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1.
Phytochemistry ; 197: 113107, 2022 May.
Artigo em Inglês | MEDLINE | ID: mdl-35121215

RESUMO

Six alkaloids peharmalines F-K, along with 14 known ones, were isolated from the aerial part of Peganum harmala L.. The structures of the isolated compounds were determined based on their HR-ESI-MS data, extensive NMR spectroscopic analyses, and ECD calculations. 3-(4-Hydroxyphenyl)quinoline exhibited potent antiproliferative activity against the HepG-2 cell lines with an IC50 value of 3.05 µM. Norharmane displayed a moderate inhibition against A549 and HepG-2 cells with IC50 values of 16.45 µM and 17.27 µM, respectively.


Assuntos
Alcaloides , Antineoplásicos Fitogênicos , Peganum , Células A549 , Alcaloides/química , Antineoplásicos Fitogênicos/química , Células Hep G2 , Humanos , Peganum/química , Extratos Vegetais/química
2.
Chin J Nat Med ; 19(9): 686-692, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34561080

RESUMO

Six new tirucallane-type triterpenoids (1-6), along with ten known triterpenoids, were isolated from methylene chloride extract of the resin of Boswellia carterii Birdw. By the application of the comprehensive spectroscopic data, the structures of the compounds were clarified. The experimental electronic circular dichroism spectra were compared with those calculated, which allowed to assign the absolute configurations. Compounds 5 and 6 possesed a 2, 3-seco tirucallane-type triterpenoid skeleton, which were first reported. Their inhibitory activity against NO formation in LPS-activated BV-2 cells were evaluated. Compound 9 showed appreciable inhibitory effect, with an IC50 value of 7.58 ± 0.87 µmol·L-1.


Assuntos
Boswellia , Triterpenos , Estrutura Molecular , Resinas Vegetais , Triterpenos/farmacologia
3.
Org Lett ; 22(19): 7439-7442, 2020 10 02.
Artigo em Inglês | MEDLINE | ID: mdl-32886519

RESUMO

Baicalensines A (1) and B (2) were isolated from the roots of Thalictrum baicalense and structurally characterized using spectroscopic data, 13C NMR calculations, and the CASE algorithm. Compound 1, representing a new class of alkaloid dimers, contains berberine conjugated to a ring-opened isoquinoline. Compound 2 is the first reported natural benzylisoquinoline bearing a formyl group at C-3. Plausible biosynthetic pathways are proposed. Compound 1 exerted moderate cytotoxicity against the Caco-2 and HL-60 cell lines.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Berberina/farmacologia , Thalictrum/química , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Berberina/química , Berberina/isolamento & purificação , Células CACO-2 , Células HL-60 , Humanos , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Isoquinolinas/farmacologia , Estrutura Molecular , Raízes de Plantas/química
4.
Bioorg Chem ; 94: 103370, 2020 01.
Artigo em Inglês | MEDLINE | ID: mdl-31699388

RESUMO

Inspired by the intriguing structures and bioactivities of polyprenylated xanthones, ten previously undescribed polyprenylated xanthones, nujiangxanthones G-P (1-10), and fifteen known ones (11-25) were isolated from the twigs and leaves of Garcinia nujiangensis. The structures of these compounds were established on the basis of spectroscopic data as well as comparison with the literature. Most of the isolates showed potent cytotoxicity against selected cancer cells. Compound 8 showed the highest effects against MDA-MB-231 and A549 cell lines with IC50 values of 4.12 and 2.67 µM and 16 demonstrated the most potent activity against MCF-7 cell line with an IC50 value of 3.36 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Garcinia/química , Xantonas/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Relação Estrutura-Atividade , Xantonas/química , Xantonas/isolamento & purificação
5.
Fitoterapia ; 139: 104359, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31629049

RESUMO

Two new lignanamides, majusamides A and B (1 and 2), and two new alkaloids, chelidoniumine (3) and tetrahydrocoptisine N-oxide (4), together with six known hydroxycinnamic acid amides (HCCA) were isolated from the 75% ethanol extract of Chelidonium majus through the silica gel, Sephadex LH-20, MCI, ODS column chromatography, and semi-HPLC. Their structures were determined on the basis of spectroscopic data and physico-chemical methods. The absolute configurations of 1-3 were determined by electronic circular dichroism (ECD) calculations. The anti-inflammatory activities of all the isolates on the NO production in lipopolysaccharide (LPS)-induced macrophages were evaluated. Compounds 7 and 9 exhibited moderate inhibitory activity with IC50 values of 25.3 ±â€¯0.5 and 23.5 ±â€¯1.7 µM, respectively.


