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1.
J Oleo Sci ; 73(2): 263-273, 2024 Feb 02.
Artigo em Inglês | MEDLINE | ID: mdl-38233115

RESUMO

Haplophyllum tuberculatum (Forssk.) A.Juss. volatile oils were obtained by distillation of the aerial parts of the plant growing in Libya during the summer and spring seasons. A yield and componential analysis revealed that the summer season oil, which is frequently used in traditional medicaments by North African communities, was high in yield (0.858%) compared to the spring season oil (0.47%), and distinguished by the presence of major and various diverse constituents, some of which are considered chemical markers. Owing to the traditional and high incidence of use of the summer-produced essential oil for the treatment of several disorders, including hepatic diseases, and fatigue, the oil was pharmacologically investigated for its varied bioactivities of anti-microbial, in vivo anti-oxidant, and in vitro anti-cancer properties. Thirty-three compounds were identified and represented 96.2% of the peaks in the GCchromatogram of the summer oil, in which the major volatile constituents were δ-3-carene (21.5%), bornyl acetate (16.9%), and limonene aldehyde (15.2%). The summer-based essential oil of the plant demonstrated moderate anti-bacterial activity against Gram-positive bacteria and a relatively strong antibacterial effect against Gram-negative bacteria as compared to the positive antibacterial controls, ampicillin and gentamicin, respectively. Also, antifungal activity against Aspergillus sp. was observed. The summerproduced oil also exhibited in vivo antioxidant and in vitro anti-cancer activities.


Assuntos
Óleos Voláteis , Rutaceae , Óleos Voláteis/química , Estações do Ano , Antibacterianos/química , Antifúngicos , Antioxidantes/farmacologia , Antioxidantes/química , Rutaceae/química , Testes de Sensibilidade Microbiana , Óleos de Plantas/farmacologia , Óleos de Plantas/química
2.
Chem Biodivers ; 20(12): e202300952, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37994297

RESUMO

The genus Melicope, which consists of 230 species, stands out as the largest genus within the Rutaceae family. Melicope species are characterized by their evergreen nature and can range from shrubs to predominantly dioecious trees. The Melicope species have been utilized in traditional medicine to address a wide range of ailments, including fever, colds, cramps, and inflammation. These plants have gained significant attention due to their noteworthy ethnopharmacological and ethnomedicinal significance. Researchers have isolated numerous biologically active secondary metabolites from different Melicope species, which include polymethoxylated flavonoids, furanocoumarins, acetophenones, benzenoids, and quinolone alkaloids. These compounds exhibit diverse biological activities, such as antibacterial, antidiabetic, antifungal, and antiproliferative properties against human cancer cell lines. This review provides an update on the chemical constituents of the selected species of Melicope. The study also highlights the anticancer and cytotoxicity properties of the plant extracts and phytochemical constituents from Melicope species. Furthermore, the molecular mechanisms underlying the anticancer effects are elucidated. Overall, this review contributes to understanding the significant pharmacological potential of Melicope species and unlocking their chemical composition, emphasizing their relevance in the development of therapeutic agents, particularly in the field of cancer research.


Assuntos
Rutaceae , Humanos , Rutaceae/química , Medicina Tradicional , Etnofarmacologia , Extratos Vegetais , Compostos Fitoquímicos/química , Fitoterapia
3.
Steroids ; 198: 109270, 2023 10.
Artigo em Inglês | MEDLINE | ID: mdl-37414238

RESUMO

To isolate Letrozole from Glycosmis pentaphylla (Retz.) DC. and to determine its effect on regulating the proliferation, cell cycle distribution, apoptosis and key mechanisms in human neuroblastoma cell lines. Letrozole was isolated through column chromatographic technique and its effect was checked on human neuroblastoma cell lines, IMR 32. The effects of Letrozole on cell viability were measured by MTT assay, and the cell cycle distribution was determined by flow cytometry. The expression changes in mRNA of proliferating cell nuclear antigen (PCNA), cyclin D1 and Bcl-xL were taken from real-time PCR analysis and the protein levels were detected by Western blotting. The results of the present study showed that Letrozole, isolated from leaves of G. pentaphylla could cause significant inhibitory effect on proliferation of IMR 32 cells in a dose dependent manner. Cell arrest was obtained at S phase with the treatment of Letrozole. Apart from this, the expression of PCNA, cyclin D1 and Bcl-xL were decreased both at mRNA and protein levels for the same treatment. Letrozole can inhibit proliferation, induce cell arrest and cause apoptosis in IMR 32 cell lines. The decreased expression of PCNA, cyclin D1 and Bcl-xL induced by Letrozole contributes to the above effects in vitro. This is the first report on the isolation of Letrozole from G. pentaphylla.


