RESUMO
Twelve monoterpene indole glycoalkaloids, comprising of three new ones, 19-epi-rhynchophylloside A (1), 7-epi-rhynchophylloside A (2), and 7-epi-anthocephalusine A (3), were isolated from the hook-bearing branches of Uncaria rhynchophylla. The structures and absolute configurations of 1-3 were elucidated by analysis of MS, NMR, ECD, and single-crystal X-ray diffraction or TDDFT-ECD calculations. Glycoalkaloids 1 and 3 showed significant immunosuppressive activity against the proliferation of B lymphocyte induced by LPS with broad selective index.
RESUMO
Twelve compounds, comprising of four new ones, 6ß,7α-limondiol (1) and ethyl 19-hydroxyisoobacunoate diosphenol (2), N-benzoyl 3-prenyltyramine (9) and 9-O-methyl integrifoliodiol (12), were isolated from the twigs with leaves of Tetradium trichotomum. The structures were elucidated by analysis of MS, NMR, and single-crystal X-ray diffraction. Compounds 1, 6, 8, 9 and 12 exhibited immunosuppressive activities in vitro against the proliferation of ConA-induced T lymphocytes and LPS-induced B cells.
Assuntos
Folhas de Planta , Folhas de Planta/química , Estrutura Molecular , Imunossupressores/farmacologia , Imunossupressores/química , Imunossupressores/isolamento & purificação , Linfócitos T/efeitos dos fármacos , Animais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Cristalografia por Raios XRESUMO
A pair of new enantiomeric indolopyridoquinazoline-type alkaloids, (+)-1,7S,8R- and (-)-1,7R,8S-trihydroxyrutaecarpine (3a and 3b), and a new limonoid-tyrosamine hybrid, austrosinin (8), along with six known alkaloids and limonoids, were isolated from the stems with leaves of Tetradium austrosinense. Their structures were elucidated on the basis of analysis of MS, NMR, ECD and time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations, as well as proposed biosynthetic pathway. An anti-inflammatory bioassay in vitro showed 8 had significant immunosuppressive effect against the production of pro-inflammatory cytokine TNF-α in lipopolysaccharide (LPS)-stimulated RAW264.7 cells.
Assuntos
Alcaloides , Limoninas , Rutaceae , Limoninas/farmacologia , Limoninas/química , Estrutura Molecular , Alcaloides/farmacologia , Alcaloides/química , Rutaceae/química , Dicroísmo CircularRESUMO
Fraxinifolines A-F (1-6), six new B-seco limonoids, together with four known A,D-di-seco ones, were isolated from the twigs with leaves of Tetradium fraxinifolium. Their structures with absolute configurations were elucidated on the basis of analysis of MS, NMR, single-crystal X-ray diffraction and biogenetic pathway. An anti-inflammatory bioassay in vitro showed limonoids 1-3 had significant immunosuppressive effect against the production of pro-inflammatory cytokines (IL-1ß and/or TNF-α) in lipopolysaccharide (LPS)-stimulated RAW264.7 cells.
Assuntos
Limoninas , Estrutura Molecular , Limoninas/farmacologia , Limoninas/química , Anti-Inflamatórios/farmacologia , Citocinas , Fator de Necrose Tumoral alfa/metabolismoRESUMO
Hyperacmotone A, a polycyclic polyprenylated acylphloroglucinol (PPAP) with an unprecedented skeleton, along with five undescribed congeners and eleven reported ones, was isolated from Hypericum acmosepalum. Hyperacmotone A possesses a unique monocyclic ring skeleton based on a cyclopent-4-ene-1,3-dione acylphloroglucinol core. Their structures were elucidated by extensive analysis of HRESIMS, NMR, biogenetic pathway, and quantum-chemical calculations. In addition, hypercohone G exhibited significant protective effects on high-glucose-injured HUVECs.
Assuntos
Hypericum , Humanos , Células Endoteliais , GlucoseRESUMO
Melodicochinines A - D (1-4), four new monoterpene indole alkaloids (MIAs), along with 21 known ones, were isolated from the stems and twigs of Melodinus cochinchinensis. Their structures were elucidated on the basis of extensive spectroscopic analysis. A ubiquitin-rhodamine 110 assay showed that 11-methyloxytabersonine had potential inhibitory effect against ubiquitin-specific protease 7 (USP7).
