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Chemical Synthesis of the Cardiotonic Steroid Glycosides and Related Natural Products
Author(s) -
Heasley Brian
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103733
Subject(s) - cardenolide , aglycone , steroid , glycoside , inotrope , cardiac glycoside , chemistry , digitalis , intracellular , pharmacology , digoxin , biology , biochemistry , heart failure , ouabain , sodium , stereochemistry , medicine , endocrinology , hormone , organic chemistry
The active components from the extracts of Digitalis , cardiotonic steroid glycosides, have been ingested by humans for more than 200 years as a medicinal therapy for heart failure and abnormal heart rhythms. The positive inotropic activity of the cardiotonic steroids that mediates clinically useful physiological effects in patients has been attributed largely to a high affinity inhibitory interaction with the extracellular surface of the membrane‐bound sodium pump (Na + /K + ‐ATPase). However, previously unrecognized intracellular signaling pathways continue to be uncovered. This Review examines both partial and de novo synthetic approaches to the medicinally important and structurally captivating cardenolide and bufadienolide steroid families, with an emphasis on the stereocontrolled construction of the pharmacophoric aglycone (genin) framework.