Assuntos
Alcaloides/farmacologia , Amidas/farmacologia , Anti-Inflamatórios/farmacologia , Chelidonium/química , Lignanas/farmacologia , Óxido Nítrico/metabolismo , Alcaloides/isolamento & purificação , Amidas/isolamento & purificação , Animais , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular , China , Lignanas/isolamento & purificação , Camundongos , Microglia/efeitos dos fármacos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química
6.
J Asian Nat Prod Res ; 21(7): 689-695, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-29781301

RESUMO

Three new compounds, ascotrichols A-B (1-2) and ascotrichrone A (3), along with two known isocoumarin derivatives (4-5), were isolated from the solid culture of a sea mud-derived fungus, Ascotricha sp. ZJ-M-5 on rice media. The structures were elucidated by extensive spectroscopic analyses, including 1D and 2D NMR data, and the absolute configurations were determined by electronic circular dichroism and biogenetic correlation.


Assuntos
Policetídeos/química , Xylariales/química , Dicroísmo Circular , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray
7.
J Asian Nat Prod Res ; 21(2): 134-140, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-29168395

RESUMO

The structures of pestalrones A-B were revised via reinterpretation of the NMR data and a brief chemical transformation from the co-occurring polyketides, in our investigation on the secondary metabolites of Pestalotiopsis zonata, which also afforded a new α-pyrone derivative, pestazonatic acid, and four known analogs.


Assuntos
Policetídeos/química , Pironas/química , Xylariales/química , Modelos Moleculares , Estrutura Molecular
8.
Steroids ; 138: 43-46, 2018 10.
Artigo em Inglês | MEDLINE | ID: mdl-30003909

RESUMO

A new hybrid of dehydroergosterol and nitrogenous alternariol derivative, pestauvicomorpholine A (1), and three alternariol analogues (2-4) including a new aminated one, pestauvicolactone A (2), were isolated from the fermentation product of the fungus Pestalotiopsis uvicola on rice media. Compounds 1 and 2 represent the first example of aza-alternariol and aza-alternariol-steroid derived from transamination followed by intermolecular hetero-Diels-Alder reaction.


Assuntos
Ergosterol/análogos & derivados , Lactonas/química , Lactonas/metabolismo , Xylariales/química , Xylariales/metabolismo , Ergosterol/química , Ergosterol/metabolismo , Estrutura Molecular , Nitrogênio/química , Nitrogênio/metabolismo , Estereoisomerismo
9.
J Nat Prod ; 81(4): 749-757, 2018 04 27.
Artigo em Inglês | MEDLINE | ID: mdl-29565129

RESUMO

With bioassay- and chemistry-guided fractionation, seven new caged prenylxanthones including two scalemic mixtures, epiisobractatin (1), 13-hydroxyisobractatin (2), 13-hydroxyepiisobractatin (3), 8-methoxy-8,8a-dihydrobractatin (4), 8-ethoxy-8,8a-dihydrobractatin (5), garcibracteatone (6), and 8-methoxy-8,8a-dihydroneobractiatin (7), and the eight known compounds 8-15 were isolated from the leaves of Garcinia bracteata. The structures were unambiguously elucidated through analysis of spectroscopic data. The 2D structures and relative configurations of 1 and 5 were confirmed by X-ray crystallographic analysis. The separation of the enantiomers of 1-5 was accomplished by chiral-phase HPLC. The absolute configurations of the enantiomers of 1 and 5 were assigned by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. The absolute configurations of the related compounds were determined via comparisons of their ECD data with those of the enantiomers of 1 and 5, respectively. Notably, compound 7, with a neo caged skeleton, is the first representative of a novel type of caged xanthone lacking a Δ8(8a) double bond. The isolated compounds exhibited significant cell growth inhibitory activities in vitro against human leukemic HL-60 and K562 cell lines, with GI50 values ranging from 0.2 to 8.8 µM. A preliminary structure-activity relationship is discussed.


