Chemistry of phenolic compounds of licorice (Glycyrrhiza species)
and their estrogenic and cytotoxic activities*
Taro Nomura1, Toshio Fukai1,**, and Toshiyuki
Akiyama2
1School of Pharmaceutical Sciences, Toho University,
2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan; 2Exploratory Chemistry
Research Laboratories, Sankyo Co., Ltd., 2-58 Hiromachi 1-Chome, Shinagawa-ku,
Tokyo 140-8710, Japan
Abstract: The genus Glycyrrhiza consists of
about 30 species in which G. glabra, G. uralensis, G.
inflata, G. aspera, G. korshinskyi, and G. eurycarpa
are generally recognized as licorice because of their sweet taste. Except
G. korshinskyi, we examined isoprenoid-substituted phenols of
these licorices. Each plant could be characterized by some isoprenoid
phenols. We also investigated the biological activities of the Glycyrrhiza
phenols. In the course of screening phytoestrogen in medicinal plants,
six Glycyrrhiza phenols exhibited the binding affinities for the bovine
uterine estrogen receptor. The affinity of a dihydrostilbene with two
3-methyl-2-butenyl (prenyl) groups, gancaonin R, was higher than those
of isoflavone phytoestrogens (genistein and daidzein) in dietary foods.
The affinities of the other five phenols, a flavanone (liquiritigenin),
two prenylflavanones (isobavachin and sigmoidin B), a prenylated coumestan
(glycyrol), and a pyranoisoflav-3-ene (glabrene), were similar to that
of the dietary isoflavone, genistein or daidzein. Cytotoxic activities
of the Glycyrrhiza phenols against human oral tumor cell lines
and HIV-infected MT-4 cells were also reviewed.
* A special topic issue on the
science of sweeteners.
** Corresponding author. E-mail: [email protected]
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