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1.
Zhongguo Zhong Yao Za Zhi ; 49(2): 412-419, 2024 Jan.
Artigo em Chinês | MEDLINE | ID: mdl-38403317

RESUMO

Thirteen compounds were isolated and identified from 70% ethanol extract of the roots of Gentiana macrophylla by multi-chromatographic methods, including microporous resin, silica gel, and C_(18) reversed-phase column chromatography, as well as HPLC as follows: macrophylloside G(1), macrophylloside D(2), 5-formyl-2,3-dihydroisocoumarin(3),(+)-medicarpin(4),(+)-syringaresinol(5), liquiritigenin(6),(3R)-sativanone(7),(3R)-3'-O-methylviolanone(8), 4,2',4'-trihydroxychalcone(9), latifolin(10), gentioxepine(11), 6α-hydroxycyclonerolidol(12), and ethyl linoleate(13). Compound 1 was a new benzopyran glycoside. Compounds 4, 6-10, 12, and 13 were isolated for the first time from Gentiana plants. Compounds 1 and 2 showed promising hepatoprotective activity against D-GalN-induced AML12 cell damage at the concentration of 10 µmol·L~(-1), and compound 2 exhibited more significant activity than silybin at the same concentration.


Assuntos
Glicosídeos Cardíacos , Éteres , Gentiana , Gentiana/química , Glicosídeos/farmacologia , Benzopiranos , Glucosídeos
2.
Phytochemistry ; 217: 113920, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-37951561

RESUMO

Ten lignans, including six previously undescribed phenolic ester glycosyl lignans (1-6), were isolated from a well-known traditional Chinese medicine, Qin-Jiao, which is the dry root of Gentiana macrophylla Pall. (Gentianaceae). Their structures were determined by spectroscopic and chemical methods, especially 2D NMR techniques. Quantum chemical calculations of theoretical ECD spectra allowed the determination of their absolute configurations. Refer to its traditional applications for the treatment of rheumatic arthralgia and hepatopathy, these compounds were evaluated on a TNF-α induced MH7A human synoviocyte inflammation model and a D-GalN induced AML12 hepatocyte injury model. Compounds 1, 2, 5, and 6 significantly reduced the release of proinflammatory cytokine IL-1ß in MH7A cells at 15 µM and they also could strongly protect AML12 cells against D-GalN injury at 30 µM. Flow cytometry and Western blot analysis showed that compound 5 ameliorated D-GalN induced AML12 cell apoptosis by upregulating the expression of anti-apoptotic Bcl-2 protein and down-regulating the expression of pro-apoptotic Bax protein.


Assuntos
Medicamentos de Ervas Chinesas , Gentiana , Lignanas , Humanos , Gentiana/química , Lignanas/farmacologia , Glucosídeos/farmacologia , Glucosídeos/química , Medicamentos de Ervas Chinesas/farmacologia , Inflamação
3.
Molecules ; 28(18)2023 Sep 14.
Artigo em Inglês | MEDLINE | ID: mdl-37764389

RESUMO

Four previously undescribed terpenoid glucosides, including one sesquiterpenoid di-glucoside (1), two new iridoid glucosides (2, 3), and a new triterpenoid tri-glucoside (4), were isolated from a 70% ethanol extract of the root of Gentiana macrophylla (Gentianaceae), along with eight known terpenoids. Their structures were determined by spectroscopic techniques, including 1D, 2D NMR, and HRMS (ESI), as well as chemical methods. The absolute configuration of compound 1 was determined by quantum chemical calculation of its theoretical electronic circular dichroism (ECD) spectrum. The sugar moieties of all the new compounds were confirmed to be D-glucose by GC analysis after acid hydrolysis and acetylation. Anti-pulmonary inflammation activity of the iridoids were evaluated on a TNF-α induced inflammation model in A549 cells. Compound 2 could significantly alleviate the release of proinflammatory cytokines IL-1ß and IL-8 and increase the expression of anti-inflammatory cytokine IL-10.


