Journal of Natural ProductsFebruary 28, 2025Zachary Stryker, Jorge I Castillo-Arellano, Stephen J Cutler et al.
Cannabidiol (CBD) is a natural product associated with a wide range of biological and therapeutic activities. Despite the widespread cultural acceptance of CBD as a medicinal agent, much remains to be determined regarding its precise mechanism(s) of action in treating multiple conditions. CBD has been shown to promiscuously interact with several neurological targets with varying affinities. To...
Journal of Natural ProductsMarch 22, 2024Lucas 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...
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...
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...
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...
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,...
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...
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...
Ten new indole alkaloids (1-10) comprising five ibogan, two aspidosperman, one vincamine, and two bisindole alkaloids, in addition to 32 known alkaloids, were isolated from the stem-bark extract of a Malayan Tabernaemontana corymbosa. The structures of these alkaloids were determined based on analysis of the NMR and MS data and, in five instances (1, 3, 5, 6, 8), confirmed by X-ray diffraction...
Seven new iboga-type alkaloids, ervaoffines A-D (1-4), (7S)-3-oxoibogaine hydroxyindolenine (5), ibogaine-5,6-dione (6), and 19-epi-5-oxovoacristine (7), and 10 known alkaloids were isolated from Ervatamia officinalis. The absolute configurations of 1-7 were determined through X-ray diffraction and electronic circular dichroism (ECD) analyses. Ervaoffines A and B represent the first iboga-type...
Journal of Natural ProductsMarch 28, 2014Marcos Marçal Ferreira Queiroz, Emerson Ferreira Queiroz, Maria Luiza Zeraik et al.
The secondary metabolite content of Tetrapterys mucronata, a poorly studied plant that is used occasionally in Brazil for the preparation of a psychotropic plant decoction called "Ayahuasca", was determined to establish its chemical composition and to search for acetylcholinesterase (AChE) inhibitors. The ethanolic extract of the bark of T. mucronata exhibited in vitro AChE inhibition in a TLC...
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...
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...
A search for biosynthetic precursors of salvinorin A (1) led to the isolation of a new neoclerodane diterpenoid hemiacetal mixture, salvinorins J (2), from the chloroform extract of Salvia divinorum. A leaf surface extraction method was used on S. divinorum, affording a chlorophyll-free extract containing predominantly neoclerodane diterpenoids, including the new salvinorins J (2) and 14 known...
Brominated indole alkaloids are a common class of metabolites reported from sponges of the order Verongida. Herein we report the isolation, structure determination, and activity of metabolites from three Florida sponges, namely, Verongula rigida (order Verongida, family Aplysinidae), Smenospongia aurea, and S. cerebriformis (order Dictyoceratida, family Thorectidae). All three species were...
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...
Several neoclerodanes, such as salvinorin A (1) and herkinorin (3), have recently been shown to possess opioid receptor activity in vitro and in vivo. To explore the structure-affinity relationships of this interesting class of compounds, we have synthesized a series of analogues from 1 isolated from Salvia divinorum. Here, we report the semisynthesis of neoclerodane diterpenes and their...
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...
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.
Three new neoclerodane diterpenoids, salvinorins D-F (4-6), have been isolated from the leaves of Salvia divinorum. The structures were elucidated by chemical and spectroscopic methods, particularly 1D and 2D NMR. A simplified isolation method using chromatography on activated carbon also gave improved yields of the controlled substance salvinorin A (1) and of salvinorin C (3).
The stem bark of the Panamanian plant Stemmademia obovata has afforded a new ibogaine-type alkaloid, obovamine ( 1 ), whose structure was determined by a combination of spectral interpretation and chemical correlations. Ten known alkaloids, coronaridine, coronaridine hydroxyindolenine, voacangine, voacangine hydroxyindolenine, (19 S )-heyneanine, (19 S )-heyneanine hydroxyindolenine, (19 S...
The whole plant of Ervatamia coronaria var. plena obtained from Thailand has afforded a new indole alkaloid 19S-heyneanine hydroxyindolenine whose structure was deduced through interpretation of spectral data. Nine known alkaloids, coronaridine, coronaridine hydroxyindolenine, voacangine, voacangine hydroxyindolenine, heyneanine, voacristine, 3-oxo-coronaridine, 3-oxo-voacangine,and voacristine...
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...
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...
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...