RESUMO
A total of five new mexicanolides (1-5), namely alliaxylines A-E, together with two known limonoids 6 and 7, were isolated and identified from Dysoxylum alliaceum (Blume) Blume ex. A.Juss. (Meliaceae). The structures of these compounds were elucidated based on extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D, and 2D NMR, as well as theoretical stimulation of NMR shifts with the DP4 + algorithm. Consequently, this study aimed to examine cytotoxic activities of these compounds against MCF-7 and A549 cell lines. The results implied that compound 2 was the most potent against the two tested cells, with IC50 values of 34.95 ± 0.21 and 44.39 ± 1.03 µM.
Assuntos
Limoninas , Meliaceae , Casca de Planta , Humanos , Meliaceae/química , Casca de Planta/química , Limoninas/química , Limoninas/farmacologia , Limoninas/isolamento & purificação , Estrutura Molecular , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Células MCF-7 , Células A549 , Linhagem Celular Tumoral , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Caules de Planta/químicaRESUMO
Swietenia macrophylla King is a plant commonly known as Brazilian mahogany. The wood from its stem is highly prized for its exceptional quality, while its leaves are valued for their high content of phragmalin-type limonoids, a subclass of compounds known for their significant biological activities, including antimalarial, antitumor, antiviral, and anti-inflammatory properties. In this context, twelve isolated limonoids from S. macrophylla leaves were employed as standards in mass spectrometry-based molecular networking to unveil new potential mass spectrometry signatures for phragmalin-type limonoids. Consequently, ultra-performance liquid chromatography coupled with high-resolution mass spectrometry was utilized for data acquisition. Subsequently, the obtained data were analyzed using the Global Natural Products Social Molecular Networking platform based on spectral similarity. In summary, this study identified 24 new putative phragmalin-type limonoids for the first time in S. macrophylla. These compounds may prove valuable in guiding future drug development efforts, leveraging the already established biological activities associated with limonoids.
Assuntos
Limoninas , Meliaceae , Limoninas/química , Meliaceae/química , Espectrometria de Massas , Brasil , Estrutura MolecularRESUMO
The methanol extract of the seeds of Khaya ivorensis afforded two new mexicanolide limonoids, ivorensines A and B (1 and 2), together with one known compound, ruageanin D (3). The structures of the isolated compounds were established based on 1 D and 2 D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. The isolated limonoids were tested in vitro for antimicrobial potentials against 5 pathogenic microorganisms. As a result, compounds 1-3 exhibited antimicrobial activity against the tested Gram negative bacteria at the minimum inhibitory concentration values less than 50 µg/ml.
Assuntos
Limoninas , Meliaceae , Limoninas/química , Estrutura Molecular , Meliaceae/química , Sementes/químicaRESUMO
Three new mexicanolide limonoids were obtained from the 90% ethanol extract of the seeds of Khaya senegalensis. Their structures were elucidated as senegalenines A-C (1-3) by analysing their 1D/2D NMR and MS spectroscopic analysis. In addition, the isolated limonoids were tested in vitro for antimicrobial potentials against 5 pathogenic microorganisms. Consequently, compounds 1-3 exhibited antimicrobial activity against the tested Gram negative bacteria at the minimum inhibitory concentration values less than 40 µg/ml.
Assuntos
Limoninas , Meliaceae , Antibacterianos/farmacologia , Limoninas/química , Meliaceae/química , Estrutura Molecular , Sementes/químicaRESUMO
Cedrela genus, a member of the Meliaceae family, presents both chemical characteristics associated with and those that distinguish it from the rest of its members. The presence of triterpenes and limonoids is the characteristic of the Meliaceae family, but the class and type of these chemical constituents are distinctive for each genus. Cedrela includes cycloartane, ursane, oleanane, tirucallane, butyrospermane, and apotirucallane triterpenes, and its limonoids belongs to six class and nine types, known as class Ia-type havanensines, class Ib-type delevoyin, class II-type gedunin, class IIIb-type andirobin, class IIIg-type mexicanolide, class IVa-type evoludone, class Va-type obacunol, class V-type limonin, and class VIII. Each of these structural arrangements includes specific traits, defined by their biosynthetic origin, which can be established by means of structural elucidation techniques, particularly 1 H and 13 C NMR, which assisted by 2D NMR techniques, allowing to deduce their structures unequivocally. The constant presence of these skeletal arrangements in Cedrela ensures that they are its chemophenetic markers and their recurrence is an important criterion for their identity. This review is a compilation of the occurrence of triterpenes and limonoids in Cedrela genus, detailing their biosynthetic association and collecting and organizing their NMR data, with the purpose of facilitating its location, analysis, and use in the phytochemical study of species from this genus.
