Abstract
Two new compounds (1–2) and a new artificial product (3) together with fifteen known compounds (4–18) were isolated from Viscum coloratum (Kom.) Nakai. Their structures were established by analysis of their spectroscopic data including MS, 1D and 2D NMR spectra, and comparison with existing literature. All the compounds were assessed for their cytotoxic activity against 4T1 and LN229 cells (with cisplatin as the positive control), and the anti-LN229 cytotoxicity of compounds 3, 4 and 5 were greater than that of 4T1 cells.
Funding source: National Natural Science Foundation of China
Award Identifier / Grant number: U22A20370
Funding source: Heilongjiang Touyan Innovation Team Program
Award Identifier / Grant number: [2019]5
Funding source: Key Research and Development Projects of Heilongjiang Province
Award Identifier / Grant number: GA21D008
Funding source: Heilongjiang Province “Double First Class” Discipline Collaborative Innovation Achievement Construction Project
Award Identifier / Grant number: LJGXCG2022-096
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Research ethics: Not applicable.
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Informed consent: Not applicable.
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Author contributions: Bo Wen extracted, isolated and structurally analyzed compounds 1–18, and wrote manuscripts. Juan Pan guided the whole experimental process and operated the nuclear magnetic resonance instrument. Xin Meng carried out the cytotoxic experiment of compounds 1–18. Wei Guan determined its HR-ESI-MS spectrum. Zhi-Chao Hao guided cytotoxicity experiment. Hai-Xue Kang provided experimental funds. Qing-Shan Chen and Li-li Zhang contributed supervision. Yan Liu and Bing-You Yang designed the experiment and provided experimental funds. The authors have accepted responsibility for the entire content of this manuscript and approved its submission.
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Use of Large Language Models, AI and Machine Learning Tools: None declared.
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Conflict of interest: The authors state no conflict of interest.
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Research funding: This work was financially supported by the National Natural Science Foundation of China (U22A20370), Key Research and Development Projects of Heilongjiang Province (GA21D008), and Heilongjiang Touyan Innovation Team Program ([2019]5), and Heilongjiang Province “Double First Class” Discipline Collaborative Innovation Achievement Construction Project (LJGXCG2022-096).
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Data availability: The raw data can be obtained on request from the corresponding author.
References
1. Ma, Y, Fan, R, Duan, M, Yu, Z, Zhao, Y. A study of pharmacokinetic interactions among co-existing ingredients in Viscum coloratum after intravenous administration of three different preparations to rats. Phcog Mag 2015;11:455–62. https://doi.org/10.4103/0973-1296.160448.Search in Google Scholar PubMed PubMed Central
2. Yoo, JM, Park, KI, Ma, JY. Anticolitic effect of Viscum coloratum through suppression of mast cell activation. Am J Chin Med 2019:1–19. https://doi.org/10.1142/s0192415x19500101.Search in Google Scholar PubMed
3. Song, C, Wei, XY, Qiu, ZD, Gong, L, Yang, B, Ma, Y, et al.. Exploring the resources of the genus Viscum for potential therapeutic applications. J Ethnopharmacol 2021;277:114233. https://doi.org/10.1016/j.jep.2021.114233.Search in Google Scholar PubMed
4. Melo, MNDO, Batista, JVDC, Peñaloza, EMC, Oliveira, AP, Garrett, R, Baumgartner, S, et al.. A scoping review of genus Viscum: biological and chemical aspects of alcoholic extracts. Plants 2023;12:1811. https://doi.org/10.3390/plants12091811.Search in Google Scholar PubMed PubMed Central
