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1.
Eur Phys J E Soft Matter ; 45(8): 64, 2022 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-35917038

RESUMO

The tendency to crystallize was studied in the selected monohydroxy alcohols: 1-chloro-2-methyl-2-propanol, 1-chloro-2-propanol, 3-chloro-1-propanol, and 8-chloro-1-octanol. Performed calorimetric measurements have proved that the differences in structures of tested alcohols influence the tendency to crystallization. At a sufficiently fast heating rate, no crystallization was observed in the case of 1-chloro-2-propanol and 3-chloro-1-propanol, contrary to other two alcohols. The obtained results suggest that elongation of the alkyl chain or adding a methyl group to the hydrocarbon backbone increases the susceptibility to crystallization.


Assuntos
Álcoois , Álcoois/química , Cristalização , Estrutura Molecular
2.
Acta Crystallogr C Struct Chem ; 78(Pt 8): 437-448, 2022 08 01.
Artigo em Inglês | MEDLINE | ID: mdl-35924362

RESUMO

Creatinine, a biologically important compound, is used to analyze kidney function and kidney diseases in the human body. The salt form of creatinine is used in the formation of drug materials like anti-HIV, antifungal, antiprotozoal, antiviral and antitumour compounds. Here we report the solid-state structures of three new crystalline salts, namely, creatininium (2-amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium) bromide, C4H8N3O+·Br-, (I), creatininium 3-aminobenzoate, C4H8N3O+·C7H6NO2-, (II), and creatininium 3,5-dinitrobenzoate, C4H8N3O+·C7H3N2O6-, (III). These salts have been synthesized and characterized by single-crystal X-ray diffraction and Hirshfeld surface analysis. The structural chemistry of salts (I)-(III) and their crystal packing are discussed in detail. The primary interaction between the creatinine cation and the acid anion in the three salts is N-H...Br/O hydrogen bonds. In salt (I), the creatinine cation and bromide anion are connected through a pair of N-H...Br hydrogen bonds forming R42(8) and R42(12) ring motifs. In salts (II) and (III), the creatinine cation interacts with the corresponding anion via a pair of N-H...O hydrogen bonds. The crystal structure is further stabilized by C-H...O and O-H...O hydrogen bonds with the ring motifs R22(8), R21(7) and R21(6). Furthermore, the crystal structures are stabilized by π-π, C-H...π, C-O...π and N-O...π stacking interactions. The contributions made by each hydrogen bond in maintaining the crystal structure stability has been quantified by Hirshfeld surface analysis.


Assuntos
Ácido Bromídrico , Sais , Brometos , Creatinina , Cristalografia por Raios X , Humanos , Ligação de Hidrogênio , Estrutura Molecular , Nitrobenzoatos , Sais/química , meta-Aminobenzoatos
3.
J Am Chem Soc ; 144(31): 14047-14052, 2022 Aug 10.
Artigo em Inglês | MEDLINE | ID: mdl-35916403

RESUMO

Directly editing an all-carbon quaternary carbon itself of nonstrained acyclic molecules remains underexploited despite the recent advances in the fields of both C-H and C-C bond activation. Herein, we report a palladium-catalyzed migrative carbofluorination of saturated amides enabled by the activation of both the C(sp3)-H and the Cquaternary-Cσ bonds. In this transformation, the α-quaternary carbon of Weinreb amides is converted to α-tertiary fluoride with concurrent migration of an aryl or an amido group from the α- to ß-carbon. DFT calculations indicate that the dyotropic rearrangement proceeds through an unusual anti-selective [2.1.0] bicyclic transition state. The reaction, compatible with a broad range of functional groups, is stereospecific and is applicable to the synthesis of enantioenriched products.


Assuntos
Amidas , Paládio , Amidas/química , Carbono/química , Catálise , Estrutura Molecular , Paládio/química
4.
J Antibiot (Tokyo) ; 75(9): 523-525, 2022 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-35918477

RESUMO

A new member of ß-carboline alkaloids, Marinacarboline glucuronide (1), along with nine known compounds (2-10), were isolated from static liquid fermentation extracts of Actinoalloteichus cyanogriseus LHW52806 isolated from the marine sponge Phakellia fusca. Their structures were elucidated by NMR, mass spectrometry and single-crystal X-ray diffraction. All compounds exhibited neither antimicrobial activity nor cytotoxicity. Compounds 1, 8 and 10 showed anti-inflammatory potential of significant decreasing the expressions of IL- 6 in vitro at 20 µM.


