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1.
J Asian Nat Prod Res ; 22(2): 99-120, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30047298

RESUMO

A large number of remarkable studies on the secondary metabolites of fungi have been conducted in recent years. This review gives an overview of one hundred and sixty-seven molecules with novel skeletons and their bioactivities that have been reported in seventy-nine articles published from 2013 to 2017. Our statistical data showed that endophytic fungi and marine-derived fungi are the major sources of novel bioactive secondary metabolites.


Assuntos
Endófitos , Fungos , Estrutura Molecular
2.
J Nat Prod ; 82(11): 2953-2962, 2019 Nov 22.
Artigo em Inglês | MEDLINE | ID: mdl-31710490

RESUMO

Six new nonadride derivatives (1-6) and three new spirocyclic anhydride derivatives (7-9) were isolated from the endophytic fungus Talaromyces purpurogenus obtained from fresh leaves of the toxic medicinal plant Tylophora ovata. The structures of these compounds were determined by spectroscopic analyses including 1D and 2D NMR, HRESIMS, and ECD techniques. Maleic anhydride derivatives 1-9 were evaluated for their in vitro anti-inflammatory activities. Compound 1 showed significant inhibitory activity against NO production in LPS-induced RAW264.7 cells with an IC50 value of 1.9 µM. Compounds 2 and 6 showed moderate inhibitory activities toward XOD and PTP1b, respectively, at 10 µM with inhibition rates of 67% and 76%.

3.
J Nat Prod ; 82(5): 1063-1071, 2019 05 24.
Artigo em Inglês | MEDLINE | ID: mdl-31050424

RESUMO

Eight new cadinene-sesquiterpenes (1-8), one eudesmane-sesquiterpene (9), and three known compounds (10-13) were isolated from an endophytic fungus, Aspergillus flavus, which was isolated from a toxic medicinal plant, Tylophora ovata. Their structures were elucidated by interpretation of spectroscopic data, and absolute configurations determined according to the specific rotation and electron circular dichroism methods. Compounds 4-8, 11, and 12 exhibited latent hepatic protection effects at 10 µM, and compound 12 selectively inhibited the proliferation of MCF-7 breast cancer cells with an IC50 values of 2.6 µM.

4.
J Asian Nat Prod Res ; 21(4): 299-307, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30909734

RESUMO

Six new glycosides (1-6), together with three known ones, were isolated from the twigs and leaves of Rhododendron latoucheae. Their structures were elucidated based on the spectroscopic data, including infrared spectrometry, mass spectrometry, and nuclear magnetic resonance experiments, along with Mosher's method. In addition, all compounds were tested their antiviral (herpes simplex virus-1 and influenza A/95-359) activities.


Assuntos
Glicosídeos/isolamento & purificação , Rhododendron/química , Antivirais/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Espectroscopia de Ressonância Magnética , Folhas de Planta/química
5.
J Asian Nat Prod Res ; 21(3): 217-226, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30739491

RESUMO

Two new azafluoranthene alkaloids (1 and 2), and a new phytoecdysone (3), were isolated from the stems of Cyclea barbata Miers, together with six known compounds (4-9). Their structures were elucidated by spectroscopic data analysis and comparison with published data. This is the first report of azafluoranthene alkaloids (1 and 2) and phytoecdysones (3, 8, and 9) from Cyclea genus. In in vitro bioassay, four isolates (3, 5, 6, and 9) showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells.


Assuntos
Alcaloides/química , Antineoplásicos Fitogênicos/química , Cyclea/química , Ecdisona/química , Fitosteróis/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Ecdisona/farmacologia , Células Hep G2 , Humanos , Modelos Moleculares , Estrutura Molecular , Fitosteróis/farmacologia
6.
J Asian Nat Prod Res ; 21(6): 559-572, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30585522

RESUMO

Three new megastigmane glucosides (1-3) and two new monoterpenes (4-5), together with 14 related known compounds (6-19) were isolated from the twigs and leaves of Lyonia ovalifolia. The structures of the new compounds were determined by extensive MS, NMR, CD experiments and chemical methods. Compounds 2, 6, and 18 displayed potent antiviral activity against Coxsackie B3, with IC50 values between 6.4 and 14.6 µM. Additionally, compounds 6, 10, and 11 exhibited noteworthy anti-inflammatory activities, with inhibition rates ranging from 54.55% to 83.33% under the concentration of 10-5 M.


