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Published June 30, 2022 | Version v1
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Guided isolation of daphnane-type diterpenes from Daphne genkwa by molecular network strategies

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  • 1. * & Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Engineering Research Center of Natural

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Mi, Si-Hui, Zhao, Peng, Li, Qian, Zhang, Hao, Guo, Rui, Liu, Yu-Yang, Lin, Bin, Yao, Guo-Dong, Song, Shao-Jiang, Huang, Xiao-Xiao (2022): Guided isolation of daphnane-type diterpenes from Daphne genkwa by molecular network strategies. Phytochemistry (113144) 198: 1-8, DOI: 10.1016/j.phytochem.2022.113144, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113144

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urn:lsid:plazi.org:pub:FFF1FFB9FB17FFAF8A71FFD0FFA3DC6E

Cites
Publication: 10.1039/C9NP00006B (DOI)
Publication: 10.1016/j.ejmech.2020.112362 (DOI)
Publication: 10.1016/j.bmcl.2013.03.096 (DOI)
Publication: 10.1002/chir.22138 (DOI)
Publication: 10.1016/j.fitote.2020.104540 (DOI)
Publication: 10.1039/D0QO01475C (DOI)
Publication: 10.1016/j.chmed.2020.09.006 (DOI)
Publication: 10.1002/hlca.200900359 (DOI)
Publication: 10.1016/j.bmcl.2013.03.025 (DOI)
Publication: 10.1002/chin.201524220 (DOI)
Publication: 10.1016/j.bioorg.2020.104132 (DOI)
Publication: 10.1021/acs.jnatprod.8b00916 (DOI)
Publication: 10.1021/acs.jnatprod.0c00540 (DOI)
Publication: 10.1021/acs.jnatprod.0c00003 (DOI)
Publication: 10.1021/acs.jnatprod.0c00977 (DOI)
Publication: 10.1038/nbt.3597 (DOI)
Publication: 10.1007/s11418-018-1202-1 (DOI)
Publication: 10.1038/s41416-020-01085-z (DOI)
Publication: 10.1016/j.cbi.2018.04.014 (DOI)
Publication: 10.1002/hlca.200800419 (DOI)
Publication: 10.1016/j.bmc.2004.10.054 (DOI)
Publication: 10.1016/j.bmc.2006.01.055 (DOI)
Publication: 10.1021/acs.jnatprod.9b00993 (DOI)
Publication: 10.1021/acs.joc.1c01880 (DOI)
Has part
Figure: 10.5281/zenodo.8236020 (DOI)
Figure: 10.5281/zenodo.8236022 (DOI)
Figure: 10.5281/zenodo.8236024 (DOI)
Figure: 10.5281/zenodo.8236026 (DOI)
Figure: 10.5281/zenodo.8236028 (DOI)
Figure: 10.5281/zenodo.8236030 (DOI)
Figure: 10.5281/zenodo.8236032 (DOI)

