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1.
Chem Biodivers ; 16(12): e1900495, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31755643

RESUMO

Fifteen diterpenoids (1-15), including three undescribed ones with ent-atisane skeleton, eupnerias G-I (1-3), were obtained from Euphorbia neriifolia. Compounds 1-3 were established through comprehensive spectroscopic analysis. Compounds 4 and 5 exhibited obvious anti-HIV-1 effect, and their EC50 were 6.6±3.2 and 6.4±2.5 µg mL-1 , respectively. Compound 6 exhibited moderate cytotoxicity on HepG2 and HepG2/Adr cells with IC50 at 13.70 and 15.57 µm, respectively. In addition, compound 15 exhibited significant cytotoxicity on HepG2 cell lines (IC50 =0.01 µm), while it did not show any cytotoxicity against HepG2/Adr cell lines.

2.
J Inorg Biochem ; 203: 110909, 2019 Oct 29.
Artigo em Inglês | MEDLINE | ID: mdl-31689591

RESUMO

Glioma stem cells (GSCs) are thought to be responsible for the recurrence and invasion of glioblastoma multiform (GBM), which have been evaluated and exploited as the therapeutic target for GBM. Cyclometalated iridium(III) complexes have been demonstrated as the potential anticancer agents, however, their antitumor efficacies against GSCs are still unknown. Herein, we investigated the antitumor activity of two cyclometalated iridium(III) complexes [Ir(ppy)2L](PF6) (Ir1) and [Ir(thpy)2L](PF6) (Ir2) (ppy = 2-phenylpyridine, thpy = 2-(2-thienyl)pyridine and L = 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine) against GSCs. The results clearly indicate that Ir1 and Ir2 kill GSCs selectively with IC50 values ranging from 5.26-9.05 µM. Further mechanism research display that Ir1 and Ir2 can suppress the proliferation of GSCs, penetrate into GSCs efficiently, localize to mitochondria, and induce mitochondria-mediated apoptosis, including the loss of mitochondrial membrane (MMP), elevation of intracellular reactive oxygen species (ROS) and caspases activation. Moreover, Ir1 and Ir2 can destroy the GSCs self-renewal and unlimited proliferation capacity by affecting the GSCs colony formation. According our knowledge, this is the first study to investigate the anti-GSCs properties of cyclometalated iridium(III) complexes.

3.
Molecules ; 24(16)2019 Aug 13.
Artigo em Inglês | MEDLINE | ID: mdl-31412677

RESUMO

Five new cucurbitane-typetriterpenoid glycosides, named Xuedanoside F-J (1-5), were obtained from the rhizomes of Hemsleya penxianensis (Xue dan), which belongs to the family of Cucurbitaceae. These new compounds were elucidated byspectroscopic analysis, including 1D, 2D NMR, and HR-ESI-MS spectra. Additionally, all the isolates were evaluated for cytotoxicity against three human cancer cell lines (Hela, MCF-7, and A-549) with the IC50 ranging from 2.25 to 49.44 µM in vitro with treatment 48 h and showed low cytotoxicity in human normal liver L-02 cells (IC50 > 50 µM). Compound 5 showed the most significant cytotoxic activity with the IC50 value of 2.25, 4.72, and 5.33 µM in 48 h, respectively.

4.
Chem Biodivers ; 16(5): e1800474, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30801931

RESUMO

Twelve 3,8-epoxy iridoids, including four new compounds, jatamanins R-U (1-4), and eight known compounds (5-12), were obtained from the roots and rhizomes of Valeriana jatamansi. The structures were elucidated from analysis of spectroscopic data. The absolute configurations of 1-4 were determined by comparison of experimental and literature ECD spectra. Moreover, the compounds were evaluated for cytotoxic effects against glioma stem cells, inhibition of NO production, activity against influenza A virus and reversal of multidrug resistance of HepG2/ADR cells. Compounds 9 and 12 showed significant cytotoxic potency against GSC-18# (IC50 =1.351 and 4.439 µg ml-1 , respectively) and GSC-3# (IC50 =10.88 and 6.348 µg ml-1 , respectively) glioma stem cells, while compound 12 was also slightly less potent against GSC-12# (IC50 =13.45 µg ml-1 ) glioma stem cell growth. In addition, compounds 9 and 12 displayed obvious inhibition of NO production (IC50 =4.6 and 15.8 µm, respectively).


