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Published July 31, 2021 | Version v1
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Polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum pseudohenryi

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Sun, Haoran, Wang, Jiajia, Zhen, Bo, Wang, Xue, Suo, Xinyue, Lin, Mingbao, Jiang, Jiandong, Ji, Tengfei (2021): Polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum pseudohenryi. Phytochemistry (112761) 187: 1-8, DOI: 10.1016/j.phytochem.2021.112761, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112761

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urn:lsid:plazi.org:pub:FFF4FF91D534E93C1637FF928C75FFC0

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Figure: 10.5281/zenodo.8259006 (DOI)
Figure: 10.5281/zenodo.8259008 (DOI)
Figure: 10.5281/zenodo.8259010 (DOI)
Figure: 10.5281/zenodo.8259012 (DOI)
Figure: 10.5281/zenodo.8259014 (DOI)
Figure: 10.5281/zenodo.8259016 (DOI)
Figure: 10.5281/zenodo.8259018 (DOI)
Figure: 10.5281/zenodo.8259020 (DOI)
Figure: 10.5281/zenodo.8259022 (DOI)

References

  • Bystrov, N.S., Chernov, B.K., Dobrynin, V.N., et al., 1975. The structure of hyperforin. Tetrahedron Lett. 16, 2791-2794.
  • Chen, T.L.F., 2012. Multiwfn: a multifunctional wavefunction analyzer. J. Comput. Chem. 33, 580-592.
  • Chen, X.Q., Li, Y., Cheng, X., et al., 2010. Polycyclic polyprenylated acylphloroglucinols and chromone O-glucosides from Hypericum henryi subsp. uraloides. Chem. Biodivers. 7, 196-204.
  • Ciochina, R., Grossman, R.B., 2006. Polycyclic polyprenylated acylphloroglucinols. Chem. Rev. 106, 3963-3986.
  • Friedland, K., Harteneck, C., 2015. Hyperforin: to Be or not to Be an activator of TRPC (6). Rev. Physiol. Biochem. Pharmacol. 169, 1-24.
  • Gao, W., Hou, W.-Z., Zhao, J., et al., 2016a. Polycyclic polyprenylated acylphloroglucinol congeners from Hypericum scabrum. J. Nat. Prod. 79, 1538-1547.
  • Gao, W., Hu, J.W., Xu, F., et al., 2016b. Polyisoprenylated benzoylphloroglucinol derivatives from Hypericum scabrum. Fitoterapia 115, 128-134.
  • Griffith, T., Varela-Nallar, L., Dinamarca, M., et al., 2010. Neurobiological effects of hyperforin and its potential in alzheimers disease therapy. Curr. Med. Chem. 17, 391-406.
  • Grossman, R.B., Jacobs, H., 2000. On the structures of plukenetiones B, D, and E and their relationships to other polycyclic polyprenylated acylphloroglucinols. Tetrahedron Lett. 41, 5165-5169.
  • Guo, N., Chen, X.-Q., Zhao, Q.-S., 2008. A new polyisoprenylated benzoylphloroglucinol derivative from Hypericum henryi subsp. uraloides (Guttiferae). Acta Bot. Yunnanica 30, 515-518.
  • Guo, Y., Zhang, N., Sun, W., et al., 2018. Bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum perforatum. Org. Biomol. Chem. 16, 8130-8143.
  • Gupta, R.K., Moller, H.J., 2003. St. John' s Wort. An option for the primary care treatment of depressive patients? Eur. Arch. Psychiatr. Clin. Neurosci. 253, 140-148.
  • Henry, G.E., Jacobs, H., Carrington, C.M.S., et al., 1999. Prenylated benzophenone derivatives from Caribbean Clusia species (Guttiferae). Plukenetiones B-G and xerophenone A. Tetrahedron 55, 1581-1596.
  • Hu, J., Gao, W., Xu, F., et al., 2017. Polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum scabrum. Bioorg. Med. Chem. Lett 27, 4932-4936.
  • Hu, Y.L., Hu, K., Kong, L.M., et al., 2019. Norascyronones A and B, 2,3,4-nor -Polycyclic Polyprenylated Acylphloroglucinols from Hypericum ascyron. Org. Lett. 21, 1007-1010.
