Published April 30, 2023 | Version v1
Journal article Restricted

Undescribed phloroglucinol derivatives with antiviral activities from Dryopteris atrata (Wall. Ex Kunze) Ching

  • 1. , Jin-lin Chen & , Wei-bin Xu & , Yi-ping Xia & , Hao-yue Zhu & , Jing-hao Wang & , Guo-cai Wang & *** , Yu-bo Zhang & Institute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, & , Jin-lin Chen & , Wei-bin Xu

Description

Zhang, Ji-hui, Chen, Jin-lin, Xu, Wei-bin, Xia, Yi-ping, Zhu, Hao-yue, Wang, Jing-hao, Li, Yao-lan, Wang, Guo-cai, Zhang, Yu-bo, Chen, Neng-hua (2023): Undescribed phloroglucinol derivatives with antiviral activities from Dryopteris atrata (Wall. Ex Kunze) Ching. Phytochemistry (113585) 208: 113585, DOI: 10.1016/j.phytochem.2023.113585, URL: http://dx.doi.org/10.1016/j.phytochem.2023.113585

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:812CFF8CFFCAFFE7DD3EE226FFC9FFFD

References

  • Boland, D.J., Brophy, J.J., Fookes, C.J., 1992. Jensenone, a ketone from Eucalyptus jen. Phytochemistry 31, 2178-2179. https://doi.org/10.1016/0031-9422(92)80396-V.
  • Boti, J.B., Koukoua, G., N' Guessan, T.Y., Muselli, A., Bernardini, A.F., Casanova, J., 2005. Composition of the leaf, stem bark and root bark oils of Isolona cooperi investigated by GC (retention index), GC-MS and 13 C-NMR spectroscopy.Phytochem. Anal. 16, 357-363. https://doi.org/10.1002/pca.857.
  • Bruhn, T., Schaumloffel ¨, A., Hemberger, Y., Bringmann, G., 2012. SpecDis Version 1.60. University of Wuerzburg, Germany, 2012.
  • Cao, J.Q., Tian, H.Y., Li, M.M., Zhang, W., Wang, Y., Wang, L., Ye, W.C., 2018. Rearranged phloroglucinol-monoterpenoid adducts from Callistemon rigidus. J. Nat. Prod. 81, 57-62. https://doi.org/10.1021/acs.jnatprod.7b00606.
  • Chen, N.H., Wu, Z.N., Li, W., Li, Y.Y., Luo, D., Chen, L.F., Zhang, X.L., Zhang, Y.B., Wang, G.C., Li, Y.L., 2020. Acylphloroglucinols-based meroterpenoid enantiomers with antiviral activities from Dryopteris crassirhizoma. Ind. Crop. Prod. 150, 112415 https://doi.org/10.1016/j.indcrop.2020.112415.
  • Chen, N.H., Zhang, Y.B., Huang, X.J., Jiang, L., Jiang, S.Q., Li, G.Q., Li, Y.L., Wang, G.C., 2016. Drychampones A-C: three meroterpenoids from Dryopteris championii. J. Org. Chem. 81, 9443-9448. https://doi.org/10.1021/acs.joc.6b01720.
  • Dewick, P.M., 2009. Medicinal Natural Products: A Biosynthetic Approach, 3rd et. John Wiley & Sons, td., New York.
  • Editorial Committee of Flora of China, 2000. Flora of China. Science Press, Beijing, China, p. 123.
  • Editorial Committee of Zhonghua Bencao, 1999. Zhonghua Bencao. Shanghai Science and Technology Press, Shanghai, China, p. 198.
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendel, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J., 2009. Gaussian 09, Revision B.01. Gaussian, Inc., Wallingford, CT.
  • Hai, P., Rao, K.P., Jiang, N., Liu, D., Wang, R.R., Gao, Y., Liu, X.C., Deng, S.H., Zhou, Y., Chen, X.Q., Li, X.N., Li, R.T., 2021. Structure elucidation, biogenesis, and bioactivities of acylphloroglucinol-derived meroterpenoid enantiomers from Dryopteris crassirhizoma. Bioorg. Chem. 119, 105567 https://doi.org/10.1016/j. bioorg.2021.105567.
  • Han, X., Li, Z., Li, C.Y., Jia, W.N., Wang, H.T., Wang, C.H., 2015. Phytochemical constituents and biological activities of plants from the genus Dryopteris. Chem. Biodivers. 12, 1131-1162. https://doi.org/10.1002/cbdv.201400157.
  • Hirota, H., Tomono, Y., Fusetani, N., 1996. Terpenoids with antifouling activity against barnacle larvae from the marine sponge Acanthella cavernosa. Tetrahedron Lett. 52, 2359-2368. https://doi.org/10.1016/0040-4020(95)01079-3.