Assuntos
Neuroblastoma , Rutaceae , Humanos , Antígeno Nuclear de Célula em Proliferação/farmacologia , Linhagem Celular Tumoral , Ciclina D1/genética , Ciclina D1/metabolismo , Letrozol/farmacologia , Apoptose , Rutaceae/química , Rutaceae/genética , Rutaceae/metabolismo , RNA Mensageiro/genética , Proliferação de Células
4.
Molecules ; 28(8)2023 Apr 21.
Artigo em Inglês | MEDLINE | ID: mdl-37110846

RESUMO

Globally, breast cancer is the most prevalent form of cancer in women and there is a need for alternative therapies such as plant-derived compounds with low systemic toxicity and selective toxicity to cancer cells. The aim of this study is to assess the cytotoxicity effects of 7-geranyloxycinnamic acid isolated from leaves of Melicope lunu-ankenda, a traditional medicinal plant, on the human breast cancer cell lines. Dried leaf powder was used for the preparation of different crude extracts using different solvents of increasing order of polarity. The structure of the isolated compound from the petroleum ether extract was elucidated by 1H and 13C NMR, LC-MS, and DIP-MS spectroscopy. The cytotoxic activity of the crude extract and 7-geranyloxycinnamic acid analyzed using MTT assay. Apoptotic analysis was evaluated using Annexin V-PI staining, AO/PI staining, intracellular ROS measurement, and measurement of activities of caspases 3/7, 8, and 9. Crude extracts and the isolated pure compound showed significant cytotoxicity against tested cancer cell lines. 7-geranyloxycinnamic acid was found to exert significant cytotoxic effects against breast cancer cell lines such as the MCF-7 and MDA-MB-231 cell lines. The cytotoxic effects are attributed to its ability to induce apoptosis via accumulation of ROS and activation of caspases in both breast cancer cell lines. The pure compound, 7-geranyloxycinnamic acid isolated from the leaves of M. lunu-ankenda, can exert significant cytotoxic effects against breast cancer cell lines without affecting the normal cells.


Assuntos
Antineoplásicos Fitogênicos , Neoplasias da Mama , Neoplasias do Colo , Rutaceae , Humanos , Feminino , Células MCF-7 , Extratos Vegetais/química , Neoplasias da Mama/tratamento farmacológico , Espécies Reativas de Oxigênio/análise , Rutaceae/química , Folhas de Planta/química , Caspases , Apoptose , Antineoplásicos Fitogênicos/uso terapêutico , Linhagem Celular Tumoral
5.
Fitoterapia ; 168: 105489, 2023 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-36990289

RESUMO

Rutaceae is a family expressed by approximately 2100 species distributed in 154 genera widespread in tropical and temperate regions of Australasia, America, and South Africa. Substantial species of this family are employed as folk medicines. The literature describes the Rutaceae family as a great source of natural and bioactive compounds like terpenoids, flavonoids, and, especially, coumarins. To data, 655 coumarins were isolated and identified from Rutaceae in the past twelve years and, most of them, showed different biological and pharmacological activities. There are studies with coumarins from Rutaceae indicating that these compounds showed activity against cancer, inflammation, infectious diseases, and in the treatment of endocrinal and gastrointestinal conditions. Although coumarins are considered versatile bioactive molecules, until the present, there is no compiled information about coumarins from the Rutaceae family demonstrating the potency of these compounds in all dimensions and chemical similarities among the genera. The present review covers the relevant studies dealing with isolation of Rutaceae coumarins from 2010 until 2022 and outlines the current data on pharmacological activities these coumpounds. Additionally, the chemical disposition and similarity among Rutaceae genera are also statistically discussed employing PCA and HCA methods.