Assuntos
Actinobacteria , Actinomycetales , Alcaloides , Poríferos , Actinobacteria/química , Actinomycetales/química , Alcaloides/química , Animais , Carbolinas/química , Carbolinas/farmacologia , Glucuronídeos , Estrutura Molecular
5.
J Antibiot (Tokyo) ; 75(9): 526-529, 2022 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-35918478

RESUMO

One new xanthene derivative, named penicixanthene E (1), together with one known compound 2, was isolated from the EtOAc extract of the endophytic fungus Penicillium sp. GXIMD 03101, which was identified from the mangrove Acanthus ilicifolius L. collected in the South China Sea. The structure of 1 was elucidated by 1D and 2D NMR spectral interpretation and HREISMS data. The absolute configurations of C-9 and C-11 in 1 were proposed based on electronic circular dichroism (ECD), but the configuration at C-3 in 1 was unassigned. Compound 1 represents a xanthene derivative that was first reported, in which carbon-carbon double bond has been reduced. The cytotoxic activities of all compounds were evaluated, the result showed that compound 1 has weak activity against pancreatic cancer SW1990.


Assuntos
Penicillium , Carbono , Dicroísmo Circular , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Penicillium/química , Xantenos/farmacologia
6.
Sci Rep ; 12(1): 13570, 2022 Aug 09.
Artigo em Inglês | MEDLINE | ID: mdl-35945234

RESUMO

Spongian diterpenes are a group of marine natural compounds possessing various biological activities. However, their anticancer activity is still poorly studied and understood. We isolated six spongian diterpenes from the marine sponge Spongionella sp., including one new spongionellol A and five previously known molecules. The structures were elucidated using a detailed analysis MS and NMR spectra as well as by comparison with previously reported data. Two of them, namely, spongionellol A and 15,16-dideoxy-15α,17ß-dihydroxy-15,17-oxidospongian-16-carboxylate-15,17-diacetate exhibited high activity and selectivity in human prostate cancer cells, including cells resistant to hormonal therapy and docetaxel. The mechanism of action has been identified as caspase-dependent apoptosis. Remarkably, both compounds were able to suppress expression of androgen receptor (AR) and AR-splice variant 7, as well as AR-dependent signaling. The isolated diterpenes effectively inhibited drug efflux mediated by multidrug-resistance protein 1 (MDR1; p-glycoprotein). Of note, a synergistic effect of the compounds with docetaxel, a substrate of p-glycoprotein, suggests resensitization of p-glycoprotein overexpressing cells to standard chemotherapy. In conclusion, the isolated spongian diterpenes possess high activity and selectivity towards prostate cancer cells combined with the ability to inhibit one of the main drug-resistance mechanism. This makes them promising candidates for combinational anticancer therapy.


Assuntos
Diterpenos , Poríferos , Neoplasias da Próstata , Subfamília B de Transportador de Cassetes de Ligação de ATP/metabolismo , Membro 1 da Subfamília B de Cassetes de Ligação de ATP/metabolismo , Animais , Diterpenos/química , Docetaxel/farmacologia , Resistência a Medicamentos , Humanos , Masculino , Estrutura Molecular , Poríferos/metabolismo , Neoplasias da Próstata/tratamento farmacológico
7.
Mar Drugs ; 20(8)2022 Jul 25.
Artigo em Inglês | MEDLINE | ID: mdl-35892943

RESUMO

New carboxamides, (±)-vochysiamide C (1) and (+)-vochysiamide B (2), and a new polyketide, 4S,3aS,9aR-3a,9a-deoxy-3a hydroxy-1-dehydroxyarthrinone (3), were isolated and identified from the sponge-derived fungus Arthrinium sp. SCSIO 41421, together with other fifteen known natural products (4-18). Their structures including absolute configurations were determined by detailed NMR, MS spectroscopic analyses, calculated electronic circular dichroism (ECD), as well as quantum-chemical NMR calculations. Preliminary bioactivity screening and molecular docking analysis revealed that several natural products exhibited obvious enzyme inhibitory activities against acetylcholinesterase (AChE), such as 2,3,6,8-tetrahydroxy-1-methylxanthone (4) with an inhibitory rate 86% at 50 µg/mL.


