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1.
Zhongguo Zhong Yao Za Zhi ; 46(16): 4145-4149, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34467726

RESUMO

With repeated silica gel, octadecyl silica(ODS), and Sephadex LH-20 column chromatography, normal-phase and reverse-phase high performance liquid chromatography(HPLC), etc., a pair of new enantiomers and 5 known compounds were separated from the 95% ethanol extract of Chloranthus multistachys. These compounds were identified by the nuclear magnetic resonance spectroscopy(including 1 D-NMR and 2 D-NMR), single-crystal X-ray diffraction, circular dichroism(CD) spectroscopy, mass spectrometry(MS), and some other methods as(1R,4R,5R,8S,10R)-chloraeudolide H(1 a),(1S,4S,5S,8R,10S)-chloraeudolide H(1 b), hydroxyisogermafurenolide(2), 4α-hydroxy-5α,8ß(H)-eudesm-7(11)-en-8,12-olide(3), chloraniolide A(4), chlorantene D(5), 4α,8ß-dihydroxy-5α(H)-eudesm-7(11)-en-8,12-olide(6). Compounds 1 a and 1 b are a pair of new eudesmane-type sesquiterpene enantiomers, and compounds 2-4 were isolated from C. multistachys for the first time.


Assuntos
Sesquiterpenos , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Estereoisomerismo
2.
Zhongguo Zhong Yao Za Zhi ; 46(15): 3789-3796, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34472251

RESUMO

The genus Chloranthus has 13 species and 5 varieties in China, which can be found in the southwest and northeast regions. Phytochemical studies on Chloranthus plants have reported a large amount of terpenoids, such as diterpenoids, sesquiterpenoids, and sesquiterpenoid dimers. Their anti-inflammation, anti-tumor, antifungal, antivirus, and neuroprotection activities have been confirmed by previous pharmacological research. Herein, research on the chemical constituents from Chloranthus plants and their biological activities over the five years was summarized to provide scientific basis for the further development and utilization of Chloranthus plants.


Assuntos
Diterpenos , Sesquiterpenos , Compostos Fitoquímicos/farmacologia , Plantas , Sesquiterpenos/farmacologia , Terpenos
3.
Fitoterapia ; 153: 104971, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34166705

RESUMO

Seven eudesmane-type sesquiterpenoids, including three pairs of racemic compounds (1a-3a and 1b-3b) and a sesquiterpenoid lactone (4), were obtained from the roots of Chloranthus serratus. The structures of these sesquiterpenoids were characterized based on spectroscopic analyses, ECD calculations, and X-ray diffraction experiment. Neuroprotection assays of the isolated eudesmane-type sesquiterpenoids were conducted on H2O2 damaged PC12 cells. At the concentration of 10 µM, compounds 1b and 4 increased cell viability from 54.8 ± 3.3% to 76.8 ± 2.3 and 72.7 ± 8.2%, respectively.


Assuntos
Magnoliopsida/química , Fármacos Neuroprotetores/farmacologia , Sesquiterpenos de Eudesmano/farmacologia , Animais , China , Estrutura Molecular , Fármacos Neuroprotetores/isolamento & purificação , Células PC12 , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Ratos , Sesquiterpenos de Eudesmano/isolamento & purificação
4.
Zhongguo Zhong Yao Za Zhi ; 46(8): 2067-2071, 2021 Apr.
Artigo em Chinês | MEDLINE | ID: mdl-33982521

RESUMO

Eight sesquiterpenes were isolated and purified from the ethanol extract of Chloranthus henryi by column chromatographies over silica gel, ODS and Sephadex LH-20,and preparative HPLC. Their chemical structures were established by spectral data and physiochemical properties as(1S,6S,8S,10R)-8-ethoxy-10-methoxychlomultin C(1),tianmushanol(2),multistalide A(3),myrrhterpenoid N(4),1α,9α-dihydroxy-8,12-expoxy-eudesma-4,7,11-trien-6-one(5),4ß,10α-aromadendranediol(6),oplopanone(7),10α-hydroxycadinan-4-en-3-one(8). Among them, compound(1) was a new compound, and compounds 2-8 were isolated from Chloranthus henryi for the first time.


Assuntos
Sesquiterpenos , Cromatografia Líquida de Alta Pressão , Estrutura Molecular
5.
Nat Prod Res ; : 1-8, 2021 May 27.
Artigo em Inglês | MEDLINE | ID: mdl-34044699

RESUMO

Phytochemical investigation on the whole plant of Chloranthus multistachys pei (Chloranthaceae) afforded three pairs of new sesquiterpene enantiomers (+)/(-)-chlorantene M [(+)/(-)-1], (+)/(-)-chlorantene M1 [(+)/(-)-2] and (+)/(-)-chlorantene N [(+)/(-)-3]. The structures of new compounds were determined through spectroscopic techniques (HR-ESI-MS, 1 D and 2 D NMR), besides, their absolute and relative configurations were established by using Single-crystal X-ray diffraction analysis and CD spectrum. The anti-inflammatory potential of all compounds was evaluated by applying LPS induced RAW 264.7 macrophage inflammatory model, and the results were that none of these compounds showed activity (IC50 > 100 µM).