Assuntos
Cicloexanonas/química , Cicloexanonas/farmacologia , Ericaceae/química , Glucosídeos/química , Glucosídeos/farmacologia , Norisoprenoides/química , Norisoprenoides/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Antivirais/química , Antivirais/farmacologia , Enterovirus/efeitos dos fármacos , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Monoterpenos/química , Monoterpenos/farmacologia , Óxido Nítrico/antagonistas & inibidores , Folhas de Planta , Células RAW 264.7 , Células Vero
7.
Fitoterapia ; 133: 29-34, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30572088

RESUMO

In our on-going study to investigate components with analgesic activity, eight new grayanane diterpenoids, epoxypieristoxins A-H (1-8), along with one known compound (9) were isolated from the roots of Pieris formosa. Their structures with absolute configurations were characterized by a series of spectroscopic methods and X-ray diffraction. Notably, compounds 1-5 represented the first example of natural grayanane diterpenoids possessed a 10,14-epoxy group. Whereas, compounds 6-7 were the first example of grayanane diterpenoid with a 7,10-epoxy group. Biological assays showed that compounds 1-3 and 5-8 displayed significant analgesic activity at a dose of 5.0 mg/kg (ip) compared to the vehicle tests (p < .05).


Assuntos
Analgésicos/farmacologia , Diterpenos/farmacologia , Ericaceae/química , Raízes de Plantas/química , Analgésicos/isolamento & purificação , Animais , Diterpenos/isolamento & purificação , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia
8.
Zhongguo Zhong Yao Za Zhi ; 43(14): 2944-2949, 2018 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-30111053

RESUMO

One new compound (2S, 3S)-2,3-dihydroxybutyl 2-hydroxy-3,5,6-trimethylbenzoate (1) and six known compounds xylariphthalide A (2), convolvulol (3), cis-4-hydroxy-6-deoxytalone (4), phomoxydienes B (5), 5,6-dihydroxy-2,3,6-trimethylcyclohex-2-enone (6), trans-cyclo-(D-tryptophanyl-L-tyrosyl) (7) were isolated from Diaporthe sp., an endophytic fungus hosted in the leaves of the toxic Chinese folk medicine Tylophora ouata, using the combination methods of silica gel column chromatography, medium-pressure ODS column chromatography and RP-preparative HPLC. The structure of compound 1 was elucidated by NMR and MS data analyses. The absolute configurations were established according to the ¹H-NMR data and exciton chirality method. Compound 1 inhibited the activation of human lung fibroblasts MRC-5 cells by 64.0% at 10 µmol·L⁻¹. The MTT assay showed that compounds 2 and 4 displayed cytotoxic activity against human tumor cell lines BGC-823 cells with IC50 values of 1.5 and 8.6 µmol·L⁻¹, respectively.


Assuntos
Tylophora , Linhagem Celular Tumoral , Endófitos , Humanos , Estrutura Molecular , Folhas de Planta
9.
J Nat Prod ; 81(8): 1721-1733, 2018 08 24.
Artigo em Inglês | MEDLINE | ID: mdl-30106288

RESUMO

A hyphenated NMR technique (analytical HPLC with a DAD connected to MS, SPE, and NMR) has proven effective for the full structural analysis and identification of minor natural products in complex mixtures. Application of this hyphenated technique to the CH2Cl2-soluble fraction of Rhododendron latoucheae led to the identification of 15 new minor ursane-type 28-nortriterpenoids (1-15). Compounds 1 and 12 inhibited HSV-1 with IC50 values of 6.4 and 0.4 µM, respectively.