Assuntos
Produtos Biológicos , Policetídeos , Xylariales , Acetilcolinesterase , Produtos Biológicos/farmacologia , Dicroísmo Circular , Simulação de Acoplamento Molecular , Estrutura Molecular , Policetídeos/química , Xylariales/química
8.
Chem Commun (Camb) ; 58(60): 8400-8403, 2022 Jul 26.
Artigo em Inglês | MEDLINE | ID: mdl-35796040

RESUMO

Organic photoredox-catalyzed alkylamination of olefins is performed with alkyl halides and nitrile solvent by blocking the traditional photoredox-ATRA process with Zn(OAc)2. A range of carbon-centered radicals (α-alkylcarbonyl, benzyl, cyanomethyl) are effectively participating in this strategy giving rise to versatile carboamination products with high synthetic value.


Assuntos
Alcenos , Acetato de Zinco , Carbono , Catálise , Estrutura Molecular
9.
Chem Commun (Camb) ; 58(60): 8424-8427, 2022 Jul 26.
Artigo em Inglês | MEDLINE | ID: mdl-35796310

RESUMO

The base-mediated anti-Markovnikov hydroamination of functionally varied styrenes with amino-substituted pyridine, quinoline, pyrimidine, pyrazine, and phenanthridine with excellent regioselectivity has been described. Double hydroamination was observed chemoselectively on the secondary amine, leaving the primary amine intact. Experimental evidence suggests that the proposed reaction involves the nucleophilic addition of the aminopyridyl radical onto vinyl arenes via a single electron transfer.


Assuntos
Estirenos , Elementos de Transição , Aminação , Aminas , Catálise , Estrutura Molecular
10.
J Am Chem Soc ; 144(29): 13071-13078, 2022 Jul 27.
Artigo em Inglês | MEDLINE | ID: mdl-35830595

RESUMO

Despite the frequent occurrence of γ-branched amines in bioactive molecules, the direct catalytic asymmetric synthesis of this structural motif containing a remote stereocenter remains an important synthetic challenge. Here, we report an amide-directed, rhodium-catalyzed highly diastereo- and enantioselective hydroboration of unactivated internal alkenes. This method provided facile access to enantioenriched amines containing ß,γ-vicinal stereocenters. The application of this strategy to the synthesis of bioactive molecules was demonstrated. Computational studies indicated that migratory insertion of the alkene into rhodium hydride controls the enantioselectivity.


Assuntos
Ródio , Alcenos/química , Amidas/química , Aminas , Catálise , Estrutura Molecular , Ródio/química , Estereoisomerismo
11.
J Am Chem Soc ; 144(29): 13374-13383, 2022 Jul 27.
Artigo em Inglês | MEDLINE | ID: mdl-35833747

RESUMO

Random copolymerization is an effective approach to synthesize the desired polymers by harmonizing distinct properties of different monomers. For supramolecular polymers in which monomer binding is inherently dynamic, it is difficult to achieve random copolymerization of monomers with distinct molecular structures and properties due to an enthalpic advantage upon self-recognition (self-sorting). Herein, we demonstrate an example of thermodynamically controlled random supramolecular copolymerization of two monomers functionalized with barbituric acid via the formation of six-membered hydrogen-bonded rosette intermediates to exhibit structural harmonization of the two main-chain motifs, i.e., intrinsically curved and linear motifs. One monomer based on naphthalene chromophore exclusively forms toroidal fibers, whereas another one bearing additional photoreactive diacetylene moiety affords linearly elongated fibers. Supramolecular copolymerization of the two monomers is achieved by cooling hot monomer mixtures in a nonpolar solvent, which results in the formation of thermodynamically stable spirally folded yet elongated fibers. Atomic force microscopic observations and theoretical simulations of the experimental data obtained by absorption spectroscopy reveal the homopolymerization of the diacetylene-functionalized monomer in the high-temperature region, followed by the incorporation of the naphthalene monomer in the medium-temperature region to form supramolecular copolymers with random monomer sequence. Finally, we demonstrate that the random copolymerization process can be switched to a narcissistically self-sorting one by deactivating monomer exchange through the photo-cross-linking of the diacetylene-functionalized monomers.