Assuntos
Cumarínicos , Rutaceae , Rutaceae/química , Estrutura Molecular , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Flavonoides
6.
Molecules ; 28(3)2023 Jan 20.
Artigo em Inglês | MEDLINE | ID: mdl-36770745

RESUMO

A phytochemical investigation of the roots of Citrus × paradisi Macfad. (Rutaceae) led to the isolation of two new compounds, namely 1-formyl-5-hydroxy-N-methylindolin-1-ium (1) and decyloxycleomiscosin D (2), along with ten known compounds: 1,1-dimethylpyrrolidin-1-ium-2-carboxylate (3), furan-2,3-diol (4), 5-methoxyseselin (5), umbelliferone (6), scopoletin (7), citracridone I (8), citracridone II (9), citracridone III (10), limonin (11) and lupeol (12). The structures were determined through the comprehensive spectroscopic analysis of 1D and 2D NMR and EI- and ESI-MS, as well as a comparison with the published data. Notably, compounds 3 and 4 from the genus Citrus are reported here for the first time. In addition, the MeOH extract of the roots and compounds 1-7 were screened against the human adenocarcinoma alveolar basal epithelial cell line A549 and the Caucasian prostate adenocarcinoma cell line PC3 using the MTT assay. While the extract showed significant activity, with IC50 values of 35.2 and 38.1 µg/mL, respectively, compounds 1-7 showed weak activity, with IC50 values of 99.2 to 250.2 µM and 99.5 to 192.7 µM, respectively.


Assuntos
Adenocarcinoma , Citrus paradisi , Citrus , Rutaceae , Masculino , Humanos , Rutaceae/química , Extratos Vegetais/química , Alcaloides Indólicos/análise , Raízes de Plantas/química , Estrutura Molecular
7.
Fitoterapia ; 165: 105418, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-36587747

RESUMO

Fourteen new sulphur-containing amides, glycocramides A-N (1-14), as well as nine known analogues (15-23) were isolated and characterized from Glycosmis craibii Tanaka. The chemical structures of new sulphur-containing amides 1-14 were ambiguously elucidated by extensive spectroscopic methods, while the known compounds 15-23 were identified by the comparison of their experimental spectral data with those described data in the literatures. The antiproliferative effects of all isolated sulphur-containing amides were evaluated in vitro. As a result, part of sulphur-containing amides showed remarkable inhibitory effects against MGC-803 cell line with IC50 values ranging from 13.12 ± 0.10 to 20.03 ± 0.13 µM. These research results suggest that the sulphur-containing amides are potentially to be developed as a new natural anti-tumor drugs.


Assuntos
Amidas , Rutaceae , Amidas/farmacologia , Amidas/química , Estrutura Molecular , Enxofre , Extratos Vegetais/química , Rutaceae/química , Linhagem Celular Tumoral
8.
Z Naturforsch C J Biosci ; 78(5-6): 217-227, 2023 May 25.
Artigo em Inglês | MEDLINE | ID: mdl-36367257

RESUMO

Teclea nobilis is a medicinal plant widely used to treat oral pathogens, gonorrhea, fever, analgesics, asthma, joint pains, pneumonia, and intestinal worms in Ethiopia. Anticipated by these claims, column chromatographic separation of the roots extract of T. nobilis led to the isolation of eight alkaloids (1-8). The structures of the isolated compounds were identified based on their NMR (1D and 2D) spectral data analysis and comparison with reported literature data. In-silico molecular docking analysis of the isolated compounds were performed against Staphylococcus aureus DNA Gyrase (PDB ID: 2XCT) and human topoisomerase IIß DNA (PDB ID: 3QX3) by using AutoDock Vina. ADMET analysis were performed by SwissADME, PreADMET, and OSIRIS Property predictions. The study revealed that the isolated compounds exhibited promising binding affinity to DNA gyrase, especially with compound 5 forms a stable drug-protein complex. Whereas the ADME and drug-likeness analysis revealed that compound 5 is less absorbed from the gastrointestinal tract, crossblood brain barrier and a P-glycoprotein substrate. This indicated that compound 5 could be a good candidate as anticancer agent provided that in vivo analysis done for more confirmation.


