RESUMO
Nine metabolites, including three undescribed alkaloids pyripyropenes VW (1-2), penicioxa A (4), two previously reported pyripyropene A (3), oxaline (5), three grisephenone-type xanthone derivatives (6-8), and a diphenyl ether derivative 4-chloro-7,4'-dihydroxy-5,2'-dimethoxy-2-methylformate-6'-methybenzophone (9), were isolated from cultures of the mangrove-derived fungus Penicillium robsamsonii HNNU0006. Their structures were determined by spectroscopic analysis, ECD calculations, together with DP4+ probability analysis. Furthermore, all the isolated compounds were tested for cytotoxicity and anti-phytopathogenic fungal activities. Compounds 6-8 showed moderate cytotoxicity against tumor cell lines A549, with IC50 values ranging from 5.68 ± 0.21 to 9.71 ± 0.34 µg/mL, respectively.
Assuntos
Alcaloides , Penicillium , Penicillium/química , Estrutura Molecular , Humanos , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Alcaloides/química , Células A549 , Antineoplásicos/farmacologia , Antineoplásicos/isolamento & purificação , Antineoplásicos/química , China , Rhizophoraceae/microbiologiaRESUMO
The phytochemical investigation on the fruits of Morinda citrifolia led to the isolation and characterization of a new anthraquinone, moricitrifone (1), along with seven known anthraquinones (2-8). The chemical structure of 1 was elucidated by extensive spectral analyses. The known compounds (2-8) were identified by comparing their spectral data with those reported in the literature. The antiproliferative activities of all isolated anthraquinones (1-8) against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 were evaluated in vitro. Compounds 1-8 exhibited remarkable antiproliferative activities with IC50 values ranging from 0.26 ± 0.05 to 16.58 ± 0.18 µM, which were comparable to those of doxorubicin.
Assuntos
Morinda , Humanos , Morinda/química , Estrutura Molecular , Frutas/química , Extratos Vegetais/química , Antraquinonas/químicaRESUMO
Six new limonoids, named hainanxylogranolides A-F (1-6), together with nineteen known ones (7-25) were isolated from the seeds of a Hainan mangrove Xylocarpus granatum. The structures of the new compounds were established by extensive NMR spectroscopic data combined with the DFT and TDDFT calculated electronic circular dichroism spectra. Hainanxylogranolide A (1) is the aromatic B-ring limonoid containing a central pyridine ring and a C-17 substituted γ(21)-hydroxybutenolide moiety. Hainanxylogranolide B (2) belongs to the small group of mexicanolides containing a C3-O-C8 bridge, whereas hainanxylogranolides C and D (3 and 4) are mexicanolides comprising a C1-O-C8 bridge. Compounds 9 and 25 posed obvious inhibition effect on the tube formation of HUVECs. There are only about 25% tube-like structures were observed at the concentration of 40.0 µM of compound 25. The antiviral activities of the isolates against herpes simplex virus-1 (HSV-1) and severe fever with thrombocytopenia syndrome virus (SFTSV) were tested in vitro. Compound 23 exhibited moderate anti-SFTSV activity with the IC50 value of 29.58 ± 0.73 µM. This is the first report of anti-angiogenic effect and anti-SFTSV activity of limonoids from the genus Xylocarpus.
Assuntos
Limoninas , Meliaceae , Estrutura Molecular , Cristalografia por Raios X , Antivirais/farmacologia , Sementes/química , Meliaceae/químicaRESUMO
The present study investigated the chemical constituents and inhibitory activities against α-glucosidase from the seeds of Morinda citrifolia(Noni) by the chromatographic technique and semi-preparative HPLC.Fifteen compounds were isolated from the ethyl acetate extract of the seeds, and their structures were identified on the basis of physiochemical characteristics and spectroscopic data as(9S,2E,4Z,7Z)-9-hydroxydeca-2,4,7-trienoic acid(1), azelaic acid(2), scopoletin(3), ursolic acid(4), quercetin(5), cyclo-(L-Leu-L-Ile)(6), cyclo-(L-Phe-L-Ile)(7), cyclo-(L-Phe-L-Val)(8), cyclo-(L-Leu-L-Val)(9), cyclo-(L-Phe-L-Leu)(10), caffeic acid(11), 3,4-dihydroxycinnamaldehyde(12), p-hydroxybenzoic acid(13), p-hydroxy-cinnamic acid(14), and p-hydroxyphenethyl alcohol(15).Among them, compound 1 was a new fatty acid and compounds 7-10 and 12 were isolated from Morinda plant in the Rubiaceae family for the first time.Compounds 1, 2 and 4-15 were isolated from the seeds of M.citrifolia(Noni) for the first time.All isolated compounds were evaluated for the inhibitory activities against α-glucosidase and compounds 3-5 showed potential inhibitory activity with IC_(50) values of 160, 133, and 120 µmol·L~(-1), respectively.