Assuntos
Gentiana , Pneumonia , Humanos , Terpenos/farmacologia , Fator de Necrose Tumoral alfa , Glucosídeos/farmacologia , Células A549 , Citocinas , Extratos Vegetais/farmacologia
4.
Phytochemistry ; 213: 113780, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37379971

RESUMO

Six previously undescribed N-acetyldopamine (NADA) trimmer racemates, percicamides A-F (1-6), were isolated from a 70% ethanol extract of Cicadae Periostracum. Subsequent chiral-phase separation afforded six pairs of enantiomers, (+)- and (-)-percicamides A-F (1a/1b-6a/6b). Their structures including absolute configurations were elucidated by combined extensive spectroscopic data and quantum chemical calculations. Compounds 1-6 represent the first examples of NADA trimmers with a cis-relationship of H-7'/H-8' or H-7''/H-8''. Bioassays verified that all isolated compounds showed weak inhibitory effects on nitric oxide production in RAW 264.7 cells.


Assuntos
Medicamentos de Ervas Chinesas , 1-(5-Isoquinolinasulfonil)-2-Metilpiperazina , Medicamentos de Ervas Chinesas/química , Óxido Nítrico , Dopamina/farmacologia , Estrutura Molecular
5.
Fitoterapia ; 158: 105144, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35149120

RESUMO

Five new α-pyrones, cryptowratones A-E (1-5), and five known congeners (6-10), together with four other known compounds 11-14 were isolated from the twigs of Cryptocarya wrayi. The structures of the new compounds were elucidated on the basis of extensive spectroscopic data analysis and ECD calculations. All α-pyrones except 6 were evaluated for their stimulatory effects on glucose uptake in vitro with CHO-K1/GLUT4 cells. The positive control insulin displayed an approximate 42 ± 0.14% promotion on glucose uptake at 25 µM, compared with the CHO-K1/GLUT4 group. Compounds 1a/2a, 2, 3, and 10 showed a more significant stimulation of glucose uptake than insulin (25 µM) by 36 ± 0.08%, 27 ± 0.12%, 28 ± 0.12%, and 25 ± 0.12% at 1.5 µM, respectively. Immunofluorescence assays indicated the glucose uptake-stimulatory activity of α-pyrones might be correlated with increased GLUT4 translocation.


Assuntos
Cryptocarya , Cryptocarya/química , Glucose , Estrutura Molecular , Pironas/farmacologia
6.
Fitoterapia ; 156: 105086, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34798164

RESUMO

Two new isoquinoline alkaloids, cryptowrayines A (1) and B (2), along with one known pavine alkaloid (-)-12-hydroxyeschscholtzidine (3), were isolated from the twigs of Cryptocarya wrayi. The structures of new compounds were elucidated by extensive spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Both compounds 1 and 2 exhibited moderate quinone reductase inducing activity in Hepa 1c1c7 cells.


Assuntos
Alcaloides/isolamento & purificação , Cryptocarya/química , Isoquinolinas/isolamento & purificação , Alcaloides/química , Alcaloides/metabolismo , Glucosidases/antagonistas & inibidores , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/metabolismo , Concentração Inibidora 50 , Isoquinolinas/química , Isoquinolinas/metabolismo , Espectroscopia de Ressonância Magnética , Estrutura Molecular , NAD(P)H Desidrogenase (Quinona)/análise , Rotação Ocular
7.
Zhongguo Zhong Yao Za Zhi ; 46(18): 4749-4756, 2021 Sep.
Artigo em Chinês | MEDLINE | ID: mdl-34581085

RESUMO

The 95% ethanol extract of Baphicacanthis Cusiae Rhizoma et Radix was purified by multi-chromatographic methods including microporous resin, silica gel, Sephadex LH-20, and C_(18) reversed-phase column chromatography. Fourteen compounds were isolated and structurally identified, including five phenylethanoid glycosides, five phenylpropanoids, one lupinane triterpene, two alkaloids, and one flavonoid, listed as follows: 2-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol B(1), threo-2,3-bis-(4-hydroxy-3-methoxybenzene)-3-methoxypropanol(2), 2-(3-hydroxy-4-methoxyphenyl)-ethanol-1-O-[3,4-O-di-acetyl-(1→3)-O-α-L-rhamnopyranosyl]-ß-D-glucopyranoside(3), verbascoside(4), 2″,3″-di-O-acetyl martynoside(5),(+)-pinore-sinol(6), diospyrosin(7), daidzein(8), wiedemannioside B(9), buddlenol A(10), 2″-O-acetyl martyonside(11), lupeol(12), indirubin(13), and tryptanthrin(14). Compound 3 was a new phenylethanoid glycoside, and the other 10 compounds were isolated for the first time from Baphicacanthis Cusiae Rhizoma et Radix except compounds 12, 13, and 14.


