Bioactive prenylated phenolic compounds from the aerial parts of Glycyrrhiza uralensis
Open accessAbstract
In this work, a bioassay-guided fractionation strategy was used to isolate 26 phenolic compounds from the ethyl acetate partition of an ethanol extract of the aerial parts of Glycyrrhiza uralensis Fisch. ex DC. Among them, 8 prenylated phenolic compounds (glycyuralins Q-X) were described for the first time. The two enantiomers of glycyuralin Q were purified and their absolute configurations were established by ECD spectral calculations. (1″R, 2″S)-glycyuralin Q and (1″S, 2″R)-glycyuralin Q showed significant inhibitory activities against SARS-CoV-2 virus proteases 3CL pro with IC 50 values of 1.5 ± 1.0 and 4.0 ± 0.3 μM, and PL pro with IC 50 values of 2.4 ± 0.2 and 1.9 ± 0.1 μM, respectively. Four compounds showed potent cytotoxic activities against A549, Huh-7, and HepG2 human cancer cells with IC 50 values ranging from 0.5 to 2.5 μM.
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Glycyrrhiza glabra has antioxidant, anti-inflammatory, and neuroprotective effects in managing neurodegenerative disorders related to dementia.
“Moreover, GB has been found to have antioxidant, anti-inflammatory, and neuroprotective effects in the management of neurodegenerative disorders related to dementia [117,118].”
From Unlocking the Therapeutic Potential of Medicinal Plants for Alzheimer’s Disease: Preclinical to Clinical Trial Insights (2023) · cites this paper as [118]
Cites
AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility
Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009) · Journal of Computational Chemistry · doi:10.1002/jcc.21256 · Cited by 25,745 · see citing works
Bannwarth, C., Ehlert, S., & Grimme, S. (2019) · Journal of Chemical Theory and Computation · doi:10.1021/acs.jctc.8b01176 · Cited by 4,482 · see citing works
Structure-based design of antiviral drug candidates targeting the SARS-CoV-2 main protease
Dai, W., Zhang, B., Jiang, X.-M., Su, H., Li, J., Zhao, Y., Xie, X., Jin, Z., Peng, J., Liu, F., et al. (2020) · Science · doi:10.1126/science.abb4489 · Cited by 1,514 · see citing works
A comprehensive review on tyrosinase inhibitors
Zolghadri, S., Bahrami, A., Khan, M. T. H., Muñoz-Muñoz, J., Garcı́a-Molina, F., Garcı́a-Cánovas, F., & Saboury, A. A. (2019) · Journal of Enzyme Inhibition and Medicinal Chemistry · doi:10.1080/14756366.2018.1545767 · Cited by 1,092 · see citing works
Both Boceprevir and GC376 efficaciously inhibit SARS-CoV-2 by targeting its main protease
Fu, L., Ye, F., Feng, Y., Yu, F., Wang, Q., Wu, Y., Zhao, C., Sun, H., Huang, B., Niu, P., et al. (2020) · Nature Communications · doi:10.1038/s41467-020-18233-x · Cited by 544 · see citing works
Structure of papain-like protease from SARS-CoV-2 and its complexes with non-covalent inhibitors
Osipiuk, J., Azizi, S., Dvorkin, S., Endres, M. J., Jedrzejczak, R. P., Jones, K. A., Kang, S., Kathayat, R. S., Kim, Y., Lisnyak, V. G., et al. (2021) · Nature Communications · doi:10.1038/s41467-021-21060-3 · Cited by 471 · see citing works
Ji, S., Li, Z., Song, W., Wang, Y., Liang, W., Li, K., Tang, S., Wang, Q., Qiao, X., Zhou, D., et al. (2016) · Journal of Natural Products · doi:10.1021/acs.jnatprod.5b00877 · Cited by 242 · see citing works
Self-citationPharmacological Effects ofGlycyrrhizaspp. and Its Bioactive Constituents: Update and Review