Assuntos
Morinda , Frutas/química , Morinda/química , Extratos Vegetais/química , Escopoletina , Sementes/química , alfa-GlucosidasesRESUMO
A new isoflavone (Z)-5,7,4'-trihydroxy-3'-[3-hydroxy-3-methyl-1-butenyl] isoflavone (1) together with seven known isoflavones (2-8) were isolated from the fruits of the Ficus auriculata. Their structures were established on the basis of 1 D, 2 D-NMR spectroscopic data and HR-ESI-MS analysis. All compounds were evaluated for their antibacterial activities against five pathogenic bacteria in vitro. Compounds 3 and 4 exhibited significant antibacterial activities against five pathogenic bacteria with the MIC values ranging from 1.25 to 20 µg/mL.[Formula: see text].
Assuntos
Ficus , Isoflavonas , Antibacterianos/química , Ficus/química , Frutas/química , Isoflavonas/química , Estrutura Molecular , Extratos Vegetais/químicaRESUMO
Banana flowers are consumed as a vegetable and traditionally used for managing several health problems including joint pain, a symptom of bone loss. Osteoclasts are key effector cells responsible for bone loss. Some flavonoids in banana flowers, such as quercetin and quercitrin, have been shown to be able to inhibit osteoclastogenesis. Whether banana flowers can inhibit osteoclast formation is unknown. In this study, we prepared the ethyl acetate fraction (FFE-EA) of an ethanolic extract of fresh flowers of Musa nana. Using UPLC-MS/MS analyses, 76 polyphenols were identified in FFE-EA. In RANKL-stimulated RAW264.7 macrophages, FFE-EA inhibited osteoclastogenesis and osteoclastic bone resorption. Mechanistic studies revealed that FFE-EA suppressed NF-κB and MAPK pathways, and lowered mRNA levels of osteoclast formation/function-related genes. These findings suggest that flowers of M. nana could be a source for formulating functional food that benefits bone health.
Assuntos
Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Musa/química , Osteoclastos/efeitos dos fármacos , Osteogênese/efeitos dos fármacos , Extratos Vegetais/farmacologia , Acetatos , Animais , Flores/química , Camundongos , NF-kappa B/metabolismo , Células RAW 264.7RESUMO
Two novel aporphine-derived alkaloids, aporaloids A and B (1 and 2), together with eight known biogenetically related alkaloids (3-10), two known isoquinoline alkaloids (3 and 4), and six known aporphinoid alkaloids (5-10) were isolated from the stems of Fissistigma glaucescens. Their structures were elucidated using comprehensive spectroscopic methods. Compounds 1 and 2 represent the rare example of a six-membered lactone ring aporphine-derived alkaloids from natural products. The inhibitory activities of all compounds against four cancer cell lines were evaluated. Aporaloids A and B (1 and 2) showed broad spectrum cytotoxic activities.
Assuntos
Annonaceae/química , Antineoplásicos Fitogênicos/farmacologia , Aporfinas/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Aporfinas/isolamento & purificação , Linhagem Celular Tumoral , China , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Caules de Planta/químicaRESUMO
Four new alkaloids, nonialkaloids A-D (1-4) and six known analogues (5-10) were isolated from the noni juice. Among the new compounds, 1 and 2 are indole alkaloids with a seven-membered fused N-heterocyclic ring, 3 and 4 are quaternary ammonium derivatives. The structures were elucidated by extensive NMR and MS analysis, while the absolute configurations of the stereogenic carbons were established based on quantum-chemical electronic circular dichroism calculations or the modified Mosher's method. All the isolates were tested for α-glucosidase inhibitory activities. Compounds 1 and 3 displayed potent inhibitory activity against α-glucosidase with the IC50 values of 413.7 and 364.4 µM, respectively.
