From Soybean Phytosterols to Steroid Hormones

Wang, Fengqing; Yao, Kang; Wei, Dongzhi

doi:10.5772/18808

Cited by 36 publications

(51 citation statements)

References 81 publications

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“…2 Despite major advances in the total synthesis of steroids, most steroid-based drugs are obtained by semi-synthesis using feedstock isolated from plant or animal sources. 3 Recent developments in the field of asymmetric catalysis have enabled the efficient preparation of simple enantioenriched steroids such as estrones. 4 However, fewer asymmetric catalytic strategies for the construction of more complex steroids are available.…”

Section: Introductionmentioning

confidence: 99%

Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions

et al. 2015

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A new scalable enantioselective approach to functionalized oxygenated steroids is described. This strategy is based on chiral bis(oxazoline) copper(II) complex-catalyzed enantioselective and diastereoselective Michael reactions of cyclic ketoesters and enones to install vicinal quaternary and tertiary stereocenters. In addition, the utility of copper(II) salts as highly active catalysts for the Michael reactions of traditionally unreactive ββ′-enones and substituted ββ′-ketoesters that results in unprecedented Michael adducts containing vicinal all-carbon quaternary centers is also demonstrated. The Michael adducts subsequently undergo base-promoted diastereoselective aldol cascade reactions resulting in the natural or unnatural steroid skeletons. The experimental and computational studies suggest that the torsional strain effects arising from the presence of the Δ5-unsaturation are key controling elements for the formation of the natural cardenolide scaffold. The described method enables expedient generation of polycyclic molecules including modified steroidal scaffolds as well as challenging-to-synthesize Hajos-Parrish and Wieland-Miescher ketones.

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Section: Introductionmentioning

confidence: 99%

Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions

et al. 2015

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“…After isolation of the first mutant of Mycobacterium sp. which performed degradation of sterols to AD, a number of mutants were described and patented [11,46]. These mutants were obtained by chemical or physicochemical mutagenesis of the native strains performing effective degradation of sterols.…”

Section: Production Of Optically Active Compoundsmentioning

confidence: 99%

“…Currently, conventional mutagenesis based on random mutations induced by UV/chemical treatments is more and more frequently replaced by targeted disruption of genes encoding either Ksh or KstD to generate highly selective strains [50,53]. Genetic manipulation is potentially able to overcome a problem, significant for industrial applications, connected with the fact that most of the mutant strains in practical use produce AD and ADD simultaneously [46]. A mutant of Mycobacterium neoaurum NwIB-01 after inactivation of the KstD-encoding gene produced mainly AD (AD:ADD 11:1).…”

Section: Production Of Optically Active Compoundsmentioning

confidence: 99%

“…In view of the fact that currently only the location of genes directly responsible for sterol catabolism is known in Rhodococcus and Mycobacterium , but usually not the function of the encoded proteins [51], the literature suggests that the immediate tasks are characterization of the mechanisms of phytosterol catabolism, phytosterol uptake, tolerance to toxic products, and global regulations involved in the sterol metabolism [46]. This might not be easy using known microorganisms of good performance, because the metabolic processes are complicated and interlaced.…”

Section: Production Of Optically Active Compoundsmentioning

confidence: 99%

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Biotransformations Utilizing β-Oxidation Cycle Reactions in the Synthesis of Natural Compounds and Medicines

Œwizdor

Panek

Milecka-Tronina

et al. 2012

IJMS

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β-Oxidation cycle reactions, which are key stages in the metabolism of fatty acids in eucaryotic cells and in processes with a significant role in the degradation of acids used by microbes as a carbon source, have also found application in biotransformations. One of the major advantages of biotransformations based on the β-oxidation cycle is the possibility to transform a substrate in a series of reactions catalyzed by a number of enzymes. It allows the use of sterols as a substrate base in the production of natural steroid compounds and their analogues. This route also leads to biologically active compounds of therapeutic significance. Transformations of natural substrates via β-oxidation are the core part of the synthetic routes of natural flavors used as food additives. Stereoselectivity of the enzymes catalyzing the stages of dehydrogenation and addition of a water molecule to the double bond also finds application in the synthesis of chiral biologically active compounds, including medicines. Recent advances in genetic, metabolic engineering, methods for the enhancement of bioprocess productivity and the selectivity of target reactions are also described.

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“…Moreover, they did not study the actual influence of digestion of contaminated feed on cattle or, in this case, horses. [12] The conversion of phytosterols to steroids has been reported in other biological systems, [15] mainly involving a variety of microorganisms [16] such as Mycobacterium sp., [17][18][19] Arthrobacter, and Nocardia sp. [20] In addition, a number of studies have been devoted to the ability of invertebrate organisms to convert phytosterols into anabolic steroids: maggots of Lucilia Serica, [21] Crustaceae, [22] and zebra fish.…”

Section: Introductionmentioning

confidence: 99%

Mouldy feed: A possible explanation for the excretion of anabolic‐androgenic steroids in horses

Decloedt

Bailly-Chouriberry²,

Bussche

et al. 2016

Drug Testing and Analysis

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To ensure fair competition and to protect the horse's welfare, horses have to compete on their own merits, without any unfair advantage that might follow the use of drugs. Therefore, regulatory authorities list all substances that are not allowed in competition, including most anabolic-androgenic steroids. As zero-tolerance is retained, the question arose whether the consumption of mouldy feed could lead to the excretion of steroids, due to the biotransformation of plant phytosterols to steroids. A rapid ultra high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) analytical method, previously validated according to AORC (Association of Official Racing Chemists) and EC (European Commission) guidelines, was used to measure steroids in different sample types. Multiple mouldy feed samples were tested for the presence of steroids. The effect of digestion was tested by in vitro simulation of the horse's hindgut in batch incubations. In most feed samples no steroids were detected, even when the products were mouldy. Mouldy corn however showed to contain up to 3.0 ± 0.4 μg/kg AED (4-androstenedione), the main testosterone precursor. This concentration increased when mouldy corn (with added phytosterols) was digested in vitro. An herbal phytosupplement also showed to contain α-testosterone. These results demonstrate that it is important to caution against the consumption of any feed or (herbal) supplement of which the detailed ingredients and quantitative analysis are unknown. The consumption of mouldy corn should especially be avoided, not only from a horse health and welfare point of view, but also to avoid possible inadvertent positive doping results.

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From Soybean Phytosterols to Steroid Hormones

Cited by 36 publications

References 81 publications

Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions

Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions

Biotransformations Utilizing β-Oxidation Cycle Reactions in the Synthesis of Natural Compounds and Medicines

Mouldy feed: A possible explanation for the excretion of anabolic‐androgenic steroids in horses

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