Anticoagulation and Anticancer Constituents from Eugenia caryophyllata Thunb

From the EtOAc fraction of Eugenia caryophyllata, four compounds were isolated through activity-guided silica gel column chromatography, From the result of spectroscopic data including NMR, MS and IR, the chemical structures of the compounds were determined as 1-allyl-4-hydroxy-3-methoxybezene acetate (eugenol acetate, 1), 1-allyl-4-hydroxy-3-methoxybezene (eugenol, 2), $3{\beta}-hydroxyolean-12-en-28-oic$ acid (oleanolic acid, 3) and $2{\alpha}$, $3{\beta}-dihydroxyolean-12-en-28-oic$ acid (maslinic acid, 4). Compounds 3 and 4 were isolated for the first time from this plant. Also, compounds 1, 2 and 3 exhibited relatively high platelet aggregation inhibitory activity with the $IC_{50}$ values of 0.24, 0.09 and 0.07 mM, respectively. Compound 2 significantly prolonged activated partial thromboplastin time (aPTT) with the value of $124{\pm}11.2$ seconds as compared to the control with the value of $37.5{\pm}2.2$ seconds at the concentration of 50 ${\mu}g/ml$. Compounds 1 and 3 revealed inhibitory activity on farnesyl protein transferase (FPTase) with the $IC_{50}$ values of 0.49 and 0.24 mM and compounds 1 and 2 highly inhibited the growth of rat-H-ras cells with the $Gl_{50}$ values of 6.63 and 5.70 ${\mu}M$, respectively.