Assuntos
Iridoides/química , Valeriana/química , Animais , Proliferação de Células/efeitos dos fármacos , Dicroísmo Circular , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Células Hep G2 , Humanos , Iridoides/isolamento & purificação , Iridoides/farmacologia , Lipopolissacarídeos/toxicidade , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Conformação Molecular , Óxido Nítrico/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Células RAW 264.7 , Relação Estrutura-Atividade , Valeriana/metabolismo
5.
Nat Prod Res ; : 1-9, 2019 Jan 29.
Artigo em Inglês | MEDLINE | ID: mdl-30691300

RESUMO

Six new compounds, including three terpenoids (1-3) and three lignans (4-6), were isolated from the 95% EtOH extract of the twigs of Tripterygium hypoglaucum. Their structures were determined on the basis of extensive spectroscopic analysis. 9'-O-benzoyl-lariciresinol (4) showed weak cytotoxicity against HepG2/Adr cells, with an IC50 value of 30.1 µM in vitro.

6.
Nat Prod Res ; 33(21): 3083-3088, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30427740

RESUMO

A new protostane-type triterpenoid bearing an oxetane ring in the side-chain, named alisol W (1), has been obtained from the dried rhizome of Alisma plantago-aquatica subsp. orientale. The structure and absolute configuration of compound 1 was determined from extensive spectroscopic analysis. In addition, the vasorelaxant activity and the inhibition on 11ß-HSD1 of compound 1 were also evaluated, however, it didn't show remarkable effects.


Assuntos
Alisma/química , Triterpenos/isolamento & purificação , 11-beta-Hidroxiesteroide Desidrogenase Tipo 1/antagonistas & inibidores , Humanos , Estrutura Molecular , Rizoma/química , Análise Espectral , Triterpenos/química , Vasodilatadores/análise
7.
Nat Prod Res ; 33(2): 219-225, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29495881

RESUMO

Actinomycin Z6 (1), a new member of the actinomycin family, along with three congeners of the Z-type (Z1, Z3, Z5) actinomycins, are produced from Streptomyces sp. KIB-H714. Their structures were authenticated by comprehensive spectroscopic data interpretation. Different from all the reported Z-type actinomycins, the ß-ring of the new compound actinomycin Z6 includes an additional ring linked between the actinoyl chromophore and ß-peptidolactone. In Z3 and Z5, the L-threonine in ß-depsipeptide is replaced by the unusual 4-chlorothreonine, an amino acid rarely found in actinomycin family. All isolates were evaluated for cytotoxicity against five human tumor cell lines and for inhibitory activity against Candida albicans and Staphylococcus aureus.


Assuntos
Anti-Infecciosos/farmacologia , Antineoplásicos/farmacologia , Dactinomicina/análogos & derivados , Dactinomicina/farmacologia , Streptomyces/química , Anti-Infecciosos/química , Antineoplásicos/química , Candida albicans/efeitos dos fármacos , Linhagem Celular Tumoral , Dactinomicina/química , Avaliação Pré-Clínica de Medicamentos/métodos , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Oxigênio/química , Espectrometria de Massas por Ionização por Electrospray , Staphylococcus aureus/efeitos dos fármacos , Relação Estrutura-Atividade , Treonina/análogos & derivados , Treonina/química
8.
Zhongguo Zhong Yao Za Zhi ; 43(18): 3683-3687, 2018 Sep.
Artigo em Chinês | MEDLINE | ID: mdl-30384533

