7 0 0 0 OA わらびの究極発癌物質の合成およびDNAとの反応
- 著者
- 山田 静之 木越 英夫
- 出版者
- The Society of Synthetic Organic Chemistry, Japan
- 雑誌
- 有機合成化学協会誌 (ISSN:00379980)
- 巻号頁・発行日
- vol.53, no.1, pp.13-21, 1995-01-01 (Released:2009-11-16)
- 参考文献数
- 22
Synthetic studies on the bracken ultimate carcinogen (3) and its artificial analogues (32, 33) are described. The synthesis of (-) -ptaquilosin (2) the aglycon of a potent carcinogen ptaquiloside (1) from bracken and its (+) - enantiomer (ent- 2) was achieved starting with (+) -dimenthyl (1R, 2R) -cyclopentane-1, 2-dicarboxylate. Dehydration of ptaquilosin (2) under weakly basic conditions led to the ultimate carcinogen (3). DNA cleaving activities of both enantiomers (3) were compared, the one (3) derived from natural (-) -ptaquilosin (2) being more efficient. Reactivities of the ultimate carcinogen (3) toward DNA are described. DNA was shown to be alkylated at the particular sites of purine bases and to undergo cleavage. The molecular mechanism of DNA cleavage with the ultimate carcinogen (3) was disclosed using deoxytetranucleotide d (GTAC) as a model DNA substrate.
2 0 0 0 OA 2 わらびの新規ノルセスキテルペン配糖体,Ptaquilosideの単離と構造
- 著者
- 広野 巌 大場 茂 斉藤 喜彦 丹羽 治樹 小鹿 一 若松 一雅 山田 静之 松下 和弘
- 出版者
- 天然有機化合物討論会
- 雑誌
- 天然有機化合物討論会講演要旨集
- 巻号頁・発行日
- no.26, pp.9-15, 1983-09-15
We have examined the constituents of bracken fern, Pteridium aquilinum var. latiusculum and performed fractionation of the boiling water extracts by means of the assay based on carcinogenicity to rats. From the fraction exhibiting carcinogenicity, we have isolated an unstable norsesquiterpene glucoside of illudane type named ptaquiloside (1). The planar structure of (1) has been established on the basis of spectral and chemical means. The carcinogenicity of (1) to rats is currently under investigation.