Assuntos
Cedrela , Limoninas , Meliaceae , Triterpenos , Cedrela/química , Limoninas/química , Espectroscopia de Ressonância Magnética , Meliaceae/química , Estrutura Molecular , Triterpenos/químicaRESUMO
AIMS: Swietenia macrophylla have been considered for the treatment of various diseases, including anticancer activity. This study aimed to investigate the anticancer activity of S. macrophylla leaves extract and its isolated compound towards human colorectal cancer cell line. MAIN METHODS: Hexanic extract of S. macrophylla leaves demonstrated relevant cytotoxicity only against colon cancer cell line HCT116. KEY FINDINGS: Our results showed significant DNA damage and apoptosis after treatment with the hexanic extract of S. macrophylla. Moreover, no toxicity was noticed for the animal model. The isolated compound limonoid L1 showed potent cytotoxicity against cancer cell lines with IC50 at 55.87 µg mL-1. Limonoid L1 did not trigger any cell membrane rupture in the mice erythrocytes suggesting no toxicity. The antiproliferative effect of L1 was confirmed in colorectal cancer cells by clonogenic assay, inducing G2/M arrest, apoptosis, and DNA damage in cancer-type cells. SIGNIFICANCE: L1 reduced BCL2 and increased ATM, CHK2, TP53, ARF, CDK1, CDKN1A, and CASP3 in the colorectal cancer cell line. These findings suggest that limonoid L1 isolated from S. macrophylla can be a promising anticancer agent in managing colorectal cancer.
Assuntos
Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Neoplasias Colorretais/patologia , Dano ao DNA , Limoninas/farmacologia , Meliaceae/química , Animais , Neoplasias Colorretais/metabolismo , Eritrócitos/efeitos dos fármacos , Feminino , Pontos de Checagem da Fase G2 do Ciclo Celular/efeitos dos fármacos , Células HCT116 , Hemólise , Humanos , Limoninas/isolamento & purificação , Limoninas/uso terapêutico , Camundongos , Extratos Vegetais/química , Extratos Vegetais/farmacologiaRESUMO
Six undescribed 1,8,9-phragmalin limonoid orthoesters (chukorthoesters A-F, 1-6) and two undescribed mexicanolide-type limonoids (ivorenoids H and I, 7 and 8), together with ten known limonoids, were isolated from the seeds of common wood-source and greening plants Chukrasia tabularis A. Juss. Their chemical structures were elucidated using HR-ESI-MS, 1D and 2D NMR spectroscopic analysis, and that of 1 along with absolute configuration was confirmed by X-ray diffraction experiment with Cu Kα radiation. Bioactivities screening indicated the limonoid orthoesters 1 and 2 shown reversing resistance in MCF-7/DOX cells at 10 µM (RF:4-5 folds).
