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1.
Bioorg Chem ; 147: 107335, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38583250

RESUMO

Fifty compounds including seven undescribed (1, 13, 18-20, 30, 31) and forty-three known (2-12, 14-17, 21-29, 32-50) ones were isolated from the extract of the twigs and leaves of Aglaia odorata with anti-neuroinflammatory activities. Their structures were determined by a combination of spectral analysis and calculated spectra (ECD and NMR). Among them, compounds 13-25 were found to possess tertiary amide bonds, with compounds 16, 17, and 19-21 existing detectable cis/trans mixtures in 1H NMR spectrum measured in CDCl3. Specifically, the analysis of the cis-trans isomerization equilibrium of tertiary amides in compounds 19-24 was conducted using NMR spectroscopy and quantum chemical calculations. Bioactivity evaluation showed that the cyclopenta[b]benzofuran derivatives (2-6, 8, 10, 12) could inhibit nitric oxide production at the nanomolar concentration (IC50 values ranging from 2 to 100 nM) in lipopolysaccharide-induced BV-2 cells, which were 413-20670 times greater than that of the positive drug (minocycline, IC50 = 41.34 µM). The cyclopenta[bc]benzopyran derivatives (13-16), diterpenoids (30-35), lignan (40), and flavonoids (45, 47, 49, 50) also demonstrated significant inhibitory activities with IC50 values ranging from 1.74 to 38.44 µM. Furthermore, the in vivo anti-neuroinflammatory effect of rocaglaol (12) was evaluated via immunofluorescence, qRT-PCR, and western blot assays in the LPS-treated mice model. The results showed that rocaglaol (12) attenuated the activation of microglia and decreased the mRNA expression of iNOS, TNF-α, IL-1ß, and IL-6 in the cortex and hippocampus of mice. The mechanistic study suggested that rocaglaol might inhibit the activation of the NF-κB signaling pathway to relieve the neuroinflammatory response.


Assuntos
Aglaia , Lipopolissacarídeos , Óxido Nítrico , Animais , Camundongos , Aglaia/química , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Óxido Nítrico/metabolismo , Estrutura Molecular , Relação Estrutura-Atividade , Relação Dose-Resposta a Droga , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Masculino , Anti-Inflamatórios não Esteroides/farmacologia , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Benzofuranos/farmacologia , Benzofuranos/química , Benzofuranos/isolamento & purificação , Linhagem Celular , Folhas de Planta/química
2.
Ying Yong Sheng Tai Xue Bao ; 35(2): 439-446, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38523102

RESUMO

Aglaia duperreana, a species with a long cultivation history, is of high ornamental value. To understand the growth and photosynthetic changes of A. duperreana seedlings under variable environmental conditions, we conducted an experiment with light intensities adjusted at 70%, 50% and 30%, crossed with three moisture treatments at 70%, 50% and 30% of field capacity, and a control group which maintained 90% light intensity and 90% field capacity. The results showed that both drought stress and shading propensity significantly inhibited the growth of A. duperreana seedlings, with stronger impacts from drought stress. The increments in stem height and ground diameter, net photosynthetic rate, transpiration rate, stomatal conductance, and chlorophyll content were decreased with the maximum declines by 71.4%, 81.2%, 93.2%, 71.5%, 70.6% and 30.4%, respectively. Under severe drought stress (30% of field capacity), partial shading (50% of translucency) appeared to lessen the detrimental effects of drought. The combination of 70% translucency and 70% field capacity was optimal, resulting in higher increments in stem height, leaf area, net photosynthetic rate, transpiration rate, and stomatal conductance. The maximum fluorescence, variable fluorescence, PSⅡ potential activity, and PSⅡ maximum light energy conversion efficiency increased and then decreased with decreasing moisture. These findings suggested that A. duperreana could adapt to drought and shading stress by modulating growth, enhancing chlorophyll content, and adjusting photosynthetic system. Maintaining translucency at 70% and field moisture capacity at 70% could promote photosynthesis, with positive consequences on growth of A. duperreana.


