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Zorana Oreščanin-Dušić, Nikola Tatalović, Teodora Vidonja-Uzelac, Jelena Nestorov, Aleksandra Nikolić-Kokić, Ana Mijušković, Mihajlo Spasić, Roman Paškulin, Mara Bresjanac, Duško Blagojević
Ibogaine is an indole alkaloid originally extracted from the root bark of the African rainforest shrub Tabernanthe iboga . It has been explored as a treatment for substance abuse because it interrupts drug addiction and relieves withdrawal symptoms. However, it has been shown that ibogaine treatment leads to a sharp and transient fall in cellular ATP level followed by an increase of cellular respiration and ROS production. Since contractile tissues are sensitive to changes in the levels of ATP and ROS, here we investigated an ibogaine-mediated link between altered redox homeostasis and uterine contractile activity...
2018: Oxidative Medicine and Cellular Longevity
Yang Qu, Michael E A M Easson, Razvan Simionescu, Josef Hajicek, Antje M K Thamm, Vonny Salim, Vincenzo De Luca
Monoterpenoid indole alkaloids (MIAs) possess a diversity of alkaloid skeletons whose biosynthesis is poorly understood. A bioinformatic search of candidate genes, combined with their virus-induced gene silencing, targeted MIA profiling and in vitro/in vivo pathway reconstitution identified and functionally characterized six genes as well as a seventh enzyme reaction required for the conversion of 19 E -geissoschizine to tabersonine and catharanthine. The involvement of pathway intermediates in the formation of four MIA skeletons is described, and the role of stemmadenine- O -acetylation in providing necessary reactive substrates for the formation of iboga and aspidosperma MIAs is described...
March 20, 2018: Proceedings of the National Academy of Sciences of the United States of America
Yu Zhang, Yu-Xi Yuan, Masuo Goto, Ling-Li Guo, Xiao-Nian Li, Susan L Morris-Natschke, Kuo-Hsiung Lee, Xiao-Jiang Hao
Nineteen vobasinyl-ibogan-type bisindole alkaloids, including nine new compounds, taburnaemines A-I (1-9), were isolated from the twigs and leaves of Tabernaemontana corymbosa. The structures and absolute configurations of the new alkaloids were determined by a combination of MS, NMR, and ECD analyses. Alkaloids 1-5 contain a rare 1,3-oxazinane moiety in the vobasinyl unit, while 6 has an uncommon 1,3-oxazolidine moiety in the iboga unit. The absolute configurations of alkaloid 1 and the known alkaloid tabernaecorymbosine A (10) were confirmed by single-crystal X-ray diffraction analysis...
March 23, 2018: Journal of Natural Products
B Bading Taika, M Bouckandou, A Souza, H P Bourobou Bourobou, L S MacKenzie, L Lione
ETHNOPHARMACOLOGICAL RELEVANCE: The management of diabetes mellitus management in African communities, especially in Gabon, is not well established as more than 60% of population rely on traditional treatments as primary healthcare. The aim of this review was to collect and present the scientific evidence for the use of medicinal plants that are in currect by Gabonese traditional healers to manage diabetes or hyperglycaemia based here on the pharmacological and toxicological profiles of plants with anti-diabetic activity...
April 24, 2018: Journal of Ethnopharmacology
Yang Qu, Antje M K Thamm, Matthew Czerwinski, Sayaka Masada, Kyung Hee Kim, Graham Jones, Ping Liang, Vincenzo De Luca
A Catharanthus roseus mutant accumulates high levels of ajmalicine at the expense of catharanthine and vindoline. The altered chemistry depends on increased expression and biochemical activities of strictosidine β-glucosidase and ajmalicine synthase activities and reduced expression and biochemical activity of geissoschizine synthase. The Madagascar periwinkle [Catharanthus roseus (L.) G. Don] is a commercially important horticultural flower species and is a valuable source for several monoterpenoid indole alkaloids (MIAs), such as the powerful antihypertensive drug ajmalicine and the antineoplastic agents, vinblastine and vincristine...
March 2018: Planta
Christian Leitner, Tanja Gaich
A total synthesis to the pseudoaspidospermidine family via a C-H activation/transannular cyclization strategy has been accomplished. The applicability of this approach is showcased in the concise synthesis (ten steps) of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine (4) starting from literature known compound 11. Via a joint synthetic sequence we were also able to address the related iboga alkaloid (±)-isovelbanamine (7) in nine steps. Key features of this synthesis are a transannular cyclization to generate the pseudoaspidospermidine skeleton (C-H activation) and a Witkop photocyclization reaction providing a 9-membered lactam...
