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Published August 31, 2021 | Version v1
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Ingenane and jatrophane-type diterpenoids from Euphorbia kansui with multidrug resistance reversal activity

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Wang, Siyi, Li, Jianchun, Liu, Dan, Yang, Tao, Chen, Xuanqin, Li, Rongtao (2021): Ingenane and jatrophane-type diterpenoids from Euphorbia kansui with multidrug resistance reversal activity. Phytochemistry (112775) 188: 1-8, DOI: 10.1016/j.phytochem.2021.112775, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112775

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urn:lsid:plazi.org:pub:C927FFDAFFB8FFE6936A9268A77EFFA7

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Publication: 10.2174/15680096113139990076 (DOI)
Publication: 10.1371/journal.pone.0168027 (DOI)
Publication: 10.1002/cbdv.201700560 (DOI)
Publication: 10.1055/s-2005-873196 (DOI)
Publication: 10.1021/acs.jnatprod.6b00644 (DOI)
Publication: 10.1515/znb-1984-0525 (DOI)
Publication: 10.1038/nrc706 (DOI)
Publication: 10.1016/j.bmcl.2013.11.073 (DOI)
Publication: 10.1021/acs.jnatprod.8b00507 (DOI)
Publication: 10.1021/np030036f (DOI)
Publication: 10.1016/S0031-9422(99)00088-6 (DOI)
Publication: 10.1021/acs.jnatprod.9b00088 (DOI)
Publication: 10.1016/S0031-9422(97)00830-3 (DOI)
Publication: 10.1016/j.jep.2018.07.029 (DOI)
Publication: 10.1016/j.bmc.2009.04.041 (DOI)
Publication: 10.1016/j.bmcl.2018.02.050 (DOI)
Publication: 10.1016/j.bmcl.2016.05.035 (DOI)
Publication: 10.1016/j.ejmech.2018.07.020 (DOI)
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Publication: 10.1021/jm301441w (DOI)
Publication: 10.1016/j.bmc.2006.09.028 (DOI)
Publication: 10.1021/np500271u (DOI)
Publication: 10.1007/BF01965588 (DOI)
Publication: 10.1016/0031-9422(91)85300-O (DOI)
Publication: 10.1021/np030541c (DOI)
Publication: 10.1080/10575639808048296 (DOI)
Publication: 10.1142/S0192415X16500154 (DOI)
Publication: 10.1080/10242420902811105 (DOI)
Publication: 10.1021/np0200921 (DOI)
Publication: 10.1248/cpb.51.935 (DOI)
Publication: 10.1021/acs.jmedchem.5b00058 (DOI)
Publication: 10.1016/j.phytochem.2017.10.006 (DOI)
Publication: 10.1016/j.biopha.2019.109663 (DOI)
Publication: 10.1055/a-0646-4306 (DOI)
Publication: 10.3390/ijms130911247 (DOI)
Publication: 10.1021/np5004752 (DOI)
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References

  • Binkhathlan, Z., Lavasanifar, A., 2013. P-glycoprotein inhibition as a therapeutic approach for overcoming multidrug resistance in cancer: current status and future perspectives. Curr. Cancer Drug Targets 13, 326-346. https://doi.org/10.2174/ 15680096113139990076.
  • Cary, D.C., Fujinaga, K., Peterlin, B.M., 2016. Euphorbia Kansui reactivates latent HIV. PloS One 11, e0168027. https://doi.org/10.1371/journal.pone.0168027.
  • Chen, Y.L., Yuan, D., Xu, Fu H.Z., 2008. Studies on macrocyclic jatrophane diterpenes of Euphorbia kansui. Zhongguo Zhongyao Zazhi 33, 1836-1839. PMID: 19007010.
  • Chinese Pharmacopoeia Commission, 2015. Pharmacopoeia of the People' s Republic of China, ninth ed. China Medical Science Press, Beijing, China, Volume I, p. 251.