Assuntos
Garcinia/química , Folhas de Planta/química , Xantonas/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Bioensaio/métodos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Dicroísmo Circular/métodos , Cristalografia por Raios X/métodos , Células HL-60 , Humanos , Células K562 , Relação Estrutura-Atividade , Xantonas/farmacologia
10.
Fitoterapia ; 127: 220-225, 2018 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-29474978

RESUMO

Bioassay-guided fractionation of the dichloromethane-soluble portion of the stems of Garcinia paucinervis led to the isolation of eight new xanthones, including three pairs of enantiomers, (+) and (-) paucinervins L-N (1a-3a, and 1b-3b), one optically pure compound, (-) paucinervin O (4), and one new analogue, paucinervin P (5), as well as thirteen known xanthones (6-18). Their structures were established by detailed analysis of extensive spectroscopic data. The absolute configurations of 1-4 were confirmed by ECD calculations. All the isolates 1-18 displayed antiproliferative effect against HL-60 with IC50 values ranging from 0.87 to 29.14 µM, of which compound 5 was the most active. Compounds 6, and 14 exhibited potential inhibitory activity against PC-3 cells, while compounds 5-7, 14, and 16-17 displayed cytotoxic potency against Caco-2 cells. A preliminary structure-activity relationship was also discussed.


Assuntos
Antineoplásicos Fitogênicos/química , Garcinia/química , Xantonas/química , Células CACO-2 , Células HL-60 , Humanos , Estrutura Molecular , Caules de Planta/química , Relação Estrutura-Atividade
11.
Fitoterapia ; 125: 155-160, 2018 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-29355750

RESUMO

Five pairs of new 2-oxoindole alkaloids, (±)-peganumalines A-E (1-5), and a new indole alkaloid, peganumaline F (6), along with two known analogues, were isolated from the seeds of Peganum harmala. Their structures and absolute configurations were elucidated through spectroscopic analyses and quantum chemistry calculations. Notably, (±)-peganumalines A (1) represent a pair of rare 2-oxoindole dimeric alkaloid enantiomer with the hitherto unknown carbon skeleton. All isolates were tested for antiproliferative and antibacterial activities.


Assuntos
Alcaloides Indólicos/química , Peganum/química , Sementes/química , Linhagem Celular Tumoral , Humanos , Alcaloides Indólicos/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular
12.
Fitoterapia ; 125: 235-239, 2018 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-29221703

RESUMO

Three new diterpenoids, ebractenoids O~Q (1-3), and a new phenolic glucoside, γ-pyrone-3-O-ß-d-(6-galloyl)-glucopyranoside (4), together with 6 known compounds, were isolated from the 95% ethanol extract of the roots of Euphorbia ebracteolata, and their structures were elucidated on the basis of spectroscopic data. The absolute configurations of 1-3 were determined by electronic circular dichroism (ECD) calculations. The inhibitory effects of all the isolates with exception of compounds 8 and 10 on the NO production in lipopolysaccharide (LPS)-induced macrophages were evaluated. All of them exhibited significant inhibitory activity.


Assuntos
Diterpenos/química , Euphorbia/química , Glucosídeos/química , Fenóis/química , Animais , Diterpenos/isolamento & purificação , Glucosídeos/isolamento & purificação , Lipopolissacarídeos , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Fenóis/isolamento & purificação , Raízes de Plantas/química , Células RAW 264.7
13.
Bioorg Med Chem Lett ; 28(2): 103-106, 2018 01 15.
Artigo em Inglês | MEDLINE | ID: mdl-29229205

RESUMO

Seventeen quinazoline alkaloids and derivatives, containing two pairs of new epimers, named as (S)- and (R)-1-(2-aminobenzyl)-3-hydroxypyrrolidin-2-one ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranoside (1, 2), (S)- and (R)-vasicinone ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranoside (3, 4), and a new enantiomer (12b), together with six known ones (5-8, 10, and 12a), and three pairs of known enantiomers (9, 11, and 13), were isolated from the ethanol extracts of the seeds of Peganum harmala L.. Their structures including the absolute configuration were elucidated by using 1D and 2D NMR, and ECD calculation approaches. The cytotoxic activities of all isolated compounds were evaluated. 11 showed moderate cytotoxicity against PC-3 cells with an IC50 value of 15.41 µM.