Assuntos
Aglaia , Plântula , Água , Fotossíntese , Clorofila , Secas , Folhas de Planta
3.
Bioorg Chem ; 144: 107147, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38280357

RESUMO

The strategy of bioactivity-guided isolation is widely used to obtain active compounds as quickly as possible. Thus, the inhibitory effects on human erythroleukemia cells (HEL) were applied to guide the isolation of the anti-leukemic compounds from Aglaia abbreviata. As a result, 19 compounds (16 steroids, two phenol derivatives, and a rare C12 chain nor-sesquiterpenoid), including 13 new compounds, were isolated and identified based on spectroscopic data analysis, single-crystal X-ray diffraction data, and electronic circular dichroism (ECD) calculations. Among them, 9 steroids exhibited good selective anti-leukemic activity against HEL and K562 (human chronic myeloid leukemia cells) cells with IC50 values between 2.29 ± 0.18 µM and 19.58 ± 0.13 µM. Notably, all the active compounds had relatively lower toxicity on the normal human liver cell line (HL-7702). Furthermore, five compounds (1, 4, 8, 10, and 19) displayed good anti-inflammatory effects, with IC50 values between 7.15 ± 0.16 and 27.1 ± 0.37 µM. An α,ß-unsaturated ketone or a 5,6Δ double bond was crucial for improving anti-leukemic effect from the structure-activity relationship analysis. The compound with the most potential, 14 was selected for the preliminary mechanistic study. Compound 14 can induce apoptosis and cause cell cycle arrest. The expression of the marker proteins, such as PARP and caspase 3, were notably effected by this compound, thus inducing apoptosis. In conclusion, our investigation implied that compound 14 may serve as a potential anti-leukemia agent.


Assuntos
Aglaia , Humanos , Aglaia/química , Apoptose , Bioensaio , Estrutura Molecular , Esteroides/farmacologia , Relação Estrutura-Atividade , Antineoplásicos/química , Antineoplásicos/farmacologia
4.
Chem Biodivers ; 21(2): e202301703, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38055204

RESUMO

Three undescribed limonoids (1-3), named aglaians G-I, and one new natural product azedaralide (4), together with nine known analogues (5-13) were isolated from the branches and leaves of Aglaia lawii by RP C18 column, silica gel column, Sephadex LH-20 column chromatography and preparative HPLC. The structures of the new compounds were elucidated by IR, HRESIMS, 1D, 2D NMR, electronic circular dichroism (ECD) calculations and X-ray crystallography diffraction analysis. The results of bioassay showed that the compound 12 exhibited potential inhibitory activity against six human tumor cell lines (MDA-MB-231, MCF-7, Ln-cap, A549, HeLa and HepG-2) with IC50 values as 8.0-18.6 µM.


Assuntos
Aglaia , Antineoplásicos , Limoninas , Humanos , Aglaia/química , Limoninas/farmacologia , Limoninas/química , Estrutura Molecular , Linhagem Celular Tumoral
5.
Molecules ; 28(13)2023 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-37446608

RESUMO

The Aglaia genus, a member of the Meliaceae family, is generally recognized to include a number of secondary metabolite compounds with diverse structures and biological activities, including triterpenoids. Among the members of this genus, Aglaia cucullata has been reported to have unique properties and thrives exclusively in mangrove ecosystems. This plant is also known to contain various metabolites, such as flavaglines, bisamides, and diterpenoids, but there are limited reports on the isolation of triterpenoid compounds from its stem bark. Therefore, this research attempted to isolate and elucidate seven triterpenoids belonging to dammarane-type (1-7) from the stem bark of Aglaia cucullata. The isolated compounds included 20S,24S-epoxy-3α,25-dihydroxy-dammarane (1), dammaradienone (2), 20S-hydroxy-dammar-24-en-3-on (3), eichlerianic acid (4), (20S,24RS)-23,24-epoxy-24-methoxy-25,26,27-tris-nor dammar-3-one (5), 3α-acetyl-cabraleahydroxy lactone (6), and 3α-acetyl-20S,24S-epoxy-3α,25-dihydroxydammarane (7). Employing spectroscopic techniques, the chemical structures of the triterpenoids were identified using FTIR, NMR, and HRESITOF-MS. The cytotoxic activity of compounds 1-7 was tested with the PrestoBlue cell viability reagent against MCF-7 breast cancer, B16-F10 melanoma, and CV-1 normal kidney fibroblast cell lines. The results displayed that compound 5 had the highest level of bioactivity compared to the others. Furthermore, the IC50 values obtained were more than 100 µM, indicating the low potential of natural dammarane-type triterpenoids as anticancer agents. These findings provided opportunities for further studies aiming to increase their cytotoxic activities through semi-synthetic methods.


