Coprostan 3 ol

Manufactured by Merck Group

Coprostan-3-ol is a laboratory reagent used for various analytical and research purposes. It is a steroidal compound that serves as a standard or reference material in analytical procedures.

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5 protocols using coprostan 3 ol

Virus Entry Assay Protocol

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HOS cells expressing CD4/CCR5 were acquired from the NIH AIDS Reagent Program from Dr. Nathaniel Landau. DNA sequences encoding BaL.01 Env and NL4-3 R⁻ E⁻ Luc⁺ core were also obtained from the NIH AIDS Reagent Program from Dr. John Mascola and Dr. Nathaniel Landau, respectively. The plasmid encoding JR-FL gp160 was a kind gift of Dr. Simon Cocklin, while the plasmid encoding YU2 gp160 was a kind gift of Drs. Alon Herschorn and Joseph Sodroski. Methyl β-cyclodextrin (MβCD), cholesterol, cholestanol (5α-cholestan-3β-ol), 7-dehydrocholesterol (3β-hydroxy-5,7-cholestadiene), coprostan-3-ol (5β-cholestan-3β-ol), cholestenone (3-oxo-4-cholestene), 5α-cholestane, dehydroergosterol (Ergosta-5,7,9(11),22-tetraen-3β-ol) and Triton X-100 were purchased from Sigma–Aldrich. Laurdan dye was purchased from Invitrogen. Rabbit and mouse anti-p24 and CD45 antibodies were purchased from Abcam. D7324 anti-gp120 antibody was purchased from Aalto.

Sundaram R.V., Li H., Bailey L., Rashad A.A., Aneja R., Weiss K., Huynh J., Bastian A.R., Papazoglou E., Abrams C., Wrenn S, & Chaiken I. (2016). Impact of HIV-1 Membrane Cholesterol on Cell-Independent Lytic Inactivation and Cellular Infectivity. Biochemistry, 55(3), 447-458.

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Quantification of Triterpene Alcohols

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Coprostan-3-ol, ethyl acetate and pyridine were purchased from Sigma-Aldrich. n-Hexane was obtained from Merck, N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA) from Thermo Scientific, and potassium hydroxide pellets from Scientific Laboratory Supplies. β-Amyrin, erythrodiol and oleanolic acid standards were purchased from Extrasynthese.

Dale M.P., Moses T., Johnston E.J, & Rosser S.J. (2020). A systematic comparison of triterpenoid biosynthetic enzymes for the production of oleanolic acid in Saccharomyces cerevisiae. PLoS ONE, 15(5), e0231980.

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Synthesis and Purification of Bile Acids and Steroids

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Chenodeoxycholic acid (1), ursodeoxycholic acid (5), hyodeoxycholic acid (8), hyocholic acid (9), coprostan-3-ol (12), trans-dehydroandrosterone (15), progesterone (17), 11α-hydroprogesterone (18), α-estradiol (19), and diosgenin (22) were purchased from Sigma-Aldrich. Cholic acid (2), lithocholic acid (3), deoxycholic acid (4), cholesterol (11), testosterone (13), and oestron (20) were purchased from Fluka. Dehydrocholic acid (10) and hydrocortisone (21) were purchased from Janssen Chimica and BDH Chemicals, respectively. Glyco (6) and tauroursodeoxycholic acid (7) were prepared as previously reported¹⁴ (link)^,¹⁵ (link). Purity of tested compounds 1–22 was >95%.

Nocentini A., Bonardi A., Gratteri P., Cerra B., Gioiello A, & Supuran C.T. (2018). Steroids interfere with human carbonic anhydrase activity by using alternative binding mechanisms. Journal of Enzyme Inhibition and Medicinal Chemistry, 33(1), 1453-1459.

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Serum Metabolite Quantification Protocol

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Serum separated by centrifugation (7000 × g, 3 min) using Beckton Dickson vials was stored at −80 °C until analysis. Samples were prepared as previously described by Kelley with slight modifications [17 (link)]. Coprostan-3-ol (20 μg, Sigma) added to each 50 μl sample was the surrogate internal standard. Saponified, extracted and dried samples were derivatized with bis-trimethylsilytrifluoroacetamide plus 1 % trimethylchlorosilane (ThermoFisher) for 1 h (60 °C) and injected onto a Trace 1310GC TSQ 8000 Evo Mass Spectrometer (Thermo Scientific) using a ZB-1701 column (Phenomenex). Retention times were confirmed using standards (Sigma), and the National Institutes of Standards and Technology mass spectral library (data version 14).

London E., Tatsi C., Soldin S.J., Wassif C.A., Backlund P., Ng D., Biesecker L.G, & Stratakis C.A. (2020). Acute Statin Administration Reduces Levels of Steroid Hormone Precursors. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme, 52(10), 742-746.

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Combinatorial Biosynthesis of Plant Metabolites

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Five-week-old plants were infiltrated using three leaves per plant as replicates. For each combination, four A. tumefaciens strains were coinfiltrated including two carrying tHMGR and Sad1 along with two strains carrying the relevant CYP genes (where a single CYP was used, GFP was included in place of the second CYP). Leaves were harvested 5 days after infiltration and lyophilized. For extraction, a single 15 mm leaf disk was taken from each dried leaf and 500 μL EtOAc [containing 10 μg/mL coprostan-3-ol (Sigma-Aldrich)] added to each sample. Leaf tissue was disrupted by shaking with a single 3 mm tungsten carbide bead (Qiagen). Samples were incubated at room temperature with gentle shaking for 2 h. Aliquots (50 μL) were taken from each sample, transferred to a separate vial and dried under N₂. GC-MS analysis was performed as described in section 3.5 and samples analyzed using Agilent MassHunter Qualitative Analysis software. New products were identified by overlaying the total ion chromatograms of the combinatorial samples with their relevant single CYP controls (see Fig. S4-S13). A summary of the combinatorial biosynthesis results is provided in Table S1.

Reed J., Stephenson M.J., Miettinen K., Brouwer B., Leveau A., Brett P., Goss R.J., Goossens A., O’Connell M.A, & Osbourn A. (2017). A translational synthetic biology platform for rapid access to gram-scale quantities of novel drug-like molecules. Metabolic Engineering, 42, 185-193.

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