Assuntos
Inibidores de Glicosídeo Hidrolases/farmacologia , Alcaloides Indólicos/farmacologia , Morinda/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Alcaloides Indólicos/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologiaRESUMO
The chemical constituents from the stems and leaves of Morinda citrifolia were isolated and purified by column chromatography methods with silica gel, ODS, Sephadex LH-20 and preparative high performance liquid chromatography(HPLC). The structures of the isolated compounds were identified by physicochemical properties and spectroscopic analysis, as well as comparisons with the data reported in literature. 17 compounds were isolated from the 90% ethanol extract of the stems and leaves of M. citrifolia, and were identified as 9,10-dihydroxy-4, 7-megastigmadien-3-one(1), 5,12-epoxy-6,9-hydroxy-7-megastigmen-3-one(2), fukinone(3), ß-eudesmol(4), sarmentol F(5), 4, 5-dihydroblumenol A(6), 3-hydroxy-ß-ionone(7), aristol-8-en-1-one(8), ergosta-7-en-3ß-ol(9), ergosta-7-ene-3ß,5α,6ß-triol(10),(22E)-5α,8α-epidioxyergosta-6,22-dien-3ß-ol(11), olivil(12), 4-epi-larreatricin(13), chushizisin â (14), rabdosia acid A(15), glycerol monolinoleate(16) and(9Z,12Z,15Z)-2,3-dihydroxypropyl octadeca-trienoate(17). All compounds were isolated from M. citrifolia for the first time. All isolated compounds were evaluated for their anti-rheumatoid arthritis activities via examining their inhibitory activities on the proliferation of synoviocytes in vitro using MTS met-hod. Compounds 1-11 showed significant anti-rheumatoid arthritis activities, displaying the inhibitory effects on the proliferation of MH7 A synovial fibroblast cell with the IC_(50) values ranging from(38.69±0.86) to(203.45±1.03) µmol·L~(-1).
Assuntos
Morinda , Sinoviócitos , Proliferação de Células , Cromatografia Líquida de Alta Pressão , Estrutura MolecularRESUMO
Nine secondary metabolites(S)-5-hydroxy-4-methylchroman-2-one(1), 4-methoxynaphthalene-1,5-diol(2), 8-methoxynaphthalene-1,7-diol(3), 1,8-dimethoxynaphthalene(4),(2R,4S)-2,3-dihydro-2-methyl-benzopyran-4,5-diol(5),(2R,4R)-3,4-dihydro-4-methoxy-2-methyl-2H-1-benzopyran-5-ol(6), 7-O-α-D-ribosyl-2,3-dihydro-5-hydroxy-2-methyl-chromen-4-one(7),(R)-3-methoxyl-1-(2,6-dihydroxyphenyl)-butan-1-one(8) and helicascolide A(9) were isolated from endophytic fungus Cladosporium sp. JJM22 by using column chromatographies of silica gel and ODS, and semi-preparative HPLC. Their structures were analyzed on the basis of spectroscopic and chemical data, especially NMR and MS. All isolated compounds were evaluated for their anti-inflammatory activities by examining the inhibitory activities on nitric oxide(NO) production induced by lipopolysaccharide in mouse macrophage RAW264.7 cells in vitro. Compounds 2-4 showed inhibitory activities.
Assuntos
Rhizophoraceae , Animais , Benzopiranos , Cladosporium , Fungos , Camundongos , Estrutura MolecularRESUMO
The phytochemical investigation of the stems of Homalium stenophyllum afforded seven new phenolic glycosides (1-5 and 8-9) and two known compounds (6 and 7). Their structures were elucidated by comprehensive analyses of NMR spectroscopic, mass spectrometric data and chemical hydrolysis. Additionally, their anti-inflammatory activities against the NO production in LPS-induced macrophages were evaluated.
