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1.
Braz. j. biol ; 83: e246455, 2023. tab, graf
Artigo em Inglês | MEDLINE, LILACS, VETINDEX | ID: biblio-1278524

RESUMO

Abstract The inheritance of the seedless fruit characteristic of Annona squamosa has not yet been explained. Molecular techniques may aid breeding programs, mainly in the assisted selection of the target gene. The INO gene may be related to seed development in these fruits. The objective of the present paper was to investigate the inheritance of seedlessness in the 'Brazilian seedless' sugar apple and INO gene conservation in Annona squamosa and Annona cherimola x Annona squamosa genotypes by assessing their homology with the INO database genes. The F1 generation was obtained by crossing the mutant 'Brazilian seedless' (male genitor) (P1) with the wild-type A. squamosa with seeds (M1 and M2, female genitors). The INO gene was studied in mutant and wild-type A. squamosa (P1, M1, M2 and M3) and in the Gefner atemoya (A. cherimola x A. squamosa) (M4) cultivar. The DNA was extracted from young leaves, and four sets of specific primers flanking the INO gene were amplified. The seedless characteristic was identified as stenospermatic in the fruits of parental P1, suggesting monogenic inheritance with complete dominance. High sequence similarity of the INO gene amplifications in the sugar apple accessions (M1, M2, M3) and the atemoya cultivar Gefner (M4) reinforces the hypothesis of their conservation.


Resumo A herança da característica de fruto sem sementes de Annona squamosa ainda não foi esclarecida. Técnicas moleculares podem auxiliar em programas de melhoramento, principalmente na seleção assistida do gene de interesse. O gene INO pode estar relacionado ao desenvolvimento da semente dessas frutas. O objetivo foi investigar a herança da ausência de sementes em Annona squamosa e a conservação do gene INO nos genótipos Annona squamosa e Annona cherimola x Annona squamosa avaliando sua homologia com banco de dados de genes INO. A geração F1 foi obtida pelo cruzamento do mutante 'Brazilian seedless' (genitor masculino) (P1) com o tipo selvagem com sementes (A. squamosa) (M1 e M2, genitores femininos). O gene INO foi estudado em A. squamosa, mutante e selvagem (P1, M1, M2 e M3) e na cultivar Gefner atemoya (A. cherimola x A. squamosa) (M4). O DNA foi extraído de folhas jovens, e quatro conjuntos de primers específicos flanqueando o gene INO foram amplificados. A característica sem sementes foi identificada como estenospermática nos frutos do parental P1, sugerindo herança monogênica com dominância completa. A alta similaridade de sequência das amplificações do gene INO nos acessos de pinha (M1, M2, M3) e na cultivar de atemóia Gefner (M4) reforça a hipótese de sua conservação.


Assuntos
Annonaceae , Annona/genética , Sementes/genética , Brasil , Melhoramento Vegetal , Frutas/genética
2.
Oxid Med Cell Longev ; 2022: 8918966, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-35340209

RESUMO

Parkinson's disease (PD) is an age-related neurodegenerative disorder characterized by progressive deterioration of motor function and loss of dopaminergic neurons in the substantia nigra. Although PD is more common in people over 60 years old, people with young-onset PD tend to increase recently. Up to now, there is no cure for PD; therapies mainly focus on reducing symptoms and improving patient quality of life. Thus, the requirement of exploring new medications is needed. There is a strong relationship between oxidative stress and PD. Therefore, antioxidant compounds have been considered as a novel therapy for PD. In this study, we indicated a new potential candidate for PD treatment, rumdul fruit (Sphaerocoryne affinis-a member of the Annonaceae family), due to evaluating its activities on the fly model of Parkinson. Our experimental results showed that rumdul fruit water extract (RFWE) has a strong antioxidant capacity with IC50 value in DPPH assay which was 85.62 ± 1.05 µg/mL. The use of RFWE at concentrations of 3, 6, and 12 mg/mL could strongly ameliorate the locomotor disabilities and dopaminergic neuron degeneration. Although the RFWE at high concentrations like 12 mg/mL and 18 mg/mL could induce some side effects on fly development and viability, our data strongly demonstrated that RFWE effectively rescued PD phenotypes on the fly model. Although component in the plant extract, as well as the molecular mechanism helping to recover the phenotype, has not been elucidated yet, the research contributed strong scientific evidence for further research on applying rumdul as a novel natural source for PD treatment.