Assuntos
Aglaia , Antineoplásicos , Meliaceae , Triterpenos , Aglaia/química , Meliaceae/química , Casca de Planta/química , Ecossistema , Triterpenos/química , Espectroscopia de Ressonância Magnética , Antineoplásicos/análise , Estrutura Molecular , Damaranos
6.
Phytochemistry ; 214: 113792, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37454887

RESUMO

Phytochemical study on the methanol extract of Aglaia odorata leaves resulted in the isolation of four previously undescribed compounds, including three 2,9-deoxyflavonoids and one flavonol-diamide [3 + 2] adduct, and 13 known compounds. The chemical structures of the four undescribed compounds were elucidated on the basis of their IR, HR-ESI-MS, 1D and 2D NMR, and ECD spectra. The results revealed an unprecedented 2,9-deoxyflavonoid framework, which was confirmed by TD-DFT, ECD, and GIAO 13C-NMR calculations using sorted training set methods. The 17 compounds were examined for their ability to inhibit NO production activity in cultured lipopolysaccharide-activated RAW264.7 cells with aglaodoratas A-C, odorine, and epi-odorine inhibiting NO production, with IC50 values in the range of 16.2-24.3 µM. The other investigated compounds had either weak or no activity.


Assuntos
Aglaia , Aglaia/química , Diamida/análise , Óxido Nítrico , Extratos Vegetais/química , Folhas de Planta/química , Estrutura Molecular
7.
Elife ; 122023 02 28.
Artigo em Inglês | MEDLINE | ID: mdl-36852480

RESUMO

Plants often generate secondary metabolites as defense mechanisms against parasites. Although some fungi may potentially overcome the barrier presented by antimicrobial compounds, only a limited number of examples and molecular mechanisms of resistance have been reported. Here, we found an Aglaia plant-parasitizing fungus that overcomes the toxicity of rocaglates, which are translation inhibitors synthesized by the plant, through an amino acid substitution in a eukaryotic translation initiation factor (eIF). De novo transcriptome assembly revealed that the fungus belongs to the Ophiocordyceps genus and that its eIF4A, a molecular target of rocaglates, harbors an amino acid substitution critical for rocaglate binding. Ribosome profiling harnessing a cucumber-infecting fungus, Colletotrichum orbiculare, demonstrated that the translational inhibitory effects of rocaglates were largely attenuated by the mutation found in the Aglaia parasite. The engineered C. orbiculare showed a survival advantage on cucumber plants with rocaglates. Our study exemplifies a plant-fungus tug-of-war centered on secondary metabolites produced by host plants.


Although plants may seem like passive creatures, they are in fact engaged in a constant battle against the parasitic fungi that attack them. To combat these fungal foes, plants produce small molecules that act like chemical weapons and kill the parasite. However, the fungi sometimes fight back, often by developing enzymes that can break down the deadly chemicals into harmless products. One class of anti-fungal molecules that has drawn great interest is rocaglates, as they show promise as treatments for cancer and COVID-19. Rocaglates are produced by plants in the Aglaia family and work by targeting the fungal molecule eIF4A which is fundamental for synthesizing proteins. Since proteins perform most of the chemistry necessary for life, one might think that rocaglates could ward off any fungus. But Chen et al. discovered there is in fact a species of fungi that can evade this powerful defense mechanism. After seeing this new-found fungal species successfully growing on Aglaia plants, Chen et al. set out to find how it is able to protect itself from rocoglates. Genetic analysis of the fungus revealed that its eIF4A contained a single mutation that 'blocked' rocaglates from interacting with it. Chen et al. confirmed this effect by engineering a second fungal species (which infects cucumber plants) so that its elF4A protein contained the mutation found in the new fungus. Fungi with the mutated eIF4A thrived on cucumber leaves treated with a chemical derived from rocaglates, whereas fungi with the non-mutated version were less successful. These results shed new light on the constant 'arms race' between plants and their fungal parasites, with each side evolving more sophisticated ways to overcome the other's defenses. Chen et al. hope that identifying the new rocaglate-resistant eIF4A mutation will help guide the development and use of any therapies based on rocaglates. Further work investigating how often the mutation occurs in humans will also be important for determining how effective these therapies will be.


