Literature DB >> 18061225

Selective reactivity of 2-mercaptoethanol with 5beta,6beta-epoxide in steroids from Withania somnifera.

Laxminarain Misra1, Payare Lal, Narayan D Chaurasia, Rajender S Sangwan, Sudhir Sinha, Rakesh Tuli.   

Abstract

2-Mercaptoethanol reacts selectively with the 5beta,6beta-epoxy steroids isolated from Withania somnifera substituting the epoxide by a six-membered oxyethylene-2'-thio ring whereas it failed to show such reactivity on 6alpha,7alpha-epoxy withasteroids. The structure of the product has been elucidated by spectroscopic methods, especially applying extensive 2D NMR methods. The anticancer activity of withaferin A was lost in the reaction product indicating that its activity is also linked to the free 5beta,6beta-epoxide functional group.

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Year:  2007        PMID: 18061225     DOI: 10.1016/j.steroids.2007.10.006

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


  8 in total

1.  Chemistry of withaferin-A: chemo, regio, and stereoselective synthesis of novel spiro-pyrrolizidino-oxindole adducts of withaferin-A via one-pot three-component [3+2] azomethine ylide cycloaddition and their cytotoxicity evaluation.

Authors:  Yogesh P Bharitkar; Satish Kanhar; Neradibilli Suneel; Susanta Kumar Mondal; Abhijit Hazra; Nirup B Mondal
Journal:  Mol Divers       Date:  2015-03-08       Impact factor: 2.943

2.  Structure-activity relationship (SAR) of withanolides to inhibit Hsp90 for its activity in pancreatic cancer cells.

Authors:  Mancang Gu; Yanke Yu; G M Kamal B Gunaherath; A A Leslie Gunatilaka; Dapeng Li; Duxin Sun
Journal:  Invest New Drugs       Date:  2013-07-26       Impact factor: 3.850

3.  Differential chemosensitization of P-glycoprotein overexpressing K562/Adr cells by withaferin A and Siamois polyphenols.

Authors:  Wipob Suttana; Samlee Mankhetkorn; Wilart Poompimon; Ajay Palagani; Sergey Zhokhov; Sarah Gerlo; Guy Haegeman; Wim Vanden Berghe
Journal:  Mol Cancer       Date:  2010-05-03       Impact factor: 27.401

Review 4.  Treatment of adult and pediatric high-grade gliomas with Withaferin A: antitumor mechanisms and future perspectives.

Authors:  Megan M Marlow; Sumedh S Shah; Eduardo A Véliz; Michael E Ivan; Regina M Graham
Journal:  J Nat Med       Date:  2016-07-02       Impact factor: 2.343

Review 5.  Recent Advances in the Chemistry and Therapeutic Evaluation of Naturally Occurring and Synthetic Withanolides.

Authors:  Amandeep Singh; Asif Raza; Shantu Amin; Chendil Damodaran; Arun K Sharma
Journal:  Molecules       Date:  2022-01-28       Impact factor: 4.411

6.  Withania somnifera Extracts Promote Resilience against Age-Related and Stress-Induced Behavioral Phenotypes in Drosophila melanogaster; a Possible Role of Other Compounds besides Withanolides.

Authors:  Helen Holvoet; Dani M Long; Alexander Law; Christine McClure; Jaewoo Choi; Liping Yang; Luke Marney; Burkhard Poeck; Roland Strauss; Jan F Stevens; Claudia S Maier; Amala Soumyanath; Doris Kretzschmar
Journal:  Nutrients       Date:  2022-09-22       Impact factor: 6.706

7.  Aromatase and glycosyl transferase inhibiting acridone alkaloids from fruits of Cameroonian Zanthoxylum species.

Authors:  Vyry Na Wouatsa; Laxminarain Misra; Shiv Kumar; Om Prakash; Feroz Khan; Francois Tchoumbougnang; R Kumar Venkatesh
Journal:  Chem Cent J       Date:  2013-07-18       Impact factor: 4.215

8.  Transcription factor repertoire in Ashwagandha (Withania somnifera) through analytics of transcriptomic resources: Insights into regulation of development and withanolide metabolism.

Authors:  Sandhya Tripathi; Rajender Singh Sangwan; Lokesh Kumar Narnoliya; Yashdeep Srivastava; Bhawana Mishra; Neelam Singh Sangwan
Journal:  Sci Rep       Date:  2017-11-30       Impact factor: 4.379

  8 in total

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