Assuntos
Naftalenos , Polímeros , Estrutura Molecular , Polimerização , Polímeros/química , Temperatura
12.
J Agric Food Chem ; 70(29): 8986-8993, 2022 Jul 27.
Artigo em Inglês | MEDLINE | ID: mdl-35848390

RESUMO

A series of aryloxyacetic acid derivatives have demonstrated promising herbicidal performance by inhibition of the hydroxyphenylpyruvate deoxygenase (HPPD) enzyme. We hereby applied quantitative structure-activity relationship (QSAR) and docking strategies to model and chemically understand the bioactivities of these compounds and subsequently propose unprecedented analogues aiming at improving the herbicidal and environmental properties. Bulky halogens at the 2-, 3-, 4-, and 6-positions of an aromatic ring, CF3 in 4-position, and the 2-NO2 group in a phenyl ring appear to favor the HPPD inhibition. At the same time, Me and OMe substituents contribute to decreasing the pKi values. Accordingly, a few compounds were proposed and the candidate with 2,4,6-triBr substituents demonstrated an estimated pKi similar to those of the best library compounds. This finding was corroborated by the docking scores of the ligand-enzyme interactions. In addition, the high calculated lipophilicity of some proposed agrochemicals suggests that they should have low soil mobility and, therefore, are not prone to easily leach out and reach groundwater, despite causing other ecological issues.


Assuntos
4-Hidroxifenilpiruvato Dioxigenase , Herbicidas , Computadores , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Herbicidas/química , Herbicidas/farmacologia , Estrutura Molecular , Relação Quantitativa Estrutura-Atividade
13.
Mar Drugs ; 20(7)2022 Jun 22.
Artigo em Inglês | MEDLINE | ID: mdl-35877701

RESUMO

Four new drimane sesquiterpenoids (1-4) and three known ones (5-7) were isolated from the fermentation broth of the mangrove-derived Aspergillus ustus 094102. Compound 5 was further resolved as four purified compounds 5a-5d. By means of extensive spectroscopic and ECD analysis as well as the chemical transformation, their structures were identified as (2R,3R,5S,9R,10S)-2,3,9,11-tetrahydroxydrim-7-en-6-one (ustusol F, 1), (2R,3R,5R,9S,10R)-2,3,11-trihydroxydrim-7-en-6-one (9-deoxyustusol F, 2), (3S,5R,9R,10R)-3,11,12-trihydroxydrim-7-en-6-one (ustusol G, 3), (5S,6R,9S,10S, 11R,2'E,4'E)-(11-dideoxy-11-hydroxystrobilactone A-6-yl)-5-carboxypenta-2,4-dienoate (ustusolate H, 4), ((5S,6R,9S,10S)-strobilactone A-6-yl) (2E,4E)-6,7-dihydroxyocta-2,4-dienoate (ustusolate I, 5), (2'E,4'E;6',7'-erythro)-ustusolate I (5a) and (2'E,4'E;ent-6',7'-erythro)-ustusolate I (5b), (2'E,4'E,6'R,7'R)-ustusolate I (5c) and (2'E,4'E,6'S,7'S)-ustusolate I (5d), (5S,6R,9S,10S,2'E,4'E)-(strobilactone A-6-yl)-5-carboxypenta-2,4-dienoate (ustusolate J, 6), and (2S,5S,9R,10S)-2,9,11-trihydroxydrim-7-en-6-one (ustusol B, 7), respectively. Compound 5 showed antiproliferation against the human tumor cells CAL-62 and MG-63 with the IC50 values of 16.3 and 10.1 µM, respectively.


