Chemical and Pharmaceutical Bulletin p. 34 - 40 (1996)
Update date:2022-08-04
Topics:
Tanaka, Takashi
Kouno, Isao
Nonaka, Gen-Ichiro
Geraniin (1), a widely distributed ellagitannin having a dehydrohexahydroxydiphenoyl (DHHDP) ester moiety, was converted into chebulagic acid (2), an ellagitannin having a chebuloyl ester moiety, which was reported to be a potent inhibitor of DNA topoisomerases. This was achieved by addition of the thiol group of glutathione to the six-membered acetal ring form of the DHHDP moiety (1a) with concomitant hydrolytic ring cleavage and subsequent reductive desulfurization with Raney nickel. The concurrent addition of the thiol to the five-membered acetal ring form of the DHHDP group (1b) generated the product 14 and its precursor 13, which are structurally related to naturally occurring ellagitannins isolated from Euphorbiaceous plants. Thus, the rearrangements observed in these reactions may be relevant to the metabolism of DHHDP esters in plants.
View MoreJinan Jinguilin Chemical Co.,Ltd
Contact:+86-531-81188412
Address:3rd floor of Torch Building, Huanyuan Rd, City of Jinan
Contact:+49-9398-993127
Address:Untertorstr. 27
Yingkou Sanzheng Organic Chemical Co. Ltd.
Contact:+86-417-3638818
Address:25 Gengxinli Village, Daqing Road, Yingkou, Liaoning, China
Shanghai Sinofluoro Scientific Co., Ltd
Contact:+86-21-64279360
Address:Room 1006,Building 3,#58 East Xinjian Road, Shanghai ,201100,China,
Shanghai Xinda Pharmaceuticals Co., Ltd.
Contact:86-21-33692333-8008
Address:999 Linxian Road, Jinshan Industrial Park, Shanghai, China
Doi:10.1021/ic050663n
(2005)Doi:10.1039/P29840000209
(1984)Doi:10.1016/S0040-4020(00)00478-6
(2000)Doi:10.1016/S0022-3697(96)00066-2
(1996)Doi:10.1021/om990159o
(1999)Doi:10.1021/om990331o
(1999)