Assuntos
Alcaloides/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Peganum/química , Quinazolinas/farmacologia , Sementes/química , Alcaloides/química , Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Quinazolinas/química , Quinazolinas/isolamento & purificação , Relação Estrutura-Atividade
14.
J Nat Prod ; 80(11): 2893-2904, 2017 11 22.
Artigo em Inglês | MEDLINE | ID: mdl-29131616

RESUMO

Inspired by the intriguing structures and bioactivities of dimeric alkaloids, 11 new thalifaberine-type aporphine-benzylisoquinoline alkaloids, thalicultratines A-K, a tetrahydroprotoberberine-aporphine alkaloid, thalicultratine L, and five known ones were isolated from the roots of Thalictrum cultratum. Their structures were defined on the basis of NMR and HRESIMS data. The antiproliferative activities of compounds 1-17 were evaluated against human leukemia HL-60 and prostate cancer PC-3 cells. Most alkaloids showed potent cytotoxicity against selected cancer cells. Preliminary SARs are discussed. The most active new compound (3), with an IC50 value of 1.06 µM against HL-60 cells, was selected for mechanism of action studies. The results revealed that compound 3 induced apoptosis and arrested the HL-60 cell cycle at the S phase with the loss of mitochondria membrane potential. The nuclear morphological Hoechst 33258 staining assay was also carried out, and the results confirmed apoptosis.


Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Aporfinas/isolamento & purificação , Aporfinas/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Raízes de Plantas/química , Thalictrum/química , Alcaloides/química , Antineoplásicos Fitogênicos/química , Aporfinas/química , Alcaloides de Berberina , Medicamentos de Ervas Chinesas/química , Células HL-60 , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Relação Estrutura-Atividade
15.
Org Biomol Chem ; 15(22): 4901-4906, 2017 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-28541369

RESUMO

Neobraclactones A-C (1-3), featuring an unprecedented further rearranged prenylxanthone skeleton with a unique octahydro-2H-1,3-dioxacyclopenta[c,d]inden-2-one scaffold, along with their biosynthesis-related known compound neobractatin (4), were isolated from the leaves of Garcinia bracteata. Their structures with absolute configurations were determined by extensive analyses of spectroscopic data and ECD calculations. Compounds 1 and 2 showed significant growth inhibition activities against the human leukaemia HL-60 and K562 cell lines with GI50 values from 0.40 to 0.86 µM.


Assuntos
Garcinia/química , Xantonas/isolamento & purificação , Conformação Molecular , Xantonas/química
16.
Bioorg Med Chem Lett ; 27(10): 2161-2165, 2017 05 15.
Artigo em Inglês | MEDLINE | ID: mdl-28377060

RESUMO

Three new (1-3) and one known (4) bioactive terpenoids were isolated from the seeds of Silybum marianum based on the investigation to get new NO inhibitors. Their structures were determined by extensive NMR (1D and 2D NMR) and MS spectroscopic data, and the absolute configurations were identified by experimental and calculated ECD spectra. The NO inhibitory activities in murine microglial BV-2 cells and interactions with iNOS protein by molecular docking were evaluated for all compounds. The results showed that these compounds had potent NO inhibitory effects.


Assuntos
Cardo-Mariano/química , Óxido Nítrico Sintase Tipo II/metabolismo , Óxido Nítrico/metabolismo , Terpenos/química , Animais , Sítios de Ligação , Linhagem Celular , Dicroísmo Circular , Lipopolissacarídeos/toxicidade , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Cardo-Mariano/metabolismo , Conformação Molecular , Simulação de Acoplamento Molecular , Neurônios/citologia , Neurônios/efeitos dos fármacos , Neurônios/metabolismo , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Extratos Vegetais/química , Estrutura Terciária de Proteína , Sementes/química , Sementes/metabolismo , Terpenos/isolamento & purificação , Terpenos/farmacologia
17.
Fitoterapia ; 119: 83-89, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-28400224

RESUMO

Two new amide compounds, mariamides A and B (1-2), were obtained together with fourteen known compounds from the seeds of milk thistle (Silybum marianum). Their structures were established on the basis of extensive 1D and 2D NMR analyses, as well as HR-ESI-MS data. Most of the compounds showed significant antioxidant activities than positive control in ABTS and FRAP assays. However, only amide compounds 1-4 showed moderate DPPH radical scavenging activity and compounds 7 and 16 showed the most potent activity against DPPH. Most of the compounds showed moderate to stronger α-glucosidase inhibitory activities. Nevertheless, only flavonoids showed strong PTP1B inhibitory activities. These results indicate a use of milk thistle seed extracts as promising antioxidant and antidiabetic agents.


