Anticoagulation and Anticancer Constituents fromEugenia caryophyllata Thunb
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초록
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), 3β-hydroxyolean-12-en-28-oic acid (oleanolic acid, 3) and 2α,3β-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 IC50 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 ± 11.2 seconds as compared to the control with the value of 37.5 ± 2.2 seconds at the concentration of 50㎍/㎖. Compounds 1 and 3 revealed inhibitory activity on farnesyl protein transferase (FPTase) with the IC50 values of 0.49 and 0.24 mM and compounds 1 and 2 highly inhibited the growth of rat-H-ras cells with the GI50 values of 6.63 and 5.70 μM, respectively.
Abstract
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), 3β-hydroxyolean-12-en-28-oic acid (oleanolic acid, 3) and 2α,3β-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 IC50 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 ± 11.2 seconds as compared to the control with the value of 37.5 ± 2.2 seconds at the concentration of 50㎍/㎖. Compounds 1 and 3 revealed inhibitory activity on farnesyl protein transferase (FPTase) with the IC50 values of 0.49 and 0.24 mM and compounds 1 and 2 highly inhibited the growth of rat-H-ras cells with the GI50 values of 6.63 and 5.70 μM, respectively.
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