Assuntos
Aglaia , Hypocreales , Parasitos , Animais , Substituição de Aminoácidos , Mutação
8.
Nat Prod Res ; 37(23): 3923-3934, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-36580570

RESUMO

Three new compounds (1-3), including two bisamide derivatives (1 and 2) and a lignin (3), along with 15 known compounds were isolated from Aglaia odorata. Compound 2 was a pair of enantiomers and successfully resolved into the anticipated enantiomers. Their structures were elucidated by extensive spectroscopic analysis, electronic circular dichroism (ECD) calculations, and X-ray crystallography. Three compounds showed excellent inhibitory activities on α-glucosidase with IC50 values ranging from 54.48 to 240.88 µM, better than that of the positive control (acarbose, IC50 = 590.94 µM). Moreover, compounds 3, 13, and 15 presented moderate inhibitory activities against butyrylcholinesterase. Compound 17 exhibited potent PTP1B inhibitory activity with an IC50 value of 179.45 µM. Representative active compounds were performed for the molecular docking study. Herein, we described the isolation, structure elucidation, the inhibitory effects on three enzymes, and molecular docking of the isolates from the title plant.


Assuntos
Aglaia , Aglaia/química , Aglaia/metabolismo , Simulação de Acoplamento Molecular , Butirilcolinesterase , Estrutura Molecular , alfa-Glucosidases/metabolismo , Inibidores de Glicosídeo Hidrolases/farmacologia
9.
Molecules ; 29(1)2023 Dec 20.
Artigo em Inglês | MEDLINE | ID: mdl-38202622

RESUMO

Five undescribed steroids and one sesquiterpene, named Aglaians A-F, along with sixteen known analogs, have been isolated from the branches and leaves of Aglaia lawii. Its structure was elucidated by IR, HRESIMS, 1D and 2D NMR, quantum-chemical calculations, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. The cytotoxic and antibacterial activities of six human tumor cell lines were evaluated (MDA-MB-231, MCF-7, Ln-cap, A549, HeLa, and HepG-2), and four strains of bacteria (Bacterium subtilis, Phytophthora cinnamomic, Acrogenic bacterium, and Ralstonia solanacearum). The bioassay results indicated that compounds 3 and 5 exhibited moderate antitumor activity with IC50 values ranging from 16.72 to 36.14 µM. Furthermore, compounds 3-5 possess antibacterial activities against four bacteria with MIC values of 25-100 µM.


Assuntos
Aglaia , Sesquiterpenos , Humanos , Esteroides/farmacologia , Antibacterianos/farmacologia , Linhagem Celular Tumoral , Sesquiterpenos/farmacologia
10.
Molecules ; 27(19)2022 Oct 10.
Artigo em Inglês | MEDLINE | ID: mdl-36235298

RESUMO

Two new dammarane-type triterpenoid fatty acid ester derivatives, 3ß-oleate-20S-hydroxydammar-24-en (1) and 3ß-oleate-20S,24S-epoxy-25-hydroxydammarane (2) with a known dammarane-type triterpenoid compound, such as 20S-hydroxydammar-24-en-3-on (3), were isolated from the stem bark of Aglaiaelliptica (C.DC.) Blume. The chemical structures were determined by spectroscopic methods, including FTIR, NMR (one and two-dimensional), and HRESITOF-MS analysis, as well as chemical derivatization and comparison with previous literature. Furthermore, the synthetic analog resulting from transesterification of 1 and 2 also obtained 3ß,20S-dihydroxy-dammar-24-en (4) and 20S,24S-epoxy-3ß,25-dihydroxydammarane (5), respectively. The cytotoxic effect of all isolated and synthetic analog compounds was evaluated using PrestoBlue reagent against MCF-7 breast cancer cell and B16-F10 melanoma cell lines. The 20S-hydroxydammar-24-en-3-on (3) showed the strongest activity against MCF-7 breast cancer and B16-F10 melanoma cell, indicating that the ketone group at C-3 in 3 plays an essential role in the cytotoxicity of dammarane-type triterpenoid. On the other hand, compounds 1 and 2 had very weak cytotoxic activity against the two cell lines, indicating the presence of fatty acid, significantly decreasing cytotoxic activity. This showed the significance of the discovery to investigate the essential structural feature in dammarane-type triterpenoid, specifically for the future development of anticancer drugs.


