Tanaka Reiko, Nakata Tomoko, Yamaguchi Chiharu, Wada Shun-Ichi, Yamada Takeshi, Tokuda Harukuni
Department of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, Takatsuki, Osaka, Japan.
Planta Med. 2008 Mar;74(4):413-6. doi: 10.1055/s-2008-1034347.
Four known friedelane-type triterpenoids, friedelin ( 1), 3-hydroxy-D:A-friedoolean-3-en-2-one ( 2), 2beta-hydroxy-D:A-friedooleanan-3-one ( 3), and 3alpha-hydroxy-D:A-friedooleanan-2-one ( 4), and two known lupane-type triterpenoids, lupeol ( 5) and betulin ( 6), were isolated from the stem bark of Mallotus philippensis. Isolates 1 - 4 and their synthetic analogues, 3-acetoxy-D:A-friedoolean-3-en-2-one ( 2A) and 3alpha-acetoxy-D:A-friedooleanan-2-one ( 4A), were tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12- O-tetradecanoylphorbol 13-acetate (TPA). The inhibitory effect of compounds 2 (IC (50) = 292 mol ratio/32 pmol/TPA) and 4 (IC (50) = 288) was stronger than those of the other compounds tested and the positive control, curcumin (IC (50) = 343). Compound 4 strongly inhibited mouse skin tumor promotion in an IN VIVO two-stage carcinogenesis model. Studies have been conducted to identify the biologically active compounds extracted from the leaves, bark, and cones of trees that currently have no specific commercial use and are therefore treated as waste in the forestry industry.
从菲律宾野桐的茎皮中分离出4种已知的木栓烷型三萜类化合物，即木栓酮（1）、3-羟基-D:A-呋甾-3-烯-2-酮（2）、2β-羟基-D:A-呋甾烷-3-酮（3）和3α-羟基-D:A-呋甾烷-2-酮（4），以及2种已知的羽扇豆烷型三萜类化合物，即羽扇豆醇（5）和桦木醇（6）。对分离物1 - 4及其合成类似物3-乙酰氧基-D:A-呋甾-3-烯-2-酮（2A）和3α-乙酰氧基-D:A-呋甾烷-2-酮（4A）进行了测试，考察它们对12-O-十四烷酰佛波醇-13-乙酸酯（TPA）诱导的爱泼斯坦-巴尔病毒早期抗原（EBV-EA）激活的抑制作用。化合物2（IC（50）= 292摩尔比/32皮摩尔/TPA）和4（IC（50）= 288）的抑制作用强于所测试的其他化合物以及阳性对照姜黄素（IC（50）= 343）。在体内两阶段致癌模型中，化合物4强烈抑制小鼠皮肤肿瘤的促进作用。人们开展了研究，以鉴定从目前没有特定商业用途、因此在林业行业中被视为废物的树木的叶子、树皮和球果中提取的生物活性化合物。
