Molecular networking-guided isolation strategy of a new C-glycosyl flavone rotamer from Stellaria alsine and evaluation of anti-inflammatory and antioxidant activities.
Interleukin-8
Molecular docking
Molecular networking
ROS
Rotamer
Stellaria alsine
Journal
Metabolomics : Official journal of the Metabolomic Society
ISSN: 1573-3890
Titre abrégé: Metabolomics
Pays: United States
ID NLM: 101274889
Informations de publication
Date de publication:
05 09 2023
05 09 2023
Historique:
received:
20
04
2023
accepted:
21
08
2023
medline:
7
9
2023
pubmed:
6
9
2023
entrez:
5
9
2023
Statut:
epublish
Résumé
Stellaria alsine has traditionally been used as both a famine relief food and an alternative medicine in East Asia. Modern pharmacological studies have revealed that S. alsine has various biological effects such as anticancer, anti-hepatoma, anti-inflammatory, and antioxidative effects. However, the anti-inflammatory properties of chemical constituents derived from this plant have not been studied well. To identify potential therapeutic candidate for treating inflammatory diseases such as inflammatory bowel disease (IBD). The distribution of chemical compounds was investigated by Global Natural Product Social (GNPS)-based molecular networking (MN) analysis using UPLC-Orbitrap tandem mass spectrometry. The anti-inflammatory and antioxidative effects of S. alsine extracts and fractions were evaluated by measuring interleukin (IL)-8 and reactive oxygen species (ROS) productions. The active EA layer of S. alsine showed the highest percentage of major compounds by feature-based molecular networking. The top candidate structures of EA fraction were rapidly annotated as flavone C- or O-glycosides via an advanced analysis tool, Network Annotation Propagation (NAP). With the GNPS molecular networking-guided isolation strategy, a new C-glycosyl flavone rotamer (1) was isolated. The structures of the major (1a) and minor (1b) rotational isomers were determined by extensive NMR analysis and MS/MS fragmentation. Finally, the anti-inflammatory activity of 1 was predicted by molecular docking simulations with IL-8 protein. These results suggested that the compound 1 is a potential therapeutic candidate for inflammatory bowel disease (IBD).
Identifiants
pubmed: 37670170
doi: 10.1007/s11306-023-02042-6
pii: 10.1007/s11306-023-02042-6
doi:
Substances chimiques
Antioxidants
0
Flavones
0
Anti-Inflammatory Agents
0
Biological Products
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
79Informations de copyright
© 2023. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.
Références
Amen, Y., Elsbaey, M., Othman, A., Sallam, M., & Shimizu, K. (2021). Naturally occurring chromone glycosides: Sources, bioactivities, and spectroscopic features. Molecules, 26, 7646. https://doi.org/10.3390/molecules26247646
doi: 10.3390/molecules26247646
pubmed: 34946728
Beniddir, M. A., Kang, K. B., Genta-Jouve, G., Huber, F., Rogers, S., & van der Hooft, J. J. J. (2021). Advances in decomposing complex metabolite mixtures using substructure- and network-based computational metabolomics approaches. Natural Product Reports, 38, 1967–1993. https://doi.org/10.1039/d1np00023c
doi: 10.1039/d1np00023c
pubmed: 34821250
Cai, Z., Wang, S., & Li, J. (2021). Treatment of inflammatory bowel disease: A comprehensive review. Frontiers in Medicine, 8, 765474. https://doi.org/10.3389/fmed.2021.765474
doi: 10.3389/fmed.2021.765474
pubmed: 34988090
Cao, J., Yin, C., Qin, Y., Cheng, Z., & Chen, D. (2014). Approach to the study of flavone di-C-glycosides by high performance liquid chromatography-tandem ion trap mass spectrometry and its application to characterization of flavonoid composition in Viola yedoensis. Journal of Mass Spectrometry, 49, 1010–1024. https://doi.org/10.1002/jms.3413
doi: 10.1002/jms.3413
pubmed: 25303391
Chen, S., Guang, G., Liao, W., Gong, S., Xiao, J., Bai, J., Wendy Hsiao, W. L., Li, N., & Wu, J. L. (2021). Discovery of the bioactive peptides secreted by Bifidobacterium using integrated MCX coupled with LC-MS and feature-based molecular networking. Food Chemistry, 347, 129008. https://doi.org/10.1016/j.foodchem.2021.129008
doi: 10.1016/j.foodchem.2021.129008
pubmed: 33484958
