Full NMR analysis of annomontine, methoxy‐ annomontine and <i>N</i>‐hydroxyannomontine pyrimidine‐β‐carboline alkaloids

Costa, Emmanoel V.; Pinheiro, Maria Lúcia B.; Souza, Afonso Duarte Leão de; Santos, Adriane Gama dos; Campos, Francinete Ramos; Ferreira, Antônio G.; Barison, Andersson

doi:10.1002/mrc.2134

Cited by 14 publications

(17 citation statements)

References 7 publications

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“…Further inspection of 1 H NMR and COSY spectra showed the presence of 2 ortho-coupled protons at δ H 8.49 (H-4′) and 7.82 (H-5′) for the 2-aminopyrimidine moiety. The 13 C NMR data of 3 were comparable to those of 1 as well as the reported data for 2-aminopyrimidine moiety [3,6,7]. The attachment of the 2-aminopyrimidine moiety at C-1 was established by the HMBC correlations of H-4′and H-5′ to C-1.…”

Section: Conformational Analysissupporting

confidence: 80%

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Ingenines A and B, Two New Alkaloids from the Indonesian Sponge Acanthostrongylophora ingens

et al. 2014

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As a continuation of the work on EtOAc fraction of the Indonesian sponge Acanthostrongylophora ingens, 2 new alkaloids: one pyrimidine-β-carboline alkaloid named ingenine A (2) and one pyrimidine-γ-carboline alkaloid named ingenine B (3), along with annomontine (1) were isolated. Their structures were unambiguously established on the basis of NMR spectroscopy ((1) H, (13)C, (1) H-(1) H COSY, HMQC, and HMBC) and mass spectral data. This is the first report of isolation pyrimidine-γ-carboline alkaloid from natural source. Compounds 1 and 3 showed pronounced cytotoxicity against the murine lymphoma L5178Y cancer cell line with ED50 7.8 and 9.1 μg/mL respectively, while compound 2 showed weak activity.

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Section: Conformational Analysissupporting

confidence: 80%

“…From the obtained data in • ▶ Table 1, it was noticed that ingenine A is more energetically stable than annomontine (1). data of 3 were similar to that of 1 • ▶ Table 3 [3,6,7]. The 1 H NMR and COSY spectra showed the existence of 3 spin systems.…”

Section: Conformational Analysismentioning

confidence: 54%

Ingenines A and B, Two New Alkaloids from the Indonesian Sponge Acanthostrongylophora ingens

et al. 2014

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“…A single alkaloid eluted from the column with n-hexane : ethyl acetate : methanol (60 : 40 : 0) was crystallized from fractions 166-186. The crystals obtained from these fractions (75 mg) were identified by their melting points and their chromatographic and spectroscopic properties as annomontine [2,3]. Resonance analysis of 1 H, 13 C, and HPLC determined that the purity of annomontine was > 99 %.…”

Section: Purification and Identification Of The Alkaloidsmentioning

confidence: 99%

“…The first two alkaloids were first isolated from Annona montana [1] and the last from Annona foetida [2]. More recently the three alkaloids have been isolated from Annona reticulata [3]. The pharmacological and biochemical properties of this type of alkaloids are scarcely documented.…”

mentioning

confidence: 99%

Annomontine, an Alkaloid Isolated fromAnnona purpurea, Has Anxiolytic-Like Effects in the Elevated Plus-Maze

Orantes¹,

González‐Esquinca²,

Mora³

et al. 2010

Planta Med

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The effects of annomontine, a pyrimidine- β-carboline alkaloid isolated from the root of ANNONA PURPUREA, on anxiety was studied in mice using the elevated plus-maze. The behavioral effects of this alkaloid on the pentobarbital-induced hypnosis, the locomotor activity in an open field, and the motor coordination in the rotarod test were also evaluated. The intraperitoneal injection of annomontine (1-30 mg/kg) increased in a dose-dependent way the number of visits to and the time spent in the open arms of the elevated plus-maze in comparison to the control animals. Such effects were blocked by the prior application of flumazenil (3 mg/kg; i. p.), a specific antagonist for the binding of benzodiazepines on the GABA (A) receptor. Under the same experimental conditions annomontine failed to affect the behavior of the animals in the pentobarbital-induced hypnosis test and had no effects on locomotion and motor coordination. These results suggest that annomontine possesses anxiolytic-like effects which may be mediated at the level of the benzodiazepine binding site on the GABA (A) receptor.

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“…There are some reports about the characterization of general pyrimidinic compounds based on NMR spectroscopy [9,10] and X-ray scattering of crystallin supramolecular structures techniques [11][12][13]. There are very few reports, however, dedicated to the structural assignement of pyrimidines based on X-ray crystallography associated with theoretical *Address correspondence to this author at the Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, CEP --97.105-900, Santa Maria, RS, Brazil; Tel: +55 55 3220 8756; Fax: +55 55 3220 8756; E-mail: zanatta@base.ufsm.br calculations or to the aromatic character quantification of such heterocycles [14][15][16] and, to the best of our knowledge, there are no studies of this nature dealing with N'-benzylidenehydrazino pyrimidines.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure, Aromatic Character and AM1 Calculations of 2-(N`- Benzylidenehydrazino)-4-trifluoromethyl-pyrimidine and 2-(N`-2-Methylbenzylidenehydrazino)- 5-methyl-4-trifluoromethyl-pyrimidine~!2010-02-08~!2010-05-04~!2010-06-22~!

Amaral¹,

Campos²,

Santos³

et al. 2010

TOCRYJ

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The structure of two novel 2-(N'-benzylidenehydrazino)-4-trifluoromethyl-pyrimidines has been determined by X-ray crystallography and their energy-minimized structures were stablished by molecular orbital calculations (AM1) by means of comparison. Additionally, the bond lengths of the compounds were analyzed in order to verify the occurance of electronic resonance. Bond lengths and bond angles in the pyrimidine ring and the benzylidene portion compare well with those found in similar compounds. 2-(N'-benzylidenehydrazino)-4-trifluoromethyl-pyrimidine, crystallized in the triclinic space group P-1 solvated with a molecule of water, while 2-(N'-2-methyl-benzylidenehydrazino)-5-methyl-4trifluoromethyl-pyrimidine crystallized in the tetragonal space group P41. The azomethine moieties showed a trans-planar conformation. The energy-minimized structures of both compounds are in good agreement with their X-ray crystal structures. Nevertheless, a significant difference between calculated and experimental data regarding to the ring planarity was observed due to relevant intermolecular interactions in the real structures. Finally, aromaticities of both pyrimidines and phenyl rings were determined using HOMA calculations.

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Full NMR analysis of annomontine, methoxy‐ annomontine and N‐hydroxyannomontine pyrimidine‐β‐carboline alkaloids

Cited by 14 publications

References 7 publications

Ingenines A and B, Two New Alkaloids from the Indonesian Sponge Acanthostrongylophora ingens

Ingenines A and B, Two New Alkaloids from the Indonesian Sponge Acanthostrongylophora ingens

Annomontine, an Alkaloid Isolated fromAnnona purpurea, Has Anxiolytic-Like Effects in the Elevated Plus-Maze

Crystal Structure, Aromatic Character and AM1 Calculations of 2-(N`- Benzylidenehydrazino)-4-trifluoromethyl-pyrimidine and 2-(N`-2-Methylbenzylidenehydrazino)- 5-methyl-4-trifluoromethyl-pyrimidine~!2010-02-08~!2010-05-04~!2010-06-22~!

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