Annona Purpurea Research Articles

Biosynthesis of Copper Nanoparticles from Acacia cornigera and Annona purpurea and Their Insecticidal Effect against Tribolium castaneum

Diverse studies have showed that the pesticides can cause important damages in ecosystem. Therefore, the development of bio pesticides through nanotechnology can increase efficacy and limit the negative impacts in the environmental that traditionally seen through the use of chemical pesticides. Nanoparticles obtained from plants’ extracts can be used for effective pest management as a combined formulation of metal and some other organic material present in the plants. In the present study, our evaluated biosynthesis of nanoparticles of copper used two plant extracts (Acacia cornigera and Annona purpurea), and the Taguchi method was adopted for the synthesis optimization of the following variables of biosynthesis: temperature, pH, extract concentration, and reaction times to maximize the insecticidal activity on Tribolium castaneum. Our results showed that the nanoparticles were successfully synthesized using Acacia cornigera and Anona purpurea extract under optimum conditions under Taguchi L 9 orthogonal design, where copper nanoparticles were obtained with a size of 63–153 nm for using A. cornigera extract, 87–193 nm for A. purpurea extract, and a zeta potential of 9.6 mV and −32.7 mV, respectively. The nanoparticles of copper from A. cornigera showed effective insecticidal activity against Tribolium castaneum, and 90% mortality compared to the 76.6% obtained from nanoparticles of copper from A. purpurea. The results suggest that Cu-nanoparticles derived from both plants could be used as a biocontrol agent of Tribolium castaneum, a pest of stored grain with great economic importance.

Effect of Warm-Dry Storage and Supplemental Application of Gibberellins on the Lipid Profile of Chincuya Seeds (Annona purpurea Moc. & Sessé ex Dunal)

Despite ample knowledge of the effect of warm-dry storage on breaking dormancy in chincuya (Annona purpurea Moc. & Sessé ex Dunal) seeds, this paper investigates an important new aspect of this process—the applicability of seed treatment with gibberellic acid and its influence on seed viability and fatty acid profile. Chincuya is an underutilized, tropical wild species native to Mexico, with potential as a biopesticide. The impact of warm-dry storage and gibberellic acid treatment on seed viability and germination was determined to improve that knowledge further. Also, the content and kinetics of fatty acids in chincuya seeds were profiled during warm-dry storage. Seed treatments included storage time (0, 3, 6, 9, and 12 months), seed imbibition for 72 h in gibberellic acid at 350 mg L−1, and distilled water imbibition for 72 h for the control treatment. Seed viability was determined using the TTZ classic test. Imbibed seeds were germinated on paper towels and incubated at 30 °C during the day and 25 °C at night in a 12:12 h dark/light photoperiod. The lipid profile was obtained by gas chromatography. During the storage treatment, seeds stayed in darkness at 25 ± 3 °C. Results showed that high viability remained up to month 9 in storage when it significantly decreased. Freshly harvested seeds germinated at a statistically significantly lower rate (26.1%) than six-month-old seeds (65.6%). The profile of fatty acids breaks down as palmitic acid (33.41%), stearic acid (7.72%), and arachidic acid (1.30%), for a total of 42.44% of saturated fatty acids. The detected unsaturated fatty acids (52.15%) were palmitoleic acid (1.52%), oleic acid (43.37%), and linoleic acid (7.24%). No significant changes were detected in fatty acid content; however, the highest fatty acid content (92.84%) occurred with the highest germination rate. Regression analysis showed significant content changes: palmitoleic and palmitic acids increased while oleic acid decreased during dry storage. Arachidic acid showed a slight downward trend. Also, fatty acid content significantly differed between intact seeds (unstored and unincubated) and latent seeds (unstored, incubated, and ungerminated). The total fatty acids content for latent seeds was significantly lower. These results show that Annona purpurea seeds present morphophysiological dormancy. Also, we document the highest germination rate reported (65.6%) and report the presence of arachidic and palmitoleic acids in chincuya seeds.

Alkaloidal variation in seedlings of Annona purpurea Moc. & Sessé ex Dunal infected with Colletotrichum gloeosporioides (Penz.) Penz. and Sacc.

