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1.
Antioxidants (Basel) ; 11(4)2022 Apr 08.
Artigo em Inglês | MEDLINE | ID: mdl-35453420

RESUMO

Liverworts are rich in bibenzyls and related O-glycosides, which show antioxidant activity. However, glycosyltransferases that catalyze the glycosylation of bibenzyls have not yet been characterized. Here, we identified two bibenzyl UDP-glucosyltransferases named MpUGT737B1 and MpUGT741A1 from the model liverwort Marchantia polymorpha. The in vitro enzymatic assay revealed that MpUGT741A1 specifically accepted the bibenzyl lunularin as substrate. MpUGT737B1 could accept bibenzyls, dihydrochalcone and phenylpropanoids as substrates, and could convert phloretin to phloretin-4-O-glucoside and phloridzin, which showed inhibitory activity against tyrosinase and antioxidant activity. The results of sugar donor selectivity showed that MpUGT737B1 and MpUGT741A1 could only accept UDP-glucose as a substrate. The expression levels of these MpUGTs were considerably increased after UV irradiation, which generally caused oxidative damage. This result indicates that MpUGT737B1 and MpUGT741A1 may play a role in plant stress adaption. Subcellular localization indicates that MpUGT737B1 and MpUGT741A1 were expressed in the cytoplasm and nucleus. These enzymes should provide candidate genes for the synthesis of bioactive bibenzyl O-glucosides and the improvement of plant antioxidant capacity.

2.
J Nat Prod ; 84(12): 3020-3028, 2021 12 24.
Artigo em Inglês | MEDLINE | ID: mdl-34797067

RESUMO

Ten new triterpenoids, including nine 9,10-seco-cycloartanes (1-9) and one 9,19-cyclolanostane (10), as well as one sesquiterpenoid (11) and four known compounds (12-15), were extracted and purified from the whole plant of the Chinese liverwort Lepidozia reptans. Multiple techniques (NMR, HRESIMS, IR, and X-ray crystallographic analysis) were applied to determine the structures of the isolated compounds. Bioassay determinations showed that compound 7, which contains an α,ß-unsaturated carbonyl moiety in its structure, inhibited the growth of a panel of cancer cell lines with IC50 values ranging from 4.2 ± 0.2 to 5.7 ± 0.5 µM. Further investigation revealed that compound 7 induces PC-3 cell death via mitochondrial-related apoptosis.


Assuntos
Hepatófitas/química , Triterpenos/farmacologia , Linhagem Celular Tumoral , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Análise Espectral/métodos , Triterpenos/química , Triterpenos/isolamento & purificação
3.
Angew Chem Int Ed Engl ; 60(28): 15286-15290, 2021 07 05.
Artigo em Inglês | MEDLINE | ID: mdl-33876516

RESUMO

An enantioselective synthetic approach for preparing manginoids and guignardones, two types of biogenetically related meroterpenoids, is reported. This bioinspired and divergent synthesis employs an oxidative 1,3-dicarbonyl radical-initiated cyclization and cyclodehydration of the common precursor to forge the central ring of the manginoids and guignardones, respectively, at a late stage. Key synthetic steps include silica-gel-promoted semipinacol rearrangement to form the 6-oxabicyclo[3.2.1]octane skeleton and the Suzuki-Miyaura reaction of vinyl bromide to achieve fragment coupling. This synthesis protocol enables the asymmetric syntheses of four fungal meroterpenoids from commercially available materials.

4.
J Nat Prod ; 84(5): 1459-1468, 2021 05 28.
Artigo em Inglês | MEDLINE | ID: mdl-33913326

RESUMO

An EtOH extract of the Chinese liverwort Radula apiculata showed cytotoxic activity against the A549 lung cancer cell line. Bioassay-guided fractionation led to the isolation of 19 prenylated bibenzyls, including eight previously unknown dimeric prenylated bibenzyls [radulapins A-H (1-8)], four new prenylated bibenzyls (9-12), and seven known compounds (13-19). Compounds 1-11 were analyzed as racemates by chiral-phase separation. Their structures were determined by detailed analysis of their spectroscopic data and by single-crystal X-ray diffraction, chiral resolutions, and electronic circular dichroism measurements. Using an MTT assay, these dimers (1-8) showed significant cytotoxic activity against a panel of human cancer cell lines. Further investigation revealed that compound 4 induces PC-3 cell death via mitochondrial-derived apoptosis.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Bibenzilas/farmacologia , Hepatófitas/química , Células A549 , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Bibenzilas/isolamento & purificação , China , Humanos , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Mitocôndrias/efeitos dos fármacos , Estrutura Molecular , Células PC-3 , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Prenilação , Estereoisomerismo
5.
Angew Chem Int Ed Engl ; 59(45): 19919-19923, 2020 11 02.
Artigo em Inglês | MEDLINE | ID: mdl-32696611