Assuntos
Componentes Aéreos da Planta/química , Folhas de Planta/química , Rhododendron/química , Triterpenos/química , Animais , Antivirais/química , Antivirais/farmacologia , Cromatografia Líquida de Alta Pressão , Cães , Herpesvirus Humano 1/efeitos dos fármacos , Vírus da Influenza A/efeitos dos fármacos , Células Madin Darby de Rim Canino , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Extratos Vegetais/química , Extração em Fase Sólida , Triterpenos/farmacologia , Células Vero
10.
Bioorg Chem ; 80: 519-524, 2018 10.
Artigo em Inglês | MEDLINE | ID: mdl-30005202

RESUMO

Two new 3-hydroxy-3-methylglutaryl (HMG) flavanone 7-O-diglycosides, cigranosides A and B (1 and 2), the known naringenin 7-(2''-α-rhamnosyl-6''-(3''''-hydroxy-3''''-methylglutaryl)-glucoside (melitidin, 3), their common biosynthetic precursor flavanone 7-O-diglycoside (naringin, 4), and one known flavone 7-O-diglycoside (rhoifolin, 5) were isolated from the pericarp of Citrus grandis (L.) Osbeck. The structures of these compounds were elucidated by spectroscopic and chemical techniques. The relative ratios and absolute configurations of the C-2 diastereomers of compounds 1, 2 and 4 were determined by online normal-phase HPLC-CD using a Chiralcel column. The absolute configuration of the HMG fragment in compounds 1-3 was assigned to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. The NO inhibitory activities of compounds 1-5 were evaluated using lipopolysaccharide-induced RAW264.7 cells. Compounds 1-5 were not cytotoxic to RAW264.7 cells at 10 µM.


Assuntos
Anti-Inflamatórios/química , Citrus/química , Flavanonas/química , Glicosídeos/química , Meglutol/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Flavanonas/isolamento & purificação , Flavanonas/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Meglutol/isolamento & purificação , Meglutol/farmacologia , Camundongos , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/imunologia , Células RAW 264.7 , Estereoisomerismo
11.
J Nat Prod ; 81(5): 1183-1192, 2018 05 25.
Artigo em Inglês | MEDLINE | ID: mdl-29757638

RESUMO

Three new leucothane-type (1-3), two new micrathane-type (4, 5), eight new grayanane-type diterpenoids (6-13), and four known compounds were obtained from the ethanol extract of the leaves and twigs of Rhododendron decorum. The structures were determined based on NMR spectra, quantum chemical calculations, and X-ray crystallography. The antinociceptive activities of compounds 1, 3, 4, 6, 8, 10-13, and 15-17 were evaluated via the acetic acid-induced writhing test. Compounds 1, 8, 11-13, and 15 exhibited significant antinociceptive activities. In particular, 12 and 15 were found to be effective at doses of 0.8 and 0.08 mg/kg, respectively.


Assuntos
Analgésicos/química , Diterpenos/química , Folhas de Planta/química , Rhododendron/química , Analgésicos/farmacologia , Cristalografia por Raios X/métodos , Diterpenos/farmacologia , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Ressonância Magnética Nuclear Biomolecular/métodos , Extratos Vegetais/química , Extratos Vegetais/farmacologia
12.
Fitoterapia ; 124: 80-85, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29111165

RESUMO

Three new 3-hydroxy-3-methylglutaryl (HMG) flavone 7-O-diglycosides, argutosides A-C (1-3); two new flavone 7-O-triglycosides, argutosides D-E (4-5); and one known apigenin 7-O-triglycoside (6), were isolated from the leaves of Turpinia arguta. The structures of these compounds were elucidated by spectroscopic and chemical techniques. The NO inhibitory activities of compounds 1-6 were evaluated using lipopolysaccharide-induced RAW264.7 cells. Only compound 2 showed a moderate inhibitory effect on NO production with an IC50 value of 25.74µM. Compounds 1-6 were not cytotoxic to RAW264.7 cells at 10µM.