Hosseinzadeh, H., & Nassiri‐Asl, M. (2015) · Phytotherapy Research · doi:10.1002/ptr.5487 · Cited by 228 · see citing works
Ma, C., Sacco, M. D., Xia, Z., Lambrinidis, G., Townsend, J. A., Hu, Y., Meng, X., Szeto, T., Ba, M., Zhang, X., et al. (2021) · ACS Central Science · doi:10.1021/acscentsci.1c00519 · Cited by 201 · see citing works
Demizu, S., Kajiyama, K., Takahashi, K., Hiraga, Y., YAMAMOTO, S., Tamura, Y., OKADA, K., & Kinoshita, T. (1988) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.36.3474 · Cited by 95 · see citing works
Biondi, D. M., Rocco, C., & Ruberto, G. (2003) · Journal of Natural Products · doi:10.1021/np020365s · Cited by 89 · see citing works
Glycybridins A–K, Bioactive Phenolic Compounds from Glycyrrhiza glabra
Li, K., Ji, S., Song, W., Kuang, Y., Lin, Y., Tang, S., Cui, Z.-X., Qiao, X., Yu, S., & Ye, M. (2017) · Journal of Natural Products · doi:10.1021/acs.jnatprod.6b00783 · Cited by 82 · see citing works
Self-citationPrenylated chalcones and flavones from the leaves of dorstenia kameruniana
Abegaz, B. M., Ngadjui, B. T., Dongo, É., et al. (1998) · Phytochemistry · doi:10.1016/s0031-9422(98)00061-2 · Cited by 74 · see citing works
Fan, J., Kuang, Y., Dong, Z., et al. (2020) · Journal of Natural Products · doi:10.1021/acs.jnatprod.9b00262 · Cited by 55 · see citing works
Self-citationDiterpenoids from Salvia miltiorrhiza and Their Immune-Modulating Activity
Wei, W., Zhou, P., Lin, C., et al. (2017) · Journal of Agricultural and Food Chemistry · doi:10.1021/acs.jafc.7b02384 · Cited by 52 · see citing works
Yu, X., & Li, S. (2011) · ChemBioChem · doi:10.1002/cbic.201100413 · Cited by 47 · see citing works
Nomura, T., Fukai, T., Wang, Q.-H., et al. (1990) · Heterocycles · doi:10.3987/com-89-5260 · Cited by 45 · see citing works
Four New Prenylated Flavonoids, Glyasperins A, B, C, and D from the Roots of Glycyrrhiza aspera
Nomura, T., Zeng, L., Fukai, T., et al. (1992) · Heterocycles · doi:10.3987/com-91-5951 · Cited by 39 · see citing works
Jiang, L., Akram, W., Luo, B., Hu, S., Faruque, M. O., Ahmad, S., Yasin, N. A., Khan, W. U., Ahmad, A., Shikov, A. N., et al. (2021) · Frontiers in Pharmacology · doi:10.3389/fphar.2021.658670 · Cited by 38 · see citing works
Flavonoids from Dittrichia viscosa
Chiappini, I., Fardella, G., Menghini, A. R., et al. (1982) · Planta Medica · doi:10.1055/s-2007-971429 · Cited by 37 · see citing works
Li, J., Chen, R., Wang, R., et al. (2014) · ChemBioChem · doi:10.1002/cbic.201402160 · Cited by 36 · see citing works
Ye, R., Fan, Y., & Ma, C. (2016) · Journal of Agricultural and Food Chemistry · doi:10.1021/acs.jafc.6b04155 · Cited by 36 · see citing works
C-prenylated flavonoids with potential cytotoxic activity against solid tumor cell lines
Molčanová, L., Janošíková, D., Acqua, S. D., & Šmejkal, K. (2019) · Phytochemistry Reviews · doi:10.1007/s11101-019-09641-z · Cited by 36 · see citing works
Fan, Y., Ye, R., Xu, H., et al. (2019) · Journal of Food Science · doi:10.1111/1750-3841.14592 · Cited by 27 · see citing works
Specialized metabolite profiling of different Glycyrrhiza glabra organs by untargeted UHPLC-HRMS
Celano, R., Docimo, T., Piccinelli, A. L., Rizzo, S., Campone, L., Sanzo, R. D., Carabetta, S., Rastrelli, L., & Russo, M. (2021) · Industrial Crops and Products · doi:10.1016/j.indcrop.2021.113688 · Cited by 25 · see citing works
