Biodiversity Literature Repository

Submit to community
Liberated Data
Published October 31, 2021 | Version v1
Journal article Restricted

Unusual matrine-adenine hybrids isolated from Sophora davidii and their inhibitory effects on human cytomegalovirus

Creators

  • 1. , Shu-Wei Dong & , Dan-Dan Gao, Xin-Ye Du, Yan-Qing Xie, Xue-Shan Xia,

Description

Zhang, Zhi-Jun, Dong, Shu-Wei, Gao, Dan-Dan, Du, Xin-Ye, Xie, Yan-Qing, Xia, Xue-Shan, Li, Rong-Tao (2021): Unusual matrine-adenine hybrids isolated from Sophora davidii and their inhibitory effects on human cytomegalovirus. Phytochemistry (112842) 190: 112842, DOI: 10.1016/j.phytochem.2021.112842, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112842

Files

Restricted

The record is publicly accessible, but files are restricted to users with access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:FF8B6278FFEEFFC9FFF33C11FFB85114

Cites
Publication: 10.1016/j.jcv.2012.02.008 (DOI)
Publication: 10.1016/j.pid.2016.03.004 (DOI)
Publication: 10.1016/j.canlet.2013.09.004 (DOI)
Publication: 10.1007/BF03166189 (DOI)
Publication: 10.1002/med.20030 (DOI)
Publication: 10.2165/00003495-199141010-00009 (DOI)
Publication: 10.1021/acs.orglett.0c01593 (DOI)
Publication: 10.13375/j.cnki.wcjps.2010.06.017 (DOI)
Publication: 10.1007/s12250-019-00106-3 (DOI)
Publication: 10.1016/S1367-5931(97)80009-9 (DOI)
Publication: 10.1016/j.phytol.2020.01.007 (DOI)
Publication: 10.1007/s11427-013-4562-5 (DOI)
Publication: 10.1016/S0166-3542(97)00012-0 (DOI)
Publication: 10.3389/fphar.2018.00760 (DOI)
Publication: 10.1056/NEJMoa1404599 (DOI)
Publication: 10.1016/j.phytochem.2020.112373 (DOI)
Publication: 10.1002/cbdv.201900080 (DOI)
Publication: 10.1182/blood.v97.2.388 (DOI)
Publication: 10.1128/CMR.00009-10 (DOI)
Publication: 10.1016/j.molstruc.2009.09.040 (DOI)
Publication: 10.1186/s12887-017-0933-6 (DOI)
Publication: 10.1002/(SICI)1096-987X,19981115)19:14<1639::AIDJCC10>3.0.CO;2-B (DOI)
Publication: 10.1016/0040-4039(96)01078-7 (DOI)
Publication: 10.1021/acs.jmedchem.7b01395 (DOI)
Publication: 10.1016/j.foodchem.2010.12.048 (DOI)
Publication: 10.1016/S0031-9422(00)00016-9 (DOI)
Publication: 10.1038/1860 (DOI)
Publication: 10.1038/s41422-020-0305-x (DOI)
Publication: 10.1016/S0031-9422(98)00486-5 (DOI)
Publication: 10.1128/AAC.41.3.594 (DOI)
Has part
Dataset: http://table.plazi.org/id/DF64FB9EFFEFFFC8FCC13C87FA2E51D5 (URL)
Figure: 10.5281/zenodo.8160379 (DOI)
Figure: 10.5281/zenodo.8160381 (DOI)
Figure: 10.5281/zenodo.8164505 (DOI)
Figure: 10.5281/zenodo.8160383 (DOI)
Figure: 10.5281/zenodo.8160385 (DOI)
Figure: 10.5281/zenodo.8160387 (DOI)
Figure: 10.5281/zenodo.8160389 (DOI)
Dataset: http://table.plazi.org/id/DF64FB9EFFEDFFCAFCC13A26FA245775 (URL)

