RESUMO
Two new prenylated flavanones, pazentin A (3',4'-dihydroxy-6,2'-diprenylpinocembrin, 1) and pazentin B [4'-hydroxy-2'-methoxy-5'-(1â´, 1â´-dimethylallyl)-6-prenylpinocembrin, 2] together with two known ones (3 and 4) previously isolated from other Dalea species were obtained from the benzene extract of Dalea pazensis Rusby roots. The compounds were evaluated in vitro for their inhibition on mushroom tyrosinase enzyme and in relation to their effect on melanogenesis in B16 murine melanoma cells, by using a spectrophotometric method. The information obtained could be relevant to the knowledge of the structure-activity relationship for these flavonoids with the aim to explore the rational design for skin-whitening agents.
Assuntos
Agaricales/enzimologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Fabaceae/química , Flavanonas/química , Flavanonas/farmacologia , Melaninas/metabolismo , Monofenol Mono-Oxigenase/antagonistas & inibidores , Animais , Linhagem Celular Tumoral , Camundongos , Monofenol Mono-Oxigenase/metabolismo , Raízes de Plantas/química , PrenilaçãoRESUMO
Seven anthraquinones were isolated from aerial parts of Heterophyllaea lycioides (Rusby) Sandwith (Rubiaceae), including three derivatives that have not been described before: a hetero-bianthraquinone identified as (R)-2-hydroxymethyl-2'methyl-1,1',6,6'-tetrahydroxy-5,5' bianthraquinone (lycionine), and two mono-chlorinated derivatives related to soranjidiol. One of them is a homo-bianthraquinone: (R)-7-chloro-2,2'-dimethyl-1,1',6,6'-tetrahydroxy-5,5' bianthraquinone (7-chlorobisoranjidiol), whereas the second halogenated derivative corresponds to a monomeric structure: 5-chloro-1,6-dihydroxy-2-methyl anthraquinone (5-chlorosoranjidiol). The four known compounds were already isolated from another species of this genus, H. pustulata, and they were identified as 5,5'-bisoranjidiol, soranjidiol, pustuline and heterophylline. Structural elucidation was performed by means of an extensive spectroscopic analysis, including 1D and 2D NMR data as well as by HRMS analysis. Chemical structures of 7-chlorobisoranjidiol and 5-chlorosoranjidiol were confirmed by their synthesis from 5,5'-bisoranjidiol and soranjidiol, respectively. Type I photosensitizing properties (superoxide anion radical generation, O2-) were assessed by using the nitroblue tetrazolium assay. When lycionine and chlorinated derivatives were irradiated, they enhanced the O2- production with respect to the control; 7-chlorobisoranjidiol stood out by generating an increase of 20%, whereas the other anthraquinones only produced a slight increase of 7%.
Assuntos
Antraquinonas/química , Fármacos Fotossensibilizantes/química , Rubiaceae/química , Antraquinonas/isolamento & purificação , Estrutura Molecular , Fármacos Fotossensibilizantes/isolamento & purificação , Componentes Aéreos da Planta/químicaRESUMO
This study presents a method to evaluate three-dimensional strain in meniscal tissue using medical imaging. Strain is calculated by tracking small teflon markers implanted within the meniscal tissue using computed tomography imaging. The results are presented for strains in the middle and posterior third of the medial menisci of 10 human cadaveric knees, under simulated physiologically relevant loading. In the middle position, an average compressive strain of 3.4% was found in the medial-lateral direction, and average tensile strains of 1.4% and 3.5% were found in the anterior-posterior and superior-inferior directions respectively at 5° of knee flexion with an applied load of 1× body weight. In the posterior position, under the same conditions, average compressive strains of 2.2% and 6.3% were found in the medial-lateral and superior-inferior directions respectively, and an average tensile strain of 3.8% was found in the anterior-posterior direction. No statistically significant difference between strain in the middle or posterior of the meniscus or between the global strains is uncovered.