  • Hou, B., Zhang, Y.M., Liao, H.Y., Fu, L.F., Li, D.D., Zhao, X., Qi, J.X., Yang, W., Xiao, G.F., Yang, L., Zuo, Z.Y., Wang, L., Zhang, X.L., Bai, F., Yang, L., Gao, G.F., Song, H., Hu, J. M., Shang, W.J., Zhou, J., 2022. Target-based virtual screening and LC/MS-guided isolation procedure for identifying phloroglucinol-terpenoid Inhibitors of SARS-CoV-2. J. Nat. Prod. 85, 327-336. https://doi.org/10.1021/acs.jnatprod.1c00805.
  • Hu, L.Z., Zhang, Y., Zhu, H.C., Liu, J.J., Li, H., Li, X.N., Sun, W.G., Zeng, J.F., Xue, Y.B., Zhang, Y.H., 2016. Filicinic acid based meroterpenoids with anti-epstein-barr virus activities from Hypericum japonicum. Org. Lett. 18, 2272-2275. https://doi.org/ 10.1021/acs.orglett.6b00906.
  • Lee, H.B., Kim, J.C., Lee, S.M., 2009. Antibacterial activity of two phloroglucinols, flavaspidic acids AB and PB, from Dryopteris crassirhizoma. Arch Pharm. Res. (Seoul) 32, 655-659. https://doi.org/10.1007/s12272-009-1502-9.
  • Lee, S.M., Na, M.K., An, R. Bo, Min, B.S., Lee, H.K., 2003. Antioxidant activity of two phloroglucinol derivatives from Dryopteris crassirhizoma. Biol. Pharm. Bull. 26, 1354-1356. https://doi.org/10.1248/bpb.26.1354.
  • Magalhaes, L.G., Kapadia, G.J., Da Silva Tonuci, L.R., Caixeta, S.C., Parreira, N.A., Rodrigues, V., Da Silva Filho, A.A., 2010. In vitro schistosomicidal effects of some phloroglucinol derivatives from Dryopteris species against Schistosoma mansoni adult worms. Parasitol. Res. 106, 395-401. https://doi.org/10.1007/s00436-009-1674-8.
  • Mustafa, K.A., Kjaergaard, H.G., Perry, N.B., Weavers, R.T., 2003. Hydrogen-bonded rotamers of 2',4',6'-trihydroxy-3'-formyldihydrochalcone, an intermediate in the synthesis of a dihydrochalcone from Leptospermum recurvum. Tetrahedron 59, 6113-6120.
  • Phong, N.V., Oanh, V.T., Yang, S.Y., Choi, J.S., Min, B.S., Kim, J.A., 2021. PTP1B inhibition studies of biological active phloroglucinols from the rhizomes of Dryopteris crassirhizoma: kinetic properties and molecular docking simulation. Int. J. Biol. Macromol. 188, 719-728.
  • Qin, X.J., Jin, L.Y., Yu, Q., Liu, H., Khan, A., Yan, H., Hao, X.J., An, L.K., Liu, H.Y., 2018. Eucalypglobulusals A-J, formyl-phloroglucinol-terpene meroterpenoids from Eucalyptus globulus fruits. J. Nat. Prod. 81, 2638-2646. https://doi.org/10.1021/acs. jnatprod.8b00430.
  • Ryu, B., Cho, H.M., Zhang, M., Lee, B.W., Doan, T.P., Park, E.J., Lee, H.J., Oh, W.K., 2021. Meroterpenoids from the leaves of Psidium guajava (guava) cultivated in Korea using MS/MS-based molecular networking. Phytochemistry 186.
  • Socolsky, C., Dominguez, L., Asakawa, Y., Bardon, A., 2012. Unusual terpenylated acylphloroglucinols from Dryopteris wallichiana. Phytochemistry 80, 115-122.
  • Sun, Y., Gao, C., Luo, M., Wang, W., Gu, C.B., Zu, Y.G., Li, J., Efferth, T., Fu, Y.J., 2013. Aspidin PB, a phloroglucinol derivative, induces apoptosis in human hepatocarcinoma HepG2 cells by modulating PI3K/Akt/GSK3β pathway. Chem. Biol. Interact. 201, 1-8. https://doi.org/10.1016/j.cbi.2012.11.005.
  • Vidari, G., Che, Z.L., Garlaschelli, L., 1998. New nardosinane and aristolane sesquiterpenes from the fruiting bodies of Russula lepida. Tetrahedron Lett. 39, 6073-6076. https://doi.org/10.1016/S0040-4039(98)01251-9.
  • Yang, Q., Gao, L., Si, J.Y., Sun, Y.P., Liu, J.H., Cao, L., Feng, W.H., 2013. Inhibition of porcine reproductive and respiratory syndrome virus replication by flavaspidic acid AB. Antivir. Res. 97, 66-73. https://doi.org/10.1016/j.antiviral.2012.11.004.