Assuntos
Glicosídeos , Fenóis , Salicaceae/química , Anti-Inflamatórios/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Macrófagos/efeitos dos fármacos , Estrutura Molecular , Fenóis/isolamento & purificação , Fenóis/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Caules de Planta/químicaRESUMO
Four new cyclohexene derivatives cladoscyclitols A-D (1-4) and one new ribofuranose phenol derivative 4-O-α-D-ribofuranose-2-pentyl-3-phemethylol (5) were obtained from the EtOAC extract of the mangrove-derived endophytic fungus Cladosporium sp. JJM22. The structures were elucidated by extensive NMR and MS analysis, while the absolute configurations of the stereogenic carbons were established based on quantum-chemical electronic circular dichroism calculations or comparison of the optical rotations with those of related compounds. Compounds 2 and 5 displayed potent inhibitory activity against α-glucosidase with the IC50 values of 2.95 and 2.05 µM, respectively.
Assuntos
Cladosporium/química , Cicloexenos/farmacologia , Inibidores de Glicosídeo Hidrolases/farmacologia , Rhizophoraceae/microbiologia , China , Cicloexenos/isolamento & purificação , Endófitos/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura MolecularRESUMO
Three new methylated Δ8-pregnene steroids, stemphylisteroids A-C (1-3) were isolated from the medicinal plant Polyalthia laui-derived fungus Stemphylium sp. AZGP4-2. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. The absolute configuration of 1 was determined by X-ray crystallographic analysis. Compound 1 show antibacterial activity against Escherichia coli with the MIC value of 6.25⯵g/mL, and 2 exhibited a broad spectrum of antibacterial activities against six pathogenic bacteria with the MIC values ranging from 12.5 to 50⯵g/mL. The discovery of three methylated Δ8-pregnene steroids 1-3 are a further addition to diverse and complex array of methylated steroids.
Assuntos
Antibacterianos/farmacologia , Ascomicetos/química , Escherichia coli/efeitos dos fármacos , Polyalthia/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Metilação , Testes de Sensibilidade Microbiana , Modelos Moleculares , Conformação Molecular , Relação Estrutura-AtividadeRESUMO
A new triterpenoid glucoside, leuctriterpencoside (1), along with two known compounds (2-3) were isolated from Leucas zeylanica. The structure of the new compound was elucidated using comprehensive spectroscopic methods. Compound 1 showed significant inhibitory activity against α-glucosidase (IC50 value of 0.85 ± 0.12 µM).
Assuntos
Glucosídeos/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Lamiaceae/química , Triterpenos/isolamento & purificação , Glucosídeos/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Lamiaceae/metabolismo , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Triterpenos/química , alfa-Glucosidases/efeitos dos fármacos , alfa-Glucosidases/metabolismoRESUMO
The present work was launched to study the chemical constituents from fermented Noni juice. Ten compounds were isolated by using silicagel,Sephadex LH-20 and pre-HPLC. The structures of these compounds were identified by 1D and 2D NMR. Their structures were established as norimester( 1),cyclo( R-Pro-S-Phe)( 2),cyclo-( L-Pro-L-Leu)( 3),trans-cyclo-( D-tryptophanyl-Ltyrosyl)( 4),cyclo( L-Trp-N-methyl-L-Ala-)( 5),4-allyl-2-hydroxyphenyl 1-O-ß-D-apiosyl-( 1 â 6)-ß-D-glucopyranoside( 6),2-methoxy-4-vinylphenyl ß-D-apiofuranosyl-( 1â6)-ß-D-glucopyranoside( 7),( +)-lirioresinol A( 8),( ±)-syringaresinol( 9),and2-formyl-1 H-pyrrole-1-butanoic acid( 10). All compounds were tested for their antibacterial activity and α-glucosidase inhibitory activity. Compound 1 was a new compound. All compounds were isolated from fermented Noni juice for the first time. Compound 1 showed significant inhibitory activity against α-glucosidase [IC50 value of( 4. 22±0. 03) µmol·L-1].
