Journal of Natural Products
March 22, 2024
Lucas Apolinário Chibli, Bruna Ribeiro de Lima, Ariadne Magalhães Carneiro et al.
4 citations
The fact that alkaloids are bases has been the most explored chemical feature of their extraction and purification procedures. The main drawback of these procedures is that they employ undesirable chemicals, with HCl and CH2Cl2 probably being the most commonly employed chemicals in their subsequent steps. This work tested the hypothesis that advantages in recovery efficiency support this common...
Journal of Natural Products
June 23, 2023
Bruno González, Nicolás Veiga, Gonzalo Hernández et al.
7 citations
The iboga alkaloids scaffold shows great potential as a pharmacophore in drug candidates for the treatment of neuropsychiatric disorders. Thus, the study of the reactivity of this type of motif is particularly useful for the generation of new analogs suitable for medicinal chemistry goals. In this article, we analyzed the oxidation pattern of ibogaine and voacangine using dioxygen, peroxo...
Journal of Natural Products
August 27, 2021
Camilla B Chan, Christian B M Poulie, Simon S Wismann et al.
13 citations
Commonly, false peyote refers to Lophophora diffusa. However, several other unrelated cacti go by this colloquial name. They either resemble "true" peyote, Lophophora williamsii, or are found in similar habitats. To date, over 40 different alkaloids have been isolated from the Lophophora genus. Of these, only the pharmacological actions of mescaline (1) have been extensively investigated. The...
Journal of Natural Products
March 5, 2021
Janis Fricke, Alexander M. Sherwood, Adam L. Halberstadt et al.
18 citations
A novel analogue of psilocybin was produced by hybrid chemoenzymatic synthesis in sufficient quantity to enable bioassay. Utilizing purified 4-hydroxytryptamine kinase from Psilocybe cubensis, chemically synthesized 5-methylpsilocin (2) was enzymatically phosphorylated to provide 5-methylpsilocybin (1). The zwitterionic product was isolated from the enzymatic step with high purity utilizing a...
Journal of Natural Products
February 20, 2020
Alexander M. Sherwood, Adam L. Halberstadt, Adam K. Klein et al.
79 citations
A general synthetic method was developed to access known tryptamine natural products present in psilocybin-producing mushrooms. In vitro and in vivo experiments were then conducted to inform speculations on the psychoactive properties, or lack thereof, of the natural products. In animal models, psychedelic activity by baeocystin alone was not evident using the mouse head twitch response assay,...
Journal of Natural Products
September 20, 2017
Claudius Lenz, Jonas Wick, Dirk Hoffmeister
62 citations
We report the identification of ω-N-methyl-4-hydroxytryptamine (norpsilocin, 1) from the carpophores of the hallucinogenic mushroom Psilocybe cubensis. The structure was elucidated by 1D and 2D NMR spectroscopy and high-resolution mass spectrometry. Norpsilocin has not previously been reported as a natural product. It likely represents the actual psychotropic agent liberated from its...
Journal of Natural Products
July 28, 2017
Anil Yilmaz, Rachel Saylor Crowley, Alexander M. Sherwood et al.
Columbin (1) is a furanolactone diterpene isolated from the roots of Jateorhiza and Tinospora species. These species generally grow in Asia and Africa and have been used in folk medicine for their apparent analgesic and antipyretic activities. Columbin (1) is of particular interest due to its structural similarity to the known kappa-opioid receptor (KOR) agonist salvinorin A. Given that the KOR...
Journal of Natural Products
April 25, 2011
Anthony Lozama, Christopher W Cunningham, Michael J Caspers et al.
40 citations
As part of our continuing efforts toward more fully understanding the structure-activity relationships of the neoclerodane diterpene salvinorin A, we report the synthesis and biological characterization of unique cycloadducts through [4+2] Diels-Alder cycloaddition. Microwave-assisted methods were developed and successfully employed, aiding in functionalizing the chemically sensitive salvinorin...
Journal of Natural Products
April 23, 2010
Lukasz Kutrzeba, Xing-Cong Li, Yuanqing Ding et al.