References

  • Agut, H., 2012. Emergence of cytomegalovirus resistance to foscarnet in a patient receiving foscarnet salvage therapy for multidrug-resistant HIV infection. J. Clin. Virol. 54, 194-196. https://doi.org/10.1016/j.jcv.2012.02.008.
  • Alam, M.M., Bayoumy, M., Ali, A., Alali, M., Al-Enezi, B., Abosoudah, I., 2016. Cytomegalovirus infection in children after bone marrow transplantation: risk factors, clinical aspects and outcomes. Pediatr. Infect. Dis. 8, 1-7. https://doi.org/ 10.1016/j.pid.2016.03.004.
  • Ariza-Heredia, E.J., Lior, N., Chemaly, R.F., 2014. Cytomegalovirus diseases after hematopoietic stem cell transplantation: a mini-review. Canc. Lett. 342, 1-8. https:// doi.org/10.1016/j.canlet.2013.09.004.
  • Bai, G.Y., Wang, D.Q., Ye, C.H., Liu, M.L., 2002. 1 H and 13C chemical shift assignments and stereochemistry of matrine and oxymatrine. Appl. Magn. Reson. 23, 113-121. https://doi.org/10.1007/BF03166189.
  • Borthwick, A.D., 2005. Design of translactam HCMV protease inhibitors as potent antivirals. Med. Res. Rev. 25, 427-452. https://doi.org/10.1002/med.20030.
  • Chrisp, P., Clissold, S.P., 1991. Foscarnet. Drugs 41, 104-129. https://doi.org/10.2165/ 00003495-199141010-00009.
  • Ding, W.Y., Yan, Y.M., Meng, X.H., Nafie, L.A., Xu, T., Dukor, R.K., Qin, H.B., Cheng, Y. X., 2020. Isolation, total Synthesis, and absolute configuration determination of renoprotective dimeric N -acetyldopamine-adenine hybrids from the Insect Aspongopus chinensis. Org. Lett. 22, 5726-5730. https://doi.org/10.1021/acs. orglett.0c01593.
  • Dong, L.H., Tai, Z.G., Yang, Y.B., Liu, C.S., Cai, L., Ding, Z.T., 2010. Chemical constituents of the flowers of Sophora viciifolia hance. West chin. J. Pharm. Sci. 25, 636-640. https://doi.org/10.13375/j.cnki.wcjps.2010.06.017.
  • Dong, S.W., Jiao, L.S., Yang, M., Duan, Y.L., Chen, Y.B., Zhao, F., Zhang, A.M., Liu, L., Luo, M.H., Xia, X.S., 2019. The susceptibility of primary dermis fibroblasts from the Chinese tree shrew to human cytomegalovirus infection. Virol. Sin. 34, 270-277. https://doi.org/10.1007/s12250-019-00106-3.
  • Flynn, D.L., Abood, N.A., Holwerda, B.C., 1997. Recent advances in antiviral research: identification of inhibitors of the herpesvirus proteases. Curr. Opin. Chem. Biol. 1, 190-196. https://doi.org/10.1016/S1367-5931(97)80009-9.
  • Gao, D.D., Zhang, Z.J., Li, H.M., Chen, X.Q., Liu, D., Li, R.T., 2020. Four new quinolizidine alkaloids from the flowers of Sophora viciifolia. Phytochem. Lett. 36, 91-94. https://doi.org/10.1016/j.phytol.2020.01.007.
  • Guo, L.P., Wang, S., Zhang, J., Yang, G., Zhao, M.X., Ma, W.F., Zhang, X.B., Li, X., Han, B. X., Chen, N.F., Huang, L.Q., 2013. Effects of ecological factors on secondary metabolites and inorganic elements of Scutellaria baicalensis and analysis of geoherblism. Sci. China Life Sci. 56, 1047-1056. https://doi.org/10.1007/s11427- 013-4562-5.
  • Holwerda, B.C., 1997. Herpesvirus proteases: targets for novel antiviral drugs. Antivir. Res. 35, 1-21. https://doi.org/10.1016/S0166-3542(97)00012-0.
  • Huang, Y., Hao, J., Tian, D., Wen, Y., Zhao, P., Chen, H., Lv, Y., Yang, X., 2018. Antidiabetic activity of a flavonoid-rich extract from Sophora davidii (Franch.) skeels in KK-Ay mice via activation of AMP-activated protein kinase. Front. Pharmacol. 9, 760. https://doi.org/10.3389/fphar.2018.00760.
  • Kimberlin, D.W., Jester, P.M., S´anchez, P.J., Ahmed, A., Arav-Boger, R., Michaels, M.G., Ashouri, N., Englund, J.A., Estrada, B., Jacobs, R.F., Romero, J.R., Sood, S.K., Whitworth, M.S., Abzug, M.J., Caserta, M.T., Fowler, S., Lujan-Zilbermann, J., Storch, G.A., DeBiasi, R.L., Han, J.Y., Palmer, A., Weiner, L.B., Bocchini, J.A., Dennehy, P.H., Finn, A., Griffiths, P.D., Luck, S., Gutierrez, K., Halasa, N., Homans, J., Shane, A.L., Sharland, M., Simonsen, K., Vanchiere, J.A., Woods, C.R., Sabo, D.L., Aban, I., Kuo, H., James, S.H., Prichard, M.N., Griffin, J., Giles, D., Acosta, E.P., Whitley, R.J., 2015. Valganciclovir for symptomatic congenital cytomegalovirus disease. N. Engl. J. Med. 372, 933-943. https://doi.org/10.1056/ NEJMoa1404599.
