Published February 28, 2022
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13,13a-seco-protoberberines from the tubers of Corydalis yanhusuo and their anti-inflammatory activity
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- 1. , Dong-Jie Fang & , Huan Xia & , Ya-Nan Wang & ** , Sheng Lin & * & Key Laboratory of Chinese Internal Medicine of Ministry of Education and Beijing, Dongzhimen Hospital, Beijing University of Chinese Medicine, Beijing, 100700, China & , Dong-Jie Fang & , Ling-Yan Wang
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Xia, Gui-Yang, Fang, Dong-Jie, Wang, Ling-Yan, Xia, Huan, Wang, Ya-Nan, Shang, Hong-Cai, Lin, Sheng (2022): 13,13a-seco-protoberberines from the tubers of Corydalis yanhusuo and their anti-inflammatory activity. Phytochemistry (113023) 194: 113023, DOI: 10.1016/j.phytochem.2021.113023, URL: http://dx.doi.org/10.1016/j.phytochem.2021.113023
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- urn:lsid:plazi.org:pub:FFC2FFA98D2ACF7CFFD3FFC2FFF9EB19
References
- Chan, S.C., 2000. Chingazumianine, a novel dichlorinated alkaloid from Corydalis koidzumiana. Helv. Chim. Acta 83, 2993-2999. https://doi.org/10.1002/1522-2675 (20001108)83:11<2993::AID-HLCA2993>3.0.CO;2-A.
- Cheng, X.Y., Shi, Y., Zheng, S.L., Jin, W., Sun, H., 2008. Two new protoberberine quaternary alkaloids from Corydalis yanhusuo. J. Asian Nat. Prod. Res. 10, 1117-1121. https://doi.org/10.1080/10286020802410615.
- Colombo, M.L., Bugatti, C., Mossa, A., Pescalli, N., Piazzoni, L., Pezzoni, G., Menta, E., Spinelli, S., Johnson, F., Gupta, R.C., Dasaradhi, L., 2002. Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine. Il Farmaco 56, 403-409. https://doi.org/10.1016/S0014-827X(01)01121-1.
- Deng, A.P., Zhang, Y., Zhou, L., Kang, C.Z., Lv, C.G., Kang, L.P., Nan, T.G., Zhan, Z.L., Guo, L.P., Huang, L.Q., 2021. Systematic review of the alkaloid constituents in several important medicinal plants of the genus Corydalis. Phytochemistry 183, 112644. https://doi.org/10.1016/j.phytochem.2020.112644.
- Fricker, M., Gibson, P.G., 2017. Macrophage dysfunction in the pathogenesis and treatment of asthma. Eur. Respir. J. 50, 1700196. https://doi.org/10.1183/ 13993003.00196-2017.
- Garcin, E.D., Arvai, A.S., Rosenfeld, R.J., Kroeger, M.D., Crane, B.R., Andersson, G., Andrews, G., Hamley, P.J., Mallinder, P.R., Nicholls, D.J., St-Gallay, S.A., Tinker, A. C., Gensmantel, N.P., Mete, A., Cheshire, D.R., Connolly, S., Stuehr, D.J., Aberg, A., Wallace, A.V., Tainer, J.A., Getzoff, E.D., 2008. Anchored plasticity opens doors for selective inhibitor design in nitric oxide synthase. Nat. Chem. Biol. 4, 700-707. https://doi.org/10.1038/nchembio.115.
- Karimov, A., Faskhutdinov, M.F., Abdullaev, N.D., Levkovich, M.G., Mil' grom, E.G., Rashkes, Y.V., Shakirov, R., 1993. Berberis alkaloids XXXII. berberal-A new alkaloid from Berberis heterobotrys. Chem. Nat. Compd. 29 (6), 774-777. https://doi.org/ 10.1007/BF00629649.
- Karin, M., Ben-Neriah, Y., 2000. Phosphorylation meets ubiquitination: the control of NF-κB activity. Annu. Rev. Immunol. 18, 621-663. https://doi.org/10.1146/ annurev.immunol.18.1.621.