Assuntos
Glicosídeos Cardíacos , Álcool Feniletílico , Flavonoides , Glicosídeos , Estrutura Molecular , Rizoma
8.
Molecules ; 26(16)2021 Aug 20.
Artigo em Inglês | MEDLINE | ID: mdl-34443633

RESUMO

Pseudostellaria heterophylla is used in China not only as a functional food but also as an herb to tonify the spleen, enhance immunity, and treat palpitation. Our previous investigation showed that a fraction enriched in glycosides obtained from the roots of P. heterophylla possessed pronounced protective effects on H9c2 cells against CoCl2-induced hypoxic injury. However, the active compounds responsible for the observed effects were still unknown. In the current investigation, pseudosterins A-C (1-3), three new alkaloids with a 1-ethyl-3-formyl-ß-carboline skeleton, together with polydatin, have been isolated from the active fraction. Their structures were elucidated on the basis of spectroscopic analysis and quantum chemical calculations. The four compounds showed cardioprotective effects against sodium hydrosulfite-induced hypoxia-reoxygenation injury in H9c2 cells, with the three alkaloids being more potent. This is also the first report of alkaloids with a ß-carboline skeleton isolated from P. heterophylla as cardioprotective agents.


Assuntos
Alcaloides/farmacologia , Carbolinas/farmacologia , Cardiotônicos/farmacologia , Caryophyllaceae/química , Extratos Vegetais/farmacologia , Alcaloides/química , Animais , Carbolinas/química , Cardiotônicos/química , Linhagem Celular , China , Glicosídeos/química , Glicosídeos/farmacologia , Hipóxia/tratamento farmacológico , Extratos Vegetais/química , Raízes de Plantas/química , Ratos
9.
Zhongguo Zhong Yao Za Zhi ; 44(20): 4476-4480, 2019 Oct.
Artigo em Chinês | MEDLINE | ID: mdl-31872635

RESUMO

The 70% ethanol extract of the whole plant of Souliea vaginata was purified by multi-chromatographic methods including macroporous resin,silica gel,Sephadex LH-20,and C18-reversed-phase column chromatography. A new spirocyclic cycloartane triterpenoid was isolated and identified as( 16 R*,20 R*,23 S*,24 R*,25 S*)-16,23: 23,26-diepoxy-15α,24,25-trihydroxy-9,19-cycloart-3ß-O-ß-D-xylopyranoside( 1),and named as soulieoside S. Its planar structure and relative configuration were determined by spectroscopic techniques including 2 D NMR and HRESI-MS. As one of the main components of S. vaginata,compound 1 was evaluated for its anti-inflammatory activity by a lipopolysaccharide( LPS)-stimulated NO production model in RAW264. 7 macrophages,but it didn't show NO production inhibitory effect.


Assuntos
Actaea/metabolismo , Triterpenos/metabolismo , Actaea/química , Glicosídeos , Lipopolissacarídeos , Estrutura Molecular , Triterpenos/análise
10.
Fitoterapia ; 134: 346-354, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30858046

RESUMO

Fourteen acetylbenzofuran derivatives, including three undescribed carbon skeletons with a newly formed hexane or benzene ring on the other side of the benzofuran ring, (±)-eupatonin A (1), (±)-eupatonin B (2), and eupatonin C (3), two new benzofurans (-)-12ß-hydroxygynunone (4) and (+)-12-hydroxyl-13-noreuparin (5), as well as 9 known ones (6-14), were isolated from 95% ethanol extract of the roots of Eupatorium chinense. Their structures were determined by spectroscopic methods and quantum chemical DFT and TDDFT calculations of the NMR chemical shifts and ECD spectra, which helped in the determination of the relative configurations of 1 and 2 and the absolute configurations of 4 and 5, respectively. 1 and 2 were further identified to be racemic mixtures by chiral HPLC analysis. All compounds were evaluated for insulin-stimulated glucose uptake in differentiated C2C12 myotubes. Compounds 1, 3, 4, 5, 11, 12, and 13 markedly enhanced insulin-mediated glucose uptake. (±)-Eupatonin A (1) activated the IRS-1/Akt/GSK-3ß signaling pathway and enhanced insulin stimulated GLUT4 membrane translocation in C2C12 myotubes. On LPS stimulated RAW264.7 macrophages, several compounds exhibited significant inhibitory effect on NO production with IC50 values ranging from 4.94 to 9.70 µΜ. (±)-Eupatonin A (1) again dose-dependently suppressed LPS-induced NO production and decreased the expression of inducible NO synthase (iNOS), through inhibiting NF-κB activity.