  • Dong, M., Chen, X.Q., Chen, C.H., Li, R.T., 2018. Terpenes from Euphorbia antiquorum and their in vitro anti-HIV activity. Chem. Biodivers. 15, e1700560 https://doi.org/ 10.1002/cbdv.201700560.
  • Duarte, N., Gyemant, N., Abreu, P.M., Molnar, J., Ferreira, M.J.U., 2006. New macrocyclic lathyrane diterpenes from Euphorbia lagascae, as inhibitors of multidrug resistance of tumour cells. Planta Med. 72, 62-168. https://doi.org/10.1055/s-2005- 873196.
  • Esposito, M., Louis-Felix Nothias, L.F., Nedev, H., Gallard, J.F., Leyssen, P., Retailleau, P., Costa, J., Roussi, F., Iorga, B.I., Paolini, J., Litaudon, M., 2016. Euphorbia dendroides latex as a source of jatrophane esters: isolation, structural analysis, conformational study, and anti-CHIKV activity. J. Nat. Prod. 79, 2873-2882. https://doi.org/ 10.1021/acs.jnatprod.6b00644.
  • Gotta, H., Adolf, W., Opferkuch, H.J., Hecker, E., 1984. On the active principles of the Euphorbiaceae, IXa ingenane type diterpene esters from five Euphorbia species. Z. Naturforsch. B Chem. Sci. 39, 683-694. https://doi.org/10.1515/znb-1984-0525.
  • Gottesman, M.M., Fojo, T., Bates, S.E., 2002. Multidrug resistance in cancer: role of ATPdependent transporters. Nat. Rev. Canc. 2, 48-58. https://doi.org/10.1038/ nrc706.
  • Grue-Sorensen, G., Liang, X., Mansson, K., Vedso, P., Sorensen, M.D., Soor, A., Stahlhut, M., Malene Bertelsen, M., Engell, K.M., Hogberg ¨, H., 2014. Synthesis, biological evaluation and SAR of 3-benzoates of ingenol for treatment of actinic keratosis and non-melanoma skin cancer. Bioorg. Med. Chem. Lett 24, 54-60. https://doi.org/10.1016/j.bmcl.2013.11.073.
  • Hasan, A., Liu, G.Y., Hu, R., Aisa, H.A., 2019. Jatrophane diterpenoids from Euphorbia glomerulans. J. Nat. Prod. 82, 724-734. https://doi.org/10.1021/acs. jnatprod.8b00507.
  • Hohmann, J., R´edei, D., Forgo, P., Moln´ar, J., Dombi, G., Zorig, T., 2003. Jatrophane diterpenoids from Euphorbia mongolica as modulators of the multidrug resistance of L5128 mouse lymphoma cells. J. Nat. Prod. 66, 976-979. https://doi.org/10.1021/ np030036f.
  • Hohmann, J., Vasas, A., Gunther, G., Dombi, G., Blazso, G., Falkay, G., Mathe ´, I., Jerkovich, G., 1999. Jatrophane diterpenoids from Euphorbia peplus. Phytochemistry 51, 673-677. https://doi.org/10.1016/S0031-9422(99)00088-6.
  • Huang, Y., Lu, Y., Chen, C.H., Lee, K.H., Chen, D., 2019. Potent Anti-HIV ingenane diterpenoids from Euphorbia ebracteolata. J. Nat. Prod. 82, 1587-1592. https://doi. org/10.1021/acs.jnatprod.9b00088.
  • Jakupovic, J., Jeske, F., Morgenstern, T., Tsichritzis, F., Marco, J.A., Berendsohn, W., 1998. Diterpenes from Euphorbia segetalis. Phytochemistry 47, 1583-1600. https:// doi.org/10.1016/S0031-9422(97)00830-3.
  • Jiang, D., Kang, A., Yao, W., Lou, J., Zhang, Q., Bao, B., Cao, Y., Yu, S., Guo, S., Zhang, Y., Tang, Y., Zhang, L., 2018. Euphorbia kansui fry-baked with vinegar modulates gut microbiota and reduces intestinal toxicity in rats. J. Ethnopharmacol. 226, 26-35. https://doi.org/10.1016/j.jep.2018.07.029.
