RESUMO
Four unknown meroterpenoids named as psidials D-G (1-4) together with 5 known compounds (5-9) had been obtained from the leaves of Psidium guajava. Their absolute structures were elucidated by spectral and calculated methods. Psidials DF (1-3) represented unknown carbon skeleton of the 3,5-diformylbenzyl phloroglucinol-coupled sesquiterpenoid. The possible biosynthetic pathway for 1-3 was postulated. In the bioactivity assay, psidial F (3) was found to possess anti-inflammatory and anticoagulant activities.
Assuntos
Psidium , Anti-Inflamatórios/farmacologia , Anticoagulantes/farmacologia , Estrutura Molecular , Extratos Vegetais/análise , Folhas de Planta/química , Psidium/química , EsqueletoRESUMO
In our screening program for new biologically active secondary metabolites, nine new polycyclic polyprenyled acylphloroglucinols, hyperscabins D-L, together with three known compounds, were obtained from the aerial parts of Hypericum scabrum. The chemical structures of 1-9 were characterized by extensive spectroscopic analyses, nuclear magnetic resonance calculation with DP4+ probability analysis, and the electronic circular dichroism spectra were calculated. Compound 1 was an unusual prenylated acylphloroglucinol decorated with a 5-oxaspiro [4,5] deca-1,9-dione skeleton. Compound 2 was a newly identified spirocyclic polyprenylated acylphloroglucinol possessing a rare 5,5-spiroketal segment. Compounds 3, 8, and 10 (10 µM) exhibited pronounced hepatoprotective activity against d-galactosamine-induced WB-F344 cell damage in vitro assays. All test compounds (1, 3, and 7-12) demonstrated potential inhibitory effects at 10 µM against noradrenalinet ([3H]-NE) reuptake in rat brain synaptosome.
Assuntos
Antidepressivos/farmacologia , Hemiterpenos/farmacologia , Hypericum/química , Floroglucinol/análogos & derivados , Floroglucinol/farmacologia , Substâncias Protetoras/farmacologia , Animais , Antidepressivos/síntese química , Antidepressivos/isolamento & purificação , Linhagem Celular , Hemiterpenos/síntese química , Hemiterpenos/isolamento & purificação , Inibidores da Captação de Neurotransmissores/síntese química , Inibidores da Captação de Neurotransmissores/isolamento & purificação , Inibidores da Captação de Neurotransmissores/farmacologia , Norepinefrina/metabolismo , Floroglucinol/isolamento & purificação , Componentes Aéreos da Planta/química , Substâncias Protetoras/síntese química , Substâncias Protetoras/isolamento & purificação , Ratos , Sinaptossomos/efeitos dos fármacos , Sinaptossomos/metabolismoRESUMO
Seven flavonoid dimers, biflavocochins A-G, together with six known compounds were isolated from the red resins of Dracaena cochinchinensis (Chinese dragon's blood). Their structures were elucidated based on extensive spectroscopic analysis. The absolute configurations of 1-7 was assigned by experimental and quantum chemical calculated ECD spectra, and that of 4 was further established by X-ray diffraction analysis using Cu Kα radiation. Compounds 1-3 are novel dimers of homoisoflavonoid and dihydrochalcone with a unique dibenzopyran ring. Compounds 2, 6, 7 exhibited moderate PTP1B inhibitory activities in an enzyme assay. Compound 1 showed neuroprotective effect on serum deficiency-induced cellular damage in PC12 cells.
Assuntos
Dracaena/química , Inibidores Enzimáticos/farmacologia , Flavonoides/farmacologia , Fármacos Neuroprotetores/farmacologia , Extratos Vegetais/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Animais , Cristalografia por Raios X , Dimerização , Inibidores Enzimáticos/química , Flavonoides/química , Humanos , Modelos Moleculares , Fármacos Neuroprotetores/química , Células PC12 , Extratos Vegetais/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , RatosRESUMO
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 , RatosRESUMO
Eight undescribed 9,19-cycloartane type triterpenoid glycosides (cimdalglnoside A-H) and ten known analogues were obtained from the phytochemical research on the roots of Actaea dahurica (syn. Cimicifuga dahurica). All compounds were characterised by spectroscopic experiments, and chemical method. All the compounds isolated were assayed for cytotoxicity to five human cancer cell lines. Cimdalglnoside G showed promising cytotoxicities against Hela, and MCF-7 cell lines with IC50 values at 7.7 and 12.2⯵M.
