Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 14, Pages 7076-7088Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00945
Keywords
-
Categories
Funding
- Ministry of Education, Culture, Sports, Science, and Technology of Japan [22590029]
- Tokushima Bunri University for Education Reform and Collaborative Research [TBU2015-2-1, TBU2013-2-2]
- Grants-in-Aid for Scientific Research [26460028, 22590029, 15K08012, 24510293] Funding Source: KAKEN
Ask authors/readers for more resources
(-)-Talaumidin (1), a 2,5-biaryl-3,4-dimethyltetrahydrofuran lignan isolated from Aristolochia arcuata Masters, shows significant neurite-outgrowth promotion and neuroprotection in primary cultured rat cortical neurons and in NGF-differentiated PC12 cells. The four stereogenic centers on the tetrahydrofuran moiety in 1 result in the presence of seven diastereomers except for their enantiomers. In order to investigate the stereochemistry activity relationships of the stereoisomers, the systematic synthesis of all stereoisomers of 1 was accomplished by employing Evans aldol, diastereoselective hydroboration, reductive deoxygenation, and Mitsunobu reactions as key steps. The ability of all of the synthesized stereoisomers to promote neurite-outgrowth in PC12 and neuronal cells was evaluated. All stereoisomers exhibited moderate to potent neurotrophic activities in NGF-differentiated PC12 cells at 30 mu M and in primary cultured rat cortical neuronal cells at 0.01 mu M. In particular, le bearing all cis substituents resulted in the most potent neurite-outgrowth promotion.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available