Stereochemistry of cis- and trans-Hinokiresinol and Their Estrogen-like Activity

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概要

• 論文の詳細を見る

• Naturally occurring phenylpropanoids, hinokiresinol (trans-hinokiresinol) and nyasol (cis-hinokiresinol) were found to possess appreciable estrogen receptor binding activity. Strong differences in activity were observed between the geometrical isomers and enantiomers. Among these, (3S)-cis-hinokiresinol displayed the highest activity, one order of magnitude greater than the activity of genistein. Furthermore, cis- and trans-hinokiresinol stimulated the proliferation of estrogen-dependent T47D breast cancer cells, and their stimulatory effects were blocked by an estrogen antagonist, indicating that the compounds are estrogen agonists. In addition, the absolute configuration of C-3 in (+)-cis-hinokiresinol has been assigned as S by comparison with the circular dichroism spectra of the hydrogenated products prepared from cis and trans ((3S)-trans-hinokiresinol : previously assigned) isomers. These results incidentally provide us with an unambiguous answer to contradictory reports regarding the assignment of the full stereochemisry of cis-and trans-hinokiresinol that have existed in the literature for more than two decades.

• 公益社団法人日本薬学会の論文
• 2000-03-01

著者

• AKIYAMA Toshihiko

  Faculty of Pharmaceutical Sciences, Okayama University

• Akimura T

  Department Of Neurosurgery Yamaguchi University School Of Medicine

• Akiyama T

  Faculty Of Pharmaceutical Sciences Okayama University

• Tsutsumi Shinya

  Bioengineering Research Group I Process Technology Research Laboratories Daiichi Sankyo Co. Ltd.

• MINAMI Emiko

  Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd.,

• TAKI Motohiko

  Pharmacology and Molecular Biology Research Laboratories, Sankyo Co., Ltd.,

• TAKAISHI Sachiko

  Pharmacology and Molecular Biology Research Laboratories, Sankyo Co., Ltd.,

• IIJIMA Yasuteru

  Pharmacology and Molecular Biology Research Laboratories, Sankyo Co., Ltd.,

• TSUTSUMI Shinya

  Analytical and Metabolic Research Laboratories Sankyo Co., Ltd.,

• AKIYAMA Toshiyuki

  Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd.,

• Taki M

  Pharmacology And Molecular Biology Research Laboratories Sankyo Co. Ltd.

• Iijima Y

  Pharmacology And Molecular Biology Research Laboratories Sankyo Co. Ltd.

• Iijima Yasuteru

  Pharmacology And Molecular Biology Research Laboratories Sankyo Co. Ltd.

• Minami Emiko

  Exploratory Chemistry Research Laboratories Sankyo Co. Ltd.

• Takaishi S

  Pharmacology And Molecular Biology Research Laboratories Sankyo Co. Ltd.

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