Assuntos
Sesquiterpenos , Aspergillus , Humanos , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia
14.
Mar Drugs ; 20(7)2022 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-35877703

RESUMO

Four novel monocyclic cyclopropane acids, namely, sydocyclopropanes A-D (1-4), along with one known congener hamavellone B (5), were isolated from the Aspergillus sydowii MCCC 3A00324 fungus, which was isolated from the deep-sea sediment. The gross structures of novel compounds were established by detailed analyses of the spectroscopic data (HRESIMS and NMR spectra), and their absolute configurations were resolved on the basis of the quantum chemical calculations of ECD and NMR data, in association with DP4+ probability analyses. Sydocyclopropanes A-D, featuring the 1,1,2,3-tetrasubstituted cyclopropane nucleus with different lengthy alkyl side chains, were discovered in nature for the first time. All compounds exhibited antiviral activities against A/WSN/33 (H1N1), with IC50 values ranging from 26.7 to 77.2 µM, of which compound 1 exhibited a moderate inhibitory effect (IC50 = 26.7 µM).


Assuntos
Antivirais , Vírus da Influenza A Subtipo H1N1 , Antivirais/química , Aspergillus/química , Ciclopropanos/farmacologia , Estrutura Molecular
15.
Mar Drugs ; 20(7)2022 Jul 06.
Artigo em Inglês | MEDLINE | ID: mdl-35877736

RESUMO

Four novel, rare carbon-bridged citrinin dimers, namely dicitrinones G-J (1-4), and five known analogs (5-9) were isolated from the starfish-derived fungus Penicillium sp. GGF 16-1-2. Their structures were elucidated by extensive spectroscopic analysis and quantum chemical calculations. Compounds 1-9 exhibited strong antifungal activities against Colletotrichum gloeosporioides with LD50 values from 0.61 µg/mL to 16.14 µg/mL. Meanwhile, all compounds were evaluated for their cytotoxic activities against human pancreatic cancer BXPC-3 and PANC-1 cell lines; as a result, compound 1 showed more significant cytotoxicities than the positive control against both cell lines. In addition, based on the analyses of the protein-protein interaction (PPI) network and Western blot, 1 could induce apoptosis by activating caspase 3 proteins (CASP3).


Assuntos
Citrinina , Penicillium , Animais , Carbono/metabolismo , Citrinina/química , Fungos , Humanos , Estrutura Molecular , Penicillium/química , Estrelas-do-Mar
16.
Mar Drugs ; 20(7)2022 Jul 09.
Artigo em Inglês | MEDLINE | ID: mdl-35877742

RESUMO

Two new phenylhydrazone derivatives and one new alkaloid, penzonemycins A-B (1-2) and demethylmycemycin A (3), together with three known compounds including an alkaloid (4) and two sesquiterpenoids (5-6), were isolated from the Streptomyces sp. SCSIO 40020 obtained from the Pearl River Estuary sediment. Their structures and absolute configurations were assigned by 1D/2D NMR, mass spectroscopy and X-ray crystallography. Compound 1 was evaluated in four human cancer cell lines by the SRB method and displayed weak cytotoxicity in three cancer cell lines, with IC50 values that ranged from 30.44 to 61.92 µM, which were comparable to those of the positive control cisplatin. Bioinformatic analysis of the putative biosynthetic gene cluster indicated a Japp-Klingemann coupling reaction involved in the hydrazone formation of 1 and 2.


Assuntos
Alcaloides , Streptomyces , Estuários , Humanos , Hidrazonas , Estrutura Molecular , Rios , Streptomyces/química , Streptomyces/genética
17.
Mar Drugs ; 20(7)2022 Jul 12.
Artigo em Inglês | MEDLINE | ID: mdl-35877747

RESUMO

Twelve new and four known alkaloids including five different structural scaffolds were isolated from the sponge Stylissa massa collected in the South China Sea. Compound 1 is the first identified precursor metabolite of the classic 5/7/5 tricyclic skeleton with unesterified guanidine and carboxyl groups, compounds 2-5 and 13-15 belong to the spongiacidin-type pyrrole imidazole alkaloids (PIAs). Z- and E-configurations of the spongiacidin-type PIAs often appeared concomitantly and were distinguished by the chemical shift analysis of 13C NMR spectra. The structures of all twelve new compounds were determined by NMR, MS, and ECD analysis combined with single-crystal data of compounds 1, 5, and 10. In the aldose reductase (ALR2) inhibitory assay, six 5/7/5 tricyclic compounds (2-5, 13-15) displayed significant activities. Compounds 13 and 14, as the representative members of spongiacidin-PIAs, demonstrated their ALR2-targeted activities in SPR experiments with KD values of 12.5 and 6.9 µM, respectively.


