Three new myrsinol diterpenes were isolated from the roots of Euphorbia prolifera. Their structures were elucidated as 2α-O-isobutyryl-3β,5α,7β,10,15β-penta-O-acetyl-14α-O-benzoyl-10,18-dihydromyrsinol (1), 2α-O-isobutyryl-3β-O-propion-yl-5α,7β,10,15β-tetra-O-acetyl-10,18-dihydromyrsinol (2), and 2α,14α-di-O-benzoyl-3β,5α,7β,10,15β-penta-O-acetyl-10,18-dihydromyrsinol (3) on the basis of spectroscopic data analyses (IR, ESI-MS, HR-ESI-MS, and 1D and 2D NMR). Their neuroprotective activities were evaluated and compounds 1 and 2 showed neuroprotective effects against MPP+-induced neuronal cell death in SH-SY5Y cells.
References
[1]
Editorial Committee of Flora of China, Chinese Academy of Sciences. Flora of China; Science Press: Beijing, China, 1997; Volume 44, pp. 118–121.
[2]
Wu, D.G.; Sorg, B.; Hecker, E. Oligo- and macrocyclicditerpenes in Thymelaeaceae and Euphorbiaceae occurring and utilized in Yunnan (Southwest China). 6. Tigliane type diterpene esters from latex of Euphorbia prolifera. Phytother. Res. 1994, 8, 95–99, doi:10.1002/ptr.2650080209.
[3]
Wu, D.; Sorg, B.; Hecker, E. New myrsinol-related polyfunctionalpentacyclicditerpene esters from roots of Euphorbia prolifera. J. Nat. Prod. 1995, 58, 408–413, doi:10.1021/np50117a009.
[4]
Zhang, W.J.; Chen, D.F.; Hou, A.J. New myrsinolditerpenes from Euphorbia prolifera. Chin. J. Chem. 2004, 22, 103–108.
[5]
Li, J.; Xu, L.; Wang, F.P. New cytotoxicmyrsinane-type diterpenes from Euphorbia prolifera. Helv. Chim. Acta 2010, 93, 746–752, doi:10.1002/hlca.200900288.
[6]
Xu, J.; Guo, Y.; Xie, C.; Li, Y.; Gao, J.; Zhang, T.; Hou, W.; Fang, L.; Gui, L. Bioactive myrsinolditerpenoids from the roots of Euphorbia prolifera. J. Nat. Prod. 2011, 74, 2224–2230, doi:10.1021/np200591h.
[7]
Xu, J.; Jin, D.Q.; Guo, Y.; Xie, C.; Ma, Y.; Yamakuni, T.; Ohizumi, Y. New myrsinolditerpenes from Euphorbia prolifera and their inhibitory activities on LPS-induced NO production. Bioorg. Med. Chem. Lett. 2012, 22, 3612–3618, doi:10.1016/j.bmcl.2012.04.052.
[8]
Rizk, A.-F.M. The chemical constituents and economic plants of the Euphorbiaceae. Bot. J. Linnean Soc. 1987, 94, 293–326, doi:10.1111/j.1095-8339.1987.tb01052.x.
[9]
Zhang, W.J.; Chen, D.F.; Hou, A.J. Two novel myrinsolditerpenes from Euphorbia prolifera. Chin. Chem. Lett. 2002, 13, 744–747.
[10]
Xu, J.; Zhang, P.; Ma, Z.; Guo, Y.; Zhao, X.; Wei, K. Two carabrane-type sesquiterpenes from Vladimiria souliei. Phytochem. Lett. 2009, 2, 204–206, doi:10.1016/j.phytol.2009.08.001.
[11]
Guo, P.; Li, Y.; Xu, J.; Liu, C.; Ma, Y.; Guo, Y. Bioactive neo-clerodanediterpenoids from the whole plants of Ajuga ciliata Bunge. J. Nat. Prod. 2011, 74, 1575–1583, doi:10.1021/np2001557.
[12]
Dawson, T.M.; Dawson, V.L. Molecular pathways of neurodegeneration in Parkinson’s disease. Science 2003, 302, 819–822, doi:10.1126/science.1087753.
[13]
Vasas, A.; Sulyok, E.; Martins, A.; Rédei, D.; Forgo, P.; Kele, Z.; Zupkó, I.; Molnár, J.; Pinke, G.; Hohmann, J. Cyclomyrsinane and premyrsinanediterpenes from Euphorbia falcata modulate resistance of cancer cells to doxorubicin. Tetrahedron 2012, 68, 1280–1285, doi:10.1016/j.tet.2011.11.039.
[14]
Shi, Q.W.; Su, X.H.; Kiyota, H. Chemical and pharmacological research of the plants in genus Euphorbia. Chem. Rev. 2008, 108, 4295–4327, doi:10.1021/cr078350s.
[15]
Xu, J.; Guo, Y.; Li, Y.; Zhao, P.; Liu, C.; Ma, Y.; Gao, J.; Hou, W.; Zhang, T. Sesquiterpenoids from the resinous exudates of Commiphora myrrha and their neuroprotective effects. Planta Med. 2011, 77, 2023–2028, doi:10.1055/s-0031-1280087. 21830185
[16]
Xu, J.; Yang, B.; Guo, Y.; Jin, D.Q.; Guo, P.; Liu, C.; Hou, W.; Zhang, T.; Gui, L.; Sun, Z. Neuroprotective bakkenolides from the roots of Valeriana jatamansi. Fitoterapia 2011, 82, 849–853, doi:10.1016/j.fitote.2011.04.012.
