Stereochemistry of cis- and trans-hinokiresinol and their estrogen-like activity.

Abstract

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.

• Authors: E Minami, M Taki, S Takaishi, Y Iijima, S Tsutsumi, T Akiyama
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 48 Issue 3 Pg. 389-92 (Mar 2000) ISSN: 0009-2363 [Print] Japan
• PMID: 10726863 (Publication Type: Journal Article)

Chemical References

• Estrogen Antagonists
• Estrogens, Non-Steroidal
• Isoflavones
• Lignans
• Phenols
• Phytoestrogens
• Plant Preparations
• Polyunsaturated Alkamides
• hinokiresinol
• Estradiol
• ICI 164384

Topics

• Animals
• Cattle
• Cell Division (drug effects)
• Estradiol (analogs & derivatives, pharmacology)
• Estrogen Antagonists (pharmacology)
• Estrogens, Non-Steroidal (chemistry, pharmacology)
• Female
• Humans
• In Vitro Techniques
• Isoflavones
• Lignans
• Magnetic Resonance Spectroscopy
• Phenols (chemistry, pharmacology)
• Phytoestrogens
• Plant Preparations
• Plants, Medicinal (chemistry)
• Polyunsaturated Alkamides
• Stereoisomerism
• Tumor Cells, Cultured
• Uterus (drug effects, metabolism)