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从鱼鳞云杉茎皮中分离得到的两种新型抗肿瘤促癌作用的锯齿烷型三萜类化合物。

Two new anti-tumor promoting serratane-type triterpenoids from the stem bark of Picea jezoensis var. jezoensis.

作者信息

Tanaka Reiko, Ishikawa Yohei, Minami Toshifumi, Minoura Katsuhiko, Tokuda Harukuni, Matsunaga Shunyo

机构信息

Department of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, Osaka, Japan.

出版信息

Planta Med. 2003 Nov;69(11):1041-7. doi: 10.1055/s-2003-45153.

Abstract

Two new serratane-type triterpenoids, 1 and 2, were isolated from the stem bark of Picea jezoensis Carr. var. jezoensis (Pinaceae). Their structures were determined to be 3beta-methoxyserrat-13-en-21beta-ol (1) and 13beta, l4beta-epoxy-3beta-methoxyserratan-21beta-ol (2) on the basis of spectroscopic methods and partial syntheses. Compounds 1 and 2 and their acetates were screened as potential anti-tumor promoters by using the in vitro short-term 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation assay. IC50 value evaluation showed that compound 1 was more effective than others. In addition, compounds 1 and 2 were examined for anti-tumor promoting activities in a two-stage carcinogenesis assay of mouse skin tumors induced by 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. Compounds 1 and 2 exhibited significant anti-tumor promoting effects on mouse skin carcinogenesis.

摘要

从鱼鳞云杉(松科)的茎皮中分离出两种新的锯齿烷型三萜化合物1和2。通过光谱方法和部分合成确定它们的结构分别为3β-甲氧基锯齿-13-烯-21β-醇(1)和13β,14β-环氧-3β-甲氧基锯齿烷-21β-醇(2)。通过体外短期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)激活试验,对化合物1和2及其乙酸酯作为潜在的抗肿瘤促进剂进行了筛选。IC50值评估表明化合物1比其他化合物更有效。此外,在以7,12-二甲基苯并[a]蒽(DMBA)为引发剂、TPA为促进剂诱导的小鼠皮肤肿瘤两阶段致癌试验中,对化合物1和2的抗肿瘤促进活性进行了检测。化合物1和2对小鼠皮肤致癌作用表现出显著的抗肿瘤促进作用。

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