천연미백소재를 개발하기 위하여 대산(마늘)을 포함한 총 10종의 약용식물 혼합물을 발효하여 얻은 발효물로부터 tyrosinase inhibition 활성을 확인하고, 이로부터 신규한 화합물 1종 외 3종의 활성 성분을 분리하였다. 마늘복합발효물의 영양성분 13항목을 분석하여 기능성 식품 소재로의 활용가능성을 확인하였다. 발효원액의 tyrosinase 저해효과는 88.6%로 나타났고, 활성성분의 분리를 위하여 EtOAc, n-BuOH 및 H2O로 분배, 추출하였다. 이중 수득률이 가장 높은 EtOAc 분획물(47g)로부터 silica gel 및 ODS column chromatography를 반복하면서 TLC 와 효소저해 효과로부터 확인한 활성분획을 순차적으로 분리하였다. 화합물의 화학구조를 NMR 및 MS 등의 스펙트럼으로 분 석한 결과 phenylpropanoid류의 신규 화합물인 2,4,5- trihydroxy-benzenepropanoic acid (1) (1.9 ㎎) 및 화합물 1과 동량으로 혼재하는 2,3,5-trihydroxy-benzenepropanoic acid (2)를 확인하였다. 이외에 2,4-dihydroxy-hydrocinnamic acid (3) (3.3 ㎎) 및 (+)sesamin (4) (6.1 ㎎)을 분리·동정하였다. 이 화합물들이 향후 본 조성물의 지표성분 및 기능성 성분으로 활 용된다면 기업에서의 원천기술 확보를 통한 제품개발과 산업화에 매우 유용할 것으로 사료된다.
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 μg/ml. 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 Gl50 values of 6.63 and 5.70 μm, respectively.
Three stigmastane-type sterols and one ergostane-type sterol were isolated from the ethyl acetate soluble fraction of the aerial parts of Artemisia princeps Pampanini (Sajuarissuk). From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as stigmasta-5,22-dien-3,β-ol (stigmasterol, 1),stigmast-5-en-3β-ol(β-sitosterol,2), 5β,8β-epidioxy-5β,8β-ergosta-6,22-dien-3β-ol(ergosterol peroxide, 3), and β-sitosterol 3-O-βD-glucopyranoside(daucosterol,4).
The flowers of Chrysanthemum boreale Makino were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with n-hexane, EtOAc, n-BuOH and H2O. Two compounds from the n-hexane fraction and one glucoside from the n-BuOH fraction were isolated through the repeated silica gel and ODS column chromatographies. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as β-sitosterol (1), phytol (2) and zingerone 4-O-β-D-glucopyranoside (3). Compounds 2 and 3 were isolated for the first time from this plant.