Assuntos
Apocynaceae/química , Extratos Vegetais/química , Alcaloides de Triptamina e Secologanina/isolamento & purificação , China , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Rotação Ocular , Extratos Vegetais/isolamento & purificação , Caules de Planta/química , Alcaloides de Triptamina e Secologanina/química , Espectrofotometria InfravermelhoRESUMO
Acmoxanthones A-E (1-5), five new lavandulylated xanthones, were isolated from the aerial parts of Hypericum acmosepalum, together with four known xanthones. Their structures with absolute configurations were elucidated on the basis of analysis of MS, NMR and chiroptical properties. A bioassay against high glucose-induced damage on human umbilical vein endothelial cells (HUVECs) showed ananixanthone (6) and osajaxanthone (7) had potential antioxidative damage activity with EC50 values of 10.5 µg/mL and 7.6 µg/mL, respectively, while 3-hydroxy-2,4-dimethoxyxanthone (8) exhibited cytotoxic effect on the damaged cells with IC50 values of 7.1 µg/mL.
Assuntos
Hypericum/química , Xantonas/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Células Endoteliais da Veia Umbilical Humana/efeitos dos fármacos , Humanos , Isoflavonas , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Xantonas/isolamento & purificaçãoRESUMO
Uralins A - D, four undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) featuring an unprecedented fused hexacyclic architecture, a unique monocyclic tetra-seco-tetranor-b-PPAP, an oxidative b-PPAP and a rare norspiroindane-type m-PPAP, respectively, were isolated from the aerial parts of Hypericum uralum, along with ten known PPAPs. Their structures and absolute configurations were elucidated by extensive spectroscopic techniques (MS, NMR, [α]D, CD), conceivable biogenetic pathways and time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations. Biological assays showed three b-PPAPs had moderate antioxidative damage activities, while spiroindanes exhibited moderate cytotoxic effects.
Assuntos
Hypericum , Dicroísmo Circular , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Floroglucinol/farmacologiaRESUMO
Twenty-one polycyclic polyprenylated acylphloroglucinols, including three new compounds named as hyperichoisins A (3), B (14) and C (21), were isolated from the aerial parts of Hypericum choisianum. The structures of those new compounds were elucidated by analysis of mass, NMR data, and chiroptical properties. A bioassay showed that otogirinin B had significant inhibitory effect on cell proliferation of A549.
Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Hypericum/química , Células A549 , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Floroglucinol/químicaRESUMO
Hookerianones A - E (1-5), five new polyprenylated acylphloroglucinols (PPAPs), along with six known ones, were isolated from the aerial parts of Hypericum hookerianum. Their structures were elucidated by analyses of MS, NMR, chiroptical properties, biogenetic pathway, and/or single crystal X-ray diffraction. A ubiquitin-rhodamine 110 assay showed that furohyperforin and hypercalin C, two representative PPAPs in this plant, inhibited more than 90% USP7 at the concentration of 10 µM.
Assuntos
Hypericum/química , Floroglucinol/farmacologia , Inibidores de Proteases/farmacologia , Peptidase 7 Específica de Ubiquitina/antagonistas & inibidores , China , Estrutura Molecular , Floroglucinol/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Inibidores de Proteases/isolamento & purificaçãoRESUMO
Alopecines A-E (1-5), five unusual matrine-type alkaloids featuring with an additional dichlorocyclopropane (1-3) or a di/tri-chloromethyl (4/5) attached on the D ring, were isolated from the seeds of Sophora alopecuroides. Their structures and absolute configurations were elucidated by extensive spectroscopic techniques, and X-ray diffraction analyses or time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations. Alkaloid 4 exhibited potent inhibitory effects on the proliferation of ConA-induced T lymphocytes or LPS-induced B cells with IC50 value of 3.98 or 3.74 µM, respectively.