6.
Fitoterapia ; 151: 104871, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-33652076

RESUMO

A rare sesquiterpenoid possessing a 6/6 bicyclic system fused with two clustered furan units and a pair of guaiane-type sesquiterpenoids were acquired from the roots of Chloranthus henryi. Their structures with absolute configurations were characterized with spectroscopic data, ECD, and X-ray diffraction analysis. All three sesquiterpenoids showed moderate neuroprotective activities on PC12 cells damaged with hydrogen peroxide.


Assuntos
Magnoliopsida/química , Fármacos Neuroprotetores/farmacologia , Sesquiterpenos/farmacologia , Animais , China , Estrutura Molecular , Fármacos Neuroprotetores/isolamento & purificação , Células PC12 , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Ratos , Sesquiterpenos/isolamento & purificação
7.
Fitoterapia ; 141: 104472, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31917303

RESUMO

Three pairs of new germacranolides, (+)/(-)-chlogermacrones A-C, along with two known analogues were obtained from the roots of Chloranthus henryi. Spectroscopic techniques and single-crystal X-ray crystallographic analyses were used for the structure elucidation of the compounds. All of the isolated compounds were tested for their neuroprotective effects on H2O2 damaged PC12 cells, compounds 3 and 5 increased cell viability from 43.4 ± 1.3% to 99.6 ± 8.7 and 68.1 ± 4.8% at 10 µM, respectively.


Assuntos
Magnoliopsida/química , Fármacos Neuroprotetores/farmacologia , Raízes de Plantas/química , Animais , Sobrevivência Celular/efeitos dos fármacos , Modelos Moleculares , Estrutura Molecular , Fármacos Neuroprotetores/química , Células PC12 , Ratos
8.
Fitoterapia ; 137: 104185, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31150768

RESUMO

Six new and one known dihydroagarofuran sesquiterpenoids esterified with organic acids were obtained from the leaves of Tripterygium wilfordii. Spectroscopic techniques (UV, IR, MS, NMR, ORD and CD) were used for the structure elucidation of the compounds. The structures of compounds 1 and 2 were confirmed by X-ray single crystallographic analyses. The inhibitory effects on NO production in LPS-induced macrophages of 1-7 were conducted. At 10 µmol/L, compounds 1, 2 and 7 showed moderate inhibitory effects on NO production in LPS-induced macrophages with inhibitory rate at 31.2 ±â€¯3.6, 40.9 ±â€¯4.3, and 66.79 ±â€¯3.1%, respectively.


Assuntos
Macrófagos/efeitos dos fármacos , Sesquiterpenos/farmacologia , Tripterygium/química , Animais , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação
9.
Phytochemistry ; 160: 48-55, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30708138

RESUMO

Ten undescribed 9,19-cycloartane type triterpenoid glycosides (cimdahxynoside A-J) and five known analogues were obtained from the phytochemical research on the roots of Actaea dahurica (syn. Cimicifuga dahurica). All compounds were characterised by spectroscopic experiments, chemical method and X-ray Single-crystal diffraction analysis. Cimdahxynoside A represented the first X-ray crystallography of 9,19-cycloartane type triterpenoid diglycoside. The cytotoxicity of all compounds were tested against five human cancer cell lines. Cimdahxynoside F showed significant cytotoxicity, with IC50 values between 6.6 and 9.9 µM.


Assuntos
Actaea/química , Glicosídeos/química , Glicosídeos/farmacologia , Raízes de Plantas/química , Triterpenos/química , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Humanos , Modelos Moleculares , Conformação Molecular
10.
Org Lett ; 20(15): 4549-4553, 2018 08 03.
Artigo em Inglês | MEDLINE | ID: mdl-30020793

RESUMO

Three triterpene saponins, nototronesides A-C (1-3), possessing an unprecedented 6/6/9 fused tricyclic tetranordammarane core, were isolated from the leaves of Panax notoginseng. Their structures were elucidated on the basis of spectroscopic data, and the structure of sapogenin (1a) was further confirmed by X-ray crystallography. The existence of 1-3 adds a new dimension to the diversity of the triterpene family. Moreover, compound 2 showed a moderate neuroprotective effect on serum deficiency-induced cellular damage in PC12 cells.

