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

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Tomofumi Miyamoto
Misako Kashiwagi
Chiaki Tanaka
Ryo Yazaki


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


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