Assuntos
Alcaloides/farmacologia , Imunossupressores/farmacologia , Extratos Vegetais/farmacologia , Sophora/química , Alcaloides/química , Alcaloides/isolamento & purificação , Animais , Linfócitos B/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Concanavalina A/antagonistas & inibidores , Concanavalina A/farmacologia , Relação Dose-Resposta a Droga , Feminino , Imunossupressores/química , Imunossupressores/isolamento & purificação , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Camundongos Endogâmicos BALB C , Conformação Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Sementes/química , Estereoisomerismo , Relação Estrutura-Atividade , Linfócitos T/efeitos dos fármacosRESUMO
A new 12-membered macrolide, aspergillolide (1), along with nine known compounds (2-10), were isolated from the fungus Aspergillus sp. S-3-75 associated with the sea cucumber Holothuria nobilis Selenka. The structure and absolute stereochemistry of 1 were elucidated on the basis of extensive spectroscopic methods and single crystal X-ray diffraction analysis.
Assuntos
Aspergillus/química , Macrolídeos/isolamento & purificação , Pepinos-do-Mar/microbiologia , Animais , Antibacterianos/química , Cristalografia por Raios X , Fungos/química , Holothuria/microbiologia , Macrolídeos/química , Estrutura Molecular , EstereoisomerismoRESUMO
The accumulation of aggregated amyloid-ß (Aß) in the brain is the first critical step in the pathogenesis of Alzheimer's disease (AD), which also includes synaptic impairment, neuroinflammation, neuronal loss, and eventual cognitive defects. Emerging evidence suggests that impairment of Aß phagocytosis and clearance is a common phenotype in late-onset AD. Rutin (quercetin-3-rutinoside) has long been investigated as a natural flavonoid with different biological functions in some pathological circumstances. Sodium rutin (NaR), could promote Aß clearance by increasing microglial by increasing the expression levels of phagocytosis-related receptors in microglia. Moreover, NaR promotes a metabolic switch from anaerobic glycolysis to mitochondrial OXPHOS (oxidative phosphorylation), which could provide microglia with sufficient energy (ATP) for Aß clearance. Thus, NaR administration could attenuate neuroinflammation and enhance mitochondrial OXPHOS and microglia-mediated Aß clearance, ameliorating synaptic plasticity impairment and eventually reversing spatial learning and memory deficits. Our findings suggest that NaR is a potential therapeutic agent for AD.
Assuntos
Doença de Alzheimer/metabolismo , Doença de Alzheimer/patologia , Peptídeos beta-Amiloides/metabolismo , Microglia/efeitos dos fármacos , Microglia/metabolismo , Agregação Patológica de Proteínas/metabolismo , Rutina/farmacologia , Doença de Alzheimer/tratamento farmacológico , Animais , Modelos Animais de Doenças , Imuno-Histoquímica , Camundongos , Camundongos Transgênicos , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Estrutura Molecular , Fagocitose/efeitos dos fármacos , Agregação Patológica de Proteínas/tratamento farmacológico , Rutina/química , Sódio/química , SolubilidadeRESUMO
Seventeen structurally diverse lignans, comprising six new compounds, ecdysanols A (1), B (11), C - E (13-15), and F (17), were isolated from the caulis of Urceola rosea. The structures and absolute configurations of these new compounds were elucidated by means of extensive analysis of mass and NMR data, as well as chiroptical properties. A bioassay in vitro showed that all lignans possessed anti-inflammatory effects by inhibiting the production of TNF-α, NO and/or IL-6 in LPS-stimulated RAW264.7 cells. Ecdysanol F (17) showed the most strongly effect against NO and IL-6 levels.
Assuntos
Anti-Inflamatórios/farmacologia , Apocynaceae/química , Lignanas/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Sobrevivência Celular , China , Feminino , Interleucina-6/metabolismo , Lignanas/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7 , Fator de Necrose Tumoral alfa/metabolismoRESUMO
A phytochemical investigation on the twigs and leaves of Flueggea virosa (Euphorbiaceae) led to the isolation of flueggenoids A - E (1-5), five new 13-methyl-ent-podocarpanes, together with eleven known compounds (6-16). Their structures and absolute configurations were elucidated on the basis of extensive MS and NMR data analysis, and/or single-crystal X-ray diffraction, time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculations, and chemical transformation. All isolates were evaluated for anti-HCV activity, the results showed that terpenoids of F. virosa had nonnegligible contribution for the anti-HCV activity.