Assuntos
Alimentos Fermentados/análise , Sucos de Frutas e Vegetais/análise , Morinda/química , Compostos Fitoquímicos/análise , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância MagnéticaRESUMO
Two novel epimer pairs of acetaminophen derivatives penicilquei A-D (1-4) were isolated from Penicillium herquei JX4. Their structures were elucidated using comprehensive spectroscopic methods. The absolute configurations of penicilquei A-D (1-4) were determined by modifified Mosher's method, and comparing their experimental and calculated electronic circular dichroism (ECD) spectra. Penicilquei A-D (1-4) are the first example of acetaminophen derivatives featuring an unprecedented carbon skeleton. The inhibitory activities of all compounds against nine phytopathogenic fungi and α-glucosidase were evaluated. Penicilquei A-D (1-4) showed strong inhibitory activities against at least eight phytopathogenic fungus.
Assuntos
Acetaminofen/farmacologia , Fungicidas Industriais/farmacologia , Penicillium/química , Acetaminofen/química , China , Fungicidas Industriais/química , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Estrutura Molecular , Rhizophoraceae/microbiologiaRESUMO
Two new compounds penibenzophenones A-B (1-2), and the synthetic α,ß-unsaturated amide alkaloid (E)-tert-butyl(3-cinnamamidopropyl)carbamate (4), newly identified as a natural product, alone with three known ones (3, 5-6) were isolated from the EtOAc extract of the endophytic fungus Penicillium citrinum HL-5126 isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Compound 1 was a chlorinated benzophenone. The structures of 1-6 were elucidated by extensive NMR spectral interpretation, MS data and X-ray analysis. The new compound 2 displayed cytotoxic activity against human A549 cell lines with an IC50 value of 15.7 µg/mL, and 1 showed antibacterial activity against Staphylococcus aureus with a MIC value of 20 µg/mL.
Assuntos
Alcaloides/farmacologia , Antibacterianos/farmacologia , Benzofenonas/farmacologia , Penicillium/química , Células A549 , Alcaloides/química , Alcaloides/isolamento & purificação , Amidas/química , Antibacterianos/isolamento & purificação , Benzofenonas/isolamento & purificação , Cristalografia por Raios X , Avaliação Pré-Clínica de Medicamentos/métodos , Endófitos/química , Humanos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Rhizophoraceae/microbiologia , Staphylococcus aureus/efeitos dos fármacos , Áreas AlagadasRESUMO
One new lignan derivative 2,3-dimethyl-4-(4'-hydroxy-3',5'-dimethoxyphenyl)-6-hydroxy-7-methoxy-naphthalene (1), together with four known analogues (2-5), were isolated from acetone extract of the fruiting bodies of Ganoderma lipsiense collected in the Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compound 1 showed insecticidal activity against newly hatched karvae of Helicoverpa armigera Hubner. Compounds 1-5 showed moderate antibacterial activity against Staphylococcus aureus with the same MIC value of 1.25 µg/mL.
Assuntos
Antibacterianos/farmacologia , Ganoderma/química , Inseticidas/farmacologia , Lignanas/farmacologia , Animais , Antibacterianos/química , China , Avaliação Pré-Clínica de Medicamentos , Carpóforos/química , Inseticidas/química , Lignanas/química , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Mariposas/efeitos dos fármacos , Espectrometria de Massas por Ionização por Electrospray , Staphylococcus aureus/efeitos dos fármacosRESUMO
One new norisoprenoid 3,9-dihydroxy dihydro actinidiolide (1), together with eleven known compounds (2-12), were isolated from ethanol extract of the leaves of Ficus pumila collected in Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compounds 1, 2, 4, 5, 8 and 10-12 were isolated from the F. pumila for the first time. All compounds were evaluated for their cytotoxic activity. Compounds 3 and 9 showed weak cytotoxic activity against Hela, MCF-7 and A549 cell lines.
Assuntos
Ficus/química , Norisoprenoides/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Norisoprenoides/química , Extratos Vegetais/análise , Folhas de Planta/químicaRESUMO
A new fatty acid methyl ester (1) was isolated from an EtOH extract of Fissistigma oldhamii. It structures was elucidated by a combination of HR-ESI-MS, 1D NMR, 2D NMR, UV, and IR spectroscopic data. The inhibitory effect of compound 1 on the proliferation of primary synovial cells was evaluated. As a result, it showed inhibitory effect on the proliferation of synoviocytes, with IC50 value of 38.6 µmol·L⻹.