Assuntos
Limoninas , Meliaceae , Resistência a Múltiplos Medicamentos , Humanos , Limoninas/farmacologia , Estrutura Molecular , SementesRESUMO
Plant tissue culture has emerged as an important tool to produce bioactive compounds from various plant species, including the sustainable production of limonoids that are receiving considerable attention due to the benefits associated with human health such as anticancer activities. The purpose of the present study was to evaluate the capacity of limonoids aglycone production from callus culture from sweet orange cv. Pera (Citrus sinensis) seeds and identify the compounds produced in this cell line. Callus induction occurred in Murashige and Skoog medium supplemented with 2,4-dichlorophenoxyacetic (2,4-D), malt extract, agar and coconut water. For the analysis and identification of the limonoids, CG-MS-EI ion-positive mode and UPLC-QTOF-ESI were used operating in positive and negative mode. An intense peak corresponding to limonin appeared in the callus extracts at a retention time of 58.1 min. in CG-MS-EI and four major limonoids aglycone by positive ion mode UPLC-QTOF-ESI: limonin, nomilin, deacetylnomilin, and nomilinic acid. The culture medium was efficient at the bioproduction of limonoids aglycone in callus cultures of C. sinensis seeds. Therefore, data obtained from UPLC-QTOF-ESI proved its importance at identifying new compounds that benefit human health, and may assist future work in the identification of known or new limonoids in Citrus species and related genera.(AU)
Assuntos
Limoninas/classificação , Citrus sinensis/química , Compostos Fitoquímicos , BiotecnologiaRESUMO
Plant tissue culture has emerged as an important tool to produce bioactive compounds from various plant species, including the sustainable production of limonoids that are receiving considerable attention due to the benefits associated with human health such as anticancer activities. The purpose of the present study was to evaluate the capacity of limonoids aglycone production from callus culture from sweet orange cv. Pera (Citrus sinensis) seeds and identify the compounds produced in this cell line. Callus induction occurred in Murashige and Skoog medium supplemented with 2,4-dichlorophenoxyacetic (2,4-D), malt extract, agar and coconut water. For the analysis and identification of the limonoids, CG-MS-EI ion-positive mode and UPLC-QTOF-ESI were used operating in positive and negative mode. An intense peak corresponding to limonin appeared in the callus extracts at a retention time of 58.1 min. in CG-MS-EI and four major limonoids aglycone by positive ion mode UPLC-QTOF-ESI: limonin, nomilin, deacetylnomilin, and nomilinic acid. The culture medium was efficient at the bioproduction of limonoids aglycone in callus cultures of C. sinensis seeds. Therefore, data obtained from UPLC-QTOF-ESI proved its importance at identifying new compounds that benefit human health, and may assist future work in the identification of known or new limonoids in Citrus species and related genera.
Assuntos
Biotecnologia , Citrus sinensis/química , Compostos Fitoquímicos , Limoninas/classificaçãoRESUMO
The genus Cedrela P. Browne, which belongs to the Meliaceae family, has eighteen species. Trees of this genus are of economic interest due to wood quality, as well as being the focus of studies because of relevant biologic activities as in other Meliaceae species. These activities are mainly related to limonoids, a characteristic class of compounds in this family. Therefore, the aim of this review is to perform a survey of the citations in the literature on the Cedrela genus species. Articles were found on quantitative and qualitative phytochemical studies of the Cedrela species, revealing the chemical compounds identified, such as aliphatics acid and alcohol, flavonoids, tocopherol, monoterpenes, sesquiterpenes, triterpenes, cycloartanes, steroids, and limonoids. Although some activities were tested, the majority of studies focused on the insecticidal, antifeedant, or insect growth inhibitor activities of this genus. Nonetheless, the most promising activities were related to their antimalarial and antitripanocidal effects, although further investigations are still needed.
Assuntos
Cedrela/química , Compostos Fitoquímicos/farmacologia , Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Cedrela/crescimento & desenvolvimento , Concentração Inibidora 50 , Compostos Fitoquímicos/química , Desenvolvimento Vegetal/efeitos dos fármacosRESUMO
Plant materials (i.e., leaves, fruits, and seeds) from 40 trees of Azadirachta indica A. Juss. were collected from six different locations across the Colombian Caribbean coast. Eighty-four ethanolic extracts were prepared and the total limonoid contents (TLiC) and the antifungal activity against Fusarium oxysporum conidia were measured. Their chemical profiles were also recorded via liquid chromatography-electrospray ionization interface-mass spectrometry (LC-ESI-MS) analysis and the top-ranked features were then annotated after supervised multivariate statistics. Inter-location chemical variability within sample set was assessed by sparse partial least squares discriminant analysis (sPLS-DA) and the chemical profiles and biological activity datasets were integrated through single-Y orthogonal partial least squares (OPLS) to identify antifungal bioactives in test extracts. The TLiC and antifungal activity (IC50 values) of the A. indica-derived extracts were found to be ranging from 4.5 to 48.5 mg limonin equivalent per g dry extract and 0.08-44.8 µg/mL, respectively. The presence/abundance of particular limonoids between collected samples influenced the variability among locations. In addition, the integration of chemical and antifungal activity datasets showed five features as markers probably contributing to the bioactivity, annotated as compounds with an azadirone-like moiety. To validate the information provided by the single-Y OPLS model, a high performance liquid chromatography (HPLC)-based microfractionation was then carried out on an active extract. The combined plot of chromatographic profile and microfraction bioactivity also evidenced five signals possessing the highest antifungal activity. The most active limonoid was identified as nimonol 1. Hence, this untargeted metabolite profiling was considered as a convenient tool for identifying metabolites as inter-location markers as well as antifungals against Fusarium oxysporum.