Simirgiotis, M. J., Quispe, C., Bórquez, J., et al. (2016) · Industrial Crops and Products · doi:10.1016/j.indcrop.2016.08.037 · Cited by 24 · see citing works
Sixteen New Prenylated Flavonoids from the Fruit of Sinopodophyllum hexandrum
Sun, Y., Chen, H., Wang, J., et al. (2019) · Molecules · doi:10.3390/molecules24173196 · Cited by 19 · see citing works
Flavonoid aglycones of Oxytropis falcata
Huan, Y., Wang, D., Li, T., et al. (2009) · Chemistry of Natural Compounds · doi:10.1007/s10600-009-9291-4 · Cited by 14 · see citing works
Nomura, T., & Fukai, T. (1992) · Heterocycles · doi:10.3987/com-92-6026 · Cited by 11 · see citing works
Ji, S., Qiao, X., Li, Z., et al. (2015) · RSC Advances · doi:10.1039/c5ra06452j · Cited by 9 · see citing works
Self-citationNdom, J., Mbafor, J. T., Fomum, Z. T., et al. (1993) · Magnetic Resonance in Chemistry · doi:10.1002/mrc.1260310211 · Cited by 7 · see citing works
Note: A New Flavone from Hypericum Wightianum
Tao, S., & Wu, F.-E. (2004) · Journal of Asian Natural Products Research · doi:10.1080/10286020310001595935 · Cited by 4 · see citing works
[Isoflavones from Glycyrrhiza eurycarpa].
Zhang, Y. M., Xu, X. D., Hu, B., et al. (1997) · PubMed · Cited by 4 · see citing works
Four New Prenylated Flavonoids from the Fruits of Sinopodophyllum hexandrum
Sun, Y., Han, R., Zhao, C. X., et al. (2020) · Chemistry of Natural Compounds · doi:10.1007/s10600-020-03162-4 · Cited by 4 · see citing works
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Nagori, K., Nakhate, K. T., Yadav, K., Ajazuddin, & Pradhan, M. (2023) · Future Pharmacology · doi:10.3390/futurepharmacol3040053 · Cited by 61 · see citing works
- Authors
- Hasan, A., Zhang, M., Shang, Z.-P., Yi, Y., Kuang, Y., Yu, R., Fan, J.-J., Huang, Y.-X., Nijat, D., Qiao, X., & Ye, M.
- Affiliations
- Peking University (CN)
- Corresponding author
- Qiao, Xue
- Ye, Min
- Venue
- Phytochemistry
- Publisher
- Elsevier BV
- Published
- 2022-09
- Volume
- 201
- Pages
- 113284
- ISSN
- 0031-9422 (ISSN-L)
- OpenAlex
- W4282935592
- Cited by
- 15
- References
- 34
- Citations by year
- 2026: 4 · 2025: 3 · 2024: 4 · 2023: 3 · 2022: 1
- FWCI
- 2.52
- Type
- journal article
- Language
- en
- Open access
- green
- zenodo.org
- Licence
- Locations
- Phytochemistry (publishedVersion)
- PubMed (publishedVersion)
- Zenodo (CERN European Organization for Nuclear Research) (submittedVersion)
- Funders
- Science and Technology Department of Xinjiang Uygur Autonomous Region (2018AB012)
- National Natural Science Foundation of China (81891010 / 81891011)
- National Natural Science Foundation of China National Outstanding Youth Science Fund Project (81725023)
- Topics
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacological Effects of Natural Compounds
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive natural compounds
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Keywords
- Glycyrrhiza uralensis, enantiomers, absolute configuration, bioassay-guided fractionation, 3CLpro, papain-like protease, antiviral activity, cytotoxicity, anticancer activity, aerial parts
- MeSH terms
- COVID-19, SARS-CoV-2, Glycyrrhiza, Humans, Phenols, Glycyrrhiza uralensis, Plant Components, Aerial
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