Anti-tumor promoting diterpenes from the stem bark of Thuja standishii (Cupressaceae)
Anti-tumor promoting diterpenes from the stem bark of Thuja standishii (Cupressaceae)
复制标题
DOI：
10.1016/s0968-0896(01)00099-2
复制
发表时间：
2001-07-01
影响因子：
3.5
通讯作者：
Tanaka, R
中科院分区：
文献类型：
--
作者：
Iwamoto, M;Ohtsu, H;Tanaka, R
三种新的拉丹烷型二萜化合物：labda-8(17),13-dien-15,12R-olid-19-oic Acid (1), 12S-羟基labda-8(17),13(16), 14-trien-19-oic Acid (2) 和 13-ethoxylabda-8(17),11,14-trien-19-oic Acid (3) 与已知的 二萜类化合物。从崖柏的茎皮中分离出 trans-communic Acid (4)、totarol (5)、12-methoxyabieta-8,11,13-trien-11-ol (6) 和 7 alpha ,8 alpha -epoxy-6 alpha -Hydroxyabieta-9(11),13-dien-12-one(7)。通过光谱方法和化学转化确定了13个化合物的结构。测试了这些化合物与 Standishinal (8)、12-羟基-6,7-seco-abieta-8,11,13-trien-6,7-dial (9) 和 6 α-羟基sugiol (10) 一起对 12-O-十四烷酰佛波醇-13-乙酸酯诱导的 Epstein-Barr 病毒早期抗原 (EBV-EA) 激活的抑制作用 （TPA），作为潜在癌症化学预防剂的测试。化合物10对EBV-EA诱导表现出强烈的抑制作用（1000摩尔比时抑制100%；TPA）。化合物2和6对EBV-EA诱导表现出中等程度的抑制作用。此外，在使用 7,12-二甲基苯并[a]蒽和 TPA 的两阶段小鼠皮肤癌发生试验中，发现 15-oxolabda-8(17),11Z,13E-trien-19-oic Acid (11) 表现出抗肿瘤促进活性。 (C) 2001 Elsevier Science Ltd. 保留所有权利。
Three new labdane-type diterpenoids, labda-8(17),13-dien-15,12R-olid-19-oic acid (1), 12S-hydroxylabda-8(17),13(16), 14-trien-19-oic acid (2) and 13-ethoxylabda-8(17),11,14-trien-19-oic acid (3), along with known dilerpenoids. trans-communic acid (4), totarol (5), 12-methoxyabieta-8,11,13-trien-11-ol (6), and 7 alpha ,8 alpha -epoxy-6 alpha -hydroxyabieta-9(11),13-dien-12-one(7) were isolated from the stem bark of Thuja standishii. The structures of 13 were established by spectroscopic methods and chemical conversion. These compounds together with standishinal (8), 12-hydroxy-6,7-seco-abieta-8,11,13-trien-6,7-dial (9) and 6 alpha -hydroxysugiol (10) were tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA), as a test for potential cancer chemopreventive agents. Compound 10 showed strong inhibitory effect on EBV-EA induction (100% inhibition at 1000 mol ratio;TPA). and compounds 2 and 6 showed moderate inhibitory effects on EBV-EA induction. In addition, 15-oxolabda-8(17),11Z,13E-trien-19-oic acid (11) was found to exhibit the antitumor promoting activity in two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene and TPA. (C) 2001 Elsevier Science Ltd. All rights reserved.