Assuntos
Flavonas/química , Glicosídeos/química , Magnoliopsida/química , Folhas de Planta/química , Animais , Anti-Inflamatórios/química , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Células RAW 264.7
13.
Org Lett ; 19(22): 6160-6163, 2017 11 17.
Artigo em Inglês | MEDLINE | ID: mdl-29077414

RESUMO

Illisimonin A, an unprecedented sesquiterpenoid with a tricyclo[5.2.1.01,6]decane skeleton, was isolated from the fruits of Illicium simonsii. The structure and absolute configuration of 1 were determined using extensive spectroscopic evidence and electronic circular dichroism (ECD) calculations. It was determined that 1 possesses a caged 2-oxatricyclo[3,3,0,14,7]nonane ring system fused to a five-membered carbocyclic ring and a five-membered lactone ring. A plausible biogenetic pathway for 1 was proposed, and 1 showed neuroprotective effects against oxygen-glucose deprivation (OGD)-induced cell injury in SH-SY5Y cells with an EC50 value of 27.72 µM.

14.
Sci Rep ; 7(1): 7944, 2017 08 11.
Artigo em Inglês | MEDLINE | ID: mdl-28801631

RESUMO

Rhodoterpenoids A‒C (1‒3), three new rearranged triterpenoids, together with one new biogenetically related compound, rhodoterpenoid D (4), were isolated and efficiently elucidated from Rhododendron latoucheae by high-performance liquid chromatography-mass spectrometry-solid-phase extraction-nuclear magnetic resonance (HPLC‒MS‒SPE‒NMR). Compounds 1 and 2 possess an unprecedented skeleton with a 5/7/6/6/6-fused pentacyclic ring system, while compound 3 contains a unique 6/7/6/6/6-fused pentacyclic carbon backbone. Their structures were determined by extensive spectroscopic methods and electronic circular dichroism (ECD) analyses. Plausible biogenetic pathways for 1‒4 were proposed. Compounds 1 and 4 showed potential activity against herpes simplex virus 1 (HSV-1) with IC50 values of 8.62 and 6.87 µM, respectively.


Assuntos
Antivirais/química , Herpesvirus Humano 1/efeitos dos fármacos , Rhododendron/química , Triterpenos/química , Animais , Antivirais/isolamento & purificação , Antivirais/farmacologia , Cromatografia Líquida de Alta Pressão , Dicroísmo Circular , Concentração Inibidora 50 , Imagem por Ressonância Magnética , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Extração em Fase Sólida , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Células Vero
15.
Molecules ; 22(6)2017 May 23.
Artigo em Inglês | MEDLINE | ID: mdl-28545244

RESUMO

Two new phloroglucinols, lysidisides X and Y (1 and 2), and two known compounds, 2-(2-methylbutyryl)phloroglucinol 1-O-ß-d-glucopyranoside (3) and (E)-resveratrol 3-(6″-galloyl)-O-ß-d-glucopyranoside (4), have been isolated from the roots of Lysidice rhodostegia. The structures of 1 and 2 were elucidated primarily by NMR experiments. Their absolute configurations were deduced via circular dichroism (CD) data and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 exhibited significant antioxidative activities with IC50 values of 12.0 and 11.8 µM, respectively.


Assuntos
Antioxidantes/química , Fabaceae/química , Floroglucinol/química , Raízes de Plantas/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular
16.
Org Lett ; 19(4): 906-909, 2017 02 17.
Artigo em Inglês | MEDLINE | ID: mdl-28151673

RESUMO

Pierisketolide A (1) and pierisketones B and C (2 and 3), three diterpenes with an unusual A-homo-B-nor-ent-kaurane carbon skeleton, were isolated from the roots of Pieris formosa. Their structures were characterized by a series of spectroscopic methods, X-ray diffraction, and electronic circular dichroism (ECD). Pierisketolide A (1) exhibited an analgesic effect with a 45% writhe inhibition rate at a dose of 10.0 mg/kg. The plausible biosynthetic pathways of 1-3 are proposed.