11.
Org Lett ; 20(12): 3682-3686, 2018 06 15.
Artigo em Inglês | MEDLINE | ID: mdl-29863363

RESUMO

Magterpenoid A (1), possessing a rare 4,6,11-trioxatricyclo[5.3.1.01,5]undecane framework with an irregular monoterpenoid moiety, magterpenoid B (2), with an unprecedented 6/6/6/6 polycyclic skeleton, and magterpenoid C (3), a novel terpenoid quinone with a C6-C3 unit, were isolated from the bark of Magnolia officinalis var. biloba. Plausible biogenetic pathways of 1-3 are presented. Compounds 1 and 3 exhibited significant PTP1B inhibitory activities with IC50 values of 1.44 and 0.81 µM, respectively.


Assuntos
Magnolia , Estrutura Molecular , Casca de Planta , Extratos Vegetais
12.
J Asian Nat Prod Res ; 20(5): 451-459, 2018 May.
Artigo em Inglês | MEDLINE | ID: mdl-29873252

RESUMO

Three new C-methylated phenylpropanoid glycosides (1, 2), a new 8-4'-oxyneolignan (3), together with two known analogs (4, 5), were isolated from the rhizomes of Imperata cylindrical Beauv. var. major (Nees) C. E. Hubb. Their structures were determined by spectroscopic and chemical methods. Compounds 1, 2, and 5 (10 µM) exhibited pronounced hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in vitro assays. Furthermore, their antioxidant activities against Fe2+-cysteine-induced rat liver microsomal lipid peroxidation and the effects on the secretion of TNF-α in murine peritoneal macrophages (RAW264.7) induced by lipopolysaccharides were evaluated.


Assuntos
Glicosídeos/química , Glicosídeos/farmacologia , Poaceae/química , Rizoma/química , Animais , Antioxidantes/química , Antioxidantes/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Células Hep G2 , Humanos , Peroxidação de Lipídeos , Macrófagos/efeitos dos fármacos , Camundongos , Microssomos Hepáticos/efeitos dos fármacos , Células RAW 264.7 , Ratos
13.
Fitoterapia ; 128: 187-191, 2018 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-29778574

RESUMO

Four new nerolidol-type sesquiterpene glucosides, triptergosidols A-D (1-4) were isolated from the leaves of Tripterygium wilfordii. Three aglycones, named triptergerols A (1a), B (2a), and C (3a), were acquired by enzymatic hydrolysis of 1-3. The structures of nerolidol-type sesquiterpenes were elucidated on base of kinds of spectroscopic analysis, and their absolute configurations were determined by CD method. In addition, compounds 1-4 were tested for cytotoxicity against two cell lines and inhibitory effects against NO production in RAW264.7 macrophage.


Assuntos
Glucosídeos/isolamento & purificação , Folhas de Planta/química , Sesquiterpenos/isolamento & purificação , Tripterygium/química , Animais , Linhagem Celular Tumoral , Glucosídeos/farmacologia , Humanos , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Células RAW 264.7 , Sesquiterpenos/farmacologia
14.
J Nat Prod ; 81(2): 270-278, 2018 02 23.
Artigo em Inglês | MEDLINE | ID: mdl-29355322

RESUMO

Thirteen dihydroagarofuran derivatives, including 12 new sesquiterpenoid esters and one known sesquiterpenoid alkaloid, were obtained from the leaves of Tripterygium wilfordii. Spectroscopic techniques and the ECD method were used for the structure elucidation of the compounds. The structures of compounds 1 and 8 were confirmed by single-crystal X-ray crystallographic analyses. Compounds 8, 9, 11, 12, and 13 increased cell viability of the okadaic acid treated PC12 cells from 60.4 ± 23.0% to 72.4 ± 14.1, 71.5 ± 11.5, 75.7 ± 15.6, 81.2 ± 13.1, and 86.2 ± 25.5% at 10 µM, respectively.


Assuntos
Fármacos Neuroprotetores/química , Folhas de Planta/química , Sesquiterpenos/química , Tripterygium/química , Alcaloides/química , Alcaloides/farmacologia , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Fármacos Neuroprotetores/farmacologia , Células PC12 , Ratos , Sesquiterpenos/farmacologia
15.
Phytochemistry ; 145: 10-17, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29035776

RESUMO

Seven dammarane-type saponins previously undescribed (notoginsenosides Fh1-Fh7) were isolated from the aqueous extract leaves of Panax notoginseng (Burk.) F.H.Chen (Araliaceae), together with eleven known saponins. Their structures of were elucidated by spectroscopic analysis (NMR, UV, IR, ect.), HR-ESI-MS techniques and chemical methods. Screening results indicated that compounds 4, 5, 12, 13 showed moderate neuroprotective effects on H2O2-induced cellular damage in human neuroblastoma SH-SY5Y cells (10 µM).