Assuntos
Alcaloides , Plantas Medicinais , Rutaceae , Humanos , Simulação de Acoplamento Molecular , DNA Girase , Alcaloides/farmacologia , Rutaceae/química
9.
Nat Prod Res ; 37(7): 1098-1105, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-34632889

RESUMO

A new acetophenone dimer, 5'-prenylacrovestone (1), together with nineteen known compounds (2-20), were isolated from the stem bark of Acronychia pedunculata (L.) Miq. Their structures were identified by thorough analysis of spectroscopic (IR, 1D and 2D NMR) and mass spectrometric data. The isolated compounds were tested against the bacterial pathogens MRSA, B. cereus, S. aureus and E. coli. Compound 3 demonstrated exceptionally potent antibacterial activity against each of the four strains (MIC values of 1 µg/mL).


Assuntos
Rutaceae , Thoracica , Animais , Casca de Planta/química , Escherichia coli , Staphylococcus aureus , Acetofenonas/farmacologia , Acetofenonas/química , Rutaceae/química , Antibacterianos/farmacologia , Antibacterianos/análise , Testes de Sensibilidade Microbiana
10.
Nat Prod Res ; 37(2): 197-203, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34498963

RESUMO

Three previously unreported quinolinone alkaloids: melicodenines J-L (1-3) and six known compounds (4-9), were isolated from the leaves of Melicope denhamii (Seem) T.G. Hartley. The structures of three quinolinone alkaloids were identified based on HRESIMS and NMR spectra. Compounds 1-9 were assayed in three cancer cells (MCF-7, HeLa, and P-388). Compounds 1 and 5 showed high cytotoxic activity against HeLa cells with IC50 values of 1.8 and 0.8 µM, respectively.


Assuntos
Alcaloides , Quinolonas , Rutaceae , Humanos , Quinolonas/farmacologia , Quinolonas/química , Células HeLa , Alcaloides/química , Folhas de Planta/química , Rutaceae/química , Estrutura Molecular
11.
Nat Prod Res ; 37(14): 2415-2420, 2023 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-35142584

RESUMO

The ethanolic extract from leaves of Rauia resinosa, Rutaceae, provided a new flavone, 5-hydroxy-5',6,7-trimethoxy-3',4'-methylenedioxyflavone (1), in addition to four known compounds: 3',4',5,5',7-pentamethoxyflavone (2), 5,7,8-trimethoxy-3'4'-methylenedioxyflavone (3), 3',4',5,7,8-pentamethoxyflavone (4) and ß-sitosterol (5). The structures of all compounds were established on the basis of spectroscopic methods, mainly 1D and 2D NMR, UPLC-DAD-MS and UPLC-ESI-MS/MS, involving comparison with literature data. Cytotoxicity of leaves and stems extracts, their fractions and compounds (2), (3), (4) and (5) were evaluated against T24 (bladder carcinoma), TOV-21-G (ovarian adenocarcinoma) and HepG2 (liver carcinoma) cell lines.


Assuntos
Carcinoma , Flavonas , Rutaceae , Humanos , Espectrometria de Massas em Tandem , Flavonas/farmacologia , Flavonas/análise , Rutaceae/química , Extratos Vegetais/química , Folhas de Planta/química
12.
Braz. j. biol ; 83: 1-9, 2023. tab
Artigo em Inglês | LILACS, VETINDEX | ID: biblio-1468869