July 4, 2017: Chemical Communications: Chem Comm
Catherine Lavaud, Georges Massiot
Iboga alkaloids are a particular class of indolomonoterpenes most often characterized by an isoquinuclidine nucleus. Their first occurrence was detected in the roots of Tabernanthe iboga, a sacred plant to the people of Gabon, which made it cult object. Ibogaine is the main representative of this class of alkaloids and its psychoactive properties are well documented. It has been proposed as a drug cessation treatment and has a wide range of activities in targeting opioids, cocaine, and alcohol. The purpose of this chapter is to provide a background on this molecule and related compounds and to update knowledge on the most recent advances made...
2017: Progress in the Chemistry of Organic Natural Products
Yang Qu, Razvan Simonescu, Vincenzo De Luca
Two new monoterpene indole alkaloids, isoakuammiline (1) and 18-hydroxypseudovincadifformine (2), and five known alkaloids, coronaridine (3), heyneanine (4), 3,19-oxidocoronaridine (5), tabersonine, and strictosidine, were identified from the fruit of Tabernaemontana litoralis. The structures of the alkaloids were determined using NMR and MS data analyses. While 18-hydroxypseudovincadifformine (2) showed a new hydroxylation pattern, isoakuammiline (1) revealed a novel skeleton for monoterpene indole alkaloids...
December 23, 2016: Journal of Natural Products
Silvia Graziano, Laura Orsolini, Maria Concetta Rotolo, Roberta Tittarelli, Fabrizio Schifano, Simona Pichini
BACKGROUND: A new trend among users of new psychoactive substances' the consumption of "herbal highs": plant parts containing psychoactive substances. Most of the substances extracted from herbs, in old centuries were at the centre of religious ceremonies of ancient civilizations. Currently, these herbal products are mainly sold by internet web sites and easily obtained since some of them have no legal restriction. OBJECTIVE: We reviewed psychoactive effects and neuropharmacology of the most used "herbal highs" with characterized active principles, with studies reporting mechanisms of action, pharmacological and subjective effects, eventual secondary effects including intoxications and/or fatalities Method: The PubMed database was searched using the following key...
2017: Current Neuropharmacology
Choy-Eng Nge, Kae-Shin Sim, Siew-Huah Lim, Noel F Thomas, Yun-Yee Low, Toh-Seok Kam
Examination of the EtOH extract of the Malayan Tabernaemontana corymbosa resulted in the isolation of three new alkaloids, viz., cononuridine (1), an unusual hexacyclic, iboga-derived, monoterpenoid indole characterized by contraction of the tetrahydroazepine C-ring and incorporation of an additional isoxazolidine ring, taberisidine (2), a seco-corynanthean alkaloid, and conofolidine (3), an Aspidosperma-Aspidosperma bisindole that showed pronounced in vitro growth inhibitory activity against an array of human cancer cell lines, including KB, vincristine-resistant KB, PC-3, LNCaP, MCF7, MDA-MB-231, HT-29, and HCT 116 cells...
October 28, 2016: Journal of Natural Products
Zygmunt Zdrojewicz, Bartłomiej Kuszczak, Natalia Olszak
Ibogaine is a natural chemical compound, which belongs to the indole alkaloid family. It can be naturally found within the root bark of african plant Tabernanthe iboga. Ibogaine plays a significant role among tribal cultures. Ibogaine, in small amount, causes reduction of hunger, thirst and exhaustion. In bigger amount, however, it can cause intensive visions. Other effects include reduction or complete disappearance of absitnence symptoms visible in people addicted to the nicotine, alcohol, methamphetamine, cocaine or opioids, what has been scientifically proven after the tests on animals and small groups of people...
July 29, 2016: Polski Merkuriusz Lekarski: Organ Polskiego Towarzystwa Lekarskiego
Angela Paterna, Sofia E Gomes, Pedro M Borralho, Silva Mulhovo, Cecília M P Rodrigues, Maria-José U Ferreira
Phytochemical investigation of the roots of the African medicinal plant Tabernaemontana elegans led to the isolation of three new (1-3) and two known (4 and 5) bisindole alkaloids of the vobasinyl-iboga type. The structures of 1-3 were assigned by spectroscopic methods, mainly using 1D and 2D NMR experiments. All of the isolated compounds were evaluated for their cytotoxicity against HCT116 colon and HepG2 liver carcinoma cells by the MTS metabolism assay. Compounds 1-3 and 5 were found to be cytotoxic to HCT116 colon cancer cells, displaying IC50 values in the range 8...
