Citation: Yi WU, Qing-Mei YE, Shu-Qin QIN, Ren-Wang JIANG. Isolation, Crystal Structure and Cytotoxic Activity of Natural Maistemonine and Comparison with the Synthetic Compound[J]. Chinese Journal of Structural Chemistry, ;2020, 39(7): 1277-1282. doi: 10.14102/j.cnki.0254–5861.2011–2698 shu

Isolation, Crystal Structure and Cytotoxic Activity of Natural Maistemonine and Comparison with the Synthetic Compound

Yi WU ^{a, c, ②} ,
Qing-Mei YE ^{b, c, ②} ,
Shu-Qin QIN ^c ,
Ren-Wang JIANG ^c,,

a.
Zhongshan Torch Polytechnic, Zhongshan 528436, China
b.
Department of Pharmacy, Hainan General Hospital, Haikou 570311, China
c.
Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education, Jinan University, Guangzhou 510632, China

Corresponding author: Ren-Wang JIANG, trwjiang@jnu.edu.cn
Received Date: 11 December 2019
Accepted Date: 5 March 2020

Fund Project: Guangdong Key Scientific Project 2013A022100029Guangdong Characteristic Innovation Projects of Universities 2018GKTSCX055

Figures(5)

The title compound maistemonine (1) was isolated from the total alkaloid fraction of the 95% ethanol extract of the roots of Stemona japonica, followed by preparative HPLC and recrystallization from a mixture of n-hexane and ethyl acetate. The crystal structure of 1, C₂₃H₂₉NO₆, was determined by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic system, space group P2₁2₁2₁ with a = 8.5698(6), b = 14.0460(11), c = 17.8815(17) Å, V = 2152.4(3) Å³, Z = 4, M_r = 415.47, D_c = 1.282 g/cm³, λ = 0.71079 Å, μ = 0.092 cm^–1, F(000) = 888, S = 0.995, R = 0.0535 and wR = 0.1067. A total of 5136 unique reflections were collected, of which 3523 were observed (I > 2σ(I)). The absolute configuration of 1 could be assigned by referring to the conserved configuration of the methyl groups at C(2). Compound 1 shows mild cytotoxic activity against the prostate cancer cells LNCaP and PC3 with the IC₅₀ values of 29.4 ± 2.3 and 46.6 ± 3.1 μM, respectively. It is noteworthy that the natural maistemonine (1) is different from the synthetic compound which was a racemic with the triclinic space group P1. The lactone rings E from the natural and synthetic 1 are almost perpendicular to each other when overlapping the remaining parts of the molecules.
- maistemonine,
- isolation,
- crystal structure,
- cytotoxic,
- comparison,
- synthesis
1. [1]
  Pharmacopoeia commission of People's Republic of China. The Pharmacopoeia of the People's Republic of China, Part 1. Chemical Industry Publishing House, Beijing, China 2015, p204.
2. [2]
  Pilli, R. A.; Rossoa, G. B.; Oliveira, M. C. The chemistry of Stemona alkaloids: an update. Nat. Prod. Rep. 2010, 27, 1908–1937. doi: 10.1039/c005018k
3. [3]
  Greger, H. Structural relationships, distribution and biological activities of Stemona alkaloids. Planta Med. 2006, 72, 99–113. doi: 10.1055/s-2005-916258
4. [4]
  Quang, D. N.; Khamko, V. A.; Trang, N. T.; Yen, L. T. H.; Dien, P. H. Stemofurans X-Y from the roots of Stemona species from Laos. Nat. Prod. Commun. 2014, 9, 1741–1742.
5. [5]
  Yang, X. Z.; Zhu, J. Y.; Tang, C. P.; Ke, C. Q.; Lin, G.; Cheng, T. Y.; Rudd, J. A.; Ye, Y. Alkaloids from roots of Stemona sessilifolia and their antitussive activities. Planta Med. 2009, 75, 174–177. doi: 10.1055/s-0028-1088345
6. [6]
  Yi, M.; Xia, X.; Wu, H. Y.; Tian, H. Y.; Huang, C.; But, P. P. H.; Shaw, P. C.; Jiang, R. W. Structures and chemotaxonomic significance of stemona alkaloids from Stemona japonica. Nat. Prod. Commun. 2015, 10, 2097–2099.
7. [7]