Assuntos
Analgésicos/química , Diterpenos/química , Extratos Vegetais/química , Raízes de Plantas/química , Traqueófitas/química , Analgésicos/isolamento & purificação , Carbono/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Descoberta de Drogas , Humanos , Estrutura Molecular , Extratos Vegetais/isolamento & purificação , Relação Estrutura-Atividade
17.
Sci Rep ; 6: 36752, 2016 11 14.
Artigo em Inglês | MEDLINE | ID: mdl-27841292

RESUMO

Two new grayanoids, rhodomollin A (1) and rhodomollin B (2), possessing an unprecedented D-homo grayanane carbon skeleton, were isolated from the fruits of Rhododendron molle. The structures of 1 and 2 were fully characterized using a combination of spectroscopic analyses and X-ray crystallography. Rhodomollin B (2) exhibited modest activity against influenza virus A/95-359, with an IC50 value of 19.24 µM.


Assuntos
Antivirais/química , Diterpenos/química , Frutas/química , Rhododendron/química , Animais , Antivirais/isolamento & purificação , Antivirais/farmacologia , Cristalografia por Raios X , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Cães , Vírus da Influenza A Subtipo H3N2/efeitos dos fármacos , Concentração Inibidora 50 , Células Madin Darby de Rim Canino , Testes de Sensibilidade Microbiana , Modelos Moleculares , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia
19.
J Nat Prod ; 79(11): 2824-2837, 2016 11 23.
Artigo em Inglês | MEDLINE | ID: mdl-27792321

RESUMO

Eleven new 9,10-seco-cycloartan triterpene glycosides (1-11), seven new lanostane triterpene glycosides (12-18), and two new ursane triterpenoids (19-20) were isolated from the twigs and leaves of Lyonia ovalifolia. The structures of these compounds were elucidated by extensive MS and NMR spectroscopic analysis. The absolute configuration of compound 1a (the aglycone of 1) was established by X-ray crystallography, and that of C-24 in compounds 2, 7, and 12 was established by Mo2(OAc)4-induced electronic circular dichroism experiments. All compounds were evaluated for their antiviral [herpes simplex virus-1 (HSV-1), influenza A/95-359 (A/95-359), and Coxsackie B3 (CVB3)] activity. Compounds 1, 1a, 2a, 12a, 13, and 16 exhibited potent activity against HSV-1, with IC50 values from 2.1 to 14.3 µM, while compounds 1a, 2a, 12a, 13, and 12-2a exhibited potent activity against A/95-359, with IC50 values from 2.1 to 11.1 µM. In turn, compounds 1, 1a, 2a, 12a, and 13 exhibited potent activity against CVB3, with IC50 values from 2.1 to 11.1 µM.


Assuntos
Antivirais , Medicamentos de Ervas Chinesas , Ericaceae/química , Triterpenos , Animais , Antivirais/química , Antivirais/isolamento & purificação , Antivirais/farmacologia , Cristalografia por Raios X , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Glicosídeos/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Componentes Aéreos da Planta/química , Simplexvirus/efeitos dos fármacos , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Células Vero
20.
Bioorg Med Chem Lett ; 26(19): 4832-4836, 2016 10 01.
Artigo em Inglês | MEDLINE | ID: mdl-27592135

RESUMO

Three new spirobisnaphthalenes (1-3), a new, natural spirobisnaphthalene product (4), and two new 12-membered ring lactones (11-12), with six known compounds (5-10), were isolated from the seeds of Strychnos angustiflora. Their structures were elucidated by extensive spectroscopic analysis. The absolute configurations of 1-4 were assigned by computational methods. Compounds 1, 5 and 9 inhibited lipopolysaccharide-induced NO production in BV2 cells with IC50 values of 4.85, 2.05, and 1.16µM, respectively (positive control curcumin, IC50=1.42µM). This is the first report on the anti-inflammatory activities of spirobisnaphthalenes.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Naftalenos/isolamento & purificação , Naftalenos/farmacologia , Sementes/química , Strychnos/química , Animais , Linhagem Celular , Concentração Inibidora 50
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