RESUMO
Abstract The chemical study of roots from Azadirachta indica A. Juss., Meliaceae, led to the isolation of two new terpenoids, limonoid morenolide and diterpene 17-hydroxy-sandaracopimar-8,15-dien-11-one, in addition to the four well-known limonoids nimbinene, nimbinal, nimbandiol and salannin, and three diterpenoids nimbidiol, ferruginol, and 6,7-dehydroferruginol. Their structural elucidations were based on one and bidimensional Nuclear Magnetic Resonance and Electrospray ionization mass spectrometry spectra data which was compared to the data found in literature. The anti-inflammatory, cytotoxic and antimycobacterial activities of the identified terpenoids were evaluated.
RESUMO
Eleven previously undescribed limonoids, trichisins A-K, including eight structural analogues A-H of trijugin and three H-J mexicanolide derivatives, together with two known mexicanolide derivatives were isolated from the fruits of Heynea trijuga Roxb. ex Sims. The structure determination was based on extensive physical data analyses (NMR, MS), and their basic skeletons and the absolute configurations of trichisins A, B, E, K and trichiconnarone A were assigned via X-ray crystallographic analysis (Cu Kα radiation). The hemiketal motifs in trijugins A, B, and E-G are rare in limonoids. Bioactivity screenings suggested that the trijugin H and mexicanolide-type trichiconnarones A and B limonoids were effective in reversing resistance in MCF-7/DOX cells at a nontoxic concentration of 50⯵M with IC50 values of 12.45, 10.86, and 14.96⯵M, respectively.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Resistência a Múltiplos Medicamentos/efeitos dos fármacos , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Frutas/química , Limoninas/farmacologia , Meliaceae/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Limoninas/química , Limoninas/isolamento & purificação , Modelos Moleculares , Conformação Molecular , Relação Estrutura-AtividadeRESUMO
Three new mexicanolide-type limonoids, 3-O-propionylproceranolide (1), 6-O-acetylswietenin B (2), and 6-deoxyswietemahonin A (3), together with 15 known limonoids, were isolated from the seeds of Swietenia macrophylla (Meliaceae). The structures of those new compounds were established by extensive analysis of MS, 1D, and 2D NMR spectral data.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Limoninas/isolamento & purificação , Meliaceae/química , Medicamentos de Ervas Chinesas/química , Limoninas/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sementes/químicaRESUMO
One new chromone 3,3-dimethylallylspatheliachromene methyl ether (1), as well as five known chromones, 6-(3-methylbut-2-enyl) allopteroxylin methyl ether (2), 6-(3-methylbut-2-enyl) allopteroxylin (3), 3,3-dimethylallylspatheliachromene (4), 5-O-methylcneorumchromone K (5) and spatheliabischromene (6), two alkaloids, 8-methoxy-N-methylflindersine (7) and 8-methoxyflindersine (8), and two limonoids, limonin diosphenol (9) and rutaevin (10), were isolated from Dictyoloma vandellianum A. Juss (Rutaceae). Cytotoxic activities towards tumor cell lines B16-F10, HepG2, K562 and HL60 and non-tumor cells PBMC were evaluated for compounds 1 - 6. Compound 1 was the most active showing IC50 values ranging from 6.26 to 14.82 µg/ml in B16-F10 and K562 cell lines, respectively, and presented IC50 value of 11.65 µg/ml in PBMC cell line.