Assuntos
Annonaceae , Doença de Parkinson , Antioxidantes/farmacologia , Antioxidantes/uso terapêutico , Neurônios Dopaminérgicos , Humanos , Doença de Parkinson/tratamento farmacológico , Qualidade de Vida
3.
Molecules ; 27(3)2022 Jan 28.
Artigo em Inglês | MEDLINE | ID: mdl-35164158

RESUMO

As part of our continuous studies involving the prospection of natural products from Brazilian flora aiming at the discovery of prototypes for the development of new antiparasitic drugs, the present study describes the isolation of two natural acetylene acetogenins, (2S,3R,4R)-3-hydroxy-4-methyl-2-(n-eicos-11'-yn-19'-enyl)butanolide (1) and (2S,3R,4R)-3-hydroxy-4-methyl-2-(n-eicos-11'-ynyl)butanolide (2), from the seeds of Porcelia macrocarpa (Warm.) R.E. Fries (Annonaceae). Using an ex-vivo assay, compound 1 showed an IC50 value of 29.9 µM against the intracellular amastigote forms of Leishmania (L.) infantum, whereas compound 2 was inactive. These results suggested that the terminal double bond plays an important role in the activity. This effect was also observed for the semisynthetic acetylated (1a and 2a) and eliminated (1b and 2b) derivatives, since only compounds containing a double bond at C-19 displayed activity, resulting in IC50 values of 43.3 µM (1a) and 23.1 µM (1b). In order to evaluate the effect of the triple bond in the antileishmanial potential, the mixture of compounds 1 + 2 was subjected to catalytic hydrogenation to afford a compound 3 containing a saturated side chain. The antiparasitic assays performed with compound 3, acetylated (3a), and eliminated (3b) derivatives confirmed the lack of activity. Furthermore, an in-silico study using the SwissADME online platform was performed to bioactive compounds 1, 1a, and 1b in order to investigate their physicochemical parameters, pharmacokinetics, and drug-likeness. Despite the reduced effect against amastigote forms of the parasite to the purified compounds, different mixtures of compounds 1 + 2, 1a + 2a, and 1b + 2b were prepared and exhibited IC50 values ranging from 7.9 to 38.4 µM, with no toxicity for NCTC mammalian cells (CC50 > 200 µM). Selectivity indexes to these mixtures ranged from >5.2 to >25.3. The obtained results indicate that seeds of Porcelia macrocarpa are a promising source of interesting prototypes for further modifications aiming at the discovery of new antileishmanial drugs.


Assuntos
Acetogeninas/farmacologia , Acetileno/farmacologia , Annonaceae/química , Antiprotozoários/farmacologia , Leishmania/efeitos dos fármacos , Acetogeninas/química , Acetileno/análogos & derivados , Antiprotozoários/química , Humanos , Leishmaniose/tratamento farmacológico , Sementes/química
4.
Fitoterapia ; 157: 105119, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-34979257

RESUMO

Four rare isotachin-derived, isotachins E-H (1-4), together with two known biogenetically related isotachin derivatives (5 and 6) were isolated from the solid rice fermentation of a fungus Penicillium tanzanicum ZY-5 obtained from a medicinal plant Dasymaschalon rostratum collected from the Changjiang County, Hainan Province, China. Their structures were elucidated using comprehensive spectroscopic methods. The single-crystal X-ray diffraction of compound 5 was determined. Compounds 1-4 have a trans-3-(methylthio)-acrylic acid fragment, which are rare in nature. The inhibitory activities of all compounds against the nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro were evaluated.


Assuntos
Annonaceae/microbiologia , Metacrilatos/química , Penicillium/química , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Cristalografia por Raios X , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Metacrilatos/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/metabolismo , Penicillium/isolamento & purificação , Células RAW 264.7 , Espectrofotometria Infravermelho
5.
Biochem Pharmacol ; 195: 114825, 2022 01.
Artigo em Inglês | MEDLINE | ID: mdl-34762841

RESUMO

Specialized pro-resolving mediators (SPMs) comprise lipid mediators (LMs) produced from polyunsaturated fatty acids (PUFAs) via stereoselective oxygenation particularly involving 12/15-lipoxygenases (LOXs). In contrast to pro-inflammatory LMs such as leukotrienes formed by 5-LOX and prostaglandins formed by cyclooxygenases, the SPMs have anti-inflammatory and inflammation-resolving properties. Although glucocorticoids and non-steroidal anti-inflammatory drugs (NSAIDs) that block prostaglandin production are still prime therapeutics for inflammation-related diseases despite severe side effects, novel concepts focus on SPMs as immunoresolvents for anti-inflammatory pharmacotherapy. Here, we studied the natural chalcone MF-14 and the corresponding dihydrochalcone MF-15 from Melodorum fruticosum, for modulating the biosynthesis of LM including leukotrienes, prostaglandins, SPM and their 12/15-LOX-derived precursors in human monocyte-derived macrophage (MDM) M1- and M2-like phenotypes. In MDM challenged with Staphylococcus aureus-derived exotoxins both compounds (10 µM) significantly suppressed 5-LOX product formation but increased the biosynthesis of 12/15-LOX products, especially in M2-MDM. Intriguingly, in resting M2-MDM, MF-14 and MF-15 strikingly evoked generation of 12/15-LOX products and of SPMs from liberated PUFAs, along with translocation of 15-LOX-1 to membranous compartments. Enhanced 12/15-LOX product formation by the chalcones was evident also when exogenous PUFAs were supplied, excluding increased substrate supply as sole underlying mechanism. Rather, MF-14 and MF-15 stimulate the activity of 15-LOX-1, supported by experiments with HEK293 cells transfected with either 5-LOX, 15-LOX-1 or 15-LOX-2. Together, the natural chalcone MF-14 and the dihydrochalcone MF-15 favorably modulate LM biosynthesis in human macrophages by suppressing pro-inflammatory leukotrienes but stimulating formation of SPMs by differential interference with 5-LOX and 15-LOX-1.