Assuntos
Benzofuranos/farmacologia , Eupatorium/química , Macrófagos/efeitos dos fármacos , Fibras Musculares Esqueléticas/efeitos dos fármacos , Animais , China , Proteínas de Ligação a DNA/metabolismo , Glucose/metabolismo , Insulina , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Células RAW 264.7 , Transdução de Sinais/efeitos dos fármacos , Fatores de Transcrição/metabolismo
11.
Molecules ; 24(1)2019 Jan 06.
Artigo em Inglês | MEDLINE | ID: mdl-30621331

RESUMO

Four previously undescribed compounds, including three rarely occurring seco-dammarane triterpenoid glycosides and a pentacyclic triterpenic acid, were isolated from a 70% ethanol extract of the leaves of Cyclocarya paliurus (Juglandaceae), along with eleven known triterpenoids. Their structures were determined by spectroscopic techniques, including 2D NMR and HRESIMS, as well as chemical methods. Among them, several triterpenoids enhanced insulin stimulated glucose uptake in both 3T3-L1 adipocytes and C2C12 myotubes. Furthermore, compound 1 dose-dependently increased glucose uptake through activating AMP-activated protein kinase (AMPK)-p38 pathway. Collectively, triterpenoids from C. paliurus could be developed as insulin sensitizers, which might have therapeutic potential for insulin resistance and hyperglycemia.


Assuntos
Adipócitos/efeitos dos fármacos , Glucose/metabolismo , Juglandaceae/química , Terpenos/farmacologia , Células 3T3-L1 , Quinases Proteína-Quinases Ativadas por AMP , Adipócitos/citologia , Animais , Transporte Biológico , Sobrevivência Celular/efeitos dos fármacos , Descoberta de Drogas , Glicosídeos/química , Insulina , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Folhas de Planta/química , Proteínas Quinases/metabolismo , Transdução de Sinais , Relação Estrutura-Atividade , Terpenos/isolamento & purificação
12.
J Nat Med ; 72(4): 882-889, 2018 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-29752578

RESUMO

Podolactones are a class of structural diverse diterpenoid lactones, mainly isolated from the Podocarpus species. Several bioactivities have been disclosed for podolactones, including cytotoxicity and anti-atherosclerosis. In this study, the seeds of P. nagi were isolated by comprehensive chromatographic methods to obtain three new podolatones, named nagilactone B 1-O-ß-D-glucoside (1), nagilactone N3 3-O-ß-D-glucoside (2), and 2-epinagilactone B (3), as well as a known compound, nagilactone B (4). Their structures were determined by analyses of NMR and HRESIMS data. Compounds 1 and 2 significantly inhibited nitric oxide (NO) production on LPS-stimulated RAW264.7 macrophages, with IC50 values of 0.18 ± 0.04 and 0.53 ± 0.03 µM, respectively. Indomethacin (IC50 4.21 ± 0.32 µM) was used as a positive control. Compound 1 suppressed the expression of inducible NO synthase (iNOS) in a concentration-dependent manner, mediating through inhibiting nuclear factor-κB (NF-κB) activity. This is the first report regarding the anti-inflammatory effect of podolactones, which could be potential anti-inflammatory agents.


Assuntos
Anti-Inflamatórios/uso terapêutico , Medicamentos de Ervas Chinesas/química , NF-kappa B/metabolismo , Óxido Nítrico/metabolismo , Sementes/química , Anti-Inflamatórios/farmacologia , Medicamentos de Ervas Chinesas/farmacologia
13.
Fitoterapia ; 121: 141-145, 2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28625730

RESUMO

Thirty four terpenoids, including two new cadinane-type sesquiterpenoids containing conjugated aromatic-ketone moieties, curcujinone A (1) and curcujinone B (2), were isolated from 95% ethanol extract of the root tubers of Curcuma wenyujin. Their structures were determined by spectroscopic methods, especially 2D NMR and HRMS techniques. The relative and absolute configurations of 1 and 2 were identified by quantum chemical DFT and TDDFT calculations of the 13C NMR chemical shifts, ECD spectra, and specific optical rotations. All compounds and extracts were evaluated for their anti-diabetic activities with a glucose consumption model on HepG2 Cells. The petroleum fraction CWP (10µg/mL) and compounds curcumenol (4), 7α,11α-epoxy-5ß-hydroxy-9-guaiaen-8-one (5), curdione (17), (1S, 4S, 5S 10S)-germacrone (18), zederone (20), a mixture of curcumanolide A (25) and curcumanolide B (26), gajutsulactone B (27), and wenyujinin C (30) showed promising activities with over 45% increasing of glucose consumption at 10µM.


