Bufadienolide

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General structural formula of bufadienolides

Bufadienolides are a group of chemical compounds found naturally in various species of eukaryotes and a subgroup of steroids . In real toads ( Bufo sp. ), Representatives of this group of substances are found in the skin glands, from which the name bufadienolide is derived. In the plant families of the Scilloideae (also Hyacinthaceae , such as white squill Urginea maritima ) and the buttercup family ( Ranunculaceae , such as snow lily Helleborus niger ), bufadienolides occur as secondary metabolites .

From a chemical point of view, bufadienolides are steroids with a δ- lactone residue at position 17 and thus derivatives of bufotaline . They are homologous to the cardenolides , which bind a γ-lactone instead of the δ-lactone. Bufadienolides inhibit the Na + / K + -ATPase , preferably the isoform Alpha1. Just like the cardenolides, bufadienolides slow the beat frequency of the myocardium and the conduction of the myocardial cells and are therefore toxic. The cardio-active endogenous steroids ( cardiotonic steroids ) include the endogenous ouabain (a cardenolide), the bufadienolides bufalin, marinobufagenin (MBG) and telocinobufagin.

Various bufadienolides are used to diagnose and treat preeclampsia . Marinobufagenin is used for prognosis and resibufogenin is used for prevention. Various bufadienolides have anti- tumor effects.

Individual evidence

  1. ↑ Hildebert Wagner: Pharmaceutical Biology, Volume 2. Drugs and their ingredients , Gustav Fischer Verlag, Stuttgart 1980.
  2. Jump up ↑ DL Wang, FH Qi, W. Tang, FS Wang: Chemical constituents and bioactivities of the skin of Bufo bufo gargarizans Cantor. In: Chemistry & biodiversity. Volume 8, number 4, April 2011, pp. 559-567, doi : 10.1002 / cbdv.201000283 . PMID 21480502 .
  3. ↑ Entry on Bufadienolide. In: Römpp Online . Georg Thieme Verlag, accessed on September 22, 2013.
  4. ↑ JB Puschett, E. Agunanne, MN Uddin: Emerging role of the bufadienolides in cardiovascular and kidney diseases. In: American Journal of Kidney Diseases . Volume 56, Number 2, August 2010, pp. 359-370. doi : 10.1053 / j.ajkd.2010.01.023 . PMID 20417001 .
  5. ↑ OV Fedorova, AS Simbirtsev, NI Kolodkin, AY Kotov, NI Agalakova, VA Kashkin, NI Tapilskaya, A. Bzhelyansky, VA Reznik, EV Frolova, ER Nikitina, GV Budny, DL Longo, EG Lakatta, AY Bagrov: Monoclonal antibody to an endogenous bufadienolide, marinobufagenin, reverses preeclampsia-induced Na / K-ATPase inhibition and lowers blood pressure in NaCl-sensitive hypertension. In: Journal of hypertension. Volume 26, Number 12, December 2008, pp. 2414-2425, doi : 10.1097 / HJH.0b013e328312c86a . PMID 19008721 . PMC 2583455 (free full text).
  6. ↑ JB Puschett: Marinobufagenin predicts and resibufogenin prevents preeclampsia: a review of the evidence. In: American journal of perinatology. Volume 29, Number 10, November 2012, pp. 777-785, doi : 10.1055 / s-0032-1316447 . PMID 22814872 .
  7. ^ H. Gao, R. Popescu, B. Kopp, Z. Wang: Bufadienolides and their antitumor activity. In: Natural Product Reports . Volume 28, Number 5, May 2011, pp. 953-969, doi : 10.1039 / c0np00032a . PMID 21416078 .