RESUMO

A new naphthalene derivative and three known compounds were isolated from the petroleum ether extract of the bulbs of Eleutherine americana by using various chromatographic techniques, such as column chromatography over silica gel and semi-preparative HPLC. Their structures were elucidated by spectroscopic date (MS, UV, IR, NMR), which were identified as eleutherol B (1), 4,8-dihydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid methyl ester (2), 8-hydroxy-3,4-dimethoxy-1-methylanthraquinone-2-carboxylic acid methyl ester (3), and isoeleutherine (4). Compound 1 is a new compound. The diastolic blood vessels activity of compound 1 and 2 were potent, reaching 82.5% and 85.3% at the concentration of 10 µmol·L⁻¹, which were basically the same as that of the positive drug tanshinone ⅡA.


Assuntos
Iridaceae/química , Naftalenos/química , Raízes de Plantas/química , Cromatografia Líquida de Alta Pressão , Estrutura Molecular , Naftalenos/isolamento & purificação , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química
9.
Molecules ; 23(9)2018 Aug 22.
Artigo em Inglês | MEDLINE | ID: mdl-30135380

RESUMO

Five new naphthalene derivatives, named Eleutherols A⁻C (1⁻3) and Eleuthinones B⁻C (4,5), together with three known compounds were isolated from the bulbs of Eleutherine americana. Their structures were elucidated on the basis of spectroscopic analysis including HR-ESI-MS, 1D and 2D NMR techniques. These compounds exhibited a potent effect against the injury of human umbilical vein endothelial cell (HUVECs) induced by high concentrations of glucose in vitro.


Assuntos
Células Endoteliais/efeitos dos fármacos , Naftalenos/química , Naftalenos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Células Endoteliais/metabolismo , Células Endoteliais da Veia Umbilical Humana , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Substâncias Protetoras/farmacologia , Espectrometria de Massas por Ionização por Electrospray
10.
Chem Biodivers ; 15(5): e1700560, 2018 May.
Artigo em Inglês | MEDLINE | ID: mdl-29569369

RESUMO

Three new compounds (1 - 3), including two euphane type triterpenes, 24,24-dimethoxy-25,26,27-trinoreuphan-3ß-ol (1) and (24S)-24-hydroperoxyeupha-8,25-dien-3ß-ol (2), and an ent-atisine diterpene, ent-atisane-3α,16α,17-triol (3), were isolated from an acetone extract of the stems of Euphorbia antiquorum, together with eight known diterpenes (4 - 11). The structures of compounds (1 - 11) were elucidated using NMR and MS spectroscopic methods. Compound 7 showed moderate activity against HIV-1 replication in vitro (EC50 = 1.38 µm).


Assuntos
Fármacos Anti-HIV/farmacologia , Euphorbia/química , HIV-1/efeitos dos fármacos , Terpenos/farmacologia , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Linhagem Celular Transformada , Transformação Celular Viral/efeitos dos fármacos , Relação Dose-Resposta a Droga , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Relação Estrutura-Atividade , Terpenos/química , Terpenos/isolamento & purificação , Replicação Viral/efeitos dos fármacos
11.
Nat Prod Res ; 32(21): 2571-2576, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-29359583

RESUMO

Onosmanones A (1) and B (2), two novel quinonoid xanthenes with two geranyl groups, have been isolated from the whole plants of Onosma paniculatum. Their structures were elucidated on the basis of one- and two-dimensional NMR techniques.


Assuntos
Boraginaceae/química , Xantenos/química , China , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Xantenos/isolamento & purificação
12.
Phytochemistry ; 145: 40-47, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29080411

RESUMO

Six previously undescribed diterpenoids, named euphorantins S-T and euphorneroids A-D, including ingol and ent-atisane types, along with eleven known diterpenoids, were isolated from Euphorbia neriifolia. Their structures were elucidated on the basis of extensive NMR analysis and high resolution mass spectrometry. Euphorneroid D and ent-3-oxoatisan-16α,17-acetonide exhibited moderate anti-HIV-1 activities, with EC50 values of 34 µM (SI = 2.3) and 24 µM (SI = 1.9), respectively.


