Prenylflavonoids: A New Class of Non-Steroidal Phytoestrogen (Part 2). Estrogenic Effects of 18-Isopentenylnaringenin on Bone Metabolism

Miyamoto, Mitsuhiro; Matsushita, Yasuhiro; Kiyokawa, A; Fukuda, Chie; Iijima, Yasuteru; Sugano, Mamoru; Akiyama, Tsuyoshi

doi:10.1055/s-2006-957505

Cited by 63 publications

(43 citation statements)

References 7 publications

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“…Oral administration of compound 1 or 9 caused estrogenic effects in OVX SD rats by increasing their uterine weight, which was evaluated in OVX rats according to the method reported by Miyamoto et al 25) In contrast to the case of in vitro assays, compound 9 was more effective than genistein (1), which was reported to be converted to dihydrogenistein with less potent estrogenic activity by human intestinal microflora in the gastrointestinal tract. 26,27) However, compound 9 may be more resistant to degradation by intestinal bacteria due to the presence of a bulky 1,1-dimethylallyl group at C-8 in the A ring of the isoflavone skeleton, which may account for the more potent estrogenic activity of 9 in the in vivo experiment.…”

Section: Discussionmentioning

confidence: 99%

Estrogenic and Antiestrogenic Activities of the Roots of Moghania philippinensis and Their Constituents

Ahn

Nakamura

Akao

et al. 2004

Biological & Pharmaceutical Bulletin

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In the course of our search for natural estrogenic compounds from medicinal plants, we found that the methanolic extract from the roots of Moghania philippinensis (Fabaceae) showed significant effects on the proliferation of MCF-7 cells (human breast cancer) and induction of b b-galactosidase activity in a yeast two-hybrid assay. Through estrogenic activity-guided fractionation, we isolated several active flavonoids including prenylated ones. The CHCl 3 fraction and its new constituent, 8-(1,1-dimethylallyl)genistein (9), appreciably increased the uterine weight in ovariectomized rats when administered orally for 14 consecutive days, in which compound 9 showed stronger estrogenic activity than genistein. Antiestrogenic activities were also examined based on the inhibition of MCF-7 cell proliferation and b b-galactosidase activity in the yeast two-hybrid assay, mediated by 17b bestradiol. 5,7,3,4-Tetrahydroxy-6,8-diprenylisoflavone (6) showed the strongest antiestrogenic activity.

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Section: Discussionmentioning

confidence: 99%

Estrogenic and Antiestrogenic Activities of the Roots of Moghania philippinensis and Their Constituents

Ahn

Nakamura

Akao

et al. 2004

Biological & Pharmaceutical Bulletin

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“…For example, it inhibits the growth of human breast cancer cells in vitro, inhibits bone loss in ovariectomized mice (138), and inhibits the CYP1A2 cytochrome P450 involved in procarcinogen activation (73). It binds similarly to both ERα and ERβ, and its estrogenic activity in vitro is greater than that of genistein, daidzein, or coumestrol.…”

Section: Potential Health Beneficial Effectsmentioning

confidence: 99%

Phytoestrogens

Dixon

2004

Annu. Rev. Plant Biol.

442

319

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▪ Abstract Collectively, plants contain several different families of natural products among which are compounds with weak estrogenic or antiestrogenic activity toward mammals. These compounds, termed phytoestrogens, include certain isoflavonoids, flavonoids, stilbenes, and lignans. The best-studied dietary phytoestrogens are the soy isoflavones and the flaxseed lignans. Their perceived health beneficial properties extend beyond hormone-dependent breast and prostate cancers and osteoporosis to include cognitive function, cardiovascular disease, immunity and inflammation, and reproduction and fertility. In the future, metabolic engineering of plants could generate novel and exquisitely controlled dietary sources with which to better assess the potential health beneficial effects of phytoestrogens.

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“…8-Prenylnaringenin (PN) is one of the most abundant prenylflavonoids in beer and has been reported to be a potent phyto-oestrogen in vitro (Stevens & Page, 2004). In a rat model 8-PN has been shown to inhibit ovariectomyinduced loss of BMD in the proximal tibia and suppress urinary excretion of the bone markers hydroxyproline, pyridinoline and deoxypyridinoline (Miyamoto et al 1998). 8-PN increases alkaline phosphatase activity in vitro in normal human fetal osteoblasts (0 .…”

Section: Prenylated Flavonoidsmentioning

confidence: 99%

Moderate alcohol consumption and increased bone mineral density: potential ethanol and non-ethanol mechanisms

et al. 2006

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Mounting epidemiological evidence indicates an association between the moderate ingestion of alcoholic beverages and higher bone mineral density (v. abstainers). More limited findings provide some evidence for translation of this association into reduced fracture risk, but further studies are required. Here, these data are reviewed and caveats in their assimilation, comparison and interpretation as well as in the use and application of bone health indices are discussed. Whilst it is concluded that evidence is now strong for the moderate alcohol-bone health association, at least in relation to bone mineral density, mechanisms are less clear. Both ethanol and non-ethanol components have been implicated as factors that positively affect bone health in the light of moderate consumption of alcoholic beverages, and four particular areas are discussed. First, recent findings suggest that moderate ethanol consumption acutely inhibits bone resorption, in a non-parathyroid hormone-and non-calcitonin-dependent fashion, which can only partly be attributed to an energy effect. Second, critical review of the literature does not support a role for moderate ethanol consumption affecting oestrogen status and leading to a knock-on effect on bone. Third, Si is present at high levels in certain alcoholic beverages, especially beer, and may have a measurable role in promoting bone formation. Fourth, a large body of work indicates that phytochemicals (e.g. polyphenols) from alcoholic beverages could influence bone health, but human data are lacking. With further work it is hoped to be able to model epidemiological observations and provide a clear pathway between the magnitude of association and the relative contribution of these mechanisms for the major classes of alcoholic beverage.

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Prenylflavonoids: A New Class of Non-Steroidal Phytoestrogen (Part 2). Estrogenic Effects of 18-Isopentenylnaringenin on Bone Metabolism

Cited by 63 publications

References 7 publications

Estrogenic and Antiestrogenic Activities of the Roots of Moghania philippinensis and Their Constituents

Estrogenic and Antiestrogenic Activities of the Roots of Moghania philippinensis and Their Constituents

Phytoestrogens

Moderate alcohol consumption and increased bone mineral density: potential ethanol and non-ethanol mechanisms

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