Literature DB >> 20685279

A concise synthesis of beta-sitosterol and other phytosterols.

Jiliang Hang1, Patrick Dussault.   

Abstract

A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of beta-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Delta(22-23) phytosterols. Copyright 2010 Elsevier Inc. All rights reserved.

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Year:  2010        PMID： 20685279      PMCID： PMC2950316          DOI： 10.1016/j.steroids.2010.05.016

Source DB:  PubMed          Journal:  Steroids        ISSN： 0039-128X            Impact factor:   2.668


  14 in total

Review 1.  Pharmacological properties of plant sterols in vivo and in vitro observations.

Authors:  M H Moghadasian
Journal:  Life Sci       Date:  2000-06-30       Impact factor: 5.037

2.  Sitosterol-containing lipoproteins trigger free sterol-induced caspase-independent death in ACAT-competent macrophages.

Authors:  Liping Bao; Yankun Li; Shi-Xian Deng; Donald Landry; Ira Tabas
Journal:  J Biol Chem       Date:  2006-08-24       Impact factor: 5.157

3.  Synthesis, isolation and characterisation of beta-sitosterol and beta-sitosterol oxide derivatives.

Authors:  Florence O McCarthy; Jay Chopra; Alan Ford; Sean A Hogan; Joe P Kerry; Nora M O'Brien; Eileen Ryan; Anita R Maguire
Journal:  Org Biomol Chem       Date:  2005-07-13       Impact factor: 3.876

4.  Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide.

Authors:  Shao-Min Wang; Yan-Bing Zhang; Hong-Min Liu; Guo-Bin Yu; Ke-Rang Wang
Journal:  Steroids       Date:  2006-12-27       Impact factor: 2.668

5.  [3,3]-Claisen rearrangements in 24alpha-methyl steroid synthesis. Application to campesterol, crinosterol, and Delta25-crinosterol side chain construction.

Authors:  Vladimir A Khripach; Vladimir N Zhabinskii; Olga V Konstantinova; Natalya B Khripach; Andrey P Antonchick; Bernd Schneider
Journal:  Steroids       Date:  2002-06       Impact factor: 2.668

6.  Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids.

Authors:  Vladimir A Khripach; Vladimir N Zhabinskii; Olga V Konstantinova; Natalya B Khripach; Alexey V Antonchick; Andrey P Antonchick; Bernd Schneider
Journal:  Steroids       Date:  2005-03-26       Impact factor: 2.668

Review 7.  Dietary phytosterols: a review of metabolism, benefits and side effects.

Authors:  W H Ling; P J Jones
Journal:  Life Sci       Date:  1995       Impact factor: 5.037

8.  The effects of pomegranate seed extract and beta-sitosterol on rat uterine contractions.

Authors:  Wilawan Promprom; Pakanit Kupittayanant; Korakod Indrapichate; Susan Wray; Sajeera Kupittayanant
Journal:  Reprod Sci       Date:  2009-12-04       Impact factor: 3.060

9.  Identification of crinosterol from astigamatid mites.

Authors:  Kenjiro Murakami; Bunta Watanabe; Ritsuo Nishida; Naoki Mori; Yasumasa Kuwahara
Journal:  Insect Biochem Mol Biol       Date:  2007-03-03       Impact factor: 4.714

10.  Plant sterol and stanol substrate specificity of pancreatic cholesterol esterase.

Authors:  Andrew W Brown; Jiliang Hang; Patrick H Dussault; Timothy P Carr
Journal:  J Nutr Biochem       Date:  2009-07-16       Impact factor: 6.048
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  5 in total

1.  Rapid purification of gram quantities of β-sitosterol from a commercial phytosterol mixture.

Authors:  Narayanan Srividya; Deanna Brooke Heidorn; Bernd Markus Lange
Journal:  BMC Res Notes       Date:  2014-03-27

Review 2.  Critical Analysis on Characterization, Systemic Effect, and Therapeutic Potential of Beta-Sitosterol: A Plant-Derived Orphan Phytosterol.

Authors:  Muhammad Shahdaat Bin Sayeed; Selim Muhammad Rezaul Karim; Tasnuva Sharmin; Mohammed Monzur Morshed
Journal:  Medicines (Basel)       Date:  2016-11-15

3.  Structure elucidation of β-sitosterol with antibacterial activity from the root bark of Malva parviflora.

Authors:  Mesfin Medihin Ododo; Manash Kumar Choudhury; Ahmed Hussen Dekebo
Journal:  Springerplus       Date:  2016-07-29

4.  Development of Methods to Quantify Free and Conjugated Steroids in Fatty Matrices by HPLC-MS/MS.

Authors:  Kelly da S Bezerra; Nelson R Antoniosi Filho
Journal:  ACS Omega       Date:  2020-05-22

5.  Characterization and evaluation of mycosterol secreted from endophytic strain of Gymnema sylvestre for inhibition of α-glucosidase activity.

Authors:  Amit Ranjan; Rajesh Kumar Singh; Saumya Khare; Ruchita Tripathi; Rajesh Kumar Pandey; Anurag Kumar Singh; Vibhav Gautam; Jyoti Shankar Tripathi; Santosh Kumar Singh
Journal:  Sci Rep       Date:  2019-11-21       Impact factor: 4.379
  5 in total

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