Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su"
- PMID: 12141860
- DOI: 10.1021/np0200360
Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su"
Abstract
Steroid bufenolides resulting from epoxidation of the 17beta-2-pyrone ring of bufadienolides are rare. Five 20,21-epoxybufenolides, namely, 20S,21-epoxyresibufogenin (1), 20R,21-epoxyresibufogenin (2), 3-O-formyl-20S,21-epoxyresibufogenin (3), 3-O-formyl-20R,21-epoxyresibufogenin (4), and 3-oxo-20S,21-epoxyresibufogenin (5), were isolated from the Chinese toad skin extract drug Ch'an Su. The structures were elucidated by spectroscopic and chemical methods. The configuration at C-20 was assigned by the analysis of difference NOE spectra. The cancer cell (KB and MH-60) growth inhibition by the new 20,21-epoxybufenolides was examined, and 20,21-epoxides 1, 2, and 5 were found to significantly inhibit the leukemia MH-60 cell line.
Similar articles
-
Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch'an Su.J Nat Prod. 2001 Sep;64(9):1148-52. doi: 10.1021/np0101088. J Nat Prod. 2001. PMID: 11575946
-
A new bufadienolide with cytotoxic activity from the Chinese traditional drug Ch'an Su.Chin J Nat Med. 2014 Aug;12(8):623-7. doi: 10.1016/S1875-5364(14)60095-9. Chin J Nat Med. 2014. PMID: 25156289
-
Inhibitory effects of bufadienolides on interleukin-6 in MH-60 cells.J Nat Prod. 2004 Dec;67(12):2070-2. doi: 10.1021/np049950e. J Nat Prod. 2004. PMID: 15620253
-
Bufadienolides and their antitumor activity.Nat Prod Rep. 2011 May;28(5):953-69. doi: 10.1039/c0np00032a. Epub 2011 Mar 17. Nat Prod Rep. 2011. PMID: 21416078 Review. No abstract available.
-
Bufadienolides from amphibians: A promising source of anticancer prototypes for radical innovation, apoptosis triggering and Na+/K+-ATPase inhibition.Toxicon. 2017 Mar 1;127:63-76. doi: 10.1016/j.toxicon.2017.01.004. Epub 2017 Jan 7. Toxicon. 2017. PMID: 28069354 Review.
Cited by
-
Configurational reassignment and improved preparation of the competitive IL-6 receptor antagonist 20R,21R-epoxyresibufogenin-3-formate.J Nat Prod. 2012 Apr 27;75(4):661-8. doi: 10.1021/np2008957. Epub 2012 Feb 23. J Nat Prod. 2012. PMID: 22360661 Free PMC article.
-
The cephalostatins. 22. synthesis of bis-steroidal pyrazine pyrones (1).J Nat Prod. 2012 Jun 22;75(6):1063-9. doi: 10.1021/np300069z. Epub 2012 May 18. J Nat Prod. 2012. PMID: 22607450 Free PMC article.
-
Emergence of 2-Pyrone and Its Derivatives, from Synthesis to Biological Perspective: An Overview and Current Status.Top Curr Chem (Cham). 2021 Sep 23;379(6):38. doi: 10.1007/s41061-021-00350-w. Top Curr Chem (Cham). 2021. PMID: 34554344 Review.
-
Interleukin-6: Molecule in the Intersection of Cancer, Ageing and COVID-19.Int J Mol Sci. 2020 Oct 26;21(21):7937. doi: 10.3390/ijms21217937. Int J Mol Sci. 2020. PMID: 33114676 Free PMC article. Review.
-
3α-Hydroxybufadienolides in Bufo gallbladders: structural insights and biotransformation.Nat Prod Bioprospect. 2024 Mar 4;14(1):19. doi: 10.1007/s13659-024-00442-2. Nat Prod Bioprospect. 2024. PMID: 38436763 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