- Kim, J.H., Ryu, Y.B., Lee, W.S., Kim, Y.H., 2014. Neuraminidase inhibitory activities of quaternary isoquinoline alkaloids from Corydalis turtschaninovii rhizome. Bioorg. Med. Chem. 22, 6047-6052. https://doi.org/10.1016/j.bmc.2014.09.004.
- Kwon, I.S., Kwak, J.H., Pyo, S., Lee, H.W., Kim, A., Schmitz, F.J., 2017. Oscarellin, an anthranilic acid derivative from a philippine sponge, Oscarella stillans, as an inhibitor of inflammatory cytokines in macrophages. J. Nat. Prod. 80, 149-155. https://doi. org/10.1021/acs.jnatprod.6b00787.
- Li, S.H., Li, L., Yang, R.N., Liang, S.D., 2020. Compounds of traditional Chinese medicine and neuropathic pain. Chin. J. Nat. Med. 18, 28-35. https://doi.org/10.1016/ S1875-5364(20)30002-9.
- Liu, Y., Fang, S., Li, X., Feng, J., Du, J., Guo, L., Su, Y., Zhou, J., Ding, G., Bai, Y., Wang, S., Wang, H., Liu, Y., 2017. Aspirin inhibits LPS-induced macrophage activation via the NF-κB pathway. Sci. Rep. 7, 11549. https://doi.org/10.1038/ s41598-017-10720-4.
- Ma, B.L., Ma, Y.M., Shi, R., Wang, T.M., Zhang, N., Wang, C.H., Yang, Y., 2010. Identification of the toxic constituents in rhizoma coptidis. J. Ethnopharmacol. 128, 357-364. https://doi.org/10.1016/j.jep.2010.01.047.
- Medzhitov, R., 2010. Inflammation 2010: new adventures of an old flame. Cell 140, 771-776. https://doi.org/10.1016/j.cell.2010.03.006.
- Miyazawa, M., Yoshio, K., Ishikawa, Y., Kameoka, H., 1998. Insecticidal alkaloids from Corydalis bulbosa against Drosophila melanogaster. J. Agric. Food Chem. 46, 1914-1919. https://doi.org/10.1021/jf9701897.
- Moghaddam, A.S., Mohammadian, S., Vazini, H., Taghadosi, M., Esmaeili, S., Mardani, F., Seifi, B., Mohammadi, A., Afshari, J.T., Sahebkar, A., 2018. Macrophage plasticity, polarization, and function in health and disease. J. Cell. Physiol. 233, 6425-6440. https://doi.org/10.1002/jcp.26429.
- Okamoto, T., Sanda, T., Asamitsu, K., 2007. NF-kappa B signaling and carcinogenesis. Curr. Pharmaceut. Des. 13, 447-462. https://doi.org/10.2174/ 138161207780162944.
- Ruan, Q.F., Pan, W.C., Zhao, M., Tang, Y.Q., Chen, X.J., Bai, J.Y., Jin, J., Cui, H., Zhao, Z. X., 2021. Butyrolactone and sesquiterpene derivatives as inhibitors of iNOS from the roots of Lindera glauca. Bioorg. Chem. 111, 104871. https://doi.org/10.1016/j. bioorg.2021.104871.
- Saradna, A., Do, D.C., Kumar, S., Fu, Q.L., Gao, P., 2018. Macrophage polarization and allergic asthma. Transl. Res. 191, 1-14. https://doi.org/10.1016/j.trsl.2017.09.002.
- Sener, B., Temizer, H., 1988. Chemical study on protoberberine alkaloids from Corydalis solida ssp. Brachyloba. Planta Med. 54, 584. https://doi.org/10.1055/s-2006- 962602.
- Singh, S., Singh, T.D., Singh, V.P., Pandey, V.B., 2010. Quaternary alkaloids of Argemone mexicana. Pharm. Biol. 48, 158-160. https://doi.org/10.3109/ 13880200903062622.
- Skeoch, S., Bruce, I.N., 2015. Atherosclerosis in rheumatoid arthritis: is it all about inflammation? Nat. Rev. Rheumatol. 11, 390-400. https://doi.org/10.1038/ nrrheum.2015.40.