Assuntos
Amidas/química , Sequestradores de Radicais Livres/química , Hipoglicemiantes/química , Cardo-Mariano/química , Amidas/isolamento & purificação , Flavonoides/química , Sequestradores de Radicais Livres/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Humanos , Hipoglicemiantes/isolamento & purificação , Estrutura Molecular , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Sementes/química , alfa-Glucosidases
18.
J Asian Nat Prod Res ; 19(7): 673-677, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28276771

RESUMO

Two new d-threitol orsellinates (1-2) were isolated from the EtOAc extract of a sea mud-derived fungus, Ascotricha sp. ZJ-M-5, cultured in Czapek Dox broth. These two compounds featured in the symmetrical substitution of orsellinic acid or acetic acid, which was established on the basis of 1D and 2D NMR experiments. The characteristic optical rotations enabled the assignment of the absolute configuration.


Assuntos
Resorcinóis/isolamento & purificação , Álcoois Açúcares/isolamento & purificação , Xylariales/química , Ácido Acético/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Resorcinóis/química , Álcoois Açúcares/química
19.
J Nat Prod ; 80(2): 551-559, 2017 02 24.
Artigo em Inglês | MEDLINE | ID: mdl-28128938

RESUMO

Investigation of the alkaloids from Peganum harmala seeds yielded two pairs of unique racemic pyrroloindole alkaloids, (±)-peganines A-B (1-2); two rare thiazole derivatives, peganumals A-B (3-4); six new ß-carboline alkaloids, pegaharmines F-K (5-10); and 12 known analogues. Their structures, including stereochemistry, were elucidated through spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray diffraction. Notably, the incorporation of pyrrole and indole moieties in peganines A-B, thiazole fragments in peganumals A-B, and a C-1 α,ß-unsaturated ester motif in pegaharmine F (5) are all rare, and their presence in the genus Peganum were demonstrated for the first time. All isolates were tested for antiproliferative activities against the HL-60, PC-3, and SGC-7901 cancer cell lines, and compounds 9, 11, 12, and 13 exhibited moderate cytotoxicity against HL-60 cancer cell lines with IC50 values in the range of 4.36-9.25 µM.


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Alcaloides Indólicos/química , Alcaloides Indólicos/isolamento & purificação , Peganum/química , Sementes/química , Antineoplásicos Fitogênicos/farmacologia , Carbolinas/química , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/farmacologia , Células HL-60 , Humanos , Alcaloides Indólicos/farmacologia , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular
20.
Fitoterapia ; 112: 222-8, 2016 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-27316977

RESUMO

Investigation of the roots of Flemingia philippinensis resulted in the isolation of two new chalcones, flemiphilippinones B (1) and C (2), and one new pterocarpoid, demethylwedelolactone-11-methyl ether (3), together with 12 known compounds (4-15). The antiproliferative activity against PC-3 cells was evaluated and most compounds showed cytotoxicity, among which, compound 2 exhibited GI50 value of 14.12µM. The antiproliferative activity of 2 against Bel-7402 and CaEs-17 cells was also measured, with GI50 values of 1.91 and 2.58µM, respectively. Intensive mechanism study showed that 2 caused cell-cycle arrest at S/G2 phase and induced apoptosis in Bel-7402 cells through mitochondria-related pathway.


Assuntos
Chalconas/química , Fabaceae/química , Raízes de Plantas/química , Pterocarpanos/química , Apoptose , Pontos de Checagem do Ciclo Celular , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Chalconas/isolamento & purificação , Humanos , Estrutura Molecular , Pterocarpanos/isolamento & purificação
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