  Li, S. L.; Jiang, R. W.; Hon, P. M.; Cheng, L.; Xu, H. X.; Greger, H.; But, P. P. H.; Shaw, P. C. Quality evaluation of Radix Stemonae through simultaneous quantification of bioactive alkaloids by high-performance liquid chromatography coupled with diode array and evaporative light scattering detectors. Biomed. Chromatogr. 2007, 21, 1088–1094. doi: 10.1002/bmc.862
8. [8]
  Chen, Z. H.; Chen, Z. M.; Yang, Y. Q.; Tu, Y. Q.; Zhang, F. M. Total synthesis of (±)-maistemonine, (±)-stemonamide, and (±)-isomaistemonine. J. Org. Chem. 2011, 76, 10173–10186. doi: 10.1021/jo202042x
9. [9]
  Jiang, R. W.; Hon, P. M.; But, P. P. H.; Chung, H. S.; Lin, G.; Ye, W. C.; Mak, T. C. W. Isolation and stereochemistry of two new alkaloids from Stemona tuberose Lour. Tetrahedron 2002, 58, 6705–6712. doi: 10.1016/S0040-4020(02)00678-6
10. [10]
  Jiang, R. W.; Hon, P. M.; Xu, Y. T.; Chan, Y. M.; Xu, H. X.; Shaw, P. C.; But, P. P. H. Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa. Phytochemistry 2006, 67, 52–57. doi: 10.1016/j.phytochem.2005.10.004
11. [11]
  Wu, Y.; Ye, Q. M.; Liu, J.; Xu, W.; Zhu, Z. R.; Jiang, R. W. Isolation, crystal structure and antitussive activity of 9S, 9aS-neotuberostemonine. Chin. J. Struct. Chem. 2018, 37, 571–576.
12. [12]
  Jiang, R. W.; Hon, P. M.; Zhou, Y.; Chan, Y. M.; Xu, Y. T.; Xu, H. X.; Greger, H.; Shaw, P. C.; But, P. P. H. Alkaloids and chemical diversity of Stemona tuberosa. J. Nat. Prod. 2006, 69, 749–754. doi: 10.1021/np050539g
13. [13]
  Jiang, R. W.; Ye, W. C.; Shaw, P. C.; But, P. P. H.; Mak, T. C. W. Absolute configuration of neostenine. J. Mol. Struct. 2010, 966, 18–22. doi: 10.1016/j.molstruc.2009.11.059
14. [14]
  Xu, Y. T.; Hon, P. M.; Jiang, R. W.; Cheng, L.; Li, S. H.; Chan, Y. P.; Xu, H. X.; Shaw, P. C.; But, P. P. H. Antitussive effects of Stemona tuberosa with different chemical profiles. J. Ethnopharmacol. 2006, 108, 46–53. doi: 10.1016/j.jep.2006.04.022
15. [15]
  Xu, Y. T.; Shaw, P. C.; Jiang, R. W.; Hon, P. M.; Chan, Y. M.; But, P. P. H. Antitussive and central respiratory depressant effects of Stemona tuberosa. J. Ethnopharmacol. 2010, 128, 679–684. doi: 10.1016/j.jep.2010.02.018
16. [16]
  Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods 1983, 65, 55–63. doi: 10.1016/0022-1759(83)90303-4
17. [17]
  Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford University Press, New York 1999.
18. [18]
  Brem, B.; Seger, C.; Pacher, T.; Hofer, O.; Vajrodaya, S.; Greger, H. Feeding dterrence and cntact toxicity of stemona alkaloids, a source of potent natural insecticides. J. Agric. Food Chem. 2002, 50, 6383–6388. doi: 10.1021/jf0205615
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
6. [6]
  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
7. [7]
  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
8. [8]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
9. [9]
  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
10. [10]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
11. [11]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
12. [12]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
13. [13]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
14. [14]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
15. [15]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
16. [16]
  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
17. [17]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
18. [18]
  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
19. [19]
  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
20. [20]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(343)
HTML views(5)

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