Literature DB >> 20936100

Novel neoclerodane diterpene derivatives from the smoke of salvinorin A.

Zhongze Ma1, Gang Deng, David Y W Lee.   

Abstract

Salvinorin A is a naturally-occurring potent and selective kappa opioid receptor agonist, and smoking salvinorin A produces the most intense hallucinogenic effects in human. Eight neoclerodane diterpene derivatives were isolated from the smoke of salvinorin A, and their structures were identified by spectroscopic methods. The major structural changes include epimerizations, eliminations, and rearrangements.

Entities:  

Year:  2010        PMID: 20936100      PMCID: PMC2950941          DOI: 10.1016/j.tetlet.2010.07.144

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  14 in total

Review 1.  Salvinorin A: the "magic mint" hallucinogen finds a molecular target in the kappa opioid receptor.

Authors:  Douglas J Sheffler; Bryan L Roth
Journal:  Trends Pharmacol Sci       Date:  2003-03       Impact factor: 14.819

2.  Pattern of use and subjective effects of Salvia divinorum among recreational users.

Authors:  Débora González; Jordi Riba; José Carlos Bouso; Gregorio Gómez-Jarabo; Manel J Barbanoj
Journal:  Drug Alcohol Depend       Date:  2006-05-23       Impact factor: 4.492

3.  Synthesis and in vitro evaluation of salvinorin A analogues: effect of configuration at C(2) and substitution at C(18).

Authors:  Cécile Béguin; Michele R Richards; Jian-Guo Li; Yulin Wang; Wei Xu; Lee-Yuan Liu-Chen; William A Carlezon; Bruce M Cohen
Journal:  Bioorg Med Chem Lett       Date:  2006-06-13       Impact factor: 2.823

4.  Synthetic studies of neoclerodane diterpenes from Salvia divinorum: semisynthesis of salvinicins A and B and other chemical transformations of salvinorin A.

Authors:  Wayne W Harding; Matthew Schmidt; Kevin Tidgewell; Pavitra Kannan; Kenneth G Holden; Brian Gilmour; Hernan Navarro; Richard B Rothman; Thomas E Prisinzano
Journal:  J Nat Prod       Date:  2006-01       Impact factor: 4.050

5.  Salvinicins A and B, new neoclerodane diterpenes from Salvia divinorum.

Authors:  Wayne W Harding; Kevin Tidgewell; Matthew Schmidt; Kushal Shah; Christina M Dersch; John Snyder; Damon Parrish; Jeffrey R Deschamps; Richard B Rothman; Thomas E Prisinzano
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

6.  Revised structure of deacetyl-1,10-didehydrosalvinorin G.

Authors:  Zhongze Ma; David Y W Lee
Journal:  Tetrahedron Lett       Date:  2007-07-30       Impact factor: 2.415

7.  A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A.

Authors:  Kevin Tidgewell; Wayne W Harding; Mark Schmidt; Kenneth G Holden; Daryl J Murry; Thomas E Prisinzano
Journal:  Bioorg Med Chem Lett       Date:  2004-10-18       Impact factor: 2.823

8.  Synthesis of deacetyl-1,10-didehydrosalvinorin G.

Authors:  Zhongze Ma; David Y W Lee
Journal:  Tetrahedron Lett       Date:  2008-03-10       Impact factor: 2.415

Review 9.  Natural products as tools for neuroscience: discovery and development of novel agents to treat drug abuse.

Authors:  Thomas E Prisinzano
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

10.  Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist.

Authors:  Bryan L Roth; Karen Baner; Richard Westkaemper; Daniel Siebert; Kenner C Rice; SeAnna Steinberg; Paul Ernsberger; Richard B Rothman
Journal:  Proc Natl Acad Sci U S A       Date:  2002-08-21       Impact factor: 11.205

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  4 in total

Review 1.  Clerodane diterpenes: sources, structures, and biological activities.

Authors:  Rongtao Li; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  Nat Prod Rep       Date:  2016-07-18       Impact factor: 13.423

Review 2.  Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A.

Authors:  Christopher W Cunningham; Richard B Rothman; Thomas E Prisinzano
Journal:  Pharmacol Rev       Date:  2011-03-28       Impact factor: 25.468

Review 3.  A review of salvinorin analogs and their kappa-opioid receptor activity.

Authors:  Jeremy J Roach; Ryan A Shenvi
Journal:  Bioorg Med Chem Lett       Date:  2018-03-12       Impact factor: 2.823

4.  Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum.

Authors:  Andrew P Riley; Victor W Day; Hernán A Navarro; Thomas E Prisinzano
Journal:  Org Lett       Date:  2013-11-18       Impact factor: 6.005

  4 in total

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