Assuntos
Araquidonato 12-Lipoxigenase/metabolismo , Araquidonato 15-Lipoxigenase/metabolismo , Chalcona/farmacologia , Leucotrienos/metabolismo , Macrófagos/efeitos dos fármacos , Prostaglandinas/metabolismo , Adulto , Annonaceae/química , Araquidonato 12-Lipoxigenase/genética , Araquidonato 15-Lipoxigenase/genética , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Chalcona/química , Chalconas/química , Chalconas/farmacologia , Células HEK293 , Humanos , Ativação de Macrófagos/efeitos dos fármacos , Macrófagos/classificação , Macrófagos/metabolismo , Estrutura Molecular , Extratos Vegetais/farmacologia
6.
Nat Prod Res ; 36(2): 553-559, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-32668989

RESUMO

From the ethyl acetate extract of the stems of Miliusa velutina, seven compounds (1-7) were isolated, including two new compounds such as mivelutina A acid (1), mivelutina B acid (2) and one known compound mivelutina B methyl ester (3). For this NMR data were not known previously. Their relative structures were elucidated based on NMR spectroscopic analysis. The absolute configuartions were determined based on DFT calculations of 13C chemical shifts. All of the seven compounds were screened for their in vitro cytotoxic activities against HepG2 cell line using the SRB assay. Epoxyconiferyl alcohol (7) showed the highest potential for the cytotoxicity of cancer cell lines HepG2 with the IC50 values of 95.94 µg/mL (527 µM).


Assuntos
Annonaceae , Antineoplásicos Fitogênicos , Sesquiterpenos , Antineoplásicos Fitogênicos/farmacologia , Células Hep G2 , Humanos , Estrutura Molecular , Sesquiterpenos/farmacologia
7.
Nat Prod Res ; 36(8): 2105-2111, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-33565887

RESUMO

The root and stem bark essential oils from Isolona dewevrei (Annonaceae), growing wild in Côte d'Ivoire, were investigated for the first time, using a combination of chromatographic [CC, GC(RI)] and spectroscopic [MS, 13C-NMR] techniques. A new natural germacrone was isolated by repetitive column chromatography carried out on a stem bark oil sample. Its structure was elucidated as germacra-1(10),4(15),5-trien-8-one by 1 D, 2 D-NMR and QTOF-MS. Ninety-six components accounting for 95.5 ± 0.8% and 95.8 ± 1.0%, respectively, for the root and stem bark essential oil samples were identified. The major compounds of root oil were cyperene (19.7 ± 1.6%) and camphene (10.1 ± 2.1%), followed by 5-isopentenylindole (6.4 ± 2.4%), ß-elemene (3.9 ± 0.3%), (Z)-α-bisabolene (3.2 ± 1.2%) and γ-gurjunene (3.2 ± 0.3%). The stem bark oil was also dominated by cyperene (29.2 ± 4.1%), followed by ß-elemene (6.2 ± 1.1%), (Z)-α-bisabolene (3.8 ± 1.0%), (E)-ß-caryophyllene (3.3 ± 0.7%) and α-copaene (2.8 ± 1.1%).


Assuntos
Annonaceae , Óleos Voláteis , Annonaceae/química , Costa do Marfim , Óleos Voláteis/química , Casca de Planta/química , Folhas de Planta/química , Óleos Vegetais/química , Sesquiterpenos de Germacrano
8.
Trop Anim Health Prod ; 54(1): 2, 2021 Dec 08.
Artigo em Inglês | MEDLINE | ID: mdl-34881400

RESUMO

Haemonchosis is a gastrointestinal parasitic disease of economic importance in ruminants especially sheep and goats. In view of the rising costs of conventional veterinary anthelmintics and the development of resistance by Haemonchus contortus, there is a need to develop alternative ethnoveterinary therapies for the treatment and management of Haemonchosis. This study investigated the anthelmintic activity of Dennettia tripetala G. Baker (Annonaceae) fruits against Haemonchus contortus in red Sokoto goats. The maximum tolerated dose was determined in adult albino rats administered, 3000, 4000, and 5000 mg/kg body weight of the crude methanol extract (CME) fraction, and observed over a period of 48 h for signs of toxicity and mortality. The in vivo anthelmintic activity was evaluated using 20 kids infected with H. contortus and randomly allocated into 5 groups (1, 2, 3, 4, and 5). Kids in groups 1, 2, and 3 were treated with CME at doses of 1250, 2500, and 5000 mg/kg respectively for 3 consecutive days per os. Groups 4 and 5 were treated with albendazole (7.5 mg/kg) once and distilled water (5 ml) respectively and served as treated and untreated controls. Blood samples were collected for haematology. The maximum tolerated dose of the CME of D. tripetala did not produce observable signs of toxicity or death in all the rats given up to 5000 mg/kg. There was significant (P < 0.05) reduction in faecal egg count by CME at doses of 1250 mg/kg (91.6%), 2500 mg/kg (98.5%), and 5000 mg/kg (100%) at day 14 post-treatment. The total plasma protein (TPP) and FAMACHA© scoring values were significantly improved (P < 0.05) in the treated groups. These results indicate that methanol extract and fractions of D. tripetala fruits possess beneficial anthelmintic activity against H. contortus and may be a suitable alternative anthelmintic candidate for the control of haemonchosis in goats.


