Chemistry and biology of the genus<i>Voacanga</i>

Hussain, Hidayat; Hussain, Javid; Al‐Harrasi, Ahmed; Green, Ivan R.

doi:10.3109/13880209.2012.658478

Cited by 23 publications

(17 citation statements)

References 32 publications

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“…In summary, untreated methanol should be used to extract the whole CIVI-complex from Apocynaceae species that contain considerable quantities of these alkaloids, like Mexican Tabernaemontana species [10,11] or V. africana, [15] particularly when conducting quantitative alkaloid profiling studies. If selective bulk extraction of voacangine (3) and/or ibogaine (4), but not coronaridine (1) and/or ibogamine (2) was the aim, ammonium-supplemented acetone, ethyl acetate, dichloromethane, or chloroform could be an alternative to methanol, particularly when taking into account the higher selectivity of the former compared to the latter.…”

Section: Extraction Efficiency Of Different Solventsmentioning

confidence: 99%

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

Krengel

Mijangos

Reyes‐Lezama

et al. 2019

Chemistry & Biodiversity

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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.

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Section: Extraction Efficiency Of Different Solventsmentioning

confidence: 99%

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

Krengel

Mijangos

Reyes‐Lezama

et al. 2019

Chemistry & Biodiversity

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“…The crude methanol extract of V. africana was subjected to silica gel normal phase open column chromatography and elution with a gradient of ethyl acetate in hexane. Repeated column chromatography through Sephadex LH-20, preparative thin-layer chromatography (TLC) yielded a new bisindole alkaloid derivative named voacamine A (1) along with eight known compounds, voacangine (2), voacristine (3),coronaridine (4), tabernanthine (5), iboxygaine (6), voacamine (7), voacorine (8), and conoduramine (9) [16][17][18][19][20][21][22][23][24][25] (Figure 1). The structures of the compounds were established based on NMR ( Figures S3-S25) analyses as well as by comparison with published data.…”

Section: Isolation and Identification Of Alkaloidsmentioning

confidence: 99%

“…For example, the root bark of the plant is used to treat diarrhoea in Kinshasa, the Democratic Republic of Congo [1], while the stem bark has been used in combination with the sister species V. thouarsii in the treatment of heart disease, leprosy, diarrhoea, generalized oedema, madness and convulsions in children in Ivory Coast, Cameroon, Ghana and Congo [2,3]. Additionally, the fruits, bark and leaf extracts have been used in Cameroonian ethnomedicine to treat orchitis, ectopic testes and gonorrhoea, respectively [4][5][6][7][8]. Of late, Apocynaceous plants have been under scientific investigation.…”

mentioning

confidence: 99%

“…Monoterpenoids and bisindole alkaloids are the major classes of secondary metabolites isolated from this plant family [9][10][11][12]. Recently, our research group carried out investigations that led to the identification of the alkaloids voacangine (2) and voacamine (7), from the stem bark of V. africana, with both compounds showing activity against Onchocerca ochengi [13]. The cattle derived O. ochengi is the best model and closest known relative of O. volvulus based on phylogenetic relationship [14].…”

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confidence: 99%

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Compounds with Anti-Onchocercal Activity from Voacanga africana Stapf (Apocynaceae): Identification and Molecular Modeling

Babiaka¹,

Simoben²,

Abuga³

et al. 2020

Preprint

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A new iboga-vobasine-type isomeric bisindole alkaloid named voacamine A (1), along with eight known compounds, voacangine (2), voacristine (3), coronaridine (4), tabernanthine (5), iboxygaine (6), voacamine (7), voacorine (8), and conoduramine (9), were isolated from the stem bark of Voacanga africana. The structures of the compounds were determined by comprehensive spectroscopic analyses (1D- and 2D-NMR). Compounds 1, 2, 3, 4, 6, 7 and 8 were found to inhibit the motility of both the microfilariae (Mf) and adult male worms of Onchocerca ochengi, in a dose-dependent manner, but were only moderately active on the adult female worms upon biochemical assessment at 30 μM drug concentrations. The IC50 values of the isolates are 2.49-5.49 µM for microfilariae and 3.45-17.87 µM for adult males. Homology modeling was used to generate a 3D model of the the O. ochengi thioredoxin reductase target and docking simulation attempted to offer an explanation of the anti-onchocercal structure-activity relationship (SAR) of the isolated compounds. These alkaloids are new potential leads for the development of antifilirial drugs. The results of this study validate the traditional use of V. africana in the treatment of human onchocerciasis.

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“…Its MIC is 4 µg/ml, which explains the usage of the plant in treatment. In comparison, in the same plant, researchers found that lupeol had no activity against M.tuberculosis [23]. Terminalia sericea, known among native African tribes, has quite potent anti-mycobacterial properties.…”

Section: Extracts and Natural Substances Isolated From Plantsmentioning

confidence: 99%

Anti-tubercular substances produced by plants

Polak¹,

Kapka‐Skrzypczak²

2017

J Pre Clin Clin Res.

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Tuberculosis is one of the common causes of death worldwide, and according to the World Health Organization, in 2015, about 10.4 mln people globally is suffering from that disease. Despite great development in medicine and discovery of many antimycobacterial drugs, tuberculosis remains an unsolved problem. The populations of countries in Africa, Asia and South America have difficult access to hygiene, medical care and medicines, and they therefore resort to consulting traditional practitioners who mainly use drugs from natural sources which they prepare themselves. Plants are the biggest source of such medicines and are used as extracts, decoctions or powders, often without any evidence of their actual activity. Isolates from plants sometimes contain unknown substances or some second metabolites of microorganisms. In vitro studies have shown that some of these medicines have effective antimycobacterial properties, even against clinical, resistant strains. This is hopeful in the situation where more and more cases of tuberculosis prove to be resistant to standard drugs. Extracts of medicinal plants are often synergistic with synthetic drugs. Substances with insufficient MIC can be a basis for derivatives which have better properties. This thesis summarizes the current international knowledge of the use of plant substances used in the treatment of tuberculosis that could be potential new antituberculous drugs.

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Chemistry and biology of the genusVoacanga

Cited by 23 publications

References 32 publications

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

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

Compounds with Anti-Onchocercal Activity from Voacanga africana Stapf (Apocynaceae): Identification and Molecular Modeling

Anti-tubercular substances produced by plants

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