Rapid conversion of spirostans into furostan skeletons at room temperature

Viñas-Bravo, Omar; Martínez-Pascual, Roxana; Vega-Báez, José Luis; Gómez-Calvario, Víctor; Sandoval‐Ramírez, Jesús; Montiel‐Smith, Sara; Meza‐Reyes, Socorro; Rosas, Alejandra López-De; Martínez-Montiel, Mónica; Reyes, Mayra; Ruiz, José

doi:10.1016/j.steroids.2011.10.004

Cited by 11 publications

(6 citation statements)

References 47 publications

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“…Double-peak absorption of steroid saponins A and B in the contention-curve were observed after the single dose administration of TSSN, while the other three compounds showed single peak absorption. This might be due to their different molecular structures in F ring [26]. A and B are furostanol saponin type because of F ring cleavage, whereas other three are spirostanol saponin forms with closed F ring.…”

Section: Resultsmentioning

confidence: 99%

Simultaneous quantification of five steroid saponins from Dioscorea zingiberensis C.H. Wright in rat plasma by HPLC–MS/MS and its application to the pharmacokinetic studies

Zhang

Ito

et al. 2015

Steroids

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A simple, reliable and sensitive high-performance liquid chromatography tandem mass spectrometry method (HPLC-MS/MS) was established for simultaneous analyses of the following 5 steroid saponins in rat plasma after the single dose administration of total steroid saponins extracted from the rhizome of Dioscorea zingiberensis C.H.Wright for the first time. Protodioscin, huangjiangsu A, zingiberensis new saponin, dioscin, and gracillin were quantified using ginsenoside Rb1 as the internal standard (IS). The plasma samples were pretreated by a single step acetonitrile-mediated protein precipitation. The chromatographic separation was performed on an Inersil ODS-3 C18 column (250 mm × 4.6 mm, 5 μm) with the mobile phase composed of acetonitrile and water containing 0.1% formic acid under a gradient elution mode at 0.2 mL min−1 using a microsplit after the eluent from the HPLC apparatus. The quantification was accomplished on a triple quadrupole tandem mass spectrometer using the multiple reaction monitoring (MRM) in the positive ionization mode. The above five analytes were stable under sample storage and preparation conditions applied in the present study. The linearity, precision, accuracy, and recoveries of the analysis confirmed the requirements for quality-control purposes. After validation, this proposed method was successfully adopted to investigate the pharmacokinetic parameters of these five analytes.

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Section: Resultsmentioning

confidence: 99%

Simultaneous quantification of five steroid saponins from Dioscorea zingiberensis C.H. Wright in rat plasma by HPLC–MS/MS and its application to the pharmacokinetic studies

Zhang

Ito

et al. 2015

Steroids

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“…1). A correlation peak between 22-OMe and H-16 (4.96 ppm, 1H, m, H-16) was consistent with 22D-OMe stereochemistry in the aglycon [12].…”

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confidence: 62%

Protodioscin in Dioscorea deltoidea Suspension Cell Culture

et al. 2016

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“…Subsequently, changing the basic conditions to t -BuONa/BuOH afforded the non-fused pyrimidine steroids 3a – c in 56–68% yield. Otherwise, for the synthesis of fused pyrimidine steroids 7a – c , commercially available diosgenin 4 was transformed into the pseudosapogenin 5 through a selective F ring cleavage [16]. Then, the oxidative rupture of the intermediate 5 afforded the α,β-unsaturated ketone 6 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Pyrimidine Steroids as Antiproliferative Agents

et al. 2019

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A small and focused library of steroidal non-fused and fused pyrimidines was prepared from pregnenolone acetate and diosgenin, respectively. The key step was the cycloaddition reaction of nitrogen-containing 1,3-binucleophiles with the steroidal α,β-unsaturated ketone. Urea, thiourea and guanidine reacted in a similar manner and afforded the steroidal pyrimidines in good yields. The antiproliferative tests against human tumor cell lines gave GI50 values in the micromolar range and had no effect on healthy fibroblasts. Additional experiments indicated that the compounds did not act as P-glycoprotein substrates, thus avoiding the rise of drug resistance. The fused steroidal pyrimidinethione was selected as drug lead for further testing due to its strong antiproliferative activities within the low micromolar range.

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Rapid conversion of spirostans into furostan skeletons at room temperature

Cited by 11 publications

References 47 publications

Simultaneous quantification of five steroid saponins from Dioscorea zingiberensis C.H. Wright in rat plasma by HPLC–MS/MS and its application to the pharmacokinetic studies

Simultaneous quantification of five steroid saponins from Dioscorea zingiberensis C.H. Wright in rat plasma by HPLC–MS/MS and its application to the pharmacokinetic studies

Protodioscin in Dioscorea deltoidea Suspension Cell Culture

Synthesis and Evaluation of Pyrimidine Steroids as Antiproliferative Agents

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