Assuntos
Annonaceae , Anti-Helmínticos , Doenças das Cabras , Hemoncose , Haemonchus , Doenças dos Roedores , Doenças dos Ovinos , Animais , Anti-Helmínticos/uso terapêutico , Fezes , Frutas , Doenças das Cabras/tratamento farmacológico , Cabras , Hemoncose/tratamento farmacológico , Hemoncose/veterinária , Metanol/uso terapêutico , Nigéria , Contagem de Ovos de Parasitas/veterinária , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Ratos , Ovinos , Doenças dos Ovinos/tratamento farmacológico
9.
Int J Mol Sci ; 22(22)2021 Nov 09.
Artigo em Inglês | MEDLINE | ID: mdl-34830022

RESUMO

The present work involves a systematic review of the chemical composition and biological effects of essential oils from the Annonaceae species collected in Brazil from 2011 to 2021. Annonaceae is one of the most important botanical families in Brazil, as some species have economic value in the market as local and international fruit. In addition, the species have useful applications in several areas-for instance, as raw materials for use in cosmetics and perfumery and as medicinal plants. In folk medicine, species such as Annona glabra L. and Xylopia sericea A. St.-Hil. are used to treat diseases such as rheumatism and malaria. The species of Annonaceae are an important source of essential oils and are rich in compounds belonging to the classes of mono and sesquiterpenes; of these compounds, α-pinene, ß-pinene, limonene, (E)-caryophyllene, bicyclogermacrene, caryophyllene oxide, germacrene D, spathulenol, and ß-elemene are the most abundant. The antimicrobial, anti-inflammatory, antileishmania, antioxidant, antiproliferative, cytotoxic, larvicidal, trypanocidal, and antimalarial activities of essential oils from the Annonaceae species in Brazil have been described in previous research, with the most studies on this topic being related to their antiproliferative or cytotoxic activities. In some studies, it was observed that the biological activity reported for these essential oils was superior to that of drugs available on the market, as is the case of the essential oil of the species Guatteria punctata (Aubl.) R. A. Howard., which showed a trypanocidal effect that was 34 times stronger than that of the reference drug benznidazol.


Assuntos
Annonaceae/química , Óleos Voláteis/química , Compostos Fitoquímicos/química , Antibacterianos/química , Antibacterianos/uso terapêutico , Brasil , Humanos , Óleos Voláteis/uso terapêutico , Folhas de Planta/química , Sesquiterpenos Policíclicos/química , Sesquiterpenos/química , Sesquiterpenos de Germacrano/química
10.
J Nat Prod ; 84(12): 3117-3121, 2021 12 24.
Artigo em Inglês | MEDLINE | ID: mdl-34812640

RESUMO

Two unusual phenanthrene derivatives related to aporphine alkaloids, artapilosines A (1) and B (2), as well as two biogenetically related known aporphine alkaloids, (-)-anonaine (3) and (-)-N-acetylanonaine (4), were separated and purified from Artabotrys pilosus. Artapilosine A (1) is the first compound representative of a new class of phenanthrene derivatives having an unprecedented carbon skeleton, in which the six-membered nitrogen-containing heterocyclic structure in a typical aporphine alkaloid was substituted with a unique five-membered carbocyclic ring. This is the first report of the formation of a carbon-carbon bond between C-5 and C-6a in 1 with the loss of the nitrogen atom N-6 in the classic aporphine alkaloid. Artapilosine B (2) is a novel phenanthrene derivative having a hydroxyethyl as a substituent on the phenanthrene ring. Their chemical structures as well as absolute configurations were determined based on analysis of spectroscopic data. Additionally, the potential anti-HIV activities of all isolates 1-4 were appraised. Artapilosines A (1) and B (2) showed notable anti-HIV reverse transcriptase affects, with EC50 values of 20.93 and 125.29 nM, respectively. These results suggested that the discovery of these novel phenanthrene derivatives from A. pilosus with remarkable anti-HIV effects could be essentially important for the researching and developing of new anti-HIV agents.


Assuntos
Annonaceae/química , Aporfinas/isolamento & purificação , Fenantrenos/química , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Aporfinas/química , Humanos , Estrutura Molecular
11.
Molecules ; 26(20)2021 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-34684809