Annona purpurea is a species of the Annonaceae family that more than 50 alkaloids. Some alkaloids carry out defense functions and can be grouped from an ecological perspective as constitutive and induced metabolites. The latter are expressed in response to changes in abiotic or biotic conditions that trigger stress in a plant. However, there are few systematic studies of constitutive metabolite profiles and their responses to biotic stress, despite the relevance of this concept. This work analyzed the differences in constitutive and induced alkaloids in A. purpurea seedlings infected with the phytopathogen Colletotrichum gloeosporioides. For this study, methanolic extracts of seedling leaves, stems, and roots inoculated with the fungus and not inoculated with the fungus were obtained and analyzed by gas chromatography coupled to mass spectrometry. The richness and abundance of alkaloids between the treatments and between organs were represented using the Margalef, Shannon, and Simpson ecological indices and the analysis of principal components, PERMANOVA, and paired PERMANOVA. Twenty-one alkaloids were detected from two biosynthetic pathways distributed in the seedling organs, and 15 of these alkaloids were considered constitutive because they are also found in adults. Most of the constitutive alkaloids in the seedlings were observed in the roots (15 compounds), followed by the stems (11 chemicals) and leaves (9 chemicals). The diversity indices also showed differences between the organs. Infection with the fungus modified the constitutive profile of the alkaloids by inducing an increase in lirinidine (61%) and papaverine (403%) in the roots and N,N-dimethyl, 2-(methylamino) 3-phenylindole (143%) in the leaves. Due to the infection, no new alkaloids were detected in any organ.

Morfometria de sementes de Chincuya (Annona purpurea Moc. &Sessé ex Dunal) e crescimento embrionário sob armazenamentos quente e seco

Abstract In Mexico, Annona purpurea Moc. &Sessé ex Dunal, chincuya is found in mountains and family gardens. It is used as food (fruits), traditional medicine (leaves, stems, roots, seeds, bark), wood in construction, papermaking, carpentry, rope making, and as fuel. There is not enough information on the seed, nor on germination management, which is scarce, prolonged and erratic. Considering that the morphophysiological dormancy is the probable cause, it was necessary, within a broader project, to start with the characterization of the seed and determine the effect of dry warm storage (DWS) on it. The perimeter and length of the embryos increased due to the increase in length of the cotyledons and the hypocotil root axis, while the middle hypocotyl area decreased, forming an acinturated embryo. These data indicate that the embryos of chincuya are underdeveloped since they grew and modified their shape, due to the effect of DWS, until the 6th month. This development of the embryo within the seed during dry warm storage confirms the presence of morphological dormancy. This is the first report of embryo growth and characterization of chincuya seeds.

Natural bioeffective cyclooligopeptides from plant seeds of Annona genus.

The Annona L. is one of the most significant genus of the Annonaceae family due to its widespread medicinal properties. This genus has a variety of active metabolites, including alkaloids, isoquinolines, peptides, acetogenins, lectins, volatile oils etc. Due to the constitution of cyclopeptides with an expanded spectrum of distinctive bioproperties, this genus is predominantly preferred over other species. The cytotoxicity, vasorelaxant activity, anti-inflammatory and other properties exhibited by cyclooligopeptides from seeds of Annona genus plants make these metabolites attractive leads for the drug discovery process. The present review covers the structural characteristics, structure activity relationship, synthesis strategies, pharmacological properties of plant seeds-originated bioactive peptides from Annona genus, which may be vital for the development of novel therapeutics based on peptide skeleton.

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

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.

HPLC-DAD method for the detection of five annopurpuricins in root samples of Annona purpurea.

Annona purpurea is a species known in Mexico as "cabeza de negro". In folk medicine A. purpurea root is used to treat patients with kidney diseases and cancer. Our recent studies demonstrated that this species contains five acetogenins named annopurpuricins A-E, which are active against tumoural cell lines in a subnanomolar range. To develop an analytical method using a high-performance liquid chromatography diode array detector (HPLC-DAD) to quantify annopurpuricins A-E in different A. purpurea root samples. To quantify the five annopurpuricins A-E a sample treatment was carried out, which consisted of fractionation by means of cold and hot maceration; using solvents of ascending polarity: hexane, dichloromethane, methanol and water. The resulting extracts were subject to HPLC-DAD analysis. The optimised chromatographic separation on a XBRIDGE C18 column achieved separation of all compounds in around 30 min. The developed method was validated according to ICH (International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use) validation guide. The developed analytical method was found fast, economic, robust, sensitive, linear and precise. The dichloromethane extract of A. purpurea contains annopurpuricin A in quantities 2- to 25-fold higher than annopurpuricins B-E. This optimised method identified and quantified five annopurpuricins, highly bioactive molecules, in A. purpurea root. The fingerprint of the dichloromethane extracts of A. purpurea was obtained at 210 nm. The results analysis allowed to quantify annopurpuricins A-E that are present in different collection batches of medium polarity extracts. After data analysis, annopurpuricin A could be establish as the metabolite marker of the root of the species.