RESUMO

A divergent synthetic approach to biogenetically related diterpenoids such as ent-kauranes, ent-trachylobanes, ent-beyerane, and ent-atisane has been developed. The unified synthetic route involves the De Mayo reaction to rapidly generate the bicyclo[3.2.1]-octane moiety of ent-kaurane. The key reactions also include bioinspired nucleophilic cyclopropanation generating the [3.2.1.02,7 ]-tricyclic core of ent-trachylobane and regioselective cyclopropane fragmentation furnishing ent-beyerane and ent-atisane through the nucleophilic attack and protonation of the cyclopropane ring. This strategy enables the asymmetric total syntheses of six diterpenoids from the commercially available geraniol.

6.
J Nat Prod ; 83(6): 1766-1777, 2020 06 26.
Artigo em Inglês | MEDLINE | ID: mdl-32479076

RESUMO

Fourteen new terpenoids plagicosins A-N (1-14), including seven sesquiterpenoids (1-7) consisting of six ent-bicyclogermacrenes and one ent-2,3-seco-aromadendrane, as well as seven diterpenoids (8-14) comprising five fusicoccanes, a eunicellane, and a rare gersemiane, were isolated from the Chinese liverwort Plagiochila fruticosa Mitt. The structures of these terpenoids were determined on the basis of comprehensive analysis of MS and NMR spectroscopic data coupled with electronic circular dichroism (ECD) and coupling constant calculations. Plagicosin F (6) displayed potent antivirulence activity through inhibiting the hyphal morphogenesis, adhesion, and biofilm formation of Candida albicans. The genes related to hyphal formation were regulated by 6.


Assuntos
Antifúngicos/farmacologia , Candida albicans/efeitos dos fármacos , Hepatófitas/química , Terpenos/farmacologia , Biofilmes/efeitos dos fármacos , Dicroísmo Circular , Diterpenos/química , Hifas/efeitos dos fármacos , Hifas/crescimento & desenvolvimento , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Sesquiterpenos/química , Terpenos/química , Virulência/efeitos dos fármacos
7.
Phytochemistry ; 174: 112341, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32240851

RESUMO

Eight undescribed terpenoids, namely, odongrossins A-H, together with two known terpenoids were isolated from Odontoschisma grosseverrucosum Stephani (Cephaloziaceae). Their structures were established based on NMR data, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction measurements. Odongrossin A and odongrossin G displayed moderate anti-virulence activities against CDR1-and CDR2-efflux-pump-deficient Candida albicans DSY654. Further investigation of odongrossin A revealed that it inhibited adhesion and biofilm formation on C. albicans DSY654. The results regarding the transcription levels of genes demonstrated that odongrossin A could regulate the expression of genes that are associated with the virulence of C. albicans DSY654.


Assuntos
Antifúngicos , Hepatófitas , Biofilmes , Candida albicans , Proteínas Fúngicas , Terpenos , Virulência
8.
Phytochemistry ; 174: 112324, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32163786

RESUMO

In this study, 14 previously undescribed terpenoids were isolated from the Chinese liverwort Heteroscyphus coalitus (Hook.) Schiffner, including a rare harziane type diterpenoid, heteroscyphsic acid A; eight ent-clerodane diterpenoids, heteroscyphsic acids B-I; four labdane diterpenoids, heteroscyphins A-D; and one guaiane sesquiterpene, heteroscyphin E; as well as a known ent-junceic acid. Their structures were determined by a combination of MS, NMR spectroscopy, electronic circular dichroism (ECD) and single crystal X-ray diffraction analyses. The anti-virulence activity of the isolated compounds against Candida albicans DSY654 demonstrated that most of them could block hyphal growth at concentrations ranging from 4-32 µg/ml. Further investigation of the most active compound, heteroscyphin D, revealed that it could suppress the ability of C. albicans DSY654 to adhere to A549 cells and form biofilms, and modulate the transcription of related genes in this fungus.