RESUMO

The chemical variability and the in vitro anti-inflammatory activity of the leaf essential oil from Ivorian Isolona dewevrei were investigated for the first time. Forty-seven oil samples were analyzed using a combination of CC, GC(RI), GC-MS and 13C-NMR, thus leading to the identification of 113 constituents (90.8-98.9%). As the main components varied drastically from sample to sample, the 47 oil compositions were submitted to hierarchical cluster and principal components analyses. Three distinct groups, each divided into two subgroups, were evidenced. Subgroup I-A was dominated by (Z)-ß-ocimene, ß-eudesmol, germacrene D and (E)-ß-ocimene, while (10ßH)-1ß,8ß-oxido-cadina-4-ene, santalenone, trans-α-bergamotene and trans-ß-bergamotene were the main compounds of Subgroup I-B. The prevalent constituents of Subgroup II-A were germacrene B, (E)-ß-caryophyllene, (5αH,10ßMe)-6,12-oxido-elema-1,3,6,11(12)-tetraene and γ-elemene. Subgroup II-B displayed germacrene B, germacrene D and (Z)-ß-ocimene as the majority compounds. Germacrene D was the most abundant constituent of Group III, followed in Subgroup III-A by (E)-ß-caryophyllene, (10ßH)-1ß,8ß-oxido-cadina-4-ene, germacrene D-8-one, and then in Subgroup III-B by (Z)-ß-ocimene and (E)-ß-ocimene. The observed qualitative and quantitative chemical variability was probably due to combined factors, mostly phenology and season, then harvest site to a lesser extent. The lipoxygenase inhibition by a leaf oil sample was also evaluated. The oil IC50 (0.020 ± 0.005 mg/mL) was slightly higher than the non-competitive lipoxygenase inhibitor NDGA IC50 (0.013 ± 0.003 mg/mL), suggesting a significant in vitro anti-inflammatory potential.


Assuntos
Annonaceae/química , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Óleos Vegetais/química , Óleos Vegetais/farmacologia , Anti-Inflamatórios/isolamento & purificação , Costa do Marfim , Avaliação Pré-Clínica de Medicamentos , Cromatografia Gasosa-Espectrometria de Massas , Técnicas In Vitro , Lipoxigenase/efeitos dos fármacos , Inibidores de Lipoxigenase/química , Inibidores de Lipoxigenase/isolamento & purificação , Inibidores de Lipoxigenase/farmacologia , Espectroscopia de Ressonância Magnética , Óleos Voláteis/classificação , Folhas de Planta/química , Óleos Vegetais/classificação , Plantas Medicinais/química , Soja/enzimologia
12.
Fitoterapia ; 155: 105036, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34536535

RESUMO

Two novel aporphine-derived alkaloids, aporaloids A and B (1 and 2), together with eight known biogenetically related alkaloids (3-10), two known isoquinoline alkaloids (3 and 4), and six known aporphinoid alkaloids (5-10) were isolated from the stems of Fissistigma glaucescens. Their structures were elucidated using comprehensive spectroscopic methods. Compounds 1 and 2 represent the rare example of a six-membered lactone ring aporphine-derived alkaloids from natural products. The inhibitory activities of all compounds against four cancer cell lines were evaluated. Aporaloids A and B (1 and 2) showed broad spectrum cytotoxic activities.


Assuntos
Annonaceae/química , Antineoplásicos Fitogênicos/farmacologia , Aporfinas/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Aporfinas/isolamento & purificação , Linhagem Celular Tumoral , China , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Caules de Planta/química
13.
Chem Biodivers ; 18(10): e2100544, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34405534

RESUMO

Annona emarginata (Annonaceae) has two morphological variations (A. emarginata 'mirim' and A. emarginata 'terra-fria'). The species has agricultural value and produces specialized metabolites of pharmacological interest. The objective of this work was to analyze whether chemical and morphological differences contribute to differentiate A. emarginata 'terra-fria' from A. emarginata 'mirim', as chemophenetic variations of A. emarginata. The analysis of chemical compounds was based on the quantification, profile of root alkaloids and on the leaves volatile profile, together with morphometric analyses of the leaf blade. The samples were collected in three phenological stages (flowering, fruiting, and vegetative) at two places in São Paulo, Brazil. Differences in the composition of the alkaloid profile and leaf volatiles (in both places and in the three phenological stages) allowed us to separate the two morphotypes by multivariate statistical analysis. These differences agreed with the leaf blade morphology and flower color. This first chemophenetic report of A. emarginata demonstrates that, in addition to morphological variations, the specialized metabolism of roots and leaves can be phytochemical characters, which suggest the existence of at least morphochemotypes of A. emarginata.


Assuntos
Annonaceae/química , Compostos Fitoquímicos/análise , Brasil , Flores/química , Frutas/química , Folhas de Planta/química
14.
Molecules ; 26(12)2021 Jun 18.
Artigo em Inglês | MEDLINE | ID: mdl-34207059

