Bufadienolides and polyhydroxycholestane derivatives from Bufo bufo gargarizans

A new polyhydroxycholestane sulfate ester, 3α,12β,25,26-tetrahydroxy-7-oxo-5β-cholestane 26-O-sulfate (1), was isolated from dried skin of Bufo bufo gargarizans Cantor and its structure was elucidated on the basis of extensive 1D and 2D NMR as well as HR-ESI-MS analysis. A comparison of steroidal metabolite profiles, based on HPLC and LC–MS analyses, indicates that the chemical compositions of the various parts of toads, such as venom, skin and stratum corneum, are significantly different.

[1]  H. Parekh,et al.  Rapid identification of primary constituents in parotoid gland secretions of the Australian cane toad using HPLC/MS-Q-TOF. , 2013, Biomedical chromatography : BMC.

[2]  R. Kiss,et al.  Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells. , 2013, Journal of natural products.

[3]  Zhiling Yu,et al.  Comprehensive chemical analysis of Venenum Bufonis by using liquid chromatography/electrospray ionization tandem mass spectrometry. , 2011, Journal of pharmaceutical and biomedical analysis.

[4]  A. Leitner,et al.  Comparison of toad venoms from different Bufo species by HPLC and LC-DAD-MS/MS. , 2010, Journal of ethnopharmacology.

[5]  R. Kiss,et al.  Rapid structural identification of cytotoxic bufadienolide sulfates in toad venom from Bufo melanosticus by LC-DAD-MS(n) and LC-SPE-NMR. , 2010, Journal of natural products.

[6]  Ying Zhang,et al.  Pilot study of huachansu in patients with hepatocellular carcinoma, nonsmall‐cell lung cancer, or pancreatic cancer , 2009, Cancer.

[7]  Andrew M. Piggott,et al.  Microbial biotransformation as a source of chemical diversity in cane toad steroid toxins. , 2009, Bioorganic & medicinal chemistry letters.

[8]  M. Ye,et al.  Simultaneous determination of cytotoxic bufadienolides in the Chinese medicine ChanSu by high-performance liquid chromatography coupled with photodiode array and mass spectrometry detections. , 2006, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[9]  Kazuhide Inoue,et al.  5α-Bile alcohols function as farnesoid X receptor antagonists , 2006 .

[10]  M. Ye,et al.  Novel cytotoxic bufadienolides derived from bufalin by microbial hydroxylation and their structure–activity relationships , 2004, The Journal of Steroid Biochemistry and Molecular Biology.

[11]  J. Zhan,et al.  Biotransformation of cinobufagin by cell suspension cultures of Catharanthus roseus and Platycodon grandiflorum , 2003 .

[12]  T. Nambara,et al.  Occurrence of bufogenin conjugates in the skin of Korean toad. , 1987, Chemical & pharmaceutical bulletin.

[13]  倉本 戴寿,et al.  Determination of the sulfated position in 5.BETA.-bufol sulfate by a carbon-13 nuclear magnetic resonance study. , 1981 .

[14]  Y. Fujii,et al.  Studies on cardiotonic steroids from the skin of Japanese toad. , 1977, Chemical & pharmaceutical bulletin.