MOESM5 of Facile synthesis of Îą-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Additional file 5. Specimen NMR Spectra of alkoxymethyltriphenylphosphonium iodides

MOESM1 of Facile synthesis of Îą-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Additional file 1. General method for synthesis of Bis-alkoxy methanes

MOESM3 of Facile synthesis of Îą-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Additional file 3. Asymmetric reduction of acetophenone

MOESM6 of Facile synthesis of Îą-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Additional file 6. Specimen NMR Spectrum of vinyl ether

MOESM4 of Facile synthesis of Îą-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Additional file 4. Crystallography data for(S)-sec-Butoxymethyltriphenylphosphonium iodide

<i>In-vitro</i> protein anti-glycation activity of different drugs.

<p><i>In-vitro</i> protein anti-glycation activity of different drugs.</p

New Anti-Inflammatory Metabolites by Microbial Transformation of Medrysone

<div><p>Microbial transformation of the anti-inflammatory steroid medrysone (<b>1</b>) was carried out for the first time with the filamentous fungi <i>Cunninghamella blakesleeana</i> (ATCC 8688a), <i>Neurospora crassa</i> (ATCC 18419), and <i>Rhizopus stolonifer</i> (TSY 0471). The objective was to evaluate the anti-inflammatory potential of the substrate (<b>1</b>) and its metabolites. This yielded seven new metabolites, 14α-hydroxy-6α-methylpregn-4-ene-3,11,20-trione (<b>2</b>), 6β-hydroxy-6α-methylpregn-4-ene-3,11,20-trione (<b>3</b>), 15β-hydroxy-6α-methylpregn-4-ene-3,11,20-trione (<b>4</b>), 6β,17α-dihydroxy-6α-methylpregn-4-ene-3,11,20-trione (<b>5</b>), 6β,20<i>S</i>-dihydroxy-6α-methylpregn-4-ene-3,11-dione (<b>6</b>), 11β,16β-dihydroxy-6α-methylpregn-4-ene-3,11-dione (<b>7</b>), and 15β,20<i>R</i>-dihydroxy-6α-methylpregn-4-ene-3,11-dione (<b>8</b>). Single-crystal X-ray diffraction technique unambiguously established the structures of the metabolites <b>2</b>, <b>4</b>, <b>6</b>, and <b>8</b>. Fungal transformation of <b>1</b> yielded oxidation at the C-6β, -11β, -14α, -15β, -16β positions. Various cellular anti-inflammatory assays, including inhibition of phagocyte oxidative burst, T-cell proliferation, and cytokine were performed. Among all the tested compounds, metabolite <b>6</b> (IC₅₀ <b>=</b> 30.3 μg/mL) moderately inhibited the reactive oxygen species (ROS) produced from zymosan-induced human whole blood cells. Compounds <b>1</b>, <b>4</b>, <b>5</b>, <b>7</b>, and <b>8</b> strongly inhibited the proliferation of T-cells with IC₅₀ values between <0.2–10.4 μg/mL. Compound <b>7</b> was found to be the most potent inhibitor (IC₅₀ < 0.2 μg/mL), whereas compounds <b>2</b>, <b>3</b>, and <b>6</b> showed moderate levels of inhibition (IC₅₀ = 14.6–20.0 μg/mL). Compounds <b>1</b>, and <b>7</b> also inhibited the production of pro-inflammatory cytokine TNF-α. All these compounds were found to be non-toxic to 3T3 cells (mouse fibroblast), and also showed no activity when tested against HeLa (human epithelial carcinoma), or against PC3 (prostate cancer) cancer cell lines.</p></div

¹H-NMR chemical shift data of compounds 1–8 (δ in ppm, <i>J</i> in Hz).

<p>¹H-NMR chemical shift data of compounds 1–8 (δ in ppm, <i>J</i> in Hz).</p

Biotransformation of medrysone (1) with <i>Cunninghamella blakesleeana</i>.

<p>Biotransformation of medrysone (1) with <i>Cunninghamella blakesleeana</i>.</p

Effect of compounds 1–8 on PHA activated T-cells proliferation.

<p>Effect of compounds 1–8 on PHA activated T-cells proliferation.</p