RESUMO

Diclinanona calycina R. E. Fries popularly known as "envira", is a species of the Annonaceae family endemic to Brazil. In our ongoing search for bioactive compounds from Annonaceae Amazon plants, the bark of D. calycina was investigated by classical chromatography techniques that yielded thirteen compounds (alkaloids and flavonoids) described for the first time in D. calycina as well as in the genus Diclinanona. The structure of these isolated compounds were established by extensive analysis using 1D/2D-NMR spectroscopy in combination with MS. The isolated alkaloids were identified as belonging to the subclasses: simple isoquinoline, thalifoline (1); aporphine, anonaine (2); oxoaporphine, liriodenine (3); benzyltetrahydroisoquinolines, (S)-(+)-reticuline (4); dehydro-oxonorreticuline (3,4-dihydro-7-hydroxy-6-methoxy-1-isoquinolinyl)(3-hydroxy-4-methoxyphenyl)-methanone) (5); (+)-1S,2R-reticuline Nß-oxide (6); and (+)-1S,2S-reticuline Nα-oxide (7); tetrahydroprotoberberine, coreximine (8); and pavine, bisnorargemonine (9). While the flavonoids belong to the benzylated dihydroflavones, isochamanetin (10), dichamanetin (11), and a mixture of uvarinol (12) and isouvarinol (13). Compound 5 is described for the first time in the literature as a natural product. The cytotoxic activity of the main isolated compounds was evaluated against cancer and non-cancerous cell lines. Among the tested compounds, the most promising results were found for the benzylated dihydroflavones dichamanetin (10), and the mixture of uvarinol (12) and isouvarinol (13), which presented moderate cytotoxic activity against the tested cancer cell lines (<20.0 µg·mL-1) and low cytotoxicity against the non-cancerous cell line MRC-5 (>25.0 µg·mL-1). Dichamanetin (11) showed cytotoxic activity against HL-60 and HCT116 with IC50 values of 15.78 µg·mL-1 (33.70 µmol·L-1) and 18.99 µg·mL-1 (40.56 µmol·L-1), respectively while the mixture of uvarinol (12) and isouvarinol (13) demonstrated cytotoxic activity against HL-60, with an IC50 value of 9.74 µg·mL-1, and HCT116, with an IC50 value of 17.31 µg·mL-1. These cytotoxic activities can be attributed to the presence of one or more hydroxybenzyl groups present in these molecules as well as the position in which these groups are linked. The cytotoxic activities of reticuline, anonaine and liriodenine have been previously established, with liriodenine being the most potent compound.


Assuntos
Alcaloides/química , Annonaceae/química , Flavonas/química , Isoquinolinas/química , Casca de Planta/química , Alcaloides/farmacologia , Aporfinas/química , Aporfinas/farmacologia , Brasil , Linhagem Celular Tumoral , Dioxóis/química , Dioxóis/farmacologia , Flavanonas/farmacologia , Flavonas/farmacologia , Células HCT116 , Células HL-60 , Células Hep G2 , Humanos , Isoquinolinas/farmacologia , Células MCF-7 , Extratos Vegetais , Folhas de Planta/química
15.
Neotrop Entomol ; 50(4): 662-672, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-34184236

RESUMO

The poultry red mite Dermanyssus gallinae (De Geer) is the most important haematophagous ectoparasite in the poultry industry. The use of synthetic acaricides for this control is presenting risks related to human food. In this sense, plant secondary metabolites are promising for controlling this pest. Thus, this study aimed to evaluate the acaricidal activity of Duguetia lanceolata A.St.-Hil. (stem bark), Xylopia emarginata Mart. (stem bark), and Xylopia sericea A.St.-Hil. (stem bark and fruits) against D. gallinae. Additionally, the secondary metabolite profile of the X. emarginata was analysed by UFLC-DAD-ESI(+)-MS/MS (micrOTOF-QII) and data analysis was performed using the Molecular Networking. In a topical application test, all plant species tested showed bioactivity, in that order of toxicity with the respective probability survival: X. emarginata (stem bark) (0.28) > X. sericea (stem barks) (0.35) > X. sericea (fruits) and D. lanceolata (stem bark) (0.47). The most promising results were found for X. emarginata (LC50 = 331.769 µg/cm2). It is noteworthy that the LC50 of the insecticide cypermethrin was 1234.4 µg/cm2, which was 73% higher than that of X. emarginata. The metabolomic profile of X. emarginata revealed the presence of alkaloids, amides, terpenoids, and phenolic compounds. This is the first report of X. emarginata acaricidal activity against D. gallinae and exploratory chemical analysis by untargeted metabolomics and the molecular network of this plant.


Assuntos
Acaricidas , Annonaceae , Ácaros , Animais , Annonaceae/química , Cromatografia Líquida de Alta Pressão , Frutas/química , Metabolômica , Casca de Planta/química , Espectrometria de Massas em Tandem
16.
Molecules ; 26(10)2021 May 12.
Artigo em Inglês | MEDLINE | ID: mdl-34065875

RESUMO

The Annonaceae fruits weevil (Optatus palmaris) causes high losses to the soursop production in Mexico. Damage occurs when larvae and adults feed on the fruits; however, there is limited research about control strategies against this pest. However, pheromones provide a high potential management scheme for this curculio. Thus, this research characterized the behavior and volatile production of O. palmaris in response to their feeding habits. Olfactometry assays established preference by weevils to volatiles produced by feeding males and soursop. The behavior observed suggests the presence of an aggregation pheromone and a kairomone. Subsequently, insect volatiles sampled by solid-phase microextraction and dynamic headspace detected a unique compound on feeding males increased especially when feeding. Feeding-starvation experiments showed an averaged fifteen-fold increase in the concentration of a monoterpenoid on males feeding on soursop, and a decrease of the release of this compound males stop feeding. GC-MS analysis of volatiles identified this compound as α-terpineol. Further olfactometry assays using α-terpineol and soursop, demonstrated that this combination is double attractive to Annonaceae weevils than only soursop volatiles. The results showed a complementation effect between α-terpineol and soursop volatiles. Thus, α-terpineol is the aggregation pheromone of O. palmaris, and its concentration is enhanced by host-plant volatiles.


