Chemistry & Biodiversity
December 1, 2016
Felix Krengel, Josefina Herrera Santoyo, Teresa de Jesús Olivera Flores et al.
19 citations
Ten monoterpenoid indole alkaloids and one simple indole alkaloid were identified for the first time in Tabernaemontana alba and Tabernaemontana arborea, two Mexican medicinal plants. The anti-addiction compounds ibogaine and voacangine were found in most wild and greenhouse-grown whole plants, with highest concentrations in stem and root barks. Whole plants of T. alba were regenerated from leaf callus via somatic embryogenesis, but no alkaloids were detected in the callus itself. The species are potentially viable sources of ibogaine and voacangine, and approaches to increase alkaloid yields in plants and cell cultures are discussed.
Chemistry & Biodiversity
July 1, 2019
Felix Krengel, Marco V Mijangos, Marisol Reyes-Lezama et al.
17 citations
Methanol effectively extracts the antiaddictive alkaloids coronaridine, ibogamine, voacangine, and ibogaine (the CIVI-complex) from the root barks of Mexican Tabernaemontana alba and Tabernaemontana arborea. A one-step demethoxycarbonylation process then converts coronaridine and voacangine directly into ibogamine and ibogaine, simplifying the mixture from four to two major compounds. This protocol improves qualitative and quantitative analysis and offers a viable method for bulk production of these therapeutically important substances from these promising plant sources.
Chemistry & Biodiversity
May 1, 2009
Daniel Trachsel, David E. Nichols, Stephanie Kidd et al.
15 citations
A series of novel 2-phenylethylamine compounds with a 4'-aryl substituent was synthesized and tested for binding affinity at the serotonin 5-HT(2A) receptor. Most compounds acted as antagonists with generally low affinity, except for a few with substituents at the 4''-position. The 4''-butyl, 4''-phenyl, and 4'-naphthyl derivatives showed relatively high affinity, with K(i) values of 32, 33, and 41 nM, respectively, indicating tolerance for bulky groups at this location. The 4'-aryl moiety was introduced via a palladium-catalyzed Suzuki reaction.
Chemistry & Biodiversity
April 1, 2019
Felix Krengel, Quentin Chevalier, Jonathan Dickinson et al.
10 citations
Ibogaine and related ibogan alkaloids, which show anti-addictive effects against drugs of abuse, occur in several Apocynaceae species. This work used gas chromatography-mass spectrometry and principal component analysis to compare alkaloid profiles of root and stem barks from four Mexican Tabernaemontana species with the root bark of the African shrub Tabernanthe iboga. Separation between species was attributed to quantitative differences in the major alkaloids coronaridine, ibogamine, voacangine, and ibogaine. T. iboga contained high concentrations of ibogaine, while Tabernaemontana samples showed predominance of either voacangine and ibogaine, or coronaridine and ibogamine. The results confirm that Mexican Tabernaemontana species are viable sources of anti-addictive compounds.
Chemistry & Biodiversity
September 26, 2022
Albert Katchborian‐neto, Mário F. C. Santos, Diego Fernandes Vilas Boas et al.
9 citations
Ayahuasca, a psychoactive beverage made from Banisteriopsis caapi and Psychotria viridis, showed moderate activity against Trypanosoma cruzi trypomastigotes in vitro (IC50 95.78 μg/mL), compared to the reference drug benznidazole (IC50 2.03 μg/mL). The β-carboline alkaloid harmine, isolated from B. caapi, was active (IC50 6.37 μg/mL), while the tryptamine DMT from P. viridis was moderately active (IC50 21.02 μg/mL). In vivo, harmine alone reduced parasitemia in a dose-responsive manner (10 and 100 mg/kg) without toxic effects. Ayahuasca and the harmine-DMT combination worsened parasitemia, suggesting immune modulation via increased IgG and IgG1 antibodies. Molecular docking indicated harmine binds to trypanothione reductase, a promising drug target absent in humans. The findings support ayahuasca's potential against Chagas disease and internal parasites.
Chemistry & Biodiversity
May 1, 2020
Felix Krengel, Jonathan Dickinson, Christopher Jenks et al.
7 citations
Gas chromatography-mass spectrometry (GC/MS) compared the alkaloid profiles of bark and leaf from one Mexican species (Tabernaemontana arborea) and one African species (T. crassa) with the primary commercial sources of semisynthetic ibogaine, Voacanga africana root and stem bark. The qualitative and quantitative similarities between T. arborea and V. africana barks support previous reports that T. arborea is a promising alternative source of voacangine and ibogaine. The results also suggest that T. crassa could be used to produce conopharyngine and ibogaline, two compounds with the same basic skeletal structure and possibly similar antiaddictive properties as ibogaine.
Chemistry & Biodiversity
September 23, 2025
Nathália Andrezza Carvalho de Souza, Pedro Guilherme Sousa de Sá, Tarcísio Cícero de Lima Araújo et al.
2 citations
The chemical composition of Mimosa tenuiflora (Jurema-preta), a plant used in traditional medicine, varies with seasons. Over two years of bimonthly collections in northeastern Brazil, phenolic compounds (especially flavonoids) increased with water stress, radiation, and temperature. Production of the psychoactive compound N,N-dimethyltryptamine (DMT) decreased with higher radiation and temperature but was unaffected by rainfall. Total alkaloids and overall yield showed little connection to climate. These findings highlight the importance of considering season when harvesting the plant for pharmacological use.
Chemistry & Biodiversity
July 1, 2007
Yiqiang Li, Stephen M. Husbands, Mary F Mahon et al.
Salvinorin A, the active component of Salvia divinorum, is a potent kappa-opioid receptor agonist. Computer modeling suggested that splendidin from Salvia splendens and related compounds might have similar activity. However, none of the tested compounds showed significant binding to mu-, delta-, or kappa-opioid receptors, disproving that hypothesis. Two novel compounds were obtained semi-synthetically from salvifarin isolated from Salvia farinacea. The X-ray crystal structure of salvifaricin was determined for the first time and used to elucidate absolute configurations of new products. The relatively accessible diterpenoid salvifaricin could serve as starting material for future structure-activity relationship studies at the kappa-opioid receptor.