RESUMEN
The chemical investigation of Homotrigona apicalis propolis collected in Binh Dinh province, Vietnam, led to the isolation of nine compounds, including four sesquiterpenes: spathulenol (1), 1αH,5ßH-aromandendrane-4ß,10α-diol (2), 1ß,6α-dihydroxy-4(15)-eudesmene (3), and 1ßH,5ßH-aromandendrane-4α,10ß-diol (4); three triterpenes: acetyl oleanolic acid (5), 3α-hydroxytirucalla-8,24-dien-21-oic acid (6), and ursolic acid (7); and two xanthones: cochinchinone A (8) and α-mangostin (9). Sesquiterpens 1-4 and triterpene 6 were isolated for the first time from stingless bee propolis. Plants in the Cratoxylum and Aglaia genus were suggested as resin sources of the propolis sample. In the antibacterial activity evaluation, the EtOH extract only showed moderate activity on S. aureus, while the isolated compounds 7-9 showed good antibacterial activity, with IC50 values of 0.56 to 17.33 µg/mL. The EtOH extract displayed selective cytotoxicity against the A-549 cancer cell line, with IC50 values of 22.82 ± 0.86 µg/mL, and the xanthones 8 and 9 exhibited good activity against the KB, HepG-2, and A-549 cancer cell lines, with IC50 values ranging from 7.55 ± 0.25 µg/mL to 29.27 ± 2.07 µg/mL. The cytotoxic effects of xanthones 8 and 9 were determined by the inhibition of the EGFR and HER2 pathways using a molecular docking study. Compounds 8 and 9 displayed strong binding affinity with EFGR and HER2, with values of -9.3 to -9.9 kcal/mol. Compounds 5, 8, and 9 showed potential α-glucosidase inhibitory activities, which were further confirmed by computational studies. The binding energies of compounds 5, 8, and 9 were lower than that of arcabose.
RESUMEN
Methionine (MET) is combined with paracetamol (PAR) in a pain relief soft capsule in order to prevent the haematologic damage of paracetamol. A hydrophillic liquid chromatographic (HILIC) method was developed for simultaneous determination of PAR and MET in the combined formulation. Various analytical conditions were investigated, and the final method was chosen using silica column (150 × 4,6 mm; 5 µm), mobile phase of acetonitrile - aqueous solution of 10 mM formic acid 5 mM diethylamine (60:40, v/v), UV detection at 254 nm for PAR and 210 nm for MET. The method was validated according to ICH guidelines in terms of selectivity, linearity, accuracy, precision and robustness. The method was successfully applied for quantitation of both compounds in soft capsule preparations bought from the market. Notably, in this study, a novel approach was proposed to improve peak shape of amino acid - a problem often observed in HILIC. The addition of diethylamine to mobile phase shortened the retention time of MET and significantly improved peak shape on both silica and cyano columns, due to electrostatic interaction competition and silanol end-capping effect. The result of this research demonstrated the advantages of HILIC in simultaneous analysis of a polar compound amino acid, especially in combination with a less polar substance. The use of diethylamine as a mobile phase modifier to enhance peak shape is a new suggestion that can be used in further studies on amino acid analysis by HILIC.