Glucosylation of Digitoxin and Other Cardenolides in Cell Cultures of Digitalis lanata

Diettrich, B.; Aster, U.; Greidziak, N.; Roos, Werner; Luckner, Martin

doi:10.1016/s0015-3796(87)80050-1

Cited by 14 publications

(1 citation statement)

References 18 publications

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“…The 4″- O -glucosylated product 5 corresponds to the naturally occurring purpurea glycoside A (desacetyl lanatoside A) . To date, the only reported conversions of digitoxin into purpurea glycoside A have made use of whole cell extracts, usually from Digitalis species . Given the modest levels of amplification of purpurea glycoside A that have been reported in such studies, the preparative utility of the two-step sequence described here may compare favorably with those of the biotransformation-based protocols.…”

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confidence: 97%

Synthesis of Cardiac Glycoside Analogs by Catalyst-Controlled, Regioselective Glycosylation of Digitoxin

Beale

Taylor

2013

Org. Lett.

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The cardiac glycoside natural product digitoxin was selectively glycosylated at one of its five hydroxyl groups using a borinic acid derived catalyst. This method provided access to the glycosylation pattern characteristic of a subclass of natural products from Digitalis purpurea. Variation of the glycosyl donor was tolerated, enabling the synthesis of novel cardiac glycoside analogs from readily available materials.

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confidence: 97%

Synthesis of Cardiac Glycoside Analogs by Catalyst-Controlled, Regioselective Glycosylation of Digitoxin

Beale

Taylor

2013

Org. Lett.

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Metabolism of the pesticide metabolites 4‐nitrophenol and 3,4‐dichloroaniline in carrot (Daucus carota) cell suspension cultures

1994

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The metabolism of [ 14 C]‐4‐nitrophenol and [ 14 C]‐3,4‐dichloroaniline (the xenobiotics are degradation products of parathion and propanil, respectively) was studied in cell suspension cultures of carrot (Daucus carota L.). 4‐Nitrophenol was transformed almost quantitatively to water‐soluble conjugates with minor amounts of non‐extractable residues. The conjugates identified were 1‐(O‐β‐D‐glucopyranosyl)‐4‐nitrobenzene and 1‐(6′‐O‐malonyl‐O‐β‐D‐glucopyranosyl)‐4‐nitrobenzene. In addition, two unidentified metabolites were observed, possibly a disaccharide and another malonylated glycoside of 4‐nitrophenol. Time‐course studies demonstrated that 4‐nitrophenol was rapidly taken up and conjugated; all metabolites remained associated with the cells rather than nutrient medium. 3,4‐Dichloroaniline was transformed quantitatively to water‐soluble conjugates and bound residues (3.6%). The water‐soluble metabolites were identified as 6′‐O‐malonyl‐N‐(β‐D‐glucopyranosyl)‐3,4‐dichloroaniline, N‐(β‐D‐glucopyranosyl)‐3,4‐dichloroaniline and N‐malonyl‐3,4‐dichloroaniline. A time‐course study showed that the glucosides were formed initially, then decreased, possibly due to hydrolysis. This decrease was paralleled by an increase of the main metabolite, N‐malonyl‐3,4‐dichloroaniline, which was predominantly recovered from the medium.

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The Integration of Cardenolide Biosynthesis in the Differentiation Program “Somatic Embryogenesis” of Digitalis lanata

Luckner¹,

Diettrich

1989

Primary and Secondary Metabolism of Plant Cell Cultures II

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Glucosylation of Digitoxin and Other Cardenolides in Cell Cultures of Digitalis lanata

Cited by 14 publications

References 18 publications

Synthesis of Cardiac Glycoside Analogs by Catalyst-Controlled, Regioselective Glycosylation of Digitoxin

Synthesis of Cardiac Glycoside Analogs by Catalyst-Controlled, Regioselective Glycosylation of Digitoxin

Metabolism of the pesticide metabolites 4‐nitrophenol and 3,4‐dichloroaniline in carrot (Daucus carota) cell suspension cultures

The Integration of Cardenolide Biosynthesis in the Differentiation Program “Somatic Embryogenesis” of Digitalis lanata

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