RESUMO

The present study was conducted to evaluate the chemical composition, antioxidant activity and hypoglycemic effects of whole kumquat (Ku) powder in diabetic rats fed a high-fat-high-cholesterol (HFHC) diet. The antioxidant activities were evaluated using stable 1,1-diphenyl 2-picrylhydrazyl (DPPH) free radical scavenging method, 2,2'-azinobis (3-ethyl benzo thiazoline-6-sulphonic acid) radical cation (ABTS) and Ferric reducing antioxidant power (FRAP). Total phenolic content was (51.85 mg GAE/g) and total flavonoid content was (0.24 mg Cateachin Equivalent, CE/g). DPPH and ABTS values were 3.32 and 3.98 mg Trolox equivalent (TE)/g where FRAP value was 3.00 mM Fe²+/kg dry material. A total of 90 albino rats were used in the present study. Rats group were as follows: normal diet; normal treated (2, 4, and 6% Ku.), diabetic rats (non-treated), diabetic + HFHC diet (non-treated), HFHC (non-treated), Diabetic (treated), HFHC (treated) and Diabetic + HFHC (treated). The diets were followed for 8 weeks. Blood samples were collected at the end of the experiment. Serum glucose was recorded and thyroid hormones (T4, Thyroxine and T3, Triiodothyronine) were conducted. Diet supplemented with Kumquat at different concentrations have a hypoglycemic effect and improve the thyroid hormones of both diabetic rats and HFHC diabetic rats.


O presente estudo foi conduzido para avaliar a composição química, a atividade antioxidante e os efeitos hipoglicêmicos do pó de kumquat (Ku) em ratos diabéticos alimentados com uma dieta rica em gordura e colesterol (HFHC). As atividades antioxidantes foram avaliadas usando o método de eliminação de radicais livres de 1,1-difenil 2-picrilhidrazil (DPPH), 2,2'-azinobis (ácido 3-etilbenzotiazolina-6-sulfônico) radical cátion (ABTS) e antioxidante redutor férrico potência (FRAP). O conteúdo fenólico total foi (51,85 mg GAE / g) e o conteúdo total de flavonoides foi (0,24 mg Cateachin Equivalent, CE / g). Os valores de DPPH e ABTS foram 3,32 e 3,98 mg equivalente de Trolox (TE) / g, em que o valor de FRAP foi de 3,00 mM Fe²+ / kg de material seco. Um total de 90 ratos albinos foi usado no presente estudo. O grupo dos ratos foi o seguinte: dieta normal: tratados normais (2, 4 e 6% Ku.), ratos diabéticos (não tratados), diabéticos + dieta HFHC (não tratados), HFHC (não tratados), diabéticos (tratados), HFHC (tratados) e diabéticos + HFHC (tratados). As dietas foram seguidas por 8 semanas. Amostras de sangue foram coletadas ao final do experimento. A glicose sérica foi registrada e os hormônios tireoidianos (T4, Tiroxina e T3, Triiodotironina) foram conduzidos. A dieta suplementada com kumquat em diferentes concentrações tem um efeito hipoglicêmico e melhora os hormônios tireoidianos tanto de ratos diabéticos quanto de ratos diabéticos com HFHC.


Assuntos
Animais , Ratos , Antioxidantes/análise , Diabetes Mellitus/tratamento farmacológico , Hipoglicemiantes/análise , Hormônios Tireóideos/farmacologia , Ratos/metabolismo , Ratos/sangue , Rutaceae/química
13.
Molecules ; 27(18)2022 Sep 14.
Artigo em Inglês | MEDLINE | ID: mdl-36144708

RESUMO

Plants are serving the mankind with important bioactive phytochemicals from the very ancient ages to develop novel therapeutics against different disease states. Glycosmis cyanocarpa (Blume) Spreng is a plant from the Rutaceae family and a very less explored species from the Glycosmis genus. Thus, this present study was intended to present the chemical and biological investigation of Glycosmis cyanocarpa (Blume) Spreng. The chemical investigation resulted in the isolation of one new phenolic compound to the best of our knowledge which is (4-(3-hydroxy-2-methylpropyl)-2-methoxyphenol) (1) along with four known compounds that are isolated for the first time from this species- 3-methyl-1H-indole (2), Tri-transpoly-cis prenol-12 (3), Stigmasterol (4) and ß-sitosterol (5). Their chemical structures were elucidated based on extensive spectroscopic methods, including 1D and 2D NMR, and comparison with the available literature data. Isolated phytochemicals were further investigated to unveil their antioxidant properties with IC50 values (ranged from 9.97-75.48 µg/mL), cytotoxicity with LC50 values (ranged from 1.02-1.92 µg/mL), and antibacterial properties against some selected Gram (+) ve and Gram (-) ve bacteria. Among the compounds, 3-methyl-1H-indole (2) was found to be the most active against Staphylococcus aureus. Moreover, the phenolic compound (1) and the alkaloid (2) revealed the highest antioxidant (9.97 µg/mL) and cytotoxic activities (1.02 µg/mL), respectively. Thus, the isolation of these bioactive phytochemicals from the plant revealed a new perception in the study arena of drug discovery and the findings may ease the development and discovery of novel therapeutics. Further investigations are still recommended to understand their exact molecular mechanism and toxicological impact.