Assuntos
Curcuma/química , Glucose/metabolismo , Sesquiterpenos/química , Terpenos/química , Células Hep G2 , Humanos , Estrutura Molecular , Tubérculos/química , Sesquiterpenos Policíclicos , Sesquiterpenos de Germacrano
14.
Chemistry ; 22(41): 14648-54, 2016 Oct 04.
Artigo em Inglês | MEDLINE | ID: mdl-27539922

RESUMO

Four polycyclic norditerpenoids, cephalotanins A-D (1-4) representing three unprecedented carbon skeletons with highly rigid ring systems, were isolated from Cephalotaxus sinensis and structurally characterized by a combination of various methods. Compounds 1 and 2 are new skeletal norditerpenoid trilactones, while 3 and 4 are two norditerpenoids featuring different new carbon skeletons. Biosynthetic pathways for 1-4 were proposed by involving diverse and very fascinating chemical events with the coexisting cephalotane troponoids as the precursors. Compound 1 exhibited good NF-κB inhibition with an IC50 value of 4.12±0.61 µΜ.


Assuntos
Carbono/química , Cephalotaxus/química , Diterpenos/isolamento & purificação , Extratos Vegetais/química , Diterpenos/química , Diterpenos/farmacologia , Células HEK293 , Humanos , Simulação de Acoplamento Molecular , Estrutura Molecular , NF-kappa B/antagonistas & inibidores , Folhas de Planta/química , Relação Estrutura-Atividade
15.
J Nat Prod ; 79(7): 1791-7, 2016 07 22.
Artigo em Inglês | MEDLINE | ID: mdl-27310249

RESUMO

A new enantiomeric pair of spirodiketones, (+)- and (-)-denobilone A (1 and 2), three new phenanthrene derivatives (3-5), and three new biphenanthrenes (22-24), along with 11 known phenanthrene derivatives (6-16), five known bibenzyl derivatives (17-21), and four known biphenanthrenes (25-28), were isolated from Dendrobium nobile. The structures of 1-5 and 22-24 were elucidated using comprehensive spectroscopic methods. (+)-Denobilone and (-)-denobilone A (1 and 2) were isolated as a pair of enantiomers by chiral HPLC. The absolute configurations of (+)- and (-)-denobilone A (1 and 2) were determined by comparing their experimental and calculated electronic circular dichroism spectra. The absolute configuration of denobilone B (3) was determined by X-ray crystallographic analysis. The inhibitory activities of all compounds against nine phytopathogenic fungi and three cancer cell lines were evaluated.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Bibenzilas/isolamento & purificação , Bibenzilas/farmacologia , Dendrobium/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Fenantrenos/isolamento & purificação , Fenantrenos/farmacologia , Antineoplásicos Fitogênicos/química , Bibenzilas/química , Dicroísmo Circular , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Fungos/efeitos dos fármacos , Conformação Molecular , Estrutura Molecular , Fenantrenos/química , Caules de Planta/química
16.
Org Lett ; 18(12): 2894-7, 2016 06 17.
Artigo em Inglês | MEDLINE | ID: mdl-27228486

RESUMO

Three new ring B-seco limonoids, ciliatonoids A-C (1-3), were isolated from Toona ciliate and structurally characterized by spectroscopic data, X-ray crystallography, and electronic circular dichroism analysis. Ciliatonoids A and B feature an unprecedented limonoid architecture, while ciliatonoid C belongs to a rare class of limonoids. Biological evaluation showed that compound 3 exhibited modest activities against the tested tumor cell lines.