Assuntos
Fármacos Anti-HIV/farmacologia , Diterpenos/farmacologia , Euphorbia/química , HIV-1/efeitos dos fármacos , Casca de Planta/química , Caules de Planta/química , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Linhagem Celular , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Relação Estrutura-Atividade
13.
Chem Biodivers ; 14(12)2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-29139211

RESUMO

Twenty-eight protostane triterpenoids, including a new degraded one (1), nine new ones (2 - 10), and two new natural ones (11 and 12), have been isolated from the dried rhizomes of Alisma orientale. Alisol R (1) was the first 20,21,22,23,24,25,26,27-octanorprotostane triterpenoid. The absolute configurations of 25-methoxyalisol F (2) and 16ß-hydroperoxyalisol B 23-acetate (3) were determined by X-ray diffraction analysis. In addition, alismaketone-B 23-acetate (28) showed potent vasorelaxant activity on endothelium-intact thoracic aorta rings precontracted with KCl.


Assuntos
Alisma/química , Terpenos/química , 11-beta-Hidroxiesteroide Desidrogenases/antagonistas & inibidores , 11-beta-Hidroxiesteroide Desidrogenases/metabolismo , Alisma/metabolismo , Animais , Aorta/efeitos dos fármacos , Aorta/metabolismo , Humanos , Espectroscopia de Ressonância Magnética , Camundongos , Conformação Molecular , Extratos Vegetais/química , Cloreto de Potássio/toxicidade , Ratos , Rizoma/química , Rizoma/metabolismo , Terpenos/metabolismo , Terpenos/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Vasodilatadores/química , Vasodilatadores/isolamento & purificação , Vasodilatadores/farmacologia , Difração de Raios X
14.
Planta Med ; 83(17): 1368-1373, 2017 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-28662527

RESUMO

Three new compounds (1 - 3), including a sesterterpenoid, aspterpenacid C (1), with an unusual 5/3/7/6/5 pentacyclic skeleton, together with seven known ones (4 - 10), were isolated from the ethanol extract of the traditional Chinese medicinal plant Swertia bimaculata. Their structures were elucidated on the basis of the methods of spectroscopic NMR, MS, and computational chemistry. The structure of 1 was further confirmed by single-crystal X-ray diffraction analysis. Compounds 1 - 10 were tested for activities on the inhibition of nitric oxide production and HIV-1 replication in vitro. Compound 1 exhibited moderate activity in inhibiting nitric oxide production (IC50 = 16.1 µM) and HIV-1 replication (EC50 = 1.35 µM).


Assuntos
Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Medicamentos de Ervas Chinesas/farmacologia , HIV-1/efeitos dos fármacos , Swertia/química , Animais , Fármacos Anti-HIV/química , Anti-Inflamatórios/química , China , Medicamentos de Ervas Chinesas/química , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Células RAW 264.7 , Replicação Viral/efeitos dos fármacos
15.
J Agric Food Chem ; 65(22): 4456-4463, 2017 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-28494582

RESUMO

Six new highly oxygenated grayanane diterpenoids, neopierisoids G-L, 1-6, together with 10 known related compounds, 7-16, were identified from the flowers of the poisonous plant Pieris japonica. The structures were elucidated on the basis of comprehensive NMR spectroscopy and mass analysis. The relative configurations of 1-6 were elucidated by analysis of ROESY spectra and comparison of NMR data with the analogues. The absolute configurations of 1-6 were established by the X-ray diffraction analysis of 1 and comparison of the CD spectra of 1-6. Compared with the skeleton of the normal grayanane diterpenoids, compounds 1-6 shared an unusual seco A ring moiety. The antifeedant activities of compounds 1-16 against Pieris brassicae were evaluated by using a dual-choice bioassay, and compounds 1-10 with a normal grayanane skeleton showed potent antifeedant activity against P. brassicae. The structure-activity relationships of antifeedant activities of 1-16 against P. brassicae are discussed.


