RESUMEN
Teaghrelins, identified originally in Chin-shin oolong tea, are unique acylated flavonoid tetraglycosides and proposed to be potential oral analogues of ghrelin. In the present study, two new teaghrelin-like compounds were characterized from tea cultivars (TTES No. 12), and their chemical structures were established by the spectroscopic and spectrometric analysis. However, due to the different location of rhamnose, these two teaghrelin-like compounds may not show significant ghrelin receptor affinity.[Figure: see text].
Asunto(s)
Camellia sinensis/química , Flavonoides/química , Acilación , Flavonoides/metabolismo , Ghrelina/química , Ghrelina/farmacología , Espectroscopía de Resonancia Magnética , Simulación del Acoplamiento Molecular , Estructura Molecular , Extractos Vegetales/química , Receptores de Ghrelina/metabolismo , Espectrometría de Masa por Ionización de Electrospray , Té/químicaRESUMEN
Teaghrelins are unique acylated flavonoid tetraglycosides originally identified in Chin-shin oolong tea, and proposed to be potential oral analogs of ghrelin. Two acylated flavonoid tetraglycosides were isolated from Shy-jih-chuen oolong tea, and their chemical structures were determined to be quercetin and kaempferol 3-O-[α-L-arabinopyranosyl(1 â 3)][2"-O-(E)-p-coumaroyl] [ß-D-glucopyranosyl(1 â 3)-α-L-rhamnopyranosyl(1 â 6)]-ß-D-glucoside. These two compounds were extremely similar to the two teaghrelins (teaghrelin-1 and teaghrelin-2) in Chin-shin oolong tea by simply replacing a glucopyranosyl group with an arabinopyranosyl group. Molecular modeling showed that the two putative teaghrelins identified in Shy-jih-chuen docked to and interacted with the ghrelin receptor as well as teaghrelin-1 and teaghrelin-2. Mixture of these two putative teaghrelins was shown to enhance the release of growth hormone from primary anterior pituitary cells of rats. The results suggest that two teaghrelins, named teaghrelin-3 and teaghrelin-4, are present in Shy-jih-chuen oolong tea and possess biological activities analogous to teaghrelins in Chin-shin oolong tea. PRACTICAL APPLICATIONS: According to this study, teaghrelin-3 and teaghrelin-4 may be regarded as active ingredients for the quality control of Shy-jih-chuen oolong tea. The content of teaghrelins may serve as a key factor for the farmers to select new tea plants in their next propagation of Shy-jih-chuen cultivar. Crude water extract of Shy-jih-chuen oolong tea containing teaghrelins is considered to be an adequate food supplement or additive in functional food products.