Assuntos
Actaea/química , Glicosídeos/farmacologia , Raízes de Plantas/química , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , China , Glicosídeos/isolamento & purificação , Células HeLa , Humanos , Células MCF-7 , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Triterpenos/isolamento & purificaçãoRESUMO
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⯵mol/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 & purificaçãoRESUMO
Eight new meroterpenoids with different types of monoterpene units, namely, magmenthanes A-H (1-8), were identified from the bark of Magnolia officinalis var. biloba. Magmenthane A (1) possesses a 1,3-dioxabicyclo [4.3.01,5] nonane skeleton, 1-5 possess five pairs of enantiomers and 6 possesses a 1,1'-diallyl-biphenyl fragment. The structures of 1-8 were elucidated on the basis of 1D and 2D NMR, HRESIMS and electronic circular dichroism (ECD) calculations. Compounds 5 and 8 displayed significant PTP1B inhibitory activities with IC50 values of 4.38 and 3.88⯵M, respectively.
Assuntos
Inibidores Enzimáticos/farmacologia , Magnolia/química , Fármacos Neuroprotetores/farmacologia , Casca de Planta/química , Extratos Vegetais/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Terpenos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Ácido Glutâmico/farmacologia , Humanos , Estrutura Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Relação Estrutura-Atividade , Terpenos/química , Terpenos/isolamento & purificaçãoRESUMO
Three 18(4â3)-abeo-abietanoids, a new natural product and two new compounds, named tripordolides Aâ»C (1â»3), were isolated from the leaves of Tripterygium wilfordii. Their structures were elucidated on the basis of their spectroscopic analysis, and the absolute configuration of compounds was confirmed by CD and X-ray crystallographic analysis using anomalous scattering of Cu Kα radiation. Compounds 1 and 3 showed moderate inhibitory activities against NO production in lipopolysaccharide-induced (LPS) RAW 264.7 macrophages in vitro.
Assuntos
Abietanos/farmacologia , Macrófagos/efeitos dos fármacos , Óxido Nítrico/análise , Extratos Vegetais/farmacologia , Folhas de Planta/química , Tripterygium/química , Animais , Células Cultivadas , Lipopolissacarídeos/farmacologia , Macrófagos/citologia , Macrófagos/metabolismo , Camundongos , Óxido Nítrico/metabolismoRESUMO
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 VegetaisRESUMO
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/farmacologiaRESUMO
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/farmacologiaRESUMO
In view of the significant neuroprotective effect of Clausena lansium, we continued to separate the n-butanol and the water extracts from the stems of C. lansium in order to find the leading compounds with significant activity. Two new phenolic glycosides, Clausenolside A-B (1-2), one new pair of phenolic enantiomers (3a, 3b), and two new monoterpenoids, clausenapene A-B (4-5), together with twelve known analogues (6-17) were isolated from the stems of C. lansium. Compounds 1-17 were obtained from C. lansium for the first time. Compounds 3a, 3b, 4, 16, and 17 showed strong or moderate potential neuroprotective effects on inhibited PC12 cell injury induced by okadaic acid, and compound 9 exhibited strong potential hepatoprotective activities. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, NMR experiments, and electronic circular dichroism (ECD) spectra.
Assuntos
Clausena/química , Medicamentos de Ervas Chinesas/química , Caules de Planta/química , Animais , Sobrevivência Celular/efeitos dos fármacos , Descoberta de Drogas , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Células Hep G2 , Humanos , Hidrólise , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Fármacos Neuroprotetores/isolamento & purificação , Fármacos Neuroprotetores/farmacologia , Células PC12 , Fenóis/isolamento & purificação , Fenóis/farmacologia , Ratos , EstereoisomerismoRESUMO
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 & purificaçãoRESUMO
Two new limonoids, clauemargines M-N (1-2), together with five known compounds (3-7), were isolated from the stems of Clausena emarginata, and compounds 6 and 7 were gained from this plant for the first time. Their structures were established and elucidated on the basis of comprehensive spectroscopic analysis. The absolute configurations of 1-2 were further determined by the octant rule of saturated cyclic ketone. Compounds 1, 2, 4, and 5 showed moderate neuroprotective effects against L-glutamic acid-induced cellular damage in human neuroblastoma SK-N-SH cells at 10 µM.