Assuntos
Aglaia , Antineoplásicos , Neoplasias da Mama , Melanoma , Meliaceae , Triterpenos , Antineoplásicos/farmacologia , Ésteres , Feminino , Humanos , Cetonas , Estrutura Molecular , Ácido Oleico , Casca de Planta , Triterpenos/química , Triterpenos/farmacologia , Damaranos
11.
Fitoterapia ; 162: 105260, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-35931289

RESUMO

Twelve sesquiterpenoids with seven different carbon skeletons, including four isodaucanes (1-4), an aromadendrane (5), a guaiane (6), a cadalane (7), two eudesmanes (8 and 9), two bisabolanes (10 and 11), and a megastigmane (12), were isolated from the twigs and leaves of Aglaia lawii (Wight) C. J. Saldanha et Ramamorthy. Of these compounds, amouanglienoids A (1) and B (2) are new isodaucane sesquiterpenoids. This is the first report of isodaucanes from the genus Aglaia, and amouanglienoid A (1) represents the first isodaucane containing a Δ7(8) double bond. Their structures were discerned from extensive spectroscopic analyses, single-crystal X-ray diffraction, and comparison of the experimental and calculated ECD data. In in vitro bioassays, compounds 1, 10, and 11 showed potent inhibitory effects against lipopolysaccharide (LPS)-induced inflammation in BV-2 microglial cells, while compound 11 exhibited considerable inhibition of PTP1B with an IC50 value of 16.05 ± 1.09 µM.


Assuntos
Aglaia , Sesquiterpenos de Eudesmano , Sesquiterpenos , Aglaia/química , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Carbono , Lipopolissacarídeos , Estrutura Molecular , Sesquiterpenos Monocíclicos , Norisoprenoides , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos de Eudesmano/química
12.
Chem Biodivers ; 19(4): e202101008, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35194923

RESUMO

Three new aglain derivatives (1-3), one known aglain derivative (4), two known rocaglamide derivatives (5 and 6), four known triterpenoids (7-10), and three steroids (11-13) were isolated from Aglaia odorata Lour. Their structures were established through the analysis of detailed spectroscopic data and electronic circular dichroism calculations. Five compounds (1 and 4-7) exhibited cytotoxic activities on human leukemia cells (HEL) and human breast cancer cells with IC50 values in the range of 0.03-8.40 µM. In particular, the cytotoxicity of compound 5 was six times stronger than that of the positive control (adriamycin) in HEL cell lines.


Assuntos
Aglaia , Antineoplásicos Fitogênicos , Antineoplásicos , Triterpenos , Aglaia/química , Antineoplásicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Dicroísmo Circular , Humanos , Estrutura Molecular , Extratos Vegetais/química , Triterpenos/química
13.
Nat Prod Res ; 36(6): 1494-1502, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33703953

RESUMO

Two new rocaglamides, 8b-O-5-oxohexylrocaglaol (1) and elaeagnin (2), together with twelve known compounds, were isolated from the bark of Aglaia elaeagnoidea and the whole tree of A. odorata. Their structures were determined using spectroscopic methods, mainly 1D and 2D NMR. Cytotoxic activity against HepG2 human liver cancer cells of the isolated compounds was evaluated in vitro using the SRB assay. Three rocaglamide derivatives, dehydroaglaiastatin (13), 8b-O-5-oxohexylrocaglaol (1) and rocaglaol (5), exhibited significant effects with IC50 values of 0.69, 4.77 and 7.37 µM, respectively.