Assuntos
Alcaloides , Rutaceae , Antibacterianos/química , Antioxidantes/farmacologia , Guaiacol , Indóis , Fenóis/farmacologia , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Rutaceae/química , Estigmasterol
14.
Molecules ; 27(12)2022 Jun 16.
Artigo em Inglês | MEDLINE | ID: mdl-35744993

RESUMO

The present study aimed to investigate the effect of acridone alkaloids on cancer cell lines and elucidate the underlying molecular mechanisms. The ten acridone alkaloids from Atalantia monophyla were screened for cytotoxicity against LNCaP cell lines by a WST-8 assay. Then, the most potential acridone, buxifoliadine E, was evaluated on four types of cancer cells, namely prostate cancer (LNCaP), neuroblastoma (SH SY5Y), hepatoblastoma (HepG2), and colorectal cancer (HT29). The results showed that buxifoliadine E was able to significantly inhibit the proliferation of all four types of cancer cells, having the most potent cytotoxicity against the HepG2 cell line. Western blotting analysis was performed to assess the expression of signaling proteins in the cancer cells. In HepG2 cells, buxifoliadine E induced changes in the levels of Bid as well as cleaved caspase-3 and Bax through MAPKs, including Erk and p38. Moreover, the binding interaction between buxifoliadine E and Erk was investigated by using the Autodock 4.2.6 and Discovery Studio programs. The result showed that buxifoliadine E bound at the ATP-binding site, located at the interface between the N- and C-terminal lobes of Erk2. The results of this study indicate that buxifoliadine E suppressed cancer cell proliferation by inhibiting the Erk pathway.


Assuntos
Alcaloides , Neoplasias , Rutaceae , Acridonas/química , Acridonas/farmacologia , Alcaloides/química , Alcaloides/farmacologia , Apoptose , Linhagem Celular Tumoral , Proliferação de Células , Sistema de Sinalização das MAP Quinases , Rutaceae/química
15.
Chem Biodivers ; 19(7): e202101033, 2022 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-35678514

RESUMO

The stem bark of Citrus × paradisi Macfad. (Rutaceae) gave (23S)-isolimonexic acid (1), limonin (2), citracridone II (3), citpressine II (4), citpressine I (5), grandisine (6), 2-hydroxynoracronycine (7), citracridone I (8), 5-methoxyseselin (9), umbelliferone (10), scopoletin (11), naringenin (12), apigenin (13), friedelin (14), agrostophyllinone (15) and stigmasterol-3-O-ß-D-glucopyranoside (16). The structures of the compounds were determined using NMR and MS spectroscopic data, and by comparison with published data. The relative configuration of 1 was proposed as (23S)-isolimonexic acid using NOE studies. Hydrogenation reaction of compound 3 led to the new derivative 3',4'-dihydrocitracridone II (3a). Cytotoxicity activities against the human adenocarcinoma alveolar basal epithelial cell lines A549 and the Caucasian prostate adenocarcinoma cell lines PC3, using the MTT assays showed that the methanol crude extract was significant with IC50 values of 30.1 and 31.7 µg/mL, respectively, with the positive control, doxorubicin giving an IC50 of 0.9 µM. In addition, compounds 3, 7 and 8 gave moderate cytotoxic activities with IC50 values of 33.1, 31.2 and 32.5 µM for A549 cells and 35.7, 33.8 and 34.9 µM for PC3 cells, respectively. The hydrogenated 3a was less active than 3, suggesting that the presence of the double bond in pyrans is important for structure-activity relationship.


