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
Citrus fruit industrial processing generates tons of waste composed of peels, seeds and pulp. Incorrect disposal of these residues may harm the environment. The extraction of oil and bioactive compounds from citrus fruit seeds may be considered a sustainable alternative to the disposal of waste by the citrus agroindustry. In order to provide safe disposal of citrus waste an evaluation of its composition is necessary. Here we report the results of the application of a methodology to evaluate the composition the seeds of Citrus limettioides. In the first step, extraction with supercritical carbon dioxide was used. This work allowed the isolation and identification of four aglycone-type limonoids by High Performance Liquid Chromatography and Nuclear Magnetic Resonance, identified as limonin, nomilin, deacetylnomilin, and obacunone. In addition, six other polar limonoids and two glycosyl flavonoids were identified by HPLC-ESI/MS/MS.
Assuntos
Citrus , Limoninas , Limoninas/análise , Limoninas/química , Citrus/química , Espectrometria de Massas em Tandem , Polifenóis/análise , Sementes/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
Six previously undescribed intact limonoids together with four known compounds were isolated from the seeds of Trichilia lepidota subsp. schumanniana (Harms) T.D.Penn. Their structures were characterized based on one- and two-dimensional nuclear magnetic resonance spectra, infrared, ultraviolet, mass spectroscopy results, and optical rotation. All compounds were evaluated for their ability to inhibit nitric oxide production in cultures of RAW 264.7 macrophages stimulated by lipopolysaccharide, cytotoxicity and growth of Mycobacterium tuberculosis strains H37Rv and M299. The compounds 7-deacetyl-11ß,12α-diacetoxy-14,15-epoxyazadirone (5) and walsurin E (9) were the most potent in inhibiting nitric oxide production, although the compounds 1-deshydroxy-12α-acetoxymunronin N (1) and 6α,12α-dihydroxyazadirone (6) also showed controlled potential of this mediator, in addition to being potent growth inhibitors of Mycobacterium tuberculosis H37RV and M299, without cytotoxicity interference. Ring intact limonoids isolated from Trichilia lepidota subsp. schumanniana seeds are a new source of bioactive substances that may be used in the future against diseases such as tuberculosis and other processes related to inflammation.
Assuntos
Limoninas , Meliaceae , Limoninas/química , Óxido Nítrico , Meliaceae/química , Espectroscopia de Ressonância Magnética , MacrófagosRESUMO
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
New cycloartane, 22-hydroxy-25-hydroperoxycycloart-23E-en-3-one (1), along with six known analogues (2-7) and three steroids (8-10), were isolated from the leaves of Trichilia casaretti. Structures were elucidated mainly on the basis of the analysis of 1D and 2D NMR (1H and 13C) and HRESIMS spectroscopic data, involving comparison with data of the literature. The cytotoxic activities of 1-7 and 10 isolated compounds were also evaluated against human leukemia cell line Molt-4 (acute lymphoblastic) and exhibited good cytotoxic activity with IC50 values ranging from 10.62 to 21.14 µM.
Assuntos
Limoninas , Meliaceae , Triterpenos , Humanos , Limoninas/química , Meliaceae/química , Triterpenos/química , Folhas de Planta/química , Estrutura MolecularRESUMO
Assessment of the susceptibility of natural enemies of pests to selective pesticides is relevant for a sustainable agriculture with low impact on the environment. The aim of this study was to assess the toxicity of two biorational insecticides, azadirachtin and pyriproxyfen in comparison to a neonicotinoid insecticide, acetamiprid, on pupae and adults of a Neotropical strain of Eretmocerus mundus. Adult emergence and survival were evaluated as lethal effects whereas the sublethal effects were assessed through the reproductive capacity, sex ratio, and longevity of the surviving first progeny. Adult emergence from treated pupae was reduced by all three insecticides, but azadirachtin at its maximum field recommended concentration (MFRC) proved the most toxic insecticide. The survival probability of emerged adults was reduced by the three insecticides below than 50% from 2 to 5 days after the adult emergence. Malformations in nonemerged adults from treated pupal hosts were observed at the MFRC of all three insecticides. Sublethal effects on survivors from pupal treatment could be evaluated at only the lowest azadirachtin concentration. At that concentration, though azadirachtin did not affect the reproductive capacity of females, the sex ratio and the longevity of the first progeny were disrupted. The survival of parasitoid adults after adult exposure was reduced by all three insecticides, pyriproxyfen at the MFRC being the most toxic. All insecticides at their half of MFRCs induced sublethal effects in the survivors' adults, with pyriproxyfen being the most harmful to the reproductive capacity of females. In conclusion, both biorational insecticides were toxic to E. mundus.
Assuntos
Insetos/efeitos dos fármacos , Inseticidas/química , Limoninas/química , Neonicotinoides/química , Pupa/efeitos dos fármacos , Piridinas/química , Animais , Feminino , MasculinoRESUMO
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.