Preparation of steroidal hormones with an emphasis on transformations of phytosterols and cholesterol - a review

Jasem, Yosef Al; Khan, Mubashar; Taha, Ahmed; Thiemann, Thies

doi:10.13171/mjc.3.2.2014.18.04.15

Cited by 32 publications

(16 citation statements)

References 44 publications

(81 reference statements)

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“…This steroid is of high industrial importance and has been subject of interest to many researchers worldwide over the years. In fact, most of the therapeutically useful steroidal drugs, including sex hormones and corticosteroids, are produced in a semisynthetic fashion from natural precursors and predominantly from diosgenin [9, 10]. However, in addition to this high synthetic relevance, diosgenin itself has several important biological activities also with great interest for the pharmaceutical industry [5, 7, 11].…”

Section: Introductionmentioning

confidence: 99%

Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology

Jesus

Martins

Gallardo

et al. 2016

Journal of Analytical Methods in Chemistry

197

125

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Diosgenin, a steroidal sapogenin, occurs abundantly in plants such as Dioscorea alata, Smilax China, and Trigonella foenum graecum. This bioactive phytochemical not only is used as an important starting material for the preparation of several steroidal drugs in the pharmaceutical industry, but has revealed also high potential and interest in the treatment of various types of disorders such as cancer, hypercholesterolemia, inflammation, and several types of infections. Due to its pharmacological and industrial importance, several extraction and analytical procedures have been developed and applied over the years to isolate, detect, and quantify diosgenin, not only in its natural sources and pharmaceutical compositions, but also in animal matrices for pharmacodynamic, pharmacokinetic, and toxicological studies. Within these, HPLC technique coupled to different detectors is the most commonly analytical procedure described for this compound. However, other alternative methods were also published. Thus, the present review aims to provide collective information on the most recent pharmacological data on diosgenin and on the most relevant analytical techniques used to isolate, detect, and quantify this compound as well.

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Section: Introductionmentioning

confidence: 99%

Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology

Jesus

Martins

Gallardo

et al. 2016

Journal of Analytical Methods in Chemistry

197

125

View full text Add to dashboard Cite

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“…[7][8][9] The structure of ergosterol allows its use in microbial conversions to produce similar intermediates as are formed from phytosterols and cholesterol. [10] Although ergosterol is a possible precursor for steroids, [11] fractionation of abundant residual yeast biomass from industrial side-streams to ergosterol and other products has not been studied to a great extent.…”

Section: Introductionmentioning

confidence: 99%

Fractionation process for the protective isolation of ergosterol and trehalose from microbial biomass

Pastinen

Nyyssölä

Pihlajaniemi

et al. 2017

Process Biochemistry

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A new process is described for the two phase extraction of ergosterol and trehalose from microbial biomass. Baker's yeast was used as a model organism to develop the method, which was then applied for extracting 13 oleaginous microbes. Major findings of the study were that the ergosterol content was not dependent on intracellular oil content and that 1-butanol and alkaline pH were needed to protect ergosterol. Saponification for 3−4 hours at 85−100 ºC followed by extraction of the reaction mixture with toluene gave the maximal ergosterol yield.Trehalose was stable at this temperature and remained in water solution, but the maximal yield was obtained after a shorter reaction time at lower alkalinity. Although trehalose alone is stable at alkaline pH, extraction yields of trehalose from yeast decreased with increasing alkalinity.This finding led us to propose a two-step process in which trehalose is separated in the first step and ergosterol in the second. The possibility to apply this method to fractionate oleaginous microbes in process scale is discussed from technical viewpoints.

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“…Synthetic anabolic-androgenic steroids are produced mainly by a combination of microbial and chemical processes on phytosterols and sapogenins, C3-plant derived natural precursors. 14 Phytosterols are collected as residual products during soybean-oil production: stigmasterol, β-sitosterol, campesterol, and brassicasterol are the most typical ones. 15,16 Sapogenins, such as hecogenin, tiogenin, and diosgenin, are primarily extracted from roots of various Dioscorea species of Mexico yams.…”

Section: Introductionmentioning

confidence: 99%

Carbon isotopic characterization of prednisolone and prednisone pharmaceutical formulations: Implications in antidoping analysis

Iannella

Botrè

Colamonici

et al. 2020

Drug Testing and Analysis

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Twenty‐two pharmaceutical formulations containing prednisolone or prednisone commercially available in Italy, Belgium, Spain, Brazil, and India were analyzed through a specific gas chromatography combustion isotope ratio mass spectrometry (GC‐C‐IRMS) method. All of them showed typical non‐endogenous δ13C values, except for the Belgian nasal spray, Sofrasolone®, with a less depleted 13C content (−17.84 ± 0.18‰). Observational studies were performed on two volunteers in therapy with Sofrasolone® to confirm the applicability of the method and to suggest adequate interpretation criteria also in the case of drugs with less negative δ13C values. Urine samples were collected before, during, and within the 36 hours after the administration of the spray. Both δ13C values and urinary concentrations of prednisolone and prednisone were evaluated. All samples were subjected to an adequate pre‐treatment (enzymatic hydrolysis, liquid/liquid extraction, and two sequential HPLC steps) before injection to the GC‐C‐IRMS instrument, according to the method recently developed and validated in our laboratory. Pregnanediol (PD), tetrahydro‐11‐deoxycortisol (THS), and pregnanetriol (PT) were selected as endogenous reference compounds (ERC). The excretion profile was estimated through liquid chromatography coupled to tandem mass spectrometry (LC–MS/MS) method used routinely for the quali‐quantitative detection of glucocorticoids. δ13C values and urinary levels of prednisolone and prednisone were also determined after the intake of one single vial of Sintredius®, a prednisolone oral formulation with a conventional more negative δ13C value (−29.28 ± 0.25‰). Finally, the potential masking effect that combined therapy with Sofrasolone® and Sintredius® could induce on the IRMS findings was investigated.

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Preparation of steroidal hormones with an emphasis on transformations of phytosterols and cholesterol - a review

Cited by 32 publications

References 44 publications

Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology

Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology

Fractionation process for the protective isolation of ergosterol and trehalose from microbial biomass

Carbon isotopic characterization of prednisolone and prednisone pharmaceutical formulations: Implications in antidoping analysis

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