Assuntos
Diterpenos Clerodânicos , Hepatófitas , Sesquiterpenos , Candida albicans , Terpenos
9.
Biochem Biophys Res Commun ; 518(3): 526-532, 2019 10 20.
Artigo em Inglês | MEDLINE | ID: mdl-31445708

RESUMO

Oxidative stress is one of the main pathogenesis for many human diseases. Nuclear factor erythroid 2-related factor 2 (Nrf2)/antioxidant response element (ARE) signaling pathway plays a key role in regulating intracellular antioxidant responses, and thus activation of Nrf2/ARE signaling pathway is a potential chemopreventive or therapeutic strategy to treat diseases caused by oxidative damage. In the present study, we have found that treatment of Beas-2B cells with botrysphins D (BD) attenuated sodium arsenite [As (III)]-induced cell death and apoptosis. Meanwhile, BD was able to upregulate protein levels of Nrf2 and its downstream genes NQO1 and γ-GCS through inducing Nrf2 nuclear translocation, enhancing protein stability, and inhibiting ubiquitination. It was also found that BD-induced activation of the Nrf2/ARE pathway was regulated by PI3K, MEK1/2, PKC, and PERK kinases. Collectively, BD is a novel activator of Nrf2/ARE pathway, and is verified to be a potential preventive agent against oxidative stress-induced damage in human lung tissues.


Assuntos
Antioxidantes/farmacologia , Arsenitos/toxicidade , Diterpenos/farmacologia , Células Epiteliais/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Compostos de Sódio/toxicidade , Elementos de Resposta Antioxidante/efeitos dos fármacos , Antioxidantes/química , Arsênio/toxicidade , Ascomicetos/química , Morte Celular/efeitos dos fármacos , Linhagem Celular , Diterpenos/química , Células Epiteliais/citologia , Células Epiteliais/metabolismo , Humanos , Pulmão/citologia , Pulmão/efeitos dos fármacos , Pulmão/metabolismo , Fator 2 Relacionado a NF-E2/metabolismo , Transdução de Sinais/efeitos dos fármacos
10.
J Nat Prod ; 82(7): 1741-1751, 2019 07 26.
Artigo em Inglês | MEDLINE | ID: mdl-31268321

RESUMO

Nine new prenylated bibenzyls, radstrictins A-I (1-9), and 11 known congeners were obtained from the Chinese liverwort Radula constricta. Their structures were identified by analysis of HRMS, NMR, and electronic circular dichroism data. Radstrictins A-F (1-6) were isolated as a racemate or scalemic mixtures. All the isolated compounds were subjected to cytotoxicity assessment. Methyl 2,4-dihydroxy-3-(3-methyl-2-butenyl)-6-phenethylbenzoate (10) exhibited significant activity against human lung cancer cell lines A549 and NCI-H1299 with IC50 values of 6.0 and 5.1 µM, respectively. Further research revealed that cell death triggered by 10 occurred via mitochondria-derived paraptosis.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Bibenzilas/isolamento & purificação , Bibenzilas/farmacologia , Hepatófitas/química , Mitocôndrias/efeitos dos fármacos , Prenilação , Bibenzilas/química , Linhagem Celular Tumoral , Humanos , Estrutura Molecular , Análise Espectral/métodos
11.
Chem Biol Interact ; 310: 108741, 2019 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-31299238

RESUMO

Nuclear factor erythroid 2-related factor 2 (Nrf2) plays a key role in redox homeostasis. Activation of Nrf2 pathway by natural molecules effectively inhibits oxidants and toxicants-induced redox imbalance, and thus is able to intervene the onset and progression of many human diseases. In our previous study, a chalcone named as artocarmitin B (ACB), formed by artocarmitin A (ACA) and a trans-feruloyl substituent, was found to be a potential Nrf2 activator. In the present research, we found that ACB up-regulated the expressions of Nrf2, NAD(P)H: quinone oxidoreductase 1 (NQO1) and glutamate-cysteine ligase, modifier subunit (GCLM), inhibited Nrf2 degradation and promoted Nrf2 translocation to the nucleus under non-toxic doses. Moreover, ACB enhanced intracellular antioxidant capability in human lung epithelial cells through up-regulating reduced glutathione (GSH) level. Furthermore, ACB-induced activation of Nrf2 was related to the kinase pathways, including mitogen-activated protein kinase (MAPK), protein kinase C (PKC), phosphatidylinositol-4,5-bisphosphate 3-kinase (PI3K), and protein kinase R-like endoplasmic reticulum kinase (PERK). In terms of activation of Nrf2 pathway, ACB was more potent than ACA and ferulic acid (FA) individually or in combination. Collectively, our results indicate that ACB is an novel Nrf2 activator and enhances intracellular antioxidant capacity in human lung epithelial cells.