23 citations
Extraction of fresh Salvia divinorum leaves afforded salvinorins E and D as potential biosynthesis precursors of salvinorin A, a major metabolite and a potent hallucinogen. Attempts at HPLC purification of salvinorin E (2) with acetonitrile as a solvent revealed an equilibrium with its regioisomer, salvinorin D (3), in a 3:5 ratio. The presence of both compounds was readily observed in the (1)H...
Journal of Natural Products
December 1, 2006
Osamu Shirota, Kumi Nagamatsu, Setsuko Sekita
68 citations
Seven new neo-clerodane diterpenes, salvidivins A (2), B, (3), C (4), and D (5), salvinorins H (6) and I (7), and divinatorin [corrected] F (8), along with eight known neo-clerodane diterpenes, salvinorins A (1)-F, divinatorins A and B, and seven other constituents, were isolated from the hallucinogenic sage Salvia divinorum. The structures of 1-7 were elucidated on the basis of 2D NMR...
Journal of Natural Products
2006
Wayne W Harding, Matthew Schmidt, Kevin Tidgewell et al.
59 citations
Salvinorin A (1) is a hallucinogenic neoclerodane diterpene isolated from the widely available psychoactive plant Salvia divinorum and is the first example of a non-nitrogenous opioid receptor ligand. At present, there is little information available as to why this compound is selective for kappa opioid receptors. One approach to better understanding the mode of binding of 1 at kappa receptors...
Journal of Natural Products
May 30, 2003
Osamu Shirota, Wataru Hakamata, Yukihiro Goda
90 citations
The concise large-scale syntheses of psilocin (1) and psilocybin (2), the principal hallucinogenic constituents of "magic mushroom", were achieved without chromatographic purification. The key step in the synthesis of 2 was the isolation of the dibenzyl-protected intermediate (7) as a zwitterionic derivative (8), which was completely identified by means of 2D NMR analyses.
Journal of Natural Products
July 1, 1987
E. Ohenoja, J. Jokiranta, T. Mäkinen et al.
21 citations
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Occurrence of Psilocybin and Psilocin in Finnish FungiE. Ohenoja, J. Jokiranta, T. Mäkinen, A. Kaikkonen, and M. M. AiraksinenCite this: J. Nat. Prod. 1987, 50, 4, 741–744Publication Date (Print):July 1, 1987Publication History Published online1 July 2004Published inissue 1 July...
Journal of Natural Products
July 1, 1986
W.-w. Ma, Xiaomo Jiang, R. Graham Cooks et al.
10 citations
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCactus Alkaloids, LXI. Identification of Mescaline and Related Compounds in Eight Additional Species Using Tlc and Ms/msW. W. Ma, X. Y. Jiang, R. G. Cooks, J. L. McLaughlin, A. C. Gibson, F. Zeylemaker, and C. N. OstolazaCite this: J. Nat. Prod. 1986, 49, 4, 735–737Publication Date (Print):July 1, 1986Publication History Published online1 July...
Journal of Natural Products
March 1, 1982
Sunibhond Pummangura, Jerry L. Mclaughlin, R. C. Schifferdecker
10 citations
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCactus Alkaloids. LI. Lack of Mescaline Translocation in Grafted TrichocereusS. Pummangura, J. L. McLaughlin, and R. C. SchifferdeckerCite this: J. Nat. Prod. 1982, 45, 2, 224–225Publication Date (Print):March 1, 1982Publication History Published online1 July 2004Published inissue 1 March...
Journal of Natural Products
May 1, 1981
Yutaka Koike, Kohko Wada, Genjiro Kusano et al.
45 citations
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIsolation of Psilocybin From Psilocybe argentipes and Its Determination in Specimens of Some MushroomsYutaka Koike, Kohko Wada, Genjiro Kusano, Shigeo Nozoe, and Kazumasa YokoyamaCite this: J. Nat. Prod. 1981, 44, 3, 362–365Publication Date (Print):May 1, 1981Publication History Published online1 July 2004Published inissue 1 May...