  • Jiao, W., Dong, W., Li, Z., Deng, M., Lu, R., 2009. Lathyrane diterpenes from Euphorbia lathyris as modulators of multidrug resistance and their crystal structures. Bioorg. Med. Chem. 17, 4786-4792. https://doi.org/10.1016/j.bmc.2009.04.041.
  • Kim, Y.M., Ahn, J., Chae, H.S., Choi, Y.H., Kim, J., Chin, Y.W., 2018. Two new lathyrane-type diterpenoid glycosides with IL-6 production inhibitory activity from the roots of Euphorbia kansui. Bioorg. Med. Chem. Lett 15, 1207-1210. https://doi.org/10.1016/ j.bmcl.2018.02.050.
  • Lee, J.W., Jin, Q., Jiang, H., Lee, D., Han, S.B., Kim, Y., Hong, J.T., Lee, M.K., Hwang, B. Y., 2016. Jatrophane and ingenane-type diterpenoids fro m Euphorbia kansui inhibit the LPS-induced NO production in RAW 264.7 cells. Bioorg. Med. Chem. Lett 26, 3351-3354. https://doi.org/10.1016/j.bmcl.2016.05.035.
  • Liu, Q., Li, W., Huang, L., Asada, Y., Morris-Natschke, S.L., Chen, H.H., Lee, K.H., Koike, K., 2018. Identification, structural modification, and dichotomous effects on human immunodeficiency virus type 1 (hiv-1) replication of ingenane esters from Euphorbia kansui. Eur. J. Med. Chem. 156, 618-627. https://doi.org/10.1016/j. ejmech.2018.07.020.
  • Manners, G.D., Wong, R.Y., 1985. The absolute stereochemical characterization of two new jatrophane diterpenes from Euphorbia esula. J. Chem. Soc. Perkin Trans. 1, 2075-2081. https://doi.org/10.1002/chin.198602299.
  • Mariana, R., Ferreira, R.J., Santos, M.M.M., Santos Dos, D.J.V.A., Joseph, M., Ferreira, M. J.U., 2013. Enhancing macrocyclic diterpenes as multidrug-resistance reversers: structure-activity studies on jolkinol D derivatives. J. Med. Chem. 56, 748-760. https://doi.org/10.1021/jm301441w.
  • No´elia, D., Andras, V., Georg, C., Rita, R., Joseph, M., Ferreira, M.J.U., 2007. Apoptosis induction and modulation of P-glycoprotein mediated multidrug resistance by new macrocyclic lathyrane-type diterpenoids. Bioorg. Med. Chem. 15, 546-554. https:// doi.org/10.1016/j.bmc.2006.09.028.
  • Nothias-Scaglia, L.F., Retailleau, P., Paolini, J., Pannecouque, C., Neyts, J., Dumontet, V., Roussi, F., Leyssen, P., Costa, J., Litaudon, M., 2014. Jatrophane diterpenes as inhibitors of chikungunya virus replication: structure-activity relationship and discovery of a potent lead. J. Nat. Prod. 77, 1505-1512. https://doi.org/10.1021/ np500271u.
  • Ott, H.H., Hecker, E., 1981. Highly irritant ingenane type diterpene esters from Euphorbia cyparissias L. Experientia 37, 88-91. https://doi.org/10.1007/BF01965588.
  • Pan, D.J., Hu, C.Q., Chang, J.J., Lee, T.T.Y., Chen, Y.P., Hsu, H.Y., Mcphail, D.R., Mcphail, A.T., Lee, K.Y., 1991. Kansuiphorin-C and -D, cytotoxic diterpenes from Euphorbia kansui. Phytochemistry 30, 1018-1020. https://doi.org/10.1016/0031- 9422(91)85300-O.
  • Pan, Q., Ip, F.C.F., Ip, N.Y., Zhu, H.X., Min, Z.D., 2004. Activity of macrocyclic jatrophane diterpenes from Euphorbia kansui in a TrkA fibroblast survival assay. J. Nat. Prod. 67, 1548-1551. https://doi.org/10.1021/np030541c.
