Journal of natural products
December 1, 2006
Osamu Shirota, Kumi Nagamatsu, Setsuko Sekita
68 citations
Seven previously unknown neo-clerodane diterpenes—salvidivins A–D, salvinorins H and I, and divinatorin F—along with eight known compounds, were isolated from the hallucinogenic plant Salvia divinorum. Chemical structures of the new compounds were determined using two-dimensional nuclear magnetic resonance spectroscopy. These findings expand the known chemical diversity of this plant, which is of interest for its psychoactive properties.
Journal of natural products
January 1, 2006
Wayne W Harding, Matthew Schmidt, Kevin Tidgewell et al.
59 citations
Salvinorin A, a hallucinogen from the plant Salvia divinorum, is unique as the first non-nitrogenous compound known to bind to opioid receptors. To understand why it selectively targets kappa opioid receptors, researchers systematically altered its structure and tested the effects on receptor binding and activity. This work describes chemical transformations of salvinorin A, including a semisynthesis of salvinicins A and B. It also identifies compound 10a as the first neoclerodane diterpene with delta opioid antagonist activity, providing new tools for studying opioid receptor interactions.
Journal of natural products
April 25, 2011
Anthony Lozama, Christopher W Cunningham, Michael J Caspers et al.
40 citations
New chemical methods using microwave heating enabled the first successful Diels-Alder cycloaddition reactions on the furan ring of salvinorin A, a neoclerodane diterpene natural product. This approach introduced electron-withdrawing groups and bulky aromatic rings at the C-12 position. Some of the resulting cycloadducts, specifically dimethyl- and diethylcarboxylate analogues, retained affinity and selectivity for kappa opioid receptors and acted as full agonists. However, converting these cycloadducts into planar phenyl ring systems reduced their receptor affinity. The work provides a novel strategy for rapidly exploring structure-activity relationships of furan-containing natural products.
Journal of natural products
April 23, 2010
Lukasz M Kutrzeba, Xing-Cong Li, Yuanqing Ding et al.
23 citations
Fresh Salvia divinorum leaves yielded salvinorins E and D, which may be natural precursors to salvinorin A, a potent hallucinogen. During HPLC purification, salvinorin E spontaneously converted into a mixture with its regioisomer salvinorin D in a 3:5 ratio, observable by NMR. This isomerization occurs through a dynamic intramolecular transacetylation process.
Journal of natural products
September 27, 2013
Madan Kumar Paudel, Osamu Shirota, Kaori Sasaki-Tabata et al.
21 citations
A monoclonal antibody was created that recognizes salvinorin A, the main psychoactive compound in Salvia divinorum, and an indirect competitive enzyme-linked immunosorbent assay (icELISA) was developed to detect salvinorins. The assay's calibration range was 0.0195-0.625 μg/mL. Tests on plants from the mint family, including S. divinorum, showed the method is simple, precise, accurate, sensitive, and reliable for identifying the plant.
Journal of natural products
August 27, 2021
Camilla B Chan, Christian B M Poulie, Simon S Wismann et al.
13 citations
The term 'false peyote' is commonly applied to Lophophora diffusa, but several other unrelated cacti also share this name due to their resemblance to true peyote (Lophophora williamsii) or similar habitats. Over 40 alkaloids have been isolated from the Lophophora genus, yet only mescaline's pharmacological effects are well-studied. The major alkaloid in L. diffusa is pellotine, a tetrahydroisoquinoline briefly marketed as a sleeping aid in the early 1900s based on reports of its hypnotic properties. Pharmacological experiments on these alkaloids occurred around 1900, with chemical synthesis achieved decades later and biosynthetic pathways reported in the late 1960s. This review outlines the relationship of false peyotes to L. williamsii regarding alkaloid content, synthesis, and pharmacology.
Journal of natural products
June 23, 2023
Bruno González, Nicolás Veiga, Gonzalo Hernández et al.
7 citations
The iboga alkaloids, such as ibogaine and voacangine, are promising scaffolds for developing drugs to treat neuropsychiatric disorders. This work examines how these molecules react under oxidation with dioxygen, peroxo compounds, and iodine. The C16-carboxymethyl ester group in voacangine makes the molecule more stable toward oxidation than ibogaine, particularly in the indole ring, where 7-hydroxy- or 7-peroxy-indolenines form. However, the ester increases reactivity at the isoquinuclidinic nitrogen, leading to C3-oxidized products via regioselective iminium formation. Density functional theory calculations explain this differential reactivity. Additionally, NMR experiments and theoretical calculations revise the absolute stereochemistry at C7 in voacangine's 7-hydroxyindolenine to S, correcting earlier reports of R configuration.
Journal of natural products
March 22, 2024
Lucas Apolinário Chibli, Bruna Ribeiro de Lima, Ariadne Magalhães Carneiro et al.
4 citations
Alkaloid extraction traditionally relies on hazardous chemicals like HCl and CH₂Cl₂. This work tested whether that practice is justified by superior recovery. In three laboratories, alkaloids harmine, boldine, vincamine, and mescaline were extracted from four medicinal plants. Replacing HCl with citric acid maintained or improved extraction performance. Ethyl acetate could fully replace CH₂Cl₂ in three of four cases and partially in the fourth without loss. The alternative solvents tert-amyl methyl ether and n-butyl acetate also enhanced alkaloid extraction. These findings suggest natural products laboratories can adopt greener solvents and processes, aligning with current pharmaceutical industry practices.