Assuntos
Antioxidantes/farmacologia , Chalcona/farmacologia , Células Epiteliais/metabolismo , Pulmão/citologia , Fator 2 Relacionado a NF-E2/metabolismo , Chalcona/uso terapêutico , Glutationa/metabolismo , Humanos , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Fator 2 Relacionado a NF-E2/efeitos dos fármacos , Transdução de Sinais
12.
Phytochemistry ; 158: 77-85, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30476899

RESUMO

Six previously undescribed labdane diterpenoids, frullanians A-F, along with five known diterpenoids, were isolated from the Chinese liverwort Frullania hamatiloba Stephani. Their structures were determined using NMR data, electronic circular dichroism (ECD) calculations as well as the single crystal X-ray diffraction measurement. NAD(P)H: QR (quinone reductase) assay demonstrated that frullanian D and four known compounds displayed antioxidant effect mediated via Nrf2 (Nuclear factor-erythroid 2-related factor 2) induction. Further investigation of the most bioactive frullanian D in MOVAS cells revealed that it ameliorated H2O2-induced oxidative insults without toxicity by increasing cell viability, attenuating morphological changes, and reducing intracellular ROS production. In addition, frullanian D promoted the nuclear translocation of Nrf2 and upregulated the expressions of antioxidant proteins NQO1 (NAD(P)H quinone oxidoreductase 1) and γ-GCS (γ-glutamyl cysteine synthetase). Docking analysis using MOE software further supported the activation of the Nrf2 pathway by frullanian D.


Assuntos
Antioxidantes/farmacologia , Diterpenos/farmacologia , Frullania/química , Fator 2 Relacionado a NF-E2/metabolismo , Animais , Antioxidantes/administração & dosagem , Antioxidantes/química , Linhagem Celular , Dicroísmo Circular , Cristalografia por Raios X , Diterpenos/administração & dosagem , Diterpenos/química , Avaliação Pré-Clínica de Medicamentos/métodos , Peróxido de Hidrogênio/toxicidade , Espectroscopia de Ressonância Magnética , Camundongos , Simulação de Acoplamento Molecular , Estrutura Molecular , NAD(P)H Desidrogenase (Quinona)/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Transdução de Sinais/efeitos dos fármacos
13.
Org Lett ; 20(20): 6550-6553, 2018 10 19.
Artigo em Inglês | MEDLINE | ID: mdl-30289265

RESUMO

Two novel ent-aromadendrane derivatives, plagiochianin A (1), possessing an unprecedented 2,3:6,7-di- seco-6,8-cyclo-aromadendrane carbon scaffold conjugated with three cyclic acetals, and plagiochianin B (2), an exceptional pyridine type aromadendrane alkaloid, were isolated from the Chinese liverwort Plagiochila duthiana. Their structures were established by comprehensive spectroscopic analysis coupled with single-crystal X-ray diffraction and electronic circular dichroism calculations. A plausible biogenetic pathway of these two compounds is presented, and their acetylcholinesterase inhibitory activities are preliminarily tested using TLC-bioautographic assays.

14.
J Nat Prod ; 79(9): 2149-57, 2016 09 23.
Artigo em Inglês | MEDLINE | ID: mdl-27556953

RESUMO

Twelve new heptaketides, biatriosporins A-L (1-12), biatriosporin M (13) (a ramulosin derivative), and 19 known compounds (14-32) were isolated from the endolichenic fungus Biatriospora sp. (8331C). The structures of these compounds were determined by analyzing MS and NMR data. The absolute configurations of compounds 1, 2, 7, and 9 were determined by single-crystal X-ray diffraction analysis, whereas compound 10 was deduced with Mosher's method. Four of the compounds were active in an antifungal assay. The most potent compound, compound 4, also sensitized clinically derived azole-resistant Candida albicans strains to fluconazole (FLC). A mechanistic investigation revealed that 4 inhibited the function of efflux pumps and reduced the transcriptional expression of the efflux-pump-related genes CDR1 and CDR2.


Assuntos
Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Ascomicetos/química , Policetídeos/isolamento & purificação , Policetídeos/farmacologia , Transportadores de Cassetes de Ligação de ATP/efeitos dos fármacos , Transportadores de Cassetes de Ligação de ATP/metabolismo , Antifúngicos/química , Candida albicans/efeitos dos fármacos , Farmacorresistência Fúngica/efeitos dos fármacos , Fluconazol/farmacologia , Líquens/microbiologia , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Policetídeos/química
15.
Chem Biodivers ; 13(12): 1685-1690, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-27448440

RESUMO

In our continuing program to find new bioactive compounds from the Chinese liverworts, four new kaurane-type diterpenoids, (6ß)-kaur-16-ene-6,9-diol (1), (6ß,12ß)-kaur-16-ene-6,9,12-triol (2), (6ß)-kaur-16-ene-5,6,9-triol (3), and kaur-16-ene-9,19-diol (4), have been isolated from the Chinese liverwort Jungermannia comata Nees. Five known kaurane-type diterpenoids (5 - 9) and four known trachylobane-type diterpenoids (10 - 13) were also obtained. The structures of the new compounds were established unequivocally on the basis of spectroscopic data. The absolute configuration of compound 1 was established by comparing experimental and calculated electronic circular dichroism spectra.


