Indole alkaloids from Tabernaemontana australis (Müell. Arg) Miers that inhibit acetylcholinesterase enzyme

Andrade, Mônica Calixto de; Lima, Josélia Alencar; Pinto, Ângelo C.; Rezende, Cláudia M.; Carvalho, Meriane P.; Epifânio, Rosangela A.

doi:10.1016/j.bmc.2005.03.045

Cited by 108 publications

(49 citation statements)

References 29 publications

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“…The alkaloids 1-17 (Table I) were previously isolated by the authors and the experimental procedures are described elsewhere (Andrade et al 2005, Medeiros et al 1999, Monnerat et al 2005). …”

Section: Extraction and Isolation Of Alkaloidsmentioning

confidence: 99%

“…They can be found in plants of the Apocynaceae, Rubiaceae, and Loganiaceae families and a few have recently been reported as ChEI by different research groups (Hostettmann et al 2006). Among the AChEI found are some indole glucoalkaloids from Chimarrhis turbinate (Rubiaceae) (Cardoso et al 2004); sarpagan type alkaloids from the Haplophyton crooksii (Apocynaceae) (Mroue et al 1996); iboga alkaloids from Tabernaemontana australis (Apocynaceae) (Andrade et al 2005) and vobasinyl-iboga bis-indole alkaloids from T. divaricata (Ingkaninan et al 2006). In fact, a recent article reported the inhibition of cortical AChE activity and the enhancement of neuronal activity of T. divaricata extracts in rats, suggesting that it is a reversible AChE inhibitor and could be beneficial as a novel therapeutic agent for AD (Chattipakorn et al 2007).…”

Section: Introductionmentioning

confidence: 99%

“…Monoterpenic indole alkaloids have been extensively investigated for exhibiting numerous biological activities (such as anti-tumor, anti-microbial, anti-hypertensive or as a central nervous system stimulant) (Andrade et al 2005, Saxton 1997). They can be found in plants of the Apocynaceae, Rubiaceae, and Loganiaceae families and a few have recently been reported as ChEI by different research groups (Hostettmann et al 2006).…”

Section: Introductionmentioning

confidence: 99%

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Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures

Vieira

Medeiros

Monnerat

et al. 2008

An. Acad. Bras. Ciênc.

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The pharmacotherapy for Alzheimer's disease (AD) includes the use of acetylcholinesterase inhibitors (AChEI). Recent investigations for novel AD therapeutic agents from plants suggested that Tabernaemontana genus is a promising source of novel anticholinesterasic indole alkaloids. In this work two fast screening techniques were combined in order to easily identify novel cholinesterase inhibitors (ChEI). Gas chromatography-mass spectrometry (GC-MS) of the less polar alkaloidic fractions obtained from the acid-base extraction of the stalk of T. laeta revealed thirteen monoindole alkaloids, four of them confirmed by co-injection with previously isolated alkaloids. The others were tentatively identified by mass fragmentation analysis. By gas chromatography with flame ionization detection (GC-FID) and using isatin as internal standard, affinisine and voachalotine were determined as major compounds. These fractions and fourteen previously isolated alkaloids, obtained from root bark of T. laeta and T. hystrix were investigated for acetyl (AChE) and butyrylcholinesterase (BuChE) inhibitory activities by the modified Ellman's method in thin layer chromatography (TLC-ChEI). Results showed selective inhibition of the alkaloids heyneanine and N b -methylvoachalotine for BuChE, and 19-epi-isovoacristine for AChE, whereas olivacine, affinisine, ibogamine, affinine, conodurine and hystrixnine inhibited both enzymes. In addition to confirming that monoterpenoid indole alkaloids can be novel therapeutic agents for AD, this is the first report of the ChEI activity of olivacine, a pyridocarbazole alkaloid.

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Section: Extraction and Isolation Of Alkaloidsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures

Vieira

Medeiros

Monnerat

et al. 2008

An. Acad. Bras. Ciênc.

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“…Numerous chemical constituents from medicinal plants have been reported for their effects on AChEIs. The active compounds are huperzine-A from Huperziaserrata, galantamine from Galanthus nivalis and Narcissus sp., α-viniferin from Caragana chamlague, ursolic acid from Origanum majorana including coronaridine, voacangine and rupicoline from Tabernaemontana australis [8], [9].…”

Section: Introductionmentioning

confidence: 99%

Acetylcholinesterase Inhibitory and Antioxidant Properties of Thai Vegetables

Langyanai¹,

Chaniad²,

Puripattanavong³

2017

IJPMBS

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“…1 The main constituents of the Tabernaemontana genus are indole alkaloids, a class of substances with a wide range of pharmacological activities: cholinesterase inhibitors, 2 analgesic, anti-inflammatory, bactericidal, oestrogenic, and stimulant and depressant of the central nervous system (CNS). 3 Taxonomy of the Apocynaceae family is quite complex and there are difficulties in its classification and terminology because there are a great number of synonyms. Both generic names, Tabernaemontana and Peschiera, have been used in Brazil and are matter of discussion.…”

Section: Introductionmentioning

confidence: 99%

Qualitative determination of indole alkaloids of Tabernaemontana fuchsiaefolia (Apocynaceae)

Zocoler¹,

Oliveira²,

Sarragiotto³

et al. 2005

J. Braz. Chem. Soc.

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Este trabalho descreve um procedimento rápido e eficiente para a separação e identificação de alcalóides indólicos do extrato etanólico de Tabernaemontana fuchsiaefolia (Apocynaceae). As frações alcaloídicas obtidas dos extratos etanólicos (das folhas, das cascas do caule e das cascas das raízes) foram fracionadas e analisadas por cromatografia em camada delgada (CCD) e por cromatografia gasosa acoplada a espectrometria de massa (CG-EM). Foram identificados os alcalóides indólicos ibogamina, coronaridina, pseudoindoxil ibogaina, hidroxiindolenina voacangina, pseudoindoxil voacangina, tabernantina, catarantina, voacangina, 19-oxovoacangina, 10-hidroxicoronaridina, afinisina, 16-epi-afinina, voachalotina, ibogalina e conofaringina. This paper describes a fast and efficient procedure to separate and identify indole alkaloids from the ethanolic extract of Tabernaemontana fuchsiaefolia (Apocynaceae). The alkaloidal fractions obtained from ethanolic extracts of leaves and stem barks and root barks were fractioned and analyzed by Thin-Layer Chromatography (TLC) and by Gas Chromatography coupled to Mass Spectrometry (GC-MS). The following indole alkaloids were identified: ibogamine, coronaridine, ibogaine pseudoindoxyl, voacangine hydroxyindolenine, voacangine pseudoindoxyl, tabernanthine, catharanthine, voacangine, 19-oxovoacangine, 10-hydroxycoronaridine, affinisine, 16-epi-affinine, voachalotine, ibogaline, and conopharyngine.

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Indole alkaloids from Tabernaemontana australis (Müell. Arg) Miers that inhibit acetylcholinesterase enzyme

Cited by 108 publications

References 29 publications

Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures

Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures

Acetylcholinesterase Inhibitory and Antioxidant Properties of Thai Vegetables

Qualitative determination of indole alkaloids of Tabernaemontana fuchsiaefolia (Apocynaceae)

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