Citation: ZHANG Yuan, FENG Juan, YE Wen-Cai, TIAN Hai-Yan, JIANG Ren-Wang. Crystal Structure and Anticancer Properties of Cinobufagin 3-Hemisuberate Methyl Ester[J]. Chinese Journal of Structural Chemistry, ;2014, 33(5): 790-794. shu

Crystal Structure and Anticancer Properties of Cinobufagin 3-Hemisuberate Methyl Ester

1.
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China

Corresponding author: JIANG Ren-Wang,
Received Date: 28 November 2013
Available Online: 26 December 2013
Fund Project: This work was supported by the National Natural Science Foundation of China (81102518) (81102518)

The title compound cinobufagin 3-hemisuberate methyl ester (1) was isolated from the venom of Bufo bufo gargarizans CANTOR. The crystal structure of 1, C₃₅H₄₈O₉, was determined by single-crystal X-ray diffraction analysis. It belongs to orthorhombic, space group P2₁2₁2₁ with a=8.9338(3), b=16.2970(4), c=22.4019(6)Å, V=3261.59(16)Å³, M_r=612.73, Z=4, D_c=1.248 g/cm³, μ=0.725 mm^-1, F(000)=1320, S=1.040, the final R=0.0374 and wR=0.0412 for 4458 unique reflections, of which 4088 were observed (I>2σ(I)). In the solid state, short intermolecular C-H…O interactions involving a methine and the ester carbonyl group in cinobufagin moiety and a methyl in the suberate moiety linked adjacent molecules into a three-dimensional network. Detailed analysis of the ¹H-NMR data showed that X-ray structure of 1 would be expected to closely resemble the solution conformation in chloroform. Compound 1 was inactive for the inhibition of PC3 and HepG2 cancer cells, but the parent compound cinobufagin showed potent inhibition with IC₅₀ values of 0.145 and 5.48 μM, respectively, indicating that esterification at C(3) decreased the cytotoxic effect of 1.
- crystal structure,
- cinobufagin 3-hemisuberate methyl ester,
- anticancer
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