Assuntos
Diterpenos do Tipo Caurano/isolamento & purificação , Hepatófitas/química , China , Dicroísmo Circular , Diterpenos do Tipo Caurano/química , Conformação Molecular
16.
Planta Med ; 82(11-12): 1128-33, 2016 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-27336319

RESUMO

Seven new ent-eudesmane-type sesquiterpenoids (1-7) and six known analogues (8-13) were isolated from the Chinese liverwort Chiloscyphus polyanthus var. rivularis. Their structures were determined from analysis of MS and NMR spectroscopic data and single-crystal X-ray diffraction. A cytotoxic evaluation showed that compound 1 exhibited weak inhibitory activity against the A549 cancer cell line with an IC50 value of 27.7 µM.


Assuntos
Hepatófitas/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , China , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia
17.
J Asian Nat Prod Res ; 18(5): 409-14, 2016 May.
Artigo em Inglês | MEDLINE | ID: mdl-27025769

RESUMO

Three new drimane-type sesquiterpenoids chaetothyrins A-C (1-3), were isolated from an endolichenic fungus Chaetothyriales sp. (4341B). Their structures were determined by analysis of MS and NMR data as well as single-crystal X-ray diffraction analysis.


Assuntos
Ascomicetos/química , Sesquiterpenos/isolamento & purificação , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Modelos Moleculares , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos Policíclicos , Sesquiterpenos/química
18.
Fitoterapia ; 109: 1-7, 2016 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-26656409

RESUMO

Two new ent-prenylaromadendrane-type diterpenoids, diplotaxifols A (1) and B (2), a new ent-eudesmol, ent-eudesma-4(15),11(13)-dien-6α,12-diol (3), eight new eudesmanolides enantiomers (4-11) of the corresponding compounds from higher plants along with four known ent-eudesmanolides (12-15) were isolated from the 95% EtOH extract of Chinese liverwort Diplophyllum taxifolium. Their structures were elucidated on the basis of MS, NMR and IR spectral data, and confirmed by single-crystal X-ray diffraction analysis. The quinone reductase-inducing activity of the compounds was evaluated.


Assuntos
Diterpenos/química , Hepatófitas/química , Terpenos/química , Animais , Linhagem Celular Tumoral , Cristalografia por Raios X , Diterpenos/isolamento & purificação , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Quinona Redutases/metabolismo , Terpenos/isolamento & purificação
19.
J Asian Nat Prod Res ; 17(5): 462-7, 2015 May.
Artigo em Inglês | MEDLINE | ID: mdl-25677361

RESUMO

Three new polyacetylated labdane diterpenoids ptychantins P-R (1-3) and four known compounds (4-7) were isolated from an EtOH extract of the Chinese liverwort Ptychanthus striatus (Lehm. & Lindenb.) Nees. Their structures were established by extensive analysis of spectroscopic data (IR, UV, HRESIMS, 1D NMR, and 2D NMR).


Assuntos
Diterpenos/isolamento & purificação , China , Diterpenos/química , Hepatófitas/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular
20.
J Nat Prod ; 77(9): 2081-7, 2014 Sep 26.
Artigo em Inglês | MEDLINE | ID: mdl-25226363

RESUMO

Ten new dolabrane-type diterpenoids, notolutesins A-J (1-10), were isolated from the Chinese liverwort Notoscyphus lutescens, along with four known compounds. The structures of the new compounds were established on the basis of extensive spectroscopic data, and that of 1 was confirmed by single-crystal X-ray crystallography. The absolute configuration of 1 was determined by comparing its experimental and calculated electronic circular dichroism spectra. All of the isolates were evaluated for their cytotoxicity against a small panel of human cancer cell lines, and compound 1 exhibited an IC50 value of 6.2 µM against the PC3 human prostate cancer cell line.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Diterpenos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Hepatófitas/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Dicroísmo Circular , Cristalografia por Raios X , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Concentração Inibidora 50 , Masculino , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular
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