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 Morewebsite:https://www.synose.com/
Contact:86-579-82275537
Address:No.1958 Liyu Road , jinhua,zhejiang,China
Shanghai Rainbow Chemistry Co., Ltd.
Contact:+86-21-64968086-5815/5812
Address:3rd floor, Building 7, 251 Faladi Road, Zhangjiang Hi-Tech Park, Pudong District, Shanghai, P.R. China
Shantou Baokang Pharmaceutical Co., Ltd.
Contact:+86-754-88873487
Address:5/F B Block Huangshan Bldg Huangshan Rd Shantou
Chengda Pharmaceuticals Co., Ltd.
Contact:+86-573-84601188
Address:hengshan Road 5# in Jiashan, zhejiang
Hangzhou Sartort Biopharma Co., Ltd
website:http://www.sartort.com
Contact:86-571-87039693
Address:No. 57, Tech Park Road, Hangzhou, Zhejiang, 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)
