Quantification of Anti‐Addictive Alkaloids Ibogaine and Voacangine in In Vivo‐ and In Vitro‐Grown Plants of Two Mexican Tabernaemontana Species

Abstract

Tabernaemontana alba and Tabernaemontana arborea are Apocynaceae species used in Mexican traditional medicine for which little phytochemical information exists. In this study, preliminary gas chromatography/mass spectrometry analyses of different organs obtained from wild plants of both species identified a total of 10 monoterpenoid indole alkaloids (MIAs) and one simple indole alkaloid, nine of which were reported for the first time in these species. Furthermore, callus cultures were established from T. alba leaf explants and regeneration of whole plants was accomplished via somatic embryogenesis. The anti-addictive MIAs ibogaine and voacangine were then quantified by gas chromatography with flame ionization detection in wild plants of both species, as well as greenhouse-grown plants, in vitro-grown plantlets and embryogenic callus of T. alba. Ibogaine and voacangine were present in most samples taken from the whole plants of both species, with stem and root barks showing the highest concentrations. No alkaloids were detected in callus samples. It was concluded that T. alba and T. arborea are potentially viable sources of ibogaine and voacangine, and that these MIAs can be produced through somatic embryogenesis and whole plant regeneration of T. alba. Approaches to increase MIA yields in whole plants and to achieve alkaloid production directly in cell cultures are discussed.

Antimycobacterial Activity of Alkaloids and Extracts from Tabernaemontana alba and T. arborea

“…1). All the samples contained at least one ibogan-type alkaloid (coronaridine, ibogaine, ibogamine, and/or voacangine) and the corynanthean-type MIA vobasine, as previously reported [10,11,14]. The aspidospermatan-type alkaloid apparicine was only found in the T. alba extracts.…”

“…7 . The first and the last species have been reported to be used in Mexican traditional medicine due to their analgesic, anti-inflammatory, antiparasitic, and/or dermatological properties 8 , 9 , and all three are known to contain significant amounts of monoterpenoid indole alkaloids (MIAs) of the ibogan-type subclass, particularly, coronaridine, ibogamine, voacangine, and ibogaine 10 , 11 .…”

The Antiviral and Virucidal Activities of Voacangine and Structural Analogs Extracted from Tabernaemontana cymosa Depend on the Dengue Virus Strain

“…Cytotoxicity was dependent on the compound and its concentration when the viability of the Vero cell line treated with the three compounds was assessed ( Figure 1 D–F). This could be explained by the minor structural differences of each compound, which could induce differential toxicity, as has been previously reported [ 31 , 32 ]. In agreement with our findings, cytotoxicity has also been described as dependent on the concentration of indole alkaloids extracted from other Tabernaemontana species such as T. inconspicua [ 33 ].…”

Apocináceas de ayer y hoy. Conocimiento histórico y reevaluación de la diversidad y distribución de Apocynaceae en México

“…A la par del conocimiento sistemático, otros rubros se han abordado en el grupo, pero no con tanta atención. Entre ellos se pueden señalar trabajos de índole fitoquímica con especies de Asclepias L. (Domínguez et al 1958, Fonseca et al 1991, Navarro-García et al 2003, Rascón-Valenzuela et al 2015, Cascabela (Ramos-Silva et al 2017), Haplophyton (Mroue et al 1993, Llanos-Romero et al 2014 y Tabernaemontana (Krengel et al 2016(Krengel et al , 2019. Los de conocimiento etnobotánico (Heinrich et al 1992, García-Alvarado et al 2001, Fernández-Brewer et al 2008, de polinización (Kunze 1999, Liede 1994, Ollerton et al 2018, así como de ecología de frutos y semillas (Coates-Estrada et al 1993, Bebawi et al 2017.…”