  • Li, J.C., Dai, W.F., Liu, D., Jiang, M.Y., Zhang, Z.J., Chen, X.Q., Chen, C.H., Li, R.T., Li, H. M., 2020. Bioactive ent-isopimarane diterpenoids from Euphorbia neriifolia. Phytochemistry 175, 112373. https://doi.org/10.1016/j.phytochem.2020.112373.
  • Lin, B.B., Liu, X., Wu, S.Q., Zheng, H.X., Huo, K.K., Qi, S.S., Chen, C., 2019. Phytochemicals content, antioxidant and antibacterial activities of Sophora viciifolia. Chem. Biodivers. 16, e1900080 https://doi.org/10.1002/cbdv.201900080.
  • Ljungman, P., Deliliers, G.L., Platzbecker, U., Matthes-Martin, S., Bacigalupo, A., Einsele, H., Ullmann, J., Musso, M., Trenschel, R., Ribaud, P., Bornh¨auser, M., Cesaro, S., Crooks, B., Dekker, A., Gratecos, N., Klingebiel, T., Tagliaferri, E., Ullmann, A.J., Wacker, P., Cordonnier, C., 2001. Cidofovir for cytomegalovirus infection and disease in allogeneic stem cell transplant recipients. The infectious diseases working party of the European group for blood and marrow transplantation. Blood 97, 388-392. https://doi.org/10.1182/blood.v97.2.388.
  • Lurain, N.S., Chou, S., 2010. Antiviral drug resistance of human cytomegalovirus. Clin. Microbiol. Rev. 23, 689-712. https://doi.org/10.1128/CMR.00009-10.
  • Mohamed, T.A., Shabaan, I.A., Zoghaib, W.M., Husband, J., Farag, R.S., Alajhaz, A.E.N. M.A., 2009. Tautomerism, normal coordinate analysis, vibrational assignments, calculated IR, Raman and NMR spectra of adenine. J. Mol. Struct. 938, 263-276. https://doi.org/10.1016/j.molstruc.2009.09.040.
  • Morillo-Gutierrez, B., Waugh, S., Pickering, A., Flood, T., Emonts, M., 2017. Emerging (val)ganciclovir resistance during treatment of congenital CMV infection: a case report and review of the literature. BMC Pediatr. 17, 181. https://doi.org/10.1186/ s12887-017-0933-6.
  • Morris, G.M., Goodsell, D.S., Halliday, R.S., Huey, R., Hart, W.E., Belew, R.K., Olson, A. J., 1998. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 19, 1639-1662. https://doi.org/10.1002/(SICI)1096-987X, 19981115)19:14<1639::AIDJCC10>3.0.CO;2-B.
  • Ohyama, M., Ichise, M., Tanaka, T., Iinuma, M., Burandt, C.L., 1996. Davidiol D, first naturally occurring resveratrol pentamer isolated from Sophora davidii. Tetrahedron Lett. 37, 5155-5158. https://doi.org/10.1016/0040-4039(96)01078-7.
  • Shao, L.D., Su, J., Ye, B., Liu, J.X., Zuo, Z.L., Li, Y., Wang, Y.Y., Xia, C., Zhao, Q.S., 2017. Design, synthesis, and biological activities of vibsanin B derivatives: a new class of HSP90 C-terminal inhibitors. J. Med. Chem. 60, 9053-9066. https://doi.org/ 10.1021/acs.jmedchem.7b01395.
  • Tai, Z., Cai, L., Dai, L., Dong, L., Wang, M., Yang, Y., Cao, Q., Ding, Z., 2011. Antioxidant activity and chemical constituents of edible flower of Sophora viciifolia. Food Chem. 126, 1648-1654. https://doi.org/10.1016/j.foodchem.2010.12.048.
  • Tanaka, T., Ito, T., Iinuma, M., Ohyama, M., Ichise, M., Tateishi, Y., 2000. Stilbene oligomers in roots of Sophora davidii. Phytochemistry 53, 1009-1014. https://doi. org/10.1016/S0031-9422(00)00016-9.
  • Tong, L., Qian, C., Massariol, M.J., D´eziel, R., Yoakim, C., Lagac´e, L., 1998. Conserved mode of peptidomimetic inhibition and substrate recognition of human cytomegalovirus protease. Nat. Struct. Mol. Biol. 5, 819-826. https://doi.org/ 10.1038/1860.
  • Xia, S., Liu, M., Wang, C., Xu, W., Lan, Q., Feng, S., Qi, F., Bao, L., Du, L., Liu, S., Qin, C., Sun, F., Shi, Z., Zhu, Y., Jiang, S., Lu, L., 2020. Inhibition of SARS-CoV-2 (previously 2019-nCoV) infection by a highly potent pan-coronavirus fusion inhibitor targeting its spike protein that harbors a high capacity to mediate membrane fusion. Cell Res. 30, 343-355. https://doi.org/10.1038/s41422-020-0305-x.
  • Xiao, P., Kubo, H., Komiya, H., Higashiyama, K., Yan, Y.N., Li, J.S., Ohmiya, S., 1999. Lupin alkaloids from seeds of Sophora viciifolia. Phytochemistry 50, 189-193. https://doi.org/10.1016/S0031-9422(98)00486-5.
  • Xiong, X., Smith, J.L., Chen, M.S., 1997. Effect of incorporation of cidofovir into DNA by human cytomegalovirus DNA polymerase on DNA elongation. Antimicrob. Agents Chemother. 41, 594-599. https://doi.org/10.1128/AAC.41.3.594.