References

  • Alexander, E.F., Laurent, E., Erwan, P., Pierre, C., Mehdi, A.B., 2019. Natural products targeting strategies involving molecular networking: different manners, one goal. Nat. Prod. Rep. 36, 960-980. https://doi.org/10.1039/C9NP00006B.
  • Bai, M., Chen, J.J., Xu, W., Dong, S.H., Liu, Q.B., Lin, B., Huang, X.X., Yao, G.D., Song, S. J., 2020. Elephantopinolide A-P, germacrane-type sesquiterpene lactones from Elephantopus scaber induce apoptosis, autophagy and G2/M phase arrest in hepatocellular carcinoma cells. Eur. J. Med. Chem. 198, 112362. https://doi.org/ 10.1016/j.ejmech.2020.112362.
  • Bang, K.K., Yun, C.Y., Lee, C., Jin, Q.H., Lee, J.W., Jung, S.H., Lee, D., Lee, M.K., Hong, J. T., Kim, Y., Hwang, B.Y., 2013. Melanogenesis inhibitory daphnane diterpenoids from the flower buds of Daphne genkwa. Bioorg. Med. Chem. Lett 23, 3334-3337. https://doi.org/10.1016/j.bmcl.2013.03.096.
  • Bruhn, T., Schaumloffel ¨, A., Hemberger, Y., Bringmann, G., 2013. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25, 243-249. https://doi.org/10.1002/chir.22138.
  • 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 Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, 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., 2013. Gaussian 09, Revision D.01. Gaussian, Inc., Wallingford, CT.
  • Giorgi, M., Nino, T., Vakhtang, M., 2020. The genus Daphne: a review of its traditional uses, phytochemistry and pharmacology. Fitoterapia 143, 104540. https://doi.org/ 10.1016/j.fitote.2020.104540.
  • Guo, R., Zhao, P., Yu, X.Q., Yao, G.D., Lin, B., Huang, X.X., Song, S.J., 2021. (±)-Pinnatifidaones A-D, four pairs of highly modified neolignan enantiomers with a rare spirocyclohexenone skeleton from Crataegus pinnatifida. Org. Chem. Front. 8, 953-960. https://doi.org/10.1039/D0QO01475C.
  • Hou, Z.L., Yao, G.D., Song, S.J., 2021. Daphne-type diterpenes from genus Daphne and their anti-tumor activity. Chin. Herb. Med. 13, 145-156. https://doi.org/10.1016/j. chmed.2020.09.006.
  • Li, L.Z., Gao, P.Y., Peng, Y., Wang, L.H., Yang, J.Y., Wu, C.F., Zhang, Y., Song, S.J., 2010. Daphnane-type diterpenoids from the flower buds of Daphne genkwa. Helv. Chim. Acta 93, 1172-1179. https://doi.org/10.1002/hlca.200900359.
  • Li, F.F., Sun, Q., Hong, L.L., Li, L.Z., Wu, Y.Y., Xia, M.Y., Takshi, I., Peng, Y., Song, S.J., 2013. Daphnane-type diterpenes with inhibitory activities against human cancer cell lines from Daphne genkwa. Bioorg. Med. Chem. Lett 23, 2500-2504. https://doi.org/ 10.1016/j.bmcl.2013.03.025.
  • Li, L.Z., Song, S.J., Gao, P.Y., Li, F.F., Wang, L.H., Liu, Q.B., Huang, X.X., Li, Dan-Qi, Sun, Yu, 2015. Neogenkwanines A-H: daphnane-type diterpenes containing 4,7 or 4,6-ether groups from the flower bud of Daphne genkwa. RSC Adv. 5, 4143-4152. https://doi.org/10.1002/chin.201524220.
  • Manon, T., Anne-C´ecile, L.L., Val´erie, J., Denis, J., J´erˆome, G., Val´erie, C., Elise, C., May, Y., Corinne, R., Nathalie, V., Kember, M., Billy, J.C., Claire, R.S., Nicolas, F., 2020. Daphnanes diterpenes from the latex of Hura crepitans L. and activity against human colorectal cancer cells Caco-2. Bioorg. Chem. 103, 104132. https://doi.org/ 10.1016/j.bioorg.2020.104132.
  • Melissa, N.E., Nothias, L.F., Silva, R.R.D., Retailleau, P., Zhang, Z., Leyssen, P., Roussi, F., Touboul, D., Paolini, J., Dorrestein, P.C., Litaudon, M., 2019. Investigation of premyrsinane and myrsinane Esters in Euphorbia cupanii and Euphobia pithyusa with MS2LDA and combinatorial molecular network annotation propagation. J. Nat. Prod. 82, 1459-1470. https://doi.org/10.1021/acs.jnatprod.8b00916.