Assuntos
Cromonas/química , Rutaceae/química , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/toxicidade , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cromonas/isolamento & purificação , Cromonas/toxicidade , Células HL-60 , Células Hep G2 , Humanos , Células K562 , Leucócitos Mononucleares/citologia , Leucócitos Mononucleares/efeitos dos fármacos , Leucócitos Mononucleares/metabolismo , Limoninas/química , Limoninas/isolamento & purificação , Limoninas/toxicidade , Espectroscopia de Ressonância Magnética , Camundongos , Folhas de Planta/química , Folhas de Planta/metabolismo , Rutaceae/metabolismoRESUMO
Four new mexicanolide-type limonoids 1-4, along with two known limonoids 5-6, were isolated from the ethanolic extracts of roots of the Traditional Chinese Medicine Trichilia sinensis. Their structures were unambiguously determined by analysis of spectroscopic data, including 1D and 2D NMR as well as MS, and by comparison with literature data. In addition, the acetylcholinesterase (AChE) inhibitory activity of compounds 1-6 was evaluated by the Ellman method. All these compounds showed weak AChE inhibitory activity, with the inhibition percentages ranging from 18.5% to 27.8%.
Assuntos
Inibidores da Colinesterase , Limoninas , Meliaceae/química , Raízes de Plantas/química , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Limoninas/química , Limoninas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Cedrela odorata (Meliaceae) is a native timber tree to Tropical America, known for its high-quality wood, unfortunately, plantations of this species are severely attacked by Hypsipyla grandella. The attraction or repellency of this pest is related to secondary metabolites such as phenols and limonoids (triterpenes); therefore, it is important to study these compounds to understand the phytochemical phenomena behind this problem. With this aim, the concentration of total phenols and limonoides was evaluated in C. odorata leaves from a plantation established in Tezonapa Veracruz, Mexico. For this, a total of 66 tree leaves samples, from seven sites, were analyzed. Phenols and limonoids concentration showed significant differences not only among different provenances, but also among individual trees of the same site (Tukey, p≤0.05). Phenols concentration was variable and in the range from 49 to 223mg EAG/g e for total phenols, from 7 to 158mg EC/g e for flavonoids and from 4 to 104mg EC/g e for proanthocyanidins. Limonoids concentration was also variable, ranging between 227 and 748mg EL/g e. A major compound was found by High-Performance Liquid Chromatography with Ultraviolet Diode Array Detection (HPLC-UV-DAD), which corresponded to a flavonol kaempferol glycoside derivative; additionally, a flavanol catechin was also detected at low concentrations. GC-MS allowed the identification of the sesquiterpenoids β-elemene, E-caryophyllene, aromadendrene, α-humulene, γ-cadinene, D-germacrene, bicyclogermacrene, and the poly terpenoids D-α-tocopherol and β-sitosterol. Our results suggest that the evaluation of phenols may play an important role as a selection parameter for improvement and conservation programs, if they are complemented with conventional breeding practices.
Cedrela odorata (Meliaceae) es una especie forestal maderable nativa de América Tropical, conocida por la alta calidad de su madera. Plantaciones de esta especie son atacadas severamente por Hypsipyla grandella; la atracción o repelencia de la plaga está relacionada con metabolitos secundarios tipo fenoles y limonoides (triterpenos), por lo que el estudio de estos compuestos es importante para comprender algunos fenómenos fitoquímicos. Se evaluó la concentración de fenoles totales y limonoides en hojas de C. odorata (Meliaceae) de una plantación establecida en Tezonapa Veracruz México, se analizaron 66 individuos de siete procedencias. La concentración de fenoles y limonoides mostró diferencias significativas, no solo entre las procedencias sino también entre los árboles de una determinada procedencia (Tukey, p≤0.05). La concentración de fenoles totales varió de 49 a 223mg EAG/g e, los flavonoides de 7 a 158mg EC/g e y las proantocianidinas de 4 a 104mg EC/g e, mientras que en limonoides se obtuvieron valores de 227 a 748mg EL/g e. Mediante Cromatografía Líquida de Alta Resolución con detector UV-Arreglo de Diodos (HPLC-UV-DAD) se encontró un compuesto mayoritario que corresponde a un flavonol de tipo glicósido de Kaempferol y se identificó el flavanol catequina a bajas concentraciones. Por medio de Cromatografía de Gases-Espectrometría de Masas (CG-MS) se identificaron los sesquiterpenos β-elemeno, E-cariofileno, aromadendreno, humuleno, gama-cadineno, D-germacreno, biciclogermacreno y los poli terpenos Di-α-Tocoferol y β-sitosterol. Nuestros resultados sugieren que la evaluación de los fenoles puede desempeñar un papel importante como parámetro de selección en programas de mejora y conservación, si se complementan con las prácticas convencionales de mejoramiento genético.
