Acaricidal and insecticidal activity of essential oils obtained from the aerial parts of three Mexican Bursera species.

In search of new sustainable biopesticides, we determined the phytochemical profiles, acaricidal and insecticidal properties of EOs distilled from the aerial parts of three Mexican Bursera species. Results were obtained by GC-MS analysis and three different bioassays, indicating that the EO of Bursera glabrifolia exhibited high relative abundancies of α-pinene, ß-myrcene, and α-phellandrene, as well as promising pesticidal activity against Spodoptera littoralis larvae (LD50,90 = 32.4, 107.2 µg/larva), and Musca domestica (LD50,90 = 23.2, 103.2, and 13.5, 77.4 µg/female or male adult, respectively) and Tetranychus urticae adults (LD50,90 = 7.4, 30.3 µg/cm2). The Bursera lancifolia and Bursera linanoe samples contained mainly D-limonene or linalyl acetate and linalool, respectively, and showed generally less potent pesticidal properties (S. littoralis larva, LD50,90 = 45.4, 154.4 and 52.2, 158.7 µg/larva, respectively; female M. domestica adult, LD50,90 = 69.2, 210.9 and 45.1, 243.8 µg/female adult, respectively; T. urticae adults, LD50,90 = 20.7, 90.5 and 17.5, 71.4 µg/cm2, respectively). However, the EO of B. linanoe exhibited an especially pronounced activity against male M. domestica adults (LD50,90 = 10.6, 77.2 µg/male adult). Our findings prove the pesticidal potential of Mexican Bursera species in the context of integrated pest management (IPM) and highlight the importance of conducting further research to elucidate both the active principles and possibly existing synergistic effects.

Inhibitory effects of methanolic extracts from the stem barks of ten Mexican Bursera Jacq. ex L. species on the activity of α-amylase and acetylcholinesterase from Tenebrio molitor.

Methanolic stem bark extracts from ten Mexican Bursera Jacq. ex L. species were evaluated in vitro with regard to their inhibitory activity against two Tenebrio molitor-derived enzymes. Seven extracts (B. bicolor, B. copallifera, B. fagaroides, B. grandifolia, B. lancifolia, B. linanoe, and B. longipes) reduced α-amylase activity by 55.37% to 96.25%, with three samples proving to be particularly potent α-amylase inhibitors (B. grandifolia, B. lancifolia, and B. linanoe; IC50 = 162, 132, and 186 µg/mL, respectively). In contrast, no extract inhibited acetylcholinesterase activity by more than 39.94%. Quantitative HPLC analysis did not reveal any clear correlation between the species-specific flavonoid or phenolic acid profiles and the respective extracts' enzyme inhibitory activity. The findings reported herein do not only contribute to improving the current state of knowledge regarding the enzyme inhibitory potential of the Bursera genus, but could also lead to the development of new sustainable bioinsecticides.

Quantitative Evaluation of a Mexican and a Ghanaian Tabernaemontana Species as Alternatives to Voacanga africana for the Production of Antiaddictive Ibogan Type Alkaloids.

In continuation of our efforts to provide quantitative information on antiaddictive ibogan type alkaloid-producing Tabernaemontana species, we used gas chromatography-mass spectrometry (GC/MS) to compare the alkaloid profiles of the barks and/or leaves of one Mexican and one African species - T. arborea and T. crassa, respectively, with the primary sources of commercially available semisynthetic ibogaine, Voacanga africana root and stem bark. The qualitative and quantitative similarities between T. arborea and V. africana barks consolidate previous reports regarding the potential of the former as 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.

Extraction and Conversion Studies of the Antiaddictive Alkaloids Coronaridine, Ibogamine, Voacangine, and Ibogaine from Two Mexican Tabernaemontana Species (Apocynaceae).

Several species from the Apocynaceae family, such as Tabernanthe iboga, Voacanga africana, and many Tabernaemontana species, produce ibogan type alkaloids, some of which present antiaddictive properties. In this study, we used gas chromatography/mass spectrometry (GC/MS) to examine the efficiency of methanol, acetone, ethyl acetate, dichloromethane, chloroform, and hydrochloric acid in extracting the antiaddictive compounds coronaridine, ibogamine, voacangine, and ibogaine (altogether the CIVI-complex) from the root barks of Tabernaemontana alba and Tabernaemontana arborea. These Mexican species have recently shown great potential as alternative natural sources of the aforementioned substances. Methanol proved to be the most suitable solvent. Furthermore, the crude methanolic extracts could be engaged in a one-step demethoxycarbonylation process that converted coronaridine and voacangine directly into its non-carboxylic counterparts ibogamine and ibogaine, respectively, without the intermediacy of their carboxylic acids. The established protocol straightforwardly simplifies the alkaloid mixture from four to two majority compounds. In summary, our findings facilitate and improve both the qualitative and quantitative analysis of CIVI-complex-containing plant material, as well as outlining a viable method for the bulk production of these scientifically and pharmaceutically important substances from Mexican Tabernaemontana species.

Metabolite Profiling of Anti-Addictive Alkaloids from Four Mexican Tabernaemontana Species and the Entheogenic African Shrub Tabernanthe iboga (Apocynaceae).

Ibogaine and other ibogan type alkaloids present anti-addictive effects against several drugs of abuse and occur in different species of the Apocynaceae family. In this work, we used gas chromatography-mass spectrometry (GC/MS) and principal component analysis (PCA) in order to compare the alkaloid profiles of the root and stem barks of four Mexican Tabernaemontana species with the root bark of the entheogenic African shrub Tabernanthe iboga. PCA demonstrated that separation between species could be attributed to quantitative differences of the major alkaloids, coronaridine, ibogamine, voacangine, and ibogaine. While T. iboga mainly presented high concentrations of ibogaine, Tabernaemontana samples either showed a predominance of voacangine and ibogaine, or coronaridine and ibogamine, respectively. The results illustrate the phytochemical proximity between both genera and confirm previous suggestions that Mexican Tabernaemontana species are viable sources of anti-addictive compounds.

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

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.