  • Otsuki, K., Li, W., Miura, K., Asada, Y., Huang, L., Chen, C.H., Lee, K.H., Kazuo, K., 2020. Isolation, structural elucidation, and anti-HIV activity of daphnane diterpenoids from Daphne odora. J. Nat. Prod. 83, 3270-3277. https://doi.org/10.1021/acs. jnatprod.0c00540.
  • Pan, R.R., Zhang, C.Y., Li, Y., Zhang, B.B., Zhao, L., Ye, Y., Song, Y.N., Zhang, M., Tie, H. Y., Zhang, H., Zhu, J.Y., 2020. Daphnane diterpenoids from Daphne genkwa inhibit PI3K/Akt/mTOR signaling and induce cell cycle arrest and apoptosis in human colon cancer cells. J. Nat. Prod. 83, 1238-1248. https://doi.org/10.1021/acs. jnatprod.0c00003.
  • Pham, H.T., Lee, K.H., Jeong, E., Woo, S., Yu, J., Kim, W.Y., Lim, Y.W., Kim, K.H., Kang, K.B., 2021. Species prioritization based on spectral dissimilarity: a case study of polyporoid fungal species. J. Nat. Prod. 84, 298-309. https://doi.org/10.1021/ acs.jnatprod.0c00977.
  • Wang, M.X., et al., 2016. Sharing and community curation of mass spectrometry data with global natural products social molecular networking. Nat. Biotechnol. 34, 828-837. https://doi.org/10.1038/nbt.3597.
  • Wang, L., Lan, X.Y., Ji, J., Zhang, C.F., Li, F., Wang, C.Z., Yuan, C.S., 2018. Antiinflammatory and anti-angiogenic activities in vitro of eight diterpenes from Daphne genkwa based on hierarchical cluster and principal component analysis. J. Nat. Med. 72, 675-685. https://doi.org/10.1007/s11418-018-1202-1.
  • Wu, J., Guo, L., Qiu, X.R., Ren, Y., Li, F.F., Cui, W., Song, S.J., 2020. Genkwadaphnin inhibits growth and invasion in hepatocellular carcinoma by blocking DHCR24- mediated cholesterol biosynthesis and lipid rafts formation. Br. J. Cancer 123, 1673-1685. https://doi.org/10.1038/s41416-020-01085-z.
  • Yao, G.D., Sun, Q., Song, X.Y., Huang, X.X., Song, S.J., 2018. Flavan enantiomers from Daphne giraldii selectively induce apoptotic cell death in p53-null hepatocarcinoma cells in vitro. Chem. Biol. Interact. 289, 1-8. https://doi.org/10.1016/j. cbi.2018.04.014.
  • Zeng, Y.M., Zuo, W.J., Sun, M.G., Meng, H., Wang, Q.H., Wang, J.H., Li, X., 2009. Three new daphne diterpenes from the buds of Daphne genkwa Sieb. et Zucc. processed by rice vinegar. Helv. Chim. Acta 92, 1273-1281. https://doi.org/10.1002/ hlca.200800419.
  • Zhan, Z.J., Fan, C.Q., Ding, J., Yue, J.M., 2005. Novel diterpenoids with potent inhibitory activity against endothelium cell HMEC and cytotoxic activities from a well-known TCM plant Daphne genkwa. Bioorg. Med. Chem. 13, 645-655. https://doi.org/ 10.1016/j.bmc.2004.10.054.
  • Zhang, S.X., Li, X.N., Zhang, F.H., Yang, P.W., Gao, X.J., Song, Q.L., 2006. Preparation of yuanhuacine and relative daphne diterpene esters from Daphne genkwa and structure-activity relationship of potent inhibitory activity against DNA topoisomerase I. Bioorg. Med. Chem. 14, 3888-3895. https://doi.org/10.1016/j. bmc.2006.01.055.
  • Zhao, H.D., Lu, Y., Yan, M., Chen, C.H., Susan, L.M.N., Lee, K.H., Chen, D.F., 2020. Rapid recognition and targeted isolation of anti-HIV daphnane diterpenes from Daphne genkwa guided by UPLC-MSn . J. Nat. Prod. 83, 134-141. https://doi.org/10.1021/ acs.jnatprod.9b00993.
  • Zhao, P., Li, Z.Y., Qin, S.Y., Xin, B.S., Liu, Y.Y., Lin, B., Yao, G.D., Huang, X.X., Song, S.J., 2021. Three unusual sesquiterpenes with distinctive ring skeletons from Daphne penicillata uncovered by molecular networking strategies. J. Org. Chem. 86, 15298-15306. https://doi.org/10.1021/acs.joc.1c01880.