  • Hu, J.-W., Shi, M.-J., Wang, J.-J., et al., 2018. Methylated polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum ascyron. J. Nat. Prod. 81, 2348-2356.
  • Hu, L.-H., Sim, K.-Y., 2000. Sampsoniones A-M, a unique family of caged polyprenylated benzoylphloroglucinol derivatives, from Hypericum sampsonii. Tetrahedron 56, 1379-1386.
  • Liao, Y., Yang, S.-Y., Li, X.-N., et al., 2016. Polyprenylated acylphloroglucinols from the fruits of Hypericum henryi. Sci. China Chem. 59, 1216-1223.
  • Lodewyk, M.W., Tantillo, D.J., 2011. Prediction of the structure of nobilisitine a using computed NMR chemical shifts. J. Nat. Prod. 74, 1339-1343.
  • Lu, T., 2020. Molclus Program, Version 1.9.6.
  • Lu, T., Chen, Q., 2020. Shermo: A General Code for Calculating Molecular Thermodynamic Properties. ChemRxiv.
  • Mitsopoulou, K.P., Vidali, V.P., Koliopoulos, G., et al., 2014. Hyperforin and deoxycohumulone as a larvicidal agent against Culex pipiens (Diptera: Culicidae). Chemosphere 100, 124-129.
  • Mohammed Sur, T., Akbaba, E., Hassan, S.A., et al., 2019. Neuropharmacological profile of Hypericum scabrum L. essential oil in rats. J. Essent. Oil Res. 1-9.
  • Neese, F., 2017. Software update: the ORCA program system, version 4.0. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 8, e1327.
  • Novelli, M., Menegazzi, M., Beffy, P., et al., 2016. St. John' s wort extract and hyperforin inhibit multiple phosphorylation steps of cytokine signaling and prevent inflammatory and apoptotic gene induction in pancreatic β cells. Int. J. Biochem. Cell Biol. 81, 92-104.
  • Saadat, N., Gupta, S.V., 2012. Potential role of garcinol as an anticancer agent. J. Oncol. 2012, 647206.
  • Schiavone, B.I., Rosato, A., Marilena, M., et al., 2013. Biological evaluation of hyperforin and its hydrogenated analogue on bacterial growth and biofilm production. J. Nat. Prod. 76, 1819-1823.
  • Smith, S.G., Goodman, J.M., 2010. Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 probability. J. Am. Chem. Soc. 132, 12946-12959.
  • Sosa, S., Pace, R., Bornancin, A., et al., 2007. Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L. J. Pharm. Pharmacol. 59, 703-709.
  • Stewart, J.J.P., 2016. MOPAC2016. Stewart Computational Chemistry, Colorado Springs, CO, USA.
  • Teixeira, J.S.A.R., Cruz, F.G., 2005. Polyisoprenylated benzophenone derivatives from Clusia obdeltifolia. Tetrahedron Lett. 46, 2813-2816.
  • Verotta, L., Appendino, G., Bombardelli, E., et al., 2007. In vitro antimalarial activity of hyperforin, a prenylated acylphloroglucinol. A structure-activity study. Bioorg. Med. Chem. Lett 17, 1544-1548.
  • Wang, X., Shi, M., Wang, J., et al., 2020. Hyperacmosins E-G, three new homoadamantane-type polyprenylated acylphloroglucinols from Hypericum acmosepalum. Fitoterapia 142, 104535.
  • Yang, X.-W., Grossman, R.B., Xu, G., 2018. Research Progress of Polycyclic Polyprenylated Acylphloroglucinols, vol. 118. Chem. Rev., Washington, DC, U. S., pp. 3508-3558
  • Yang, X.-W., Wang, H., Ma, W.-G., et al., 2017. homo-adamantane type polyprenylated acylphloroglucinols from Hypericum pseudohenryi. Tetrahedron 73, 566-570.
  • Zhen, B., Hu, J.W., Wang, J.J., et al., 2019. Hyperascyrins L - N, rare methylated polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum ascyron. J. Asian Nat. Prod. Res. 21, 409-418.
  • Zhou, Z.-B., Li, Z.-R., Wang, X.-B., et al., 2016. Polycyclic polyprenylated derivatives from Hypericum uralum: neuroprotective effects and antidepressant-like activity of Uralodin A. J. Nat. Prod. 79, 1231-1240.