Abstract
Euphorbia microsciadia (Euphorbiaceae) is a perennial plant growing in Iran. Two new cyclomyrsinol esters, 3-O-propionyl-5, 10, 14-O-triacetyl-8-O-(2′-methyl-butanoyl)-cyclomyrsinol (1) and 3, 5, 10, 14, 15-O-pentaacetyl-8-O-isobutanoyl-cyclomyrsinol (2) were isolated from the methanolic extract of its dried aerial parts. The structures were elucidated based on 13C- and 1H-NMR as well as 2D-NMR, IR and different MS spectra. Anti-angiogenic activity was also evaluated on vascular endothelium growth factor (VEGF)-induced angiogenesis in cultured human umbilical vein endothelial cells in vitro by assessing capillary-like tube network formation.
Similar content being viewed by others
References
Appendino G, Jakupovic S, Tron CG, Jakupovic J, Milon V, Ballero M (1998) Macrocyclic diterpenoids from Euphorbia semiperfoliata. J Nat Prod 61:749–756
Ayatollahi AM, Ghanadian M, Mesaik MA, Omer MA, Afsharypuor S, Kobarfard F, Mirza-taheri M (2010) New myrsinane-type diterpenoids from Euphorbia aellenii Rech. f. with their immunomodulatory activity. J Asian Nat Prod Res 12:1020–1025
Ebn-e Sina A (1998) Ghanoon dar Teb, vol 5. Soroush, Tehran
Hussain S, Slevin M, Mesaik MA, Choudhary MI, Elosta AH, Matou S, Ahmed N, West D, Gaffney J (2008) Cheiradone: a vascular endothelial cell growth factor receptor antagonist. BMC Cell Biol 29:7–9
Tugues S, Koch S, Gualandi L, Li X, Claesson-Welsh L (2011) Vascular endothelial growth factors and receptors: anti-angiogenic therapy in the treatment of cancer. Mol Aspects Med 32:88–111
Viquar-Uddin A, Jassbi AR (1999) New diterpenoids from Euphorbia teheranica. J Nat Prod 62:1016–1018
Wang H, Zhang X, Zhou Y, Peng S, Zhou D, Ding L (2008) Two new diterpenes from Euphorbia kansuensis. Fitoterapia 79:262–266
Li J, Xu L (2010) New cytotoxic myrsinane-type diterpenes from Euphorbia prolifera. Helv Chim Acta 93:746–1752
Ayatollahi AM, Ghanadian M, Afsharypuor S, Choudhary MI, Kobarfard F, Rahmati M (2010) Two new lathyrane type diterpenoids from Euphorbia aellenii. Fitoterapia 81:891–893
Arnaoutova I, Kleinman HK (2010) In vitro angiogenesis: endothelial cell tube formation on gelled basement membrane extract. Nat Protoc 5:628–635
Niemisto A, Dunmire V, Yli-Harja O, Zhang W, Shmulevich I (2005) Robust quantification of in vitro angiogenesis through image analysis. IEEE Trans Med Imaging 24:549–553
Scholz G, Pohl I, Genschow E, Klemm M, Spielmann H (1999) Embryotoxicity screening using embryonic stem cells in vitro: correlation to in vivo teratogenicity. Cells Tissues Organs 165:203–211
Ahmadvand D, Rahbarizadeh F, Jafari Iri-Sofla F, Namazi G, Khaleghi S, Geramizadeh B, Pasalar P, Karimi H, Aghaee Bakhtiari SH (2010) Inhibition of angiogenesis by recombinant VEGF receptor fragments. Lab Med 41:417–422
Acknowledgments
The authors are grateful to Prof. Dr. Muhammad Iqbal Choudhary, and the H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, for their generous support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ghanadian, S.M., Ayatollahi, A.M., Afsharypuor, S. et al. New mirsinane-type diterpenes from Euphorbia microsciadia Boiss. with inhibitory effect on VEGF-induced angiogenesis. J Nat Med 67, 327–332 (2013). https://doi.org/10.1007/s11418-012-0686-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-012-0686-3