Isolation, Structure, Synthesis and the Biological Activity of the Novel Nor-lignans from Anemarrhenae Rhizoma

Main Article Content

Tomofumi Miyamoto
Misako Kashiwagi
Chiaki Tanaka
Ryo Yazaki

Abstract

Introduction: Anemarrhena Rhizoma is a dried rhizome of Anemarrehena asphodeloides
Bunge. Nyasol (cis-hinokiresinol) is a major nor-lignan constituent of this crude drug, which shows
estrogenic, hyaluronidase inhibitory, and anti-angiogenic activities. In this paper, we report on the
isolation, structure elucidation, synthetic study, and the biological activities of novel nor-lignans
isolated from A. Rhizoma. Method: A. Rhizoma (1kg) was extracted with CHCl3, and the CHCl3 extract
was subjected to Silica gel C.C., reversed phase C.C, GPC recycle HPLC, and RP-HPLC to give two
novel nor-lignans (3’’-hydroxy-4’’-O-methyl nyasol, 3’-hydroxy-4’-O-methyl nyasol) together with three
known lignans (nyasol, 4’’-O-methyl nyasol, 3’-methoxy nyasol).The novel nor-lignan was synthesized
using 4-hydroxybenzaldehyde and 2-methoxyphenol as starting materials. Totally, ten derivatives were
prepared and evaluated the effect on the proliferation of HeLa and the anti-estrogenic activity against
MCF-7 cell lines. Results: The novel nor-lignans showed the growth inhibition against HeLa at 70
times higher than that of nyasol. On the other hand, nyasol showed estrogenic activity, while, the
novel nor-lignan showed the anti-estrogenic activity, and the effect was ten times higher than that of
Tamoxifen. Conclusion: The novel nor-lignans may be useful for
the development of new hormonal therapeutic agents against
breast cancer.PCT Int. Appl. (2014), WO 2014136786 A1 20140
912

Downloads

Download data is not yet available.

Article Details

Section
Invited Speaker