Choi, S. Y., Park, J., Kim, J., Lee, J., & Yang, H. (2021). Investigation of chemical profiles of different parts of Morus alba using a combination of molecular networking methods with mass spectral data from two ionization modes of LC/MS. Plants, 10, 1711. https://doi.org/10.3390/plants10081711
doi: 10.3390/plants10081711
pubmed: 34451756
da Silva, R. R., Wang, M., Nothias, L. F., van der Hooft, J. J. J., Caraballo-Rodríguez, A. M., Fox, E., Balunas, M. J., Klassen, J. L., Lopes, N. P., & Dorrestein, P. C. (2018). Propagating annotations of molecular networks using in silico fragmentation. PLOS Computational Biology, 14, e1006089. https://doi.org/10.1371/journal.pcbi.1006089
doi: 10.1371/journal.pcbi.1006089
pubmed: 29668671
Farag, M. A., Hegazi, N. M., & Donia, M. S. (2020). Molecular networking based LC/MS reveals novel biotransformation products of green coffee by ex vivo cultures of the human gut microbiome. Metabolomics, 16, 86. https://doi.org/10.1007/s11306-020-01704-z
doi: 10.1007/s11306-020-01704-z
pubmed: 32748036
Flores, G., Dastmalchi, K., Dabo, A. J., Whalen, K., Pedraza-Penalosa, P., Foronjy, R. F., D’Armiento, J. M., & Kennelly, E. J. (2012). Antioxidants of therapeutic relevance in COPD from the neotropical blueberry Anthopterus wardii. Food Chemistry, 131, 119–125. https://doi.org/10.1016/j.foodchem.2011.08.044
doi: 10.1016/j.foodchem.2011.08.044
pubmed: 22363097
Fox Ramos, A. E., Evanno, L., Poupon, E., Champy, P., & Beniddir, M. A. (2019). Natural products targeting strategies involving molecular networking: Different manners, one goal. Natural Product Reports, 36, 960–980. https://doi.org/10.1039/c9np00006b
doi: 10.1039/c9np00006b
pubmed: 31140509
Furuta, T., Kimura, T., Kondo, S., Mihara, H., Wakimoto, T., Nukaya, H., Tsuji, K., & Tanaka, K. (2004). Concise total synthesis of flavone C-glycoside having potent anti-inflammatory activity. Tetrahedron, 60, 9375–9379. https://doi.org/10.1016/j.tet.2004.08.015
doi: 10.1016/j.tet.2004.08.015
Kang, K. B., Woo, S., Ernst, M., van der Hooft, J. J. J., Nothias, L. F., da Silva, R. R., Dorrestein, P. C., Sung, S. H., & Lee, M. (2020). Assessing specialized metabolite diversity of Alnus species by a digitized LC-MS/MS data analysis workflow. Phytochemistry, 173, 112292. https://doi.org/10.1016/j.phytochem.2020.112292
doi: 10.1016/j.phytochem.2020.112292
pubmed: 32062198
Kim, C.-K., Yu, J., & Lee, M. (2023). Molecular networking-guided isolation of a phenolic constituent from Prunus mume seed and its antioxidant and anti-inflammatory activities. Foods, 12, 1146. https://doi.org/10.3390/foods12061146
doi: 10.3390/foods12061146
pubmed: 36981073
Larionova, M., Spengler, I., Nogueiras, C., Quijano, L., Ramírez-Gualito, K., Cortés-Guzmán, F., Cuevas, G., & Calderón, J. S. (2010). A C-Glycosylflavone from Piper ossanum, a compound conformationally controlled by CH/π and other weak intramolecular interactions. Journal of Natural Products, 73, 1623–1627. https://doi.org/10.1021/np100004v
doi: 10.1021/np100004v
pubmed: 20879757
Le Daré, B., Ferron, P. J., Allard, P. M., Clément, B., Morel, I., & Gicquel, T. (2020). New insights into quetiapine metabolism using molecular networking. Scientific Reports, 10, 19921. https://doi.org/10.1038/s41598-020-77106-x
doi: 10.1038/s41598-020-77106-x
pubmed: 33199804
Oladeji, O. S., & Oyebamiji, A. K. (2020). Stellaria media (L.) Vill.- A plant with immense therapeutic potentials: phytochemistry and pharmacology. Heliyon, 6, e04150. https://doi.org/10.1016/j.heliyon.2020.e04150
doi: 10.1016/j.heliyon.2020.e04150
pubmed: 32548330
Otify, A. M., Mohamed, O. G., El-Amier, Y. A., Saber, F. R., Tripathi, A., & Younis, I. Y. (2023). Bioherbicidal activity and metabolic profiling of allelopathic metabolites of three cassia species using UPLC-qTOF-MS/MS and molecular networking. Metabolomics, 19, 16. https://doi.org/10.1007/s11306-023-01980-5
doi: 10.1007/s11306-023-01980-5
pubmed: 36892715
Pal, P. P., Begum, A. S., Basha, S. A., Araya, H., & Fugimoto, Y. (2023). New natural pro-inflammatory cytokines (TNF-α, IL-6 and IL-1β) and iNOS inhibitors identified from Penicillium polonicum through in vitro and in vivo studies. International Immunopharmacology, 117, 109940. https://doi.org/10.1016/j.intimp.2023.109940
doi: 10.1016/j.intimp.2023.109940