Assuntos
Adenocarcinoma , Citrus paradisi , Citrus , Rutaceae , Humanos , Masculino , Casca de Planta/química , Extratos Vegetais/química , Rutaceae/química
16.
Anal Bioanal Chem ; 414(14): 4103-4118, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35419692

RESUMO

Mass spectrometry-based plant metabolomics allow large-scale analysis of a wide range of compounds and the discovery of potential new active metabolites with minimal sample preparation. Despite recent tools for molecular networking, many metabolites remain unknown. Our objective is to show the complementarity of collision cross section (CCS) measurements and calculations for metabolite annotation in a real case study. Thus, a systematic and high-throughput investigation of root, bark, branch, and leaf of the Gabonese plant Zhanthoxylum heitzii was performed through ultra-high performance liquid chromatography high-resolution tandem mass spectrometry (UHPLC-QTOF/MS). A feature-based molecular network (FBMN) was employed to study the distribution of metabolites in the organs of the plants and discover potential new components. In total, 143 metabolites belonging to the family of alkaloids, lignans, polyphenols, fatty acids, and amino acids were detected and a semi-quantitative analysis in the different organs was performed. A large proportion of medical plant phytochemicals is often characterized by isomerism and, in the absence of reference compounds, an additional dimension of gas phase separation can result in improvements to both quantitation and compound annotation. The inclusion of ion mobility in the ultra-high performance liquid chromatography mass spectrometry workflow (UHPLC-IMS-MS) has been used to collect experimental CCS values in nitrogen and helium (CCSN2 and CCSHe) of Zhanthoxylum heitzii features. Due to a lack of reference data, the investigation of predicted collision cross section has enabled comparison with the experimental values, helping in dereplication and isomer identification. Moreover, in combination with mass spectra interpretation, the comparison of experimental and theoretical CCS values allowed annotation of unknown features. The study represents a practical example of the potential of modern mass spectrometry strategies in the identification of medicinal plant phytochemical components.


Assuntos
Metabolômica , Compostos Fitoquímicos , Extratos Vegetais , Rutaceae , Cromatografia Líquida de Alta Pressão/métodos , Isomerismo , Espectrometria de Massas/métodos , Metabolômica/métodos , Compostos Fitoquímicos/análise , Extratos Vegetais/química , Plantas Medicinais/química , Rutaceae/química
17.
Molecules ; 27(3)2022 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-35164367

RESUMO

The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2-10. In addition, six semi-synthetic derivatives 3a-c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new N-allylindolopyridoquinazoline 5a is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds 2-4 were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (5). The TAE, fractions, compounds 1-7 and 9, and semi-synthetic derivatives 3a-c, 4b, 5a and 6a were evaluated for their cytotoxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for 9, which showed moderate activity against the tested cancer cell lines.


Assuntos
Alcaloides/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Casca de Planta/química , Extratos Vegetais/farmacologia , Rutaceae/química , Neoplasias do Colo do Útero/tratamento farmacológico , Feminino , Humanos , Indóis/química , Piridinas/química , Quinazolinas/química , Células Tumorais Cultivadas
18.
J Ethnopharmacol ; 284: 114781, 2022 Feb 10.
Artigo em Inglês | MEDLINE | ID: mdl-34715298