Assuntos
Aglaia , Aglaia/química , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia
14.
Phytochemistry ; 195: 113049, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-34902704

RESUMO

Agledulines A-K, eleven previously undescribed limonoids, including eight biogenic A/D-rings-seco limonoid analogs (agledulines A-H), one D-ring-seco limonoid (agleduline I) and two A-ring-seco limonoids with a rare Δ4,28 moiety (agledulines J-K), together with twelve reported limonoids, were isolated from the fruits of Aglaia edulis. Their structures were determined by NMR data, HRESIMS, X-ray diffraction, ECD spectra and the CD exciton chirality method. Observably, the absolute configurations of agleduline A, agleduline C and nymania 2 were unambiguously elucidated by single-crystal X-ray diffraction analyses. The biological evaluation showed that agleduline C exhibited significant cytotoxic activities with IC50 values of 10.05 µM, and 11α-acetoxygedunin showed notable anti-inflammatory activity (IC50: 4.70 µM). In addition, agleduline I and 11α-acetoxygedunin reversed the multidrug resistance with IC50 values of 5.05 and 1.49 µM (RI: 4.64 and 15.77) in the MCF-7/Dox cells.


Assuntos
Aglaia , Limoninas , Meliaceae , Frutas , Humanos , Limoninas/farmacologia , Estrutura Molecular
15.
J Org Chem ; 86(16): 11263-11268, 2021 08 20.
Artigo em Inglês | MEDLINE | ID: mdl-34279107

RESUMO

Aglatestine A (1), an unprecedented 3/6/6 tricarbocyclic limonoid framework along with four biogenic A/D-seco limonoid analogues with rare ß-substituents at C-6 (2-5), was discovered from the fruits of Aglaia edulis. The structures of 1-5 along with their absolute configurations were clarified using methods of HRMS(ESI), NMR, electronic circular dichroism, X-ray diffraction crystallography, and quantum chemical calculations. The plausible biogenetic speculation suggested that an electrophilic cyclization between C-1 carbocation from acetolysis and electron-rich C-5 from enolization of C═O of 2 may play a key role. The biological evaluation showed that 5 exhibited anti-inflammatory activity indicated by inhibiting NO release in LPS-activated RAW 264.7 macrophages (IC50: 35.72 ± 1.96 µM).


Assuntos
Aglaia , Limoninas , Anti-Inflamatórios , Frutas , Limoninas/farmacologia , Macrófagos , Estrutura Molecular
16.
Planta Med ; 87(12-13): 937-948, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-33784769

RESUMO

With about 120 species, Aglaia is one of the largest genera of the plant family Meliaceae (the mahogany plants). It is native to the tropical rainforests of the Indo-Australian region, ranging from India and Sri Lanka eastward to Polynesia and Micronesia. Various Aglaia species have been investigated since the 1960s for their phytochemical constituents and biological properties, with the cyclopenta[b]benzofurans (rocaglates or flavaglines) being of particular interest. Phytochemists, medicinal chemists, and biologists have conducted extensive research in establishing these secondary metabolites as potential lead compounds with antineoplastic and antiviral effects, among others. The varied biological properties of rocaglates can be attributed to their unusual structures and their ability to act as inhibitors of the eukaryotic translation initiation factor 4A (eIF4A), affecting protein translation. The present review provides an update on the recently reported phytochemical constituents of Aglaia species, focusing on rocaglate derivatives. Furthermore, laboratory work performed on investigating the biological activities of these chemical constituents is also covered.


Assuntos
Aglaia , Benzofuranos , Austrália , Fator de Iniciação 4A em Eucariotos , Compostos Fitoquímicos/farmacologia
17.
Asian Pac J Cancer Prev ; 22(1): 53-60, 2021 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-33507679

RESUMO

BACKGROUND: The genus Aglaia (Meliaceae) is an established source of many anticancer compounds. The study evaluated the leaf extracts of Aglaia loheri, a tree native to the Philippines, as potential source of anticancer compounds. METHODS: Using bioassay-guided fractionation, A. loheri leaf extract was subjected to various chromatographic techniques and step-wise application of MTT assay on human colorectal carcinoma cells, HCT116, to determine the cytotoxic fractions. The most cytotoxic HPLC isolate was structurally identified using 1D and 2D NMR and its apoptotic effect was assessed by JC-1 staining, caspase 3/7 assay and TUNEL assay. RESULTS: After stepwise chromatography fractionation, an HPLC isolate, structurally identified as aglaforbesin derivative (AFD), demonstrated potent cytotoxicity against HCT116. AFD exhibited strong toxicity (IC50 = 1.13 ±0.07 µg/mL) and high selectivity on HCT116 than normal human kidney cells (HK-2). AFD-induced toxicity to HCT116 is possibly through the stimulation of the apoptotic signaling pathway via caspase 3/7 activation and DNA fragmentation independent of mitochondrial membrane depolarization. CONCLUSION: AFD exhibited selective cytotoxicity and apoptotic activity to HCT116 and could be further developed as anticancer drug lead.


