SADABS, University of Göttingen, Germany 1996.
22. [22]
  Sheldrick, G. M. SHELX-97, Program Package for Crystal Structure Solution and Refinement. University of Göttingen, Germany 1997.
23. [23]
  Qian, M. K.; Yang, B. J.; Gu, W. H.; Chen, Z. X.; Chen, X. D; Ye, X. Q. Studies on the active principles of DAN-SHEN I. The structure of sodium tanshinone II-A sulfonate and methylene tanshinquinone. Acta Chim. Sinica 1978, 36, 199–206.
24. [24]
  Chen, W. Z.; Dong, Y. L.; Wang, C. G.; Ding, G. S. Pharmacological studies of sodium tanshinone II-A sulfonate. Acta Pharm. Sin. 1979, 14, 177–283.
25. [25]
  Chantrapromma, K.; Pakawatchai, C.; Skelton, B. W.; White, A. H.; Worapatamasri, S. 5-Hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one (tectochrysin) and 2, 5-dihydroxy-7-methoxy-2-phenyl-2, 3-dihydro-4H-1-benzo-pyran-4-one: isolation from Uvaria rufas and X-ray structures. Aust. J. Chem. 1989, 42, 2289–2293. doi: 10.1071/CH9892289
26. [26]
  Liu, H. Y.; Chi, Y. C.; Sun, H. M. Synthesis, crystal structure and luminescence of a novel one-dimensional silver(I) sulfonate complex with pyrazine ligand. Chin. J. Struct. Chem. 2001, 30, 211–215.
27. [27]
  Parthasarathy, R. Crystal structure of glycylglycine hydrochloride. Acta Cryst. 1969, B25, 509–518.
28. [28]
  Jeffrey, G. A.; Saenger, W. Hydrogen bonding in biological structures. Springer-Verlag, New York 1991.
1. [1]
  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
2. [2]
  Jiarong ZHU , Xiaohua ZHANG , Xinting XIONG , Xuliang NIE , Xiuying SONG , Miaomiao ZHANG , Dayong PENG , Xiuguang YI . Crystal structure, Hirshfeld surface analysis, and antifungal activity of five complexes based on 2,5-bis(carboxymethoxy)terephthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2358-2370. doi: 10.11862/CJIC.20250150
3. [3]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
4. [4]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
5. [5]
  Wenya DING , Fangfei XU , Jiayu GU , Xinran CHEN , Kai CHEN . Synthesis and crystal structure of three cucurbit[6]uril-cadmium supramolecular assemblies. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 808-816. doi: 10.11862/CJIC.20260012
6. [6]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
7. [7]
  Zhihui ZONG , Zijie ZHAO , Lei HUANG , Zhicheng PAN , Shan WANG , Lili LIANG , Huaqing LIU , Enli ZHANG . Synthesis, crystal structures, and antitumor activity of two metal complexes of imidazolyl acylhydrazones. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 1048-1062. doi: 10.11862/CJIC.20250330
8. [8]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
9. [9]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
10. [10]
  Lifang HE , Yaoze LUO , Qiying SHI , Jianxin TANG , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 632-640. doi: 10.11862/CJIC.20250244
11. [11]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
12. [12]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
13. [13]
  Chengyu JIANG , Xufeng LIU . Synthesis, structural characterization, electrocatalytic proton reduction, and fungicidal activity of thiazole-containing di-iron complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 355-364. doi: 10.11862/CJIC.20250253
14. [14]
  Ruiyan CHEN , Yanping HE , Jian ZHANG . Synthesis and third-order nonlinear optical property of Ti₄L₆ cage-based metal-organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2149-2156. doi: 10.11862/CJIC.20250177
15. [15]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
16. [16]
  Lihang LAN , Yanyong SHA , Lina YANG , Wentao DAI , Daozhen SHEN , Wenlong LIU , Hongjiang LIU , Qi LIU . A one-dimensional cadmium-based coordination polymer as cathode material of lithium-ion battery. Chinese Journal of Inorganic Chemistry, 2026, 42(8): 1751-1762. doi: 10.11862/CJIC.20260039
17. [17]
  Jing FENG , Renshu WANG , Hu WANG , Hailong LIU . Co(Ⅱ) and Ni(Ⅱ) complexes of 3,3-diphenylpropionic acid and 2,2′-dipyridylamine: Structures and biological activities. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 617-631. doi: 10.11862/CJIC.20250265
18. [18]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
19. [19]
  Xuetian WANG , Jijiang WANG , Long TANG , Erlin YUE , Xiao WANG , Yuqi ZHANG . A three-dimensional zinc(Ⅱ) metal-organic framework based on nitrogen-containing ligands for the detection of 2,4-dinitrophenylhydrazine and tetracycline. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 861-871. doi: 10.11862/CJIC.20250294
20. [20]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1996)
HTML views(196)

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