Assuntos
Fármacos Neuroprotetores/farmacologia , Panax notoginseng/química , Folhas de Planta/química , Saponinas/farmacologia , Triterpenos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Humanos , Peróxido de Hidrogênio/antagonistas & inibidores , Peróxido de Hidrogênio/farmacologia , Estrutura Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Saponinas/química , Saponinas/isolamento & purificação , Relação Estrutura-Atividade , Triterpenos/química , Triterpenos/isolamento & purificação
16.
J Asian Nat Prod Res ; 20(4): 337-343, 2018 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-29156976

RESUMO

Two new saponins, notoginsenosides Ng1 (1) and Ng2 (2), together with seven known compounds (3-9), were isolated from the leaves of Panax notoginseng. Their structures were elucidated by UV, IR, HRESIMS, and NMR experiments. Compounds 6 and 7 showed moderate cytotoxic activities against HCT-116, with IC50 values of 4.98 and 0.64 µmol/L, respectively.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Panax notoginseng/química , Saponinas/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Células HCT116 , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Saponinas/química , Saponinas/farmacologia
17.
J Asian Nat Prod Res ; 19(6): 564-571, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-28534444

RESUMO

Further study on the constituents from the stems of Hydrangea paniculata Sieb resulted in isolation of two new compounds 1-2, including 1 monoterpenoid and 1 phenolic glycoside, along with 10 known compounds. Their structures were elucidated on the basis of spectroscopic data, including UV, IR, MS, and NMR experiments, along with chemical methods. At 10 µM, compounds 1 and 2 exhibited comparable activities with bicyclol in vitro assays for hepatoprotective activity against APAP-induced HepG2 cell damage.


Assuntos
Glicosídeos/isolamento & purificação , Hydrangea/química , Monoterpenos/isolamento & purificação , Caules de Planta/química , Compostos de Bifenilo/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Células Hep G2 , Humanos , Fígado/efeitos dos fármacos , Estrutura Molecular , Monoterpenos/química , Monoterpenos/farmacologia , Ressonância Magnética Nuclear Biomolecular
18.
Fitoterapia ; 118: 21-26, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-28163075

RESUMO

Three new lupane-type triterpenoids (1-3), three new oleane-type triterpenoids (4-6), as well as two known compounds (7-8) were isolated from Euonymus carnosus. The structures of the compounds were elucidated on the basis of spectroscopic data analyses, including UV, IR, MS, and NMR experiments. The inhibitory on LPS-induced NO production in microglia BV2 cells of compounds 1-8 were also evaluated. Compounds 1 and 2 showed moderate abilities to inhibit NO production, with IC50 values of 5.99 and 8.47µM, respectively.


Assuntos
Anti-Inflamatórios/química , Microglia/efeitos dos fármacos , Triterpenos Pentacíclicos/química , Caules de Planta/química , Animais , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Triterpenos Pentacíclicos/isolamento & purificação
19.
Zhong Yao Cai ; 38(10): 2087-90, 2015 Oct.
Artigo em Chinês | MEDLINE | ID: mdl-27254920

RESUMO

OBJECTIVE: To study sesquiterpenes from the root of Chloranthus serratus. METHODS: The sesquiterpenes of Chloranthus serratus were isolated and purified by various chromatographic techniques, such as silica gel, Sephadex LH-20 and preparative HPLC. The structures of these isolated compounds were identified by spectroscopic analysis. RESULTS: Ten sesquiterpenes were isolated and identified as follows: 1ß, 8ß-dihydroxy-eudesman-4 (15), 7 (11) -dien-8α, 12-olide (I), curcolonol (II), 4ß, 8ß-dihydroxy-5α (H) -eudesm-7 (11) -en-8, 12-olide (III), 1ß, 8,ß-dihydroxy-eudesman-3, 7 (11) -dien-8α, 12-olide (IV), multistalactone E (V), zedoarofuran (VI), 8ß,9α-dihydroxylindan-4(5), 7(11) -dien-8α,12-olide(VII), serralactone A (VIII), 8-epi-ivangustin (IX), and chloranthalactone E (X ). CONCLUSION: Compounds I, II, IV - VII, IX and X are isolated from Chloranthus serratus for the first time.


Assuntos
Magnoliopsida/química , Compostos Fitoquímicos/análise , Raízes de Plantas/química , Sesquiterpenos/análise , Cromatografia Líquida de Alta Pressão , Compostos Heterocíclicos com 3 Anéis/análise , Compostos Fitoquímicos/isolamento & purificação , Plantas Medicinais/química
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