Assuntos
Antineoplásicos Fitogênicos/química , Limoninas/química , Meliaceae/química , Extratos Vegetais/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Dicroísmo Circular , Cristalografia por Raios X , Humanos , Limoninas/isolamento & purificação , Limoninas/farmacologia , Espectroscopia de Ressonância Magnética/métodos , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia
17.
J Nat Prod ; 79(5): 1365-72, 2016 05 27.
Artigo em Inglês | MEDLINE | ID: mdl-27142786

RESUMO

Nine new conjugates of sesquiterpenoids and acylphloroglucinols, named eucarobustols A-I (1-9), as well as 11 known analogues were isolated from the leaves of Eucalyptus robusta. The sesquiterpenoid motifs furnishing the new conjugates included four structural types of aristolane (1 and 2), guaiane (3), eudesmane (4), and aromadendrane (5-9) moieties. Compounds 1 and 2 were found to represent the first examples of conjugates of aristolane and acylphloroglucinol units. In turn, compound 3 features a new coupling model of guaiane and acylphloroglucinol via the C-4-C-7' bond. Compounds 1, 7, and 9 showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 1.3, 1.8, and 1.6 µM, respectively.


Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Eucalyptus/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos de Guaiano/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Sesquiterpenos , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/farmacologia
18.
Org Biomol Chem ; 14(3): 957-62, 2016 Jan 21.
Artigo em Inglês | MEDLINE | ID: mdl-26615760

RESUMO

Chemical investigation into the minor constituents of Aphanamixis grandifolia yielded three new diterpenoid dimers, aphadilactones E-G (1-3) featuring a new carbon skeleton. Their structures and absolute configurations were fully established by comprehensive spectroscopic data analysis and ECD calculation. Discovery of another two new dimers (4 and 5) suggested the structure of recently reported aphanamene A to be re-investigated. Compounds 1-5 showed moderate antimalarial activities with low micromolar IC50 values.


Assuntos
Antimaláricos/farmacologia , Diterpenos/farmacologia , Meliaceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Plasmodium falciparum/efeitos dos fármacos , Antimaláricos/química , Antimaláricos/isolamento & purificação , Dimerização , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Concentração Inibidora 50 , Conformação Molecular , Testes de Sensibilidade Parasitária , Relação Estrutura-Atividade
19.
Fitoterapia ; 103: 283-8, 2015 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-25937500

RESUMO

Phytochemical study on rhizomes of Beesia calthifolia resulted in the isolation of five new (1-5) and three known (6-8) cycloartane triterpenoids possessing a hemiketal or ketal group at C-24 from the EtOAc fraction of 95% ethanol extract. Their structures were determined by spectroscopic and chemical methods, especially HRMS and 2D NMR techniques. Compounds 3 and 4 showed potential hepatoprotective activities against D-galactosamine induced human hepatic L02 cell damage.


Assuntos
Hepatócitos/efeitos dos fármacos , Ranunculaceae/química , Triterpenos/química , Linhagem Celular , Galactosamina/efeitos adversos , Humanos , Estrutura Molecular , Rizoma/química
20.
J Nat Prod ; 78(4): 939-43, 2015 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-25760525

RESUMO

Four new 9',10'-dihydro-biphenanthrenes, including an unprecedented 1,2'-linked biphenanthrene, 4,7,3',5'-tetramethoxy-9',10'-dihydro(1,2'-biphenanthrene)-2,7'-diol (1), a new 1,3'-linked biphenanthrene, 4,7,7'-trimethoxy-9',10'-dihydro(1,3'-biphenanthrene)-2,2',5'-triol (2), and two new 1,1'-linked biphenanthrenes, 4,7,4'-trimethoxy-9',10'-dihydro(1,1'-biphenanthrene)-2,2',7'-triol (3) and 4,7,3',5'-tetramethoxy-9',10'-dihydro(1,1'-biphenanthrene)-2,2',7'-triol (4), as well as two known biphenanthrenes (5, 6), were isolated from a 95% ethanol extract of the fibrous roots of Bletilla striata. Their structures were determined by spectroscopic and spectrometric methods. Atropisomerism of these compounds was considered based on their chiral optical properties and potential energy surface scans at the ab initio HF/3-21G level, which revealed their racemic mixture form. Compounds 2-6 showed potent antibacterial activities against six Gram-positive bacterial strains.


Assuntos
Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Orchidaceae/química , Fenantrenos/isolamento & purificação , Fenantrenos/farmacologia , Antibacterianos/química , Medicamentos de Ervas Chinesas/química , Bactérias Gram-Positivas/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Fenantrenos/química , Rizoma/química
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