Cytotoxic Acetogenins from the Roots of Annona purpurea.

Annona purpurea, known in Mexico as “cabeza de negro” or “ilama”, belongs to the Annonaceae family. Its roots are employed in folk medicine in several regions of Mexico. Taking that information into account, a chemical and biological analysis of the components present in the roots of this species was proposed. Our results demonstrated that the dichloromethane (DCM) extract was exclusively constituted by a mixture of five new acetogenins named annopurpuricins A–E (1–5). These compounds have an aliphatic chain of 37 carbons with a terminal α,β unsaturated γ-lactone. Compounds 1 and 2 belong to the adjacent bis-THF (tetrahydrofuran) α-monohydroxylated type, while compounds 3 and 4 belong to the adjacent bis-THF α,α’-dihydroxylated type; only compound 5 possesses a bis-epoxide system. Complete structure analysis was carried out by spectroscopy and chemical methods. All compounds were evaluated for their antiproliferative activity on three human tumor cell lines (MSTO-211H, HeLa and HepG2). Compounds 1–4 inhibited significantly the growth of HeLa and HepG2 cells, showing GI50 values in the low/subnanomolar range, while 5 was completely ineffective under the tested conditions. The investigation of the mechanism of action responsible for cytotoxicity revealed for the most interesting compound 1 the ability to block the complex I activity on isolated rat liver mitochondria (RLM).

Spatio-Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity.

Annona purpurea grows in the areas of low elevation in deciduous forests of Mexico, those areas have marked rainy and dry seasons. This species produces more than 30 bioactive alkaloids that could have potential in the control of phytopathogens. This research provides data on the variation of the content and number of alkaloids during an annual cycle and the associated inhibitory potential of the compounds against three phytopathogenic fungi. For one year, alkaloidal extracts of stems and leaves were obtained every two months. The extract profiles were determined by gas chromatography with tandem mass spectrometry and their antifungal activity was examined in vitro. The alkaloids, annomontine and oxopurpureine, obtained from the roots and leaves, respectively, were also evaluated individually. The yields, profiles and activities of the extracts, as well as the abundance of annomontine and oxopurpureine in the extracts, were contrasted with the seasonality and phenological phases of the plant. The data indicate that the alkaloid content was higher at the height of the dry season. High yields also occurred during flowering. The strongest inhibitory effect was obtained from the root extracts during the last month of dry season. This finding seems to be explained by the higher chemodiversity of alkaloids in extracts from this season. Annomontine and oxopurpureine inhibited all three phytopathogens; however, they were not solely responsible for the activity of A. purpurea.

The norpurpureine alkaloid from Annona purpurea inhibits human platelet activation in vitro

BackgroundThe leaves of Annona purpurea have yielded several alkaloids with anti-aggregation activities against rabbit platelets. This is promising in the search for agents that might act against platelets and reduce the incidence of cardiovascular diseases. Since significant differences in platelet function have been reported between human and animal platelets, a study focusing on the effect of A. purpurea extracts against human platelet activation is necessary.MethodsThe compounds in an A. purpurea ethanolic extract underwent bio-guided fractionation and were used for in vitro human platelet aggregation assays to isolate the compounds with anti-platelet activity. The bioactive compounds were identified by spectroscopic analysis. Additional platelet studies were performed to characterize their action as inhibitors of human platelet activation.ResultsThe benzylisoquinoline alkaloid norpurpureine was identified as the major anti-platelet compound. The IC50 for norpurpureine was 80 μM against platelets when stimulated with adenosine 5′-diphosphate (ADP), collagen and thrombin. It was pharmacologically effective from 20 to 220 μM. Norpurpureine (220 μM) exhibited its in vitro effectiveness in samples from 30 healthy human donors who did not take any drugs during the 2 weeks prior to the collection. Norpurpureine also gradually inhibited granule secretion and adhesion of activated platelets to immobilized fibrinogen. At the intra-platelet level, norpurpureine prevented agonist-stimulated calcium mobilization and cAMP reduction. Structure–activity relationship analysis indicates that the lack of a methyl group at the nitrogen seems to be key in the ability of the compound to interact with its molecular target.ConclusionNorpurpureine displays a promising in vitro pharmacological profile as an inhibitor of human platelet activation. Its molecular target could be a common effector between Ca2+ and cAMP signaling, such as the PLC-PKC-Ca2+ pathway and PDEs. This needs further evaluation at the protein isoform level.