Assuntos
Fenóis/análise , Flavonoides/análise , Cromatografia Líquida de Alta Pressão , Meliaceae , Cedrela , Limoninas/análise , Flavonóis/análise , Glicosídeos/análise , Folhas de Planta , MéxicoRESUMO
Drug resistance to human infectious diseases caused by pathogens lead to premature deaths through out the world. Plants are sources for wide variety of drugs used for treating various diseases. Systematic screening of medicinal plants for the search of new antimicrobial drug candidates that can inhibit the growth of pathogens or kill with no toxicity to host is being continued by many laboratories. Here we review the phytochemical investigations and biological activities of Meliaceae. The mahogany (Meliaceae) is family of timber trees with rich source for limonoids. So far, amongst the different members of Meliaceae, Azadirachta indica and Melia dubia have been identified as the potential plant systems possessing a vast array of biologically active compounds which are chemically diverse and structurally complex. Despite biological activities on different taxa of Meliaceae have been carried out, the information of antibacterial and antifungal activity is a meager with exception to Azadirachta indica. Together we provide new insights of Meliaceae members demonstrating as a potential source as antimicrobial agents using in vitro studies.
RESUMO
BACKGROUND: Limonoids are highly oxygenated compounds with a prototypical structure. Their occurrence in the plant kingdom is mainly confined to plant families of Meliaceae and Rutaceae. Owing to their wide range of pharmacological and therapeutic properties, this study was aimed at investigating the potential nitric oxide (NO) and acetylcholinesterase (AChE) inhibitory activity and the cytotoxicity of three limonoids: trichilia lactone D5 (1), rohituka 3 (2) and dregeanin DM4 (3), isolated from Trichilia welwitschii C.DC. RESULTS: Results indicated that the three limonoids had low cytotoxicity towards Vero cells with LC50 values ranging from 89.17 to 75.82 µg/mL. Compounds (2) and (3) had lower cytotoxicity compared to puromycin and doxorubicin used as reference cytotoxic compounds. Compound (1) (LC50 of 23.55 µg/mL) had good antiproliferative activity against RAW 264.7 cancer cells. At the lowest concentration tested (0.5 µg/mL), compound (2) and (3) released the lowest amount of nitric oxide (2.97 and 2.93 µM, respectively). The three limonoids had anti-AChE activity with IC50 values ranged of 19.13 µg/mL for (1), 34.15 µg/mL for (2) and 45.66 µg/mL for (3), compared to galantamine (IC50 of 8.22 µg/mL) used as positive control. CONCLUSION: The limonoid compounds studied in this work inhibited nitric oxide production in LPS-stimulated macrophages and had anti-AChE activity. Trichilia lactone D5 had potential antiproliferative activity against RAW 264.7 cancer cells. The limonoids had low cytotoxicity towards Vero cells lines. This study provided further examples of the importance of limonoids compounds as potential AChE inhibitors and anti-inflammatory agents targeting the inhibition of NO production.
Assuntos
Animais , Camundongos , Inibidores da Colinesterase/farmacologia , Meliaceae/química , Limoninas/farmacologia , Óxido Nítrico/antagonistas & inibidores , Células Vero , Chlorocebus aethiops , Lipopolissacarídeos , Concentração Inibidora 50 , Limoninas/isolamento & purificação , Limoninas/análise , Proliferação de Células/efeitos dos fármacos , Células RAW 264.7 , Lactonas/análise , Lactonas/farmacologia , Dose Letal Mediana , Macrófagos/efeitos dos fármacos , Anti-Inflamatórios/farmacologia , Óxido Nítrico/análiseRESUMO
Six new methyl angolensate type (1-6) and three new mexicanolide-type (7-9) limonoids, along with six known limonoids (10-15), were isolated from the seeds of Cipadessa baccifera. The structures of all these compounds were established by extensive 1D, 2D NMR, and HRESIMS experiments, and structures of 11 and 13 were further confirmed by a single crystal X-ray diffraction analysis, which are reported for the first time. The cytotoxic activities of these isolates were also studied against A549, MCF7, ME-180, HT-29, B-16, ACHN cancer cell lines using MTT assay, and results indicated that compounds 4, 10, and 14 displayed potent cytotoxic activity against B-16, ACHN cell lines with an IC50 values of 8.51 and 7.0 µg/mL, respectively.