- Soysal, P., Arik, F., Smith, L., Jackson, S.E., Isik, A.T., 2020. Inflammation, frailty and cardiovascular disease. Adv. Exp. Med. Biol. 1216, 55-64. https://doi.org/10.1007/ 978-3-030-33330-0_7.
- Tang, Y., Li, S., Li, S., Yang, X.J., Qin, Y., Liu, C.M., Zhang, Y.C., 2017. Screening and isolating potential α -glucosidase inhibitors from Rhizoma Coptidis by ultrafiltration LC-PDA-ESI/MS combined with high-speed countercurrent chromatography and reverse-phase medium-pressure liquid chromatography. Med. Chem. Res. 26, 3384-3394. https://doi.org/10.1007/s00044-017-2031-6.
- Tran, Q.T.N., Fred Wong, W.S., Chai, C.L.L., 2019. The identification of naturally occurring labdane diterpenoid calcaratarin D as a potential anti-inflammatory agent. Eur. J. Med. Chem. 174, 33-44. https://doi.org/10.1016/j.ejmech.2019.04.023.
- Wang, L.Y., Qiu, B.L., Xia, H., Xia, G.Y., Xiao, B.B., Zhang, J.F., Zhong, W.C., Lin, S., 2020. Yanhusanines A F, Isoquinoline-derived alkaloid enantiomers from Corydalis yanhusuo and their biological activity. J. Nat. Prod. 83, 489. https://doi.org/ 10.1021/acs.jnatprod.9b01155.
- Wang, Y.J., Wang, D.D., Zhang, J.H., Liu, D., Wang, Z.H., Meng, D.L., 2018. Isoquinolines from Corydalis tomentella from Tibet, China, possess hepatoprotective activities.
- Wu, L., Wang, G.C., Shen, T., Qiang, Q., Xue, Q., Chen, M., Zhang, J.M., Luo, Y.Y., Hong, Y.M., Si, C.L., Hu, W.C., 2018. Chemical constituents of leaves of Mahonia bealei. Chem. Nat. Compd. 54, 210-212. https://doi.org/10.1007/s10600-018-2302- 6.
- Xia, H., Liu, Y.T., Xia, G.Y., Liu, Y., Lin, S., Guo, L.J., 2021. Novel isoquinoline alkaloid Litcubanine A - a potential anti-inflammatory candidate. Front. Immunol. 12, 685556. https://doi.org/10.3389/fimmu.2021.685556.
- Xiao, B.B., Xia, G.Y., Wang, L.Y., Qiu, B.L., Xia, H., Zhong, W.C., Tian, G.H., Lin, S., 2020. (±)-Bicoryanhunine A, dimeric benzylisoquinoline alkaloid atropo-enantiomers from Corydalis yanhusuo. Tetrahedron Lett. 61, 151890. https://doi.org/10.1016/j. tetlet.2020.151890.
- Xie, C., Veitch, N.C., Houghton, P.J., Simmonds, M.S.J., 2004. Flavonoid glycosides and isoquinolinone alkaloids from Corydalis bungeana. Phytochemistry 65, 3041-3047. https://doi.org/10.1016/j.phytochem.2004.09.009.
- Zhang, J., He, S., Wang, J., Wang, C., Wu, J., Wang, W., Li, F., Li, S., Zhao, C., Li, F., 2020. A Review of the traditional uses, botany, phytochemistry, pharmacology, pharmacokinetics, and toxicology of Corydalis yanhusuo. Nat. Prod. Commun. 15, 1-19. https://doi.org/10.1177/1934578X20957752.
- Zhu, H., Wang, D., Wen, L., Yu, J.Q., Geng, Y.L., Zhao, H.Q., Zhao, R.X., Wang, X., 2016. Preparative separation of quaternary ammonium alkaloids from Caulis Mahoniae by conventional and pH-zone-refining counter-current chromatography. RSC Adv. 6, 83343. https://doi.org/10.1039/C6RA14056D.