Assuntos
Borboletas/efeitos dos fármacos , Diterpenos/química , Diterpenos/farmacologia , Ericaceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Borboletas/fisiologia , Comportamento Alimentar/efeitos dos fármacos , Flores/química , Estrutura Molecular , Relação Estrutura-Atividade
16.
Chem Pharm Bull (Tokyo) ; 65(4): 403-407, 2017.
Artigo em Inglês | MEDLINE | ID: mdl-28381681

RESUMO

Twelve guaiane-type sesquiterpenoids, including four new ones, 10-O-methyl-orientalol A (1), 10-O-ethyl-alismoxide (2), 3ß,4ß-expoxy-chrysothol (3), orientalol G (4), and a new norsesquiterpenoid, orientalol H (5), were isolated from Chinese Alismatis Rhizoma, the dried rhizome of Alisma orientale. The structures of new compounds were elucidated on the basis of spectroscopic data. Moreover, the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells of all compounds was tested.


Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Rizoma/química , Sesquiterpenos de Guaiano/farmacologia , Sesquiterpenos/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Conformação Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/metabolismo , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/isolamento & purificação
18.
Fitoterapia ; 116: 93-98, 2017 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-27894905

RESUMO

Seven pairs of new alkaloid enantiomers, ganocochlearines C-I (1, 3-8), and three pairs of known alkaloids were isolated from the fruiting bodies of Ganoderma cochlear. The chemical structures of new compounds were elucidated on the basis of 1D and 2D NMR data. The absolute configurations of compounds 1, 3-10 were assigned by ECD calculations. Biological activities of these isolates against renal fibrosis were accessed in rat normal or diseased renal interstitial fibroblast cells. Importantly, the plausible biosynthetic pathway for this class of alkaloids was originally proposed.


Assuntos
Alcaloides/farmacologia , Fibroblastos/efeitos dos fármacos , Ganoderma/química , Rim/patologia , Alcaloides/química , Alcaloides/isolamento & purificação , Animais , Linhagem Celular , Fibrose , Carpóforos/química , Rim/citologia , Estrutura Molecular , Ratos , Estereoisomerismo
19.
Planta Med ; 83(7): 631-635, 2017 May.
Artigo em Inglês | MEDLINE | ID: mdl-27852095

RESUMO

Four new naphthoquinones (1-4), including a dimeric one, shikometabolin G (1), together with six known ones (6-10), were isolated from the methanol extract of Onosma paniculatum. Their structures were established based on the analysis of NMR and MS spectroscopic data. All of the compounds were evaluated for inhibitory effects on NO production in murine macrophage RAW 264.7 cells. Compounds 2, 3, 5, 6, 7, 8, and 10 displayed good activity on the inhibition of NO production (IC50 = 0.4-16.5 µM), suggesting the potential property of anti-inflammation.


Assuntos
Anti-Inflamatórios não Esteroides/isolamento & purificação , Boraginaceae/química , Medicamentos de Ervas Chinesas/uso terapêutico , Naftoquinonas/isolamento & purificação , Animais , Anti-Inflamatórios não Esteroides/farmacologia , Camundongos , Naftoquinonas/farmacologia , Óxido Nítrico/biossíntese , Raízes de Plantas/química , Células RAW 264.7
20.
Nat Prod Bioprospect ; 6(6): 291-296, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-27873184

RESUMO

(±)-Evodiakine (1a and 1b), a pair of rearranged rutaecarpine-type alkaloids with an unprecedented 6/5/5/7/6 ring system, were isolated from the nearly ripe fruits of Evodia rutaecarpa. Separation of the enantiomers have been achieved by chiral HPLC column. The structures of (±)-evodiakine were unambiguously elucidated by 1D and 2D NMR spectra, mass spectrometry, and single-crystal X-ray diffraction. Their absolute configurations were determined by comparison of experimental and calculated electronic circular dichroism spectra. A hypothetical biogenetic pathway for (±)-evodiakine was also proposed. Compounds 1a, 1b, and the racemate (1) were tested for their cytotoxic and anti-inflammatory activities.

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