Assuntos
Clausena/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Limoninas/isolamento & purificação , Caules de Planta/química , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Ácido Glutâmico/farmacologia , Humanos , Limoninas/química , Limoninas/farmacologia , Estrutura Molecular , Neuroblastoma/induzido quimicamente , Fármacos Neuroprotetores/farmacologiaRESUMO
Three new lignanosides (+)-(8S,7'S,8'S)-burselignan-9'-O-ß-d-glucopyrano side (1), (+)-(8R,7'S,8'R)-isolariciresinol-9'-O-ß-d-fucopyranoside (2), (-)-(8S, 7'R,8'R)-methoxyisoariciresinol-9'-O-α-l-rhamnoside (3), along with four known compounds, were isolated from the aerial parts of Lespedeza cuneata (Dum.Cours.) G.Don. The fucopyranoside has not been reported in this genus previously. Their structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses (UV, IR, HR-ESI-MS, 1D and 2D NMR, CD), as well as by comparison with known analogues in the literature. Compounds 2 and 6 showed moderate hepatoprotective activities.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Glicosídeos/isolamento & purificação , Lespedeza/química , Lignanas/isolamento & purificação , Componentes Aéreos da Planta/química , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Glicosídeos/farmacologia , Lignanas/química , Lignanas/farmacologia , Fígado/efeitos dos fármacos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , EstereoisomerismoRESUMO
Ten compounds were isolated from Mylabris phalerata by using preparative HPLC and column chromatography over MCI gel. On the basis of physical-chemical properties, NMR and MS data analysis, the compounds were identified as 5'-[(1 R,2 R,3 S,6R)-1-hydroxymethyl-2-methyl-3,6-epoxycyclohexane-1,2-dicarboximide]- ethyl-2'-methyl-2'-butenoate (1),cantharidin (2), cyclo-(L-Pro-L-Ala) (3), cyclo-(R-Pro-R-Leu) (4), cyclo-(S-Pro-R-Leu) (5), cyclo-(D-Pro-L-Tyr) (6), indole-3-aldehyde (7), 3-indoleacetic acid (8), valerolactam (9), and 4-hydroxyphthalid (10).Compound 1 was a new compound, and compounds 2-10 were obtained from this genus for the first time. Compounds 1-9 were subjected to cytotoxic activity on HCT-116, HepG2, BGC-823, NCI-H1650, A2780 cell lines, and only compound 2 showed inhibitory effect on all cancer cell lines.
Assuntos
Antineoplásicos/química , Besouros/química , Animais , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Humanos , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Four phenylpropanoid glucosides (1-4) and five lignan glycosides (5-9) were isolated from the aerial parts of Lespedeza cuneata, together with three known lignan glycosides (10-12). Their structures were elucidated on the basis of spectroscopic analyses, and the absolute configurations of compounds 5-9 were determined from the CD spectra. In addition, the compounds were tested for their ability to activate the transcription effect on xbp1 promoter. Compounds 4, 5, 7, 9, 10, and 12 could activate the transcription of xbp1 to varying degrees, with EC50 values ranging from 0.18 to 0.64 µM.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Glicosídeos/isolamento & purificação , Lespedeza/química , Lignanas/isolamento & purificação , Fenilpropionatos/isolamento & purificação , Dicroísmo Circular , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Fenilpropionatos/química , Fenilpropionatos/farmacologia , Componentes Aéreos da Planta/químicaRESUMO
Two new carbazole alkaloids, claulansine S (1) and claulansine T (2), and one new amide alkaloid, clauamide A (3), together with four known analogues (4-7) were isolated from the stems of Clausena lansium. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, and NMR experiments (HSQC, HMBC, and NOE experiments). Compounds 4 and 6 showed moderate hepatoprotective activities.
Assuntos
Alcaloides/isolamento & purificação , Amidas/isolamento & purificação , Carbazóis/isolamento & purificação , Clausena/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Amidas/química , Amidas/farmacologia , Carbazóis/química , Carbazóis/farmacologia , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Fígado/efeitos dos fármacos , Fígado/metabolismo , Fígado/patologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Caules de Planta/química , Substâncias Protetoras/farmacologiaRESUMO
Four new norsesquiterpenes wilfordonols A-D (1-4), along with three known compounds, sarmentol B (5), boscialin (6), and (+)-loliolide (7), were isolated from the leaves of Tripterygium wilfordii Hook.f.. The structures of the new compounds were elucidated on the basis of their spectroscopic analysis, and the absolute configuration of the compounds was confirmed by CD and modified Mosher's method. At a concentration of 10 µM, compounds 4, 6, and 7 inhibited signal transducer and activator of transcription 1 translocation by 34.27 ± 1.02%, 48.93 ± 1.76%, and 70.31 ± 2.20%, respectively.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Tripterygium/química , Benzofuranos/química , Benzofuranos/isolamento & purificação , Cicloexanóis/química , Cicloexanóis/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
Seven new carbazole alkaloids, clauemarazoles A-G, together with 19 known analogues were isolated from the stems of Clausena emarginata. Their structures were established on the basis of spectroscopic analyses, and the absolute configurations of compounds 1a, 1b, 5a, and 5b were confirmed by their ECD spectroscopy. Compounds 4, 13, 15, and 17 exhibited inhibitory abilities on LPS-induced NO production. Compounds 10-12, 20, 22, and 24 displayed hepatoprotective effects against DL-galactosamine-induced damage in WB-F344 cells.