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Literature DB >> 15987194

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

Wayne W Harding¹, Kevin Tidgewell, Matthew Schmidt, Kushal Shah, Christina M Dersch, John Snyder, Damon Parrish, Jeffrey R Deschamps, Richard B Rothman, Thomas E Prisinzano.

Abstract

[reaction: see text] Two new neoclerodane diterpenes, salvinicins A (4) and B (5), were isolated from the dried leaves of Salvia divinorum. The structures of these compounds were elucidated by spectroscopic techniques, including (1)H and (13)C NMR, NOESY, HMQC, and HMBC. The absolute stereochemistry of these compounds was assigned on the basis of single-crystal X-ray crystallographic analysis of salvinicin A (4) and a 3,4-dichlorobenzoate derivative of salvinorin B.

Entities: Chemical Species

Mesh：

Substances：

Year: 2005 PMID： 15987194 PMCID： PMC2535573 DOI： 10.1021/ol0510522

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

20 in total

1. Agonist activity of LSD and lisuride at cloned 5HT2A and 5HT2C receptors.

Authors: C T Egan; K Herrick-Davis; K Miller; R A Glennon; M Teitler
Journal: Psychopharmacology (Berl) Date: 1998-04 Impact factor: 4.530

2. Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist.

Authors: Thomas A Munro; Mark A Rizzacasa; Bryan L Roth; Beth A Toth; Feng Yan
Journal: J Med Chem Date: 2005-01-27 Impact factor: 7.446

3. Determination of Salvinorin A in body fluids by high performance liquid chromatography-atmospheric pressure chemical ionization.

Authors: Mark S Schmidt; Thomas E Prisinzano; Kevin Tidgewell; Wayne Harding; Eduardo R Butelman; Mary J Kreek; Daryl J Murry
Journal: J Chromatogr B Analyt Technol Biomed Life Sci Date: 2005-04-25 Impact factor: 3.205

4. Salvia divinorum: an hallucinogenic mint which might become a new recreational drug in Switzerland.

Authors: C Giroud; F Felber; M Augsburger; B Horisberger; L Rivier; P Mangin
Journal: Forensic Sci Int Date: 2000-08-14 Impact factor: 2.395

5. 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

6. Comparison of pharmacological activities of three distinct kappa ligands (Salvinorin A, TRK-820 and 3FLB) on kappa opioid receptors in vitro and their antipruritic and antinociceptive activities in vivo.

Authors: Yulin Wang; Kang Tang; Saadet Inan; Daniel Siebert; Ulrike Holzgrabe; David Y W Lee; Peng Huang; Jian-Guo Li; Alan Cowan; Lee-Yuan Liu-Chen
Journal: J Pharmacol Exp Ther Date: 2004-09-21 Impact factor: 4.030

Review 7. Salvia divinorum and the unique diterpene hallucinogen, Salvinorin (divinorin) A.

Authors: L J Valdés
Journal: J Psychoactive Drugs Date: 1994 Jul-Sep

8. Evidence for 5-HT2 involvement in the mechanism of action of hallucinogenic agents.

Authors: R A Glennon; M Titeler; J D McKenney
Journal: Life Sci Date: 1984-12-17 Impact factor: 5.037

9. Radioligand binding evidence implicates the brain 5-HT2 receptor as a site of action for LSD and phenylisopropylamine hallucinogens.

Authors: M Titeler; R A Lyon; R A Glennon
Journal: Psychopharmacology (Berl) Date: 1988 Impact factor: 4.530

10. Salvia divinorum and salvinorin A: new pharmacologic findings.

Authors: D J Siebert
Journal: J Ethnopharmacol Date: 1994-06 Impact factor: 4.360

18 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. Salvinorin A analogs as probes in opioid pharmacology.

Authors: Thomas E Prisinzano; Richard B Rothman
Journal: Chem Rev Date: 2008-05 Impact factor: 60.622

3. Autoxidation of salvinorin A under basic conditions.

Authors: Thomas A Munro; Glenn W Goetchius; Bryan L Roth; Timothy A Vortherms; Mark A Rizzacasa
Journal: J Org Chem Date: 2005-11-25 Impact factor: 4.354

Review 4. Neoclerodanes as atypical opioid receptor ligands.

Authors: Thomas E Prisinzano
Journal: J Med Chem Date: 2013-04-18 Impact factor: 7.446

Review 5. 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

6. The C-2 derivatives of salvinorin A, ethoxymethyl ether Sal B and β-tetrahydropyran Sal B, have anti-cocaine properties with minimal side effects.

Authors: Amy W M Ewald; Peter J Bosch; Aimee Culverhouse; Rachel Saylor Crowley; Benjamin Neuenswander; Thomas E Prisinzano; Bronwyn M Kivell
Journal: Psychopharmacology (Berl) Date: 2017-05-23 Impact factor: 4.530

7. Herkinorin analogues with differential beta-arrestin-2 interactions.

Authors: Kevin Tidgewell; Chad E Groer; Wayne W Harding; Anthony Lozama; Matthew Schmidt; Alfred Marquam; Jessica Hiemstra; John S Partilla; Christina M Dersch; Richard B Rothman; Laura M Bohn; Thomas E Prisinzano
Journal: J Med Chem Date: 2008-04-02 Impact factor: 7.446