Configurational Study of an Aporphine Alkaloid from <i>Annona purpurea</i>

Ontiveros-Rodríguez, Julio C.; Burgueño‐Tapia, Eleuterio; Porras-Ramírez, Javier; Joseph‐Nathan, Pedro; Zepeda, L. Gerardo

doi:10.1177/1934578x1801300711

Cited by 4 publications

(7 citation statements)

References 36 publications

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“…1). The NMR data of compounds 1-3 were identical to those recently reported [18]. While the NMR 1 H data of compound 5 were consistent with a previous report [19], the full assignment of the 13 C NMR data is presented here for the first time.…”

Section: Resultssupporting

confidence: 90%

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Anti-amoebic Activity of Leaf Extracts and Aporphine Alkaloids Obtained from Annona purpurea

et al. 2020

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Annona purpurea has been traditionally used by indigenous and socioeconomically disadvantaged people to treat infectious and parasitic diseases, including amoebiasis. The goal of this study was to assess the effect of a crude methanolic extract, an alkaloid extract, and aporphine alkaloids from leaves of A. purpurea on the viability of Entamoeba histolytica trophozoite cultures and to identify the mechanism of action. Different concentrations of the extracts and alkaloids purpureine (1), 3-hydroxyglaucine (2), norpurpureine (3) glaziovine (4), and oxopurpureine (5) were added to the cultures, and dead parasites were counted after 24 h using a tetrazolium dye reduction assay and analyzed by flow cytometry. The crude extract did not affect the viability of amoebae, but the alkaloid extract and the derived alkaloid glaziovine (4) had important anti-amoebic activity with an IC50 of 33.5 µM compared to that shown by metronidazole (6.8 µM). The treatments induced significant morphological changes in the trophozoites, and most parasites killed by the alkaloid extract were positive for Annexin V, suggesting that apoptosis was the main mechanism of action. In contrast, glaziovine (4) induced less apoptosis with more amoebic lysis. This study supports the idea that aporphine alkaloids from A. purpurea, mainly (+)-(R)-glaziovine (4), could contribute to the development of new formulations for the treatment of amoebiasis. In addition, X-ray diffraction structural analysis and complete 1H and 13C NMR assignments of (+)-(R)-glaziovine (4) were performed and reported for the first time.

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Section: Resultssupporting

confidence: 90%

“…Elution with EtOAc-MeOH 9 : 1 gave 490 mg of a mixture of purpureine (1) tion from EtOAc. The NMR data of 1, 2, and 3 were identical to data reported previously [18].…”

Section: Extraction and Isolationsupporting

confidence: 82%

Anti-amoebic Activity of Leaf Extracts and Aporphine Alkaloids Obtained from Annona purpurea

et al. 2020

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“…The TALC was determined according to the procedure described by Ontiveros-Rodriguez et al [24] with modifications. The methanolic extracts obtained were diluted with 10 mL of methanol, and 5 mL of 5% HCl were added.…”

Section: Total Alkaloid Content (Talc)mentioning

confidence: 99%

“…Extraction by maceration was carried out with 2 g of freeze-dried sample in 15 mL of methanol at room temperature for one week [24]. After maceration, the methanolic extracts were treated and quantified, as described in Section 2.3.…”

Section: Extraction By Maceration (Me) Of Alkaloidsmentioning

confidence: 99%

Extraction of Alkaloids Using Ultrasound from Pulp and By-Products of Soursop Fruit (Annona muricata L.)

et al. 2020

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The main goal of this work was to measure the total alkaloid content (TALC) from pulp, peel, seed, and columella of soursop fruit (Annona muricata L.) by ultrasound-assisted extraction (UAE) and to obtain the best conditions of the UAE with the response surface methodology (RSM). We evaluated the effect of amplitude (40%, 70%, and 100%), time (5, 10, and 15 min) and pulse-cycles (0.4, 0.7, and 1 s) and compared the best UAE conditions of alkaloids with a conventional extraction (maceration). The structural characterization of the raw material with the highest TALC was developed using nuclear magnetic resonance (NMR) techniques [1H, 13C, heteronuclear single quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC), and homonuclear correlation spectroscopy (COSY)]. According to the RSM, the best conditions in the UAE for extracting alkaloids varied depending on the type of plant tissue. It took 5 min with an amplitude of 70% and pulse-cycles of 1, 0.4, and 1 s, respectively, to extract the highest TALC in peel, seed, and columella while the optimal conditions for extracting the largest amount of alkaloids from the pulp were obtained at 5 min in UAE with pulse-cycles of 0.55 s and 100% amplitude. The TALC was highest in the peel (7.48 mg/g), which was followed by the seed (2.31 mg/g), the pulp (1.20 mg/g), and the columella (0.79 mg/g) and was positively correlated (R2 = 0.98–0.88) with the predicted values. In addition, the extraction alkaloids from the peel, pulp, seed, and columella using the UAE was 56.31, 5.45, 3.06, and 2.96 times higher, respectively, than the extraction by maceration. The alkaloids identified in the peel have not been reported and were nornuciferin, assimilobin, anonaine, and isolaureline. This study showed that the soursop fruit peel can be a source of alkaloids and that UAE has an important potential for extracting these compounds.

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“…The optimal anharmonicity factor (anH) was 1.011, which is in concordance with values for correcting IR, Raman, and VCD calculations of organic compounds [36][37][38] due to underestimated vibration frequencies (around 20 cm −1 ) 39 inherent to the PBEPBE functional. 40,41 This functional has been used successfully when calculating some molecules possessing an aromatic ring, like epoxythymols 30,42 and an aporphine alkaloid, 43 for which the anharmonicity factor was always above the unit, specifically in the 1.002-1.020 range. Anharmonicity factors above the unit are not exclusive for the PBEPBE functional, as a 1.007 value became evident when myrtenal was calculated at the B3PW91/DGTZVP level of theory.…”

Section: Resultsmentioning

confidence: 99%

Conformational, configurational, and supramolecular studies of podocephalol acetate from Lasianthaea aurea

et al. 2019

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Although podocephalol (1) and its derived acetate 2 were found in Lasianthaea podocephala four decades ago, and 1 was later detected in the essential oils of several vegetal species, its absolute configuration (AC) and conformational preferences remained to be established. The structures of ar‐himachalene 1, now isolated from Lasianthaea aurea, and its derived acetate 2, were herein confirmed by extensive 1D and 2D nuclear magnetic resonance (NMR) studies, while the conformational preferences of the cycloheptene was established by density functional theory (DFT) calculations, which in combination with vibrational circular dichroism measurements provided the (R) absolute configuration of the molecules. The structure and AC were further verified through the Flack and Hooft parameters calculations derived from single crystal X‐ray diffraction data of 2. In addition, careful evaluation of the crystal data allowed observing supramolecular layers cell package, an uncommon property in natural terpenes that might have potential applications. A transmission electron microscopy analysis of crystal of 2 was also possible, providing its physical characteristics at the micrometric scale.

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Configurational Study of an Aporphine Alkaloid from Annona purpurea

Cited by 4 publications

References 36 publications

Anti-amoebic Activity of Leaf Extracts and Aporphine Alkaloids Obtained from Annona purpurea

Anti-amoebic Activity of Leaf Extracts and Aporphine Alkaloids Obtained from Annona purpurea

Extraction of Alkaloids Using Ultrasound from Pulp and By-Products of Soursop Fruit (Annona muricata L.)

Conformational, configurational, and supramolecular studies of podocephalol acetate from Lasianthaea aurea

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