  • Sekine, T., Kamiya, M., Ikegami, F., Qi, J.F., 1998. Structure of esulol A, a novel macrocyclic diterpene, from inner Mongolian Euphorbia esula. Nat. Prod. Lett. 12, 237-239. https://doi.org/10.1080/10575639808048296.
  • Shen, J., Kai, J., Tang, Y., Zhang, L., Su, S., Duan, J.A., 2016. The chemical and biological properties of Euphorbia kansui. Am. J. Chin. Med. 44, 253-257. https://doi.org/ 10.1142/S0192415X16500154.
  • Teng, R.W., Teng, R.W., Mcmanus, D., Teng, R.W., Mcmanus, D., Aylward, J., Ogboume, S., Armstrong, D., Mau, J., Johns, J., 2009. Biotransformation of ingenol- 3-angelate in four plant cell suspension cultures. Biocatalysis 27, 186-194. https:// doi.org/10.1080/10242420902811105.
  • Wang, L.Y., Wang, N.L., Yao, X.S., Miyata, S., Kitanaka, S., 2002. Diterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of xenopus. J. Nat. Prod. 65, 1246-1251. https://doi.org/10.1021/np0200921.
  • Wang, L.Y., Wang, N.L., Yao, X.S., Miyata, S., Kitanaka, S., 2003. Diterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of xenopus. Chem. Pharm. Bull. 51, 935-941. https://doi.org/10.1248/cpb.51.935.
  • Wei, J., Wang, Z., Chen, S., Lu, R., Chen, X., Fang, D., Wang, J., Pu, S., Huang, X., Gao, H., Shao, H., 2015. Lathyrol diterpenes as modulators of P-glycoprotein dependent multidrug resistance: structure-activity relationship studies on Euphorbia factor L3 derivatives. J. Med. Chem. 58, 3720-3738. https://doi.org/10.1021/acs. jmedchem.5b00058.
  • Wu, X., Pan, Q., Li, Y.Y., Yang, Y., Guan, Y.Z., Wu, X.L., Sun, C.T., Wang, Y., 2018. 13- oxidized ingenol derivative and use thereof. WO2018224007A1.
  • Yan, S.L., Li, Y.H., Chen, X.Q., Liu, D., Chen, C.H., Li, R.T., 2018. Diterpenes from the stem bark of Euphorbia neriifolia and their in vitro anti-HIV activity. Phytochemistry 145, 40-47. https://doi.org/10.1016/j.phytochem.2017.10.006.
  • Yang, T., Wang, S.Y., Li, H.M., Zhao, Q., Yan, S.L., Dong, M., Liu, D., Chen, X.Q., Li, R.T., 2020. Lathyrane diterpenes from Euphorbia lathyris and the potential mechanism to reverse the multi-drug resistance in HepG2/ADR cells. Biomed. Pharmacother. 121, 109663. https://doi.org/10.1016/j.biopha.2019.109663.
  • Zhang, J.S., Weng, H.Z., Huang, J.L., Tang, G.H., Yin, S., 2018. Anti-inflammatory ingenane diterpenoids from the roots of Euphorbia kansui. Planta Med. 84, 1334-1339. https://doi.org/10.1055/a-0646-4306.
  • Zhang, L., Gao, L., Li, Z., Yan, X., Yang, Y., Tang, Y., Cao, Y., Ding, A., 2012. Bio-guided isolation of the cytotoxic terpenoids from the roots of Euphorbia kansui against human normal cell lines L-O2 and GES-1. Int. J. Mol. Sci. 13, 11247-11259. https:// doi.org/10.3390/ijms130911247.
  • Zhao, J., Liu, C., Qi, W., Han, M., Han, Y., Wainberg, M.A., Yue, J., 2014. Eurifoloids A-R, structurally diverse diterpenoids from Euphorbia neriifolia. J. Nat. Prod. 77, 2224-2233. https://doi.org/10.1021/np5004752.