Cyclopurpuracin, a cyclopeptide from Annona purpurea seeds

From a 60% hydroalcoholic extract of the seeds of Annona purpurea, a novel cyclooctapeptide, cyclopurpuracin (1), or cyclo(-Pro1-Gly2-Phe3-ILe4-Gly5-Ser6-Pro7-Val8-), has been isolated. The structure of cyclopurpuracin (1) was determined by de novo sequencing based on MS/MS spectra and 1D and 2D NMR techniques (1H, 13C, HSQC, HMBC, COSY and ROESY).

OVERCOMING SEED DORMANCY IN Annona macroprophyllata AND Annona purpureaUSING PLANT GROWTH REGULATORS

ABSTRACT Some Annonaceae seeds are known to exhibit dormancy mechanisms ranging from possible seed coat impermeability to physiological dormancy. Thus, the aim of this study was to evaluate the effects of gibberellin (GA) GA3 and GA4+7 + benzyladenine (GA4+7 + BA) application in seeds of Annona macroprophyllata Donn. Sm (papausa) and Annona purpurea Moc. & Sessé ex Dunal (chincuya). The experiment was performed by the application of GA3 and GA4+7 + BA on seeds in concentrations of 0, 200, 400, 500, 600, 800 and 1000 mg L-1. The regulators broke the dormancy of both species. However, application of the GA4+7 + BA mixture had more significant results, with greater increases in germination in A. macroprophyllata than in A. purpurea. Treatments that promoted the highest germinations were GA4+7 + BA at a concentration of 200 mg L-1 for A. macroprophyllata (77%) and 200 mg L-1 of GA4+7 + BA and 500 mg L-1 of GA3 for A. purpurea (30% and 29%, respectively). Rate index, mean time and frequency of germination were distinct for both species and both treatments. Although both GA3 and GA4+7 + BA promote germination, the GA4+7 + BA mixture was more effective than GA3 to overcoming seed dormancy of both species, A. purpurea has a harder dormancy than A. macroprophyllata

Growth, Phenolic Content and Antioxidant Activity in Chincuya (Annona purpurea Moc & Sesse ex Dunal) Cultivated with Vermicompost and Phosphate Rock

ABSTRACTThe aim of this investigation was to determine the effect of vermicompost and phosphate rock on plant growth, total phenols, flavonoids, flavanones, and antioxidant activity in Annona purpurea Moc & Sesse ex Dunal leaves. Annona purpurea seedlings were planted according to factorial 32 experimental design with nine repetitions. The factors were vermicompost (0, 50, and 100 g plant−1) and phosphate rock (0 and 10 g plant−1). Plant height, stem diameter, number of leaves, and chorophyll content were determined one month after application of the different treatments and total phenols, flavonols, flavanones, total flavonoids, and 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging activity in dry leaves after 4 months. Plant height and stem diameter increased by phosphate rock, but not by vermicompost. Total phenols in leaves decreased by vermicompost. Flavonol content decreased by rock phosphate, whereas flavanones increased by vermicompost. Antioxidant activity decreased by vermicompost addition.