5. He, XF, Wu, SL, Chen, JJ, Hu, J, Huang, XY, Li, TZ, et al.. New diarylheptanoid dimers as glp-1 secretagogues and multiple-enzyme inhibitors from Alpinia katsumadai. Bioorg Chem 2022;120:105653. https://doi.org/10.1016/j.bioorg.2022.105653.Search in Google Scholar PubMed
6. Zhang, M, Ju, YK, Mei, ZN, Xiong, H. Research on chemical composition of Begonia hubei. Green Sci Technol 2022;24:229–33.Search in Google Scholar
7. Ali, MS, Tezuka, Y, Awale, S, Banskota, AH, Kadota, S. Six new diarylheptanoids from the seeds of Alpinia blepharocalyx. J Nat Prod 2001;64:289–93. https://doi.org/10.1021/np000496y.Search in Google Scholar PubMed
8. Venkatesham, K, Reddy, SP, Chinnababu, B, Babu, KS. Stereoselective total synthesis of (3S,5S)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol, (3S,5S)-alpinikatin, and its diastereoisomers. Helv Chim Acta 2015;98:1307–14. https://doi.org/10.1002/hlca.201500073.Search in Google Scholar
9. Yang, L, Lin, J, Zhou, B, Liu, Y, Zhu, B. Activity of compounds from Taxillus sutchuenensis as inhibitors of HCV NS3 serine protease. Nat Prod Res 2017;31:487–91. https://doi.org/10.1080/14786419.2016.1190719.Search in Google Scholar PubMed
10. Ali, MS, Tezuka, Y, Banskota, AH, Kadota, S. Blepharocalyxins c-e, three new dimeric diarylheptanoids, and related compounds from the seeds of Alpinia blepharocalyx. J Nat Prod 2001;64:491–6. https://doi.org/10.1021/np000493l.Search in Google Scholar PubMed
11. Huang, HC, Hwang, SY, Liang, YH, Zhang, LL, Hsu, YW, Liaw, CC, et al.. Constituents from Taiwanese Sarcopyramis nepalensis. J Chin Med 2013;24:1–12.Search in Google Scholar
12. Shi, WZ, Chao, LP, Ruan, JY, Han, LF, Wang, T, Zhang, Y. Isolation and identification of flavonoids from the rhizomes of Rhizoma Mianbi. J Shenyang Pharm Univ 2017;34:124–30.Search in Google Scholar
13. Wang, Y, Chen, S, Lu, RP, Zhang, LS. Study on chemical constituents of Clematis chinensis. Chin Herb Med 2017;48:2619–24.Search in Google Scholar
14. Thu, VK, Thoa, NK, Van Kiem, P. Flavonoid glycosides from Viscum album. Vietnam J Chem 2016;54:443.Search in Google Scholar
15. Cao, D, Han, C, Gao, W, Cheng, L, Yang, P. Study on the chemical composition of mistletoe. Chin Herb Med 2016;47:4313–7.Search in Google Scholar
16. Park, HB, Lee, KH, Kim, KH, Lee, IK, Noh, HJ, Choi, SU, et al.. Lignans from the roots of Berberis amurensis. Nat Prod Sci 2009;15:17–21.Search in Google Scholar
17. Zhang, P, Zhang, C, Zeng, K, Jiang, Y, Tu, P. Lignans and flavonoids from Artemisia brachyloba. J Chin Pharmaceut Sci 2018;27:429–35. https://doi.org/10.5246/jcps.2018.06.043.Search in Google Scholar
18. Huang, XX, Gao, WY, Gu, KR, Ma, CY. Study on the chemical composition of Paris mairei H. Lév. Chin Herb Med 2009;40:1366–9.Search in Google Scholar
19. Xiao, SJ, Guo, DL, He, DH, Xia, B, Chen, F, Ding, LS, et al.. Study on chemical composition of Kiwi vine willow. Chin Herb Med 2016;47:383–7.Search in Google Scholar
20. Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, et al.. Gaussian 09, Revision D.01. Wallingford CT: Gaussian Inc.; 2010.Search in Google Scholar
21. Pescitelli, G, Bruhn, T. Good computational practice in the assignment of absolute configurations by TDDFT calculations of ECD spectra. Chirality 2016;28:466–74. https://doi.org/10.1002/chir.22600.Search in Google Scholar PubMed
22. Bruhn, T, Schaumlöffel, A, Hemberger, Y. SpecDis, Version 1.64, University of Wuerzburg 2015.Search in Google Scholar
Supplementary Material
This article contains supplementary material (https://doi.org/10.1515/znc-2023-0170).
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Articles in the same Issue
- Frontmatter
- Review Articles
- Ethnopharmacology and current conservational status of Cordyceps sinensis
- Review perspective on advanced nutrachemicals and anterior cruciate ligament rehabilitation
- Research Articles
- Cytotoxic compounds from Viscum coloratum (Kom.) Nakai
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