Gram-scale chromatographic purification of β-sitosterolSynthesis and characterization of β-sitosterol oxides

Zhang, Xin; Geoffroy, Philippe; Miesch, Michel; Julien-David, Diane; Raul, Françis; Aoudé-Werner, Dalal; Marchioni, Eric

doi:10.1016/j.steroids.2005.06.003

Cited by 86 publications

(44 citation statements)

References 24 publications

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“…The structures of isolated compounds were established by one-and two-dimensional NMR experiments and compared with those in literature (Seebacher et al, 2003;Zhang et al, 2005;Muzitano et al, 2006;Faini et al, 2007); IR, UV, and high-resolution mass spectrometry were also in agreement with the proposed structures. NMR experiments were performed in a…”

Section: Methodssupporting

confidence: 62%

Isolation of Modulators of the Liver-Specific Organic Anion-Transporting Polypeptides (OATPs) 1B1 and 1B3 from Rollinia emarginata Schlecht (Annonaceae)

Roth¹,

Araya²,

Timmermann³

et al. 2011

J Pharmacol Exp Ther

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Organic anion-transporting polypeptides 1B1 and 1B3 (OATP1B1 and OATP1B3) are liver-specific transporters that mediate the uptake of a broad range of drugs into hepatocytes, including statins, antibiotics, and many anticancer drugs. Compounds that alter transport by one or both of these OATPs could potentially be used to target drugs to hepatocytes or improve the bioavailability of drugs that are cleared by the liver. In this study, we applied a bioassay-guided isolation approach to identify such compounds from the organic extract of Rollinia emarginata Schlecht (Annonaceae). Fractions of the plant extract were screened for effects on OATP1B1-and OATP1B3-mediated transport of the model substrates estradiol-17␤-glucuronide and estrone-3-sulfate. We isolated three compounds, ursolic acid, oleanolic acid, and 8-transp-coumaroyloxy-␣-terpineol, which inhibited estradiol-17␤-glucuronide uptake by OATP1B1 but not OATP1B3. In addition, a rare compound, quercetin 3-O-␣-L-arabinopyranosyl(132) ␣-Lrhamnopyranoside, was identified that had distinct effects on each OATP. OATP1B1 was strongly inhibited, as was OATP1B3-mediated transport of estradiol-17␤-glucuronide. However, OATP1B3-mediated uptake of estrone-3-sulfate was stimulated 4-to 5-fold. Kinetic analysis of this stimulation revealed that the apparent affinity for estrone-3-sulfate was increased (decreased K m ), whereas the maximal rate of transport (V max ) was significantly reduced. These results demonstrate a mechanism through which the hepatic uptake of drug OATP substrates could be stimulated.

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Section: Methodssupporting

confidence: 62%

Isolation of Modulators of the Liver-Specific Organic Anion-Transporting Polypeptides (OATPs) 1B1 and 1B3 from Rollinia emarginata Schlecht (Annonaceae)

Roth¹,

Araya²,

Timmermann³

et al. 2011

J Pharmacol Exp Ther

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“…Therefore, compound 3 was established as 2,16-dihydroxyl-15-keto-2-acetoxy-ent-pimar-8(14)-ene-16-O-β-D-glucopyranoside. The known compounds sitost-5-en-3β-ol acetate (4) [12], β-sitosterol-3-O-β-D-glucopyranoside (5) [13], 3,5,6-trihydroxysitostane (6) [14], stigmastane-3β,5α,6β-triol-3,6-diacetate (7) [15] were identified by comparison of their spectroscopic data with the literature values.…”

Section: Resultsmentioning

confidence: 99%

Norditerpenoids from Flickingeria fimbriata and Their Inhibitory Activities on Nitric Oxide and Tumor Necrosis Factor-α Production in Mouse Macrophages

Chen

Zhong

et al. 2014

Molecules

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Bioassay-guided fractionation of the ethanolic extract of the leaves of Flickingeria flimbriata led to the isolation of two new degraded diterpenoids 1 and 2, a new ent-pimarane type diterpenoid 3, and four known steroids 4-7. The structures of 1-3 were elucidated by spectroscopic analysis, and their absolute configurations were determined by chemical methods, TDDFT quantum chemical calculations of ECD spectra, and CD exiton chirality method. Compounds 1 and 2, named flickinflimilins A and B, possess a rare 15,16-dinor-ent-pimarane skeleton. Compounds 1-7 were screened for the inhibitory activity against lipopolysaccharide (LPS)-induced NO and TNF-α production in RAW264.7 cells. Compounds 1-3 exhibited potent inhibitory activities, with IC 50 values of less than 10 µM.

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“…Recently the first reports of the synthesis of reference samples of β-sitosterol and its oxides, and their biological evaluation, have appeared from our group (10,11). This was followed by a later report on the purification of β-sitosterol by column chromatography and the synthesis of its oxidation products (12).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Stigmasterol Oxidation Products

Foley¹,

O’Callaghan²,

O’Brien³

et al. 2010

J. Agric. Food Chem.

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The synthesis and structural characterization of a series of oxides of stigmasterol is described providing a valuable series of reference standards for these oxides, analogous to the cholesterol oxidation products (COPs) which have been shown to have detrimental biological effects. Biological evaluation of the oxides of phytosterols is significant in the context of increased dietary use of phytosterols in the drive to reduce cholesterol absorption.

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Gram-scale chromatographic purification of β-sitosterolSynthesis and characterization of β-sitosterol oxides

Cited by 86 publications

References 24 publications

Isolation of Modulators of the Liver-Specific Organic Anion-Transporting Polypeptides (OATPs) 1B1 and 1B3 from Rollinia emarginata Schlecht (Annonaceae)

Isolation of Modulators of the Liver-Specific Organic Anion-Transporting Polypeptides (OATPs) 1B1 and 1B3 from Rollinia emarginata Schlecht (Annonaceae)

Norditerpenoids from Flickingeria fimbriata and Their Inhibitory Activities on Nitric Oxide and Tumor Necrosis Factor-α Production in Mouse Macrophages

Synthesis and Characterization of Stigmasterol Oxidation Products

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