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Genus Fagaropsis belonging to the Rutaceae family, is widely distributed in Africa. The various parts of the species in this genus are used in traditional herbal medicine in different parts of the continent for the treatment of malaria, intestinal disorders, cancer, respiratory diseases, and other ailments. AIM OF THE STUDY: This study provides a comprehensive and updated review on the ethnobotanical uses, phytochemistry, and pharmacology of Fagaropsis species and highlights possible research gaps for further research opportunities, which will be important in the development of new therapeutic drugs. MATERIALS AND METHODS: The data was retrieved using ethnobotanical books, published articles, electronic sources, and scientific databases such as Google Scholar, Plants of the World, The Plant List, Scopus, Wiley, Web of Science, PubMed, Science direct, and Sci-Finder. Various key search words Fagaropsis, pharmacological activities, phytochemistry, and ethnobotanical uses were used in the detailed study survey. RESULTS: Fagaropsis species are used traditionally to treat a wide range of infections such as respiratory diseases, cancer, malaria, intestinal diseases, and ethnoveterinary. Phytochemical investigations indicated 18 phytoconstituents that have been isolated as the main compounds in this genus; triterpenoids (limonoids, norhopane, and norneohopane derivatives), alkaloids, and essential oils. Few in vitro and in vivo pharmacological activities have been analyzed in this genus. They indicated that the extracts and pure compounds contained anti-inflammatory, antiplasmodial, anti-cancer, anti-bacterial, anti-fungal, and insecticidal activities. The phytochemical compounds that may be responsible for these activities are flavonoids, terpenoids, and alkaloids. CONCLUSION: The ethnobotanical values, phytochemistry, and pharmacology discussed in this review paper showed that Fagaropsis species contain different compounds possessing a wide range of biological activities, and they have high medicinal value that is significant in treating different types of diseases. Phytochemical analyses have been performed on two species (F. angolensis and F. glabra) in the literature. More scientific research analyses are still required to explore this genus. In addition, the majority of the currently available bioactivity-related analyses were applied to crude extracts. Thus, further research studies are important to reveal the links between ethnobotanical uses and bioactivity in the future.


Assuntos
Medicinas Tradicionais Africanas , Compostos Fitoquímicos , Fitoterapia , Rutaceae/química , Animais , Etnofarmacologia , Humanos , Plantas Medicinais
19.
Nat Prod Res ; 36(17): 4439-4442, 2022 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34570617

RESUMO

Ravenia spectabilis Engl. belongs to the family Rutaceae is known to possess several biologically active phytomolecules. This study was planned to investigate the chemical composition and antimicrobial activity of the leaf essential oil of R. spectabilis. The hydrodistillation of fresh leaves of R. spectabilis gave 0.19 ± 0.02% essential oil. The resulting essential oil was analysed by gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Altogether, thirty-one constituents forming 97.6 ± 1.72% of the total oil composition were identified. Major components of the oil were sabinene (60.8 ± 0.36%), α-pinene (5.4 ± 0.30%), myrcene (4.8 ± 0.25%), δ-3-carene (4.7 ± 0.62%) and ß-pinene (4.3 ± 0.17%). The in-vitro antimicrobial potential of the oil was examined against eight human pathogenic bacterial and fungal strains. The essential oil showed significant activity against Staphylococcus aureus, Staphylococcus epidermidis, methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, Candida albicans, and Candida kefyr. This is the first report on R. spectabilis leaf essential oil composition and its antimicrobial activity. The essential oil could be a promising natural source of sabinene and antimicrobial for developing new phytotherapeutics.


Assuntos
Anti-Infecciosos , Staphylococcus aureus Resistente à Meticilina , Óleos Voláteis , Rutaceae , Antibacterianos/química , Anti-Infecciosos/química , Candida albicans , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Testes de Sensibilidade Microbiana , Óleos Voláteis/química , Folhas de Planta/química , Rutaceae/química
20.
Arch Pharm (Weinheim) ; 355(1): e2100277, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34486161

RESUMO

Chemotherapy is the first choice for the majority of cancers, but severe side effects and drug resistance restrict the actual clinical efficacy. Carbazole alkaloids, mainly from the Rutaceae family, possess favorable donor ability, good planarity, rich photophysical properties, and excellent biocompatibility. Carbazole alkaloids could not only intercalate in DNA but could also inhibit telomerase and topoisomerase and regulate protein phosphorylation. Hence, carbazole alkaloids are useful in providing lead hits/candidates for the development of novel anticancer agents. This review summarizes the research progress made regarding the anticancer properties of carbazole alkaloids, covering articles published from January 2010 to June 2021.


Assuntos
Alcaloides/farmacologia , Antineoplásicos/farmacologia , Carbazóis/farmacologia , Alcaloides/química , Animais , Antineoplásicos/química , Carbazóis/química , Desenvolvimento de Medicamentos , Humanos , Neoplasias/tratamento farmacológico , Rutaceae/química
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