2. Academic Validation
  3. 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

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

  • Bioorg Med Chem Lett. 2016 Jul 1;26(13):3019-3023. doi: 10.1016/j.bmcl.2016.05.020.
Satoshi Yamauchi 1,  Ryosuke Tanimura 2,  Hisashi Nishiwaki 2,  Kosuke Nishi 2,  Takuya Sugahara 3,  Masafumi Maruyama 2,  Yoshitaka Ano 2,  Koichi Akiyama 4,  Taro Kishida 3
Affiliations

Affiliations

  • 1 Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan; South Ehime Fisheries Research Center, 1289-1 Funakoshi, Ainan, Ehime 798-4292, Japan. Electronic address: syamauch@agr.ehime-u.ac.jp.
  • 2 Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
  • 3 Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan; South Ehime Fisheries Research Center, 1289-1 Funakoshi, Ainan, Ehime 798-4292, Japan.
  • 4 Advanced Research Support Center (ADRES), Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
PMID: 27210431 DOI: 10.1016/j.bmcl.2016.05.020
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 6.1μM and 5.6μM, respectively. Though only one of three stereoisomers of dihydroguaiaretic acid showed Antibacterial activity against a gram negative bacterium, both enantiomers of 5-8 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.

Keywords

Imperanene; Lignan; Norlignan.

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