Study of the carotenoid composition in membrillo, guanabana toreta, jobo and mamey fruits

Introduction. Many tropical fruits have great health potential due to the possible presence of bioactive phytochemicals. Natural food composition databases are very important sources of information relative to natural food biodiversity and nutritional properties. The objective of this study was to report for the first time on the native carotenoid composition of the fruit of four tropical species from Panama. Materials and methods. Fully mature fruit were collected in Panama and analyzed by HPLC-DAD-APCI-MS, after carotenoid extraction with acetone. Results and discussion. The carotenoid composition had never been previously reported for two of the investigated fruits, membrillo (Gustavia superba ) and guanabana toreta (Annona purpurea ). In membrillo, 5 different carotenoids were detected; the content of total carotenoids was 318.6 μ g g-1 fresh weight (fw), with β -carotene showing a relative abundance of 75.3%. In guanabana toreta, 11 different carotenoids were detected; the total carotenoid content was 48.3 μ g g-1 fw, with β -carotene and zeaxanthin showing a relative abundance of 26.9% and 27.5%, respectively. In jobo (Spondias mombin ), 11 different carotenoids were detected; the total carotenoid content was 45.8 μ g g-1 fw, with β -cryptoxanthin, α -carotene and β -carotene showing a relative abundance of 25.4%, 10.5% and 8.5%, respectively. In mamey (Mammea americana ), 16 different carotenoids were detected; the total carotenoid content was 145.2 μ g g-1 fw; in particular, 10 different violaxanthin fatty acid diesters, of both cis and trans isomers, were determined. Conclusion. The consumption of the fruit studied should be promoted both locally and abroad, because of the reported presence of these health-promoting phytochemicals.

Water uptake by Annona diversifolia Saff. and A. purpurea Moc. & sessé ex dunal seeds (Annonaceae)

Annonaceae seeds are known by presenting dormancy mechanisms, whose reports ranging from coating impermeable to the physiological dormancy. By this way, the present study aimed to evaluate water uptake in Annona diversifolia Saff and Annona purpurea Moc & Sessé ex Dunal seeds. For this study, seeds were placed under immersion in distilled water, and used four replicates of 25 seeds of each species, which were weighed during the 480 hours that were immersed. To determine the place of purchase of water, Annona diversifolia seeds were sealed with paraffin at different locations. Based on the results, seeds from both species reached the phases I and II of water uptake, which indicates they are not hard; however, germination (Phase III) was not reached. Annona diversifolia seeds completed Phase I with, 50h and Annona purpurea with 70h from imbibitions begin, which shows that even slowly, water is acquire.

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

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.

ChemInform Abstract: Two New 7-Dehydroaporphine Alkaloids and Antiplatelet Action Aporphines from the Leaves of Annona purpurea.

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Screening of plant extracts for antiprotozoal and cytotoxic activities

Methanolic and aqueous extracts derived from 43 plant species, selected either from ethnobotanical or chemotaxonomical data, were screened for their antiprotozoal activity against Leishmania donovani and Trypanosoma brucei brucei. The cytotoxic activity against KB cells was also determined. Eight extracts had IC 50 values of less than 10 μg/ml against Leishmania donovani. The most active was Triclisia patens with an IC 50 value of 1.5 μg/ml against Leishmania donovani. Annona purpurea and Alstonia macrophylla had IC 50 values below 10 μg/ml against Trypanosoma brucei brucei. Annona purpurea was the most cytotoxic against KB cells.

Annonaceous acetogenins: Naturally occurring inhibitors of ATP synthesis and photosystem II in spinach chloroplasts

The effects of squamocin (1), bullatacin (2) and motrilin (3), 3 bis‐tetrahydrofuran Annonaceous acetogenins, isolated from Annona purpurea (Annonaceae), were investigated on several photosynthetic activities in spinach thylakoids. The results indicated that compounds 1–3 significantly inhibited both ATP synthesis and uncoupled electron transport. In addition, they enhanced light‐activated Mg2+‐ATPase, and basal electron flow. Therefore, acetogenins 1–3 behave as uncouplers and Hill reaction inhibitors. Natural products 1–3 did not affect photosystem I (PSI) activity but they inhibited photosystem II (PSII) electron flow. The study of the partial PSII reactions from H2O to DCPIPox, H2O to SiMo and diphenylcarbazide to DCPIP established that the site of inhibition was at the oxygen‐evolving complex (OEC). Chlorophyll a fluorescence measurements confirmed the behavior of the Annonaceous acetogenins as water‐splitting enzyme inhibitors.

Purpuracenin: a new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Annona purpurea.

Purpuracenin, a novel cytotoxic acetogenin and annaglaucin, a known compound, were isolated from the seeds of Annona purpurea. Their structures were elucidated by a combination of chemical and spectral methods including MS and NMR spectral measurements. The absolute configurations of both compounds are presented. The new compound and annoglaucin exhibited potent cytotoxic activity in vitro against six human solid tumor cell lines.