Assuntos
Alcaloides , Poríferos , Alcaloides/química , Alcaloides/farmacologia , Animais , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Pirróis/química , Pirróis/farmacologia
18.
Mar Drugs ; 20(7)2022 Jul 20.
Artigo em Inglês | MEDLINE | ID: mdl-35877757

RESUMO

Three new glycosylated secondary metabolites, including a new indole alkaloid, pityriacitrin D (1), and two new trehalose lipids (2 and 3), together with three known compounds (4-6) were isolated from two marine-derived bacterial strains, Bacillus siamensis 168CLC-66.1 and Tsukamurella pseudospumae IV19-045. The structures of 1-3 were determined by extensive analysis and comparison of their spectroscopic data with literature values. The absolute configurations of sugar moieties were determined by chemical derivatization followed by LC-MS analysis. Cytotoxicity of 1-3 against six cancer cell lines was evaluated by SRB assay, and 1 showed moderate activity against all the tested cell lines with GI50 values ranging from 8.0 to 10.9 µM.


Assuntos
Actinomycetales , Bactérias , Estrutura Molecular
19.
J Med Chem ; 65(13): 9281-9294, 2022 07 14.
Artigo em Inglês | MEDLINE | ID: mdl-35776775

RESUMO

A series of new (tricarbonyl)rhenium(I) complexes were synthesized using chiral bidentate ligands (+)/(-)-iminopyridines (LR/LS). The reaction yielded a mixture of mononuclear Re(I) diastereoisomers, formulated as fac-[Br(CO)3Re(S/R)L(S/R)]. Each single diastereoisomer was isolated and fully characterized. X-ray crystallography and circular dichroism spectra verified their enantiomeric nature. The cytotoxicity of each complex was evaluated against six cancer cell lines. The effect of the two complexes on viability, proliferation, and migration was analyzed on glioblastoma cell lines (U251 and LN229). Changes in the expression of histones, apoptotic, and key signaling proteins, as well as alterations in DNA structure, were also observed. These experiments showed that the chirality associated with both metal and ligand has a strong influence on cytotoxicity.


Assuntos
Glioblastoma , Rênio , Cristalografia por Raios X , Glioblastoma/tratamento farmacológico , Humanos , Ligantes , Modelos Moleculares , Estrutura Molecular , Rênio/química
20.
Chem Biodivers ; 19(7): e202200463, 2022 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-35785443

RESUMO

A new amide (1), two new phenylpropanoid derivatives (2, 3), along with three new natural products, including three nitrogen chirality compounds, N-(3-methoxy-1,3-dioxopropyl)-D-phenylalanine methyl ester (4), N-(3-methoxy-1,3-dioxopropyl)-L-phenylalanine methyl ester (5), and N-acetyl-L-phenylalanine methyl ester (6), as well as dimethyl (2R,3R)-2-hydroxy-3-(((E)-3-(4-hydroxyphenyl)acryloyl)oxy)succinate (7) and dimethyl (S,E)-2-((3-(4-hydroxy-3-methoxyphenyl)acryloyl)oxy)succinate (8) were isolated from Delphinium kamaonense Hunth. Their structures were elucidated by extensive analysis of 1D and 2D NMR, and HR-ESI-MS experiments, and the absolute configurations were determined by comparative analysis of specific optical rotation. Compound 1 exhibited a moderate cytotoxicity effect against Hep-3B cancer cell lines (IC50 41.39±0.13 µM) and an excellent antioxidant activity (IC50 0.527±0.06 µM in ABTS assay, and 1.235±0.09 µM in DPPH assay, respectively), which was superior to vitamin C in ABTS (IC50 1.670±0.07 µM) and DPPH (IC50 19.10±0.40 µM) methods.


Assuntos
Antineoplásicos , Delphinium , Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Delphinium/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Succinatos
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