Enantioselective syntheses of both enantiomers of 9′-dehydroxyimperanene and 7, 8-dihydro-9′-dehydroxyimperanene and the comparison of biological activity between 9-norlignans and dihydroguaiaretic acids. Issue 13 (1st July 2016)

• Record Type: Journal Article
• Authors: Yamauchi, Satoshi; Tanimura, Ryosuke; Nishiwaki, Hisashi; Nishi, Kosuke; Sugahara, Takuya; Maruyama, Masafumi; Ano, Yoshitaka; Akiyama, Koichi; Kishida, Taro
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 26:Issue 13(2016)
• Page Start: 3019
• Page End: 3023
• Publication Date: 2016-07-01
• Subjects: Lignan -- Norlignan -- Imperanene; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2016.05.020
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: To estimate the effect of methyl group of dihydroguaiaretic acid, which shows many kinds of biological activities, on biological activity, both enantiomers of 9′-dehydroxyimperanene (5, 6 ) and 7, 8-dihydro-9′-dehydroxyimperanene (7, 8 ) lacking one of the methyl groups of dihydroguaiaretic acid were synthesized. ( S )-7, 8-Dihydro-9′-dehydroxyimperanene (7 ) showed 4–6-fold higher cytotoxic activity than all stereoisomers of dihydroguaiaretic acid (2 –4 ). The IC50 values of ( S )-7, 8-dihydro-9′-dehydroxyimperanene (7 ) against HL-60 and HeLa cells were 6.1 μM and 5.6 μM, respectively. Though only one of three stereoisomers of dihydroguaiaretic acid showed antibacterial activity against a gram negative bacterium, both enantiomers of5 –8 showed antibacterial activity against a gram negative bacterium. This is a Letter on biological activity of 9-norlignan, in which one of methyl groups of lignan is absent.