Assuntos
Aglaia/química , Antineoplásicos Fitogênicos/farmacologia , Apoptose , Neoplasias Colorretais/patologia , Mitocôndrias/patologia , Extratos Vegetais/farmacologia , Proliferação de Células , Neoplasias Colorretais/tratamento farmacológico , Humanos , Mitocôndrias/efeitos dos fármacos , Células Tumorais Cultivadas
18.
Phytochemistry ; 183: 112651, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33418167

RESUMO

Eleven previously uncharacterized steroids, along with three analogs were isolated from Aglaia lawii leaves. Their structures were definitely characterized by the methods of NMR, MS, IR, ECD and X-ray crystallography study. Among these unreported compounds, 3-epi-dyscusin C, 3-epi-lansisterone E and (Z)-2α-hydroxyaglawone were C-21 pregnane steroids incorporating a highly oxygenated ring A, while others were Δ5-3ß-hydroxy-7-ketosteroids bearing different ring D and C-17 aliphatic chains. All isolates were evaluated for nitric oxide (NO) inhibitory activities. 3-Epi-dyscusin C, 3-epi-lansisterone E, (Z)-2α-hydroxyaglawone and 17(20)E-dyscusin B showed significant anti-inflammatory activities with IC50 values of NO inhibition less than 10 µM (in the range from 4.47 ± 0.36 to 7.67 ± 0.46 µM).


Assuntos
Aglaia , Estrutura Molecular , Óxido Nítrico , Folhas de Planta , Pregnanos/farmacologia , Esteroides/farmacologia
19.
J Asian Nat Prod Res ; 23(8): 781-788, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-32536210

RESUMO

A seco-apotirucallane-type triterpenoid, namely angustifolianin (1), along with three dammarane-type triterpenoids, (20S, 24S)-epoxy-dammarane-3ß,25-diol (2), 3-epi-cabraleahydroxylactone (3), and cabralealactone (4), were isolated from the stem bark of Aglaia angustifolia Miq. The Chemical structure of the new compounds was elucidated on the basis of spectroscopic data. All of the compounds were evaluated for their cytotoxic effects against MCF-7 breast cancer cells. Among those compounds, angustifolianin (1) showed strongest cytotoxic activity with an IC50 value of 50.5 µg/ml.


Assuntos
Aglaia , Antineoplásicos , Triterpenos , Estrutura Molecular , Casca de Planta , Triterpenos/farmacologia
20.
Phytochemistry ; 181: 112540, 2021 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-33130371

RESUMO

Aglaia is the largest genus in the Meliaceae family (also known as Mahagoni in Indonesia), consisting of over 150 species, of which 65 are indigenous to Indonesia. These species spread through the tropical regions, especially Southeast Asia as well as the Nothern part of Australia, and have been used in traditional medicine for the treatment of several diseases. However, preliminary chemical researches commenced in 1965, where dammarane-type triterpenoids, aglaiol was isolated, and the structure was determined by chemical reaction and spectroscopic methods. Several studies have been carried out on the stembark, bark, leaves, seeds and leaves in the last fifty five years, and about 291 metabolites have been isolated from the sesquiterpenoid, diterpenoid, triterpenoid, limonoid, steroid, lignan, and alkaloid groups, as well as flavagline, which known to be the largest. This specifically amounts to 34% of Aglaia species, reported to show cytotoxic and insecticidal potentials, and also the tendency for use as chemical markers for this species. The extracts and compounds obtained from Aglaia species are evaluated for potential biological activities, including cytotoxicity, insecticidal, anti-inflammatory, antifungal, molluscicidal, antituberculosis and antiviral effects. In addition, flavagline (rocaglamide) derivatives have been confirmed to exhibit exceptional cytotoxicity, and are, thus, considered lead compounds for further development. Therefore, the results support the concept of utilizing Aglaia species as a potential source for the production of biologically active compounds.


Assuntos
Aglaia , Produtos Biológicos , Austrália , Indonésia , Estrutura Molecular
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