Assuntos
Malpighiales/química , Terpenos/química , Linhagem Celular Tumoral , China , Hepacivirus , Humanos , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Componentes Aéreos da Planta/química , Terpenos/isolamento & purificaçãoRESUMO
Six triterpenoids (1-6), four megastigmanes (7-10) and five hydroxycinnamic acid derivatives (11-15) were isolated from the aerial part of Anisomeles indica (Lamiaceae). Of these components, compound 1 was identified to be a new triterpenoid with the structure of 2α,3α,19α-trihydroxyurs-12,20(30)-dien-28-oic acid based on extensive analysis of MS, 1D and 2D NMR spectroscopic data, while compounds 2-13 were obtained for the first time from Anisomeles species.
Assuntos
Ácidos Cumáricos/isolamento & purificação , Lamiaceae/química , Norisoprenoides/isolamento & purificação , Triterpenos/isolamento & purificação , Ácidos Cumáricos/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Norisoprenoides/química , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Triterpenos/químicaRESUMO
Perilla frutescens (L.) Britt. (Lamiaceae) is a traditionally medicinal herb in East Asian countries to treat various diseases. In present study, the low-polarity constituents of the aerial parts of P. frutescens were investigated and their anti-inflammatory effect on lipopolysaccharide (LPS)-stimulated RAW264.7 cells were assayed. Three new furanoid monoterpenoids, named as frutescenones A - C (1-3), together with thirteen known compounds (4-16) were isolated and identified on the basis of extensive spectroscopic analysis and a single-crystal X-ray diffraction study. Among these components, 1 is an unusual monoterpenoid with 2,3'-bifuran skeleton, and 3 is a rare perillaketone-adenine hybrid heterodimer, while the revised NMR arrangements of 4 were reported at the first time. Furthermore, monoterpenoid 4 and alkaloid 15 showed remarkably inhibitory effect on the production of inflammatory mediator (NO) and pro-inflammatory cytokines (TNF-α and/or IL-6) in LPS-stimulated RAW264.7 cells.
Assuntos
Anti-Inflamatórios/farmacologia , Monoterpenos/farmacologia , Perilla frutescens/química , Compostos Fitoquímicos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , China , Citocinas/metabolismo , Lipopolissacarídeos , Camundongos , Estrutura Molecular , Monoterpenos/isolamento & purificação , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Componentes Aéreos da Planta/química , Células RAW 264.7RESUMO
INTRODUCTION: Camellia oleifera flowers are rich in flavonoids, but there has been little attention on their application. A simple and reliable method for determining the content of flavonoids in C. oleifera flowers would be very helpful for the utilisation of agriculture resources. OBJECTIVE: To develop an efficient analytical method for the determination of flavonoids in C. oleifera flowers by high-performance liquid chromatography-ultraviolet (HPLC-UV) detection. METHODOLOGY: Preparing an environmentally-friendly and effective solvent - deep eutectic solvents (DESs) - for compound extraction. Then investigating the influential factors of ultrasound-assisted extraction with DESs by the Box-Behnken design combined with response surface methodology. RESULTS: DES-5 synthesised with choline chloride and lactic acid (1:2) acquired excellent extractability for four flavonoids (quercetin 3-O-rhamnoside, kaempferol 3-O-rhamnoside and their aglycones) with different polarity. The proposed method, which could simultaneously determine four flavonoids with HPLC-UV detection for the first time, displays satisfactory recovery yields and high precision with inter-day relative standard deviation lower than 5.80%. CONCLUSION: DESs could be promising solvents for efficiently and selectively extracting bioactive compounds from plant materials, and the analytical method for flavonoids of C. oleifera flowers could provide reference value for its application and be used in other plant resources.
Assuntos
Camellia/química , Cromatografia Líquida de Alta Pressão , Flavonoides/química , Flores/química , Solventes/químicaRESUMO
The fruits of Swietenia macrophylla (skyfruits) are commercially used as healthcare products to improve blood circulation. An investigation of active ingredients of skyfruits led to the isolation of four new limonoids, swietemacrolides A-D (1-4), together with ten known limonoids (5-14) and one proto-limonoid (15). Their structures were elucidated on the basis of MS and NMR data analysis. Swietemacrolide C (3) at the concentration of 10⯵M showed significant protective effect on H2O2-induced apoptosis in human umbilical vascular endothelial cells (HUVECs), while swieteliacate D (5) displayed moderate anti-apoptotic activity.