October 28, 2016: Journal of Natural Products
Angela Paterna, Sofia E Gomes, Pedro M Borralho, Silva Mulhovo, Cecília M P Rodrigues, Maria-José U Ferreira
ETHNOPHARMACOLOGICAL RELEVANCE: Tabernaemontana elegans Stapf. (Apocynaceae) is a medicinal plant traditionally used in African countries to treat cancer. AIMS OF THE STUDY: To discover new apoptosis inducing lead compounds from T. elegans and provide scientific validation of the ethnopharmacological use of this plant. MATERIALS AND METHODS: Through fractionation, (3'R)-hydroxytaberanelegantine C (1), a vobasinyl-iboga bisindole alkaloid, was isolated from a cytotoxic alkaloid fraction of the methanol extract of T...
December 24, 2016: Journal of Ethnopharmacology
L J Schep, R J Slaughter, S Galea, D Newcombe
The indole alkaloid ibogaine, present in the root bark of the West African rain forest shrub Tabernanthe iboga, has been adopted in the West as a treatment for drug dependence. Treatment of patients requires large doses of the alkaloid to cause hallucinations, an alleged integral part of the patient's treatment regime. However, case reports and case series continue to describe evidences of ataxia, gastrointestinal distress, ventricular arrhythmias and sudden and unexplained deaths of patients undergoing treatment for drug dependence...
September 1, 2016: Drug and Alcohol Dependence
Thomas Gicquel, Chloé Hugbart, Françoise Le Devehat, Sylvie Lepage, Alain Baert, Renaud Bouvet, Isabelle Morel
Powdered roots of iboga (Tabernanthe iboga) contain ibogaine, an alkaloid that has been used to treat addictions. We report the case of a 30-year-old woman who died after ingesting a powder labeled as Tabernanthe iboga she had bought online. Analysis of the powder revealed the absence of ibogaine but the presence of toxic alkaloids (ajmaline, yohimbine and reserpine) found in Rauvolfia sp. plant species. An original and specific LC-MS/MS method developed to quantify ajmaline, yohimbine and reserpine showed respective concentrations of 109...
September 2016: Forensic Science International
Laurie Cloutier-Gill, Evan Wood, Trevor Millar, Caroline Ferris, M Eugenia Socias
BACKGROUND: Opioid use disorders (OUD) translate into major health, social, and economic consequences. Opioid agonist medications, which generally require long-term administration, are the mainstay pharmacological treatment of OUD. However, a large proportion of individuals with OUD either refuse or fail to respond to these therapies. Ibogaine, a naturally occurring substance found in the Tabernanthe iboga plant, has shown potential to bring about transformative or spiritual experiences that have reportedly been associated with long-term abstinece...
July 2016: Journal of Psychoactive Drugs
Bridget Forsyth, Liana Machado, Tim Jowett, Hannah Jakobi, Kira Garbe, Helen Winter, Paul Glue
ETHNOPHARMACOLOGICAL RELEVANCE: Root bark from Tabernanthe iboga has been used traditionally in West Africa as a psychoactive substance in religious rituals. In smaller doses it is reported anecdotally to have stimulant properties. AIM OF THE STUDY: To evaluate the influence of a single 20mg ibogaine dose on psychological variables reflecting subjective mood state and a range of cognitive functions. MATERIALS AND METHODS: 21 healthy male volunteers received single 20mg doses of ibogaine after 6 days pretreatment with double-blind paroxetine or placebo...
August 2, 2016: Journal of Ethnopharmacology
Gaoyuan Zhao, Xingang Xie, Haiyu Sun, Ziyun Yuan, Zhuliang Zhong, Shouchu Tang, Xuegong She
We present the application of a bioinspired collective synthesis strategy in the total syntheses of seven iboga-type indole alkaloids: (±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D. In particular, tabertinggine and its congeners serve as iboga precursors for the subsequent biomimetic transformations into other iboga-type alkaloids.
May 20, 2016: Organic Letters
Simon Authier, Michael V Accardi, Dominique Paquette, Mylène Pouliot, Joseph Arezzo, R John Stubbs, Ronald J Gerson, Lawrence T Friedhoff, Holger Weis
INTRODUCTION: Continuous video-electroencephalographic (EEG) monitoring remains the gold standard for seizure liability assessments in preclinical drug safety assessments. EEG monitored by telemetry was used to assess the behavioral and EEG effects of noribogaine hydrochloride (noribogaine) in cynomolgus monkeys. Noribogaine is an iboga alkaloid being studied for the treatment of opioid dependence. METHODS: Six cynomolgus monkeys (3 per gender) were instrumented with EEG telemetry transmitters...
September 2016: Journal of Pharmacological and Toxicological Methods
Choy-Eng Nge, Kam-Weng Chong, Noel F Thomas, Siew-Huah Lim, Yun-Yee Low, Toh-Seok Kam
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 analysis. Two of the iboga alkaloids, conodusines B (2) and C (3), and the iboga-containing bisindole tabernamidine B (10) are notable for the presence of an α-substituted acetyl group at C-20 of the iboga carbon skeleton...
May 27, 2016: Journal of Natural Products
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