Spontaneous butenolide ring formation of pregnane-21-O-malonyl hemiesters under mild reaction conditions is facilitated by the 14β-hydroxy group present in all natural cardenolides

Pádua, Rodrigo Maia de; Meitinger, Nadine; Hennemann, Matthias; Schebitz, P.; Waibel, Reiner; Löber, Stefan; Gmeiner, Peter; Clark, Timothy; Kreis, Wolfgang

doi:10.1016/j.tet.2016.06.024

Cited by 4 publications

(1 citation statement)

References 14 publications

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“…The formation of the butenolide ring system can be accomplished by formal elimination of water and lactonization. Spontaneous butenolide ring formation of pregnane-21-O-malonyl hemiesters under mild reaction conditions was shown to be facilitated by the 14β-hydroxy group present in all natural cardenolides [135,136]. When 5β-pregnane-14β,21-diol-20-ones were incubated with malonyl coenzyme A in a cell-free extract of D. lanata leaves, a product was formed which was identified as the malonyl hemiester of the substrate [137].…”

Section: Biosynthesis Of Cardenolidesmentioning

confidence: 99%

The Foxgloves (Digitalis) Revisited

Kreis

2017

Planta Med

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This review provides a renewed look at the genus Digitalis. Emphasis will be put on those issues that attracted the most attention or even went through paradigmatic changes since the turn of the millennium. PubMed and Google Scholar were used (“Digitalis” and “Foxglove” were the key words) to identify research from 2000 till 2017 containing data relevant enough to be presented here. Intriguing new results emerged from studies related to the phylogeny and taxonomy of the genus as well as to the biosynthesis and potential medicinal uses of the key active compounds, the cardiac glycosides. Several Eastern and Western Foxgloves were studied with respect to their propagation in vitro. In this context, molecular biology tools were applied and phytochemical analyses were conducted. Structure elucidation and analytical methods, which have experienced less exciting progress, will not be considered here in great detail.

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Section: Biosynthesis Of Cardenolidesmentioning

confidence: 99%

The Foxgloves (Digitalis) Revisited

Kreis

2017

Planta Med

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Biosynthetic approach to combine the first steps of cardenolide formation in Saccharomyces cerevisiae

et al. 2019

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A yeast expression plasmid was constructed containing a cardenolide biosynthetic module, referred to as CARD II, using the AssemblX toolkit, which enables the assembly of large DNA constructs. The genes cloned into the vector were (a) a Δ5‐3β‐hydroxysteroid dehydrogenase gene from Digitalis lanata, (b) a steroid Δ5‐isomerase gene from Comamonas testosteronii, (c) a mutated steroid‐5β‐reductase gene from Arabidopsis thaliana, and (d) a steroid 21‐hydroxylase gene from Mus musculus. A second plasmid bearing an ADR/ADX fusion gene from Bos taurus was also constructed. A Saccharomyces cerevisiae strain bearing these two plasmids was generated. This strain, termed “CARD II yeast”, was capable of producing 5β‐pregnane‐3β,21‐diol‐20‐one, a central intermediate in 5β‐cardenolide biosynthesis, starting from pregnenolone which was added to the culture medium. Using this approach, five consecutive steps in cardenolide biosynthesis were realized in baker's yeast.

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Biosynthesis of Triterpenoid Natural Products

Gao

Yao

2020

Comprehensive Natural Products III

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Spontaneous butenolide ring formation of pregnane-21-O-malonyl hemiesters under mild reaction conditions is facilitated by the 14β-hydroxy group present in all natural cardenolides

Cited by 4 publications

References 14 publications

The Foxgloves (Digitalis) Revisited

The Foxgloves (Digitalis) Revisited

Biosynthetic approach to combine the first steps of cardenolide formation in Saccharomyces cerevisiae

Biosynthesis of Triterpenoid Natural Products

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