Assuntos
Besouros/metabolismo , Monoterpenos Cicloexânicos/análise , Monoterpenos Cicloexânicos/metabolismo , Feromônios/análise , Feromônios/metabolismo , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/metabolismo , Animais , Annona/metabolismo , Annonaceae/metabolismo , Monoterpenos Cicloexânicos/química , Comportamento Alimentar , Cromatografia Gasosa-Espectrometria de Massas , Comportamento de Busca por Hospedeiro , Larva/metabolismo , Masculino , México , Monoterpenos/metabolismo , Olfatometria , Feromônios/química , Transdução de Sinais , Microextração em Fase Sólida , Inanição/metabolismo , Compostos Orgânicos Voláteis/química
17.
Braz J Biol ; 83: e246455, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34161463

RESUMO

The inheritance of the seedless fruit characteristic of Annona squamosa has not yet been explained. Molecular techniques may aid breeding programs, mainly in the assisted selection of the target gene. The INO gene may be related to seed development in these fruits. The objective of the present paper was to investigate the inheritance of seedlessness in the 'Brazilian seedless' sugar apple and INO gene conservation in Annona squamosa and Annona cherimola x Annona squamosa genotypes by assessing their homology with the INO database genes. The F1 generation was obtained by crossing the mutant 'Brazilian seedless' (male genitor) (P1) with the wild-type A. squamosa with seeds (M1 and M2, female genitors). The INO gene was studied in mutant and wild-type A. squamosa (P1, M1, M2 and M3) and in the Gefner atemoya (A. cherimola x A. squamosa) (M4) cultivar. The DNA was extracted from young leaves, and four sets of specific primers flanking the INO gene were amplified. The seedless characteristic was identified as stenospermatic in the fruits of parental P1, suggesting monogenic inheritance with complete dominance. High sequence similarity of the INO gene amplifications in the sugar apple accessions (M1, M2, M3) and the atemoya cultivar Gefner (M4) reinforces the hypothesis of their conservation.


Assuntos
Annona , Annonaceae , Annona/genética , Brasil , Frutas/genética , Melhoramento Vegetal , Sementes/genética
18.
Acta Chim Slov ; 68(1): 127, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-34057517

RESUMO

This study validates the antidiabetic efficacy of Enantia chlorantha stem bark and the possible therapeutic implications of the co-administration of lisinopril and E. chlorantha in type 2 diabetic rats. E. chlorantha stem bark was extracted by cold maceration. The inhibitory effect of the plant on carbohydrate metabolizing enzymes and its antioxidative potentials were assessed in vitro. The extract exhibited α-amylase and α-glucosidase inhibitory activities and also showed antioxidative properties in vitro. Administration of the extract normalized fasting hyperglycemia in vivo by showing 47.24 % reduction in blood glucose levels relative to untreated diabetic rats. Co-administration of E. chlorantha and lisinopril restored serum glucose and serum lipid profile levels. E. chlorantha stem bark displayed antidiabetic potentials as compared with a standard antidiabetic drug (metformin). The study also showed that the plant contained some bioactive compounds which we hypothesize might be responsible for the observed activities. Co-administration of the plant with lisinopril conferred no significant therapeutic advantage on the serum glucose level and lipid profile.


Assuntos
Diabetes Mellitus Experimental/tratamento farmacológico , Hipoglicemiantes/uso terapêutico , Lisinopril/uso terapêutico , Extratos Vegetais/uso terapêutico , Animais , Annonaceae/química , Glicemia/análise , Glicemia/metabolismo , Peso Corporal/efeitos dos fármacos , Combinação de Medicamentos , Inibidores Enzimáticos/uso terapêutico , Sequestradores de Radicais Livres/uso terapêutico , Masculino , Casca de Planta/química , Caules de Planta/química , Ratos Wistar
19.
J Ethnopharmacol ; 276: 114131, 2021 Aug 10.
Artigo em Inglês | MEDLINE | ID: mdl-33894284

