808-19-5Relevant articles and documents
BIOSYNTHESIS OF THE BUTENOLIDE RING OF CARDENOLIDES IN DIGITALIS PURPUREA
Maier, Marta S.,Seldes, Alicia M.,Gros, Eduardo G.
, p. 1327 - 1330 (1986)
Administration of labelled 3β20ξ-dihydroxy-23-norchol-5-enoic acid, 3-oxo-20ξ-hydroxy-23-norchol-4-enoic acid, 3β,20ξ-dihydroxy-23-nor-5β-cholanoic acid, 3β,14β,20ξ-trihydroxy-23-nor-5β-cholanioc acid, 3β-hydroxy-23-norchola-5,20(22)E-dienoic acid, 3-oxo-23-norchola-4,20(22)E-dienoic acid and 3β-hydroxy-23-nor-5β-chol-20(22)E-enoic acid to Digitalis purpurea intact plants produced labelled digitoxin and gitoxin.The incorporation results indicate the existence of an alternative pathway, via norcholanoic acid derivatives, for the biosynthesis of the butenolide ring of cardenolides.Key Word Index - Digitalis purpurea; Scrophulariaceae; foxglove; cardenolide; biosynthesis; digitoxin; gitoxin; norcholanoic acids.
Steroids and related products. XLVII. Cardiotonic steroids. VII. The 14β-hydroxylation of 17β-substituted steroids. Part II
Engel Ch.,Mukherjee
, p. 73 - 79 (1981)
The most efficient method for introducing a 14β-hydroxy group into a steroid with a 17β-side chain is reported. It can be used in the presence of an unsaturated lactone ring.
17BETA-HETEROCYCLYL-DIGITALIS LIKE COMPOUNDS FOR THE TREATMENT OF HEART FAILURE
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Paragraph 0112-0115; 0132-0134, (2020/02/13)
Disclosed are compounds of formula (I) wherein X, Y, Z are annular atoms comprised in a five-membered carbocyclic or heterocyclic ring, selected from the group consisting of CH, NH, N, O, S; said carbocyclic or heterocyclic ring being optionally substituted with amino (C1-C4) linear or branched alkyl or guanidine or guanidino (C1-C4) linear or branched alkyl; with the proviso that the heterocycle ring is not furyl; n is 0 or 1; R is H or OH; the dotted line represents an optional double bond C=C; the thick line represents a bond in the β configuration; the wavy line represents a bond both in the α and β configuration; their enantiomeric and/or diastereomeric mixtures, their pharmaceutically acceptable salts, their solvates, hydrates; their metabolite and metabolic precursors. The compounds of formula (I) are for use as medicaments, in particular for the treatment of acute or chronic heart failure. Oral administration is also possible.
Digitoxigenin-3-O-β-D-glucopyranoside from the roots of Sapium sebiferum
Bose, Chandana
experimental part, p. 1252 - 1254 (2012/01/13)
The plant Sapium sebiferum is commonly known as Vilayati shisham in Hindi and belongs to natural order Euphorbiaceae. The plant is widely cultivated in India. The ethyl acetate soluble fraction of the concentrated ethyl alcohol soluble part of its roots when subjected to column chromatography yielded a yellow coloured compound, m.f. C29H44O9, m.p. 200-201 °C [α]D -19.3°, M+ = 536, which on various chemical degradations, colour reactions and spectral analysis was identified as digitoxigenin-3-O-β-D-glucopyranoside AC-4.
A simple chemical method for synthesizing malonyl hemiesters of 21-hydroxypregnanes, potential intermediates in cardenolide biosynthesis
Padua, Rodrigo M.,Waibel, Reiner,Kuate, Serge Philibert,Schebitz, Pia K.,Hahn, Stefanie,Gmeiner, Peter,Kreis, Wolfgang
, p. 458 - 465 (2008/09/17)
A simple and versatile method for the chemical synthesis of 21-hydroxypregnane 21-O-malonyl hemiesters which may be important intermediates of cardenolide biosynthesis is described. Starting from commercial β-methyldigitoxin, acid hydrolysis followed by 3β-O-acetylation and ozonolysis with reductive cleavage of the ozonides afforded 3β-acetoxy-5β-pregnane-14β,21-diol-20-one which was finally converted into the target compound by treatment with malonyl chloride. The malonylation protocol was optimized using deoxycorticosterone (DOC) as the pregnane educt.
Does the malonyl-coenzyme A:21-hydroxypregnane 21-hydroxy-malonyltransferase catalyze the first step in the formation of the butenolide ring of cardenolides?
Stuhlemmer,Kreis
, p. 2221 - 2224 (2007/10/03)
An enzyme catalyzing the transfer of the malonyl moiety from malonyl-coenzyme A 1 to the 21-hydroxy group of 3β, 14β, 21-trihydroxy-5β-pregnane-20-one 2 was isolated from Digitalis lanata leaves and characterized. The role of this particular enzyme in cardenolide biosynthesis is discussed.
13C NMR Spectra of 5β,14β-Hydroxysteroids
Habermehl, Gerhard G.,Hammann, Peter E.,Wray, Victor
, p. 959 - 963 (2007/10/02)
The 13C chemical shifts of 30 substituted 5β,14β-hydroxysteroids are described and discussed.Substituent chemical shifts for 12α- and 12β-hydroxy groups were evaluated, and interesting γ effects were observed.A correlation is shown to exist between the 1H shifts of H-17 and the 13C shifts of C-17 for various C-12 substituents.A relationship for the distance of the substituent at C-12 from H-17 in the 14β,20-lactones was demonstrated, where an increased distance between these atoms is associated with smaller shift differences.
Partial Syntheses of Cardenolides and Cardenolide Analogues. VI. (20R)- and (20S)-Cardanolides
Lindig, Claus,Repke, Kurt R. H.
, p. 574 - 586 (2007/10/02)
(20R)-Dihydrodigitoxigenin (2) and (20S)-dihydrodigitoxigenin (4) as well as their 3-acetates 3 and 5, respectively, were synthesized by catalytic hydrogenation of the appropriate cardenolides and separation by column chromatography on silica of the mixtures of stereoisomers.Hydroxymethylation of 3 and 5 followed by selective elimination yielded (20S)- and (20R)-14-hydroxy-22-methylene-5β,14β-cardanolide 3-acetate (10 and 16), respectively.The biological activities of the synthesized 20-stereoisomeric cardanolides are investigated and discussed.Cardanolides 10 and 16 have a strong inhibitory activity on the proliferation of Ehrlich ascites carcinoma cells in suspension culture.