Pluskal, T., Castillo, S., Villar-Briones, A., & Oresic, M. (2010). MZmine 2: Modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data. BMC Bioinformatics, 11, 395. https://doi.org/10.1186/1471-2105-11-395
doi: 10.1186/1471-2105-11-395
pubmed: 20650010
Qiu, L., Jiao, Y., Xie, J.-Z., Huang, G.-K., Qiu, S.-L., Miao, J.-H., & Yao, X.-S. (2013). Five new flavonoid glycosides from Nervilia fordii. Journal of Asian Natural Products Research, 15, 589–599. https://doi.org/10.1080/10286020.2013.790377
doi: 10.1080/10286020.2013.790377
pubmed: 23659497
Quinn, R. A., Nothias, L. F., Vining, O., Meehan, M., Esquenazi, E., & Dorrestein, P. C. (2017). Molecular networking as a drug discovery, drug metabolism, and precision medicine strategy. Trends in Pharmacological Sciences, 38, 143–154. https://doi.org/10.1016/j.tips.2016.10.011
doi: 10.1016/j.tips.2016.10.011
pubmed: 27842887
Rauter, A. P., Lopes, R. G., & Martins, A. (2007). C-Glycosylflavonoids: Identification, bioactivity and synthesis. Natural Product Communications, 2, 1175–1196. https://doi.org/10.1177/1934578X0700201125
doi: 10.1177/1934578X0700201125
Rayyan, S., Fossen, T., & Anderson, Ø. M. (2005). Flavone C-glycosides from leaves of Oxalis triangularis. Journal of Agricultural and Food Chemistry, 53, 10057–10060. https://doi.org/10.1021/jf051626h
doi: 10.1021/jf051626h
pubmed: 16366694
Shannon, P., Markiel, A., Ozier, O., Baliga, N. S., Wang, J. T., Ramage, D., Amin, N., Schwikowski, B., & Ideker, T. (2003). Cytoscape: A software environment for integrated models of biomolecular interaction networks. Genome Research, 13, 2498–2504. https://doi.org/10.1101/gr.1239303
doi: 10.1101/gr.1239303
pubmed: 14597658
Singh, A., Kukreti, R., Saso, L., & Kukreti, S. (2019). Oxidative stress: A key modulator in neurodegenerative diseases. Molecules, 24, 1583. https://doi.org/10.3390/molecules24081583
doi: 10.3390/molecules24081583
pubmed: 31013638
Singh, R., Chaudhary, M., & Chauhan, E. S. (2022). Stellaria media Linn.: A comprehensive review highlights the nutritional, phytochemistry, and pharmacological activities. Journal of Herbmed Pharmacology, 11, 330–338. https://doi.org/10.34172/jhp.2022.38
doi: 10.34172/jhp.2022.38
Skov, L., Beurskens, F. J., Zachariae, C. O., Reitamo, S., Teeling, J., Satijn, D., Knudsen, K. M., Boot, E. P., Hudson, D., Baadsgaard, O., Parren, P. W., & van de Winkel, J. G. (2008). IL-8 as antibody therapeutic target in inflammatory diseases: Reduction of clinical activity in palmoplantar pustulosis. Journal of Immunology, 181, 669–679. https://doi.org/10.4049/jimmunol.181.1.66
doi: 10.4049/jimmunol.181.1.66
Suo, S. K., Zheng, S. L., Chi, C. F., Luo, H. Y., & Wang, B. (2022). Novel angiotensin-converting enzyme inhibitory peptides from tuna byproducts-milts: Preparation, characterization, molecular docking study, and antioxidant function on H
doi: 10.3389/fnut.2022.957778
pubmed: 35938100
Wang, M., Carver, J. J., Phelan, V., Sanchez, L., Garg, N., Peng, Y., Nguyen, D. D., Watrous, J., Kapono, C. A., Luzzatto-Knaan, T., Porto, C., Bouslimani, A., Melnik, A. V., Meehan, M. J., Liu, W. T., Crüsemann, M., Boudreau, P. D., Esquenazi, E., … Bandeira, N. (2016). Sharing and community curation of mass spectrometry data with global natural products social molecular networking. Nature Biotechnology, 34, 828–837. https://doi.org/10.1038/nbt.3597
doi: 10.1038/nbt.3597
pubmed: 27504778
Wang, Q., Wu, X., Zhang, J., Song, M., Du, J., Cui, Y., & Li, Y. (2023). Role of ROS/JAK2/STAT3 signaling pathway in di-n-butyl phthalate-induced testosterone synthesis inhibition and antagonism of lycopene. Food and Chemical Toxicology, 175, 113741. https://doi.org/10.1016/j.fct.2023.113741
doi: 10.1016/j.fct.2023.113741
pubmed: 36958386
Whaley, A. K., Ebrahim, W., El-Neketi, M., Ancheeva, E. U., Özkaya, F. C., Pryakhina, N. I., Sipkina, N. U., Luzhanin, V. G., Liu, Z., & Proksch, P. (2017). New acetylated flavone C-glycosides from Iris lactea. Tetrahedron Letters, 58, 2171–2173. https://doi.org/10.1016/j.tetlet.2017.04.080
doi: 10.1016/j.tetlet.2017.04.080
Zhou, G., Yan, R., Wang, X., Li, S., Lin, J., Liu, J., & Zhao, Z. (2019). The overlooked rotational isomerism of C-glycosyl flavonoids. Phytochemistry Reviews, 18, 443–461. https://doi.org/10.1007/s11101-019-09601-7
doi: 10.1007/s11101-019-09601-7