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Breast cancer is a serious threat in low-income as well as developed countries. To face this, many herbal preparations are prescribed by traditional healers in Cameroon, among which is Anonidium mannii commonly called "wild soursop". AIM: This study was undertaken to assess the anti-tumor effect of A. mannii ethanolic extract on cancer cell growth and against DMBA-induced mammary tumors in rats. MATERIALS AND METHODS: The well characterized MTT bioassay was used to assess the cytotoxic potential of A. mannii ethanolic extract in liver (HepG2), prostate (DU145 & PC3) and breast (MCF-7) cancer cell lines. Considering the fact that breast cells were the most sensitive to the extract, a 7,12-dimethylbenz(a)anthracene (DMBA)-induced breast tumor rat model was used to assess the possible anticancer effect of A. mannii extract. Indeed, rats were treated with either tamoxifen (3.3 mg/kg BW) or A. mannii extract (16.5, 50 and 150 mg/kg BW) or vehicle (2% ethanol) for 20 weeks. Tumor incidence, tumor mass and volume, oxidative stress status in tumor as well as tumor histoarchitecture were evaluated. RESULTS: A 24 h incubation of tested cells with the A. mannii extract significantly slowed cell growth in a concentration-dependent manner with an interesting effect in breast cells (IC50 ~61.5 µg/mL). As compared to the DMBA rats, those treated with A. mannii extract (50 and 150 mg/kg) showed reduced breast tumor incidence (28%), tumor burden (95.34% at 50 mg/kg and 99.14% at 150 mg/kg) and tumor volume (~92%). A. mannii extract counteracted the high proliferation of terminal mammary ducts induced by DMBA, mainly at 50 mg/kg. Furthermore, the extract decreased MDA and nitrite levels but increased SOD activity in the mammary gland. High Performance Liquid Chromatography coupled with Mass Spectrometry (HPLC-MS) analysis detected potential anticancer and antioxidant alkaloids in A. manni extract, which are close to those found in Annona muricata. CONCLUSION: These results provide evidence on the in vitro and in vivo anticancer effects of A. mannii, and therefore support its use in traditional medicine system to fight against cancer.


Assuntos
Alcaloides/farmacologia , Annonaceae/química , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Neoplasias Mamárias Experimentais/prevenção & controle , Extratos Vegetais/farmacologia , Alcaloides/uso terapêutico , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/uso terapêutico , Antineoplásicos Fitogênicos/toxicidade , Antioxidantes/química , Antioxidantes/uso terapêutico , Antioxidantes/toxicidade , Camarões , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Etanol/química , Feminino , Humanos , Neoplasias Mamárias Experimentais/sangue , Neoplasias Mamárias Experimentais/patologia , Medicina Tradicional , Minerais/análise , Tamanho do Órgão/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Casca de Planta/química , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Extratos Vegetais/toxicidade , Ratos Wistar , Espectrometria de Massas por Ionização por Electrospray , Tamoxifeno/uso terapêutico , Carga Tumoral/efeitos dos fármacos
20.
Inflammopharmacology ; 29(3): 841-854, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-33864564

RESUMO

In our previous laboratory findings, Cyathocalyx pruniferus extracts exhibited platelet-activating factor inhibition, suggesting their anti-inflammatory potential. Hence, this study was designed with the aim to isolate phyto-constituents from C. pruniferus with potent anti-inflammatory activities. Column and volume liquid chromatography were used for isolation of phyto-constituents. The structure elucidation was carried out using spectroscopic analysis (HRESI-MS, 1H and 13C-NMR) and compared with published literature. For cytotoxicity analysis, 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium-bromide assay was performed on peripheral blood mononuclear cells. Anti-inflammatory activities were evaluated against the levels of inflammatory cytokines (IL-1ß and IL-6), prostaglandin-E2 (PGE2) and cyclooxegenase-2 (COX-2), in lipopolysaccharide (LPS)-induced human plasma using ELISA and radioimmunoassay (RIA). The chromatographic purification of methanol leaves extract afforded 13 (1-13) secondary metabolites. Additionally, cytotoxicity analysis suggested that isolates were non-cytotoxic at 100 µM. In anti-inflammatory evaluation, 2-octaprenyl-1, 4-benzoquinone (5) produced strong (≥ 70%) inhibition of PGE2, COX-2, IL-1ß and IL-6 at 50 µM. Moreover, 2-octaprenyl-1,4-benzoquinone (5) exhibited concentration-dependent inhibition with IC50 values (µM) of 11.21, 6.61, 2.20 and 3.56 as compared to controls; indomethacin for PGE2 (11.84) and dexamethasone in COX-2 (5.19), IL-1ß (1.83) and IL-6 (3.76) analysis, respectively. In conclusion, two new compounds including 2-octaprenyl-1, 4-benzoquinone (5) and 14-methyloctadec-1-ene (6) are reported for the first time from plant species. Additionally, 2-octaprenyl-1, 4-benzoquinone (5) dose-dependently suppressed the production of pro-inflammatory mediators involved in acute and chronic inflammation at non-cytotoxic concentrations.


Assuntos
Annonaceae , Benzoquinonas/farmacologia , Inibidores de Ciclo-Oxigenase 2/farmacologia , Citocinas/antagonistas & inibidores , Dinoprostona/antagonistas & inibidores , Mediadores da Inflamação/antagonistas & inibidores , Extratos Vegetais/farmacologia , Benzoquinonas/isolamento & purificação , Benzoquinonas/metabolismo , Ciclo-Oxigenase 2/metabolismo , Inibidores de Ciclo-Oxigenase 2/isolamento & purificação , Inibidores de Ciclo-Oxigenase 2/metabolismo , Citocinas/metabolismo , Dinoprostona/metabolismo , Humanos , Mediadores da Inflamação/metabolismo , Leucócitos Mononucleares/efeitos dos fármacos , Leucócitos Mononucleares/metabolismo , Lipopolissacarídeos/toxicidade , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/metabolismo , Prenilação/fisiologia
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